[ CAS No. 2491-38-5 ]

Name: 2491-38-5|2-Bromo-1-(4-hydroxyphenyl)ethanone|98%
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{[proInfo.proName]} (Synonyms:α-Bromo-4-hydroxyacetophenone; 2-Bromo-4'-hydroxyacetophenone; 4-Hydroxyphenacyl bromide; 4-Hydroxyphenacyl bromide; SHP-1 Inhibitor II) ,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 2491-38-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 2491-38-5 ]

Product Details of [ 2491-38-5 ]

CAS No. :	2491-38-5	MDL No. :	MFCD00072424
Formula :	C₈H₇BrO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LJYOFQHKEWTQRH-UHFFFAOYSA-N
M.W :	215.04 g/mol	Pubchem ID :	4964
Synonyms :	1. 2-Bromo-4'-hydroxyacetophenone

Calculated chemistry of [ 2491-38-5 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	46.53
TPSA :	37.3 Å²

Pharmacokinetics

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) :	-6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.39
Log Po/w (XLOGP3) :	1.83
Log Po/w (WLOGP) :	1.97
Log Po/w (MLOGP) :	1.59
Log Po/w (SILICOS-IT) :	2.21
Consensus Log Po/w :	1.8

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.6
Solubility :	0.543 mg/ml ; 0.00252 mol/l
Class :	Soluble
Log S (Ali) :	-2.23
Solubility :	1.26 mg/ml ; 0.00584 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.04
Solubility :	0.198 mg/ml ; 0.000923 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.4

Safety of [ 2491-38-5 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P501-P260-P270-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P406-P405	UN#:	3261
Hazard Statements:	H302-H314-H290	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 2491-38-5 ]

* 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.

Upstream synthesis route of [ 2491-38-5 ]
Downstream synthetic route of [ 2491-38-5 ]

[ 2491-38-5 ] Synthesis Path-Upstream 1~9

1
[ 100-66-3 ]
[ 598-21-0 ]
[ 2491-38-5 ]
[ 2491-36-3 ]

Reference： [1] Patent: US2838570, 1955, ,
[2] Patent: US2838570, 1955, ,
[3] Patent: US2838570, 1955, ,

2
[ 99-93-4 ]
[ 2491-38-5 ]
[ 1836-06-2 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1992, vol. 65, # 1, p. 295 - 297

3
[ 2491-38-5 ]
[ 100-39-0 ]
[ 4254-67-5 ]

Yield	Reaction Conditions	Operation in experiment
43%	With silver carbonate In tetrahydrofuran at 0 - 20℃; for 16 h;	Step 1: Preparation of l-(4-(benzyloxy)phenyl)-2-bromoethanone [00170] To a solution of 2-bromo- 1 -(4-hydroxyphenyl)ethanone (2 g, 9.3 mmol) in tetrahydrofuran (70 mL) was added silver carbonate (5.128 g, 18.6 mmol) and the reaction mixture was cooled to 0 °C. Benzyl bromide (1.32 m L, 11.16 mmol) was added drop wise and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was filtered through celite, the filtrate was diluted with ethyl acetate (200 mL) and washed with water (60 mL x 2). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The crude was purified by column chromatography using 6percent ethyl acetate in hexane to afford title l-(4-(benzyloxy)phenyl)-2-bromoethanone (1.22 g, 43percent yield) as a white solid. Calculated M+H: 306.17; Found M+H: 306.

Reference： [1] Patent: WO2016/49165, 2016, A1, . Location in patent: Paragraph 00170

4
[ 2491-38-5 ]
[ 4254-67-5 ]

Reference： [1] Journal of Organic Chemistry, 2015, vol. 80, # 19, p. 9713 - 9721
[2] Journal of Organic Chemistry, 2015, vol. 80, # 19, p. 9713 - 9721

5
[ 2491-38-5 ]
[ 17194-82-0 ]

Reference： [1] Synthetic Communications, 1997, vol. 27, # 7, p. 1133 - 1141

6
[ 2491-38-5 ]
[ 124-41-4 ]
[ 32136-81-5 ]

Reference： [1] Journal of Medicinal Chemistry, 1988, vol. 31, # 1, p. 55 - 59
[2] Chemical Communications, 2015, vol. 51, # 34, p. 7349 - 7351
[3] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 191 - 194
[4] Patent: WO2004/52816, 2004, A1, . Location in patent: Page 38
[5] Patent: WO2004/113273, 2004, A1, . Location in patent: Page 37

7
[ 2491-38-5 ]
[ 32136-81-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium hydroxide In methanol	EXAMPLE 3 Preparation of alpha-methoxy-4-hydroxyacetophenone 2 g of alpha-bromo-4-hydroxyacetophenone are dissolved in 11 g of methanol. 30 g of a saturated solution of sodium hydroxide in methanol (1 g NaOH/ 4.2 ml methanol) is added dropwise to the alpha-bromo-4-hydroxyacetophenone solution. After the addition is complete, the solution is added to 30 g of ice and acidified to pH 6. Alpha-methoxy-4-hydroxyacetophenone precipitates out and is filtered and dried to a greenish yellow product in about 85percent yield; the product is determined by 1-H-NMR to be substantially pure.

Reference： [1] Patent: US5107034, 1992, A,

8
[ 2491-38-5 ]
[ 7440-44-0 ]
[ 32136-81-5 ]

Reference： [1] Patent: US5107034, 1992, A,

9
[ 2491-38-5 ]
[ 19745-72-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 5, p. 2550 - 2557
[2] Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 8, p. 628 - 635

[ 2491-38-5 ] Synthesis Path-Downstream 1~59

1
[ 2491-38-5 ]
[ 75-16-1 ]
[ 770-39-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 1373 - 1380

2
[ 2491-38-5 ]
[ 75-16-1 ]
[ 770-39-8 ]
[ 98815-43-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 1373 - 1380

3
[ 2491-38-5 ]
[ 75-16-1 ]
[ 770-39-8 ]
[ 98815-43-1 ]
4-(2-Bromo-1-hydroxy-1-methyl-ethyl)-phenol [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 1373 - 1380

4
[ 2491-38-5 ]
[ 124-41-4 ]
[ 32136-81-5 ]

Yield	Reaction Conditions	Operation in experiment
		P10.1 1.8 g of 2-BROMO-1- (4-HYDROXY-PHENYL)-ETHANONE in 10 ml of methanol are added dropwise to 16 ml of 5.4M sodium methoxide in methanol and 50 ml of methanol, and stirring is carried out for 30 minutes at 60C. The reaction mixture is concentrated and the residue is taken up in water and adjusted to pH 1 with concentrated hydrochloric acid. Extraction with ethyl acetate is then carried out, the organic phase is concentrated and the crude product is purified over silica gel. 1- (4-HYDROXY-PHENYL)-2-METHOXY-ETHANONE is OBTAINED.'H-NMR (CDCI3) 300MHZ : 3.50 (s, 3H), 4.68 (s, 2H), 6.23 (s, 1 H), 6.91 (d, 2H), 7.90 (d, 2H).
	In methanol; at 60.0℃; for 0.916667h;	3.0 g OF 2-BROMO-1- (4-HYDROXY-PHENYL)-ETHANONE in 25 ML of methanol are added dropwise in the course of 10 minutes to a solution of 7.5 g of sodium METHANOLATE in 80 ml of methanol. Stirring is then carried out at 60C for 45 minutes. The reaction mixture is cooled, poured into dilute hydrochloric acid and extracted with ethyl acetate. After concentration of the organic phases and crystallisation from diethyl ether, 1- (4-HYDROXY-PHENYL)-2-METHOXY- ethanone is OBTAINED. 1H-NMR (CDCI3) 300MHZ : 3.50 (s, 3H), 4.70 (s, 2H), 6.62 (s, 1H), 6.91 (d, 2H), 7.89 (d, 2H)

