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Chemistry
Organic Building Blocks
Aryls
naphthyl
2,7-Dimethylnaphthalene
Chemistry
Material Science
Organic Building Blocks
Electronic Materials
Aryls
Benzene Compounds Organic Light-Emitting Diode (OLED) Materials
naphthyl
2-methylnaphthalene

[ CAS No. 582-16-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
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3d Animation Molecule Structure of 582-16-1
Chemical Structure| 582-16-1
Chemical Structure| 582-16-1
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Quality Control of [ 582-16-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 582-16-1 ]

SDS Specification
Alternatived Products of [ 582-16-1 ]

Product Details of [ 582-16-1 ]

CAS No. :582-16-1 MDL No. :MFCD00004121
Formula : C12H12 Boiling Point : -
Linear Structure Formula :- InChI Key :LRQYSMQNJLZKPS-UHFFFAOYSA-N
M.W : 156.22 Pubchem ID :11396
Synonyms :

Calculated chemistry of [ 582-16-1 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.17
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 53.88
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.51
Log Po/w (XLOGP3) : 4.31
Log Po/w (WLOGP) : 3.46
Log Po/w (MLOGP) : 4.83
Log Po/w (SILICOS-IT) : 3.97
Consensus Log Po/w : 3.81

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.14
Solubility : 0.0113 mg/ml ; 0.0000724 mol/l
Class : Moderately soluble
Log S (Ali) : -4.02
Solubility : 0.0148 mg/ml ; 0.0000947 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.83
Solubility : 0.00229 mg/ml ; 0.0000147 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.0

Safety of [ 582-16-1 ]

Signal Word:Danger Class:9
Precautionary Statements:P264-P270-P273-P280-P301+P310-P305+P351+P338-P331-P337+P313-P391-P405-P501 UN#:3077
Hazard Statements:H302-H304-H319-H400-H412 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 582-16-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 582-16-1 ]

[ 582-16-1 ] Synthesis Path-Downstream   1~88

  • 1
  • [ 108-30-5 ]
  • [ 582-16-1 ]
  • 4-(2,7-dimethyl-[1]naphthyl)-4-oxo-butyric acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With aluminium trichloride; nitrobenzene
Reference： [1]Fieser; Peters [Journal of the American Chemical Society, 1932, vol. 54, p. 4347,4355]
  • 2
  • [ 85-44-9 ]
  • [ 582-16-1 ]
  • 2-(3,6-dimethyl-[2]naphthoyl)-benzoic acid [ No CAS ]
  • [ 860596-39-0 ]
YieldReaction ConditionsOperation in experiment
With aluminium trichloride; 1,1,2,2-tetrachloroethane
Reference： [1]Fieser; Fieser [Journal of the American Chemical Society, 1933, vol. 55, p. 3342,3351]
  • 3
  • [ 50-00-0 ]
  • [ 582-16-1 ]
  • [ 246874-31-7 ]
YieldReaction ConditionsOperation in experiment
62% With hydrogenchloride; acetic acid at 50℃; for 24h;
62% With hydrogenchloride; acetic acid
62% With hydrogenchloride; acetic acid
With hydrogenchloride; acetic acid at 40℃;

Reference： [1]Borchardt, Allen; Hardcastle, Kenneth; Gantzel, Peter; Siegel, Jay S. [Tetrahedron Letters, 1993, vol. 34, # 2, p. 273 - 276]
[2]Seiders, T. Jon; Elliott, Eric L.; Grube, Gunther H.; Siegel, Jay S. [Journal of the American Chemical Society, 1999, vol. 121, # 34, p. 7804 - 7813]
[3]Jones, Carissa S.; Elliott, Eric; Siegel, Jay S. [Synlett, 2004, # 1, p. 187 - 191]
[4]Buu-Hoi; Cagniant [Revue Scientifique, 1942, vol. 80, p. 130,132][Chem.Abstr., 1944, p. 3642]
  • 4
  • [ 582-16-1 ]
  • [ 137823-66-6 ]
YieldReaction ConditionsOperation in experiment
With molybdenum sulfide coal catalyst at 300℃; Hydrogenation;
Reference： [1]Coulson [Journal of the Chemical Society, 1935, p. 77,81]
  • 5
  • [ 582-16-1 ]
  • [ 37558-62-6 ]
YieldReaction ConditionsOperation in experiment
99% With bromine In dichloromethane at 0℃; for 4h;
97% With N-Bromosuccinimide In N,N-dimethyl-formamide; acetonitrile at 20℃; for 16h; 4.B Step B: Preparation of l-bromo-2,7-dimethylnaphthalene To a solution of 2,7-dimethylnaphthalene (i.e. the product obtained in Step A, 282 g, 1.8 mol) in CH3CN (2.8 L) and N, A-di m ethyl form am i de (200 mL) was added A -b rom osucci n i m i de (321 g, 1.8 mol) and the reaction mixture was stirred at room temperature for 16 h. Analasys by TLC in hexane showed completion of the reaction. The reaction mixture was poured into ice water and extracted with petroleum ether thrice. The combined organic layer was washed with water, brine and dried over Na2S04. The solvent was evaporated to give the crude product which was purified by silica gel chromatography eluting with petroleum ether to provide 415 g (97% yield) of the title product as pale yellow solid.
82% With bromine In carbon disulfide for 1h; 273 K to rt;
71% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃;
With carbon disulfide; bromine
With bromine
With bromine In dichloromethane at 0℃; Inert atmosphere;
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; Schlenk technique; Inert atmosphere;

Reference： [1]Luan, Xinjun; Mariz, Ronaldo; Gatti, Michele; Costabile, Chiara; Poater, Albert; Cavallo, Luigi; Linden, Anthony; Dorta, Reto [Journal of the American Chemical Society, 2008, vol. 130, # 21, p. 6848 - 6858]
[2]Current Patent Assignee: FMC CORP - WO2020/69057, 2020, A1 Location in patent: Page/Page column 44-45
[3]Brown, Laurie A.; Laxman, Ravi K.; Maverick, Andrew W.; Fronczek, Frank R. [Acta Crystallographica, Section C: Crystal Structure Communications, 1996, vol. 52, p. 95 - 97]
[4]Larkem; Larkem; Messadi [Egyptian Journal of Chemistry, 2004, vol. 47, # 4, p. 413 - 426]
[5]Buu-Hoi; Lecocq [Journal of the Chemical Society, 1946, p. 830] Clar; Wallenstein [Chemische Berichte, 1931, vol. 64, p. 2076,2080]
[6]Wolinska-Mocydlarz,J. et al. [Synthesis, 1974, p. 566 - 568]
[7]Location in patent: scheme or table Ludovic, Vieille-Petit; Luan, Xinjun; Mariz, Ronaldo; Blumentritt, Sascha; Linden, Anthony; Dorta, Reto [European Journal of Inorganic Chemistry, 2009, # 13 SPEC. ISS., p. 1861 - 1870]
[8]González-Fernández, Elisa; Nicholls, Leo D.M.; Schaaf, Lukas D.; Farès, Christophe; Lehmann, Christian W.; Alcarazo, Manuel [Journal of the American Chemical Society, 2017, vol. 139, # 4, p. 1428 - 1431]
  • 6
  • [ 582-16-1 ]
  • [ 482-70-2 ]
YieldReaction ConditionsOperation in experiment
89% With ammonium persulfate; sulfuric acid; sodium dodecyl-sulfate In cyclohexane; water at 50℃; for 5h;
79% With chromium(VI) oxide; periodic acid In acetonitrile at 5℃; for 1h;
67% With chromium(VI) oxide In acetic acid at 50℃; for 0.75h;
55% With chromium(VI) oxide In acetic acid
With chromium(VI) oxide; acetic acid
With chromium(VI) oxide; acetic acid

Reference： [1]Skarzewski, Jacek [Tetrahedron, 1984, vol. 40, # 23, p. 4997 - 5000]
[2]Yamazaki, Shigekazu [Tetrahedron Letters, 2001, vol. 42, # 19, p. 3355 - 3357]
[3]Schmid, Ralf; Goebel, Friederike; Warnecke, Andre; Labahn, Andreas [Journal of the Chemical Society. Perkin Transactions 2 (2001), 1999, # 6, p. 1199 - 1202]
[4]Pluim, Henk; Wynberg, Hans [Journal of Organic Chemistry, 1980, vol. 45, # 12, p. 2498 - 2502]
[5]Weiszgerber; Kruber [Chemische Berichte, 1919, vol. 52, p. 367]
[6]Current Patent Assignee: Ges. f. Teerverwertung - DE301079, 1800, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 13, p. 209][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 13, p. 209]
  • 7
  • [ 582-16-1 ]
  • [ 52988-17-7 ]
YieldReaction ConditionsOperation in experiment
57% With N-Bromosuccinimide; azobisisobutyronitrile In tetrachloromethane for 2.5h; Heating;
With tetrachloromethane; N-Bromosuccinimide
Reference： [1]Gorsane, M.; Martin, R. H. [Bulletin des Societes Chimiques Belges, 1985, vol. 94, # 3, p. 205 - 214]
[2]Lecocq [Annales de Chimie (Cachan, France), 1948, vol. <12> 3, p. 62,84] Buu-Hoi; Lecocq [Journal of the Chemical Society, 1946, p. 830]
  • 8
  • [ 137823-66-6 ]
  • [ 582-16-1 ]
YieldReaction ConditionsOperation in experiment
With platinum on activated charcoal; palladium-platinum at 440℃;
Reference： [1]Baker et al. [Journal of the Chemical Society, 1952, p. 2991]
  • 9
  • [ 582-16-1 ]
  • [ 38309-89-6 ]
YieldReaction ConditionsOperation in experiment
98% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 80℃; for 9h;
92% With N-Bromosuccinimide; dibenzoyl peroxide In benzene for 8h; Reflux;
92% With N-Bromosuccinimide; dibenzoyl peroxide In benzene at 120℃; for 8h; Inert atmosphere;
91% With N-Bromosuccinimide; dibenzoyl peroxide In benzene at 120℃; for 2h;
90% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 80℃; for 18h;
88% With N-Bromosuccinimide; Azocyclohexan In Methyl formate for 18h; Heating;
88% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 0.166667h; Heating;
85% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 0.166667h; Reflux;
85% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 0.166667h; Reflux;
71% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 4.5h; Heating;
67% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane Reflux; Inert atmosphere;
64% With N-Bromosuccinimide In acetone Irradiation;
58% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 2h; Reflux;
57% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 80℃; Inert atmosphere;
50% With N-Bromosuccinimide; dibenzoyl peroxide In acetone Inert atmosphere; Irradiation;
41.5% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 20℃; for 3h; Inert atmosphere; Reflux;
29.9% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) at 80℃; 56 Synthesis of 2,7-bis(bromomethyl)naphthalene To a solution of 2,7-dimethylnaphthalene (1 g, 6.40 mmol) and 1-bromopyrrolidine-2,5-dione (2.5 g, 14.08 mmol) in perchloromethane (40 mL) was added 2,2'-Azobis-(2- methylpropanenitrile) (105 mg, 0.64 mmol). The mixture was stirred at 80 overnight. The insoluble solid was removed by filtration through a celite pad. The filtrate was washed with saturated sodium bicarbonate solution (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated to get the crude. It was purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 100:1) to afford 2,7-bis(bromomethyl)naphthalene (600 mg, 1.91 mmol, 29.9 % yield) as a white solid
With N-Bromosuccinimide
(bromination);
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane
With N-Bromosuccinimide In tetrachloromethane

