Name: 2525-02-2|4-Propylbenzene-1,2-diol|95%
Brand: Ambeed
SKU: A553793
Price: 30.0 USD
Availability: InStock
Rating: 92 (26 reviews)

1
[ 94-58-6 ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium amide; decalin at 200℃;

Reference： [1]Helfer; Mottier [Chim. et Ind. Sonderband 14. Congr. Chim. ind. Paris 1934 Bd. 1]

2
[ 97-53-0 ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
62%	With aluminium(III) iodide In hexane at 80℃; for 18h;
	With palladium on activated charcoal Hydrogenation_.Kochen des Reaktionsprodukts mit Jodwasserstoffsaeure;

Reference： [1]Sang, Dayong; Yao, Ming; Tian, Juan; Chen, Xiaoman; Li, Li; Zhan, Hongju; You, Linhong [Synlett, 2017, vol. 28, # 1, p. 138 - 142]
[2]Spaeth; Quietinsky [Chemische Berichte, 1927, vol. 60, p. 1888]

3
[ 72769-06-3 ]
[ 64-17-5 ]
[ 2525-02-2 ]

Reference： [1]Delange [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1904, vol. 138, p. 423][Bulletin de la Societe Chimique de France, 1908, vol. <4> 3, p. 508]

4
5-propyl-benzo[1,3]dioxol-2-one [ No CAS ]
[ 64-17-5 ]
[ 2525-02-2 ]

Reference： [1]Delange [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1904, vol. 138, p. 423][Bulletin de la Societe Chimique de France, 1908, vol. <4> 3, p. 508]

5
[ 2785-87-7 ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With zeolite beta (Zeolyst, CP₈₁₄C) In water at 275℃; for 3h; Sealed tube; Inert atmosphere;	IV.55 Example 55. Variation of the temperature (275 °C) and zeolyte beta loading (CP814C) for the O-demethylation of 4-propylguaiacol [JBO-911] This experiment was performed according to a modified General procedure A. 4- Propylguaiacol (166 mg, 1 mmol) was used as the substrate, zeolite beta (Zeolyst, CP814C, Si02/Al203 = 38, H form) (100 mg) as acidic catalyst and H20 (2 mL) as the solvent. The reaction was performed at 275 °C for 3 h under 75 bar of N2 pressure. The zeolite was removed by filtration, using acetone, prior to freeze drying. 4-Propylcatechol was isolated in 99% yield. General procedure A (0233) A 4 mL glass vial was charged with a magnetic stirring bar, the substrate for the experiment, the acid or alkaline reagent and 2 mL of the appropriate solvent or solvent mixture. The vial was closed properly with the correct cap and septum and the septum was pierced with a syringe needle. This vial was brought to the 4620 Parr reactor and the reactor was closed properly. The reactor was flushed with the appropriate gas (3 x 10 bar) and then filled with this gas (with the reported pressure). The reactor was heated to the reaction temperature and this temperature was maintained for the reported reaction time (it takes approx. 60 min to reach 250 °C). After cooling down (from 250 °C to 170 °C in the air and from 170 °C to r.t. in an ice bath), the gas was released and the reactor was opened. (0234) After opening the reactor, the crude reaction mixture was brought to a roundbottomed flask and the vial was rinsed with H20 (3 mL). This aqueous reaction mixture was freezed by gently rotating the flask in liq. N2. Subsequently, vacuum was applied until all volatiles were removed. If necessary, this freeze drying step was repeated multiple times. The residue was redissolved in acetone, filtered over a silica plug and the filtrate was concentrated under reduced pressure by using a rotary evaporator. The residue was analysed with NMR and MS (APCI) or LC-MS.
97%	With hydrogen bromide In water at 115℃;
97%	With hydrogenchloride; water at 250℃; for 3h; Sealed tube; Inert atmosphere;

97%	With hydrogenchloride In water at 250℃; for 3h; Autoclave; Inert atmosphere; Green chemistry;
96%	With aluminium(III) iodide In dimethyl sulfoxide; acetonitrile at 80℃; for 18h;	15 Example 15 (4-methyl-2-methoxyphenol demethylation) Add aluminum triiodide (2·240 g, 5 · 5 mmol), acetonitrile (40 ml) and DMSO (0.430 g, 5.5 mmol) to a 100 ml eggplant-shaped flask, and heat to 80 ° C with stirring, and stir for 0.5 hour. Then, 4-propyl-2-methoxyphenol (0.831 g, 5.0 mmol) was added, and the reaction was further stirred (80 ° C), the reaction was stopped after 18 hours, and after cooling to room temperature, 2 mol was added to the eggplant-shaped flask. /L of dilute hydrochloric acid (10 ml), EtOAc (EtOAc (EtOAc) (EtOAc) Dry over magnesium sulfate, filter, and the filtrate was evaporated to dryness with a rotary evaporator, and the residue was purified by flash column chromatography (ethyl acetate / petroleum ether = 1:4, volume ratio) to give 0.736 g of 4-propyl Hydroquinone (white solid, yield 96%).
96%	With aluminium(III) iodide; dimethyl sulfoxide In acetonitrile at 80℃; for 18h;	Cleavage of Catechol Monoalkyl Ethers by Aluminum Triiodide- Dimethyl Sulfoxide; General Procedure General procedure: To a suspension of AlI3 (5.5 mmol, 1.1 equiv) in MeCN was added anhyd DMSO (0.430 g, 5.5 mmol, 1.1 equiv). After stirring for 0.5 h at 80 °C, the selected substrate (5 mmol) was added in one portion. The mixture was stirred overnight (18 h) at that temperature before quenching with aq 2 M HCl (10 mL). After extraction with EtOAc (3 50 mL), the organic phases were combined, washed with sat. aq Na2S2O3 and brine, and dried (MgSO4). The solvents were removed on a rotary evaporator, and the residue was purified by column chromatography to give the relevant catechol or phenol.
90%	With aluminium(III) iodide; <i>N</i>,<i>N</i>-dimethyl-formamide dimethyl acetal In acetonitrile at 80℃; for 18h;
90%	With aluminium(III) iodide; <i>N</i>,<i>N</i>-dimethyl-formamide dimethyl acetal In acetonitrile at 80℃; for 18h;	17 Example 17 (4-propyl-2-methoxyphenol demethylation) Add acetonitrile (40ml), aluminum triiodide (2.242g, 5.5mmol) and N,N-dimethylformamide dimethyl acetal (0.894g, 7.5mmol) to a 100ml round-bottomed flask at 80°C Stir for 15min, add 4-propyl-2-methoxyphenol (0.831g, 5mmol), continue stirring at 80°C for 18h, after the reaction is complete, quench with 2M dilute hydrochloric acid (10ml), and then use ethyl acetate (50ml ) Extract three times, combine the organic phases, wash with saturated sodium thiosulfate aqueous solution (10ml), then dry with anhydrous magnesium sulfate, filter, and remove the solvent from the filtrate with a rotary evaporator. The residue is passed through flash column chromatography (eluent It was purified with petroleum ether/ethyl acetate=4:1, volume ratio) to obtain 0.690 g of 4-propylcatechol (light yellow liquid, yield 90%).
89%	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In tetrahydrofuran at 20℃; for 12h;
	With hydrogen bromide at 100℃;
	With hydrogenchloride at 140℃;
	With pyridine; phosphorus tribromide

Reference： [1]Current Patent Assignee: UNIVERSITY OF ANTWERP - WO2019/25535, 2019, A1 Location in patent: Page/Page column 23; 37
[2]Dobi, Zoltán; Reddy, B. Narendraprasad; Renders, Evelien; Van Raemdonck, Laurent; Mensch, Carl; De Smet, Gilles; Chen, Chen; Bheeter, Charles; Sergeyev, Sergey; Herrebout, Wouter A.; Maes, Bert U. W. [ChemSusChem, 2019, vol. 12, # 13, p. 3103 - 3114]
[3]Bal, Mathias; Bomon, Jeroen; Liao, Yuhe; Maes, Bert U. W.; Sels, Bert F.; Sergeyev, Sergey; Van Den Broeck, Elias; Van Speybroeck, Veronique [Angewandte Chemie - International Edition, 2020, vol. 59, # 8, p. 3063 - 3068][Angew. Chem., 2020, vol. 132, p. 3087 - 3092,6]
[4]Bomon, Jeroen; Bal, Mathias; Achar, Tapas Kumar; Sergeyev, Sergey; Wu, Xian; Wambacq, Ben; Lemière, Filip; Sels, Bert F.; Maes, Bert U. W. [Green Chemistry, 2021, vol. 23, # 5, p. 1995 - 2009]
[5]Current Patent Assignee: JINGCHU UNIVERSITY OF TECHNOLOGY - CN108821930, 2018, A Location in patent: Paragraph 0084-0089
[6]Sang, Dayong; Tian, Juan; Tu, Xiaodong; He, Zhoujun; Yao, Ming [Synthesis, 2019, vol. 51, # 3, p. 704 - 712]
[7]Sang, Dayong; Yue, Huaxin; Zhao, Zhengdong; Yang, Pengtao; Tian, Juan [Journal of Organic Chemistry, 2020, vol. 85, # 10, p. 6429 - 6440]
[8]Current Patent Assignee: JINGCHU UNIVERSITY OF TECHNOLOGY - CN111620764, 2020, A Location in patent: Paragraph 0119-0123
[9]Ozanne, Aurelie; Pouysegu, Laurent; Depernet, Dominique; Francois, Bruno; Quideau, Stephane [Organic Letters, 2003, vol. 5, # 16, p. 2903 - 2906]
[10]Gauthier [Annales de Chimie (Cachan, France), 1945, vol. <11> 20, p. 581,608][Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1943, vol. 217, p. 28]
[11]Pastrovich [Monatshefte fur Chemie, 1883, vol. 4, p. 190]
[12]Gauthier [Annales de Chimie (Cachan, France), 1945, vol. <11> 20, p. 581,608][Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1943, vol. 217, p. 28]