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 55 - 59
[2]Chemical Communications,2015,vol. 51,p. 7349 - 7351
[3]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 191 - 194
[4]Patent: WO2004/52816,2004,A1 .Location in patent: Page 38
[5]Patent: WO2004/113273,2004,A1 .Location in patent: Page 37

5
[ 2491-38-5 ]
[ 99-93-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With diethyl ether In lithium hydroxide monohydrate at 20℃; for 3h; Schlenk technique; Irradiation;	3. General procedure for the reaction of reductive dehalogenation General procedure: To a 10 mL schlenk tube, 1 (0.2 mmol), H2O (1.6 mmol) and Et2O (4 mL) were added in sequence. The reaction mixture was stirred and irradiated by 40 W Kessil purple LED (390 nm) at room temperature . After the reaction was completed, the reaction mixture was purified by flash column chromatography using PE/EtOAc as the eluent to give the desired product.
93%	With DMBI In tetrahydrofuran for 3h; Heating;
85%	With sodium hydrogen telluride In ethyl acetate for 1h; Ambient temperature;

	Multi-step reaction with 3 steps 1.1: potassium carbonate / methanol / 20 °C 1.2: 1 h 2.1: hydrogenchloride / methanol; lithium hydroxide monohydrate; isopropanol / 4 h 3.1: aq. phosphate buffer / pH 5.6 / Irradiation
	Multi-step reaction with 2 steps 1: N,N,N-tributyl-1-butanaminium iodide; potassium carbonate / dichloromethane; lithium hydroxide monohydrate / 20 °C 2: bis[(2,2,2-trifluoroacetyl)oxy]palladium; 5,5'-bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-4,4'-bi-1,3-benzodioxole; hydrogen / propan-2-one / 24 h / 20 °C / 22502.3 Torr / Glovebox; Autoclave

Reference： [1]Chen, Jiajia; Chen, Jianhui; Luo, Yanshu; Xia, Yuanzhi; Zhang, Jinrong [Tetrahedron Letters, 2022]
[2]Chikashita, Hidenori; Ide, Hisao; Itoh, Kazuyoshi [Journal of Organic Chemistry, 1986, vol. 51, # 26, p. 5400 - 5405]
[3]Osuka, Atsuhiro; Suzuki, Hitomi [Chemistry Letters, 1983, p. 119 - 120]
[4]Bownik, Iwona; Šebej, Peter; Literák, Jaromír; Heger, Dominik; Šimek, Zdeněk; Givens, Richard S.; Klán, Petr [Journal of Organic Chemistry, 2015, vol. 80, # 19, p. 9713 - 9721]
[5]Chen, Jianzhong; Zhang, Zhenfeng; Liu, Delong; Zhang, Wanbin [Angewandte Chemie - International Edition, 2016, vol. 55, # 29, p. 8444 - 8447][Angew. Chem., 2016, vol. 128, # 29, p. 8584 - 8587]

6
[ 99-93-4 ]
[ 2491-38-5 ]
[ 1836-06-2 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1992,vol. 65,p. 295 - 297

7
[ 13031-43-1 ]
[ 2491-38-5 ]

Reference： [1]Russian Journal of Organic Chemistry,1994,vol. 30,p. 881 - 887
Zhurnal Organicheskoi Khimii,1994,vol. 30,p. 827 - 832
[2]Nippon Kagaku Zasshi,1959,vol. 80,p. 212
Chem.Abstr.,1961,p. 4406
[3]Letters in Organic Chemistry,2016,vol. 13,p. 672 - 677

8
[ 2491-38-5 ]
[ 27317-69-7 ]
[ 270090-90-9 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 2687 - 2697
[2]Journal of the American Chemical Society,1997,vol. 119,p. 8369 - 8370

9
[ 2491-38-5 ]
[ 5052-95-9 ]
[ 184716-27-6 ]

Yield	Reaction Conditions	Operation in experiment
	In butanone;	EXAMPLE 5 (R,S)-8-{2-hydroxy-2-[4-(quinol-2-ylmethoxy)phenyl]ethyl}-<strong>[5052-95-9]3,8-diaza-1-oxa-2-oxospiro[4,5]decane</strong> STR39 Step A 43.5 g (0.2 mol) of 4-bromoacetylphenol, 62.4 g (0.4 mol) of <strong>[5052-95-9]3,8-diaza-1-oxa-2-oxospiro[4,5]decane</strong> and 1500 ml of methyl ethyl ketone are introduced into a flask. The mixture is heated at reflux for 14 hours. The mixture is cooled and the crystals are suction-filtered and washed with a 10% sodium carbonate solution and then with water. Drying is carried out at 50 C. under 67 Pa. There are obtained 34.8 g of 8-{2-(4-hydroxyphenyl)-2-oxoethyl}-<strong>[5052-95-9]3,8-diaza-1-oxa-2-oxospiro[4,5]decane</strong>, m.p.(cap): 250 C.

Reference： [1]Patent: US5698567,1997,A

10
[ 2491-38-5 ]
[ 169315-44-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium azide In methanol; water at 0 - 20℃;	General procedure for α-azidoacetophenone synthesis General procedure: To a stirred solution of NaN3 (0.29 g, 4.4 mmol) in H2O (4 mL) was added α-bromoacetophenone (4.0 mmol) in MeOH (8 mL) dropwise at 0 C. The reaction mixture was warmed to room temperature and stirred for 2.5-3.5 h. After completion of the reaction, MeOH was removed under reduced pressure. The crude residue diluted with H2O (10 mL) and extracted with EtOAc (2 x 40 mL). The combined organic layer was washed with H2O (2 x 15 mL) and brine (15 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The crude was purified by column chromatography (EtOAc/hexane=1/5-1/3) to afford the pure α-azidoacetophenone as white solid.
92%	With sodium azide In water; acetone at 20℃;
47%	With sodium azide In N,N-dimethyl-formamide at 20℃; for 2h;

	With sodium azide; Aliquat 336 In toluene at 55℃;
	With sodium azide In ethanol; water at 20℃;
	With sodium azide
	With sodium azide In water; acetone for 24h;
	With sodium azide In acetone at 40℃; for 2h;	1 The resulting α-bromo-4-hydroxyacetophenone (1.075 g, 5.0 mmol) was dissolved in acetone (20 mL), Sodium azide (0.39 g, 6.0 mmol) was then added to the solution. Stir for 2 hours at 40°C. After cooling to room temperature, Pour 50 mL of water into the solution. Extract with ethyl acetate (3 x 50 mL) Liquid separation, The organic phase is dried over anhydrous sodium sulfate. Suction filtration The residue obtained after removal of the solvent under reduced pressure was separated by column chromatography (eluent: ethyl acetate/petroleum ether = 1:15, v/v). Alpha-azido-4-hydroxyacetophenone is obtained.
	With sodium azide In acetone at 20℃;	General Procedure for 2-Azido-Ketone Synthesis of phenacyl azides (2)2: General procedure: NaN3 (2.0 mmol) was added to a solution of the α-bromo-ketone (1.0 mmol) in acetone15 mL at room temperature. The reaction was stirred for 1-3 h. After addition of water theproduct was extracted with EtOAc, dried over NaSO4 and concentrated in vacuo. The crudeproduct was purified by column chromatography on silica gel (100-200 mesh) using an ethylacetate/hexane (9:1) to yield desired phenacyl azide.