Reference： [1]Minami, Atsushi; Uchida, Rei; Eguchi, Tadashi; Kakinuma, Katsumi [Journal of the American Chemical Society, 2005, vol. 127, # 17, p. 6148 - 6149]
[2]Location in patent: body text Christiansen, Michael A.; Butler, Aaron W.; Hill, Amanda R.; Andrus, Merritt B. [Synlett, 2009, # 4, p. 653 - 657]
[3]Andrus, Merritt B.; Harper, Kaid C.; Christiansen, Michael A.; Binkley, Meisha A. [Tetrahedron Letters, 2009, vol. 50, # 31, p. 4541 - 4544]
[4]Andrus, Merritt B.; Christiansen, Michael A.; Hicken, Erik J.; Gainer, Morgan J.; Bedke, D. Karl; Harper, Kaid C.; Mikkelson, Shawn R.; Dodson, Daniel S.; Harris, David T. [Organic Letters, 2007, vol. 9, # 23, p. 4865 - 4868]
[5]Location in patent: experimental part Geer, Michael F.; Smith, Mark D.; Shimizu, Linda S. [CrystEngComm, 2011, vol. 13, # 11, p. 3665 - 3669]
[6]Larkem; Larkem; Messadi [Egyptian Journal of Chemistry, 2004, vol. 47, # 4, p. 413 - 426]
[7]Lee, Jeong-Hee; Yoo, Mi-Sook; Jung, Ji-Hee; Jew, Sang-sup; Park, Hyeung-geun; Jeong, Byeong-Seon [Tetrahedron, 2007, vol. 63, # 33, p. 7906 - 7915]
[8]Duan, Peng-Cheng; Jin, Rui-Wen; Wang, Zi-Xuan; Yang, Guang [Journal of Chemical Crystallography, 2013, vol. 43, # 8, p. 448 - 454]
[9]Duan, Peng-Cheng; Wang, Zhao-Yang; Chen, Jing-Huo; Yang, Guang; Raptis, Raphael G. [Dalton Transactions, 2013, vol. 42, # 42, p. 14951 - 14954]
[10]Rodriguez, Alice L.; Tamrazi, Anobel; Collins, Margaret L.; Katzenellenbogen, John A. [Journal of Medicinal Chemistry, 2004, vol. 47, # 3, p. 600 - 611]
[11]Sakyiamah, Maxwell M.; Kobayakawa, Takuya; Fujino, Masayuki; Konno, Makoto; Narumi, Tetsuo; Tanaka, Tomohiro; Nomura, Wataru; Yamamoto, Naoki; Murakami, Tsutomu; Tamamura, Hirokazu [Bioorganic and Medicinal Chemistry, 2019, vol. 27, # 6, p. 1130 - 1138]
[12]Terfort, Andreas; Goerls, Helmar; Brunner, Henri [Synthesis, 1997, # 1, p. 79 - 86]
[13]Lee, Yeo Ran; Kim, YoungSoo; Yoo, Kyung Ho [Bulletin of the Korean Chemical Society, 2015, vol. 36, # 1, p. 413 - 416]
[14]Schaack, Cédric; Sidler, Eric; Trapp, Nils; Diederich, François [Chemistry - A European Journal, 2017, vol. 23, # 57, p. 14153 - 14157]
[15]Bencze, Eva Szusanna; Zonta, Cristiano; Mancin, Fabrizio; Prins, Leonard J.; Scrimin, Paolo [European Journal of Organic Chemistry, 2018, vol. 2018, # 39, p. 5375 - 5381]
[16]Higashi, Toshinori; Uemura, Koichi; Inami, Keiko; Mochizuki, Masataka [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 10, p. 3568 - 3571]
[17]Current Patent Assignee: GLAXOSMITHKLINE PLC; UNIVERSITY OF NORTH CAROLINA SYSTEM - WO2020/110056, 2020, A1 Location in patent: Page/Page column 242
[18]Borkent,J.H.; Laarhoven,W.H. [Tetrahedron, 1978, vol. 34, p. 2565 - 2567]
[19]Katz,T.J.; Slusarek,W. [Journal of the American Chemical Society, 1979, vol. 101, p. 4259 - 4267]
[20]Sato,T. et al. [Journal of the Chemical Society. Perkin transactions I, 1976, p. 2051 - 2054]
[21]Park, Hyeung-Geun; Jeong, Byeong-Seon; Yoo, Mi-Sook; Lee, Jeong-Hee; Park, Mi-Kyoung; Lee, Yeon-Ju; Kim, Mi-Jeong; Jew, Sang-Sup [Angewandte Chemie - International Edition, 2002, vol. 41, # 16, p. 3036 - 3038]
[22]Wong, Wallace W. H.; Curiel, David; Cowley, Andrew R.; Beer, Paul D. [Dalton Transactions, 2005, # 2, p. 359 - 364]
[23]Location in patent: experimental part Jones, Peter G.; Kus, Piotr [Zeitschrift fur Naturforschung, B: Chemical Sciences, 2010, vol. 65, # 4, p. 433 - 444]
  • 10
  • [ 582-16-1 ]
  • [ 14748-65-3 ]
YieldReaction ConditionsOperation in experiment
With nitric acid In acetic acid
With nitric acid
Reference： [1]Tavs,P. et al. [Justus Liebigs Annalen der Chemie, 1967, vol. 704, p. 150 - 160]
[2]Klamann,D.; Kraemer,U. [Chemische Berichte, 1960, vol. 93, p. 2316 - 2325]
  • 11
  • [ 582-16-1 ]
  • 2,7-Dimethyl-1,4-dihydronaphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With C8K In tetrahydrofuran at 0℃;
Reference： [1]Weitz, Iris S.; Rabinovitz, Mordecai [Journal of the Chemical Society. Perkin transactions I, 1993, # 1, p. 117 - 120]
  • 12
  • [ 582-16-1 ]
  • [ 2089-89-6 ]
YieldReaction ConditionsOperation in experiment
With sodium dichromate In water
With sodium dichromate In water at 250℃;
Reference： [1]Fujishiro, Koichi; Mitamura, Shuichi [Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 3, p. 786 - 790]
[2]Tan, Wei Hua; Niino, Noriaki; Ishikura, Takahiro; Maruta, Aya; Yamamoto, Tatsuyuki; Matsui, Yoshihisa [Bulletin of the Chemical Society of Japan, 1998, vol. 71, # 6, p. 1285 - 1292]
  • 13
  • [ 582-16-1 ]
  • [ 66778-18-5 ]
YieldReaction ConditionsOperation in experiment
With air; trifluorormethanesulfonic acid; sodium nitrite In acetonitrile at -40℃; for 1h; Yield given;
Reference： [1]Tanaka, Mutsuo; Nakashima, Hideki; Fujiwara, Masahiro; Ando, Hisanori; Souma, Yoshie [Journal of Organic Chemistry, 1996, vol. 61, # 2, p. 788 - 792]
  • 14
  • 2-Methyl-4,4-bis-methylsulfanyl-1-m-tolyl-butan-2-ol [ No CAS ]
  • [ 582-16-1 ]
YieldReaction ConditionsOperation in experiment
With boron trifluoride diethyl etherate In benzene for 0.5h; Heating; Yield given;
Reference： [1]Yadav, K. Mallik; Mohanta, Pramod K.; Ila, Hiriyakkanavar; Junjappa, Hiriyakkanavar [Tetrahedron, 1996, vol. 52, # 44, p. 14049 - 14056]
  • 15
  • [ 85-44-9 ]
  • [ 582-16-1 ]
  • [ 860596-39-0 ]
YieldReaction ConditionsOperation in experiment
With aluminium trichloride; 1,1,2,2-tetrachloroethane
Reference： [1]Fieser; Peters [Journal of the American Chemical Society, 1932, vol. 54, p. 3742,3750] Fieser; Fieser [Journal of the American Chemical Society, 1933, vol. 55, p. 3342,3351]
  • 16
  • [ 582-16-1 ]
  • [ 5159-64-8 ]
YieldReaction ConditionsOperation in experiment
With 1,4-dihydronicotinamide adenine dinucleotide; Pseudomonas putida 1013; tris hydrochloride In N,N-dimethyl-formamide for 24h;
Reference： [1]Khadikar, Padmakar V; Pathre, Sadanand V; Shrivastava, Anjali [Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 19, p. 2673 - 2680]
  • 17
  • [ 79-37-8 ]
  • [ 582-16-1 ]
  • [ 146885-81-6 ]
  • 4,7-dimethylacenaphthylene-1,2-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 53% 2: 3% With aluminum tri-bromide In dichloromethane for 4h; cooling;
1: 37% 2: 9% With aluminum tri-bromide In dichloromethane at -16℃; for 4h;
Stage #1: oxalyl dichloride; 2,7-dimethylnaphthalene With aluminum tri-bromide In dichloromethane at -40 - -15℃; for 4h; Large scale reaction; Stage #2: Large scale reaction;
With aluminium bromide In dichloromethane at -15℃; for 8h;
With aluminum tri-bromide In dichloromethane at -15℃; for 8h;

