Name: 84-85-5|4-Methoxynaphthalen-1-ol|97%
Brand: Ambeed
SKU: A141603
Price: 19.0 USD
Availability: InStock
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1
[ 84-85-5 ]
[ 1244-92-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With oxygen; pyrographite In acetonitrile at 70℃; for 16h;
40%	With air for 16h; Ambient temperature; adsorbed onto silica gel;
	With alkali mit Luft;

	With potassium hexacyanoferrate(III)
	With ethanol; iron(III) chloride
	With sodium hydroxide; dihydrogen peroxide Ein nicht charakterisiertes Praeparat ist erhalten worden.;
	With lead dioxide; benzene

Reference： [1]Ogata, Tokutaro; Okamoto, Iwao; Kotani, Eiichi; Takeya, Tetsuya [Tetrahedron, 2004, vol. 60, # 18, p. 3941 - 3948]
[2]Calderon, Jose S; Thomson, Ronald H. [Journal of the Chemical Society. Perkin transactions I, 1988, p. 583 - 586]
[3]Russig [Journal fur praktische Chemie (Leipzig 1954), 1900, vol. <2> 62, p. 57]
[4]Russig [Journal fur praktische Chemie (Leipzig 1954), 1900, vol. <2> 62, p. 57]
[5]Russig [Journal fur praktische Chemie (Leipzig 1954), 1900, vol. <2> 62, p. 57]
[6]Current Patent Assignee: I.G. FARBENINDUSTRIE AG (historic) - FR758685, 1933, A Current Patent Assignee: G HOLDINGS INC - US2001992, 1933, A
[7]Goldschmidt; Wessbecher [Chemische Berichte, 1928, vol. 61, p. 374]

2
[ 84-85-5 ]
[ 106-95-6 ]
[ 107777-17-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium carbonate In acetone for 3h; Reflux;	1-Methoxy-4-allyloxynaphthalene (6) Anhydrous K2CO3 (7 g, 0.056 mol) was added to a solution of 4-methoxy-1-naphthol (5, 5.0 g, 0.028 mol) in dry acetone (50 mL). The mixture was stirred at 40 °C and freshly distilled allyl bromide (3.0 mL, 0.040 mol) was added dropwise. The contents were refluxed until completion of the reaction (3 h). Potassium carbonate was filtered off and the filtrate was concentrated under reduced pressure to give a viscous mass which was purified by column chromatography over neutral alumina using hexane as eluent to provide 1-methoxy-4-allyloxynaphthalene (6) as a colourless oil (5.7 g) in 94% yield. IR (neat): 1624, 1590, 1098 cm-1; 1H NMR δ ppm: 3.92 (s, 3H, -OCH3), 4.62 (d, J = 6.0 Hz, 2H, O-CH2-C=C), 5.28 (d, J = 10.6 Hz, 1H, C=C-H), 5.46 (d, J = 16.0 Hz, 1H, C=C-H), 6.04-6.18 (m, 1H, CH2-CH=CH2), 6.6-6.69 (d, J = 8.2 Hz, 2H, C2 & C3 H), 7.40-7.58 (m, 2H, C6-H & C7-H), 8.12-8.28 (m, 2H,C5-H & C8-H). Anal. calcd for C14H14O2: C, 78.48; H, 6.59; found: C, 78.41; H, 6.68%.
	With potassium carbonate; acetone
	With CsCO₃ In N,N-dimethyl-formamide

With potassium carbonate In acetone at 20℃; for 7h; Reflux;

ii. Procedure for the Synthesis of Compounds B2. General procedure: Allyl bromide (3.3 mL, 39 mmol, 1.1 equiv) was added dropwise over 20 min to a solution of B1 (35 mmol, 1.0 equiv) in acetone (40 mL) containing suspended K2CO3 (39 mmol, 1.1 equiv). The mixture was stirred at rt for 15 min, then it was heated to reflux for 7 h, after which time TLC showed that the reaction was complete. The mixture was cooled to rt and the solvent was evaporated. The residue was taken up with H2O (20mL) and extracted with Et2O (3×15 mL). The combined extracts were washed with brine (15mL), dried (Na2SO4) and evaporated. The residue was dried under high vacuum and used for the next step without purification.

Reference： [1]Limaye, Rohan A.; Joseph, Augustine R.; Natu, Arun D.; Paradkar, Madhusudan V. [Journal of Chemical Research, 2014, vol. 38, # 9, p. 568 - 570]
[2]Grinew; Terentjew [Zhurnal Obshchei Khimii, 1958, vol. 28, p. 75,77][J. Gen. Chem. USSR (Engl. Transl.), 1958, vol. 28, p. 77,78]
[3]Ollevier, Thierry; Mwene-Mbeja, Topwe M. [Tetrahedron Letters, 2006, vol. 47, # 24, p. 4051 - 4055]
[4]Jain, Nikita; Ciufolini, Marco A. [Synlett, 2015, vol. 26, # 5, p. 631 - 634]

3
[ 571-60-8 ]
[ 74-88-4 ]
[ 84-85-5 ]

Yield	Reaction Conditions	Operation in experiment
45%	With potassium carbonate In acetone at 20℃; for 24h;	1 synthesis of intermediate 1-1 18 g of 1,4-dihydroxynaphthalene was dissolved in 1 L of acetone, and then, 31 g of potassium carbonate and 11 g of methyl iodide were added thereto and then the mixture was stirred at room (e.g., ambient) temperature for 24 hours. The reaction solution was filtered, and the obtained filtrate was concentrated and the result was separation-purified by silica gel column chromatography to obtain Intermediate 1-1 (6.1 g, 45%)
	With methanol; potassium hydroxide

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - KR2015/29430, 2015, A Location in patent: Paragraph 0382-0385
[2]Russig [Journal fur praktische Chemie (Leipzig 1954), 1900, vol. <2> 62, p. 57]

4
[ 67-56-1 ]
[ 84-85-5 ]
[ 64648-86-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With [bis(acetoxy)iodo]benzene at 0 - 20℃; for 1h; Inert atmosphere;	To a solution of 4-methoxynaphthalen-1-ol (1.67 g, 9.60 mmol) in MeOH (50 mL), iodobenzene diacetate (3.70g, 11.5 mmol) was slowly added at 0 °C. After being stirred for 1 h at room temperature, the reaction mixturewas quenched with a saturated NaHCO3 aqueous solution (30 mL) and extracted with Et2O (30 mL x 3). Thecombined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. Thisresidue was purified by column chromatography on silica gel (hexane/EtOAc = 3 : 1) to give4,4-dimethoxynaphthalen-1(4H)-one in 93% yield (1.82 g, 8.92 mmol). According to the synthetic procedure for 1a, 4,4-dimethoxy-3,4-dihydronaphthalen-1(2H)-one 1b was obtainedin 98% yield (201 mg, 0.976 mmol) by hydrogenation reaction of 4,4-dimethoxynaphthalen-1(4H)-one (204 mg,1.00 mmol) using Willkinson’s catalyst (47.1 mg, 0.051 mmol) and H2 (1 atm) in benzene (40 mL) for 6 h atroom temperature after column chromatography on silica gel (hexane/EtOAc = 3 : 1).
85%	With [bis(acetoxy)iodo]benzene at 20℃; for 1h; Inert atmosphere;
74%	With [bis(acetoxy)iodo]benzene for 15h; Ambient temperature;

	With [bis(acetoxy)iodo]benzene at 25℃; for 1h;
	With [bis(acetoxy)iodo]benzene at 0℃; for 0.166667h;
	With [bis(acetoxy)iodo]benzene
	With [bis(acetoxy)iodo]benzene at 20℃;

Reference： [1]Yanai, Hikaru; Sasaki, Yuichi; Yamamoto, Yuki; Matsumoto, Takashi [Synlett, 2015, vol. 26, # 17, p. 2457 - 2461]
[2]Location in patent: experimental part Hammill, Jared T.; Contreras-García, Julia; Virshup, Aaron M.; Beratan, David N.; Yang, Weitao; Wipf, Peter [Tetrahedron, 2010, vol. 66, # 31, p. 5852 - 5862]
[3]Fleck; Hobart; Morrow [Synthetic Communications, 1992, vol. 22, # 1, p. 179 - 187]
[4]Wells, Geoffrey; Berry, Jane M.; Bradshaw, Tracey D.; Burger, Angelika M.; Seaton, Angela; Wang, Bo; Westwell, Andrew D.; Stevens, Malcolm F. G. [Journal of Medicinal Chemistry, 2003, vol. 46, # 4, p. 532 - 541]
[5]Liu, Yingjie; Liu, Jingxin; Wang, Mang; Liu, Jun; Liu, Qun [Advanced Synthesis and Catalysis, 2012, vol. 354, # 14-15, p. 2678 - 2682]
[6]Kamitanaka, Tohru; Morimoto, Koji; Tsuboshima, Kohei; Koseki, Daichi; Takamuro, Hitoho; Dohi, Toshifumi; Kita, Yasuyuki [Angewandte Chemie - International Edition, 2016, vol. 55, # 50, p. 15535 - 15538][Angew. Chem., 2016, vol. 128, # 50, p. 15764 - 15767,4]
[7]Kamitanaka, Tohru; Tsunoda, Yusuke; Fujita, Yuriko; Dohi, Toshifumi; Kita, Yasuyuki [Organic Letters, 2021, vol. 23, # 23, p. 9025 - 9029]

5
[ 637-69-4 ]
[ 84-85-5 ]
[ 139016-15-2 ]

Yield	Reaction Conditions	Operation in experiment
35%	With lithium perchlorate; acetic acid In acetonitrile for 3h; Ambient temperature; electrolyse, platinum electrodes;
	With μ-Oxo-I,I'-bis(trifluoroacetato-O)-I,I'-diphenyldiiodine(III) In acetonitrile at 0 - 20℃;	Typical procedure for the oxidative coupling of phenols 1 with styrenes 2 using the PIFA dimer leading to dihydrobenzofurans 3 General procedure: To an ice-cooled solution of equimolar phenol 1a (24.8 mg, 0.20 mmol) and styrene 2a (27.6 mg, 0.20mmol) in MeCN (0.5 mL), the PIFA dimer (65.0 mg, 0.10 mmol) was added in one portion at room temperature. The reaction mixture was stirred for 30 min and then it was quenched with solid sodium hydrogen carbonate. After filtration, solvent was removed in vacuo and the residue was purified by column chromatography on silica-gel to give 2-aryldihydrobenzofuran 3aa (40.1 mg, 0.152 mmol) in 76% yield.

Reference： [1]Gates, Bradley D.; Dalidowicz, Peter; Tebben, Andrew; Wang, Shaopeng; Swenton, John S. [Journal of Organic Chemistry, 1992, vol. 57, # 7, p. 2135 - 2143]
[2]Dohi, Toshifumi; Toyoda, Yosuke; Nakae, Tomofumi; Koseki, Daichi; Kubo, Hiroko; Kamitanaka, Tohru; Kita, Yasuyuki [Heterocycles, 2015, vol. 90, # 1, p. 631 - 644]

6
[ 84-85-5 ]
[ 1244-92-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With p-benzoquinone In dichloromethane at 23℃; for 2h;
99%	With p-benzoquinone In dichloromethane at 20℃; for 2h;
95%	With oxygen In acetonitrile at 70℃; for 16h;

93%	With dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium carbonate In water; ethyl acetate at 20℃; for 24h;
27.1%	With [1,4]naphthoquinone In dichloromethane at 20℃; for 2h; Inert atmosphere;	4.2. Synthesis of the binaphthoquinones 4-Methoxy-1-naphthol (200mg, 1.16mmol) and 1,4-benzoquinone (74mg, 0.68mmol) were dissolved in CH2Cl2 (25mL) and the mixture was stirred at room temperature under dry argon for 2h. The solvent was evaporated and the residue was purified by column chromatography (silica gel; petroleum ether/CH2Cl2, v/v=21/1), then the crude product was recrystallized from CH2Cl2 to obtain the (E)-4,4′-dimethoxy-1H,1′H-[2,2′-binaphthalenylidene]-1,1′-dione as a blue powder solid (108mg, 27.1%) [24]. Subsequently, 69% HNO3 (4.7mL) was added into the above product. The reaction was stirred at 0°C for 15min. The mixture was poured into the excess ice-water to produce yellow solid after stirring for a moment. The solid was filtered and recrystallized from CHCl3 to give BQ as a yellow powder solid (50mg, 50.7%) [25]. BQ-HC and BQ-DC were synthesized as described previously [26]. The purity of the binaphthoquinones was determined to be >95% by a Waters HPLC system consisting of 1525 binary HPLC pump and 2998 photodiode array detector (C-18 column, Sun Fire, 4.6mm×150mm) at room temperature. Methanol-water was used as a mobile phase, and the flow rate is 1.0mL/min. Concerning 1H NMR, 13C NMR and HRMS spectra of the binaphthoquinones, see also the supplementary data.
	With iron(III) chloride
	With silver(l) oxide In chloroform
	Multi-step reaction with 2 steps 1: 80 percent / p-chloranil / CH₂Cl₂ / 3 h / 23 °C 2: 98 percent / 1,4-benzoquinone / CH₂Cl₂ / 1 h / 23 °C
	Multi-step reaction with 2 steps 1: 67 percent / O₂ / SnO₂ / CH₂Cl₂ / 72 h / 23 °C 2: 93 percent / O₂ / SnO₂ / acetonitrile / 0.75 h / 70 °C
	Multi-step reaction with 2 steps 1: 81 percent / O₂ / SnO₂ / nitromethane / 72 h / 23 °C 2: 93 percent / O₂ / SnO₂ / acetonitrile / 0.75 h / 70 °C

Reference： [1]Takeya, Tetsuya; Kondo, Hiromu; Otsuka, Tsuyoshi; Doi, Hirohisa; Okamoto, Iwao; Kotani, Eiichi [Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 2, p. 199 - 206]
[2]Takeya, Tetsuya; Kondo, Hiromu; Otsuka, Tsuyoshi; Tomita, Kazuho; Okamoto, Iwao; Tamura, Osamu [Organic Letters, 2007, vol. 9, # 15, p. 2807 - 2810]
[3]Otsuka, Tsuyoshi; Okamoto, Iwao; Kotani, Eiichi; Takeya, Tetsuya [Tetrahedron Letters, 2004, vol. 45, # 12, p. 2643 - 2647]
[4]Uyanik, Muhammet; Nagata, Dai; Ishihara, Kazuaki [Chemical Communications, 2021, vol. 57, # 88, p. 11625 - 11628]
[5]Dai, Fang; Yan, Wen-Jing; Fu, Xing; Zheng, Ya-Long; Du, Yu-Ting; Bao, Xia-Zhen; Kang, Yan-Fei; Jin, Xiao-Ling; Zhou, Bo [European Journal of Medicinal Chemistry, 2018, vol. 159, p. 317 - 323]
[6]Hewgill,F.R.; Mullings,L.R. [Australian Journal of Chemistry, 1975, vol. 28, p. 355 - 367]
[7]Laatsch, Hartmut [Liebigs Annalen der Chemie, 1984, # 7, p. 1367 - 1381]
[8]Takeya, Tetsuya; Kondo, Hiromu; Otsuka, Tsuyoshi; Doi, Hirohisa; Okamoto, Iwao; Kotani, Eiichi [Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 2, p. 199 - 206]
[9]Otsuka, Tsuyoshi; Okamoto, Iwao; Kotani, Eiichi; Takeya, Tetsuya [Tetrahedron Letters, 2004, vol. 45, # 12, p. 2643 - 2647]
[10]Otsuka, Tsuyoshi; Okamoto, Iwao; Kotani, Eiichi; Takeya, Tetsuya [Tetrahedron Letters, 2004, vol. 45, # 12, p. 2643 - 2647]

7
[ 84-85-5 ]
[ 82663-57-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	In dichloromethane at 100℃; for 18h;
98%	With tin(IV) chloride In dichloromethane at 100℃; for 18h;
	With tetrabutylammonium perchlorate In acetonitrile electrochemical oxidation;

	Multi-step reaction with 4 steps 1: 75 percent / Et₃N / acetonitrile / 2 h 2: MeCOCl / acetonitrile / 0.5 h / 0 °C 3: Et₃N / acetonitrile / 2 h 4: tetraammoniumcerium(IV) nitrate; 2,6-di-tert-butylpyridine / 0.02 h / 25 °C
	Multi-step reaction with 2 steps 1: 75 percent / NaI; Et₃N / acetonitrile; tetrahydrofuran / 2 h / 0 - 20 °C 2: 56 percent / tetraammoniumcerium(IV) nitrate; 2,6-di-tert-butylpyridine / 0.02 h / 25 °C
	Multi-step reaction with 2 steps 1: Ag₂O / CHCl₃ 2: CHCl₃
	With Pt(5%)Bi(5%)/C; dihydrogen peroxide In water; acetone at 20℃; for 0.666667h;
	With dihydrogen peroxide In nitromethane; water at 96℃; for 0.666667h;	Oxidation Reactions and Product Separation General procedure: Oxidative coupling reactions (at r. t. or under reflux)were carried out in the same manner as described earlier[15]. That is, for each reaction 6.34 mmol starting material(SM) and 0.0401 g catalyst were used in 25 mL ofsolvent, to which 22.1 mmol H2O2 was added as a30% aq. solution over 40 min. The reaction mixture wasseparated by column chromatography. Product selectivitieswere calculated as mole percentages based on themoles of SM incorporated into each product. Turnoverfrequencies (TOFs) are reported as moles of H2O2required for the formation of all identified products(compare Scheme 1) per moles of platinum present inthe catalyst over the total reaction time (min-1)