Reference： [1]Damodar, Kongara; Shin, Sooyong; Jeon, Sung Ho; Lee, Jeong Tae [Tetrahedron Letters, 2021, vol. 85]
[2]Madea; Slanina; Klán [Chemical Communications, 2016, vol. 52, # 87, p. 12901 - 12904]
[3]Edegger, Klaus; Gruber, Christian C.; Poessl, Tina M.; Wallner, Sabine R.; Lavandera, Ivan; Faber, Kurt; Niehaus, Frank; Eck, Juergen; Oehrlein, Reinhold; Hafner, Andreas; Kroutil, Wolfgang [Chemical Communications, 2006, # 22, p. 2402 - 2404]
[4]Widler, Leo; Green, Jonathan; Missbach, Martin; Susa, Mira; Altmann, Eva [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 6, p. 849 - 852]
[5]Cuetos, Aníbal; Bisogno, Fabricio R.; Lavandera, Iván; Gotor, Vicente [Chemical Communications, 2013, vol. 49, # 26, p. 2625 - 2627]
[6]Lu, Xiao-Feng; Yang, Zheng; Huang, Nian-Yu; He, Hai-Bo; Deng, Wei-Qiao; Zou, Kun [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 17, p. 3726 - 3729]
[7]Salahi, Farbod; Purohit, Vatsal; Ferraudi, Guillermo; Stauffacher, Cynthia; Wiest, Olaf; Helquist, Paul [Organic Letters, 2018, vol. 20, # 9, p. 2547 - 2550]
[8]Current Patent Assignee: CHINA THREE GORGES UNIVERSITY - CN104788436, 2018, B Location in patent: Paragraph 0079; 0083
[9]Gour, Jitendra; Gatadi, Srikanth; Pooladanda, Venkatesh; Ghouse, Shaik Mahammad; Malasala, Satyaveni; Madhavi; Godugu, Chandraiah; Nanduri, Srinivas [Bioorganic Chemistry, 2019, vol. 93]

11
[ 2491-38-5 ]
[ 5029-61-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With nitric acid In methanol at 0 - 20℃; for 3h; Large scale;	S1 S1: 2.13kg of raw material 2-bromo-4'-hydroxyacetophenone (1 equivalent), its structural formula is:Dissolve in 10L (5 volumes) methanol, and cool the resulting solution A to 0 ° C,And add 0.63kg of nitric acid dropwise to solution A,After the dropwise addition is completed, the resulting reaction system is reacted at room temperature for 3 hours,After the reaction is completed, the material is discharged under ice water conditions.Centrifuge the product obtained from the discharge, use the centrifugal force generated by the centrifuge to separate the liquid and solid particles in the product obtained from the discharge, and dry the solid particles2.59 kg of intermediate I was obtained. Intermediate I was a nitro compound with the structural formula:In this step, intermediate I is obtained by dissolving 2-bromo-4'-hydroxyacetophenone as a raw material in concentrated sulfuric acid and adding nitric acid, and the reaction yield is 100%.
93%	With trifluoromethylsulfonic anhydride; tetramethylammonium nitrate In dichloromethane for 27h;

Reference： [1]Current Patent Assignee: SUZHOU KAIRUI MEDICINE SCIENCE TECH - CN111018902, 2020, A Location in patent: Paragraph 0014
[2]Shackelford, Scott A.; Anderson, Mark B.; Christie, Lance C.; Goetzen, Thomas; Guzman, Mark C.; Hananel, Martha A.; Kornreich, Wayne D.; Li, Haitao; Pathak, Ved P.; Rabinovich, Alex K.; Rajapakse, Ranjan J.; Truesdale, Larry K.; Tsank, Stella M.; Vazir, Haresh N. [Journal of Organic Chemistry, 2003, vol. 68, # 2, p. 267 - 275]

12
[ 1193-62-0 ]
[ 2491-38-5 ]
methyl 1-[2-(4-hydroxyphenyl)-2-oxoethyl]pyrrole-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		Step 1: To a chilled solution of methyl 1 H-pyrrole-2-carboxylate (1.0 g, 8.0 mmol) in dry DMF (20 ml.) was added sodium hydride (60% in mineral oil, 320 mg, 8.0 mmol)portionwise. The mixture was stirred at 0 C for 1 hour before a solution of 2-bromo-1-(4- hydroxyphenyl)ethanone (780 mg, 3.6 mmol) in DMF (5 ml.) was added. The resulting yellow solution was allowed to warm to room temperature. After 2.5 hours the reaction was complete (monitored by LCMS). A saturated aqueous solution of NH4CI (40 ml.) was added and the mixture was extracted with EtOAc (1 x 20 ml_). The organic layer was concentrated in vacuo to yield a residue that was purified by flash chromatography using the (Biotage SP4, 40 g cartridge, 0 to 100% EtOAc gradient in hexane) to give methyl 1-[2-(4- hydroxyphenyl)-2-oxoethyl]-1 H-pyrrole-2-carboxylate as a white solid (810 mg, yield 87%). 1H-NMR (400 MHz, d6-acetone): delta 3.66 (s, 3H), 5.86 (s, 2H), 6.16 (dd, 1 H, J 3.9, 2.6 Hz), 6.92 (dd, 1 H, J 4.0, 1 .8 Hz), 6.96-7.00 (m, 2H), 7.04-7.06 (m, 1 H), 7.95-8.00 (m, 2H, 9.23 (br s, 1 H).

Reference： [1]Patent: WO2011/94823,2011,A1 .Location in patent: Page/Page column 113
[2]Molecules,2004,vol. 9,p. 574 - 582

13
[ 2491-38-5 ]
[ 56718-71-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 191 - 194

14
[ 2491-38-5 ]
[ 14140-15-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;palladium 10% on activated carbon; In methanol; for 10h;	To a round bottom flask charged with 4-bromoacetylphenol (4.6 mmol) is added 15 mL methanol. 10 wt % Pd/C (10 wt %, 0.10 g) is then added to it and the mixture is hydrogenated using a balloon filled with hydrogen. The reaction allowed to sit for 10 hours at which time it's filtered through a pad of diatomaceous earth (Celite). The filtrate is then concentrated in vacuo to obtain 4-(2-bromoethyl)phenol as the purified product.

Reference： [1]Patent: US2006/83681,2006,A1 .Location in patent: Page/Page column 11

15
[ 631-58-3 ]
[ 108-20-3 ]
[ 2491-38-5 ]
4-(2-ethyl-4-thiazolyl)-phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.3 parts (40.2%)	In ethanol; water;	EXAMPLE 9 A mixture of 3.6 parts of <strong>[631-58-3]propanethioamide</strong>, 8.6 parts of 2-bromo-1-(4-hydroxyphenyl)ethanone and 79 parts of ethanol was stirred for 7 hours at reflux temperature. The reaction mixture was concentrated to 1/4 of its volume and 2,2'-oxybispropane was added to the residue. The precipitate was filtered off and taken up in water. After basifying with NH4 OH, the product was extracted with dichloromethane. The extract was dried, filtered and evaporated, yielding 3.3 parts (40.2%) of 4-(2-ethyl-4-thiazolyl)-phenol (interm. 17).