6
[ 2525-02-2 ]
[ 101279-81-6 ]

Yield	Reaction Conditions	Operation in experiment
	With diethyl ether; silver(l) oxide anschliessend Behandeln mit 3-Methoxy-<i>o</i>-phenylendiamin;

Reference： [1]Kiprianow; Krotschtschenko [Ukrainskij Khimicheskij Zhurnal, 1956, vol. 22, p. 351,354][Chem.Abstr., 1957, p. 2807]

7
[ 7451-98-1 ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; amalgamated zinc
	With palladium on activated charcoal; ethanol Hydrogenation;

Reference： [1]Current Patent Assignee: MERCK & CO INC - US2298291, 1935, A
[2]Hartung; Crossley [Journal of the American Chemical Society, 1934, vol. 56, p. 158] Current Patent Assignee: MERCK & CO INC - US2298291, 1935, A

8
[ 2525-02-2 ]
[ 106-89-8 ]
(6-Propyl-2,3-dihydro-benzo[1,4]dioxin-2-yl)-methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide

Reference： [1]Current Patent Assignee: Geigy A.G. - US2366611, 1943, A

9
[ 120-58-1 ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; sodium man behandelt das Dihydroderivat mit PCl₅ und kocht das enstehende Chlorprodukt mit Wasser;

Reference： [1]Delange [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1900, vol. 130, p. 660]

10
[ 93-16-3 ]
[ 2525-02-2 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1900,vol. 130,p. 660

11
[ 2525-02-2 ]
[ 99-33-2 ]
1,2-bis-(3,5-dinitro-benzoyloxy)-4-propyl-benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine

Reference： [1]Freudenberg; Adam [Chemische Berichte, 1941, vol. 74, p. 387,394]

12
[ 94-58-6 ]
[ 2525-02-2 ]
[ 34827-26-4 ]

Yield	Reaction Conditions	Operation in experiment
	With boron trifluoride diethyl etherate

Reference： [1]Tomar, S. S.; Walia, Suresh; Mukerjee, S. K. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 9, p. 792 - 793]

13
[ 46287-79-0 ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
	(i) H₂, Pd-C, EtOH, (ii) aq. H₂SO₄, MeOH; Multistep reaction;

Reference： [1]Zbiral,E. et al. [Monatshefte fur Chemie, 1961, vol. 92, p. 654 - 666]

14
[ 1126-61-0 ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 1h; Inert atmosphere;	Preparation of 4-Propylcatechol (8) from 1 To a solution of allylpyrocatechol (1, 6.7 mg, 0.044 mmol) in MeOH (0.3 mL) was added 10% palladium on carbon (Pd-C) (2.0 mg) at room temperature. After stirring for 1 h at room temperature under H2 atmosphere, the reaction mixture was filtered through Celite. The filtrate was concentrated under reduced pressure to afford the crude product, which was purified by silica gel column chromatography (EtOAc only) to give 8 (6.8 mg, quant.). The obtained products was identified by the previously reported spectroscopic data.12)
95%	With hydrogen In methanol at 20℃; for 2h;	4.1 To a solution of Compound No. 1 (5 g, 0.033 mol) as obtained in Example 3, in dry methanol (30 mL) was added 10 % Pd-charcoal (750 mg, 1.5 eq.). The reaction mixture was stirred at room temperature for 2 hours. After complete disappearance of the starting material, the reaction mixture was filtered over a bed of Celite using methanol.The filtrate was concentrated and purified by column chromatography (silica gel: 60-120 mesh) using petroleum ether with increasing proportion of chloroform. The eluant of 60 % chloroform in petroleum ether, on concentration, gave the desired compoundC.Yield : 4.8 g (95 %); Colourless liquid1H NMR (300MHz, CDCl3): δ 0.98 (t, J= 7.31 Hz, 3H), 1.58 - 1.72 (m, 2H), 2.58 (t,J= 7.64 Hz, 2H), 5.05 (brs, 2H), 6.60 (d, J= 6.62 Hz, IH), 6.67 (d, J= 6.69 Hz, IH), 6.75 (s, IH).GCMS m/z : 152 [M+, 100%]
95%	With methanol; palladium 10% on activated carbon at 20℃; for 2h;	4.1 Step 1) Preparation of Compound C Step 1) Preparation of Compound C: Compound C: 4-propylbenzene-1,2-diol [0191] To a solution of Compound No. 1 (5 g, 0.033 mol) as obtained in Example 3, in dry methanol (30 mL) was added 10% Pd-charcoal (750 mg, 1.5 eq.). The reaction mixture was stirred at room temperature for 2 hours. After complete disappearance of the starting material, the reaction mixture was filtered over a bed of Celite using methanol. The filtrate was concentrated and purified by column chromatography (silica gel: 60-120 mesh) using petroleum ether with increasing proportion of chloroform. The eluant of 60% chloroform in petroleum ether, on concentration, gave the desired compound C. [0192] Yield: 4.8 g (95%); Colourless liquid [0193] 1H NMR (300 MHz, CDCl3): δ 0.98 (t, J=7.31 Hz, 3H), 1.58-1.72 (m, 2H), 2.58 (t, J=7.64 Hz, 2H), 5.05 (brs, 2H), 6.60 (d, J=6.62 Hz, 1H), 6.67 (d, J=6.69 Hz, 1H), 6.75 (s, 1H). [0194] GCMS m/z: 152 [M+, 100%]

	With triphenyl phosphite; hydrogen In chloroform at 25℃;
	With hydrogen In ethanol; trifluoroacetic acid for 24h;

Reference： [1]Horii, Toshihiro; Itagaki, Sawako; Kawano, Tomikazu; Miyoshi, Akihito; Murakami, Nobutoshi; Tamura, Satoru [Chemical and Pharmaceutical Bulletin, 2020, vol. 68, # 8, p. 784 - 790]
[2]Current Patent Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (IN) - WO2010/79423, 2010, A1 Location in patent: Page/Page column 21
[3]Current Patent Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (IN) - US2014/135393, 2014, A1 Location in patent: Paragraph 0190-0194
[4]Coolen, Hein K. A. C.; Meeuwis, Johannes A. M.; Van Leeuwen, Piet W. N. M.; Nolte, Roeland J. M. [Journal of the American Chemical Society, 1995, vol. 117, # 48, p. 11906 - 11913]
[5]Iverson; Li Qing Hu; Vukomanovic; Bolton [Chemical Research in Toxicology, 1995, vol. 8, # 4, p. 537 - 544]

15
[ 2525-02-2 ]
4-propyl-3,5-cyclohexadiene-1,2-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With silver(l) oxide In acetonitrile at 60℃; for 0.5h;
	With Agaricus bisporus tyrosinase aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Bolton; Hao Ming Wu; Li Qing Hu [Chemical Research in Toxicology, 1996, vol. 9, # 1, p. 109 - 113]
[2]Location in patent: experimental part Ramsden, Christopher A.; Riley, Patrick A. [ARKIVOC, 2010, vol. 2010, # 10, p. 248 - 254]

16
[ 70-18-8 ]
[ 2525-02-2 ]
(S)-2-Amino-4-[(R)-1-(carboxymethyl-carbamoyl)-2-(2,3-dihydroxy-5-propyl-phenylsulfanyl)-ethylcarbamoyl]-butyric acid [ No CAS ]
(S)-2-Amino-4-[(R)-1-(carboxymethyl-carbamoyl)-2-(4,5-dihydroxy-2-propyl-phenylsulfanyl)-ethylcarbamoyl]-butyric acid [ No CAS ]
(S)-2-Amino-4-[(R)-1-(carboxymethyl-carbamoyl)-2-(2,3-dihydroxy-6-propyl-phenylsulfanyl)-ethylcarbamoyl]-butyric acid [ No CAS ]
(S)-2-Amino-4-[(R)-2-{2-[(R)-2-((S)-4-amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-3,4-dihydroxy-6-propyl-phenylsulfanyl}-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tyrosinase In water at 25℃; for 1h;