Reference： [1]Mori, Tadashi; Grimme, Stefan; Inoue, Yoshihisa [Journal of Organic Chemistry, 2007, vol. 72, # 18, p. 6998 - 7010]
[2]Jones, Carissa S.; Elliott, Eric; Siegel, Jay S. [Synlett, 2004, # 1, p. 187 - 191]
[3]Location in patent: experimental part Butterfield, Anna M.; Gilomen, Bruno; Siegel, Jay S. [Organic Process Research and Development, 2012, vol. 16, # 4, p. 664 - 676]
[4]Rice, Allison M.; Fellows, W. Brett; Dolgopolova, Ekaterina A.; Greytak, Andrew B.; Vannucci, Aaron K.; Smith, Mark D.; Karakalos, Stavros G.; Krause, Jeanette A.; Avdoshenko, Stanislav M.; Popov, Alexey A.; Shustova, Natalia B. [Angewandte Chemie - International Edition, 2017, vol. 56, # 16, p. 4525 - 4529][Angew. Chem., 2017, vol. 129, # 16, p. 4596 - 4600,5]
[5]Rice, Allison M.; Dolgopolova, Ekaterina A.; Yarbrough, Brandon J.; Leith, Gabrielle A.; Martin, Corey R.; Stephenson, Kenneth S.; Heugh, Rebecca A.; Brandt, Amy J.; Chen, Donna A.; Karakalos, Stavros G.; Smith, Mark D.; Hatzell, Kelsey B.; Pellechia, Perry J.; Garashchuk, Sophya; Shustova, Natalia B. [Angewandte Chemie - International Edition, 2018, vol. 57, # 35, p. 11310 - 11315][Angew. Chem., 2018, vol. 130, p. 11480 - 11485,6]
  • 18
  • [ 582-16-1 ]
  • [ 37558-62-6 ]
  • 1,8-dibromo-2,7-dimethylnaphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 5% 2: 85% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 48h;
Reference： [1]Larkem; Larkem; Messadi [Egyptian Journal of Chemistry, 2004, vol. 47, # 4, p. 413 - 426]
  • 19
  • [ 582-16-1 ]
  • [ 130614-80-1 ]
  • C24H19Cl3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 54% 2: 40% With sulfuryl dichloride; benzyl peroxide In tetrachloromethane for 18h; Heating;
Reference： [1]Larkem; Larkem; Messadi [Egyptian Journal of Chemistry, 2004, vol. 47, # 4, p. 413 - 426]
  • 20
  • [ 582-16-1 ]
  • 2,7-bis(hydrocinchonidinium-N-methyl)naphthalene dibromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 88 percent / N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CCl4 / 0.17 h / Heating 2: 97 percent / dimethylformamide; ethanol; CHCl3 / 6 h / 100 °C
Reference： [1]Lee, Jeong-Hee; Yoo, Mi-Sook; Jung, Ji-Hee; Jew, Sang-sup; Park, Hyeung-geun; Jeong, Byeong-Seon [Tetrahedron, 2007, vol. 63, # 33, p. 7906 - 7915]
  • 21
  • [ 582-16-1 ]
  • 2,7-bis(hydrocinchoninium-N-methyl) naphthalene dibromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 88 percent / N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CCl4 / 0.17 h / Heating 2: 94 percent / dimethylformamide; ethanol; CHCl3 / 100 °C
Reference： [1]Lee, Jeong-Hee; Yoo, Mi-Sook; Jung, Ji-Hee; Jew, Sang-sup; Park, Hyeung-geun; Jeong, Byeong-Seon [Tetrahedron, 2007, vol. 63, # 33, p. 7906 - 7915]
  • 22
  • [ 582-16-1 ]
  • 2,7-bis[O(9)-allylhydrocinchonidinium-N-methyl]naphthalene dibromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 88 percent / N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CCl4 / 0.17 h / Heating 2: 97 percent / dimethylformamide; ethanol; CHCl3 / 6 h / 100 °C 3: 95 percent / KOH / CH2Cl2; H2O / 4 h / 20 °C
Reference： [1]Lee, Jeong-Hee; Yoo, Mi-Sook; Jung, Ji-Hee; Jew, Sang-sup; Park, Hyeung-geun; Jeong, Byeong-Seon [Tetrahedron, 2007, vol. 63, # 33, p. 7906 - 7915]
  • 23
  • [ 582-16-1 ]
  • 2,7-bis[O(9)-allylhydrocinchoninium-N-methyl]naphthalene dibromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 88 percent / N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CCl4 / 0.17 h / Heating 2: 94 percent / dimethylformamide; ethanol; CHCl3 / 100 °C 3: 92 percent / KOH / CH2Cl2; H2O / 20 °C
Reference： [1]Lee, Jeong-Hee; Yoo, Mi-Sook; Jung, Ji-Hee; Jew, Sang-sup; Park, Hyeung-geun; Jeong, Byeong-Seon [Tetrahedron, 2007, vol. 63, # 33, p. 7906 - 7915]
  • 24
  • [ 582-16-1 ]
  • 2,7-bis(cinchonidinium-N-methyl)naphthalene dibromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 88 percent / N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CCl4 / 0.17 h / Heating 2: dimethylformamide; ethanol; CHCl3
Reference： [1]Lee, Jeong-Hee; Yoo, Mi-Sook; Jung, Ji-Hee; Jew, Sang-sup; Park, Hyeung-geun; Jeong, Byeong-Seon [Tetrahedron, 2007, vol. 63, # 33, p. 7906 - 7915]
  • 25
  • [ 582-16-1 ]
  • 2,7-bis[9(O)-allylcinchonidinium-N-methyl]naphthalene dibromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 88 percent / N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CCl4 / 0.17 h / Heating 2: dimethylformamide; ethanol; CHCl3 3: KOH / CH2Cl2; H2O / 20 °C
Reference： [1]Lee, Jeong-Hee; Yoo, Mi-Sook; Jung, Ji-Hee; Jew, Sang-sup; Park, Hyeung-geun; Jeong, Byeong-Seon [Tetrahedron, 2007, vol. 63, # 33, p. 7906 - 7915]
  • 26
  • [ 582-16-1 ]
  • [ 852540-87-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 98 percent / N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CCl4 / 9 h / 80 °C 2: 28 percent / CaCO3; water / dioxane / 9 h / 90 °C 3: 80 percent / imidazole / dimethylformamide / 1 h
Reference： [1]Minami, Atsushi; Uchida, Rei; Eguchi, Tadashi; Kakinuma, Katsumi [Journal of the American Chemical Society, 2005, vol. 127, # 17, p. 6148 - 6149]
  • 27
  • [ 582-16-1 ]
  • <i>tert</i>-butyl-dimethyl-(7-phenylsulfanylmethyl-naphthalen-2-ylmethoxy)-silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 98 percent / N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CCl4 / 9 h / 80 °C 2: 28 percent / CaCO3; water / dioxane / 9 h / 90 °C 3: 80 percent / imidazole / dimethylformamide / 1 h 4: K2CO3 / dimethylformamide / 1 h / 20 °C
Reference： [1]Minami, Atsushi; Uchida, Rei; Eguchi, Tadashi; Kakinuma, Katsumi [Journal of the American Chemical Society, 2005, vol. 127, # 17, p. 6148 - 6149]
  • 28
  • [ 582-16-1 ]
  • [ 852540-88-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 98 percent / N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CCl4 / 9 h / 80 °C 2: 28 percent / CaCO3; water / dioxane / 9 h / 90 °C 3: 80 percent / imidazole / dimethylformamide / 1 h 4: K2CO3 / dimethylformamide / 1 h / 20 °C 5: 266 mg / mCPBA / CH2Cl2 / 0.5 h
Reference： [1]Minami, Atsushi; Uchida, Rei; Eguchi, Tadashi; Kakinuma, Katsumi [Journal of the American Chemical Society, 2005, vol. 127, # 17, p. 6148 - 6149]
  • 29
  • [ 582-16-1 ]
  • [ 852540-95-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 14 steps 1.1: 98 percent / N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CCl4 / 9 h / 80 °C 2.1: 28 percent / CaCO3; water / dioxane / 9 h / 90 °C 3.1: 80 percent / imidazole / dimethylformamide / 1 h 4.1: K2CO3 / dimethylformamide / 1 h / 20 °C 5.1: 266 mg / mCPBA / CH2Cl2 / 0.5 h 6.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 6.2: 80 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C 7.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C 8.1: 88 percent / SmI2 / tetrahydrofuran / 0.25 h / -20 °C 9.1: 87 percent / HF*pyridine / tetrahydrofuran / 0.08 h / 0 °C 10.1: MnO2 / CH2Cl2 / 1 h / 20 °C 11.1: 1.57 g / 2-methyl-2-butene; NaH2PO4; aq. NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C 12.1: aq. HCl / methanol / 72 h / 20 °C 13.1: 321 mg / (EtO)2P(=O)CN; Et3N / dimethylformamide / 2 h / 20 °C 14.1: 75 percent / NaBH4 / methanol; dioxane / 1 h / 20 °C
Reference： [1]Minami, Atsushi; Uchida, Rei; Eguchi, Tadashi; Kakinuma, Katsumi [Journal of the American Chemical Society, 2005, vol. 127, # 17, p. 6148 - 6149]
  • 30
  • [ 582-16-1 ]
  • [ 852540-94-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1.1: 98 percent / N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CCl4 / 9 h / 80 °C 2.1: 28 percent / CaCO3; water / dioxane / 9 h / 90 °C 3.1: 80 percent / imidazole / dimethylformamide / 1 h 4.1: K2CO3 / dimethylformamide / 1 h / 20 °C 5.1: 266 mg / mCPBA / CH2Cl2 / 0.5 h 6.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 6.2: 80 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C 7.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C 8.1: 88 percent / SmI2 / tetrahydrofuran / 0.25 h / -20 °C 9.1: 87 percent / HF*pyridine / tetrahydrofuran / 0.08 h / 0 °C 10.1: MnO2 / CH2Cl2 / 1 h / 20 °C 11.1: 1.57 g / 2-methyl-2-butene; NaH2PO4; aq. NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C 12.1: aq. HCl / methanol / 72 h / 20 °C 13.1: 321 mg / (EtO)2P(=O)CN; Et3N / dimethylformamide / 2 h / 20 °C
Reference： [1]Minami, Atsushi; Uchida, Rei; Eguchi, Tadashi; Kakinuma, Katsumi [Journal of the American Chemical Society, 2005, vol. 127, # 17, p. 6148 - 6149]
  • 31
  • [ 582-16-1 ]
  • [ 852540-93-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1.1: 98 percent / N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CCl4 / 9 h / 80 °C 2.1: 28 percent / CaCO3; water / dioxane / 9 h / 90 °C 3.1: 80 percent / imidazole / dimethylformamide / 1 h 4.1: K2CO3 / dimethylformamide / 1 h / 20 °C 5.1: 266 mg / mCPBA / CH2Cl2 / 0.5 h 6.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 6.2: 80 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C 7.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C 8.1: 88 percent / SmI2 / tetrahydrofuran / 0.25 h / -20 °C 9.1: 87 percent / HF*pyridine / tetrahydrofuran / 0.08 h / 0 °C 10.1: MnO2 / CH2Cl2 / 1 h / 20 °C 11.1: 1.57 g / 2-methyl-2-butene; NaH2PO4; aq. NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C 12.1: aq. HCl / methanol / 72 h / 20 °C
Reference： [1]Minami, Atsushi; Uchida, Rei; Eguchi, Tadashi; Kakinuma, Katsumi [Journal of the American Chemical Society, 2005, vol. 127, # 17, p. 6148 - 6149]
  • 32
  • [ 582-16-1 ]
  • (3-{3-[5-(7-formyl-naphthalen-2-yl)-4-oxo-pentyl]-phenyl}-propyl)-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: 98 percent / N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CCl4 / 9 h / 80 °C 2.1: 28 percent / CaCO3; water / dioxane / 9 h / 90 °C 3.1: 80 percent / imidazole / dimethylformamide / 1 h 4.1: K2CO3 / dimethylformamide / 1 h / 20 °C 5.1: 266 mg / mCPBA / CH2Cl2 / 0.5 h 6.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 6.2: 80 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C 7.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C 8.1: 88 percent / SmI2 / tetrahydrofuran / 0.25 h / -20 °C 9.1: 87 percent / HF*pyridine / tetrahydrofuran / 0.08 h / 0 °C 10.1: MnO2 / CH2Cl2 / 1 h / 20 °C
Reference： [1]Minami, Atsushi; Uchida, Rei; Eguchi, Tadashi; Kakinuma, Katsumi [Journal of the American Chemical Society, 2005, vol. 127, # 17, p. 6148 - 6149]
  • 33
  • [ 582-16-1 ]
  • [ 852541-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: 98 percent / N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CCl4 / 9 h / 80 °C 2.1: 28 percent / CaCO3; water / dioxane / 9 h / 90 °C 3.1: 80 percent / imidazole / dimethylformamide / 1 h 4.1: K2CO3 / dimethylformamide / 1 h / 20 °C 5.1: 266 mg / mCPBA / CH2Cl2 / 0.5 h 6.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 6.2: 80 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C 7.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C 8.1: 88 percent / SmI2 / tetrahydrofuran / 0.25 h / -20 °C 9.1: 87 percent / HF*pyridine / tetrahydrofuran / 0.08 h / 0 °C
Reference： [1]Minami, Atsushi; Uchida, Rei; Eguchi, Tadashi; Kakinuma, Katsumi [Journal of the American Chemical Society, 2005, vol. 127, # 17, p. 6148 - 6149]
  • 34
  • [ 582-16-1 ]
  • [ 852540-92-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1.1: 98 percent / N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CCl4 / 9 h / 80 °C 2.1: 28 percent / CaCO3; water / dioxane / 9 h / 90 °C 3.1: 80 percent / imidazole / dimethylformamide / 1 h 4.1: K2CO3 / dimethylformamide / 1 h / 20 °C 5.1: 266 mg / mCPBA / CH2Cl2 / 0.5 h 6.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 6.2: 80 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C 7.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C 8.1: 88 percent / SmI2 / tetrahydrofuran / 0.25 h / -20 °C 9.1: 87 percent / HF*pyridine / tetrahydrofuran / 0.08 h / 0 °C 10.1: MnO2 / CH2Cl2 / 1 h / 20 °C 11.1: 1.57 g / 2-methyl-2-butene; NaH2PO4; aq. NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C
Reference： [1]Minami, Atsushi; Uchida, Rei; Eguchi, Tadashi; Kakinuma, Katsumi [Journal of the American Chemical Society, 2005, vol. 127, # 17, p. 6148 - 6149]
  • 35
  • [ 582-16-1 ]
  • C32H40N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 15 steps 1.1: 98 percent / N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CCl4 / 9 h / 80 °C 2.1: 28 percent / CaCO3; water / dioxane / 9 h / 90 °C 3.1: 80 percent / imidazole / dimethylformamide / 1 h 4.1: K2CO3 / dimethylformamide / 1 h / 20 °C 5.1: 266 mg / mCPBA / CH2Cl2 / 0.5 h 6.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 6.2: 80 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C 7.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C 8.1: 88 percent / SmI2 / tetrahydrofuran / 0.25 h / -20 °C 9.1: 87 percent / HF*pyridine / tetrahydrofuran / 0.08 h / 0 °C 10.1: MnO2 / CH2Cl2 / 1 h / 20 °C 11.1: 1.57 g / 2-methyl-2-butene; NaH2PO4; aq. NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C 12.1: aq. HCl / methanol / 72 h / 20 °C 13.1: 321 mg / (EtO)2P(=O)CN; Et3N / dimethylformamide / 2 h / 20 °C 14.1: 75 percent / NaBH4 / methanol; dioxane / 1 h / 20 °C 15.1: Tris-HCl; VinC / dimethylsulfoxide / 1.5 h / 28 °C / pH 8.0
Reference： [1]Minami, Atsushi; Uchida, Rei; Eguchi, Tadashi; Kakinuma, Katsumi [Journal of the American Chemical Society, 2005, vol. 127, # 17, p. 6148 - 6149]
  • 36
  • [ 582-16-1 ]
  • [ 852540-91-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: 98 percent / N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CCl4 / 9 h / 80 °C 2.1: 28 percent / CaCO3; water / dioxane / 9 h / 90 °C 3.1: 80 percent / imidazole / dimethylformamide / 1 h 4.1: K2CO3 / dimethylformamide / 1 h / 20 °C 5.1: 266 mg / mCPBA / CH2Cl2 / 0.5 h 6.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 6.2: 80 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C 7.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C 8.1: 88 percent / SmI2 / tetrahydrofuran / 0.25 h / -20 °C
Reference： [1]Minami, Atsushi; Uchida, Rei; Eguchi, Tadashi; Kakinuma, Katsumi [Journal of the American Chemical Society, 2005, vol. 127, # 17, p. 6148 - 6149]
  • 37
  • [ 582-16-1 ]
  • [ 852540-89-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 98 percent / N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CCl4 / 9 h / 80 °C 2.1: 28 percent / CaCO3; water / dioxane / 9 h / 90 °C 3.1: 80 percent / imidazole / dimethylformamide / 1 h 4.1: K2CO3 / dimethylformamide / 1 h / 20 °C 5.1: 266 mg / mCPBA / CH2Cl2 / 0.5 h 6.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 6.2: 80 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C
Reference： [1]Minami, Atsushi; Uchida, Rei; Eguchi, Tadashi; Kakinuma, Katsumi [Journal of the American Chemical Society, 2005, vol. 127, # 17, p. 6148 - 6149]
  • 38
  • [ 582-16-1 ]
  • [ 852540-90-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: 98 percent / N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CCl4 / 9 h / 80 °C 2.1: 28 percent / CaCO3; water / dioxane / 9 h / 90 °C 3.1: 80 percent / imidazole / dimethylformamide / 1 h 4.1: K2CO3 / dimethylformamide / 1 h / 20 °C 5.1: 266 mg / mCPBA / CH2Cl2 / 0.5 h 6.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 6.2: 80 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C 7.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C
Reference： [1]Minami, Atsushi; Uchida, Rei; Eguchi, Tadashi; Kakinuma, Katsumi [Journal of the American Chemical Society, 2005, vol. 127, # 17, p. 6148 - 6149]
  • 39
  • [ 582-16-1 ]
  • [ 852540-86-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 98 percent / N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CCl4 / 9 h / 80 °C 2: 28 percent / CaCO3; water / dioxane / 9 h / 90 °C
Reference： [1]Minami, Atsushi; Uchida, Rei; Eguchi, Tadashi; Kakinuma, Katsumi [Journal of the American Chemical Society, 2005, vol. 127, # 17, p. 6148 - 6149]
  • 40
  • [ 582-16-1 ]
  • 1,8-dibromo-2,7-dimethylnaphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
89.56% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 24h; 1 2,7-Dibromonaphthalene (20 g, 128.02 mmol) was dissolved in DMF (200 mL). Then, NBS (50.1 g, 281.65 mmol) was slowly added at room temperature. After stirring at room temperature for 24 hours, the organic solvent was distilled under reduced pressure. After adding distilled water, extraction with EA yielded Compound 1-1 (36 g, 114.64 mmol, 89.56 %).
62.2% With N-Bromosuccinimide In N,N-dimethyl-formamide for 24h; 1.2 2) Synthesis of Compound 2 Compound 1 (10 g, 64.1 mmol) was dissolved in N, N-dimethylformamide (100 mL), and then N-bromo succineimide (2.1eq, 23.9 g) was added thereto, followed by stirring for 24 hours. product was obtained and purified using column chromatography. fig.4 shows an NMR measurement graph of Compound 2.Yield = 12.5 g (62.2%), Purity = 98.1%
Multi-step reaction with 2 steps 1: 71 percent / NBS / dimethylformamide / 20 °C 2: 70 percent / NBS / dimethylformamide / 24 h / 20 °C
Multi-step reaction with 2 steps 1: 85 percent / NBS / dimethylformamide / 48 h / 20 °C 2: 70 percent / NBS / dimethylformamide / 24 h / 20 °C
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 20 °C / Schlenk technique; Inert atmosphere 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 288 h / 20 °C / Schlenk technique; Inert atmosphere