Reference： [1]Takeya, Tetsuya; Doi, Hirohisa; Ogata, Tokutaro; Okamoto, Iwao; Kotani, Eiichi [Tetrahedron, 2004, vol. 60, # 41, p. 9049 - 9060]
[2]Takeya, Tetsuya; Doi, Hirohisa; Ogata, Tokutaro; Otsuka, Tsuyoshi; Okamoto, Iwao; Kotani, Eiichi [Tetrahedron, 2004, vol. 60, # 30, p. 6295 - 6310]
[3]Laatsch, Harmut; Sigel, Christoph; Kral, Andreas [Chemische Berichte, 1994, vol. 127, # 2, p. 393 - 400]
[4]Schmittel, Michael; Haeuseler, Andreas [Zeitschrift fur Naturforschung, B: Chemical Sciences, 2003, vol. 58, # 2-3, p. 211 - 216]
[5]Schmittel, Michael; Haeuseler, Andreas [Zeitschrift fur Naturforschung, B: Chemical Sciences, 2003, vol. 58, # 2-3, p. 211 - 216]
[6]Laatsch, Hartmut [Liebigs Annalen der Chemie, 1984, # 7, p. 1367 - 1381]
[7]Maphoru, Mabuatsela V.; Heveling, Josef; Kesavan Pillai, Sreejarani [European Journal of Organic Chemistry, 2016, vol. 2016, # 2, p. 331 - 337]
[8]Maphoru; Heveling; Kesavan Pillai [Kinetics and Catalysis, 2017, vol. 58, # 4, p. 441 - 447][Kinet. Katal., 2017, vol. 58, # 4, p. 465 - 472,8]

8
[ 84-85-5 ]
[ 4180-23-8 ]
[ 139016-16-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	With ammonium peroxydisulfate In nitromethane for 12h; Irradiation; Inert atmosphere;
96%	With tetrabutylammonium tetrafluoroborate In acetonitrile Electrolysis;
96%	With tetrabutylammonium tetrafluoroborate In acetonitrile Electrolysis;

92%	With ammonium peroxydisulfate; tris(2,2′-bipyrazine-N1,N1′)ruthenium(II) hexafluorophosphate In acetonitrile for 12h; Irradiation; Schlenk technique;
64%	With lithium perchlorate; acetic acid In acetonitrile for 3h; Ambient temperature; electrolysis, platinum electrodes;

Reference： [1]Huang, Wei; Huber, Niklas; Jiang, Shuai; Landfester, Katharina; Zhang, Kai A. I. [Angewandte Chemie - International Edition, 2020, vol. 59, # 42, p. 18368 - 18373][Angew. Chem., 2020, vol. 132, # 42, p. 18526 - 18531,6]
[2]El-Seedi, Hesham R.; Yamamura, Shosuke; Nishiyama, Shigeru [Tetrahedron Letters, 2002, vol. 43, # 18, p. 3301 - 3304]
[3]El-Seedi, Hesham R; Yamamura, Shosuke; Nishiyama, Shigeru [Tetrahedron, 2002, vol. 58, # 37, p. 7485 - 7489]
[4]Blum, Travis R.; Zhu, Ye; Nordeen, Sarah A.; Yoon, Tehshik P. [Angewandte Chemie - International Edition, 2014, vol. 53, # 41, p. 11056 - 11059][Angew. Chem., 2015, vol. 126, # 41, p. 11236 - 11239,4]
[5]Gates, Bradley D.; Dalidowicz, Peter; Tebben, Andrew; Wang, Shaopeng; Swenton, John S. [Journal of Organic Chemistry, 1992, vol. 57, # 7, p. 2135 - 2143]

9
[ 84-85-5 ]
[ 130-15-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With oxone; tetrabutylammomium bromide In water; acetonitrile at 20℃; for 1h;
95%	With silica gel supported cerium(IV) ammonium nitrate-NaBrO₃ In dichloromethane; water at 40℃; for 2h;	Oxidation Reactions; Typical Procedure General procedure: A solution of CAN (0.056 g, 0.102 mmoles) and sodium bromate (0.780 g, 5.17 mmoles) in H2O (3 mL) was added slowly to vigorously stirred anhydrous silica gel (5 g) that was contained in a 100 mLround-bottom flask containing a magnetic stirring bar and fitted with a rubber septum. After complete addition of the aqueous solution, stirring was continued until a free-flowing powder was obtained.CH2Cl2 (25 mL) was then added to the flask and a solution of hydroquinone 1A (220.23 mg, 2.0 mmol), in CH2Cl2 (5 mL) was added slowly to the stirred heterogeneous mixture. A condenser was attached to the flask and the reaction was heated to reflux. Disappearance of 1A was monitored by thin-layer chromatography (EtOAc-hexane, 1:4; panisaldehyde/sulfuric acid as staining agent). Upon complete disappearance of 1A (ca. 2 h), the reaction mixture was filtered through a sintered glass funnel, the solid residue was washed with additional CH2Cl2 (3 × 10 mL), and the washings were added to the filtrate. Removal of solvent from the organic solution under vacuum gave an orange solid. Radial chromatography of the crude product (EtOAc-hexane,1:9) gave 1,4-benzoquinone 2A (89 mg, 82%) as an orange solid.
91%	With Pyridine-2,6-dicarboxylic acid N-oxide; tert.-butylhydroperoxide In water; acetonitrile at 50℃; for 11h;

90%	With cerium(IV) ammonium nitrate; silica gel In dichloromethane
86%	With Oxone at 20℃; for 0.166667h;
76%	With ammonium persulfate; silver nitrate In water; acetonitrile for 18h; Ambient temperature;

Reference： [1]Location in patent: experimental part Yakura, Takayuki; Ozono, Ayaka; Morimoto, Kohei [Chemical and Pharmaceutical Bulletin, 2011, vol. 59, # 1, p. 132 - 134]
[2]Ali, Mohammed Hashmat; Welker, Andrea; York, Crystal [Synthesis, 2015, vol. 47, # 20, p. 3207 - 3211]
[3]Krohn, Karsten; Vitz, Juergen [Advanced Synthesis and Catalysis, 2000, vol. 342, # 8, p. 825 - 827]
[4]Ali, Mohammed Hashmat; Niedbalski, Melinda; Bohnert, Gary; Bryant, Daniel [Synthetic Communications, 2006, vol. 36, # 12, p. 1751 - 1759]
[5]Yakura, Takayuki; Konishi, Tatsuya [Synlett, 2007, # 5, p. 765 - 768]
[6]Tanoue, Yasuhiro; Sakata, Kazunori; Hashimoto, Mamoru; Morishita, Shin-ichi; Hamada, Moritsugu [Bulletin of the Chemical Society of Japan, 1994, vol. 67, # 9, p. 2593 - 2595]

10
[ 84-85-5 ]
[ 75-36-5 ]
[ 73584-59-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	With scandium tris(trifluoromethanesulfonate) In nitromethane; toluene at 100℃; for 6h;
82%	Stage #1: 4-methoxynaphth-1-ol With titanium tetrachloride at 20℃; Stage #2: acetyl chloride at 20 - 120℃; for 1.25h;
80.6%	With aluminium trichloride In 1,2-dichloro-ethane at 0℃; for 15h;

72%

With scandium tris(trifluoromethanesulfonate) In nitromethane; toluene at 170℃; for 0.0833333h; Irradiation;

14 EXAMPLE 14 [0198]; Synthesis of 6-Methoxy-2-(3,4,5-Trimethoxyphenyl)-3,4-Dihydro-2H-Benzo[H]Chromen-4-One (SR 13801) [0200] Synthesis of 2-acetyl-4-methoxy-1-naphthol 12. A solution of 4-methoxy-1-naphthol 11 (435 mg, 2.5 mmol) in toluene (5 mL) and nitromethane (0.75 mL) was treated with scandium triflate (61.52 mg, 0.125 mmol) and acetyl chloride (0.195 mL, 2.75 mmol) and irradiated in the microwave reactor (Personal Chemistry, Inc) at a temperature of 170° C. for 5 minutes. The cooled reaction was diluted with methylene chloride and filtered through a small pad of silica gel. The filtrate was evaporated to dryness and purified via flash chromatography, eluting the pure C-acylated product 12 with CH2Cl2/hexanes (1:1). Pooled fractions were evaporated to afford 12 as a greenish yellow solid (0.388 g, 72% yield). 1H NMR (300 MHz, CDCl3): δ2.69 (s, 3H, COCH3), 3.99 (s, 3H, OCH3), 6.84 (s, 1H, Ar-3-H), 7.80 (m, 2H, Ar-H), 8.10 (d, 1H, Ar-H), 8.21 (d, 1H, Ar-H), 13.76 (s, 1H, OH).

Reference： [1]Kobayashi, Shue; Moriwaki, Mitsuhiro; Hachiya, Iwao [Bulletin of the Chemical Society of Japan, 1997, vol. 70, # 1, p. 267 - 273]
[2]Bensari, Ahlem; Zaveri, Nurulain T. [Synthesis, 2003, # 2, p. 267 - 271]
[3]Laatsch, Hartmut; Talvitie, Antti; Kral, Andreas; Ernst, Bernd-Peter; Noltemeyer, Mathias [Advanced Synthesis and Catalysis, 1996, vol. 338, # 2, p. 140 - 145]
[4]Current Patent Assignee: SRI INTERNATIONAL INC - US2003/229136, 2003, A1 Location in patent: Page 22

11
[ 84-85-5 ]
[ 201230-82-2 ]
[ 75-07-0 ]
5-Methoxy-3-methyl-3H-naphtho[1,2-b]furan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; trifluoroacetic acid In benzene at 120℃; for 18h;

Reference： [1]Satoh, Tetsuya; Tsuda, Takatoshi; Kushino, Yuichi; Miura, Masahiro; Nomura, Masakatsu [Journal of Organic Chemistry, 1996, vol. 61, # 19, p. 6476 - 6477]

12
[ 107-86-8 ]
[ 84-85-5 ]
[ 573-13-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With phenylboronic acid In acetic acid; toluene for 4h; Heating;
95%	With acetic acid; phenylboronic acid In toluene for 16h; Heating;
79%	With ethylenediaminediacetic acid In chloroform at 60℃; for 24h;

60%	In chloroform for 24h; Heating;
60%	With ethylenediamine diacetic acid In chloroform at 20℃; for 24h; Inert atmosphere; Reflux;
56%	With 1,2-diamino-benzene In dichloromethane at 40℃; for 60h; Inert atmosphere; Molecular sieve;	4. General Procedure for the Synthesis of 2H-Benzo[h]Chromene 3 General procedure: Dry CH2Cl2 (1.0 mL) was added to a mixture of o-phenylenediamine (IX, 0.04 mmol),enal 1 (0.30 mmol) and arylol 2 (0.20 mmol) under Ar. The reaction was stirred at 40 Cuntil the completion of 2 monitored by TLC. Then, the mixture was applied to columnchromatography directly and eluted with ethyl ether and hexane (9/1) to give product 3.

Reference： [1]Alves, Glaucia B. C.; Lopes, Rosangela S. C.; Lopes, Claudio C.; Snieckus, Victor [Synthesis, 1999, # 11, p. 1875 - 1877]
[2]Chauder, Brian A.; Lopes, Claudio C.; Lopes, Rosangela S. C.; Da Silva, Alcides J. M.; Snieckus, Victor [Synthesis, 1998, # 3, p. 279 - 282]
[3]Cadelis, Melissa M.; Barker, David; Copp, Brent R. [Synlett, 2012, vol. 23, # 20, p. 2939 - 2942]
[4]Yong, Rok Lee; Yun, Mi Kim [Helvetica Chimica Acta, 2007, vol. 90, # 12, p. 2401 - 2413]
[5]Location in patent: experimental part Wang, Xue; Chen, Ye; Lee, Yong Rok [Bulletin of the Korean Chemical Society, 2011, vol. 32, # 1, p. 153 - 156]
[6]Gao, Feng; Ji, Peng; Meng, Xiang; Wang, Wei; Zeng, Fanxun; Zhang, Yueteng [Molecules, 2021, vol. 26, # 12]

13
[ 84-85-5 ]
[ 45742-39-0 ]
(2R,3S,4S,6R)-6-(1-Hydroxy-4-methoxy-naphthalen-2-yl)-2-methyl-tetrahydro-pyran-3,4-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With trimethylsilyl trifluoromethanesulfonate; silver perchlorate In acetonitrile at 25℃; for 0.5h;

Reference： [1]Toshima, Kazunobu; Matsuo, Goh; Ishizuka, Toru; Ushiki, Yasunobu; Nakata, Masaya; Matsumura, Shuichi [Journal of Organic Chemistry, 1998, vol. 63, # 7, p. 2307 - 2313]

14
[ 84-85-5 ]
[ 583-53-9 ]
4-methoxybenzo[b]naphtho[1,8-de]pyran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With caesium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 140℃; for 24h;
33%	With palladium diacetate; caesium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 140℃; for 15h;	3.c.1 (c-1) Synthesis of 4-methoxybenzo[kl]xanthene 4-methoxy-1-naphthol (6.97g) and 1,2-dibromobenzene (11.3g) were dissolved in 200 mL of dimethylformamide. Cesium carbonate (52.13g), triphenylphosphine (2.10g) and palladium acetate (II) (0.45g) were added sequentially, and stirred at 140°C for 15 hours. The resulting solution was cooled to room temperature and separated by adding water and ethyl acetate. The water phase was extracted with ethyl acetate and washed with water and brine. After organic phases were combined and dried over anhydrous sodium sulfate and filtrated, the solution was evaporated. Water and methanol were added to the resulting residue. The resulting solution was extracted with diethyl ether and ethyl acetate, and washed with water and brine. After organic phases were combined and dried over anhydrous sodium sulfate and filtrated, the solution was evaporated. After purified by silica gel chromatography, the obtained residue was dispersed and washed and then dried, whereby 3.26g of yellow solids of 4-methoxybenzo[kl]xanthene were obtained (yield: 33%).

Reference： [1]Terao, Yoshito; Satoh, Tetsuya; Miura, Masahiro; Nomura, Masakatsu [Bulletin of the Chemical Society of Japan, 1999, vol. 72, # 10, p. 2345 - 2350]
[2]Current Patent Assignee: IDEMITSU KOSAN CO LTD - EP2644607, 2013, A1 Location in patent: Paragraph 0069; 0070

15
[ 84-85-5 ]
[ 609-67-6 ]
4-methoxy-1-naphthyl-2-iodobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%
88%	With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 25℃;

Reference： [1]Qabaja, Ghassan; M. Perchellet, Elisabeth; Perchellet, Jean-Pierre; Jones, Graham B. [Tetrahedron Letters, 2000, vol. 41, # 17, p. 3007 - 3010]
[2]Qabaja; Jones [Journal of Organic Chemistry, 2000, vol. 65, # 21, p. 7187 - 7194]

16
[ 84-85-5 ]
[ 3408-13-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With silver(II) oxide; nitric acid at 20℃; for 1h;	Method 1: To a round-bottom flask covered in foil, was added 4-methoxynaphthol (12) (53mg, 0.306 mmol), AgO (304 mg, 2.46 mmol) and acetone (25 mL), followed by 40% aqueous nitric acid (1.5 mL), which was added dropwise over 5 minutes. The reaction mixture wasstirred at room temperature for 1 hour, then diluted with water (50 mL). The crude materialwas extracted with chloroform, washed with brine (2 x 10 mL), and dried over sodium sulfate.Evaporation of the solvent in vacuo resulted in the isolation of the pure binaphthyl 14 as a yellow solid (48 mg, 100% yield).
89%	With silver(II) oxide; nitric acid In acetone at 20℃; for 0.583333h;
59%	With oxygen In dichloromethane at 23℃; for 67h;