Reference： [1]Iverson; Li Qing Hu; Vukomanovic; Bolton [Chemical Research in Toxicology, 1995, vol. 8, # 4, p. 537 - 544]

17
[ 72769-06-3 ]
[ 7732-18-5 ]
[ 2525-02-2 ]

Reference： [1]Delange [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1904, vol. 138, p. 423][Bulletin de la Societe Chimique de France, 1908, vol. <4> 3, p. 508]

18
5-propyl-benzo[1,3]dioxol-2-one [ No CAS ]
[ 7732-18-5 ]
[ 2525-02-2 ]

Reference： [1]Delange [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1904, vol. 138, p. 423][Bulletin de la Societe Chimique de France, 1908, vol. <4> 3, p. 508]

19
[ 7647-01-0 ]
[ 94-58-6 ]
[ 108-46-3 ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
	at 125℃; im Rohr;

Reference： [1]Spaeth; Quietensky [Chemische Berichte, 1927, vol. 60, p. 1887]

20
[ 120-58-1 ]
[ 94-58-6 ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
	at 200℃; isosafrole-substances of uncertain configurative homogeneity;

Reference： [1]Kimura [Bulletin of the Chemical Society of Japan, 1935, vol. 10, p. 330,333]

21
[ 94-59-7 ]
[ 106-44-5 ]
[ 94-58-6 ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
	at 190℃;

Reference： [1]Kimura [Bulletin of the Chemical Society of Japan, 1935, vol. 10, p. 330,333]

22
2,2-diphenoxy-5-propyl-benzo[1,3]dioxole [ No CAS ]
[ 2525-02-2 ]
methylammonium carbonate [ No CAS ]
[ 108-95-2 ]

Reference： [1]Delange [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1904, vol. 138, p. 423][Bulletin de la Societe Chimique de France, 1908, vol. <4> 3, p. 508]

Yield	Reaction Conditions	Operation in experiment
	Rk. m. FeCl3 in A. -> gruen;

Yield	Reaction Conditions	Operation in experiment
	Dihydroeugenol, HBr, HI;
		The preferred substituted catechols according to the invention are substituted at the 3 or the 4 position and examples of these are: 3-methylcatechol 4-methylcatechol 4-n-propylcatechol 3-isopropylcatechol 4-isopropylcatechol 3-methoxycatechol 4-t-butylcatechol 4-aminocatechol 4(N-methyl)aminocatechol
		Further examples of substituted catechols are: ... 1,2-dihydroxy-4-sec.butoxybenzene 1,2-dihydroxy-4-tert.butoxybenzene 1,2-dihydroxy-4-methylbenzene 1,2-dihydroxy-4-ethylbenzene 1,2-dihydroxy-4-propylbenzene 1,2-dihydroxy-4-isopropylbenzene 1,2-dihydroxy-4-butylbenzene 1,2-dihydroxy-4-isobutylbenzene ...

Yield	Reaction Conditions	Operation in experiment
	With water
	With ethanol

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; recorcinol at 125℃; im Rohr;
	With methyl magnesium iodide at 130℃; Kochen des Reaktionsprodukts mit Jodwasserstoffsaeure;

Yield	Reaction Conditions	Operation in experiment
	With copper oxide-chromium oxide; hydrogen at 325℃; sowie bei 400grad;
	With tin iodide-catalyst; hydrogen at 325℃; sowie bei 400grad;

28
[ 64-17-5 ]
[ 7451-98-1 ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
	Raumtemperatur_.Hydrogenation;

Reference： [1]Hartung; Crossley [Journal of the American Chemical Society, 1934, vol. 56, p. 158]

30
[ 70-18-8 ]
[ 2525-02-2 ]
(S)-2-Amino-4-{(R)-1-(carboxymethyl-carbamoyl)-2-[(S)-1-(3,4-dihydroxy-phenyl)-propylsulfanyl]-ethylcarbamoyl}-butyric acid [ No CAS ]
(S)-2-Amino-4-{(R)-1-(carboxymethyl-carbamoyl)-2-[(R)-1-(3,4-dihydroxy-phenyl)-propylsulfanyl]-ethylcarbamoyl}-butyric acid [ No CAS ]
(S)-2-Amino-4-[(R)-1-(carboxymethyl-carbamoyl)-2-(4,5-dihydroxy-2-propyl-phenylsulfanyl)-ethylcarbamoyl]-butyric acid [ No CAS ]
(S)-2-Amino-4-[(R)-2-{2-[(R)-2-((S)-4-amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-3,4-dihydroxy-6-propyl-phenylsulfanyl}-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-propylbenzene-1,2-diol With silver(l) oxide In acetonitrile at 60℃; for 0.5h; Stage #2: GLUTATHIONE In water; acetonitrile Further byproducts given;

Reference： [1]Iverson; Li Qing Hu; Vukomanovic; Bolton [Chemical Research in Toxicology, 1995, vol. 8, # 4, p. 537 - 544]

31
tetraethyl (E)-N-[3-(3,4-dibenzyloxyphenylprop-2-enylidene)amino]methylbisphosphonate [ No CAS ]
[ 2525-02-2 ]
[ 740083-66-3 ]

Yield	Reaction Conditions	Operation in experiment
78.8%	With hydrogen In ethyl acetate at 20℃; for 4h; atmospheric pressure;

Reference： [1]Xu, Guangyu; Yang, Chunhao; Liu, Bo; Wu, Xihan; Xie, Yuyuan [Heteroatom Chemistry, 2004, vol. 15, # 3, p. 251 - 257]

32
[ 2525-02-2 ]
[ 534-07-6 ]
7-propyl-2H-1,5-benzodioxepin-3(4H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58.4%
55%	With potassium carbonate; sodium iodide In acetone for 4h; Heating;

Reference： [1]Current Patent Assignee: TAKASAGO INTERNATIONAL CORPORATION - EP1405851, 2004, A1 Location in patent: Page 16-17
[2]Gaudin, Jean-Marc; Nikolaenko, Olga; De Saint Laumer, Jean-Yves; Winter, Beat; Blanc, Pierre-Alain [Helvetica Chimica Acta, 2007, vol. 90, # 7, p. 1245 - 1265]

33
(E)-3,4-bis(benzyloxy)cinnamaldehyde [ No CAS ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 71.7 percent / benzene / 4 h / Heating 2: H₂ / Pd/C / ethyl acetate / 4 h / 20 °C / atmospheric pressure

Reference： [1]Xu, Guangyu; Yang, Chunhao; Liu, Bo; Wu, Xihan; Xie, Yuyuan [Heteroatom Chemistry, 2004, vol. 15, # 3, p. 251 - 257]

34
[ 2525-02-2 ]
[ 108013-46-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Ag₂O; diethyl ether / anschliessend Behandeln mit 3-Methoxy-<i>o</i>-phenylendiamin 2: AlCl₃; benzene

Reference： [1]Kiprianow; Krotschtschenko [Ukrainskij Khimicheskij Zhurnal, 1956, vol. 22, p. 351,354][Chem.Abstr., 1957, p. 2807]

35
[ 2525-02-2 ]
[ 109251-73-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Ag₂O; diethyl ether / anschliessend Behandeln mit 3-Methoxy-<i>o</i>-phenylendiamin 2: AlCl₃; benzene 3: anschliessend Behandeln mit wss. NaOH

Reference： [1]Kiprianow; Krotschtschenko [Ukrainskij Khimicheskij Zhurnal, 1956, vol. 22, p. 351,354][Chem.Abstr., 1957, p. 2807]

36
[ 2525-02-2 ]
7-propyl-2H-1,5-benzodioxepin-3(4H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		1 Preparation of 7-propyl-2H,4H-1,5-benzodioxepin-3-one EXAMPLE 1 Preparation of 7-propyl-2H,4H-1,5-benzodioxepin-3-one This compound was prepared using known reactions, starting from 97% pure 4-propyl-1,2- benzenediol. This starting product, having an odor of the copper, phenolic, slightly fatty type, was converted in an analogous way to that described in U.S. Pat. No. 3,799,892 to give a crude product which, after purification and crystallization in heptane at -20° C., gave 7-propyl-2H,4H-1,5-benzodioxepin-3-one with a purity above 99%, showing the following spectral data: NMR(13 C): 13.75(q); 24.42(t); 37.09(t); 75.49(t); 75.77(t); 120.53(d); 120.60(d); 123.71(d); 138.71(s); 146.22(s); 147.98(s); 204.85(s) δ ppm NMR(1 H): 0.93(t, J=8, 3H); 1.60(m, 2H); 2.50(t, J=6, 2H); 4.66(s, 2H); 4.70(s, 2H); 6.76(dd, J=2, J=8, 1H); 6.80(d, J=2, 1H); 6.90(d, J=8, 1H) δ ppm MS: 206(M+): 177(100), 149(30), 135(10), 123(8), 105(5), 91(10), 77(18), 65(10), 55(8), 51(10), 39(10).