Reference： [1]Current Patent Assignee: DOW INC - WO2010/151006, 2010, A1 Location in patent: Page/Page column 17
[2]Current Patent Assignee: LG CHEM CO.,LTD. - KR2019/117242, 2019, A Location in patent: Paragraph 0307-0308; 0316-0320
[3]Larkem; Larkem; Messadi [Egyptian Journal of Chemistry, 2004, vol. 47, # 4, p. 413 - 426]
[4]Larkem; Larkem; Messadi [Egyptian Journal of Chemistry, 2004, vol. 47, # 4, p. 413 - 426]
[5]González-Fernández, Elisa; Nicholls, Leo D.M.; Schaaf, Lukas D.; Farès, Christophe; Lehmann, Christian W.; Alcarazo, Manuel [Journal of the American Chemical Society, 2017, vol. 139, # 4, p. 1428 - 1431]
  • 41
  • [ 582-16-1 ]
  • 10,21-dibromo-2,13-dithia[3.3](2,7)naphthalenophane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 71 percent / NBS / dimethylformamide / 20 °C 2: 95 percent / NBS; benzoyl peroxide / CCl4 / 3 h / Heating 3: 82 percent / NaOH / ethanol; toluene / 20 h / Heating
Multi-step reaction with 5 steps 1: 71 percent / NBS / dimethylformamide / 20 °C 2: 95 percent / NBS; benzoyl peroxide / CCl4 / 3 h / Heating 3: 99 percent / ethanol / 2 h / Heating 4: 83 percent / aq. NaOH / 0.75 h / Heating 5: 82 percent / NaOH / ethanol; toluene / 20 h / Heating
Multi-step reaction with 3 steps 1: 85 percent / NBS / dimethylformamide / 48 h / 20 °C 2: 95 percent / NBS; benzoyl peroxide / CCl4 / 3 h / Heating 3: 82 percent / NaOH / ethanol; toluene / 20 h / Heating
Multi-step reaction with 5 steps 1: 85 percent / NBS / dimethylformamide / 48 h / 20 °C 2: 95 percent / NBS; benzoyl peroxide / CCl4 / 3 h / Heating 3: 99 percent / ethanol / 2 h / Heating 4: 83 percent / aq. NaOH / 0.75 h / Heating 5: 82 percent / NaOH / ethanol; toluene / 20 h / Heating