	Multi-step reaction with 2 steps 1: 88 percent / O₂ / SnCl₄ / CH₂Cl₂ / 0.5 h / 23 °C 2: 36 percent / O₂ / SnCl₄ / CH₂Cl₂ / 12 h / 23 °C
	Multi-step reaction with 2 steps 1: 95 percent / activated charcoal; O₂ / acetonitrile / 16 h / 70 °C 2: 99 percent / HNO₃ / H₂O / 0.25 h / 0 °C
	Multi-step reaction with 2 steps 1: 75 percent / ZrO₂; O₂ / acetonitrile / 1.5 h / 70 °C 2: 99 percent / HNO₃ / H₂O / 0.25 h / 0 °C
	Multi-step reaction with 3 steps 1: 95 percent / O₂ / activated charcoal / acetonitrile / 16 h / 70 °C 2: 94 percent / SnO₂ / CH₂Cl₂ / 19 h / 23 °C 3: HNO₃ / H₂O
	Multi-step reaction with 4 steps 1: 67 percent / O₂ / SnO₂ / CH₂Cl₂ / 72 h / 23 °C 2: 93 percent / O₂ / SnO₂ / acetonitrile / 0.75 h / 70 °C 3: 94 percent / SnO₂ / CH₂Cl₂ / 19 h / 23 °C 4: HNO₃ / H₂O
	Multi-step reaction with 2 steps 1: 28 percent / O₂ / SnO₂ / CH₂Cl₂ / 72 h / 23 °C 2: HNO₃ / H₂O
	Multi-step reaction with 4 steps 1: 81 percent / O₂ / SnO₂ / nitromethane / 72 h / 23 °C 2: 93 percent / O₂ / SnO₂ / acetonitrile / 0.75 h / 70 °C 3: 94 percent / SnO₂ / CH₂Cl₂ / 19 h / 23 °C 4: HNO₃ / H₂O
	Multi-step reaction with 3 steps 1: 6 percent / O₂ / SnO₂ / nitromethane / 72 h / 23 °C 2: 94 percent / SnO₂ / CH₂Cl₂ / 19 h / 23 °C 3: HNO₃ / H₂O
	Multi-step reaction with 5 steps 1: Ag₂O / CHCl₃ 2: CHCl₃ 3: 91 percent / CHCl₃; acetone; diethyl ether / 0.17 h / -20 °C 4: 96 percent / FeCl₃ / acetonitrile; H₂O / Ambient temperature 5: Br₂ / acetic acid / 0.5 h
	Multi-step reaction with 5 steps 1: Ag₂O / CHCl₃ 2: CHCl₃ 3: 91 percent / CHCl₃; acetone; diethyl ether / 0.17 h / -20 °C 4: 55 percent / Ag₂O / CHCl₃ / 1 h / Ambient temperature 5: Br₂ / acetic acid / 0.5 h
	Multi-step reaction with 2 steps 1: [1,4]naphthoquinone / dichloromethane / 2 h / 20 °C / Inert atmosphere 2: nitric acid / 0.25 h / 0 °C

Reference： [1]Daley, Sharna-Kay A.; Downer-Riley, Nadale K. [Synlett, 2019, vol. 30, # 3, p. 325 - 328]
[2]Tanoue, Yasuhiro; Sakata, Kazunori; Hashimoto, Mamoru; Morishita, Shin-Ich; Hamada, Moritsugu; Kai, Norihisa; Nagai, Takeshi [Tetrahedron, 2002, vol. 58, # 1, p. 99 - 104]
[3]Takeya, Tetsuya; Doi, Hirohisa; Ogata, Tokutaro; Okamoto, Iwao; Kotani, Eiichi [Tetrahedron, 2004, vol. 60, # 41, p. 9049 - 9060]
[4]Takeya, Tetsuya; Doi, Hirohisa; Ogata, Tokutaro; Okamoto, Iwao; Kotani, Eiichi [Tetrahedron, 2004, vol. 60, # 41, p. 9049 - 9060]
[5]Ogata, Tokutaro; Okamoto, Iwao; Kotani, Eiichi; Takeya, Tetsuya [Tetrahedron, 2004, vol. 60, # 18, p. 3941 - 3948]
[6]Ogata, Tokutaro; Okamoto, Iwao; Kotani, Eiichi; Takeya, Tetsuya [Tetrahedron, 2004, vol. 60, # 18, p. 3941 - 3948]
[7]Otsuka, Tsuyoshi; Okamoto, Iwao; Kotani, Eiichi; Takeya, Tetsuya [Tetrahedron Letters, 2004, vol. 45, # 12, p. 2643 - 2647]
[8]Otsuka, Tsuyoshi; Okamoto, Iwao; Kotani, Eiichi; Takeya, Tetsuya [Tetrahedron Letters, 2004, vol. 45, # 12, p. 2643 - 2647]
[9]Otsuka, Tsuyoshi; Okamoto, Iwao; Kotani, Eiichi; Takeya, Tetsuya [Tetrahedron Letters, 2004, vol. 45, # 12, p. 2643 - 2647]
[10]Otsuka, Tsuyoshi; Okamoto, Iwao; Kotani, Eiichi; Takeya, Tetsuya [Tetrahedron Letters, 2004, vol. 45, # 12, p. 2643 - 2647]
[11]Otsuka, Tsuyoshi; Okamoto, Iwao; Kotani, Eiichi; Takeya, Tetsuya [Tetrahedron Letters, 2004, vol. 45, # 12, p. 2643 - 2647]
[12]Laatsch, Hartmut [Liebigs Annalen der Chemie, 1984, # 7, p. 1367 - 1381]
[13]Laatsch, Hartmut [Liebigs Annalen der Chemie, 1984, # 7, p. 1367 - 1381]
[14]Dai, Fang; Yan, Wen-Jing; Fu, Xing; Zheng, Ya-Long; Du, Yu-Ting; Bao, Xia-Zhen; Kang, Yan-Fei; Jin, Xiao-Ling; Zhou, Bo [European Journal of Medicinal Chemistry, 2018, vol. 159, p. 317 - 323]

17
[ 84-85-5 ]
[ 35889-52-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	With tin(IV) chloride In dichloromethane at 100℃; for 65h;
	Multi-step reaction with 2 steps 1: 88 percent / O₂ / SnCl₄ / CH₂Cl₂ / 0.5 h / 23 °C 2: 27 percent / HCl / methanol / 5 h / 110 °C
	Multi-step reaction with 3 steps 1: 88 percent / O₂ / SnCl₄ / CH₂Cl₂ / 0.5 h / 23 °C 2: 24 percent / HCl / methanol / 5 h / 110 °C 3: 91 percent / K₂CO₃ / dimethylformamide / 4 h / 23 °C

	Multi-step reaction with 2 steps 1: 98 percent / SnCl₄ / CH₂Cl₂ / 18 h / 100 °C 2: 91 percent / SnCl₄ / CH₂Cl₂ / 63 h / 100 °C
	Multi-step reaction with 7 steps 1: Ag₂O / CHCl₃ 2: CHCl₃ 3: 91 percent / CHCl₃; acetone; diethyl ether / 0.17 h / -20 °C 4: 96 percent / FeCl₃ / acetonitrile; H₂O / Ambient temperature 5: 33 percent / BCl₃ / CH₂Cl₂ / 0.03 h / Ambient temperature 6: H₂/NaOAc / Pd/C / benzene; methanol 7: 93 percent / acetone
	Multi-step reaction with 7 steps 1: Ag₂O / CHCl₃ 2: CHCl₃ 3: 91 percent / CHCl₃; acetone; diethyl ether / 0.17 h / -20 °C 4: 55 percent / Ag₂O / CHCl₃ / 1 h / Ambient temperature 5: 33 percent / BCl₃ / CH₂Cl₂ / 0.03 h / Ambient temperature 6: H₂/NaOAc / Pd/C / benzene; methanol 7: 93 percent / acetone
	Multi-step reaction with 7 steps 1: Ag₂O / CHCl₃ 2: CHCl₃ 3: 91 percent / CHCl₃; acetone; diethyl ether / 0.17 h / -20 °C 4: 41 percent / Ag₂O / CHCl₃ / 1 h / Ambient temperature 5: 95 percent / conc. HCl / dioxane 6: H₂/NaOAc / Pd/C / benzene; methanol 7: 93 percent / acetone
	Multi-step reaction with 6 steps 1: Ag₂O / CHCl₃ 2: CHCl₃ 3: 91 percent / CHCl₃; acetone; diethyl ether / 0.17 h / -20 °C 4: 41 percent / Ag₂O / CHCl₃ / 1 h / Ambient temperature 5: 95 percent / H₂ / Pd/C / benzene; acetic acid 6: 93 percent / acetone

Reference： [1]Ogata, Tokutaro; Okamoto, Iwao; Doi, Hirohisa; Kotani, Eiichi; Takeya, Tetsuya [Tetrahedron Letters, 2003, vol. 44, # 10, p. 2041 - 2044] Takeya, Tetsuya; Doi, Hirohisa; Ogata, Tokutaro; Otsuka, Tsuyoshi; Okamoto, Iwao; Kotani, Eiichi [Tetrahedron, 2004, vol. 60, # 30, p. 6295 - 6310]
[2]Takeya, Tetsuya; Doi, Hirohisa; Ogata, Tokutaro; Okamoto, Iwao; Kotani, Eiichi [Tetrahedron, 2004, vol. 60, # 41, p. 9049 - 9060]
[3]Takeya, Tetsuya; Doi, Hirohisa; Ogata, Tokutaro; Okamoto, Iwao; Kotani, Eiichi [Tetrahedron, 2004, vol. 60, # 41, p. 9049 - 9060]
[4]Takeya, Tetsuya; Doi, Hirohisa; Ogata, Tokutaro; Otsuka, Tsuyoshi; Okamoto, Iwao; Kotani, Eiichi [Tetrahedron, 2004, vol. 60, # 30, p. 6295 - 6310]
[5]Laatsch, Hartmut [Liebigs Annalen der Chemie, 1984, # 7, p. 1367 - 1381]
[6]Laatsch, Hartmut [Liebigs Annalen der Chemie, 1984, # 7, p. 1367 - 1381]
[7]Laatsch, Hartmut [Liebigs Annalen der Chemie, 1984, # 7, p. 1367 - 1381]
[8]Laatsch, Hartmut [Liebigs Annalen der Chemie, 1984, # 7, p. 1367 - 1381]

18
[ 84-85-5 ]
[ 172033-73-7 ]
4-(4-methoxynaphthalen-1-yloxy)naphthalene-1-carbaldehyde [ No CAS ]

Reference： [1]Organic letters,2003,vol. 5,p. 1155 - 1158

19
[ 84-85-5 ]
[ 1244-92-4 ]
[ 82663-57-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 81% 2: 6%	With oxygen In nitromethane at 23℃; for 72h;
1: 80% 2: 16%	With chloranil In dichloromethane at 23℃; for 3h;

Reference： [1]Otsuka, Tsuyoshi; Okamoto, Iwao; Kotani, Eiichi; Takeya, Tetsuya [Tetrahedron Letters, 2004, vol. 45, # 12, p. 2643 - 2647]
[2]Takeya, Tetsuya; Kondo, Hiromu; Otsuka, Tsuyoshi; Doi, Hirohisa; Okamoto, Iwao; Kotani, Eiichi [Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 2, p. 199 - 206]

20
[ 84-85-5 ]
8,13a-dimethoxy-6a,13a-dihydro-6H-dinaphtho[1,2-b:2',1'-d]furan-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With oxygen In dichloromethane at 23℃; for 0.5h;

Reference： [1]Takeya, Tetsuya; Doi, Hirohisa; Ogata, Tokutaro; Okamoto, Iwao; Kotani, Eiichi [Tetrahedron, 2004, vol. 60, # 41, p. 9049 - 9060]

21
[ 84-85-5 ]
4-methoxy-2-nitro-naphthalen-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With toluene-4-sulfonic acid In acetone at 50℃; for 0.5h;

Reference： [1]Anuradha; Srinivas; Aparna; Rao, J. Madhusudana [Tetrahedron Letters, 2006, vol. 47, # 28, p. 4933 - 4935]

22
[ 84-85-5 ]
[ 95715-87-0 ]
[ 925703-95-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: 4-methoxynaphth-1-ol With methylmagnesium chloride In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In dichloromethane at 0 - 20℃; for 15h;

Reference： [1]Rondot, Christophe; Retailleau, Pascal; Zhu, Jieping [Organic Letters, 2007, vol. 9, # 2, p. 247 - 250]

23
[ 84-85-5 ]
[ 54808-03-6 ]

Yield	Reaction Conditions	Operation in experiment
62%	With oxygen In toluene at 100℃; for 7h;
	Multi-step reaction with 3 steps 1: 99 percent / 1,4-benzoquinone / CH₂Cl₂ / 2 h / 20 °C 2: 96 percent / SnO₂ / CH₂Cl₂ / 19 h / 20 °C 3: 84 percent / 1,4-benzoquinone; O₂ / toluene / 3 h / 100 °C
	Multi-step reaction with 2 steps 1: 95 percent / activated charcoal; O₂ / acetonitrile / 16 h / 70 °C 2: 59 percent / CHCl₃ / 1 h / Irradiation

	Multi-step reaction with 4 steps 1: 95 percent / activated charcoal; O₂ / acetonitrile / 16 h / 70 °C 2: 99 percent / HNO₃ / H₂O / 0.25 h / 0 °C 3: 90 percent / CHCl₃ / 2 h / 23 °C / Photolysis 4: 91 percent / K₂CO₃ / dimethylformamide / 4 h / 23 °C
	Multi-step reaction with 2 steps 1: 75 percent / ZrO₂; O₂ / acetonitrile / 1.5 h / 70 °C 2: 59 percent / CHCl₃ / 1 h / Irradiation
	Multi-step reaction with 4 steps 1: 75 percent / ZrO₂; O₂ / acetonitrile / 1.5 h / 70 °C 2: 99 percent / HNO₃ / H₂O / 0.25 h / 0 °C 3: 90 percent / CHCl₃ / 2 h / 23 °C / Photolysis 4: 91 percent / K₂CO₃ / dimethylformamide / 4 h / 23 °C
	Multi-step reaction with 6 steps 1: Ag₂O / CHCl₃ 2: CHCl₃ 3: 91 percent / CHCl₃; acetone; diethyl ether / 0.17 h / -20 °C 4: 91 percent / pyridine/4-(dimethylamino)pyridine / 5 h / Ambient temperature 5: 86 percent / ammonium-cer(IV)-nitrate / acetonitrile; H₂O 6: 1 N NaOH/air / methanol
	Multi-step reaction with 7 steps 1: Ag₂O / CHCl₃ 2: CHCl₃ 3: 91 percent / CHCl₃; acetone; diethyl ether / 0.17 h / -20 °C 4: 91 percent / pyridine/4-(dimethylamino)pyridine / 5 h / Ambient temperature 5: 86 percent / ammonium-cer(IV)-nitrate / acetonitrile; H₂O 6: 1.) Na₂S₂O₄; 2.) 2 N NaOH / 1.) CHCl₃/ether/H₂O; 2.) CH₃OH, 5 min 7: air

Reference： [1]Takeya, Tetsuya; Kondo, Hiromu; Tomita, Kazuho; Okamoto, Iwao; Morita, Nobuyoshi; Tamura, Osamu [Heterocycles, 2007, vol. 74, # C, p. 961 - 968]
[2]Takeya, Tetsuya; Kondo, Hiromu; Otsuka, Tsuyoshi; Tomita, Kazuho; Okamoto, Iwao; Tamura, Osamu [Organic Letters, 2007, vol. 9, # 15, p. 2807 - 2810]
[3]Ogata, Tokutaro; Okamoto, Iwao; Kotani, Eiichi; Takeya, Tetsuya [Tetrahedron, 2004, vol. 60, # 18, p. 3941 - 3948]
[4]Ogata, Tokutaro; Okamoto, Iwao; Kotani, Eiichi; Takeya, Tetsuya [Tetrahedron, 2004, vol. 60, # 18, p. 3941 - 3948]
[5]Ogata, Tokutaro; Okamoto, Iwao; Kotani, Eiichi; Takeya, Tetsuya [Tetrahedron, 2004, vol. 60, # 18, p. 3941 - 3948]
[6]Ogata, Tokutaro; Okamoto, Iwao; Kotani, Eiichi; Takeya, Tetsuya [Tetrahedron, 2004, vol. 60, # 18, p. 3941 - 3948]
[7]Laatsch, Hartmut [Liebigs Annalen der Chemie, 1984, # 7, p. 1367 - 1381]
[8]Laatsch, Hartmut [Liebigs Annalen der Chemie, 1984, # 7, p. 1367 - 1381]

24
[ 769-54-0 ]
[ 84-85-5 ]
[ 130865-34-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In N,N-dimethyl-formamide;	EXAMPLE 2 3-(4-Methoxy-1-naphthyloxy)-4-nitropyridine-N-oxide To a solution of 4-methoxy-1-naphthol (8.87 g) in 50 ml of DMF was added sodium carbonate (7.8 g) portionwise, and after the addition was complete the mixture was stirred for 15 minutes. Then a solution of <strong>[769-54-0]3-fluoro-4-nitropyridine-N-oxide</strong> (8.0 g) in 50 ml DMF was added dropwise at room temperature. The reaction was then allowed to proceed for 4 hours at room temperature. The mixture was then poured into water and extracted with ethyl acetate. The organic layer was washed with NaCl (sat) and dried (anhy. MgSO4). After filtration, the solvent was evaporated to yield an oil which solidified on standing (31.0 g). This material was eluted with 10% ethyl acetate/DCM on silica gel columns via HPLC. The desired fractions were concentrated to yield a solid (14.2 g). Of this material 7.0 g was recrystallized from methanol to yield a solid, 2.6 g, m.p. 155-157 C. Analysis: Calculated for C16 H12 N2 O5: 61.54% C, 3.87% H, 8.97% N; Found: 61.49% C, 3.86% H, 8.95% N.