Reference： [1]Current Patent Assignee: Firmenich International SA - US5990076, 1999, A

37
[ 56-23-5 ]
petroleum benzine [ No CAS ]
[ 79-37-8 ]
[ 2525-02-2 ]
6-n-propyl-1,4-benzodioxine-2,3-dione monohydrate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine	7 Preparation of 6-n-propyl-1,4-benzodioxine2,3-dione EXAMPLE 7 Preparation of 6-n-propyl-1,4-benzodioxine2,3-dione A mixture of 3.81 g (25 mM) of 4-n-propylcatechol, 5.06 g (50 mM) of triethylamine and 50 ml of dry ether was cooled in an ice water bath so as to maintain the temperature at 5° C. or below. The mixture was added dropwise over 1.5 hours under stirring with a solution of 3.50 g (28 mM) of oxalyl chloride in 10 ml of dry ether. After completing the dropwise addition, the temperature of the reaction mixture was gradually raised to the room temperature and then aging was conducted for an hour. The resultant mixture was heated under reflux for 3 hours in order to complete the aging. The separated crystals of triethyl ammonium chloride was filtered. After thoroughly washing the crystals with ether, the ether solution was collected and dried with anhydrous sodium sulfate. After distilling off ether, the reaction product was recrystallized from a solvent mixture of carbontetrachloride and petroleum benzine to obtain 4.64 g (22.5 mM) of 6-n-propyl-1,4-benzodioxine-2,3-dione monohydrate as colorless crystals having a melting point of 99°-100° C.

Reference： [1]Current Patent Assignee: MITSUI CHEMICALS,INC. - US4985458, 1991, A

38
[ 5888-52-8 ]
sodium thiosulfate [ No CAS ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen bromide; acetic acid In water	3.2 (2) (2) Preparation of 4-propylcatechol A mixture of 15.0 g (83 mM) of 4-propylveratrole, 53.0 g (882 mM) of acetic acid and 159.4 g (926 mM of 47% hydrobromic acid was heated under reflux for 2 hours with stirring. After cooling to the room temperature, the reaction mixture was added with 140 ml of water and extracted three times with each 150 ml of ether. The extracted ether solution was successively washed with 150 ml of water, 150 g of 5% aqueous sodium thiosulfate solution and then twice with each 150 ml of water. The resulting solution was dried with anhydrous sodium sulfate, distilled off ether and vacuum distilled to obtain 10.5 g (69 mM) of 4-propylcatechol as a light yellow liquid having a boiling-point of 119° C./3 mmHg.

Reference： [1]Current Patent Assignee: MITSUI CHEMICALS,INC. - US4985458, 1991, A

39
[ 2525-02-2 ]
4-propyl-1,2-phenyl diacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic anhydride	3.3 (3) (3) Preparation of 1,2-diacetoxy-4-propylbenzene A mixture of 2.7 g (18 mM) of 4-propylcatechol and 4.1 g (40 mM) of acetic anhydride was added with a drop of concentrated sulfuric acid. An exothermic reaction was immediately initiated. After cooling to the room temperature the reaction mixture was poured into ice water. The separated oil was extracted with ether, dried with anhydrous sodium sulfate, and distilled off ether. The residue was vacuum distilled to obtain 4.2 g (17 mM) of 1,2-diacetoxy-4-propylbenzene as colorless transparent liquid having a boiling point of 111°-119° C./ 4 mmHg.

Reference： [1]Current Patent Assignee: MITSUI CHEMICALS,INC. - US4985458, 1991, A

40
[ 2525-02-2 ]
n-Propyl-2,2-dimethyl-1,3-benzodioxol [ No CAS ]
[ 115328-34-2 ]

Yield	Reaction Conditions	Operation in experiment
	With p-toluenesulfonic acid monohydrate In acetone; benzene	12 Preparation of 5-n-propyl-2,2-dimethyl-1,3benzodioxol EXAMPLE 12 Preparation of 5-n-propyl-2,2-dimethyl-1,3benzodioxol The same procedures as described in Example 10 were carried out by using a mixture of 7.61 g (50 mM) of 4-n-propylcatechol, 15 ml of acetone, 30 mg of p-toluenesulfonic acid monohydrate and 15 ml of benzene. 5 n-Propyl-2,2-dimethyl-1,3-benzodioxol was obtained in the yield of 9.13 g (47 mM) as colorless transparent liquid having a boiling point of 82°-87° C./3 mmHg. In addition, 4-n-propylcatechol employed as the starting material was prepared by the following process.

Reference： [1]Current Patent Assignee: MITSUI CHEMICALS,INC. - US4985458, 1991, A

41
[ 1990-24-5 ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide; sodium hydrogencarbonate; In methanol; water;	Example 1D Synthesis of 4-propyl catechol A sodium bicarbonate solution (4.2 g; 50 mmols) in water (25 ml) was added with <strong>[1990-24-5]2-acetyl-4-propyl phenol</strong> (8.6 g; 50 mmols) dissolved in methanol (25 ml). The resulting mixture, maintained at room temperature, was slowly added with 15% hydrogen peroxide (11.9 g; 52.5 mmols) (%, w/w). Once the addition had been completed, the mixture was allowed to stir for 4 hrs and evaporated in vacuo (45C / 24 mbar). The aqueous residue was taken up with water (30 ml) and extracted three times with isopropyl ether (50 ml). The organic phase was evaporated in vacuo (30C / 24 mbar) to give a very thick yellow oil.
	With dihydrogen peroxide; sodium hydrogencarbonate; In methanol; water;	EXAMPLE 1D Synthesis of 4-propyl Catechol A sodium bicarbonate solution (4.2 g; 50 mmols) in water (25 ml) was added with <strong>[1990-24-5]2-acetyl-4-propyl phenol</strong> (8.6 g; 50 mmols) dissolved in methanol (25 ml). The resulting mixture, maintained at room temperature, was slowly added with 15% hydrogen peroxide (11.9 g; 52.5 mmols) (%, w/w). Once the addition had been completed, the mixture was allowed to stir for 4 hrs and evaporated in vacuo (45 C./24 mbar). The aqueous residue was taken up with water (30 ml) and extracted three times with isopropyl ether (50 ml). The organic phase was evaporated in vacuo (30 C./24 mbar) to give a very thick yellow oil.

Reference： [1]Patent: EP1048664,2000,A2
[2]Patent: US6252092,2001,B1

42
K₂CO₃(141 g; 87 mmols) [ No CAS ]
[ 2525-02-2 ]
[ 94-58-6 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; N,N-dimethyl-formamide	1.E Example 1E Example 1E : Synthesis of 5-propyl benzodioxole 4-Propyl catechol (10.7 g; 70 mmols) was dissolved in a 90:10 (v/v) DMF/dichloromethane mixture (17 ml). The resulting solution was added very slowly to a suspension of anhydrous K2CO3(14.1 g; 87 mmols) in a 90:10 (v/v) DMF/dichloromethane mixture (85 ml), maintained at 115-120°C. Once the addition had been completed, the solution was kept at 120-125°C for additional 3 hrs, cooled and filtered. The mixture was filtered at 60°C / 12 mbar and the residue was taken up with water (30 ml) and extracted with n-hexane (50 ml). The organic phase was dried over anhydrous sodium sulphate, filtered and dried in vacuo (30°C / 24 mbar). 11.2 g of 5-propyl benzo-[1.3]-dioxole was obtained.

Reference： [1]Current Patent Assignee: ENDURA SPA - EP1048664, 2000, A2

43
[ 2525-02-2 ]
[ 94-58-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In dichloromethane; N,N-dimethyl-formamide	1.E Synthesis of 5-propyl Benzodioxole EXAMPLE 1E Synthesis of 5-propyl Benzodioxole 4-Propyl catechol (10.7 g; 70 mmols) was dissolved in a 90:10 (v/v) DMF/dichloromethane mixture (17 ml). The resulting solution was added very slowly to a suspension of anhydrous K2CO3 (14.1 g; 87 mmols) in a 90:10 (v/v) DMF/dichloromethane mixture (85 ml), maintained at 115-120° C. Once the addition had been completed, the solution was kept at 120-125° C. for additional 3 hrs, cooled and filtered. The mixture was filtered at 60° C./12 mbar and the residue was taken up with water (30 ml) and extracted with n-hexane (50 ml). The organic phase was dried over anhydrous sodium sulphate, filtered and dried in vacuo (30° C./24 mbar). 11.2 g of 5-propyl benzo-[1,3]-dioxole was obtained.