Reference： [1]Patent: US5100893,1992,A

16
[ 2491-38-5 ]
[ 7440-44-0 ]
[ 32136-81-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; In methanol; nitrogen; water; ethyl acetate;	EXAMPLE 4 Preparation of alpha-methoxy-4-hydroxyacetophenone In a nitrogen purged glove bag, 35.06 g (95%; 155 mmol) alpha-bromo-4-hydroxyacetophenone, dissolved in 350 ml methanol, are slowly added to a stirred solution of 69.9 g (91.29 mol) sodium methoxide in 660 ml methanol. About 40 minutes after the addition is complete, a solid (NaBr) precipitates out. After 2 hrs, the dark orange mixture is stripped of solvent. The yellow-orange residue is dissolved in 750 ml water. Once the pH is adjusted to 6, the aqueous solution is extracted by 3*250 ml ethyl acetate; the organic phase is dried over MgSO4 and the solvent is removed by roto-evaporation. The solid is then recrystallized from 180 ml boiling toluene (1.4 g carbon added) to give a light yellow material identified as alpha-methoxy-4-hydroxyacetophenone by GC, 1 H and 13 C NMR.

Reference： [1]Patent: US5107034,1992,A

17
[ 2491-38-5 ]
[ 32136-81-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium hydroxide; In methanol;	EXAMPLE 3 Preparation of alpha-methoxy-4-hydroxyacetophenone 2 g of alpha-bromo-4-hydroxyacetophenone are dissolved in 11 g of methanol. 30 g of a saturated solution of sodium hydroxide in methanol (1 g NaOH/ 4.2 ml methanol) is added dropwise to the alpha-bromo-4-hydroxyacetophenone solution. After the addition is complete, the solution is added to 30 g of ice and acidified to pH 6. Alpha-methoxy-4-hydroxyacetophenone precipitates out and is filtered and dried to a greenish yellow product in about 85% yield; the product is determined by 1-H-NMR to be substantially pure.

Reference： [1]Patent: US5107034,1992,A

18
[ 54326-16-8 ]
2N-hydrochloric acid [ No CAS ]
[ 2491-38-5 ]
5-chloro-1-(4-hydroxyphenacyl)pyrimidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; triethylamine;	EXAMPLE 20 5-Chloro-1-(4-hydroxyphenacyl)pyrimidin-2-one A suspension of <strong>[54326-16-8]5-chloropyrimidin-2-one</strong> (405 mg) and 2-bromo-4'-hydroxyacetophenone (646 mg) in triethylamine (1 ml) and ethanol (20 ml) was stirred at ambient temperature, giving a clear solution. A precipitate had formed after an hour. After 231/2 hours, 2N-hydrochloric acid (5 ml) was added to the suspension and the solid was collected. This was washed with ethanol to give the title pyrimidinone (679 mg,); m.p. 260 with decomposition; lambdamaxEtOH 224 nm (epsilon 17300), 282.5 nm (epsilon 15660), 353 nm (epsilon 4900).

Reference： [1]Patent: US4636509,1987,A

19
[ 2491-38-5 ]
[ 19745-72-3 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 2-bromo-4-hydroxyacetophenone 11 (20.0 mmol) in tetrahydrofuran (THF) (50 mL), hexamethylenetetramine(20.0 mmol) was added and stirred for 3 h at room temperature, and then the precipitated hexamethylenetetramine adduct 12 was filtered out. The adduct 12 was then heated with ethanol (80 mL) and concentrated HCl (8 mL) for 1 h at 45 C. After cooling, the inorganics were filtered out, the mixture was washed with ethanol (20 mL), and the solvent was distilled out completely under reduced pressure to obtain the desired compound 13. Then 14a-d (2.0 mmol), triethylamine (4.0 mmol), and EDCI·HCl (4.0 mmol), followed by HOBT (4.0 mmol), were added to a stirred solution of 13 (2.0 mmol) in CH2Cl2 (10 mL) and the mixture was stirred for 12 h at room temperature. Saturated Na2CO3 was added, the mixture was extracted with ethyl acetate, and the extracts were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by chromatography to give target compounds 15a-d.

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 2550 - 2557
[2]Chemical and Pharmaceutical Bulletin,2015,vol. 63,p. 628 - 635

20
[ 1445-39-2 ]
[ 2491-38-5 ]
[ 956499-77-7 ]

Yield	Reaction Conditions	Operation in experiment
		646 mg (corresponding to 3.0 mmol) of 2-bromo-4'-hydroxyacetophenone and 668 mg (corresponding to 3.0 mmol) of <strong>[1445-39-2]2-amino-5-iodopyrimidine</strong> were dissolved in 20 mL of acetonitrile. The resulting solution was refluxed in an oil bath at 110C for 8 hours. After the completion of the reaction, the reaction solution was cooled down to room temperature, and precipitates were filtered and recovered. The precipitates were washed with acetonitrile and dried under reduced pressure. The resulting crude crystals were suspended in a mixed solution of 10 mL of water and 10 mL of methanol. Then, about 15 mL of a saturated sodium hydrogencarbonate solution was added thereto, and the mixture was sonicated for 3 minutes using an ultrasonic washing machine. Precipitates were filtered and recovered from the resulting mixture, sufficiently washed with water, and dried under reduced pressure, to obtain 737 mg (corresponding to 2.19 mmol) of 2-(4'-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyrimidine (Fig. 1-8, Step 2).
		646 mg (corresponding to 3.0 mmol) of 2-bromo-4'-hydroxyacetophenone and 668 mg (corresponding to 3.0 mmol) of <strong>[1445-39-2]2-amino-5-iodopyrimidine</strong> were dissolved in 20 mL of acetonitrile. The resulting solution was refluxed in an oil bath at 110C for 8 hours. After the completion of the reaction, the reaction solution was cooled down to room temperature, and precipitates were filtered and recovered. The precipitates were washed with acetonitrile and dried under reduced pressure. The resulting crude crystals were suspended in a mixed solution of 10 mL of water and 10 mL of methanol. Then, about 15 mL of a saturated sodium hydrogencarbonate solution was added thereto, and the mixture was sonicated for 3 minutes using an ultrasonic washing machine. Precipitates were filtered and recovered from the resulting mixture, sufficiently washed with water, and dried under reduced pressure, to obtain 737 mg (corresponding to 2.19 mmol) of 2-(4'-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyrimidine (Fig. 4, Step 2). The NMR measurement results of the resulting 2-(4'-hydroxyphanyl)-6-iodoimidazo[1,2-a]pyrimidine (internal standard: dimethylformamide) are shown below. NMR apparatus employed: JNM-ECP-500 (manufactured by Japan Electron Optics Laboratory Co., Ltd. (JEOL)) 1H-NMR (solvent: dimethylformamide-d7, resonance frequency: 500 MHz): delta 9.80 (br. s, 1H), 9.35 (d, J = 2.3 Hz, 1H), 8.60 (d, J = 2.3 Hz, 1H), 8.23 (s, 1H), 7.94-7.90 (m, 2H), 6.98-6.94 (m, 2H). 13C-NMR (solvent: dimethylformamide-d7, resonance frequency: 125 MHz): delta 158.87, 154.00, 147.18, 146.77, 139.07, 127.68, 124.50, 115.85, 106.10, 73.46.
	With sodium hydrogencarbonate; In methanol; water; acetonitrile;	, Step 1). 646 mg (corresponding to 3.0 mmol) of 2-bromo-4'-hydroxyacetophenone and 668 mg (corresponding to 3.0 mmol) of <strong>[1445-39-2]2-amino-5-iodopyrimidine</strong> were dissolved in 20 mL of acetonitrile. The resulting solution was refluxed in an oil bath at 110C for 8 hours. After the completion of the reaction, the reaction solution was cooled down to room temperature, and precipitates were filtered and recovered. The precipitates were washed with acetonitrile and dried under reduced pressure. The resulting crude crystals were suspended in a mixed solution of 10 mL of water and 10 mL of methanol. Then, about 15 mL of a saturated sodium hydrogencarbonate solution was added thereto, and the mixture was sonicated for 3 minutes using an ultrasonic washing machine. Precipitates were filtered and recovered from the resulting mixture, sufficiently washed with water, and dried under reduced pressure, to obtain 737 mg (corresponding to 2.19 mmol) of 2-(4'-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyrimidine (

With sodium hydrogencarbonate; In methanol; water; acetonitrile;

, Step 1). 646 mg (corresponding to 3.0 mmol) of 2-bromo-4'-hydroxyacetophenone and 668 mg (corresponding to 3.0 mmol) of <strong>[1445-39-2]2-amino-5-iodopyrimidine</strong> were dissolved in 20 mL of acetonitrile. The resulting solution was refluxed in an oil bath at 110C for 8 hours. After the completion of the reaction, the reaction solution was cooled down to room temperature, and precipitates were filtered and recovered. The precipitates were washed with acetonitrile and dried under reduced pressure. The resulting crude crystals were suspended in a mixed solution of 10 mL of water and 10 mL of methanol. Then, about 15 mL of a saturated sodium hydrogencarbonate solution was added thereto, and the mixture was sonicated for 3 minutes using an ultrasonic washing machine. Precipitates were filtered and recovered from the resulting mixture, sufficiently washed with water, and dried under reduced pressure, to obtain 737 mg (corresponding to 2.19 mmol) of 2-(4'-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyrimidine (

Reference： [1]Patent: EP2019103,2009,A1 .Location in patent: Page/Page column 17
[2]Patent: EP2022792,2009,A1 .Location in patent: Page/Page column 10; 28
[3]Patent: EP2216051,2010,A1
[4]Patent: EP2218463,2010,A1

21
[ 4214-76-0 ]
[ 2491-38-5 ]
[ 956499-89-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 5-nitro-pyridin-2-ylamine; 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone In acetonitrile at 110℃; for 6h; Heating / reflux; Stage #2: With sodium hydrogencarbonate In methanol; water for 0.05h; Sonication;	I-10; 8.2 432 mg (corresponding to 2.0 mmol) of 2-bromo-4'-hydroxyacetophenone and 279 mg (corresponding to 2.0 mmol) of 2-amino-5-nitropyridine were dissolved in 20 mL of acetonitrile. The resulting solution was refluxed in an oil bath at 110°C for 6 hours. After the completion of the reaction, the reaction solution was cooled down to room temperature, and precipitates were filtered and recovered. The precipitates were washed with acetonitrile and dried under reduced pressure. The resulting crude crystals were suspended in a mixed solution of 8 mL of water and 8 mL of methanol. Then, about 8 mL of a saturated sodium hydrogencarbonate solution was added thereto, and the mixture was sonicated for 3 minutes using an ultrasonic washing machine. Precipitates were filtered and recovered from the resulting mixture, sufficiently washed with water, and dried under reduced pressure, to obtain 148 mg (corresponding to 0.580 mmol) of 2-(4'-hydroxyphenyl)-6-nitroimidazo[1,2-a]pyridine (Fig. 8, Step 2). The NMR measurement results of the resulting 2-(4'-hydroxyphenyl)-6-nitroimidazo[1,2-a]pyridine (internal standard: dimethylsulfoxide) are shown below. NMR apparatus employed: JNM-ECP-500 (manufactured by Japan Electron Optics Laboratory Co., Ltd. (JEOL)) 1H-NMR (solvent: dimethylsulfoxide-d6, resonance frequency: 500 MHz): δ 9.74-9.72 (m, 1H), 9.59 (br. s, 1H), 8.39 (s, 1H), 7.87 (dd, J = 9.9, 2.3 Hz, 1H), 7.79-7.74 (m, 2H), 7.65-7.61 (m, 1H), 6.84-6.80 (m, 2H). 13C-NMR (solvent: dimethylsulfoxide-d6, resonance frequency: 125 MHz): δ 158.47, 148.51, 145.25, 136.63, 127.93, 127.81, 124.06, 118.92, 116.09, 115.92, 110.37.
	With sodium hydrogencarbonate In methanol; water; acetonitrile	1 (ExaropleI-10) Synthesis of 2-(4'-hydroxyphenyl)-6-nitroimidazo[1,2-a]pyridine , Step 1). 432 mg (corresponding to 2.0 mmol) of 2-bromo-4'-hydroxyacetophenone and 279 mg (corresponding to 2.0 mmol) of 2-amino-5-nitropyridine were dissolved in 20 mL of acetonitrile. The resulting solution was refluxed in an oil bath at 110°C for 6 hours. After the completion of the reaction, the reaction solution was cooled down to room temperature, and precipitates were filtered and recovered. The precipitates were washed with acetonitrile and dried under reduced pressure. The resulting crude crystals were suspended in a mixed solution of 8 mL of water and 8 mL of methanol. Then, about 8 mL of a saturated sodium hydrogencarbonate solution was added thereto, and the mixture was sonicated for 3 minutes using an ultrasonic washing machine. Precipitates were filtered and recovered from the resulting mixture, sufficiently washed with water, and dried under reduced pressure, to obtain 148 mg (corresponding to 0.580 mmol) of 2-(4'-hydroxyphenyl)-6-nitroimidazo[1,2-a]pyridine (

Reference： [1]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED; GENERAL ELECTRIC CO - EP2022792, 2009, A1 Location in patent: Page/Page column 12-13; 29
[2]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; GENERAL ELECTRIC CO; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - EP2216051, 2010, A1

22
[ 2491-38-5 ]
[ 10167-97-2 ]
[ 887576-96-7 ]

Yield	Reaction Conditions	Operation in experiment
		, Step 4). 2.15 g (corresponding to 10.0 mmol) of 2-bromo-4'-hydroxyacetophenone and 1.25 g (corresponding to 10.0 mmol) of <strong>[10167-97-2]2-amino-5-methoxypyridine</strong> were dissolved in 50 mL of acetonitrile. The resulting solution was refluxed in an oil bath at 90°C for 3.5 hours. After the completion of the reaction, the reaction solution was cooled down to room temperature, and precipitates were filtered and recovered. The precipitates were washed with acetonitrile and dried under reduced pressure. The resulting crude crystals were suspended in a mixed solution of 40 mL of water and 40mL of methanol. Then, about 20 mL of a saturated sodium hydrogencarbonate solution was added thereto, and the mixture was sonicated for 5 minutes using a ultrasonic washing machine. Precipitates were filtered and recovered from the resulting mixture, sufficiently washed with water, and dried under reduced pressure, to obtain 1.96 g (corresponding to 8.16 mmol) of 2-(4'-hydroxyphenyl)-6-methoxyimidazo[1,2-a]pyridine ( 2.15 g (corresponding to 10.0 mmol) of 2-bromo-4'-hydroxyacetophenone and 1.25 g (corresponding to 10.0 mmol) of 2-amino-5'-methoxypyridine were dissolved in 50 mL of acetonitrile. The resulting solution was refluxed in an oil bath at 90°C for 3.5 hours. After the completion of the reaction, the reaction solution was cooled down to room temperature, and precipitates were filtered and recovered. The recovered precipitates were washed with acetonitrile, and dried under reduced pressure to obtain crude crystals. The resulting crude crystals were suspended in a mixed solution of 40 mL of water and 40mL of methanol. The suspension was supplemented with about 20 mL of a saturated sodium hydrogencarbonate solution, and sonicated for 5 minutes by an ultrasonic washing machine. The precipitates were filtered and recovered from the resulting mixture, washed with water, and dried under reduced pressure, to obtain 1.96 g (corresponding to 8.16 mmol) of 2-(4'-hydroxyphenyl)-6-'methoxyimidazo[1,2-a]pyridine (Fig. 1, Step 5).
		645 mg (corresponding to 3.00 mmol) of 2-bromo-4'-hydroxyacetophenone and 372 mg (corresponding to 3.00 mmol) of <strong>[10167-97-2]2-amino-5-methoxypyridine</strong> were dissolved in 20 mL of acetonitrile. The resulting solution was heated under reflux in an oil bath at 90°C for 2 hours. After the completion of the reaction, the reaction solution was cooled down to room temperature, and precipitates were filtered and recovered. The precipitates were washed with acetonitrile and dried under reduced pressure to obtain crude crystals. The resulting crude crystals were suspended in a mixed solution of 4.0 mL of water and 4.0 mL of methanol. Then, about 2.0 mL of a saturated sodium hydrogencarbonate solution was added thereto, and the mixture was sonicated for 5 minutes using an ultrasonic washing machine. Precipitates were filtered and recovered from the resulting mixture, sufficiently washed with water, and dried under reduced pressure, to obtain 512 mg (corresponding to 2.17 mmol) of 2-(4'-hydroxypheny)-6-methoxyimidazo[1,2-a]pyridine (Fig. 9, Step 5).