Reference： [1]Larkem; Larkem; Messadi [Egyptian Journal of Chemistry, 2004, vol. 47, # 4, p. 413 - 426]
[2]Larkem; Larkem; Messadi [Egyptian Journal of Chemistry, 2004, vol. 47, # 4, p. 413 - 426]
[3]Larkem; Larkem; Messadi [Egyptian Journal of Chemistry, 2004, vol. 47, # 4, p. 413 - 426]
[4]Larkem; Larkem; Messadi [Egyptian Journal of Chemistry, 2004, vol. 47, # 4, p. 413 - 426]
  • 42
  • [ 582-16-1 ]
  • [ 847050-57-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NBS; AIBN / CCl4
Reference： [1]Wong, Wallace W. H.; Curiel, David; Cowley, Andrew R.; Beer, Paul D. [Dalton Transactions, 2005, # 2, p. 359 - 364]
  • 43
  • [ 582-16-1 ]
  • [ 56137-97-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 62 percent / HCl; AcOH 2: 99 percent / acetone 3: 90 percent / H2SO4; AcOH 4: 82 percent / SOCl2; AlCl3 / CH2Cl2
Multi-step reaction with 4 steps 1: 62 percent / HCl(g); AcOH 2: 99 percent / acetone 3: 90 percent / aq. H2SO4; AcOH 4: 82 percent / SOCl2; AlCl3 / CH2Cl2
Multi-step reaction with 5 steps 1: 62 percent / HCl, acetic acid / 24 h / 50 °C 2: 99 percent / acetone; H2O / 12 h / Heating 3: 90 percent / H2SO4, acetic acid / H2O / 6 h / Heating 4: SOCl2 / CHCl3 / 1 h / Heating 5: AlCl3 / nitrobenzene / 48 h / Ambient temperature
Reference： [1]Jones, Carissa S.; Elliott, Eric; Siegel, Jay S. [Synlett, 2004, # 1, p. 187 - 191]
[2]Seiders, T. Jon; Elliott, Eric L.; Grube, Gunther H.; Siegel, Jay S. [Journal of the American Chemical Society, 1999, vol. 121, # 34, p. 7804 - 7813]
[3]Borchardt, Allen; Hardcastle, Kenneth; Gantzel, Peter; Siegel, Jay S. [Tetrahedron Letters, 1993, vol. 34, # 2, p. 273 - 276]
  • 44
  • [ 582-16-1 ]
  • [ 56137-96-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 62 percent / HCl; AcOH 2: 99 percent / acetone 3: 90 percent / H2SO4; AcOH
Multi-step reaction with 3 steps 1: 62 percent / HCl(g); AcOH 2: 99 percent / acetone 3: 90 percent / aq. H2SO4; AcOH
Multi-step reaction with 3 steps 1: 62 percent / HCl, acetic acid / 24 h / 50 °C 2: 99 percent / acetone; H2O / 12 h / Heating 3: 90 percent / H2SO4, acetic acid / H2O / 6 h / Heating
Reference： [1]Jones, Carissa S.; Elliott, Eric; Siegel, Jay S. [Synlett, 2004, # 1, p. 187 - 191]
[2]Seiders, T. Jon; Elliott, Eric L.; Grube, Gunther H.; Siegel, Jay S. [Journal of the American Chemical Society, 1999, vol. 121, # 34, p. 7804 - 7813]
[3]Borchardt, Allen; Hardcastle, Kenneth; Gantzel, Peter; Siegel, Jay S. [Tetrahedron Letters, 1993, vol. 34, # 2, p. 273 - 276]
  • 45
  • [ 582-16-1 ]
  • [ 246874-32-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 62 percent / HCl; AcOH 2: 99 percent / acetone
Multi-step reaction with 2 steps 1: 62 percent / HCl(g); AcOH 2: 99 percent / acetone
Multi-step reaction with 2 steps 1: 62 percent / HCl, acetic acid / 24 h / 50 °C 2: 99 percent / acetone; H2O / 12 h / Heating
Reference： [1]Jones, Carissa S.; Elliott, Eric; Siegel, Jay S. [Synlett, 2004, # 1, p. 187 - 191]
[2]Seiders, T. Jon; Elliott, Eric L.; Grube, Gunther H.; Siegel, Jay S. [Journal of the American Chemical Society, 1999, vol. 121, # 34, p. 7804 - 7813]
[3]Borchardt, Allen; Hardcastle, Kenneth; Gantzel, Peter; Siegel, Jay S. [Tetrahedron Letters, 1993, vol. 34, # 2, p. 273 - 276]
  • 46
  • [ 582-16-1 ]
  • [ 146885-81-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 62 percent / HCl; AcOH 2: 99 percent / acetone 3: 90 percent / H2SO4; AcOH 4: 82 percent / SOCl2; AlCl3 / CH2Cl2 5: 84 percent / SeO2 / dioxane; H2O
Multi-step reaction with 5 steps 1: 62 percent / HCl(g); AcOH 2: 99 percent / acetone 3: 90 percent / aq. H2SO4; AcOH 4: 82 percent / SOCl2; AlCl3 / CH2Cl2 5: 84 percent / SeO2 / dioxane; H2O
Multi-step reaction with 6 steps 1: 62 percent / HCl, acetic acid / 24 h / 50 °C 2: 99 percent / acetone; H2O / 12 h / Heating 3: 90 percent / H2SO4, acetic acid / H2O / 6 h / Heating 4: SOCl2 / CHCl3 / 1 h / Heating 5: AlCl3 / nitrobenzene / 48 h / Ambient temperature 6: 91 percent / SeO2 / dioxane; H2O / 48 h / 60 °C
Reference： [1]Jones, Carissa S.; Elliott, Eric; Siegel, Jay S. [Synlett, 2004, # 1, p. 187 - 191]
[2]Seiders, T. Jon; Elliott, Eric L.; Grube, Gunther H.; Siegel, Jay S. [Journal of the American Chemical Society, 1999, vol. 121, # 34, p. 7804 - 7813]
[3]Borchardt, Allen; Hardcastle, Kenneth; Gantzel, Peter; Siegel, Jay S. [Tetrahedron Letters, 1993, vol. 34, # 2, p. 273 - 276]
  • 47
  • [ 582-16-1 ]
  • C26H26 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 62 percent / HCl; AcOH 2.1: Mg / tetrahydrofuran / 3 h / Heating 2.2: 45 percent / BaCO3 / tetrahydrofuran / Heating
Reference： [1]Jones, Carissa S.; Elliott, Eric; Siegel, Jay S. [Synlett, 2004, # 1, p. 187 - 191]
  • 48
  • [ 582-16-1 ]
  • [ 656822-42-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 71 percent / N-bromosuccinimide; benzoyl peroxide / CCl4 / 4.5 h / Heating 2: 94 percent / ethanol; H2O / 2 h / Heating
Reference： [1]Rodriguez, Alice L.; Tamrazi, Anobel; Collins, Margaret L.; Katzenellenbogen, John A. [Journal of Medicinal Chemistry, 2004, vol. 47, # 3, p. 600 - 611]
  • 49
  • [ 582-16-1 ]
  • [ 656822-43-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 71 percent / N-bromosuccinimide; benzoyl peroxide / CCl4 / 4.5 h / Heating 2: 94 percent / ethanol; H2O / 2 h / Heating 3: 36 percent / BH3*THF / tetrahydrofuran / 1 h / Heating
Reference： [1]Rodriguez, Alice L.; Tamrazi, Anobel; Collins, Margaret L.; Katzenellenbogen, John A. [Journal of Medicinal Chemistry, 2004, vol. 47, # 3, p. 600 - 611]
  • 50
  • [ 582-16-1 ]
  • 2,7-bis[2-(3-methylpentanoylamino)ethyl]naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 71 percent / N-bromosuccinimide; benzoyl peroxide / CCl4 / 4.5 h / Heating 2: 94 percent / ethanol; H2O / 2 h / Heating 3: 36 percent / BH3*THF / tetrahydrofuran / 1 h / Heating 4: 73 percent / Et3N / CH2Cl2 / 6 h / Heating
Reference： [1]Rodriguez, Alice L.; Tamrazi, Anobel; Collins, Margaret L.; Katzenellenbogen, John A. [Journal of Medicinal Chemistry, 2004, vol. 47, # 3, p. 600 - 611]
  • 51
  • [ 582-16-1 ]
  • 2,7-bis[2-(4-methylpentanoylamino)ethyl]naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 71 percent / N-bromosuccinimide; benzoyl peroxide / CCl4 / 4.5 h / Heating 2: 94 percent / ethanol; H2O / 2 h / Heating 3: 36 percent / BH3*THF / tetrahydrofuran / 1 h / Heating 4: 45 percent / Et3N / CH2Cl2 / 4 h / Heating
Reference： [1]Rodriguez, Alice L.; Tamrazi, Anobel; Collins, Margaret L.; Katzenellenbogen, John A. [Journal of Medicinal Chemistry, 2004, vol. 47, # 3, p. 600 - 611]
  • 52
  • [ 582-16-1 ]
  • C50H58N4O2(2+)*2Br(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dimethylformamide; ethanol; CHCl3 / 6 h / 100 °C
Reference： [1]Park, Hyeung-Geun; Jeong, Byeong-Seon; Yoo, Mi-Sook; Lee, Jeong-Hee; Park, Mi-Kyoung; Lee, Yeon-Ju; Kim, Mi-Jeong; Jew, Sang-Sup [Angewandte Chemie - International Edition, 2002, vol. 41, # 16, p. 3036 - 3038]
  • 53
  • [ 582-16-1 ]
  • C50H58N4O2(2+)*2Br(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dimethylformamide; ethanol; CHCl3 / 6 h / 100 °C
Reference： [1]Park, Hyeung-Geun; Jeong, Byeong-Seon; Yoo, Mi-Sook; Lee, Jeong-Hee; Park, Mi-Kyoung; Lee, Yeon-Ju; Kim, Mi-Jeong; Jew, Sang-Sup [Angewandte Chemie - International Edition, 2002, vol. 41, # 16, p. 3036 - 3038]
  • 54
  • [ 582-16-1 ]
  • C56H66N4O2(2+)*2Br(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dimethylformamide; ethanol; CHCl3 / 6 h / 100 °C 2: KOH / H2O
Reference： [1]Park, Hyeung-Geun; Jeong, Byeong-Seon; Yoo, Mi-Sook; Lee, Jeong-Hee; Park, Mi-Kyoung; Lee, Yeon-Ju; Kim, Mi-Jeong; Jew, Sang-Sup [Angewandte Chemie - International Edition, 2002, vol. 41, # 16, p. 3036 - 3038]
  • 55
  • [ 582-16-1 ]
  • C56H66N4O2(2+)*2Br(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dimethylformamide; ethanol; CHCl3 / 6 h / 100 °C 2: KOH / H2O
Reference： [1]Park, Hyeung-Geun; Jeong, Byeong-Seon; Yoo, Mi-Sook; Lee, Jeong-Hee; Park, Mi-Kyoung; Lee, Yeon-Ju; Kim, Mi-Jeong; Jew, Sang-Sup [Angewandte Chemie - International Edition, 2002, vol. 41, # 16, p. 3036 - 3038]
  • 56
  • [ 582-16-1 ]
  • [ 5043-18-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Pseudomonas putida 1013; NADH; 0.05M aq. Tris-HCl / dimethylformamide / 24 h / pH 7.5 2: BF3
Reference： [1]Khadikar, Padmakar V; Pathre, Sadanand V; Shrivastava, Anjali [Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 19, p. 2673 - 2680]
  • 57
  • [ 582-16-1 ]
  • [ 146885-82-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 62 percent / HCl(g); AcOH 2: 99 percent / acetone 3: 90 percent / aq. H2SO4; AcOH 4: 82 percent / SOCl2; AlCl3 / CH2Cl2 5: 84 percent / SeO2 / dioxane; H2O 6: KOH / methanol
Multi-step reaction with 7 steps 1: 62 percent / HCl, acetic acid / 24 h / 50 °C 2: 99 percent / acetone; H2O / 12 h / Heating 3: 90 percent / H2SO4, acetic acid / H2O / 6 h / Heating 4: SOCl2 / CHCl3 / 1 h / Heating 5: AlCl3 / nitrobenzene / 48 h / Ambient temperature 6: 91 percent / SeO2 / dioxane; H2O / 48 h / 60 °C 7: 85 percent / KOH / methanol / 0.5 h / Ambient temperature
Multi-step reaction with 2 steps 1.1: aluminum tri-bromide / dichloromethane / 4 h / -40 - -15 °C / Large scale reaction 1.2: 0.5 h / 40 °C / Large scale reaction 1.3: 4 h / 40 °C / Large scale reaction 2.1: potassium hydroxide / methanol / 2 h / 18 - 25 °C / Large scale reaction
Reference： [1]Seiders, T. Jon; Elliott, Eric L.; Grube, Gunther H.; Siegel, Jay S. [Journal of the American Chemical Society, 1999, vol. 121, # 34, p. 7804 - 7813]
[2]Borchardt, Allen; Hardcastle, Kenneth; Gantzel, Peter; Siegel, Jay S. [Tetrahedron Letters, 1993, vol. 34, # 2, p. 273 - 276]
[3]Butterfield, Anna M.; Gilomen, Bruno; Siegel, Jay S. [Organic Process Research and Development, 2012, vol. 16, # 4, p. 664 - 676]
  • 58
  • [ 582-16-1 ]
  • [ 175605-99-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 62 percent / HCl(g); AcOH 2: 99 percent / acetone 3: 90 percent / aq. H2SO4; AcOH 4: 82 percent / SOCl2; AlCl3 / CH2Cl2 5: 84 percent / SeO2 / dioxane; H2O 6: KOH / methanol / 1 h / 20 °C 7: 48 percent / Ac2O / 72 h / 140 °C
Reference： [1]Seiders, T. Jon; Elliott, Eric L.; Grube, Gunther H.; Siegel, Jay S. [Journal of the American Chemical Society, 1999, vol. 121, # 34, p. 7804 - 7813]
  • 59
  • [ 582-16-1 ]
  • [ 175605-98-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: 62 percent / HCl(g); AcOH 2: 99 percent / acetone 3: 90 percent / aq. H2SO4; AcOH 4: 82 percent / SOCl2; AlCl3 / CH2Cl2 5: 84 percent / SeO2 / dioxane; H2O 6: KOH / methanol / 1 h / 20 °C 7: 48 percent / Ac2O / 72 h / 140 °C 8: 100 percent / N-bromosuccinimide; benzoyl peroxide / CCl4 / 6 h / Heating; irradiation 9: 33 percent / TiCl3; LiAlH4 / tetrahydrofuran / 72 h / Heating 10: 70 percent / 2,3-dichloro-5,6-dicyanoquinone / benzene / 1 h / Heating
Reference： [1]Seiders, T. Jon; Elliott, Eric L.; Grube, Gunther H.; Siegel, Jay S. [Journal of the American Chemical Society, 1999, vol. 121, # 34, p. 7804 - 7813]
  • 60
  • [ 582-16-1 ]
  • [ 246874-34-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 62 percent / HCl(g); AcOH 2: 99 percent / acetone 3: 90 percent / aq. H2SO4; AcOH 4: 82 percent / SOCl2; AlCl3 / CH2Cl2 5: 84 percent / SeO2 / dioxane; H2O 6: KOH / methanol / 1 h / 20 °C 7: 48 percent / Ac2O / 72 h / 140 °C 8: 100 percent / N-bromosuccinimide; benzoyl peroxide / CCl4 / 6 h / Heating; irradiation 9: 33 percent / TiCl3; LiAlH4 / tetrahydrofuran / 72 h / Heating
Reference： [1]Seiders, T. Jon; Elliott, Eric L.; Grube, Gunther H.; Siegel, Jay S. [Journal of the American Chemical Society, 1999, vol. 121, # 34, p. 7804 - 7813]
  • 61
  • [ 582-16-1 ]
  • [ 175605-96-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 62 percent / HCl(g); AcOH 2: 99 percent / acetone 3: 90 percent / aq. H2SO4; AcOH 4: 82 percent / SOCl2; AlCl3 / CH2Cl2 5: 84 percent / SeO2 / dioxane; H2O 6: KOH / methanol / 1 h / 20 °C
Reference： [1]Seiders, T. Jon; Elliott, Eric L.; Grube, Gunther H.; Siegel, Jay S. [Journal of the American Chemical Society, 1999, vol. 121, # 34, p. 7804 - 7813]
  • 62
  • [ 582-16-1 ]
  • [ 246874-33-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 62 percent / HCl(g); AcOH 2: 99 percent / acetone 3: 90 percent / aq. H2SO4; AcOH 4: 82 percent / SOCl2; AlCl3 / CH2Cl2 5: 84 percent / SeO2 / dioxane; H2O 6: KOH / methanol / 1 h / 20 °C 7: 48 percent / Ac2O / 72 h / 140 °C 8: 100 percent / N-bromosuccinimide; benzoyl peroxide / CCl4 / 6 h / Heating; irradiation
Reference： [1]Seiders, T. Jon; Elliott, Eric L.; Grube, Gunther H.; Siegel, Jay S. [Journal of the American Chemical Society, 1999, vol. 121, # 34, p. 7804 - 7813]
  • 63
  • [ 582-16-1 ]
  • [ 41784-92-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 64 percent / NBS / acetone / Irradiation 2: 99 percent / dimethylformamide / Ambient temperature
Multi-step reaction with 2 steps 1: NBS
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 80 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere
Reference： [1]Terfort, Andreas; Goerls, Helmar; Brunner, Henri [Synthesis, 1997, # 1, p. 79 - 86]
[2]Borkent,J.H.; Laarhoven,W.H. [Tetrahedron, 1978, vol. 34, p. 2565 - 2567]
[3]Schaack, Cédric; Sidler, Eric; Trapp, Nils; Diederich, François [Chemistry - A European Journal, 2017, vol. 23, # 57, p. 14153 - 14157]
  • 64
  • [ 582-16-1 ]
  • (2,7-Dimethyl-naphthalen-1-yl)-acetyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 62 percent / HCl, acetic acid / 24 h / 50 °C 2: 99 percent / acetone; H2O / 12 h / Heating 3: 90 percent / H2SO4, acetic acid / H2O / 6 h / Heating 4: SOCl2 / CHCl3 / 1 h / Heating
Reference： [1]Borchardt, Allen; Hardcastle, Kenneth; Gantzel, Peter; Siegel, Jay S. [Tetrahedron Letters, 1993, vol. 34, # 2, p. 273 - 276]
  • 65
  • [ 582-16-1 ]
  • [ 73377-85-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 55 percent / CrO3 / acetic acid 2: 65 percent / 30percent H2O2, NaOH / (-)-Benzylquininium chloride / toluene; H2O / 35 - 40 °C
Reference： [1]Pluim, Henk; Wynberg, Hans [Journal of Organic Chemistry, 1980, vol. 45, # 12, p. 2498 - 2502]
  • 66
  • [ 582-16-1 ]
  • [ 71628-24-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (bromination) 2: HMPT / tetrahydrofuran / -78 °C
Reference： [1]Katz,T.J.; Slusarek,W. [Journal of the American Chemical Society, 1979, vol. 101, p. 4259 - 4267]
  • 67
  • [ 582-16-1 ]
  • [ 14827-37-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: HNO3 / acetic acid 2: H2 / Pd-C / 2-methoxy-ethanol
Multi-step reaction with 2 steps 1: HNO3 2: Sn, SnCl2
Reference： [1]Tavs,P. et al. [Justus Liebigs Annalen der Chemie, 1967, vol. 704, p. 150 - 160]
[2]Klamann,D.; Kraemer,U. [Chemische Berichte, 1960, vol. 93, p. 2316 - 2325]
  • 68
  • [ 67-56-1 ]
  • [ 90-12-0 ]
  • [ 91-57-6 ]
  • [ 582-16-1 ]
  • [ 581-42-0 ]
YieldReaction ConditionsOperation in experiment
1: 5.12 %Chromat. 2: 4.44 %Chromat. Stage #1: 1-Methylnaphthalene; 2-Methylnaphthalene at 350℃; for 4h; Stage #2: methanol for 20h; 2 Example 2 (alkylation) Example 2 (alkylation) 153 g of MCM-22 were charged in the tubular reactor (volume: 370 cm3). As a feedstock for alkylation, 1-MMN (purity 95.5%) and 2-MMN (purity 96.6%) were used, and mixed at the molar ratio of 2.2 of 2-MMN/1-MMN. Feedstock was supplied in the reactor (350°C) at the rate of 76.7 g/hr and 0.5 hr-1 in WHSV for 4 hours. Thereafter, methanol was started to be supplied in the reactor at the rate of 17.3 g/hr and the reaction was proceeded for 20 hours. The obtained product was analyzed by gas chromatography, and the result is summarized in Table 2.
Reference： [1]Current Patent Assignee: KOBE STEEL LIMITED; EXXON MOBIL CORP - EP1165473, 2004, B1 Location in patent: Page 8-9
  • 69
  • [ 67-56-1 ]
  • [ 91-57-6 ]
  • [ 582-16-1 ]
  • [ 581-42-0 ]
YieldReaction ConditionsOperation in experiment
at 300℃; for 6h; 2 A down-flow fixed bed reactor was loaded with 0.6 grams of catalyst comprising a mechanical mixture of 0.3 grams of the catalytic material prepared in Example 1 and 0.3 grams of a boehmite binder available as CAPTAPAL B ALUMINA from the Vista Chemical Company of Houston, Tex. The catalyst bed in the reactor was maintained at a temperature of 300° C. during the six-hour test period. Liquid feed containing methanol and 2-MN in a molar ratio of 5:1 was fed to the reactor at a rate of approximately 2 milliliters per hour, and an N2 carrier gas was fed to the reactor at a rate of approximately 20 milliliters per minute. The reactor effluent was analyzed by gas chromatography and yielded the results in Table 1, below.
at 300℃; for 6h; 3 Catalyst was prepared as described in Example 1, except that the solution used to isomorphically substitute iron for aluminum in the ZSM-5 material was prepared by mixing the varying gram amounts of FeF3 and NH4HF2 specified in Table 2 in 100 milliliters of deionized water. Each resulting catalyst exhibited the Fe/Al ratio listed in Table 2. Each catalyst was used to selectively methylate 2-MN as described in Example 2, except where noted to the contrary. The 2-MN conversion and selectivity to 2,6-DMN also are listed in Table 2. A graphical summary of 2-MN conversion, selectivity to 2,6-DMN, the ratio of 2,6-DMN to all DMN's, and the overall yield of 2,6-DMN for Examples 1 through 8 appear in FIGS. 1 through 4.
at 300℃; for 20h; 10 A catalyst according to the present invention having a Fe/Al ratio of 1:4 was prepared as in Example 1. The sample was then used to methylate 2-MN as described in Example 2. We found that the conversion of 2-MN decreased from its initial 15% to 10% after about 20 hours.
at 300℃; for 6h; 4 Catalyst was prepared as described in Example 1, except that the solution used to isomorphically substitute iron for aluminum in the ZSM-5 material was prepared by mixing the varying gram amounts of FeF3 and NH4HF2 specified in Table 2 in 100 milliliters of deionized water. Each resulting catalyst exhibited the Fe/Al ratio listed in Table 2. Each catalyst was used to selectively methylate 2-MN as described in Example 2, except where noted to the contrary. The 2-MN conversion and selectivity to 2,6-DMN also are listed in Table 2. A graphical summary of 2-MN conversion, selectivity to 2,6-DMN, the ratio of 2,6-DMN to all DMN's, and the overall yield of 2,6-DMN for Examples 1 through 8 appear in FIGS. 1 through 4.
at 300℃; for 6h; 5 Catalyst was prepared as described in Example 1, except that the solution used to isomorphically substitute iron for aluminum in the ZSM-5 material was prepared by mixing the varying gram amounts of FeF3 and NH4HF2 specified in Table 2 in 100 milliliters of deionized water. Each resulting catalyst exhibited the Fe/Al ratio listed in Table 2. Each catalyst was used to selectively methylate 2-MN as described in Example 2, except where noted to the contrary. The 2-MN conversion and selectivity to 2,6-DMN also are listed in Table 2. A graphical summary of 2-MN conversion, selectivity to 2,6-DMN, the ratio of 2,6-DMN to all DMN's, and the overall yield of 2,6-DMN for Examples 1 through 8 appear in FIGS. 1 through 4.
at 300℃; for 6h; 6 Catalyst was prepared as described in Example 1, except that the solution used to isomorphically substitute iron for aluminum in the ZSM-5 material was prepared by mixing the varying gram amounts of FeF3 and NH4HF2 specified in Table 2 in 100 milliliters of deionized water. Each resulting catalyst exhibited the Fe/Al ratio listed in Table 2. Each catalyst was used to selectively methylate 2-MN as described in Example 2, except where noted to the contrary. The 2-MN conversion and selectivity to 2,6-DMN also are listed in Table 2. A graphical summary of 2-MN conversion, selectivity to 2,6-DMN, the ratio of 2,6-DMN to all DMN's, and the overall yield of 2,6-DMN for Examples 1 through 8 appear in FIGS. 1 through 4.
at 300℃; for 6h; 8 Catalyst was prepared as described in Example 1, except that the solution used to isomorphically substitute iron for aluminum in the ZSM-5 material was prepared by mixing the varying gram amounts of FeF3 and NH4HF2 specified in Table 2 in 100 milliliters of deionized water. Each resulting catalyst exhibited the Fe/Al ratio listed in Table 2. Each catalyst was used to selectively methylate 2-MN as described in Example 2, except where noted to the contrary. The 2-MN conversion and selectivity to 2,6-DMN also are listed in Table 2. A graphical summary of 2-MN conversion, selectivity to 2,6-DMN, the ratio of 2,6-DMN to all DMN's, and the overall yield of 2,6-DMN for Examples 1 through 8 appear in FIGS. 1 through 4.
at 300℃; for 6h; 7 Catalyst was prepared as described in Example 1, except that the solution used to isomorphically substitute iron for aluminum in the ZSM-5 material was prepared by mixing the varying gram amounts of FeF3 and NH4HF2 specified in Table 2 in 100 milliliters of deionized water. Each resulting catalyst exhibited the Fe/Al ratio listed in Table 2. Each catalyst was used to selectively methylate 2-MN as described in Example 2, except where noted to the contrary. The 2-MN conversion and selectivity to 2,6-DMN also are listed in Table 2. A graphical summary of 2-MN conversion, selectivity to 2,6-DMN, the ratio of 2,6-DMN to all DMN's, and the overall yield of 2,6-DMN for Examples 1 through 8 appear in FIGS. 1 through 4.