Reference： [1]Patent: US4931457,1990,A

25
[ 84-85-5 ]
[ 3282-30-2 ]
[ 1072840-83-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With dmap; triethylamine In dichloromethane Inert atmosphere;
	With dmap; triethylamine In dichloromethane at 20℃; for 7h;
	With triethylamine In dichloromethane at 20℃;

	With triethylamine In dichloromethane at 20℃; Inert atmosphere; Schlenk technique;
	With triethylamine In dichloromethane at 20℃;
	With triethylamine In dichloromethane at 20℃; Inert atmosphere; Schlenk technique;

Reference： [1]Quasdorf, Kyle W.; Tian, Xia; Garg, Neil K. [Journal of the American Chemical Society, 2008, vol. 130, # 44, p. 14422 - 14423]
[2]Ehle, Andrew R.; Zhou, Qi; Watson, Mary P. [Organic Letters, 2012, vol. 14, # 5, p. 1202 - 1205]
[3]Zarate, Cayetana; Martin, Ruben [Journal of the American Chemical Society, 2014, vol. 136, # 6, p. 2236 - 2239]
[4]Yang, Jia; Chen, Tieqiao; Han, Li-Biao [Journal of the American Chemical Society, 2015, vol. 137, # 5, p. 1782 - 1785]
[5]Yue, Huifeng; Guo, Lin; Liu, Xiangqian; Rueping, Magnus [Organic Letters, 2017, vol. 19, # 7, p. 1788 - 1791]
[6]Xi, Xiaoxiang; Chen, Tieqiao; Zhang, Ji-Shu; Han, Li-Biao [Chemical Communications, 2018, vol. 54, # 12, p. 1521 - 1524]

26
[ 84-85-5 ]
[ 556-82-1 ]
[ 20213-26-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	With o-tetrachloroquinone; tricarbonylcyclopentadienylmolybdenum(II) chloride In chlorobenzene at 150℃; for 1h; Inert atmosphere; Microwave irradiation;
60%	With iodine In chloroform for 2h; Reflux;	4.2.2 General procedure for the synthesis of chromans General procedure: In a 50 mL round bottom flask, prenyl alcohol (1.16 mmol) was mixed with chloroform (10 mL). To it, substituted phenol (4.0 equiv) and iodine (0.3 equiv) were added at room temperature. This reaction mixture was subjected to reflux with stirring for 4 h. It was then cooled to room temperature. Chloroform was directly washed with saturated solution of sodium thiosulphate followed by dilute sodium hydroxide solution. Finally chloroform layer was washed with water, dried over sodium sulfate and concentrated to furnish the crude product. This was then purified using 60-120 mesh silica gel column chromatography (hexanes/ethyl acetate) to give chroman.
60%	With iodine In chloroform for 2h; Reflux;	4.2.2. General procedure for the synthesis of chromans. General procedure: In a 50 mL round bottom flask, prenyl alcohol (1.16 mmol) was mixed with chloroform (10 mL). To it, substituted phenol (4.0 equiv) and iodine (0.3 equiv) were added at room temperature. This reaction mixture was subjected to reflux with stirring for 4 h. It was then cooled to room temperature. Chloroform was directly washed with saturated solution of sodium thiosulphate followed by dilute sodium hydroxide solution. Finally chloroform layer was washed with water, dried over sodium sulfate and concentrated to furnish the crude product. This was then purified using 60-120 mesh silica gel column chromatography (hexanes/ethyl acetate) to give chroman.

Reference： [1]Location in patent: scheme or table Yamamoto, Yoshihiko; Itonaga, Kouhei [Organic Letters, 2009, vol. 11, # 3, p. 717 - 720]
[2]Naik, Mayuri M.; Kamat, Durga P.; Tilve, Santosh G.; Kamat, Vijayendra P. [Tetrahedron, 2014, vol. 70, # 34, p. 5221 - 5233]
[3]Naik, Mayuri M.; Kamat, Durga P.; Tilve, Santosh G.; Kamat, Vijayendra P. [Tetrahedron, 2014, vol. 70, # 34, p. 5221 - 5233]

27
[ 84-85-5 ]
[ 24424-99-5 ]
[ 421555-84-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	With dmap; triethylamine In dichloromethane

Reference： [1]Quasdorf, Kyle W.; Riener, Michelle; Petrova, Krastina V.; Garg, Neil K. [Journal of the American Chemical Society, 2009, vol. 131, # 49, p. 17748 - 17749]

28
[ 84-85-5 ]
[ 88-10-8 ]
[ 1201594-02-6 ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: 4-methoxynaphth-1-ol With sodium hydride In 1,2-dimethoxyethane; mineral oil at 0 - 23℃; for 0.166667h; Stage #2: N,N-diethylcarbamyl chloride In 1,2-dimethoxyethane; mineral oil at 23℃; for 11h;
	Stage #1: 4-methoxynaphth-1-ol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: N,N-diethylcarbamyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃; for 11h;
	Stage #1: 4-methoxynaphth-1-ol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Stage #2: N,N-diethylcarbamyl chloride In tetrahydrofuran; mineral oil at 20℃;

Reference： [1]Quasdorf, Kyle W.; Riener, Michelle; Petrova, Krastina V.; Garg, Neil K. [Journal of the American Chemical Society, 2009, vol. 131, # 49, p. 17748 - 17749]
[2]Zhang, Juan; Zhang, Yun; Geng, Shasha; Chen, Shuo; Liu, Zhengli; Zeng, Xiaoqin; He, Yun; Feng, Zhang [Organic Letters, 2020, vol. 22, # 7, p. 2669 - 2674]
[3]Geng, Shasha; Zhang, Juan; Chen, Shuo; Liu, Zhengli; Zeng, Xiaoqin; He, Yun; Feng, Zhang [Organic Letters, 2020, vol. 22, # 14, p. 5582 - 5588]

29
[ 84-85-5 ]
[ 13360-57-1 ]
[ 1201594-33-3 ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: 4-methoxynaphth-1-ol With sodium hydride In 1,2-dimethoxyethane; mineral oil at 0 - 23℃; Inert atmosphere; Stage #2: dimethylamino sulfonyl chloride In 1,2-dimethoxyethane; mineral oil at 0 - 23℃; Inert atmosphere;
70%	Stage #1: 4-methoxynaphth-1-ol With sodium hydride In 1,2-dimethoxyethane; mineral oil at 0 - 23℃; for 0.166667h; Stage #2: dimethylamino sulfonyl chloride In 1,2-dimethoxyethane; mineral oil at 23℃; for 11h;

Reference： [1]Agrawal, Toolika; Cook, Silas P. [Organic Letters, 2013, vol. 15, # 1, p. 96 - 99]
[2]Quasdorf, Kyle W.; Riener, Michelle; Petrova, Krastina V.; Garg, Neil K. [Journal of the American Chemical Society, 2009, vol. 131, # 49, p. 17748 - 17749]

30
[ 84-85-5 ]
2-diazo-4-methoxy-1(2H)-naphthalenone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With 15-crown-5; 2-azido-1,3-dimethylimidazolinium chloride; triethylamine In tetrahydrofuran; acetonitrile at -20℃; for 1h;
73%	With 2-azido-1,3-dimethylimidazolinium chloride; triethylamine In tetrahydrofuran; acetonitrile at -20℃; for 1h; Inert atmosphere;	Typical Procedure for the Preparation of Diazonaphthoquinones by the Reaction of Naphthols with 2-Azide-1,3-dimethylimidazolinium Chloride (Method B, Table 3, Run 12) General procedure: To a solution of 2-chloro-1,3-dimethylimidazoliniumchloride 7 (228 mg, 1.35mmol) in acetonitrile (2 mL),sodium azide (99.4 mg, 1.5mmol) and 15-crown-5 ether (0.06ml, 0.3mmol) was added at 20°C and the mixture was stirred for 30min. 2-Naphthol 14a (130 mg, 0.90mmol) and triethylamine (0.25 mL, 1.8mmol) in THF (4 mL) was added to the mixture, which was stirred for 20min. The reaction was quenched with water, and organic materials were extracted three times with CH2Cl2. The combined extracts were washed with water and brine, and then, dried over anhydrous sodium sulfate. The solvent was removed in vacuo to afford crude compounds. The crude materials were purified by flash column chromatography (silica gel: hexane/ethyl acetate = 4/1) to give diazonaphthoquinone 1a in 87% yield.
	With 2-azido-1,3-dimethylimidazolinium chloride; triethylamine Inert atmosphere; regioselective reaction;

Reference： [1]Location in patent: experimental part Kitamura, Mitsuru; Tashiro, Norifumi; Sakata, Rie; Okauchi, Tatsuo [Synlett, 2010, # 16, p. 2503 - 2505]
[2]Kitamura, Mitsuru; Sakata, Rie; Tashiro, Norifumi; Ikegami, Azusa; Okauchi, Tatsuo [Bulletin of the Chemical Society of Japan, 2015, vol. 88, # 6, p. 824 - 833]
[3]Kitamura, Mitsuru; Kisanuki, Masato; Okauchi, Tatsuo [European Journal of Organic Chemistry, 2012, # 5, p. 905 - 907]

31
[ 84-85-5 ]
[ 13909-34-7 ]
[ 1264626-26-7 ]

Yield	Reaction Conditions	Operation in experiment
97%	With 4-((S)-(phenanthren-9-yloxy)((2R,4S,8R)-8-vinylquinuclidin-2-yl)methyl)quinolin-6-ol In toluene at 0℃; for 48h; optical yield given as %ee; enantioselective reaction;

Reference： [1]Liu, Guixia; Zhang, Shilei; Li, Hao; Zhang, Tangzhi; Wang, Wei [Organic Letters, 2011, vol. 13, # 5, p. 828 - 831]

32
[ 5724-81-2 ]
[ 84-85-5 ]
[ 1296674-14-0 ]

Yield	Reaction Conditions	Operation in experiment
66%	In dichloromethane at 20℃; regioselective reaction;
61%	In dichloromethane at 20℃; for 24h; Inert atmosphere;	General procedure for the synthesis of alpha-substituted pyrrolidines General procedure: Pyrrolidine (420 L, 5 mmol) and binuclear copper(II)-7-azaindole complex S1 [Cu] (1.2%, 22.7 mg,0.06 mmol) were stirred in a 5 mL pear-shaped flask at 50 °C and under an atmosphere of oxygen for 16 hours. The reaction mixture was cooled to room temperature, flushed with argon and diluted with anhydrous dichloromethane (2.5 mL) before adding the phenol or the naphthol (2.5 mmol). After stirring for 24 hours at room temperature, the crude reaction mixture was filtered over a plug of triethylamine-deactivated silica gel and the solvent was evaporated under vacuum. The crude reaction mixture was finally purified by flash chromatography over triethylamine-deactivated silica gel to afford the desired α-substituted pyrrolidine.

Reference： [1]Location in patent: experimental part Cimarelli, Cristina; Fratoni, Davide; Mazzanti, Andrea; Palmieri, Gianni [European Journal of Organic Chemistry, 2011, # 11, p. 2094 - 2100]
[2]Gérard, Phidéline; Evano, Gwilherm [Letters in Organic Chemistry, 2018, vol. 15, # 5, p. 359 - 364]

33
[ 84-85-5 ]
[ 4707-32-8 ]

Reference： [1]Bulletin of the Korean Chemical Society,2011,vol. 32,p. 153 - 156

34
[ 84-85-5 ]
[ 4707-32-8 ]
[ 4707-33-9 ]

Reference： [1]Bulletin of the Korean Chemical Society,2011,vol. 32,p. 153 - 156

35
[ 84-85-5 ]
[ 1867-38-5 ]
[ 1383732-30-6 ]

Yield	Reaction Conditions	Operation in experiment
89%	With piperidine In ethanol for 1h; Reflux;	2.1. Reaction of 4-methoxy-1-naphthol (1) with 2a,b General procedure: A solution of 4-methoxy-1-naphthol (1) (0.01 mmol) in EtOH (30 mL) was treated with α-cyano-p-chlorocinnamonitrile (2a) or ethyl α-cyano-p-chlorocinnamate (2b) (0.01 mmol) and piperidine (0.5 mL). The reaction mixture was heated until complete precipitation occurred (reaction times: 60 min for 2a; 120 min for 2b). The solid product which formed was collected by filtration and recrystallied from ethanol to give 3a,b. The physical and spectral data of compounds 3a,b are as follows: It should be added that spectra of 3a and 3b were recorded in THF in Table 1, as well as in the experimental part.
	With piperidine In ethanol

Reference： [1]Location in patent: experimental part Al-Sehemi, Abdullah G.; Irfan, Ahmad; El-Agrody, Ahmed M. [Journal of Molecular Structure, 2012, vol. 1018, p. 171 - 175]
[2]El-Agrody, Ahmed M.; Fouda, Ahmed M.; Al-Dies, Al-Anood M. [Medicinal Chemistry Research, 2014, vol. 23, # 6, p. 3187 - 3199]

36
[ 84-85-5 ]
[ 2286-35-3 ]
[ 1383732-32-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	With piperidine In ethanol for 2h; Reflux;	2.1. Reaction of 4-methoxy-1-naphthol (1) with 2a,b General procedure: A solution of 4-methoxy-1-naphthol (1) (0.01 mmol) in EtOH (30 mL) was treated with α-cyano-p-chlorocinnamonitrile (2a) or ethyl α-cyano-p-chlorocinnamate (2b) (0.01 mmol) and piperidine (0.5 mL). The reaction mixture was heated until complete precipitation occurred (reaction times: 60 min for 2a; 120 min for 2b). The solid product which formed was collected by filtration and recrystallied from ethanol to give 3a,b. The physical and spectral data of compounds 3a,b are as follows: It should be added that spectra of 3a and 3b were recorded in THF in Table 1, as well as in the experimental part.
	With piperidine In ethanol

Reference： [1]Location in patent: experimental part Al-Sehemi, Abdullah G.; Irfan, Ahmad; El-Agrody, Ahmed M. [Journal of Molecular Structure, 2012, vol. 1018, p. 171 - 175]
[2]El-Agrody, Ahmed M.; Fouda, Ahmed M.; Al-Dies, Al-Anood M. [Medicinal Chemistry Research, 2014, vol. 23, # 6, p. 3187 - 3199]

37
[ 84-85-5 ]
[ 1381932-41-7 ]
[ 1435914-10-5 ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium carbonate In toluene at 20℃; for 3h; regiospecific reaction;	19 General procedure for the synthesis of arenofurans 10, 11, and 13 General procedure: To a stirred solution of naphthol/phenol 9 (0.3 mmol) and K2CO3 (0.6 mmol, 2 equiv) in toluene (2 mL) was added MBH acetate 6 (0.4 mmol, 1.3 equiv) at room temperature. After completion of the reaction (monitored by TLC), the solvent was evaporated in vacuo and the crude residue was purified by silica gel column chromatography by gradient elution with ethyl acetate/petroleum ether (1:99 to 7:93).

Reference： [1]Kumar, Tarun; Mobin, Shaikh M.; Namboothiri, Irishi N.N. [Tetrahedron, 2013, vol. 69, # 24, p. 4964 - 4972]

38
[ 108-86-1 ]
[ 84-85-5 ]
[ 56013-54-8 ]

Yield	Reaction Conditions	Operation in experiment
20%	With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 40 - 45℃;	5.21 A general procedure for C-O coupling General procedure: Phenol (94mg, 1mmol) and bromobenzene (314mg, 2.0mmol) were added to a single necked flask containing DMSO (1mL) and resulted reaction mixture was stirred for 5min. After this potassium tert-butoxide (280mg, 2.5mmol) was added portion wise and stirring continued for 6-8h at 40-45°C. The progress of reaction was monitored by TLC. Upon completion of the reaction, mixture poured into water, and extracted four times with 20mL of ethyl acetate. The combined organic layer was dried over Na2SO4, and filtered. The solvent was removed in vacuo and the residue was purified by column chromatography (silica gel, eluent: hexane/ethyl acetate) to afford the coupling product.

Reference： [1]Kumar, Amit; Bhakuni, Bhagat Singh; Prasad, Ch. Durga; Kumar, Shailesh; Kumar, Sangit [Tetrahedron, 2013, vol. 69, # 26, p. 5383 - 5392]

39
[ 84-85-5 ]
[ 41978-69-2 ]
C₁₄H₁₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 2h;	[0506] 4-Methoxy-1-naphthol (12.5 g) was dissolved in 1-methyl-2-pyrrolidone (40 mL), potassium carbonate (11.9 g) and ethyl 2-bromopropanoate (15.6 g) were added thereto, and a reaction was carried out at 80° C. for 2 hours. A 1N HCl aqueous solution (120 mL) and ethyl acetate (100 mL) were added to the reaction mixture, a separation was carried out, the organic layer was concentrated, ethanol (25 mL), water (25 mL), and sodium hydroxide (5.7 g) were then added, and a reaction was carried out at 60° C. for 1 hour. The reaction mixture was poured into a 1N HCl aqueous solution (300 mL) and extracted with ethyl acetate, and the organic layer was dried with magnesium sulfate, filtered, and concentrated, thus giving a crude carboxylic acid (19 g).