Reference： [1]Current Patent Assignee: ENDURA SPA - US6252092, 2001, B1

44
[ 2525-02-2 ]
[ 106-95-6 ]
[ 1234378-77-8 ]
[ 1234378-87-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 15% 2: 20.58%	Stage #1: 4-propylbenzene-1,2-diol With potassium carbonate In acetone for 1.5h; Stage #2: allyl bromide In acetone for 5.5h; Reflux; Stage #3: at 175 - 180℃; for 2h; Neat (no solvent);	4.2 Compound C (1 g, 0.0066 mol) and dry acetone (15 mL) were stirred for 30 minutes and then dry K2CO3 (0.832 g, 0.0059 mol) was added in portions for 30 minutes The stirring was continued for another hour. Allyl bromide (0.499 mL, 0.0058 mol) was then added to the mixture for 30 minutes. The reaction mixture was refluxed for 5 hours. After completion of the reaction, the reaction mixture was filtered. The filtrate was concentrated and extracted with chloroform (3 x 50 mL), washed with brine (1 x 50 mL) and dried over anhydrous sodium sulfate. The solvent was then removed under reduced pressure. The crude material was heated at 175-180 0C for 2 hours. After complete disappearance of the starting material, the reaction mixture was purified by column chromatography (silica gel: 60-120 mesh) using petroleum ether with increasing concentration of chloroform. The pure compounds corresponding to Compound No. 17 and Compound No. 4 were eluted at 25 % and 45 % chloroform in petroleum ether respectively.Compound 4Yield : 200 mg (15 %); colourless liquid1H NMR (300MHz, CDCl3,): δ 0.97 (t, J= 7.24 Hz, 3H), 1.57 - 1.67 (m, 2H),2.54 (t, J= 7.82 Hz, 2H), 3.39 (d, J=6.18 Hz, 2H), 4.9-5.39 (m, 4H), 5.9-6.07 (m, IH), 6.60 (s, IH), 6.65 (s, Hz, IH).Mass (ESI) m/z : 191[M-HVCompound 17Yield : 260 mg (20.58 %); light yellow liquid.1H NMR (300MHz, CDCl3): δ 0.97 (t, J= 7.22 Hz, 3H), 1.59 - 1.67 (m, 2H),2.57 (t, J= 7.54 Hz, 2H), 3.31 (d, J=5.94 Hz, 2H), 5.01 (d, J= 8.0, 2H), 5.35 (s, IH), 5.59 (s, IH), 5.88-5.9 (m, IH), 6.59 (d, J= 7.54 Hz, IH), 6.66 (d, J= 7.54 Hz, IH).Mass (ESI) m/z : 191 [M-H]"

Reference： [1]Current Patent Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (IN) - WO2010/79423, 2010, A1 Location in patent: Page/Page column 21-22

45
lignin acetosolv type [ No CAS ]
[ 645-56-7 ]
[ 93-51-6 ]
[ 2785-87-7 ]
[ 97-54-1 ]
[ 2785-89-9 ]
[ 2380-78-1 ]
[ 2525-02-2 ]
[ 120-80-9 ]
[ 90-05-1 ]
[ 452-86-8 ]

Yield	Reaction Conditions	Operation in experiment
	With 5% palladium on Al2O3; hydrogen; In water; at 25 - 310℃; under 37503.8 Torr; for 1h;Autoclave;	The lignin used in Examples 4 to 13 is of the Acetosolv type for Examples 4, 5 and 6 (comparative) and for Examples 9, 10, 11 and 13 (invention), of the Organosolv type for Examples 7 and 8 (invention) and of the Kraft type for Example 12 (invention). [0154] The lignin of the Acetosolv type was obtained from a mixture of fir/pine wood, operating as described in the article of X. Pan et al. ?Acetic acid pulping of wheat straw under atmospheric pressure?, published in ?Journal of Wood Science? (1999), Vol. 45 (4), pages 319-325. The lignins of the Organosolv and Kraft types used are commercial products from the Aldrich catalogue cod. 371017 (batch 10228TC) and cod. 471003 (batch 09724CE), respectively. [0155] The lignins of the Acetosolv type, of the Organosolv type and of the Kraft type used have the following elemental composition: The lignins of the Acetosolv type, of the Organosolv type and of the Kraft type used have the following elemental composition: [0156] C % 67.1; H % 5.3; N % 0.1; S % 0.0; O % 27.6 (lignin of the Acetosolv type); [0157] C % 66.7; H % 5.3; N % 0.2; S % 0.0; O % 28.9 (lignin of the Organosolv type); [0158] C % 63.3; H % 6.9; N % 0.2; S % 4.3; O % 25.4; inorganic ashes 17.5% (lignin of the Kraft type). [0159] 10 g of lignin were added to a stirred 0.5 1 Hastelloy C autoclave containing 100 g of a solvent (the type of solvent is reported in Table 1) and a catalyst (the type of catalyst is reported in Table 1). The autoclave was closed and pressurized with about 5 MPa of hydrogen at room temperature (25 C.). [0160] The autoclave was then stirred at 600 rpm and heated to the temperature and for the time reported in Table 1. At the end, the autoclave was left to cool to room temperature (25 C.), again under stirring, and the gas released was measured by means of a liters counter and analyzed by means of gas chromatography in order to determine the content of C1-C4 hydrocarbons and carbon monoxide and carbon dioxide. [0161] The mixture obtained, comprising a first liquid phase and a solid phase, was filtered obtaining a first liquid phase comprising part of the depolymerized lignin and a solid phase comprising the catalyst and the remaining part of the depolymerized lignin. [0162] Said liquid phase was subjected to evaporation in order to recover the depolymerized lignin (fraction 1) and the solvent which can be re-used for the hydrogenolysis of lignin. [0163] Said solid phase was subjected to extraction with 200 ml of acetone obtaining a solution comprising depolymerized lignin and catalyst. Said solution was filtered so as to obtain a solid residue comprising the catalyst and a second liquid phase comprising depolymerized lignin and acetone. [0164] The depolymerized lignin was recovered by evaporation of the acetone (fraction 2). Said fraction 2 and said fraction 1 were joined and sent to the hydrotreating reactor. [0165] The above solid residue comprising the catalyst was dried in an oven, at 110 C., for 24 hours and subsequently calcined at about 500 C., for 6 hours, in the air. The difference in weight between the dried catalyst and the calcined catalyst in relation to the starting lignin provides the residue reported in Table 1. The calcined catalyst can be re-used for the hydrogenolysis of lignin. [0166] As reported above, FIG. 1 indicates a gas chromatography/mass spectrometry (GC-MS) typical of the depolymerized lignin, obtained operating as described in Example 9 reported in Table 1, where, in the abscissa is reported the analysis time and in the ordinate is reported the abundance of the various compounds present. The gas chromatography/mass spectrometry (GC-MS) was carried out using an Agilent gas chromatograph mod. 7890 equipped with a Mass Spectrometry Detector MSD 5975C. As can be seen in FIG. 1, the depolymerized lignin obtained as described above comprises phenols, alkyl phenols and methoxy alkyl phenols. [0167] The depolymerized lignin obtained after joining said fraction 1 and said fraction 2 was weighed and subjected to elemental analysis by means of a Thermo Scientific Flash CHNS-O analyzer, in order to determine its content of carbon, hydrogen, nitrogen, sulphur and, by difference, oxygen: the data obtained are reported in Table 2. From the data reported in Table 2, it can be deduced that during the hydrogenolysis, a partial deoxygenation of lignin is obtained. [0168] From the data reported in Table 1, it can also be deduced that the lignin of the Acetosolv type and the lignin of the Organosolv type, after hydrogenolysis, are completely soluble in acetone, the solvent used for recovering them (Examples 7-11 and 13), whereas, for the lignin of the Kraft type, an insoluble residue equal to 4% by weight with respect to the total weight of the starting lignin (Example 12) can be observed. It can also be deduced that the presence of the catalyst is essential: Example 4 carried out in the absence of the catalyst, in fact, shows a residue of lignin (33% by weight with respe...