Reference： [1]Current Patent Assignee: COMMONWEALTH SYSTEM OF HIGHER EDUCATION - US2005/54889, 2005, A1 Location in patent: Page/Page column 3
[2]Current Patent Assignee: COMMONWEALTH SYSTEM OF HIGHER EDUCATION - US2005/54889, 2005, A1 Location in patent: Page/Page column 3
[3]Current Patent Assignee: COMMONWEALTH SYSTEM OF HIGHER EDUCATION - US2005/54889, 2005, A1 Location in patent: Page/Page column 3
[4]Current Patent Assignee: COMMONWEALTH SYSTEM OF HIGHER EDUCATION - US2005/54889, 2005, A1 Location in patent: Page/Page column 3
[5]Current Patent Assignee: COMMONWEALTH SYSTEM OF HIGHER EDUCATION - US2005/54889, 2005, A1 Location in patent: Page/Page column 3
[6]Current Patent Assignee: COMMONWEALTH SYSTEM OF HIGHER EDUCATION - US2005/54889, 2005, A1 Location in patent: Page/Page column 3
[7]Current Patent Assignee: COMMONWEALTH SYSTEM OF HIGHER EDUCATION - US2005/54889, 2005, A1 Location in patent: Page/Page column 3
[8]Current Patent Assignee: COMMONWEALTH SYSTEM OF HIGHER EDUCATION - US2005/54889, 2005, A1 Location in patent: Page/Page column 3
  • 70
  • [ 573-98-8 ]
  • [ 569-41-5 ]
  • [ 91-20-3 ]
  • [ 581-40-8 ]
  • [ 582-16-1 ]
  • [ 1127-76-0 ]
  • [ 575-43-9 ]
  • [ 581-42-0 ]
  • [ 939-27-5 ]
  • [ 575-37-1 ]
  • [ 575-41-7 ]
  • [ 571-58-4 ]
  • [ 571-61-9 ]
  • [ 90-12-0 ]
  • [ 91-57-6 ]
YieldReaction ConditionsOperation in experiment
1.33%Chromat.; 2.56%Chromat.; 0.36%Chromat.; 1.43%Chromat.; 2.46%Chromat.; 1.56%Chromat.; 0.24%Chromat.; 1.05%Chromat.; 4.31%Chromat. With hydrogen;chromium corundum; at 20 - 500.6℃; under 59631 Torr;Purification / work up; Example 9 (Hydrodealkylation) A 70 g amount of Cr2O3/Al2O3 type catalyst produced by Sud-Chemie AG is charged into a tubular reactor. The reactor is heated gradually from ambient temperature to 932 F (500 C) to dry the catalyst while supplying hydrogen gas. Thereupon distillation product (Blend-B) obtained from Example 8 is supplied to the reactor at the rate of 70 g/hr and 1.0 hr-1 in WHSV, while supplying hydrogen gas at 0.98 scf/hr (0.028 m3/hr). The hydrodealkylation reaction is carried out at 933 F (500.6 C) and 1138 psig (7.95 MPa). The product is analyzed by GC and the results of hydrodealkylation are summarized in Table 8 below.
4.75%Chromat.; 3.76%Chromat.; 0.44%Chromat.; 2.17%Chromat.; 3.53%Chromat.; 2.13%Chromat.; 0.34%Chromat.; 2.44%Chromat.; 9.48%Chromat. With hydrogen;cobalt oxide and molybdenum oxide on alumina; at 20 - 500℃; under 74482.4 Torr; Example 10 (Hydrodealkylation) A 70 g amount of CoO/MoO3/Al2O3 type catalyst produced by Akzo Chemicals Inc. is charged into a tubular reactor. The reactor is heated gradually from ambient temperature to 300F (148.9 C) with nitrogen flow at 5 scf/hr (0.142 m3/hr). Then the flow gas is switched to hydrogen at 2 scf/hr (0.057 m3/hr) and pressure is increased to 500 psig (3.55 MPa). Catalyst is contacted with an organic sulfide (Kerosene with 1.0% of Dimethyldisulfide) for sulfiding while supplying hydrogen gas and then temperature is raised to 650 F (343.3 C). Thereupon distillation product (Blend-B) obtained from Example 8 is fed to the reactor at the rate of 70 g/hr and 1.0 hr-1 in WHSV, while supplying hydrogen gas at 5scf/hr (0.028 m3/hr). Hydrodealkylation is carried out at 932 F (500 C) and 425 psig (9.93 Mpa) The product is analyzed by GC and the results of hydrodealkylation are summarized in Table 8 below. As shown in Table 8, both Cr2O3/Al2O3, and CoO/MoO3/Al2O3 type catalyst are effective to enrich DMN isomers from DMN lean feed.
Reference： [1]Patent: EP1165473,2004,B1 .Location in patent: Page 13
[2]Patent: EP1165473,2004,B1 .Location in patent: Page 13
  • 71
  • [ 581-40-8 ]
  • [ 573-98-8 ]
  • [ 571-58-4 ]
  • [ 91-20-3 ]
  • [ 582-16-1 ]
  • [ 1127-76-0 ]
  • [ 575-43-9 ]
  • [ 581-42-0 ]
  • [ 939-27-5 ]
  • [ 575-37-1 ]
  • [ 575-41-7 ]
  • [ 569-41-5 ]
  • [ 571-61-9 ]
  • [ 90-12-0 ]
  • [ 91-57-6 ]
YieldReaction ConditionsOperation in experiment
3.11%Chromat.; 4.58%Chromat.; 0.26%Chromat.; 2.92%Chromat.; 4.86%Chromat.; 0.57%Chromat.; 0.12%Chromat.; 0.39%Chromat.; 3.71%Chromat.; 15.68%Chromat. With hydrogen;chromium corundum; at 20 - 475℃; under 44929.5 Torr;Conversion of starting material; Example 4 (Hydrodealkylation) A part of Fraction-17 and Residue shown in Table 3 are mixed to prepare the feedstock(Blend-A) for hydrodealkylation. A 50 g amount of Cr2O3/Al2O3 type catalyst produced by Sud-Chemie AG is charged into a tubular reactor. The reactor is heated gradually from ambient temperature to 662F (350 C) to dry the catalyst while supplying hydrogen gas. Thereupon Blend-A is fed to the reactor at the rate of 50 g/hr and 1.0 hr-1 in WHSV, while supplying hydrogen gas at 1.25 cf/hr (0.034 m3/hr). Hydrodealkylation is carried out at 887F (475 C) and 854 psig (5.99 MPa). The product is analyzed by GC and the results of hydrodealkylation are summarized in Table 4 below. As shown in Table 4, Cr2O3/Al2O3 type catalyst is effective to enrich 2,6-DMN from 2,6-DMN lean feed.
Reference： [1]Patent: EP1165473,2004,B1 .Location in patent: Page 9-10
  • 72
  • [ 575-37-1 ]
  • [ 582-16-1 ]
YieldReaction ConditionsOperation in experiment
at 225℃;
Reference： [1]Current Patent Assignee: MITSUBISHI GAS CHEMICAL COMPANY INC - WO2006/109667, 2006, A1 Location in patent: Page/Page column 7-8
  • 73
  • [ 582-16-1 ]
  • [ 75-36-5 ]
  • [ 37558-60-4 ]
YieldReaction ConditionsOperation in experiment
45% With aluminum (III) chloride In nitromethane at 20℃; for 20h;
Reference： [1]Location in patent: experimental part Ding, Yi; Li, Yongxin; Zhang, Yi; Pullarkat, Sumod A.; Leung, Pak-Hing [European Journal of Inorganic Chemistry, 2008, # 11, p. 1880 - 1891]
  • 74
  • [ 582-16-1 ]
  • [ 75-36-5 ]
  • [ 37558-61-5 ]
YieldReaction ConditionsOperation in experiment
17.3% With aluminum (III) chloride In nitromethane at 20℃; for 20h;
Reference： [1]Location in patent: experimental part Ding, Yi; Li, Yongxin; Pullarkat, Sumod A.; See, Leng Yap; Leung, Pak-Hing [European Journal of Inorganic Chemistry, 2009, # 2, p. 267 - 276]
  • 75
  • [ 4732-69-8 ]
  • [ 582-16-1 ]
  • [ 146885-81-6 ]
  • 4,7-dimethylacenaphthylene-1,2-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
With aluminum tri-bromide In dichloromethane
Reference： [1]Guillermet, Olivier; Niemi, Eeva; Nagarajan, Samuthira; Bouju, Xavier; Martrou, David; Gourdon, Andre; Gauthier, Sebastien [Angewandte Chemie - International Edition, 2009, vol. 48, # 11, p. 1970 - 1973]
  • 76
  • [ 4732-69-8 ]
  • [ 582-16-1 ]
  • [ 121-46-0 ]
  • [ 96-22-0 ]
  • [ 1151392-63-0 ]
  • 1,6,7,10-tetramethylfluoranthene [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: Chloro-oxo-acetic acid; 2,7-dimethylnaphthalene With aluminum tri-bromide In dichloromethane Stage #2: pentan-3-one With potassium hydroxide In methanol at 20℃; for 0.75h; Stage #3: bicyclo[2.2.1]hepta-2,5-diene With acetic anhydride at 190℃; for 0.5h; Microwave irradiation;
Reference： [1]Guillermet, Olivier; Niemi, Eeva; Nagarajan, Samuthira; Bouju, Xavier; Martrou, David; Gourdon, Andre; Gauthier, Sebastien [Angewandte Chemie - International Edition, 2009, vol. 48, # 11, p. 1970 - 1973]
  • 77
  • [ 4732-69-8 ]
  • [ 582-16-1 ]
  • [ 96-22-0 ]
  • [ 1151392-62-9 ]
  • [ 146885-82-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: Chloro-oxo-acetic acid; 2,7-dimethylnaphthalene With aluminum tri-bromide In dichloromethane Stage #2: pentan-3-one With potassium hydroxide In methanol at 20℃; for 0.75h;
Reference： [1]Guillermet, Olivier; Niemi, Eeva; Nagarajan, Samuthira; Bouju, Xavier; Martrou, David; Gourdon, Andre; Gauthier, Sebastien [Angewandte Chemie - International Edition, 2009, vol. 48, # 11, p. 1970 - 1973]
  • 78
  • [ 582-16-1 ]
  • [ 2089-89-6 ]
  • [ 5159-64-8 ]
YieldReaction ConditionsOperation in experiment
With potassium permanganate In pyridine; water for 3h; Reflux; Inert atmosphere;
Reference： [1]Location in patent: scheme or table Gensini, Martina; Altamura, Maria; Dimoulas, Tula; Fedi, Valentina; Giannotti, Danilo; Giuliani, Sandro; Guidi, Antonio; Harmat, Nicholas J. S.; Meini, Stefania; Nannicini, Rossano; Pasqui, Franco; Tramontana, Manuela; Triolo, Antonio; Maggi, Carlo Alberto [ChemMedChem, 2010, vol. 5, # 1, p. 65 - 78]
  • 79
  • [ 582-16-1 ]
  • [ 124-38-9 ]
  • 2,7-dimethyl-1-naphthoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With aluminum tri-bromide; Triphenylsilyl chloride In chlorobenzene at 20℃; for 3h; Autoclave; regioselective reaction;
Reference： [1]Location in patent: experimental part Nemoto, Koji; Yoshida, Hiroki; Egusa, Naoki; Morohashi, Naoya; Hattori, Tetsutaro [Journal of Organic Chemistry, 2010, vol. 75, # 22, p. 7855 - 7862]
  • 80
  • [ 128587-73-5 ]
  • [ 582-16-1 ]
  • [ 1352227-37-2 ]
YieldReaction ConditionsOperation in experiment
1: 17.5% 2: 30.4% With sodium tetrahydroborate; potassium hydroxide In methanol; water Inert atmosphere; 6. General procedures of irradiation of 3-(4-methylstyryl)furan 1d in KOH/methanol with NaBH4 Prepared 5 same samples and each sample contained 3-(4-methylstyryl)furan 1d 20 mg, methanol 18 mL, 50% KOH(aq) 2 mL, and NaBH4 40 mg in a quartz tube (1.5 cm x 20 cm). Sealed the tubes with septa and sonicated them to dissolve the compound. Nitrogen gas bubbled for 20 minutes to remove the dissolved oxygen and then irradiated the samples with 300 nm in a local manufacturing "merry-go-round" apparatus, which contains 16 fluorescent lamps surrounding the samples. After irradiation, collected 5 samples and added 750 ml water to dilute the solution and neutralized the solution. Extracted the reaction with ethyl acetate for several times, then combined the organic layers and dried it with anhydrous MgSO4. Removed the solvent by rotary evaporator and purified product 2d by gravity chromatography with hexane/ethyl acetate = 1 : 1 as elute. After chromatography, 15.2 mg 2d and 31.6 mg 3d were gotten with the yields of 17.5% and 30.4%, respectively.
Reference： [1]Ho, Jinn-Hsuan; Lee, Tunng-Hsien; Lo, Chia-Kai; Chuang, Chao-Li [Tetrahedron Letters, 2011, vol. 52, # 52, p. 7199 - 7201]
  • 81
  • [ 128587-73-5 ]
  • [ 582-16-1 ]
YieldReaction ConditionsOperation in experiment
58% With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol; benzene for 6h; Inert atmosphere; UV-irradiation; 4. General procedures of irradiation of 3-styryfurans in DBU/benzene system General procedure: Use the irradiation of 3-(4-methylstyryl)furan 1g as an example to describe the general experimental procedures as the following: Prepared 5 same samples and each sample contained 3-(4-methylstyryl)furan 1g 20 mg, benzene 20 mL, EtOH 2 drops and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) 70 mg in a quartz tube (1.5 cm x 20 cm). Sealed the tubes with septa and sonicated them to dissolve the compound. Nitrogen gas bubbled for 20 minutes to remove the dissolved oxygen and then irradiated the samples with 300 nm in a local manufacturing "merry-go-round" apparatus, which contains 16 fluorescent lamps surrounding the samples. After irradiation, collected 5 samples and added 750 ml water to dilute the solution. Extracted the reaction with ethyl acetate for several times, then combined the organic layers and dried it with anhydrous MgSO4. Removed the solvent by rotary evaporator and purified product 2g by gravity chromatography with hexane as elute. After chromatography, 61.4 mg 2g was gotten and the yield was 58.4%.
Reference： [1]Ho, Jinn-Hsuan; Lee, Tunng-Hsien; Lo, Chia-Kai; Chuang, Chao-Li [Tetrahedron Letters, 2011, vol. 52, # 52, p. 7199 - 7201]
  • 82
  • [ 582-16-1 ]
  • [ 1333230-39-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 18 h / 80 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / Reflux 2.2: 49 h / 20 °C / Reflux
Reference： [1]Geer, Michael F.; Smith, Mark D.; Shimizu, Linda S. [CrystEngComm, 2011, vol. 13, # 11, p. 3665 - 3669]
  • 83
  • [ 582-16-1 ]
  • [ 1333230-38-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 18 h / 80 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / Reflux 2.2: 49 h / 20 °C / Reflux 3.1: diethanolamine hydrochloride / methanol; water / Reflux
Reference： [1]Geer, Michael F.; Smith, Mark D.; Shimizu, Linda S. [CrystEngComm, 2011, vol. 13, # 11, p. 3665 - 3669]
  • 84
  • [ 79-37-8 ]
  • [ 582-16-1 ]
  • [ 123-46-6 ]
  • C19H22N3O2(1+)*Cl(1-) [ No CAS ]
  • [ 146885-81-6 ]
  • 4,7-dimethylacenaphthylene-1,2-dione [ No CAS ]
Reference： [1]Organic Process Research and Development,2012,vol. 16,p. 664 - 676
  • 85
  • [ 582-16-1 ]
  • [ 5821-51-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: aluminum tri-bromide / dichloromethane / 4 h / -40 - -15 °C / Large scale reaction 1.2: 0.5 h / 40 °C / Large scale reaction 1.3: 4 h / 40 °C / Large scale reaction 2.1: potassium hydroxide / methanol / 2 h / 18 - 25 °C / Large scale reaction 3.1: acetic anhydride / 135 - 140 °C / Large scale reaction 4.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / chlorobenzene / 70 - 95 °C / 300.03 Torr / Irradiation; Large scale reaction 5.1: sodium hydroxide / water; isopropyl alcohol / 77 - 82 °C / Large scale reaction 6.1: 5%-palladium/activated carbon; formic acid; 3-Methylpyridine; triethylamine / water / 16 h / Reflux; Large scale reaction
Multi-step reaction with 6 steps 1.1: aluminum tri-bromide / dichloromethane / 4 h / -40 - -15 °C / Large scale reaction 1.2: Large scale reaction 2.1: potassium hydroxide / methanol / 2 h / 18 - 25 °C / Large scale reaction 3.1: acetic anhydride / 135 - 140 °C / Large scale reaction 4.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / chlorobenzene / 70 - 95 °C / 300.03 Torr / Irradiation; Large scale reaction 5.1: sodium hydroxide / water; isopropyl alcohol / 77 - 82 °C / Large scale reaction 6.1: 5%-palladium/activated carbon; formic acid; 3-Methylpyridine; triethylamine / water / 16 h / Reflux; Large scale reaction
Multi-step reaction with 5 steps 1.1: aluminum tri-bromide / dichloromethane / 8 h / -15 °C 1.2: 2 h / 40 °C 1.3: 2 h / 20 °C 2.1: acetic anhydride / 72 h / 140 °C 3.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 120 h / Reflux; Irradiation 4.1: sodium hydroxide / 1,4-dioxane; water / 1 h / Reflux 5.1: zinc; potassium iodide; hydrogenchloride / water; ethanol / 144 h / Reflux
Reference： [1]Butterfield, Anna M.; Gilomen, Bruno; Siegel, Jay S. [Organic Process Research and Development, 2012, vol. 16, # 4, p. 664 - 676]
[2]Butterfield, Anna M.; Gilomen, Bruno; Siegel, Jay S. [Organic Process Research and Development, 2012, vol. 16, # 4, p. 664 - 676]
[3]Rice, Allison M.; Dolgopolova, Ekaterina A.; Yarbrough, Brandon J.; Leith, Gabrielle A.; Martin, Corey R.; Stephenson, Kenneth S.; Heugh, Rebecca A.; Brandt, Amy J.; Chen, Donna A.; Karakalos, Stavros G.; Smith, Mark D.; Hatzell, Kelsey B.; Pellechia, Perry J.; Garashchuk, Sophya; Shustova, Natalia B. [Angewandte Chemie - International Edition, 2018, vol. 57, # 35, p. 11310 - 11315][Angew. Chem., 2018, vol. 130, p. 11480 - 11485,6]
  • 86
  • [ 582-16-1 ]
  • 1,6,7,10-tetramethylfluoranthene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: aluminum tri-bromide / dichloromethane / 4 h / -40 - -15 °C / Large scale reaction 1.2: 0.5 h / 40 °C / Large scale reaction 1.3: 4 h / 40 °C / Large scale reaction 2.1: potassium hydroxide / methanol / 2 h / 18 - 25 °C / Large scale reaction 3.1: acetic anhydride / 135 - 140 °C / Large scale reaction
Multi-step reaction with 3 steps 1.1: aluminum tri-bromide / dichloromethane / 4 h / -40 - -15 °C / Large scale reaction 1.2: Large scale reaction 2.1: potassium hydroxide / methanol / 2 h / 18 - 25 °C / Large scale reaction 3.1: acetic anhydride / 135 - 140 °C / Large scale reaction
Multi-step reaction with 2 steps 1.1: aluminium bromide / dichloromethane / 8 h / -15 °C 1.2: 2 h / 40 °C 1.3: 2 h / 20 °C 2.1: bicyclo[2.2.1]hepta-2,5-diene; acetic anhydride / 72 h / 140 °C
Multi-step reaction with 2 steps 1.1: aluminum tri-bromide / dichloromethane / 8 h / -15 °C 1.2: 2 h / 40 °C 1.3: 2 h / 20 °C 2.1: acetic anhydride / 72 h / 140 °C