Reference： [1]Current Patent Assignee: FUJIFILM HOLDINGS CORP. - US2013/171415, 2013, A1 Location in patent: Paragraph 0506

40
[ 25414-22-6 ]
[ 1609119-99-4 ]
[ 84-85-5 ]

Yield	Reaction Conditions	Operation in experiment
79%	With phenylmagnesium bromide In tetrahydrofuran at -78℃; for 0.166667h; Inert atmosphere;	A typical procedure for the aryne generation from ortho-sulfinylaryl triflate 1 General procedure: To a mixture of 2-(4-tolylsulfinyl)phenyl triflate (1a) (87.4 mg, 0.240 mmol) and 1,3-diphenylisobenzofuran (2) (54.1 mg, 0.200 mmol) dissolved in THF (2.5 mL) was slowly added phenylmagnesium bromide (1.05 M, THF solution, 0.343 mL, 0.360 mmol) at -78 °C. After stirring for 10 min at the same temperature, to the mixture was added an aqueous phosphate buffer solution (pH 7, 10 mL). The mixture was extracted with EtOAc (10 mL × 3), and the combined organic extract was washed with brine (5 mL), dried (Na2SO4), and after filtration, the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (silica-gel 10 g, n-hexane/EtOAc = 50/1) to give 9,10-diphenyl-9,10-dihydro-9,10-epoxyanthracene (3a) (69.3 mg, 0.200 mmol, quant.) as a colorless solid.

Reference： [1]Yoshida, Suguru; Uchida, Keisuke; Hosoya, Takamitsu [Chemistry Letters, 2014, vol. 43, # 1, p. 116 - 118]

41
[ 84-85-5 ]
[ 104-88-1 ]
[ 109-77-3 ]
[ 1383732-30-6 ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine In ethanol
	With piperidine In ethanol for 1h; Reflux;
	With piperidine In ethanol at 140℃; for 0.0333333h; Microwave irradiation;	2.2.1. General procedure for synthesis of 4H-benzo[h]chromenederivatives (4a-m) General procedure: A reaction mixture of 4-methoxy-1-naphthol 1 (0.01 mol),different aromatic aldehydes 2a-m (0.01 mol), malononitrile 3(0.01 mol), and piperidine (0.5 mL) in ethanol (30 mL) was heatedunder microwave irradiation conditions for 2 min at 140 C. Afterthe completion of the reaction, the reaction mixture was cooled toroom temperature, and the precipitated solid was filtered off,washed with MeOH, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are asfollows.

Reference： [1]El-Agrody, Ahmed M.; Fouda, Ahmed M.; Al-Dies, Al-Anood M. [Medicinal Chemistry Research, 2014, vol. 23, # 6, p. 3187 - 3199]
[2]Okasha, Rawda M.; Albalawi, Fawzia F.; Afifi, Tarek H.; Fouda, Ahmed M.; Al-Dies, Al-Anood M.; El-Agrody, Ahmed M. [Molecules, 2016, vol. 21, # 11]
[3]Ahmed, Hany E.A.; El-Nassag, Mohammed A.A.; Hassan, Ahmed H.; Mohamed, Hany M.; Halawa, Ahmed H.; Okasha, Rawda M.; Ihmaid, Saleh; Abd El-Gilil, Shimaa Mohamed; Khattab, Essam S.A.E.H.; Fouda, Ahmed M.; El-Agrody, Ahmed M.; Aljuhani, Ateyatallah; Afifi, Tarek H. [Journal of Molecular Structure, 2019, vol. 1186, p. 212 - 223]

42
[ 590-93-2 ]
[ 84-85-5 ]
4-methoxynaphthyl 2-butynoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: 2-Butynoic acid With diisopropyl-carbodiimide In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 4-methoxynaphth-1-ol With dmap In dichloromethane at 20℃; Inert atmosphere;
56%	Stage #1: 2-Butynoic acid With diisopropyl-carbodiimide In dichloromethane at 0℃; for 0.5h; Schlenk technique; Stage #2: 4-methoxynaphth-1-ol With dmap In dichloromethane at 0℃; Schlenk technique;

Reference： [1]Bibal, Brigitte; Buffière, Sonia; Cao, Zhen; Nlate, Sylvain; Oda, Reiko; Pouget, Emilie; Scalabre, Antoine [Chemistry - A European Journal, 2021, vol. 27, # 1, p. 427 - 433]
[2]Aparece, Mark D.; Vadola, Paul A. [Organic Letters, 2014, vol. 16, # 22, p. 6008 - 6011]

43
[ 84-85-5 ]
[ 2483-46-7 ]
(S)-4-methoxynaphthalen-1-yl 2,6-bis((tert-butoxy-carbonyl)amino)hexanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 68h; Inert atmosphere;	5 4.2.4 General synthetic procedure for compounds 14-18 General procedure: N2,N6-Bis(tert-butoxycarbonyl)-l-lysine (8) (2 equiv) was dissolved in anhydrous dichloromethane (10 mL/mmol of 8). Triethylamine (2 equiv) was added, followed by the appropriate alcohol (1 equiv). The mixture was stirred for a couple of minutes under nitrogen atmosphere and then cooled to 0 °C. Hydroxybenzotriazole (HOBt, 2 equiv) and dicyclohexyl carbodiimide (DCC, 2 equiv) were added simultaneously. The reaction mixture was stirred at room temperature for the times indicated below. The precipitate was removed by filtration and discarded. The filtrate was washed successively with NaHCO3 aq (satd), then NaHSO4 aq (150 g/L), NaHCO3 aq (satd) and finally with water. The organic phase was dried over MgSO4 and the solvent was removed under reduced pressure. The resulting crude product was purified by flash chromatography (pentane/ethyl acetate 1:1). 4.2.4.5 (S)-4-Methoxynaphthalen-1-yl 2,6-bis((tert-butoxy-carbonyl)amino)hexanoate (18) Prepared according to the general procedure from 8 (2.00 g, 5.77 mmol) and 4-methoxynaphthalen-1-ol (503 mg, 2.89 mmol) yielding 18 (1.25 g, 2.49 mmol, 86%) after 68 h of reaction time as a pale red, gel-like solid; 1H NMR (CDCl3, 400.1 MHz): δ = 8.24-8.27 (m, 1H), 7.79 (d, J = 7.9 Hz, 1H), 7.47-7.55 (m, 2H), 7.13 (d, J = 8.5 Hz, 1H), 6.75 (d, J = 8.3 Hz, 1H), 5.27 (br s, 1H), 4.64-4.65 (m, 1H), 3.99 (s, 3H), 3.17 (s, 2H), 2.08-2.16 (m, 1H), 1.70-1.85 (m, 1H), 1.53-1.63 (m, 4H), 1.48 (s, 9H), 1.44 (m, 9H) ppm; 13C NMR (CDCl3, 100.6 MHz): δ = 172.0, 171.1, 156.1, 155.7, 153.6, 139.7, 127.3, 127.1, 126.2, 125.8, 122.3, 120.0, 117.4, 80.1, 55.7, 53.7, 32.2, 29.7, 28.4, 28.3, 21.0 ppm; HRMS (ESI): m/z calcd for C27H38N2NaO7+: 525.2577; found: 525.2574 [M+Na]+.

Reference： [1]Zuravka, Ivonne; Roesmann, Rolf; Sosic, Alice; Göttlich, Richard; Gatto, Barbara [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 6, p. 1241 - 1250]

44
[ 358-23-6 ]
[ 84-85-5 ]
[ 112183-02-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With 4-dimethylaminopyridine; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 6h;	To a stirred solution of 4-methoxy-1-naphthol (S1, 5.23 g, 30.0 mmol) and N,N-dimethyl-4-aminopyridine (0.740 g, 6.00 mmol) in CH2Cl2 (150 mL) was added i-Pr2NEt (7.90 mL, 45.0 mmol) and Tf2O (7.60 mL, 45.0 mmol) at 0 °C. The reaction mixture was allowed to room temperature. After stirring for 6 h, the resulting mixture was poured into H2O and extracted with CHCl3 (twice). The combined organic layers were washed with brine and dried over anhydrous MgSO4. The solvents were removed in vacuo. The residue was purified by flash column chromatography on silica gel (eluent: hexane-EtOAc = 50:1 to 30:1) to give S2 (9.17 g, 30.0 mmol, >99%yield).
	Stage #1: 4-methoxynaphth-1-ol With pyridine In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at 20℃; Inert atmosphere;
	With triethylamine In dichloromethane at 0 - 20℃;	2. General Procedure for Synthesis of Aryl Triflates General procedure: To a solution of phenols (1.0 equiv, 0.5 M) in CH2Cl2 was added Et3N (2 equiv) at 0 °C. The mixture was allowed to stirred at 0 °C for 5 min followed by dropwise addition of Tf2O (1.5 equiv). The reaction mixture was warmed to room temperature and stirred until full consumption of starting materials (monitored by TLC). The resulting mixture was concentrated under reduced pressure and purified by flash column chromatography.

Reference： [1]Uyanik, Muhammet; Sasakura, Niiha; Kaneko, Erina; Ohori, Kento; Ishihara, Kazuaki [Chemistry Letters, 2015, vol. 44, # 2, p. 179 - 181]
[2]Zhang, Liangwei; Liu, Long; Huang, Tianzeng; Dong, Qizhi; Chen, Tieqiao; Chen, Tieqiao [Organometallics, 2020, vol. 39, # 11, p. 2189 - 2196]
[3]Xu, Tianhao; Zhou, Xiangbing; Han, Yuhui; Zhang, Liangwei; Liu, Long; Huang, Tianzeng; Li, Chunya; Tang, Zhi; Wan, Shungang; Chen, Tieqiao [Tetrahedron Letters, 2022, vol. 97]

45
[ 84-85-5 ]
[ 73845-02-0 ]
C₂₅H₂₂N₂O₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With C₆₀H₆₈N₂O₁₀; copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 25℃; Inert atmosphere; Molecular sieve; enantioselective reaction;	2.4. General procedure for asymmetric Friedel-Crafts reaction of addition of 1-naphthol to N-sulfonyl aldimine General procedure: Under an N2 atmosphere, Cu(OTf)2 (0.005 mmol) and (1R, 2S)-L2 (0.00275 mmol) were dissolved in DCM (2 mL) The solution was stirred at room temperature for 2 h, then 4 Å molecular sieves (100 mg) were added and stirred for another 10 min. Next, tosyl aldimine (0.20 mmol) and 1-naphthol or 2-naphthol (0.4 mmol) were added, and the reaction mixture was stirred at 25 °C. After the reaction was completed, the solvent was removed under reduce pressure and the residue was purified by column chromatography on silica gel eluted with ethyl acetate/petroleum ether (1:9) to afford the desired product as white powder.

Reference： [1]Kumari, Prathibha; Jakhar, Ajay; Khan, Noor-Ul H.; Tak, Rajkumar; Kureshy, Rukhsana I.; Abdi, Sayed H.R.; Bajaj, Hari C. [Catalysis Communications, 2015, vol. 69, p. 138 - 142]

46
[ 67-52-7 ]
[ 84-85-5 ]
[ 91-56-5 ]
5-methoxy-spiro[benzo[7,8]chromeno[2,3-d]pyrimidin-3',7-indoline]-2',8,10-[1'H,9H,11H]-trione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With [HMIm][HSO₄] immobilized Fe₃O₄ on MCM-41-SO₃H nanoparticles In neat (no solvent) at 100℃; for 0.25h;	15 5-methoxy-spiro[benzo[7,8]chromeno[2,3-d]pyrimidin-3',7-indoline]-2',8,10-[1'H,9H,11H]-trione (6d) General procedure: A mixture of α or β-naphtol (1 mmol), isatin derivatives (1 mmol),barbituric acid (1.2 mmol), and Fe3O4MCM-41-SO3H[HMIm][HSO4](0.08 g) was stirred at 100 °C under solvent-free conditions. Thereaction products were monitored using thin-layer chromatography(TLC). After completion of the reaction, magnetic nanocompositeswere separated by a magnet (1.4 T), and the reaction mixture filteredoff. Then, 5 mL distilled waterwas added into the beaker and the obtainedprecipitatewas filtered off. Finally, the crude productswere recrystallizedby ethanol to give pure products.
90%	With sublimated aluminum chloride supported on nanosilica-magnetite In ethanol for 4h; Reflux;	General procedure for synthesis ofspiro[benzochromeno[2,3-d]pyrimidin-indolines] 4a-o General procedure: In a round bottomed flask equipped with a magnetite barand condenser, a mixture of naphthols 1a-e (1mmol), isatins2a-f (1mmol), and barbitoric acids 3a-c (1mmol) in the presenceof AlCl3nano Fe3O4-SiO2 (0.02 g) and ethanol (5mL)refluxed until the completion monitored by TLC (n-hexan/ethylacetate eluent, 4:1). After completion of the reaction thecatalyst was separated from reaction mixture using a strongmagnet. The separated catalyst was washed with ethanol(10mL). Evaporation of the solvent in air followed by furtherpurification by PLC afforded the pure products 4a-o.

Reference： [1]Kefayati, Hassan; Kohankar, Alireza Mehtar; Ramzanzadeh, Nasim; Shariati, Shahab; Bazargard, Samaneh Jirsaray [Journal of Molecular Liquids, 2015, vol. 209, p. 617 - 624]
[2]Nikoofar, Kobra; Arian, Zahra; Djahaniani, Hoorieh [Inorganic and Nano-Metal Chemistry, 2022, vol. 52, # 3, p. 365 - 374]

47
[ 67-52-7 ]
[ 84-85-5 ]
[ 1217-89-6 ]
1'-benzyl-5-methoxy-spiro[benzo[7,8]chromeno[2,3-d]pyrimidin-3',7-indoline]-2',8,10-[9H,11H]trione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With [HMIm][HSO₄] immobilized Fe₃O₄ on MCM-41-SO₃H nanoparticles In neat (no solvent) at 100℃; for 0.5h;	16 1′-Benzyl-5-Methoxy-spiro[benzo[7,8]chromeno[2,3-d]pyrimidin-3′,7-indoline]-2′,8,10-[9H,11H]trione (6e) General procedure: A mixture of α or β-naphtol (1 mmol), isatin derivatives (1 mmol),barbituric acid (1.2 mmol), and Fe3O4MCM-41-SO3H[HMIm][HSO4](0.08 g) was stirred at 100 °C under solvent-free conditions. Thereaction products were monitored using thin-layer chromatography(TLC). After completion of the reaction, magnetic nanocompositeswere separated by a magnet (1.4 T), and the reaction mixture filteredoff. Then, 5 mL distilled waterwas added into the beaker and the obtainedprecipitatewas filtered off. Finally, the crude productswere recrystallizedby ethanol to give pure products.
84%	With sublimated aluminum chloride supported on nanosilica-magnetite In ethanol for 5h; Reflux;	General procedure for synthesis ofspiro[benzochromeno[2,3-d]pyrimidin-indolines] 4a-o General procedure: In a round bottomed flask equipped with a magnetite barand condenser, a mixture of naphthols 1a-e (1mmol), isatins2a-f (1mmol), and barbitoric acids 3a-c (1mmol) in the presenceof AlCl3nano Fe3O4-SiO2 (0.02 g) and ethanol (5mL)refluxed until the completion monitored by TLC (n-hexan/ethylacetate eluent, 4:1). After completion of the reaction thecatalyst was separated from reaction mixture using a strongmagnet. The separated catalyst was washed with ethanol(10mL). Evaporation of the solvent in air followed by furtherpurification by PLC afforded the pure products 4a-o.

Reference： [1]Kefayati, Hassan; Kohankar, Alireza Mehtar; Ramzanzadeh, Nasim; Shariati, Shahab; Bazargard, Samaneh Jirsaray [Journal of Molecular Liquids, 2015, vol. 209, p. 617 - 624]
[2]Nikoofar, Kobra; Arian, Zahra; Djahaniani, Hoorieh [Inorganic and Nano-Metal Chemistry, 2022, vol. 52, # 3, p. 365 - 374]

48
[ 84-85-5 ]
[ 1414889-30-7 ]
(R)-4-(1-hydroxy-4-methoxynaphthalen-2-yl)-1-(4-methoxybenzyl)-4,6-bis(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With C₃₇H₃₄N₄O₃ In chloroform at 20℃; for 1h; Inert atmosphere; enantioselective reaction;

Reference： [1]Zhou, Ding; Huang, Zheng; Yu, Xueting; Wang, Youxin; Li, Jian; Wang, Wei; Xie, Hexin [Organic Letters, 2015, vol. 17, # 22, p. 5554 - 5557]

49
[ 84-85-5 ]
C₁₀H₄F₆N₂O [ No CAS ]
(R)-4-(1-hydroxy-4-methoxynaphthalen-2-yl)-4,6-bis(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With C₃₇H₃₄N₄O₃ In chloroform at 20℃; for 2h; Inert atmosphere; enantioselective reaction;

Reference： [1]Zhou, Ding; Huang, Zheng; Yu, Xueting; Wang, Youxin; Li, Jian; Wang, Wei; Xie, Hexin [Organic Letters, 2015, vol. 17, # 22, p. 5554 - 5557]

50
[ 84-85-5 ]
[ 497235-37-7 ]
(R)-6-chloro-4-(1-hydroxy-4-methoxynaphthalen-2-yl)-1-(4-methoxybenzyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With C₃₇H₃₄N₄O₃ In chloroform at 20℃; for 2h; Inert atmosphere; enantioselective reaction;

Reference： [1]Zhou, Ding; Huang, Zheng; Yu, Xueting; Wang, Youxin; Li, Jian; Wang, Wei; Xie, Hexin [Organic Letters, 2015, vol. 17, # 22, p. 5554 - 5557]

51
[ 84-85-5 ]
[ 459-57-4 ]
[ 109-77-3 ]
2-amino-4-(4-fluorophenyl)-6-methoxy-4H-benzo[h]chromene-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine In ethanol for 1h; Reflux;
	With piperidine In ethanol for 1h; Reflux;
	With piperidine In ethanol at 140℃; for 0.0333333h; Microwave irradiation;	2.2.1. General procedure for synthesis of 4H-benzo[h]chromenederivatives (4a-m) General procedure: A reaction mixture of 4-methoxy-1-naphthol 1 (0.01 mol),different aromatic aldehydes 2a-m (0.01 mol), malononitrile 3(0.01 mol), and piperidine (0.5 mL) in ethanol (30 mL) was heatedunder microwave irradiation conditions for 2 min at 140 C. Afterthe completion of the reaction, the reaction mixture was cooled toroom temperature, and the precipitated solid was filtered off,washed with MeOH, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are asfollows.