Reference： [1]Patent: US2013/60071,2013,A1 .Location in patent: Paragraph 0153-0168

46
[ 1126-20-1 ]
[ 2525-02-2 ]

Reference： [1]Patent: US2014/135393,2014,A1

47
[ 120-80-9 ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 1 h / 20 °C 1.2: 5.5 h / 20 - 70 °C 2.1: 2 h / 170 °C / Inert atmosphere 3.1: palladium 10% on activated carbon; methanol / 2 h / 20 °C
	Multi-step reaction with 2 steps 1: copper(l) chloride; sodium carbonate / water / 0.5 h / 20 °C 2: hydrogen; palladium 10% on activated carbon / methanol / 1 h / 20 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (IN) - US2014/135393, 2014, A1
[2]Horii, Toshihiro; Itagaki, Sawako; Kawano, Tomikazu; Miyoshi, Akihito; Murakami, Nobutoshi; Tamura, Satoru [Chemical and Pharmaceutical Bulletin, 2020, vol. 68, # 8, p. 784 - 790]

48
[ 2525-02-2 ]
[ 149-73-5 ]
(±)-2-methoxy-5-propyl-1,3-benzodioxole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With Amberlyst 15 In toluene for 4h; Inert atmosphere; Molecular sieve; Reflux;

Reference： [1]Gaudin, Jean-Marc; De Saint Laumer, Jean-Yves [European Journal of Organic Chemistry, 2015, vol. 2015, # 7, p. 1437 - 1447]

49
[ 1445-45-0 ]
[ 2525-02-2 ]
(±)-2-methoxy-2-methyl-5-propyl-1,3-benzodioxole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With Amberlyst 15 In toluene for 4h; Inert atmosphere; Molecular sieve; Reflux;

Reference： [1]Gaudin, Jean-Marc; De Saint Laumer, Jean-Yves [European Journal of Organic Chemistry, 2015, vol. 2015, # 7, p. 1437 - 1447]

50
[ 621-76-1 ]
[ 2525-02-2 ]
(±)-2-propoxy-5-propyl-1,3-benzodioxole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With Amberlyst 15 In toluene for 4h; Inert atmosphere; Molecular sieve; Reflux;

Reference： [1]Gaudin, Jean-Marc; De Saint Laumer, Jean-Yves [European Journal of Organic Chemistry, 2015, vol. 2015, # 7, p. 1437 - 1447]

51
[ 2785-87-7 ]
[ 621-27-2 ]
[ 58539-27-8 ]
[ 2525-02-2 ]
[ 62103-69-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: copper(l) iodide; 2-Picolinic acid; potassium phosphate / dimethyl sulfoxide / 20 h / 100 °C / Glovebox; Sealed tube 2.1: hydrogen; platinum-nickel nanoclusters on activated carbon; potassium hexamethylsilazane / m-xylene / 24 h / 180 °C / 775.74 Torr 2.2: 1 h / 65 °C
	Multi-step reaction with 3 steps 1.1: copper(l) iodide; 2-Picolinic acid; potassium phosphate / dimethyl sulfoxide / 20 h / 100 °C / Glovebox; Sealed tube 2.1: hydrogen; palladium on activated carbon / tetrahydrofuran; methanol / 12 h / 22 °C / 760.05 Torr / Sealed tube 3.1: hydrogen; platinum-nickel nanoclusters on activated carbon; potassium hexamethylsilazane / m-xylene / 24 h / 180 °C / 775.74 Torr 3.2: 1 h / 65 °C

Reference： [1]Gao, Fang; Webb, Jonathan D.; Hartwig, John F. [Angewandte Chemie - International Edition, 2016, vol. 55, # 4, p. 1474 - 1478][Angew. Chem., 2016, vol. 128, # 4, p. 1496 - 1500,5]
[2]Gao, Fang; Webb, Jonathan D.; Hartwig, John F. [Angewandte Chemie - International Edition, 2016, vol. 55, # 4, p. 1474 - 1478][Angew. Chem., 2016, vol. 128, # 4, p. 1496 - 1500,5]

52
2-(benzyloxy)-5-ethyl-1-methoxy-3-(2-methoxy-4-propylphenoxy)benzene [ No CAS ]
[ 621-27-2 ]
[ 1124-39-6 ]
[ 2785-89-9 ]
[ 58539-27-8 ]
[ 66125-16-4 ]
[ 2525-02-2 ]
[ 62103-69-9 ]
5-ethyl-3-methoxybenzene-1,2-diol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 1474 - 1478
Angew. Chem.,2016,vol. 128,p. 1496 - 1500,5
[2]Angewandte Chemie - International Edition,2016,vol. 55,p. 1474 - 1478
Angew. Chem.,2016,vol. 128,p. 1496 - 1500,5

53
4-ethyl-2-methoxy-6-(2-methoxy-4-propylphenoxy)phenol [ No CAS ]
[ 621-27-2 ]
[ 1124-39-6 ]
[ 2785-89-9 ]
[ 58539-27-8 ]
[ 66125-16-4 ]
[ 2525-02-2 ]
[ 62103-69-9 ]
5-ethyl-3-methoxybenzene-1,2-diol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 1474 - 1478
Angew. Chem.,2016,vol. 128,p. 1496 - 1500,5

54
[ 40649-36-3 ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	With iodine; oxygen; dimethyl sulfoxide at 80℃; for 12h;

Reference： [1]Liang, Yu-Feng; Li, Xinyao; Wang, Xiaoyang; Zou, Miancheng; Tang, Conghui; Liang, Yujie; Song, Song; Jiao, Ning [Journal of the American Chemical Society, 2016, vol. 138, # 37, p. 12271 - 12277]

55
4-(2-iodopropyl)catechol [ No CAS ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With aluminium(III) iodide In hexane at 80℃; for 18h;

Reference： [1]Sang, Dayong; Yao, Ming; Tian, Juan; Chen, Xiaoman; Li, Li; Zhan, Hongju; You, Linhong [Synlett, 2017, vol. 28, # 1, p. 138 - 142]

56
[ 2525-02-2 ]
[ 121-33-5 ]
C₂₆H₃₀O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With sulfuric acid In ethanol at 10 - 20℃; for 48h;

Reference： [1]Zhao, Shou; Abu-Omar, Mahdi M. [Macromolecules, 2017, vol. 50, # 9, p. 3573 - 3581]

57
[ 2525-02-2 ]
[ 134-96-3 ]
C₂₇H₃₂O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	With sulfuric acid In ethanol at 10 - 20℃; for 48h;

Reference： [1]Zhao, Shou; Abu-Omar, Mahdi M. [Macromolecules, 2017, vol. 50, # 9, p. 3573 - 3581]

58
[ 2525-02-2 ]
[ 123-08-0 ]
C₂₅H₂₈O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With sulfuric acid In ethanol at 10 - 20℃; for 48h;

Reference： [1]Zhao, Shou; Abu-Omar, Mahdi M. [Macromolecules, 2017, vol. 50, # 9, p. 3573 - 3581]

59
[ 58539-27-8 ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With hydrogen bromide In water at 120℃; for 20h;

Reference： [1]Zhao, Shou; Abu-Omar, Mahdi M. [Macromolecules, 2017, vol. 50, # 9, p. 3573 - 3581]

60
C₂₁H₄₀O₂Si₂ [ No CAS ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	AnI3u4NF.3H20 (315.5 mg, 2.1 mmol, 2.1 equiv) was slowly added (approximately 5 mi, under argon,solution of ha (380.7 mg; 1.0 mmol, 1 equivalent) inof THF. The solution was stirred for 1 h at 20° C.volatile compounds were then evaporated oil under vacuum and 4 ml of dichioromethane were added. Finally, compound ha was purified on a silica column using an elution gradient ranging from 50% dichioromethane to 50% ethyl acetate. The evaporation of the solvents results in the obtaining4-propylbenzene-1 ,2-diol (141.5 mg; 0.9 mmol; 84%)form of a colorless oil.

Reference： [1]Current Patent Assignee: COMMISSARIAT A L'ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES - US2017/137446, 2017, A1 Location in patent: Paragraph 0267

61
[ 2525-02-2 ]
C₁₁H₁₄O₄ [ No CAS ]
C₁₁H₁₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium methylate / 28 h / Inert atmosphere; Reflux; Molecular sieve 2: zinc(II) acetate dihydrate / 16 h / 50 °C / Sealed tube

Reference： [1]Dobi, Zoltán; Reddy, B. Narendraprasad; Renders, Evelien; Van Raemdonck, Laurent; Mensch, Carl; De Smet, Gilles; Chen, Chen; Bheeter, Charles; Sergeyev, Sergey; Herrebout, Wouter A.; Maes, Bert U. W. [ChemSusChem, 2019, vol. 12, # 13, p. 3103 - 3114]

62
[ 2525-02-2 ]
C₁₂H₁₆O₄ [ No CAS ]
C₁₂H₁₆O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium methylate / 28 h / Inert atmosphere; Reflux; Molecular sieve 2: zinc(II) acetate dihydrate / 16 h / 50 °C / Sealed tube

Reference： [1]Dobi, Zoltán; Reddy, B. Narendraprasad; Renders, Evelien; Van Raemdonck, Laurent; Mensch, Carl; De Smet, Gilles; Chen, Chen; Bheeter, Charles; Sergeyev, Sergey; Herrebout, Wouter A.; Maes, Bert U. W. [ChemSusChem, 2019, vol. 12, # 13, p. 3103 - 3114]

63
[ 2525-02-2 ]
C₁₃H₁₈O₄ [ No CAS ]
C₁₃H₁₈O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium methylate / 28 h / Inert atmosphere; Reflux; Molecular sieve 2: zinc(II) acetate dihydrate / 16 h / 50 °C / Sealed tube

Reference： [1]Dobi, Zoltán; Reddy, B. Narendraprasad; Renders, Evelien; Van Raemdonck, Laurent; Mensch, Carl; De Smet, Gilles; Chen, Chen; Bheeter, Charles; Sergeyev, Sergey; Herrebout, Wouter A.; Maes, Bert U. W. [ChemSusChem, 2019, vol. 12, # 13, p. 3103 - 3114]