Reference： [1]Butterfield, Anna M.; Gilomen, Bruno; Siegel, Jay S. [Organic Process Research and Development, 2012, vol. 16, # 4, p. 664 - 676]
[2]Butterfield, Anna M.; Gilomen, Bruno; Siegel, Jay S. [Organic Process Research and Development, 2012, vol. 16, # 4, p. 664 - 676]
[3]Rice, Allison M.; Fellows, W. Brett; Dolgopolova, Ekaterina A.; Greytak, Andrew B.; Vannucci, Aaron K.; Smith, Mark D.; Karakalos, Stavros G.; Krause, Jeanette A.; Avdoshenko, Stanislav M.; Popov, Alexey A.; Shustova, Natalia B. [Angewandte Chemie - International Edition, 2017, vol. 56, # 16, p. 4525 - 4529][Angew. Chem., 2017, vol. 129, # 16, p. 4596 - 4600,5]
[4]Rice, Allison M.; Dolgopolova, Ekaterina A.; Yarbrough, Brandon J.; Leith, Gabrielle A.; Martin, Corey R.; Stephenson, Kenneth S.; Heugh, Rebecca A.; Brandt, Amy J.; Chen, Donna A.; Karakalos, Stavros G.; Smith, Mark D.; Hatzell, Kelsey B.; Pellechia, Perry J.; Garashchuk, Sophya; Shustova, Natalia B. [Angewandte Chemie - International Edition, 2018, vol. 57, # 35, p. 11310 - 11315][Angew. Chem., 2018, vol. 130, p. 11480 - 11485,6]
  • 87
  • [ 582-16-1 ]
  • [ 244236-72-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: aluminum tri-bromide / dichloromethane / 4 h / -40 - -15 °C / Large scale reaction 1.2: 0.5 h / 40 °C / Large scale reaction 1.3: 4 h / 40 °C / Large scale reaction 2.1: potassium hydroxide / methanol / 2 h / 18 - 25 °C / Large scale reaction 3.1: acetic anhydride / 135 - 140 °C / Large scale reaction 4.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / chlorobenzene / 70 - 95 °C / 300.03 Torr / Irradiation; Large scale reaction
Multi-step reaction with 4 steps 1.1: aluminum tri-bromide / dichloromethane / 4 h / -40 - -15 °C / Large scale reaction 1.2: Large scale reaction 2.1: potassium hydroxide / methanol / 2 h / 18 - 25 °C / Large scale reaction 3.1: acetic anhydride / 135 - 140 °C / Large scale reaction 4.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / chlorobenzene / 70 - 95 °C / 300.03 Torr / Irradiation; Large scale reaction
Multi-step reaction with 3 steps 1.1: aluminium bromide / dichloromethane / 8 h / -15 °C 1.2: 2 h / 40 °C 1.3: 2 h / 20 °C 2.1: bicyclo[2.2.1]hepta-2,5-diene; acetic anhydride / 72 h / 140 °C 3.1: N-Bromosuccinimide; dibenzoyl peroxide / 1,1,2,2-tetrachloroethane / 120 h / Reflux; Irradiation
Multi-step reaction with 3 steps 1.1: aluminum tri-bromide / dichloromethane / 8 h / -15 °C 1.2: 2 h / 40 °C 1.3: 2 h / 20 °C 2.1: acetic anhydride / 72 h / 140 °C 3.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 120 h / Reflux; Irradiation