Reference： [1]Halawa, Ahmed H.; Fouda, Ahmed M.; Al-Dies, Al-Anood M.; El-Agrody, Ahmed M. [Letters in drug design and discovery, 2016, vol. 13, # 1, p. 77 - 88]
[2]Okasha, Rawda M.; Albalawi, Fawzia F.; Afifi, Tarek H.; Fouda, Ahmed M.; Al-Dies, Al-Anood M.; El-Agrody, Ahmed M. [Molecules, 2016, vol. 21, # 11]
[3]Ahmed, Hany E.A.; El-Nassag, Mohammed A.A.; Hassan, Ahmed H.; Mohamed, Hany M.; Halawa, Ahmed H.; Okasha, Rawda M.; Ihmaid, Saleh; Abd El-Gilil, Shimaa Mohamed; Khattab, Essam S.A.E.H.; Fouda, Ahmed M.; El-Agrody, Ahmed M.; Aljuhani, Ateyatallah; Afifi, Tarek H. [Journal of Molecular Structure, 2019, vol. 1186, p. 212 - 223]

52
[ 84-85-5 ]
[ 91-56-5 ]
[ 504-02-9 ]
5-methoxy-10,11-dihydrospiro[benzo[c]xanthene-7,3'-indoline]-2',8(9H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With Fe₃O₄(at)MCM-41-SO₃H(at)1-methylimidazolium hydrogen sulfate In neat (no solvent) at 100℃; for 0.583333h;	4.10 2.3.1. Method A General procedure: A mixture of α or β-naphthol (1 mmol), isatin derivatives (1 mmol), cyclic 1,3-dicabonyls (1.2 mmol), and Fe3O4MCM-41-SO3H[HMIm][HSO4] (0.08 g) was stirred at 100 °C under solvent-free conditions. The reaction products were monitored using thin-layer chromatography (TLC). After completion of the reaction, magnetic nanocomposites were separated by a magnet (1.4 T), and the reaction mixture filtered off. Then, 5 mL distilled water was added into the beaker and the obtained precipitate was filtered off. Finally, the crude products were recrystallized by ethanol to give pure products.

Reference： [1]Kefayati, Hassan; Bazargard, Samaneh Jirsaray; Vejdansefat, Parisa; Shariati, Shahab; Kohankar, Alireza Mehtar [Dyes and Pigments, 2016, vol. 125, p. 309 - 315]

53
[ 84-85-5 ]
[ 91-56-5 ]
[ 126-81-8 ]
5-methoxy-10,10-dimethyl-10,11-dihydrospiro[benzo[c]xanthene-7,3'-indoline]-2',8(9H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With Fe₃O₄(at)MCM-41-SO₃H(at)1-methylimidazolium hydrogen sulfate In neat (no solvent) at 100℃; for 0.583333h;	4.9 2.3.1. Method A General procedure: A mixture of α or β-naphthol (1 mmol), isatin derivatives (1 mmol), cyclic 1,3-dicabonyls (1.2 mmol), and Fe3O4MCM-41-SO3H[HMIm][HSO4] (0.08 g) was stirred at 100 °C under solvent-free conditions. The reaction products were monitored using thin-layer chromatography (TLC). After completion of the reaction, magnetic nanocomposites were separated by a magnet (1.4 T), and the reaction mixture filtered off. Then, 5 mL distilled water was added into the beaker and the obtained precipitate was filtered off. Finally, the crude products were recrystallized by ethanol to give pure products.

Reference： [1]Kefayati, Hassan; Bazargard, Samaneh Jirsaray; Vejdansefat, Parisa; Shariati, Shahab; Kohankar, Alireza Mehtar [Dyes and Pigments, 2016, vol. 125, p. 309 - 315]

54
[ 84-85-5 ]
[ 107-30-2 ]
1-methoxy-4-(methoxymethoxy)-naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 4-methoxynaphth-1-ol With sodium hydride In N,N-dimethyl-formamide at 0℃; Inert atmosphere; Schlenk technique; Stage #2: chloromethyl methyl ether In dichloromethane; N,N-dimethyl-formamide for 4h; Inert atmosphere; Schlenk technique;
	With sodium hydride In diethyl ether; N,N-dimethyl-formamide at 0℃;

Reference： [1]Wu, Bo; Gao, Xiang; Yan, Zhong; Chen, Mu-Wang; Zhou, Yong-Gui [Organic Letters, 2015, vol. 17, # 24, p. 6134 - 6137]
[2]Chen, Ping; Wang, Kai; Guo, Wengang; Liu, Xianghui; Liu, Yan; Li, Can [Angewandte Chemie - International Edition, 2017, vol. 56, # 13, p. 3689 - 3693][Angew. Chem., 2017, vol. 129, # 13, p. 3743 - 3747,5]

55
[ 31928-44-6 ]
[ 84-85-5 ]
C₁₇H₁₁ClO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With palladium diacetate; caesium carbonate; triphenylphosphine; In N,N-dimethyl-formamide; at 140℃; for 24h;	<strong>[31928-44-6]2-bromo-4-chloro-1-iodo-benzene</strong>, 3.17 g (10 mmol), 4- methoxy-1-naphthol 1.92 g (11 mmol), palladium acetateAgent 0.112 g (0.5 mmol), triphenylphosphine 0.651 g (2.0 mmol) of cesium carbonate and 13 g (40 mmol) of DMF in 60 mLWas dissolved, and stirred for 24 hours at 140 , then added to 60 mL water cooled to room temperature three times with ethyl ether, 60 mL AdditionIt was exported. Dry the organic layer obtained therefrom by magnesium sulfate, and evaporation of the solvents the obtained residue was purified by silica gelPurified by column chromatography to obtain intermediate I-7 1.64 g (yield 58%). The resulting compound via LC-MSConfirmed.

Reference： [1]Patent: KR2015/109522,2015,A .Location in patent: Paragraph 0410-0413

56
[ 84-85-5 ]
[ 583-55-1 ]
4-methoxybenzo[b]naphtho[1,8-de]pyran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With palladium diacetate; caesium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 140℃; for 15h;	1 synthesis of intermediate 1-2 6.1 g of Intermediate 1-1 was dissolved in 230 ml, of DMF, and then, 252 mg of Pd(OAc)2, 320 mg of PPh3, 23 g of CsCO3, and 1-bromo-2-iodobenzene were added thereto, and the mixture was refluxed at a temperature of 140° C. while stirring. After 15 hours, the temperature was lowered to at room temperature, and 70 mL of water was added thereto to stop the reaction. Ethyl acetate was used to perform an extraction process thereon three times, and then, an organic solution was dried and concentrated by using anhydrous magnesium sulfate, and the result was separation-purified by using silca gel column chromatography to obtain Intermediate 1-2 (4.48 g, 67%).

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - KR2015/29430, 2015, A Location in patent: Paragraph 0382; 0386-0387

57
[ 84-85-5 ]
[ 1122-91-4 ]
[ 109-77-3 ]
2-amino-6-methoxy-4-(4-bromophenyl)-4H-benzo[h]chromene-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine In ethanol for 1h; Reflux;
	With piperidine In ethanol at 140℃; for 0.0333333h; Microwave irradiation;	2.2.1. General procedure for synthesis of 4H-benzo[h]chromenederivatives (4a-m) General procedure: A reaction mixture of 4-methoxy-1-naphthol 1 (0.01 mol),different aromatic aldehydes 2a-m (0.01 mol), malononitrile 3(0.01 mol), and piperidine (0.5 mL) in ethanol (30 mL) was heatedunder microwave irradiation conditions for 2 min at 140 C. Afterthe completion of the reaction, the reaction mixture was cooled toroom temperature, and the precipitated solid was filtered off,washed with MeOH, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are asfollows.

Reference： [1]Okasha, Rawda M.; Albalawi, Fawzia F.; Afifi, Tarek H.; Fouda, Ahmed M.; Al-Dies, Al-Anood M.; El-Agrody, Ahmed M. [Molecules, 2016, vol. 21, # 11]
[2]Ahmed, Hany E.A.; El-Nassag, Mohammed A.A.; Hassan, Ahmed H.; Mohamed, Hany M.; Halawa, Ahmed H.; Okasha, Rawda M.; Ihmaid, Saleh; Abd El-Gilil, Shimaa Mohamed; Khattab, Essam S.A.E.H.; Fouda, Ahmed M.; El-Agrody, Ahmed M.; Aljuhani, Ateyatallah; Afifi, Tarek H. [Journal of Molecular Structure, 2019, vol. 1186, p. 212 - 223]

58
[ 84-85-5 ]
[ 1075-06-5 ]
(R)-2-hydroxy-2-(1-hydroxy-4-methoxynaphthalen-2-yl)-1-phenylethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea In tert-butyl methyl ether; toluene at 20℃; for 24h; Inert atmosphere; enantioselective reaction;

Reference： [1]Vila, Carlos; Quintero, Lucia; Blay, Gonzalo; Muñoz, M. Carmen; Pedro, José R. [Organic Letters, 2016, vol. 18, # 21, p. 5652 - 5655]

59
[ 84-85-5 ]
[ 123-11-5 ]
[ 109-77-3 ]
2-amino-4-(4-methoxyphenyl)-6-methoxy-4H-benzo[h]chromene-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With piperidine In ethanol at 140℃; for 0.0333333h; Microwave irradiation;	2-Amino-4-(4-methoxyphenyl)-6-methoxy-4H-benzo[h]chromene-3-carbonitrile (4) A reaction mixture of 4-methoxy-1-naphthol (1, 1.74 g, 0.01 mol), 4-methoxybenzaldehyde (2, 1.36 g, 0.01 mol), malononitrile (3, 0.66 g, 0.01 mol) and piperidine (0.5 mL) in absolute ethanol (30 mL) was heated under microwave irradiation conditions for 2 min. at 140 °C. After the completion of the reaction, the mixture was cooled at room temperature and the precipitated solid was filtered off, washed with methanol and recrystallized from ethanol to give the desired compound 4 as a colorless solid, yield: 87%, m.p. 180-181 °C; IR (KBr, cm-1): 3443, 3332, 3207 (NH2), 3079, 3029 (CH-arom.), 2995, 2895 (CH-aliph.), 2193 (CN); 1H-NMR (DMSO-d6, δ, ppm); 3.72 (s, 3H, OCH3), 3.81 (s, 3H, OCH3), 4.80 (s, 1H, H-4), 7.07 (bs, 2H, NH2, canceled by D2O), 6.52-8.11 (m, 9H, Ar-H); 13C-NMR (DMSO-d6, δ, ppm); 40.70 (C-4), 54.96 (CH3), 55.64 (CH3), 56.43 (C-3), 103.44 (C-5), 114.00 (Ar-C), 118.09 (CN), 121.61 (C-4a), 123.66 (C-10), 124.33 (C-7), 126.10 (C-8), 127.17 (C-6a), 128.30 (C-9), 128.56 (C-10a), 128.77 (Ar-C), 136.74 (Ar-C), 137.64 (C-10b), 151.10 (C-6), 158.12 (Ar-C), 160.25 (C-2); its MS (m/z), 358 (M+, 13.92) with a base peak at 251 (100); C22H18N2O3 (358.39); calcd. % C: 73.73, % H: 5.06, % N: 7.82; found; % C: 73.79, % H: 5.11,% N: 7.89.

Reference： [1]Okasha, Rawda M.; Alblewi, Fawzia F.; Afifi, Tarek H.; Naqvi, Arshi; Fouda, Ahmed M.; Al-Dies, Al-Anood M.; El-Agrody, Ahmed M.; Belmont, Philippe; Bunce, Richard A. [Molecules, 2017, vol. 22, # 3]

60
[ 84-85-5 ]
[ 123-11-5 ]
[ 105-56-6 ]
ethyl 2-amino-4-(4-methoxyphenyl)-6-methoxy-4H-benzo[h]chromene-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With piperidine In ethanol at 140℃; for 0.0333333h; Microwave irradiation;	Ethyl 2-amino-4-(4-methoxyphenyl)-6-methoxy-4H-benzo[h]chromene-3-carboxylate (6) A reaction mixture of 4-methoxy-1-naphthol (1, 1.74 g, 0.01 mol), 4-methoxybenzaldehyde (2, 1.36 g, 0.01 mol), ethyl cyanoacetate (5, 1.13 g, 0.01 mol) and piperidine (0.5 mL) in absolute ethanol (30 mL) was heated under microwave irradiation conditions for 2 min. at 140 °C. After the completion of the reaction, the mixture was cooled at room temperature and the precipitated solid was filtered off, washed with methanol and recrystallized from ethanol to give the desired compound 6 as a colorless solid, yield: 72%, m.p. 159-60 °C; IR (KBr, cm-1): 3414, 3300 (NH2), 3014 (CH-arom.), 2997, 2963, 2875 (CH-aliph.), 1682 (CO); 1H-NMR (DMSO-d6, δ, ppm); 1.12 (t, 3H, CH3, J = 7.1 Hz), 3.77 (s, 3H, OCH3), 3.91 (s, 3H, OCH3), 4.11 (q, 2H, CH2, J = 7.1 Hz), 4.99 (s, 1H, H-4), 7.76 (bs, 2H, NH2), 6.45-8.30 (m, 9H, Ar-H); 13C-NMR(DMSO-d6, δ, ppm); 14.31 (CH3), 40.11 (C-4), 55.43 (CH3), 55.63 (CH3), 58.60 (CH2), 99.78 (C-3), 103.36(C-5), 114.89 (Ar-C), 115.18 (CN), 121.98 (C-4a), 122.61 (C-10), 122.97 (C-7), 124.78 (C-8), 126.59 (C-6a), 127.81, (C-9), 128.52 (C-10a), 130.54 (Ar-C), 142.17 (C-10b), 142.61 (Ar-C), 148.69 (C-6), 151.75 (Ar-C), 161.60 (C-2); its MS (m/z), 405 (M+, 29.33) with a base peak at 299 (100); C24H23NO5 (405.44); calcd.% C: 71.10, % H: 5.72, % N: 3.45; found; % C: 71.15, % H: 5.73, % N: 3.49.

Reference： [1]Okasha, Rawda M.; Alblewi, Fawzia F.; Afifi, Tarek H.; Naqvi, Arshi; Fouda, Ahmed M.; Al-Dies, Al-Anood M.; El-Agrody, Ahmed M.; Belmont, Philippe; Bunce, Richard A. [Molecules, 2017, vol. 22, # 3]

61
[ 84-85-5 ]
[ 1835-65-0 ]
3,4,6-trifluoro-5-((4-methoxynaphthalen-1-yl)oxy)phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80.1%	With lithium hydroxide monohydrate; In dimethyl sulfoxide; at 25℃; for 24.5h;	Toamixtureof5mmol of <strong>[1835-65-0]tetrafluorophthalonitrile</strong> (1.2 g,5mmol) and5mmol of 4-Methoxy-1-naphthol (0.87 g, 5 mmol) in 50 ml of DMSO at ambient temperature was added 5 mmolof lithium hydroxide monohydrate (0.21 g, 5 mmol) within 0.5 h. The mixture was stirred for24 h at same temperature and then it was poured to 100ml of water. Then extracted with chloroform(2 × 100 mL), washed with water (1 × 100 mL) and brine (1 × 100 mL) solution anddried over Na2SO4. The solvent was removed under reduced pressure. The resulting residuewas purified by silica-gel column chromatography using Benzene:Hexane (8:2) as an eluent toobtain compound 3 (1.41 g, 80.1percent) as a yellow solid. 1H NMR (600MHz, CDCl3 ppm) delta 7.94(d, J = 8.2 Hz, 1H), 7.43 (d, J = 8.2 Hz, 1H), 7.30-7.26 (m, 1H), 7.19-7.15 (m, 1H), 6.45 (d,J = 8.3 Hz, 1H), 6.36 (d, J = 8.3 Hz, 1H). 13C NMR (125 MHz, CDCl3, ppm) delta 155.7, 153.9,152.6, 146.1, 143.5, 128.5, 127.4, 126.7, 126.2, 125.4, 122.6, 122.0, 121.1, 120.6, 109.8, 109.1,102.2, 101.9, 55.8. IR (KBr tablet) numax/cm?1: 3010, 2940, 2236, 1633, 1597, 1386, 1289, 1152,1042, 978, 760. MALDI-TOF-MS: m/z calcd for C19H9F3N2O2, 354; found 355 [M + H+]+.