Reference： [1]Patent: EP2042501,2009,A1 .Location in patent: Page/Page column 8; 15; 24
[2]Patent: EP2213672,2010,A1 .Location in patent: Page/Page column 16; 27

23
[ 2491-38-5 ]
[ 1147550-11-5 ]
[ 56430-88-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	Stage #1: ammonium thiocyanate With montmorillonite K₁₀ clay In acetone at 20℃; for 0.666667h; Stage #2: 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone at 20℃; for 0.00833333h; Neat (no solvent); Grinding;	General procedure for the preparation of K10-montmorillonite clay supported ammonium thiocyanate; General procedure for the synthesis of α-oxo thiocyanates by using K10-montmorillonite clay supported ammonium thiocyanate under catalyst and solvent free conditions In a round bottomed 500 ml flask equipped with stir bar and containing 100 ml acetone, was added 7.6 g of ammonium thiocyanate salt and stirred at room temperature until the complete dissolution of salt. To this clear solution, 10 g of montmorillonite K10 clay was added in portions over 10 min with stirring. After complete addition, the formation of reddish suspension was observed which was vigorously stirred for another 30 min at room temperature. Then the suspension is placed in a rotary vacuum evaporator and the solvent was removed under reduced pressure. The dry solid crust adhering to the walls of the flask was flaked off with a spatula, and solvent evaporation was resumed. After complete drying, yielded, about 17.6 g of clay supported ammonium thiocyanate as a light red free flowing powder which shows no loss of reactivity after standing in an open powder box for one week.; Phenacyl bromide (1 mmol) and K10-montmorillonite clay supported ammonium thiocyanate (3 mmol) were taken in mortar, mixed with spatula, and ground with pestle for stipulated time (see Table 3). After complete conversion as indicated by TLC, the solid reaction mixture was directly loaded on silica gel column by avoiding aqueous work up-extraction step. Later elution with ethyl acetate-hexane (9:1-3:1) solvent system and evaporation of solvents in rotary vacuum evaporator afforded pure phenacyl thiocyanate (99%). Same procedure as discussed above was followed to prepare all thiocyanate compounds shown in this work. All compounds prepared were characterized by IR, Mass, and NMR spectroscopy.
	In dichloromethane at 20℃;

Reference： [1]Location in patent: experimental part Meshram; Thakur, Pramod B.; Madhu Babu; Bangade, Vikas M. [Tetrahedron Letters, 2012, vol. 53, # 14, p. 1780 - 1785]
[2]Location in patent: experimental part Bhalerao, Dinesh S.; Akamanchi, Krishnacharya G. [Synthetic Communications, 2010, vol. 40, # 6, p. 799 - 807]

24
[ 98198-48-2 ]
[ 2491-38-5 ]
[ 1147549-07-2 ]

Yield	Reaction Conditions	Operation in experiment
		2.00 g (corresponding to 9.28 mmol) of 2-bromo-4'-hydroxyacetophenone and 1.91 g (corresponding to 10.2 mmol) of <strong>[98198-48-2]2-amino-5-bromo-4-methylpyridine</strong> were dissolved in 40 mL of acetonitrile. The resulting solution was heated under reflux in an oil bath at 110C for 3 hours. After the completion of the reaction, the reaction solution was cooled down to room temperature, and precipitates were filtered and recovered. The precipitates were washed with acetonitrile and dried under reduced pressure. The resulting crude crystals were suspended in a mixed solution of 10 mL of water and 10 mL of methanol. Then, about 50 mL of a saturated sodium hydrogencarbonate solution was added thereto, and the mixture was sonicated for 10 minutes using an ultrasonic washing machine. Precipitates were filtered and recovered from the resulting mixture, sufficiently washed with water, and dried under reduced pressure, to obtain 2.67 g (corresponding to 8.81 mmol) of 6-bromo-2-[4'-hydroxyphenyl]-7-methylimidazo[1,2-a]pyridine (Fig. 9, Step 2).

Reference： [1]Patent: EP2213671,2010,A1 .Location in patent: Page/Page column 13; 26

25
[ 2491-38-5 ]
[ 2752-65-0 ]
4-(2-bromoacetyl)phenyl gambogate [ No CAS ]

Reference： [1]Molecules,2012,vol. 17,p. 6249 - 6268

26
[ 2491-38-5 ]
[ 487-70-7 ]
[ 446-72-0 ]

Yield	Reaction Conditions	Operation in experiment
75%		General procedure: To prepare catalyst, 0.21 g of thiamine hydrochloride (0.6 mmol) was dissolved in 0.64 mL of water and added 2.4 mLof 95% ethanol (water : 95% ethanol = ~1:4). The solution was cooled in an ice bath, then added 0.40 mL of 3 M NaOH(1.2 mmol) dropwise with stirring in a manner such that thetemperature remained below 20 C. Intense yellow coloured solution changed to pale yellow solution of thiamine (thiazolium ion)/N-heterocyclic carbene (Scheme 1).47 In a 25-mL round bottom flask, a mixture of phenacylbromide 1 (2.5 mmol, 0.5 g in case of 1a) and thiamine (0.6 mmol, 25 mol %) in ethanol (4 mL) was stirred at room temperature for 15 min. Then, salicylaldehyde 2 (2.5 mmol, 0.26 mL in case of 2a) was added slowly and the mixture was stirred at room temperature until the reaction was completed (as monitored by TLC) (Table 3) . The reaction mixture was then poured into 20 mL of distilled water and extracted with ethyl acetate (3 × 10 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The resulting product isoflavone 3 was further purified either by recrystallizationor by column chromatography (Ethyl acetate:Hexane, 1:4v/v). All compounds were characterized by their mp and 1HNMR, 13CNMR and mass spectral data.