Reference： [1]Butterfield, Anna M.; Gilomen, Bruno; Siegel, Jay S. [Organic Process Research and Development, 2012, vol. 16, # 4, p. 664 - 676]
[2]Butterfield, Anna M.; Gilomen, Bruno; Siegel, Jay S. [Organic Process Research and Development, 2012, vol. 16, # 4, p. 664 - 676]
[3]Rice, Allison M.; Fellows, W. Brett; Dolgopolova, Ekaterina A.; Greytak, Andrew B.; Vannucci, Aaron K.; Smith, Mark D.; Karakalos, Stavros G.; Krause, Jeanette A.; Avdoshenko, Stanislav M.; Popov, Alexey A.; Shustova, Natalia B. [Angewandte Chemie - International Edition, 2017, vol. 56, # 16, p. 4525 - 4529][Angew. Chem., 2017, vol. 129, # 16, p. 4596 - 4600,5]
[4]Rice, Allison M.; Dolgopolova, Ekaterina A.; Yarbrough, Brandon J.; Leith, Gabrielle A.; Martin, Corey R.; Stephenson, Kenneth S.; Heugh, Rebecca A.; Brandt, Amy J.; Chen, Donna A.; Karakalos, Stavros G.; Smith, Mark D.; Hatzell, Kelsey B.; Pellechia, Perry J.; Garashchuk, Sophya; Shustova, Natalia B. [Angewandte Chemie - International Edition, 2018, vol. 57, # 35, p. 11310 - 11315][Angew. Chem., 2018, vol. 130, p. 11480 - 11485,6]
  • 88
  • [ 582-16-1 ]
  • [ 289721-44-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: aluminum tri-bromide / dichloromethane / 4 h / -40 - -15 °C / Large scale reaction 1.2: 0.5 h / 40 °C / Large scale reaction 1.3: 4 h / 40 °C / Large scale reaction 2.1: potassium hydroxide / methanol / 2 h / 18 - 25 °C / Large scale reaction 3.1: acetic anhydride / 135 - 140 °C / Large scale reaction 4.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / chlorobenzene / 70 - 95 °C / 300.03 Torr / Irradiation; Large scale reaction 5.1: sodium hydroxide / water; isopropyl alcohol / 77 - 82 °C / Large scale reaction
Multi-step reaction with 5 steps 1.1: aluminum tri-bromide / dichloromethane / 4 h / -40 - -15 °C / Large scale reaction 1.2: Large scale reaction 2.1: potassium hydroxide / methanol / 2 h / 18 - 25 °C / Large scale reaction 3.1: acetic anhydride / 135 - 140 °C / Large scale reaction 4.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / chlorobenzene / 70 - 95 °C / 300.03 Torr / Irradiation; Large scale reaction 5.1: sodium hydroxide / water; isopropyl alcohol / 77 - 82 °C / Large scale reaction
Multi-step reaction with 4 steps 1.1: aluminium bromide / dichloromethane / 8 h / -15 °C 1.2: 2 h / 40 °C 1.3: 2 h / 20 °C 2.1: bicyclo[2.2.1]hepta-2,5-diene; acetic anhydride / 72 h / 140 °C 3.1: N-Bromosuccinimide; dibenzoyl peroxide / 1,1,2,2-tetrachloroethane / 120 h / Reflux; Irradiation 4.1: sodium hydroxide / 1,4-dioxane; water / 1 h / Reflux
Multi-step reaction with 4 steps 1.1: aluminum tri-bromide / dichloromethane / 8 h / -15 °C 1.2: 2 h / 40 °C 1.3: 2 h / 20 °C 2.1: acetic anhydride / 72 h / 140 °C 3.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 120 h / Reflux; Irradiation 4.1: sodium hydroxide / 1,4-dioxane; water / 1 h / Reflux

Reference： [1]Butterfield, Anna M.; Gilomen, Bruno; Siegel, Jay S. [Organic Process Research and Development, 2012, vol. 16, # 4, p. 664 - 676]
[2]Butterfield, Anna M.; Gilomen, Bruno; Siegel, Jay S. [Organic Process Research and Development, 2012, vol. 16, # 4, p. 664 - 676]
[3]Rice, Allison M.; Fellows, W. Brett; Dolgopolova, Ekaterina A.; Greytak, Andrew B.; Vannucci, Aaron K.; Smith, Mark D.; Karakalos, Stavros G.; Krause, Jeanette A.; Avdoshenko, Stanislav M.; Popov, Alexey A.; Shustova, Natalia B. [Angewandte Chemie - International Edition, 2017, vol. 56, # 16, p. 4525 - 4529][Angew. Chem., 2017, vol. 129, # 16, p. 4596 - 4600,5]
[4]Rice, Allison M.; Dolgopolova, Ekaterina A.; Yarbrough, Brandon J.; Leith, Gabrielle A.; Martin, Corey R.; Stephenson, Kenneth S.; Heugh, Rebecca A.; Brandt, Amy J.; Chen, Donna A.; Karakalos, Stavros G.; Smith, Mark D.; Hatzell, Kelsey B.; Pellechia, Perry J.; Garashchuk, Sophya; Shustova, Natalia B. [Angewandte Chemie - International Edition, 2018, vol. 57, # 35, p. 11310 - 11315][Angew. Chem., 2018, vol. 130, p. 11480 - 11485,6]

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