Reference： [1]Molecular Crystals and Liquid Crystals,2017,vol. 644,p. 249 - 256

62
[ 84-85-5 ]
4-benzyl-1,3-di-o-acetyl-2,6-dideoxy-D-glucose [ No CAS ]
4-benzyl-3-o-acetyl-2,6-dideoxy-D-glucose-4-methoxy-1-naphthol-β-C-glycoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylsilane In dichloromethane at 15℃; for 0.75h; Inert atmosphere;	2 Under nitrogen, 30 mg (0.093 mmol) 4-benzyl-1,3-di-O-acetyl-2,6-dideoxy-D-glucose with 24.32 mg (0.14 mmol) of 4-methoxy-1-naphthol, After stirring, 5 mL of methylene chloride was added, 236.2 mg (0.093 mmol) of I2 and 4.47 μL (0.028 mmol) of Et3SiH catalyst were added at a temperature of 15 ° C, TLC spot plate (PE: EA = 6: 1) Tracking monitoring reaction, 45min TLC monitoring reaction is complete, the reaction solution by separation, After purification, 34.5 mg of the product was 4-benzyl-3-O-acetyl-2,6-dideoxy-D-glucose 4-methoxy-1-naphthol-β-C-glycoside in a yield of 85%

Reference： [1]Current Patent Assignee: EAST CHINA NORMAL UNIVERSITY - CN106967023, 2017, A Location in patent: Paragraph 0019-0020

63
[ 84-85-5 ]
C₁₈H₁₇NO₄S [ No CAS ]
C₂₉H₂₇NO₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With C₅₇H₅₄N₆O₆ In toluene at -15℃; for 96h; stereoselective reaction;

Reference： [1]Takizawa, Shinobu; Sako, Makoto; Abozeid, Mohamed Ahmed; Kishi, Kenta; Wathsala; Hirata, Shuichi; Murai, Kenichi; Fujioka, Hiromichi; Sasai, Hiroaki [Organic Letters, 2017, vol. 19, # 19, p. 5426 - 5429]

64
[ 5272-33-3 ]
[ 84-85-5 ]
(6-methoxy-2,2-dimethyl-2H-benzo[h]chromen-4-yl)trimethylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate; In neat (no solvent); for 3h;Heating;	General procedure: A mixture of suitable propargylic alcohol 1a (1.0 mmol) and naphthol 2a (1.2 mmol) was heated at 120oC in presence of Ca(OTf)2/Bu4NPF6 (5/10 mol%) for 2-4.5 h. After completion of reaction(monitored by TLC), the reaction mixture was diluted with water, extracted with EtOAc thrice, thecombined organic layers were washed with brine solution and dried over anhydrous Na2SO4. Solventwas removed under reduced pressure and the crude product was purified by silica gel columnchromatography (3-5 %, EtOAc in pet ether) to obtain the desired product 3a in 81% yield.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 4642 - 4647

65
[ 84-85-5 ]
[ 82663-57-8 ]
[ 18916-57-9 ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide In nitromethane; water at 96℃; for 0.666667h;	Oxidation Reactions and Product Separation General procedure: Oxidative coupling reactions (at r. t. or under reflux)were carried out in the same manner as described earlier[15]. That is, for each reaction 6.34 mmol starting material(SM) and 0.0401 g catalyst were used in 25 mL ofsolvent, to which 22.1 mmol H2O2 was added as a30% aq. solution over 40 min. The reaction mixture wasseparated by column chromatography. Product selectivitieswere calculated as mole percentages based on themoles of SM incorporated into each product. Turnoverfrequencies (TOFs) are reported as moles of H2O2required for the formation of all identified products(compare Scheme 1) per moles of platinum present inthe catalyst over the total reaction time (min-1)

Reference： [1]Maphoru; Heveling; Kesavan Pillai [Kinetics and Catalysis, 2017, vol. 58, # 4, p. 441 - 447][Kinet. Katal., 2017, vol. 58, # 4, p. 465 - 472,8]

66
[ 84-85-5 ]
[ 18916-57-9 ]
[ 59699-47-7 ]
[ 130-15-4 ]

Yield	Reaction Conditions	Operation in experiment
	With Pt(5%)Bi(5%)/C; dihydrogen peroxide In nitromethane; water at 20℃; for 0.666667h;	Oxidation Reactions and Product Separation General procedure: Oxidative coupling reactions (at r. t. or under reflux)were carried out in the same manner as described earlier[15]. That is, for each reaction 6.34 mmol starting material(SM) and 0.0401 g catalyst were used in 25 mL ofsolvent, to which 22.1 mmol H2O2 was added as a30% aq. solution over 40 min. The reaction mixture wasseparated by column chromatography. Product selectivitieswere calculated as mole percentages based on themoles of SM incorporated into each product. Turnoverfrequencies (TOFs) are reported as moles of H2O2required for the formation of all identified products(compare Scheme 1) per moles of platinum present inthe catalyst over the total reaction time (min-1)

Reference： [1]Maphoru; Heveling; Kesavan Pillai [Kinetics and Catalysis, 2017, vol. 58, # 4, p. 441 - 447][Kinet. Katal., 2017, vol. 58, # 4, p. 465 - 472,8]

67
[ 84-85-5 ]
[ 644-78-0 ]
2-methoxy-8-phenyl-14H-8,14-methanobenzo[d]naphtho[2,1-g][1,3]dioxocine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With [Yb(CH₃CN)9]³⁺[(AlCl₄)3]^3-.CH₃CN In chlorobenzene for 72h; Reflux; Inert atmosphere; Schlenk technique; stereoselective reaction;	4.3 Typical procedure for the synthesis of 2,8-dioxabicyclo[3.3.1]nonanes (product 3aa as an example) General procedure: A mixture of 2-hydroxychalcone (112mg, 0.5mmol), β-naphthol (87mg, 0.6mmol) and [Yb(CH3CN)9]3+[(AlCl4)3]3-·CH3CN (16mg, 0.015mmol) in anhydrous chlorobenzene (4.0mL) was stirred under reflux for 72h. The reaction was cooled to room temperature. Water was added, and the mixture was extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 20:1) to afford the desired 3aa as a white solid.

Reference： [1]Zhu, Yanan; Yao, Zhigang; Xu, Fan [Tetrahedron, 2018, vol. 74, # 31, p. 4211 - 4219]

68
[ 25414-22-6 ]
bis(3,5-bis(trifluoromethyl)phenyl)(2-triflyloxyphenyl)phosphine oxide [ No CAS ]
[ 84-85-5 ]

Yield	Reaction Conditions	Operation in experiment
59.8%	With phenylmagnesium bromide In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere;	A typical procedure for aryne generation from (2-triflyloxyaryl)phosphine oxides General procedure: To a mixture of bis(3,5-bis(trifluoromethyl)phenyl)(2-triflyloxyphenyl)phosphineoxide (1c) (135 mg, 0.193 mmol) and benzyl azide (2) (0.120 mL, 0.965 mmol) dissolved in THF (2.0 mL) was slowly added phenylmagnesium bromide (1.25 M, THF solution, 0.309 mL, 0.386 mmol) at room temperature. After stirring for 15 min at the same temperature, to the mixture was added an aqueous saturated solution of NH4Cl (2mL). The mixture was extracted with EtOAc (10 mL × 3), and the combined organic extract was dried (Na2SO4), and after filtration, the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (silica-gel12 g, n-hexane/EtOAc = 9/1 to 8/2), and then by preparative TLC (CH2Cl2/EtOAc =29/1) to give 1-benzyl-1H-benzo[d][1,2,3]triazole (3a) (28.5 mg, 0.136 mmol, 70.5%)as a colorless solid.

Reference： [1]Nishiyama, Yoshitake; Kamada, Shuhei; Yoshida, Suguru; Hosoya, Takamitsu [Chemistry Letters, 2018, vol. 47, # 9, p. 1216 - 1219]

69
[ 117-80-6 ]
[ 84-85-5 ]
[ 54808-03-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With pyridine; potassium carbonate at 90℃; for 24h;	General method for the base-induced coupling of 1,4-dihydroxynaphthalene derivatives(8a -8c) with 2,3-dichloro-1,4-naphthoquinone (6) General procedure: To a solution of naphthoquinone 10a-c (1.0 mmol) in methanol (20 mL), 10% palladium on activated carbon (0.1% by weight) was added. The mixture was shaken under hydrogen at apressure of 20 psi for 4 hours. Palladium was then filtered off, and the solvent removed invacuo. The crude naphthol was dissolved in pyridine (10 mL) after which potassium carbonate(10 mol. equiv.), followed by 2,3-dichloro-1,4-naphthoquinone (6) (1.2 mmol), were added.The mixture was heated at 90°C for 24 hours, quenched with water (100 mL), and the organicmaterial extracted with ethyl acetate (5 x 20 mL).The organic layer was washed with a supersaturated CuSO4 solution (10 x 10 mL), brine (2 x10 mL) and water (2 x 20 mL), dried over MgSO4, filtered, and the solvent removed in vacuoto obtain the crude diether 11a-c. Isolation of the pentacyclic dinaphthofurandione derivatives 9a-9c was completed afteracidification (1N HCl, 10 mL) of the aqueous layer and collection of the resultant precipitates.Purification of the crude products was done via column chromatography using ethyl acetate hexane mixtures.

Reference： [1]Daley, Sharna-Kay A.; Downer-Riley, Nadale K. [Synlett, 2019, vol. 30, # 3, p. 325 - 328]

70
[ 84-85-5 ]
[ 1550-35-2 ]
[ 109-77-3 ]
2-amino-6-methoxy-4-(2,4-difluorophenyl)-4H-benzo[h]chromene-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With piperidine In ethanol at 140℃; for 0.0333333h; Microwave irradiation;	2.2.1. General procedure for synthesis of 4H-benzo[h]chromenederivatives (4a-m) General procedure: A reaction mixture of 4-methoxy-1-naphthol 1 (0.01 mol),different aromatic aldehydes 2a-m (0.01 mol), malononitrile 3(0.01 mol), and piperidine (0.5 mL) in ethanol (30 mL) was heatedunder microwave irradiation conditions for 2 min at 140 C. Afterthe completion of the reaction, the reaction mixture was cooled toroom temperature, and the precipitated solid was filtered off,washed with MeOH, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are asfollows.

Reference： [1]Ahmed, Hany E.A.; El-Nassag, Mohammed A.A.; Hassan, Ahmed H.; Mohamed, Hany M.; Halawa, Ahmed H.; Okasha, Rawda M.; Ihmaid, Saleh; Abd El-Gilil, Shimaa Mohamed; Khattab, Essam S.A.E.H.; Fouda, Ahmed M.; El-Agrody, Ahmed M.; Aljuhani, Ateyatallah; Afifi, Tarek H. [Journal of Molecular Structure, 2019, vol. 1186, p. 212 - 223]

71
[ 84-85-5 ]
[ 437-81-0 ]
[ 109-77-3 ]
2-amino-6-methoxy-4-(2,6-difluorophenyl)-4H-benzo[h]chromene-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With piperidine In ethanol at 140℃; for 0.0333333h; Microwave irradiation;	2.2.1. General procedure for synthesis of 4H-benzo[h]chromenederivatives (4a-m) General procedure: A reaction mixture of 4-methoxy-1-naphthol 1 (0.01 mol),different aromatic aldehydes 2a-m (0.01 mol), malononitrile 3(0.01 mol), and piperidine (0.5 mL) in ethanol (30 mL) was heatedunder microwave irradiation conditions for 2 min at 140 C. Afterthe completion of the reaction, the reaction mixture was cooled toroom temperature, and the precipitated solid was filtered off,washed with MeOH, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are asfollows.

Reference： [1]Ahmed, Hany E.A.; El-Nassag, Mohammed A.A.; Hassan, Ahmed H.; Mohamed, Hany M.; Halawa, Ahmed H.; Okasha, Rawda M.; Ihmaid, Saleh; Abd El-Gilil, Shimaa Mohamed; Khattab, Essam S.A.E.H.; Fouda, Ahmed M.; El-Agrody, Ahmed M.; Aljuhani, Ateyatallah; Afifi, Tarek H. [Journal of Molecular Structure, 2019, vol. 1186, p. 212 - 223]

72
[ 84-85-5 ]
[ 89-98-5 ]
[ 109-77-3 ]
2-amino-6-methoxy-4-(2-chlorophenyl)-4H-benzo[h]chromene-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With piperidine In ethanol at 140℃; for 0.0333333h; Microwave irradiation;	2.2.1. General procedure for synthesis of 4H-benzo[h]chromenederivatives (4a-m) General procedure: A reaction mixture of 4-methoxy-1-naphthol 1 (0.01 mol),different aromatic aldehydes 2a-m (0.01 mol), malononitrile 3(0.01 mol), and piperidine (0.5 mL) in ethanol (30 mL) was heatedunder microwave irradiation conditions for 2 min at 140 C. Afterthe completion of the reaction, the reaction mixture was cooled toroom temperature, and the precipitated solid was filtered off,washed with MeOH, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are asfollows.

Reference： [1]Ahmed, Hany E.A.; El-Nassag, Mohammed A.A.; Hassan, Ahmed H.; Mohamed, Hany M.; Halawa, Ahmed H.; Okasha, Rawda M.; Ihmaid, Saleh; Abd El-Gilil, Shimaa Mohamed; Khattab, Essam S.A.E.H.; Fouda, Ahmed M.; El-Agrody, Ahmed M.; Aljuhani, Ateyatallah; Afifi, Tarek H. [Journal of Molecular Structure, 2019, vol. 1186, p. 212 - 223]

73
[ 84-85-5 ]
[ 587-04-2 ]
[ 109-77-3 ]
2-amino-6-methoxy-4-(3-chlorophenyl)-4H-benzo[h]chromene-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With piperidine In ethanol at 140℃; for 0.0333333h; Microwave irradiation;	2.2.1. General procedure for synthesis of 4H-benzo[h]chromenederivatives (4a-m) General procedure: A reaction mixture of 4-methoxy-1-naphthol 1 (0.01 mol),different aromatic aldehydes 2a-m (0.01 mol), malononitrile 3(0.01 mol), and piperidine (0.5 mL) in ethanol (30 mL) was heatedunder microwave irradiation conditions for 2 min at 140 C. Afterthe completion of the reaction, the reaction mixture was cooled toroom temperature, and the precipitated solid was filtered off,washed with MeOH, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are asfollows.

Reference： [1]Ahmed, Hany E.A.; El-Nassag, Mohammed A.A.; Hassan, Ahmed H.; Mohamed, Hany M.; Halawa, Ahmed H.; Okasha, Rawda M.; Ihmaid, Saleh; Abd El-Gilil, Shimaa Mohamed; Khattab, Essam S.A.E.H.; Fouda, Ahmed M.; El-Agrody, Ahmed M.; Aljuhani, Ateyatallah; Afifi, Tarek H. [Journal of Molecular Structure, 2019, vol. 1186, p. 212 - 223]

74
[ 84-85-5 ]
[ 6334-18-5 ]
[ 109-77-3 ]
2-amino-6-methoxy-4-(2,3-dichlorophenyl)-4H-benzo[h]chromene-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With piperidine In ethanol at 140℃; for 0.0333333h; Microwave irradiation;	2.2.1. General procedure for synthesis of 4H-benzo[h]chromenederivatives (4a-m) General procedure: A reaction mixture of 4-methoxy-1-naphthol 1 (0.01 mol),different aromatic aldehydes 2a-m (0.01 mol), malononitrile 3(0.01 mol), and piperidine (0.5 mL) in ethanol (30 mL) was heatedunder microwave irradiation conditions for 2 min at 140 C. Afterthe completion of the reaction, the reaction mixture was cooled toroom temperature, and the precipitated solid was filtered off,washed with MeOH, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are asfollows.

Reference： [1]Ahmed, Hany E.A.; El-Nassag, Mohammed A.A.; Hassan, Ahmed H.; Mohamed, Hany M.; Halawa, Ahmed H.; Okasha, Rawda M.; Ihmaid, Saleh; Abd El-Gilil, Shimaa Mohamed; Khattab, Essam S.A.E.H.; Fouda, Ahmed M.; El-Agrody, Ahmed M.; Aljuhani, Ateyatallah; Afifi, Tarek H. [Journal of Molecular Structure, 2019, vol. 1186, p. 212 - 223]

75
[ 84-85-5 ]
[ 874-42-0 ]
[ 109-77-3 ]
2-amino-6-methoxy-4-(2,4-dichlorophenyl)-4H-benzo[h]chromene-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With piperidine In ethanol at 140℃; for 0.0333333h; Microwave irradiation;	2.2.1. General procedure for synthesis of 4H-benzo[h]chromenederivatives (4a-m) General procedure: A reaction mixture of 4-methoxy-1-naphthol 1 (0.01 mol),different aromatic aldehydes 2a-m (0.01 mol), malononitrile 3(0.01 mol), and piperidine (0.5 mL) in ethanol (30 mL) was heatedunder microwave irradiation conditions for 2 min at 140 C. Afterthe completion of the reaction, the reaction mixture was cooled toroom temperature, and the precipitated solid was filtered off,washed with MeOH, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are asfollows.