64
[ 2525-02-2 ]
C₁₄H₂₀O₄ [ No CAS ]
C₁₄H₂₀O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium methylate / 28 h / Inert atmosphere; Reflux; Molecular sieve 2: zinc(II) acetate dihydrate / 16 h / 50 °C / Sealed tube

Reference： [1]Dobi, Zoltán; Reddy, B. Narendraprasad; Renders, Evelien; Van Raemdonck, Laurent; Mensch, Carl; De Smet, Gilles; Chen, Chen; Bheeter, Charles; Sergeyev, Sergey; Herrebout, Wouter A.; Maes, Bert U. W. [ChemSusChem, 2019, vol. 12, # 13, p. 3103 - 3114]

65
[ 2525-02-2 ]
C₁₉H₂₀O₄ [ No CAS ]
C₁₉H₂₀O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium methylate / 28 h / Inert atmosphere; Reflux; Molecular sieve 2: zinc(II) acetate dihydrate / 2-methyltetrahydrofuran / 16 h / 50 °C / Sealed tube

Reference： [1]Dobi, Zoltán; Reddy, B. Narendraprasad; Renders, Evelien; Van Raemdonck, Laurent; Mensch, Carl; De Smet, Gilles; Chen, Chen; Bheeter, Charles; Sergeyev, Sergey; Herrebout, Wouter A.; Maes, Bert U. W. [ChemSusChem, 2019, vol. 12, # 13, p. 3103 - 3114]

66
[ 2525-02-2 ]
C₂₄H₂₂O₄ [ No CAS ]
C₂₄H₂₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium methylate / 28 h / Inert atmosphere; Reflux; Molecular sieve 2: zinc(II) acetate dihydrate / 2-methyltetrahydrofuran / 16 h / 50 °C / Sealed tube

Reference： [1]Dobi, Zoltán; Reddy, B. Narendraprasad; Renders, Evelien; Van Raemdonck, Laurent; Mensch, Carl; De Smet, Gilles; Chen, Chen; Bheeter, Charles; Sergeyev, Sergey; Herrebout, Wouter A.; Maes, Bert U. W. [ChemSusChem, 2019, vol. 12, # 13, p. 3103 - 3114]

67
[ 2525-02-2 ]
C₂₁H₃₁NO₆ [ No CAS ]
C₂₁H₃₁NO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium methylate / 28 h / Inert atmosphere; Reflux; Molecular sieve 2: zinc(II) acetate dihydrate / 2-methyltetrahydrofuran / 16 h / 50 °C / Sealed tube

Reference： [1]Dobi, Zoltán; Reddy, B. Narendraprasad; Renders, Evelien; Van Raemdonck, Laurent; Mensch, Carl; De Smet, Gilles; Chen, Chen; Bheeter, Charles; Sergeyev, Sergey; Herrebout, Wouter A.; Maes, Bert U. W. [ChemSusChem, 2019, vol. 12, # 13, p. 3103 - 3114]

68
[ 2525-02-2 ]
C₂₂H₃₀O₉ [ No CAS ]
C₂₂H₃₀O₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium methylate / 28 h / Inert atmosphere; Reflux; Molecular sieve 2: zinc(II) acetate dihydrate / 2-methyltetrahydrofuran / 16 h / 50 °C / Sealed tube

Reference： [1]Dobi, Zoltán; Reddy, B. Narendraprasad; Renders, Evelien; Van Raemdonck, Laurent; Mensch, Carl; De Smet, Gilles; Chen, Chen; Bheeter, Charles; Sergeyev, Sergey; Herrebout, Wouter A.; Maes, Bert U. W. [ChemSusChem, 2019, vol. 12, # 13, p. 3103 - 3114]

69
[ 2525-02-2 ]
C₁₃H₁₈O₄ [ No CAS ]
C₁₃H₁₈O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium methylate / 28 h / Inert atmosphere; Reflux; Molecular sieve 2: zinc(II) acetate dihydrate / 16 h / 80 °C / Sealed tube

Reference： [1]Dobi, Zoltán; Reddy, B. Narendraprasad; Renders, Evelien; Van Raemdonck, Laurent; Mensch, Carl; De Smet, Gilles; Chen, Chen; Bheeter, Charles; Sergeyev, Sergey; Herrebout, Wouter A.; Maes, Bert U. W. [ChemSusChem, 2019, vol. 12, # 13, p. 3103 - 3114]

70
[ 2525-02-2 ]
C₁₆H₂₂O₄ [ No CAS ]
C₁₆H₂₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium methylate / 28 h / Inert atmosphere; Reflux; Molecular sieve 2: zinc(II) acetate dihydrate / 16 h / 80 °C / Sealed tube

Reference： [1]Dobi, Zoltán; Reddy, B. Narendraprasad; Renders, Evelien; Van Raemdonck, Laurent; Mensch, Carl; De Smet, Gilles; Chen, Chen; Bheeter, Charles; Sergeyev, Sergey; Herrebout, Wouter A.; Maes, Bert U. W. [ChemSusChem, 2019, vol. 12, # 13, p. 3103 - 3114]

71
[ 2525-02-2 ]
C₃₇H₅₆O₄ [ No CAS ]
C₃₇H₅₆O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium methylate / 28 h / Inert atmosphere; Reflux; Molecular sieve 2: zinc(II) acetate dihydrate / 2-methyltetrahydrofuran / 16 h / 80 °C / Sealed tube

Reference： [1]Dobi, Zoltán; Reddy, B. Narendraprasad; Renders, Evelien; Van Raemdonck, Laurent; Mensch, Carl; De Smet, Gilles; Chen, Chen; Bheeter, Charles; Sergeyev, Sergey; Herrebout, Wouter A.; Maes, Bert U. W. [ChemSusChem, 2019, vol. 12, # 13, p. 3103 - 3114]

72
[ 2525-02-2 ]
C₂₀H₃₀O₄ [ No CAS ]
C₂₀H₃₀O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium methylate / 28 h / Inert atmosphere; Reflux; Molecular sieve 2: zinc(II) acetate dihydrate / 16 h / 80 °C / Sealed tube

Reference： [1]Dobi, Zoltán; Reddy, B. Narendraprasad; Renders, Evelien; Van Raemdonck, Laurent; Mensch, Carl; De Smet, Gilles; Chen, Chen; Bheeter, Charles; Sergeyev, Sergey; Herrebout, Wouter A.; Maes, Bert U. W. [ChemSusChem, 2019, vol. 12, # 13, p. 3103 - 3114]

73
[ 2525-02-2 ]
C₁₆H₂₄O₅ [ No CAS ]
C₁₆H₂₄O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium methylate / 28 h / Inert atmosphere; Reflux; Molecular sieve 2: zinc(II) acetate dihydrate / 2-methyltetrahydrofuran / 16 h / 50 °C / Sealed tube

Reference： [1]Dobi, Zoltán; Reddy, B. Narendraprasad; Renders, Evelien; Van Raemdonck, Laurent; Mensch, Carl; De Smet, Gilles; Chen, Chen; Bheeter, Charles; Sergeyev, Sergey; Herrebout, Wouter A.; Maes, Bert U. W. [ChemSusChem, 2019, vol. 12, # 13, p. 3103 - 3114]

74
[ 2525-02-2 ]
C₁₄H₂₄N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium methylate / 28 h / Inert atmosphere; Reflux; Molecular sieve 2.1: zinc(II) acetate dihydrate / 16 h / 80 °C / Sealed tube 2.2: 16 h / 25 °C / Sealed tube

Reference： [1]Dobi, Zoltán; Reddy, B. Narendraprasad; Renders, Evelien; Van Raemdonck, Laurent; Mensch, Carl; De Smet, Gilles; Chen, Chen; Bheeter, Charles; Sergeyev, Sergey; Herrebout, Wouter A.; Maes, Bert U. W. [ChemSusChem, 2019, vol. 12, # 13, p. 3103 - 3114]

75
[ 2525-02-2 ]
benzyl 2-hydroxy-5-propylphenyl carbonate [ No CAS ]
benzyl 2-hydroxy-4-propylphenyl carbonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium methylate / 28 h / Inert atmosphere; Reflux; Molecular sieve 2: zinc(II) acetate dihydrate / 16 h / 50 °C / Sealed tube
	Multi-step reaction with 2 steps 1: sodium methylate / 28 h / Inert atmosphere; Reflux; Molecular sieve 2: zinc(II) acetate dihydrate / 16 h / 50 °C / Sealed tube

Reference： [1]Dobi, Zoltán; Reddy, B. Narendraprasad; Renders, Evelien; Van Raemdonck, Laurent; Mensch, Carl; De Smet, Gilles; Chen, Chen; Bheeter, Charles; Sergeyev, Sergey; Herrebout, Wouter A.; Maes, Bert U. W. [ChemSusChem, 2019, vol. 12, # 13, p. 3103 - 3114]
[2]Dobi, Zoltán; Reddy, B. Narendraprasad; Renders, Evelien; Van Raemdonck, Laurent; Mensch, Carl; De Smet, Gilles; Chen, Chen; Bheeter, Charles; Sergeyev, Sergey; Herrebout, Wouter A.; Maes, Bert U. W. [ChemSusChem, 2019, vol. 12, # 13, p. 3103 - 3114]