Reference： [1]Bulletin of the Korean Chemical Society,2013,vol. 34,p. 1070 - 1076

27
[ 2491-38-5 ]
[ 95-01-2 ]
[ 486-66-8 ]

Yield	Reaction Conditions	Operation in experiment
82%		General procedure: To prepare catalyst, 0.21 g of thiamine hydrochloride (0.6 mmol) was dissolved in 0.64 mL of water and added 2.4 mLof 95% ethanol (water : 95% ethanol = ~1:4). The solution was cooled in an ice bath, then added 0.40 mL of 3 M NaOH(1.2 mmol) dropwise with stirring in a manner such that thetemperature remained below 20 C. Intense yellow coloured solution changed to pale yellow solution of thiamine (thiazolium ion)/N-heterocyclic carbene (Scheme 1).47 In a 25-mL round bottom flask, a mixture of phenacylbromide 1 (2.5 mmol, 0.5 g in case of 1a) and thiamine (0.6 mmol, 25 mol %) in ethanol (4 mL) was stirred at room temperature for 15 min. Then, salicylaldehyde 2 (2.5 mmol, 0.26 mL in case of 2a) was added slowly and the mixture was stirred at room temperature until the reaction was completed (as monitored by TLC) (Table 3) . The reaction mixture was then poured into 20 mL of distilled water and extracted with ethyl acetate (3 × 10 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The resulting product isoflavone 3 was further purified either by recrystallizationor by column chromatography (Ethyl acetate:Hexane, 1:4v/v). All compounds were characterized by their mp and 1HNMR, 13CNMR and mass spectral data.

Reference： [1]Bulletin of the Korean Chemical Society,2013,vol. 34,p. 1070 - 1076

28
[ 2491-38-5 ]
[ 387-46-2 ]
[ 148356-24-5 ]

Yield	Reaction Conditions	Operation in experiment
82%		General procedure: To prepare catalyst, 0.21 g of thiamine hydrochloride (0.6 mmol) was dissolved in 0.64 mL of water and added 2.4 mLof 95% ethanol (water : 95% ethanol = ~1:4). The solution was cooled in an ice bath, then added 0.40 mL of 3 M NaOH(1.2 mmol) dropwise with stirring in a manner such that thetemperature remained below 20 C. Intense yellow coloured solution changed to pale yellow solution of thiamine (thiazolium ion)/N-heterocyclic carbene (Scheme 1).47 In a 25-mL round bottom flask, a mixture of phenacylbromide 1 (2.5 mmol, 0.5 g in case of 1a) and thiamine (0.6 mmol, 25 mol %) in ethanol (4 mL) was stirred at room temperature for 15 min. Then, salicylaldehyde 2 (2.5 mmol, 0.26 mL in case of 2a) was added slowly and the mixture was stirred at room temperature until the reaction was completed (as monitored by TLC) (Table 3) . The reaction mixture was then poured into 20 mL of distilled water and extracted with ethyl acetate (3 × 10 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The resulting product isoflavone 3 was further purified either by recrystallizationor by column chromatography (Ethyl acetate:Hexane, 1:4v/v). All compounds were characterized by their mp and 1HNMR, 13CNMR and mass spectral data.

Reference： [1]Bulletin of the Korean Chemical Society,2013,vol. 34,p. 1070 - 1076

29
[ 2491-38-5 ]
[ 20816-46-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With silver(I) acetate In N,N-dimethyl-formamide at 50℃; for 3h; Inert atmosphere; Darkness;	General procedure for acetoxylation of alkyl halides with AgOAc. General procedure: To a suspension of AgOAc (0.25 mmol) in MeCN or DMF (2 mL) was added the alkylhalide (0.25 mmol) dissolved in 1 mL of the corresponding solvent. The reaction mixture was stirred at the temperature indicated on table 1 until starting material was consumed. After that, a saturated solution of NH4Cl (20 mL) was added and the crude mixture was extracted three times with EtOAc (3 x 15 mL). When necessary, the product was purifiedby column chromatography (hexane/EtOAc).

Reference： [1]Nolla-Saltiel, Roberto; Carrillo-Arcos, Ulises Alonso; Porcel, Susana [Synthesis, 2014, vol. 46, # 2, p. 165 - 169]

30
[ 2491-38-5 ]
[ 4619-20-9 ]
[ 79-19-6 ]
[ 1476801-87-2 ]

Yield	Reaction Conditions	Operation in experiment
78%		General procedure: Absolute EtOH (20 mL), ketoacid (10 mmol), 0.2 g activated KSF, and thiosemicarbazide(10 mmol) were added to a 100-ml round-bottom flask equipped withcondenser and magnetic stir bar. The reaction mixture was refluxed for the requiredreaction time (about 7 h). The progress of reaction was monitored by thin-layer chromatography(TLC) (EtOAc-petroleum ether 2:1). After completion of the reaction,phenacyl bromide (10 mmol) was added and refluxed for the required reaction time(about 2 h). The progress of the reaction was monitored by TLC (EtOAc-petroleumether 1:2). The catalyst was removed by filtration. The reaction solution was cooledto rt. The product was isolated by filtration and purified by washing with EtOH.

Reference： [1]Synthetic Communications,2014,vol. 44,p. 245 - 250

31
[ 2491-38-5 ]
[ 3984-34-7 ]
[ 79-19-6 ]
[ 1476801-89-4 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: 4-(4-chlorophenyl)-4-oxobutanoic acid; thiosemicarbazide With montmorillonite KSF In ethanol for 0.7h; Reflux; Stage #2: 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone In ethanol for 0.2h; Reflux; regioselective reaction;	General Procedure for the Synthesis of 2-(Thiazol-2-yl)-4,5-dihydropyridazin-3(2H)-one General procedure: Absolute EtOH (20 mL), ketoacid (10 mmol), 0.2 g activated KSF, and thiosemicarbazide(10 mmol) were added to a 100-ml round-bottom flask equipped withcondenser and magnetic stir bar. The reaction mixture was refluxed for the requiredreaction time (about 7 h). The progress of reaction was monitored by thin-layer chromatography(TLC) (EtOAc-petroleum ether 2:1). After completion of the reaction,phenacyl bromide (10 mmol) was added and refluxed for the required reaction time(about 2 h). The progress of the reaction was monitored by TLC (EtOAc-petroleumether 1:2). The catalyst was removed by filtration. The reaction solution was cooledto rt. The product was isolated by filtration and purified by washing with EtOH.

Reference： [1]Mahmoodi, Nosrat O.; Safari, Niloufar; Sharifzadeh, Bahman [Synthetic Communications, 2014, vol. 44, # 2, p. 245 - 250]

32
[ 2491-38-5 ]
[ 6340-79-0 ]
[ 79-19-6 ]
[ 1476801-90-7 ]

Yield	Reaction Conditions	Operation in experiment
82%		General procedure: Absolute EtOH (20 mL), ketoacid (10 mmol), 0.2 g activated KSF, and thiosemicarbazide(10 mmol) were added to a 100-ml round-bottom flask equipped withcondenser and magnetic stir bar. The reaction mixture was refluxed for the requiredreaction time (about 7 h). The progress of reaction was monitored by thin-layer chromatography(TLC) (EtOAc-petroleum ether 2:1). After completion of the reaction,phenacyl bromide (10 mmol) was added and refluxed for the required reaction time(about 2 h). The progress of the reaction was monitored by TLC (EtOAc-petroleumether 1:2). The catalyst was removed by filtration. The reaction solution was cooledto rt. The product was isolated by filtration and purified by washing with EtOH.

Reference： [1]Synthetic Communications,2014,vol. 44,p. 245 - 250

33
[ 2491-38-5 ]
[ 3696-23-9 ]
[ 825661-01-6 ]

Yield	Reaction Conditions	Operation in experiment
62%	In ethanol at 80℃; for 0.5h; Microwave irradiation;	4 General procedure: A solution of 150 mg (0.64 mmol) 2-bromo-1-(4-chlorophenyl)-ethanone (B, Scheme 2 ) and 126 mg (0.64 mmol) 1-(benzo[d][1,3]dioxol-5-yl)thiourea (E, Scheme 2 ) in 2 ml ethanol was heated to 80 °C for 30 min under microwave irradiation. The precipitated white hydrobromide salt was collected, washed with H2O and cold ethanol, yield: 182 mg (69%).