Reference： [1]Ahmed, Hany E.A.; El-Nassag, Mohammed A.A.; Hassan, Ahmed H.; Mohamed, Hany M.; Halawa, Ahmed H.; Okasha, Rawda M.; Ihmaid, Saleh; Abd El-Gilil, Shimaa Mohamed; Khattab, Essam S.A.E.H.; Fouda, Ahmed M.; El-Agrody, Ahmed M.; Aljuhani, Ateyatallah; Afifi, Tarek H. [Journal of Molecular Structure, 2019, vol. 1186, p. 212 - 223]

76
[ 6361-23-5 ]
[ 84-85-5 ]
[ 109-77-3 ]
2-amino-6-methoxy-4-(2,5-dichlorophenyl)-4H-benzo[h]chromene-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With piperidine; In ethanol; at 140℃; for 0.0333333h;Microwave irradiation;	General procedure: A reaction mixture of 4-methoxy-1-naphthol 1 (0.01 mol),different aromatic aldehydes 2a-m (0.01 mol), malononitrile 3(0.01 mol), and piperidine (0.5 mL) in ethanol (30 mL) was heatedunder microwave irradiation conditions for 2 min at 140 C. Afterthe completion of the reaction, the reaction mixture was cooled toroom temperature, and the precipitated solid was filtered off,washed with MeOH, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are asfollows.

Reference： [1]Journal of Molecular Structure,2019,vol. 1186,p. 212 - 223

77
[ 84-85-5 ]
[ 83-38-5 ]
[ 109-77-3 ]
2-amino-6-methoxy-4-(2,6-dichlorophenyl)-4H-benzo[h]chromene-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With piperidine In ethanol at 140℃; for 0.0333333h; Microwave irradiation;	2.2.1. General procedure for synthesis of 4H-benzo[h]chromenederivatives (4a-m) General procedure: A reaction mixture of 4-methoxy-1-naphthol 1 (0.01 mol),different aromatic aldehydes 2a-m (0.01 mol), malononitrile 3(0.01 mol), and piperidine (0.5 mL) in ethanol (30 mL) was heatedunder microwave irradiation conditions for 2 min at 140 C. Afterthe completion of the reaction, the reaction mixture was cooled toroom temperature, and the precipitated solid was filtered off,washed with MeOH, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are asfollows.

Reference： [1]Ahmed, Hany E.A.; El-Nassag, Mohammed A.A.; Hassan, Ahmed H.; Mohamed, Hany M.; Halawa, Ahmed H.; Okasha, Rawda M.; Ihmaid, Saleh; Abd El-Gilil, Shimaa Mohamed; Khattab, Essam S.A.E.H.; Fouda, Ahmed M.; El-Agrody, Ahmed M.; Aljuhani, Ateyatallah; Afifi, Tarek H. [Journal of Molecular Structure, 2019, vol. 1186, p. 212 - 223]

78
[ 84-85-5 ]
[ 6287-38-3 ]
[ 109-77-3 ]
2-amino-6-methoxy-4-(3,4-dichlorophenyl)-4H-benzo[h]chromene-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With piperidine In ethanol at 140℃; for 0.0333333h; Microwave irradiation;	2.2.1. General procedure for synthesis of 4H-benzo[h]chromenederivatives (4a-m) General procedure: A reaction mixture of 4-methoxy-1-naphthol 1 (0.01 mol),different aromatic aldehydes 2a-m (0.01 mol), malononitrile 3(0.01 mol), and piperidine (0.5 mL) in ethanol (30 mL) was heatedunder microwave irradiation conditions for 2 min at 140 C. Afterthe completion of the reaction, the reaction mixture was cooled toroom temperature, and the precipitated solid was filtered off,washed with MeOH, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are asfollows.

Reference： [1]Ahmed, Hany E.A.; El-Nassag, Mohammed A.A.; Hassan, Ahmed H.; Mohamed, Hany M.; Halawa, Ahmed H.; Okasha, Rawda M.; Ihmaid, Saleh; Abd El-Gilil, Shimaa Mohamed; Khattab, Essam S.A.E.H.; Fouda, Ahmed M.; El-Agrody, Ahmed M.; Aljuhani, Ateyatallah; Afifi, Tarek H. [Journal of Molecular Structure, 2019, vol. 1186, p. 212 - 223]

79
[ 84-85-5 ]
[ 61657-65-6 ]
[ 109-77-3 ]
2-amino-6-methoxy-4-(3,5-dibromo-2-methoxyphenyl)-4Hbenzo[h]chromene-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With piperidine In ethanol at 140℃; for 0.0333333h; Microwave irradiation;	2.2.1. General procedure for synthesis of 4H-benzo[h]chromenederivatives (4a-m) General procedure: A reaction mixture of 4-methoxy-1-naphthol 1 (0.01 mol),different aromatic aldehydes 2a-m (0.01 mol), malononitrile 3(0.01 mol), and piperidine (0.5 mL) in ethanol (30 mL) was heatedunder microwave irradiation conditions for 2 min at 140 C. Afterthe completion of the reaction, the reaction mixture was cooled toroom temperature, and the precipitated solid was filtered off,washed with MeOH, and recrystallized from ethanol or ethanol/benzene. The physical and spectral data of compounds 4a-m are asfollows.

Reference： [1]Ahmed, Hany E.A.; El-Nassag, Mohammed A.A.; Hassan, Ahmed H.; Mohamed, Hany M.; Halawa, Ahmed H.; Okasha, Rawda M.; Ihmaid, Saleh; Abd El-Gilil, Shimaa Mohamed; Khattab, Essam S.A.E.H.; Fouda, Ahmed M.; El-Agrody, Ahmed M.; Aljuhani, Ateyatallah; Afifi, Tarek H. [Journal of Molecular Structure, 2019, vol. 1186, p. 212 - 223]

80
[ 84-85-5 ]
C₁₃H₉NO₂S [ No CAS ]
(-)-7-(1-hydroxy-4-methoxynaphthalen-2-yl)-6,7-dihydrodibenzo[d,f][1,2]thiazepine 5,5-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With Cinchonin In chloroform at 0℃; for 18h; Schlenk technique; Inert atmosphere; enantioselective reaction;
93%	With cinchonine In chloroform at 0℃; Inert atmosphere; enantioselective reaction;	18 Example 17-32 General procedure: Organocatalytic synthesis of a series of chiral seven-membered cyclic sulfonamide compounds. Under the protection of nitrogen, add seven-membered cyclic imine (0.2 mmol), naphthol compounds and organic small molecule catalysts (catalyst 4f is used in Example 28, 4b is used in other examples), and then organic Solvent (12 ml of toluene was used in Example 28, and 12 ml of chloroform in the remaining examples). After stirring at 0°C for 3-72 hours, the solvent was directly spin-dried to dryness. Column chromatography (volume of eluent petroleum ether and ethyl acetate) The ratio is 5:1) to obtain the corresponding chiral seven-membered cyclic sulfonamide; the molar ratio of the seven-membered cyclic imine, naphthol compound, and catalyst is in the range of 1:1.5:0.1.The yield is the separation yield, the organic catalyst, organic solvent and reaction temperature are changed, and the enantiomeric excess of the product is determined by chiral liquid chromatography.16 different examples were obtained by changing the types of raw materials and substrates in the reaction, and the types of changes are shown in Table 2.

Reference： [1]Zhao, Zi-Biao; Shi, Lei; Li, Yaming; Meng, Fan-Jie; Zhou, Yong-Gui [Organic and Biomolecular Chemistry, 2019, vol. 17, # 26, p. 6364 - 6368]
[2]Current Patent Assignee: Dalian Institute of Chemical Physics (in: CAS); CHINESE ACADEMY OF SCIENCES - CN111808045, 2020, A Location in patent: Paragraph 0034-0040; 0042

81
[ 84-85-5 ]
2-benzylidene-N-tosylbenzofuran-3(2H)-imine [ No CAS ]
(R)-N-(2-((1-hydroxy-4-methoxynaphthalen-2-yl)(phenyl)methyl)benzofuran-3-yl)-4-methylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With C₃₁H₂₆F₆N₄O₂ In dichloromethane at 50℃; for 16h; enantioselective reaction;

Reference： [1]Cheng, Yuyu; Li, Fushuai; Li, Pengfei; Li, Wenjun; Luan, Yepeng; Zhang, Chen [Advanced synthesis and catalysis, 2020]

82
[ 103-82-2 ]
[ 84-85-5 ]
phenylacetic acid 4-methoxynaphthalen-1-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: phenylacetic acid With phosphoric acid; trifluoroacetic anhydride In acetonitrile at 25℃; for 0.5h; Stage #2: 4-methoxynaphth-1-ol In acetonitrile at 25℃; for 20h;

Reference： [1]Chang, Meng-Yang; Chen, Kuan-Ting; Chen, Shin-Mei; Hsiao, Yu-Ting [Journal of Organic Chemistry, 2020, vol. 85, # 5, p. 3605 - 3616]

83
[ 73689-84-6 ]
[ 64648-86-8 ]
[ 84-85-5 ]
11-hydroxy-5,5-dimethoxy-3,3-dimethylanthra[2,3-c]furan-1,10(3H,5H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 80% 2: 60 mg	With lithium hexamethyldisilazane In toluene at 0 - 50℃; for 1h; Reflux; regioselective reaction;

Reference： [1]Huang, Jing-Kai; Shia, Kak-Shan [Angewandte Chemie - International Edition, 2020, vol. 59, # 16, p. 6540 - 6545][Angew. Chem., 2020, vol. 132, # 16, p. 6602 - 6607,6]

84
[ 84-85-5 ]
[ 2905-56-8 ]
2-(1-benzylpiperidin-2-yl)-4-methoxynaphthalen-1-ol [ No CAS ]

Reference： [1]Organic Letters,2020,vol. 22,p. 4781 - 4785

85
[ 14371-10-9 ]
[ 84-85-5 ]
6-methoxy-2-phenyl-2H-benzo[h]chromene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With 1,2-diamino-benzene In dichloromethane at 40℃; for 26h; Inert atmosphere;	4. General Procedure for the Synthesis of 2H-Benzo[h]Chromene 3 General procedure: Dry CH2Cl2 (1.0 mL) was added to a mixture of o-phenylenediamine (IX, 0.04 mmol),enal 1 (0.30 mmol) and arylol 2 (0.20 mmol) under Ar. The reaction was stirred at 40 Cuntil the completion of 2 monitored by TLC. Then, the mixture was applied to columnchromatography directly and eluted with ethyl ether and hexane (9/1) to give product 3.

Reference： [1]Gao, Feng; Ji, Peng; Meng, Xiang; Wang, Wei; Zeng, Fanxun; Zhang, Yueteng [Molecules, 2021, vol. 26, # 12]

86
[ 938-24-9 ]
[ 84-85-5 ]
6b,11b-dihydroxy-5-methoxy-6bH-indeno[1,2-b]naphtho[2,1-d]furan-7(11bH)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	In acetic acid at 20℃; for 0.5h; Reflux; regioselective reaction;	Synthesis of adduct 4j A mixture of ninhydrin (1.0 mmol) and 4-methoxy-1-naphthol 1j (2.0 mmol) was stirred in glacial acetic acid (6.0 mL) at room temperature for 30 min. The yellow precipitate separated was filtered and washed thoroughly with cold acetic acid followed by water. Recrystallization from acetone afforded pure compound 4j. 6b,11b-Dihydroxy-5-methoxy-6bH-indeno[1,2-b]naphtho[2,1-d]furan-7(11bH)-one, 4j: Yellow crystals, yield: 84%, m.p. 196-197C. IR (KBr): 3452, 3292, 3074, 1707, 1602,1419, 1229, 1159 cm-1.1H NMR (500 MHz, DMSO-d6) δ: 8.23 (1H, s), 8.05-8.03 (2H, m), 7.87 (1H, t, J = 7.5 Hz), 7.83 (1H, dd, J = 7.0, 2.0 Hz), 7.71 (1H, d, J = 7.5 Hz), 7.59 (1H, t, J = 7.5 Hz), 7.53-7.47 (2H, m), 6.86 (1H, s), 6.84 (1H, s), 3.87 (3H, s). 13C NMR (125 MHz, DMSO-d6) δ: 200.0, 150.4, 149.4, 146.5, 137.3, 134.2, 131.6, 127.4, 127.3, 127.0, 125.6, 123.4, 122.7, 121.7, 120.7, 117.7, 110.9, 99.9, 84.3, 56.2. Anal. Calcd for C20H14O5: C 71.85, H 4.22; Found: C 71.69, H 4.38.

Reference： [1]Das, Suven; Maity, Suvendu; Ghosh, Prasanta; Dutta, Arpita [Synthetic Communications, 2021, vol. 51, # 18, p. 2862 - 2872]

87
[ 84-85-5 ]
[ 1161782-29-1 ]
1-hydroxy-4-methoxy-1-(3'-O-acetyl-4'-O-benzyl-2,6-dideoxy-β-D-glucopyranosyl)naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylsilane; iodine In 1,2-dichloro-ethane at 20℃; for 0.25h; Inert atmosphere; stereoselective reaction;	General Synthetic Procedure General procedure: I2 (50.8 mg, 0.2 mmol) was added to a stirred solution of1,3,4-tri-O-acetyl-2,6-dideoxy-α-glucopyranoside 1a (54.8 mg, 0.2 mmol) and2-naphthol 2a (43.2 mg, 0.3 mmol) in anhydrous DCE (4 mL), followed by theaddition of Et3SiH (9.6 μL, 0.06 mmol) after 5 min at room temperature. After thecompletion monitored by TLC, the reaction mixture was quenched with saturatedsodium thiosulfate solution (5 mL) and extracted with DCM (20 mL). The combinedorganic layers were washed with brine (5 mL), dried over anhydrous sodium sulfate,filtered, and concentrated under vacuum. The crude product was purified by columnchromatography with petroleum ether/ethyl acetate as an eluent to get 3a in 99% yield(70.9 mg).

Reference： [1]Mei, Yuling; Jiang, Nan; Yang, Yu; Zhang, Wan; Qiu, Saifeng; Guo, Hong; Zhang, Jianbo [Synlett, 2021, vol. 32, # 20, p. 2075 - 2079]

88
[ 84-85-5 ]
[ 67515-49-5 ]
2-(benzyloxy)-6-methoxy-3,4-dihydro-2H-benzo[h]chromene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With diphenyl hydrogen phosphate In dichloromethane at 25℃; for 8h; Schlenk technique;	Preparation of 3; Typical Procedure General procedure: To a mixture of naphthalen-2-ol (144 mg, 1.0 mmol) and diphenyl hydrogen phosphate (12.5 mg, 0.05 mmol) in CH2Cl2 (10 mL) was added((propa-1,2-dien-1-yloxy)methyl)benzene (248 mg, 1.7 mmol), and stirring was continued for 8 h at room temperature. The reaction mixture was concentrated to give a residue, which was purified by flash chromatography on silica gel (hexane/EtOAc, 180:1) to afford the corresponding pure compound 3.

Reference： [1]He, Maosheng; Zhang, Jinlong; Zhang, Cong; Wang, Hao-Yang; Jiang, Gaoxi [Synthesis, 2022, vol. 54, # 9, p. 2148 - 2156]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	84-85-5	MDL No. :	MFCD00003976
Formula :	C₁₁H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BOTGCZBEERTTDQ-UHFFFAOYSA-N
M.W :	174.20	Pubchem ID :	66542
Synonyms :

Num. heavy atoms :	13
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.09
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	52.46
TPSA :	29.46 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.78 cm/s

Log Po/w (iLOGP) :	1.85
Log Po/w (XLOGP3) :	2.23
Log Po/w (WLOGP) :	2.55
Log Po/w (MLOGP) :	2.17
Log Po/w (SILICOS-IT) :	2.48
Consensus Log Po/w :	2.26

[ CAS No. 84-85-5 ] {[proInfo.proName]}

Quality Control of [ 84-85-5 ]

Related Doc. of [ 84-85-5 ]

Product Details of [ 84-85-5 ]

Calculated chemistry of [ 84-85-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 84-85-5 ]

Application In Synthesis of [ 84-85-5 ]

[ 84-85-5 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 84-85-5 ]

Aryls

Ethers

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-2.83
Solubility :	0.259 mg/ml ; 0.00149 mol/l
Class :	Soluble
Log S (Ali) :	-2.48
Solubility :	0.572 mg/ml ; 0.00328 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.62
Solubility :	0.0416 mg/ml ; 0.000239 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.07

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 84-85-5 ] {[proInfo.proName]}

Quality Control of [ 84-85-5 ]

Related Doc. of [ 84-85-5 ]

Product Details of [ 84-85-5 ]

Calculated chemistry of [ 84-85-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 84-85-5 ]

Application In Synthesis of [ 84-85-5 ]

[ 84-85-5 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 84-85-5 ]

Aryls

Ethers

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 84-85-5 ]