76
[ 2525-02-2 ]
[ 616-38-6 ]
5-propyl-benzo[1,3]dioxol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium methylate for 28h; Inert atmosphere; Reflux; Molecular sieve;

Reference： [1]Dobi, Zoltán; Reddy, B. Narendraprasad; Renders, Evelien; Van Raemdonck, Laurent; Mensch, Carl; De Smet, Gilles; Chen, Chen; Bheeter, Charles; Sergeyev, Sergey; Herrebout, Wouter A.; Maes, Bert U. W. [ChemSusChem, 2019, vol. 12, # 13, p. 3103 - 3114]

77
[ 2785-87-7 ]
[ 645-56-7 ]
[ 23950-98-3 ]
[ 2525-02-2 ]
[ 52204-65-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In water at 120℃; for 3h;

Reference： [1]Wang, Qiuyue; Chen, Yufang; Yang, Guanheng; Deng, Ping; Lu, Xinqing; Ma, Rui; Fu, Yanghe; Zhu, Weidong [ChemCatChem, 2020, vol. 12, # 19, p. 4930 - 4938]

78
[ 6766-82-1 ]
[ 645-56-7 ]
[ 2785-87-7 ]
[ 23950-98-3 ]
[ 2525-02-2 ]
C₁₁H₂₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In water at 120℃; for 3h;

Reference： [1]Wang, Qiuyue; Chen, Yufang; Yang, Guanheng; Deng, Ping; Lu, Xinqing; Ma, Rui; Fu, Yanghe; Zhu, Weidong [ChemCatChem, 2020, vol. 12, # 19, p. 4930 - 4938]

79
[ 2525-02-2 ]
4-(prop-1-yl)-5-carboxymethyl-2-furanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With formic acid; Peroxyformic acid; ferrous ammonium sulphate hexahydrate In water for 22h; Green chemistry;

Reference： [1]Coupé, Florentin; Petitjean, Laurène; Anastas, Paul T.; Caijo, Frédéric; Escande, Vincent; Darcel, Christophe [Green Chemistry, 2020, vol. 22, # 18, p. 6204 - 6211]

80
[ 2785-87-7 ]
[ 645-56-7 ]
[ 1678-92-8 ]
[ 103-65-1 ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; niobium(V) oxide; ruthenium-carbon composite; hydrogen In water at 250℃; for 12h; Autoclave;

Reference： [1]Abu-Omar, Mahdi M.; Ford, Peter C.; Li, Simin; Liu, Baoyuan; Luo, Zhongyang; Truong, Julianne [Green Chemistry, 2020, vol. 22, # 21, p. 7406 - 7416]

81
1,2-diethoxy-4-propylbenzene [ No CAS ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With hydrogenchloride In water at 250℃; for 6h; Autoclave; Inert atmosphere; Green chemistry;

Reference： [1]Bomon, Jeroen; Bal, Mathias; Achar, Tapas Kumar; Sergeyev, Sergey; Wu, Xian; Wambacq, Ben; Lemière, Filip; Sels, Bert F.; Maes, Bert U. W. [Green Chemistry, 2021, vol. 23, # 5, p. 1995 - 2009]

82
[ 2785-87-7 ]
[ 2525-02-2 ]
[ 120-80-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 79% 2: 5%	With niobium(V) oxide In water at 300℃; for 3h; Autoclave; Inert atmosphere;

Reference： [1]Bomon, Jeroen; Bal, Mathias; Achar, Tapas Kumar; Sergeyev, Sergey; Wu, Xian; Wambacq, Ben; Lemière, Filip; Sels, Bert F.; Maes, Bert U. W. [Green Chemistry, 2021, vol. 23, # 5, p. 1995 - 2009]

83
[ 2525-02-2 ]
[ 75-03-6 ]
1,2-diethoxy-4-propylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate In ethanol for 24h; Reflux;

Reference： [1]Bomon, Jeroen; Bal, Mathias; Achar, Tapas Kumar; Sergeyev, Sergey; Wu, Xian; Wambacq, Ben; Lemière, Filip; Sels, Bert F.; Maes, Bert U. W. [Green Chemistry, 2021, vol. 23, # 5, p. 1995 - 2009]

84
[ 5888-52-8 ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With hydrogenchloride In water at 250℃; for 6h; Autoclave; Inert atmosphere; Green chemistry;

Reference： [1]Bomon, Jeroen; Bal, Mathias; Achar, Tapas Kumar; Sergeyev, Sergey; Wu, Xian; Wambacq, Ben; Lemière, Filip; Sels, Bert F.; Maes, Bert U. W. [Green Chemistry, 2021, vol. 23, # 5, p. 1995 - 2009]

85
[ 2525-02-2 ]
C₉H₁₁O₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With oxygen; extradiol dioxygenase AphC In aq. buffer at 25℃; Enzymatic reaction;

Reference： [1]Bajwa, Harbir; Chan, Anson C. K.; Eltis, Lindsay D.; Grigg, Jason C.; McGeehan, John E.; Murphy, Michael E. P.; Navas, Laura E.; Wolf, Megan E.; Zahn, Michael [Journal of Biological Chemistry, 2022, vol. 298, # 5]

86
[ 621-27-2 ]
[ 4693-31-6 ]
[ 2525-02-2 ]

Yield	Reaction Conditions	Operation in experiment
	With D-Glucose; oxygen; triple recombinant E_. coli cells coexpressing P₄₅₀ BM₃ monooxygenase F₈₇V/L₁₈₈P/R₄₇I and glucose dehydrogenase; NADPH In aq. phosphate buffer at 22℃; for 2h; Green chemistry; Enzymatic reaction; regioselective reaction;
	With D-Glucose; oxygen; triple recombinant E_. coli cells coexpressing P₄₅₀ BM₃ monooxygenase F₈₇V/R₄₇I/Y₅₁F and glucose dehydrogenase; NADPH In aq. phosphate buffer; dimethyl sulfoxide at 25℃; for 12h; Green chemistry; Enzymatic reaction; Overall yield = 75.6 percent; Overall yield = 23 mg; regioselective reaction;

Reference： [1]Gaikaiwari, Anand Raghavendra; Li, Ren-Jie; Li, Xirui; Li, Zhi; Tian, Kaiyuan [ACS Catalysis, 2022, p. 5939 - 5948]
[2]Gaikaiwari, Anand Raghavendra; Li, Ren-Jie; Li, Xirui; Li, Zhi; Tian, Kaiyuan [ACS Catalysis, 2022, p. 5939 - 5948]

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	2525-02-2	MDL No. :	MFCD00870985
Formula :	C₉H₁₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SCTPZNJTGOGSQD-UHFFFAOYSA-N
M.W :	152.19	Pubchem ID :	97638
Synonyms :

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	45.07
TPSA :	40.46 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) :	-5.51 cm/s

[ CAS No. 2525-02-2 ] {[proInfo.proName]}

Quality Control of [ 2525-02-2 ]

Related Doc. of [ 2525-02-2 ]

Product Details of [ 2525-02-2 ]

Calculated chemistry of [ 2525-02-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 2525-02-2 ]

Application In Synthesis of [ 2525-02-2 ]

[ 2525-02-2 ] Synthesis Path-Downstream 1~86

Related Functional Groups of
[ 2525-02-2 ]

Aryls

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Log Po/w (iLOGP) :	1.82
Log Po/w (XLOGP3) :	2.42
Log Po/w (WLOGP) :	2.05
Log Po/w (MLOGP) :	1.8
Log Po/w (SILICOS-IT) :	1.99
Consensus Log Po/w :	2.02

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

Log S (ESOL) :	-2.58
Solubility :	0.4 mg/ml ; 0.00263 mol/l
Class :	Soluble
Log S (Ali) :	-2.91
Solubility :	0.186 mg/ml ; 0.00122 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.43
Solubility :	0.569 mg/ml ; 0.00374 mol/l
Class :	Soluble

PAINS :	1.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.11

Signal Word:	Danger	Class:	9
Precautionary Statements:	P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330	UN#:	3077
Hazard Statements:	H302-H319-H372-H410	Packing Group:	Ⅲ
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. 2525-02-2 ] {[proInfo.proName]}

Quality Control of [ 2525-02-2 ]

Related Doc. of [ 2525-02-2 ]

Product Details of [ 2525-02-2 ]

Calculated chemistry of [ 2525-02-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 2525-02-2 ]

Application In Synthesis of [ 2525-02-2 ]

[ 2525-02-2 ] Synthesis Path-Downstream 1~86

Related Functional Groups of [ 2525-02-2 ]

Aryls

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 2525-02-2 ]