Reference： [1]Rödl, Carmen B.; Vogt, Dominik; Kretschmer, Simon B.M.; Ihlefeld, Katja; Barzen, Sebastian; Brüggerhoff, Astrid; Achenbach, Janosch; Proschak, Ewgenij; Steinhilber, Dieter; Stark, Holger; Hofmann, Bettina [European Journal of Medicinal Chemistry, 2014, vol. 84, p. 302 - 311]

34
[ 2491-38-5 ]
[ 459-05-2 ]
[ 1622931-26-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	In ethanol at 80℃; for 0.5h; Microwave irradiation;	4 General procedure: A solution of 150 mg (0.64 mmol) 2-bromo-1-(4-chlorophenyl)-ethanone (B, Scheme 2 ) and 126 mg (0.64 mmol) 1-(benzo[d][1,3]dioxol-5-yl)thiourea (E, Scheme 2 ) in 2 ml ethanol was heated to 80 °C for 30 min under microwave irradiation. The precipitated white hydrobromide salt was collected, washed with H2O and cold ethanol, yield: 182 mg (69%).

35
[ 14222-60-7 ]
[ 2491-38-5 ]
[ 1046045-54-8 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 6572 - 6582

36
[ 2491-38-5 ]
[ 17356-08-0 ]
[ 57634-55-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water; for 0.333333h;Reflux;	General procedure: 2-amino-4-aryl thiazole derivatives were prepared19-21using different substituted phenacyl bromides by refluxing with excess thiourea in presence of conc. HClfor about 20 min. After the completion of reaction, thereaction mixture was cooled to room temperature; thepale yellow solid thus separated was filtered, washedwith chloroform, dried and recrystallized from ethanolto obtain 2-amino-4-aryl thiazole derivatives.

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 3068 - 3087
[2]Journal of Chemical Sciences,2014,vol. 126,p. 1913 - 1921
[3]Journal of the Chinese Chemical Society,2017,vol. 64,p. 1408 - 1416

37
[ 461-88-1 ]
[ 2491-38-5 ]
4-(7-aminoimidazo[1,2-a]pyridin-2-yl)phenol hydrobromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	In acetone; at 65℃;Inert atmosphere; Sealed tube;	Example 3a) 4-(7-Aminoimidazo[1,2-a]pyridin-2-yl)phenol hydrobromideIn a 5 mL microwave vial, <strong>[461-88-1]pyridine-2,4-diamine</strong> (500 mg, 4.58 mmol) and 2-bromo-l-(4- hydroxyphenyl)ethanone (1.03 g, 4.81 mmol) were combined with acetone (8.0 mL) to give an off-white suspension. The vial was flushed with argon and closed. The reaction mixture was stirred at 65 C ( oil bath temperature) overnight. The off-white suspension was filtered and washed with acetone. The resulting off-white solid was dried under high vacuum overnight to afford the title compound (363 mg, 18 % yield) as an off-white solid. MS m/z: 226.1 [M+H]+

Reference： [1]Patent: WO2015/44095,2015,A1 .Location in patent: Page/Page column 13

38
[ 2491-38-5 ]
[ 42017-89-0 ]
2-(4-hydroxyphenyl)-2-oxoethyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In tetrahydrofuran; at 20℃; for 4h;	General procedure: CDI (10.0 mmol) was dissolved in N,N-dimethylformamide (DMF) (20 mL) and to this solution a solution of the carboxylic acids 14a and d (10.0 mmol) in DMF (2 mL) was added dropwise. Subsequently, the reaction mixture was stirred at room temperature for 1 h. Then, H2S was bubbled gently through the reaction mixture for 2 h. Sulfuric acid (0.5 M, 40 mL) was added and the mixture was extracted with ethyl acetate. The organic layer was dried with magnesium sulfate (MgSO4), filtered, and concentrated to yield 16a ,d, 14a, d, 16a, and d (2.0 mmol). They were dissolved in THF (10 mL), anhydrous K2CO3 (4.0 mmol) and 2-bromo-4-hydroxyacetophenone 11 (2.0 mmol) were added, and the mixture was stirred for 4 h at room temperature. Dilute HCl was added, and the mixture was extracted with ethyl acetate, washed with brine, dried over MgSO4, filtered, and concentrated, and the residue was purified by chromatography to afford target compounds 17a, d, 18a, and d.

Reference： [1]Chemical and Pharmaceutical Bulletin,2015,vol. 63,p. 628 - 635

39
[ 2491-38-5 ]
[ 25812-30-0 ]
2-(4-hydroxyphenyl)-2-oxoethyl 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In tetrahydrofuran; at 20℃; for 4h;	General procedure: CDI (10.0 mmol) was dissolved in N,N-dimethylformamide (DMF) (20 mL) and to this solution a solution of the carboxylic acids 14a and d (10.0 mmol) in DMF (2 mL) was added dropwise. Subsequently, the reaction mixture was stirred at room temperature for 1 h. Then, H2S was bubbled gently through the reaction mixture for 2 h. Sulfuric acid (0.5 M, 40 mL) was added and the mixture was extracted with ethyl acetate. The organic layer was dried with magnesium sulfate (MgSO4), filtered, and concentrated to yield 16a ,d, 14a, d, 16a, and d (2.0 mmol). They were dissolved in THF (10 mL), anhydrous K2CO3 (4.0 mmol) and 2-bromo-4-hydroxyacetophenone 11 (2.0 mmol) were added, and the mixture was stirred for 4 h at room temperature. Dilute HCl was added, and the mixture was extracted with ethyl acetate, washed with brine, dried over MgSO4, filtered, and concentrated, and the residue was purified by chromatography to afford target compounds 17a, d, 18a, and d. 2-(4-Hydroxyphenyl)-2-oxoethyl-5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate (17a): Yield 83%, mp 105.6-108.3 C. 1H-NMR (400 MHz, CDCl3) delta: 1.32 (6H, s), 1.81-1.85 (4H, m),2.18 (3H, s), 2.30 (3H, s), 3.94-3.97 (2H, m), 5.23 (2H, s), 5.62(1H, s), 6.63-6.66 (2H, m), 6.85-6.87 (2H, m), 6.98-7.00 (1H,d, J=7.6 Hz), 7.80-7.82 (2H, m). ESI-MS m/z: 385 [M+H]+.
3.21 g		A mixture of <strong>[25812-30-0]gemfibrozil</strong> (2.50 g, 10.0 mmol)And K2CO3 (1.37 g, 10.0 mmol)Was added to tetrahydrofuran (30 mL)After stirring at room temperature for 0.5 h,To the stirred solution was added alpha-bromo-p-hydroxyacetophenone (2.15 g, 10.0 mmol)In tetrahydrofuran (10 mL),Continue stirring for 12 h.Spin out the solvent,Dilute hydrochloric acid acidification,Ethyl acetate (25 mL x 3) was added,Organic phase with water,Dried over anhydrous sodium sulfate,The filtrate was separated and purified by silica gel column chromatography.Intermediate2- (4-hydroxyphenyl) -2-oxo-ethyl-5- (2,5-dimethylphenoxy) -2,2-dimethyl-pentanoic acid 3.21g,

Reference： [1]Molecular Diversity,2018,p. 1 - 15
[2]Chemical and Pharmaceutical Bulletin,2015,vol. 63,p. 628 - 635
[3]Patent: CN106478452,2017,A .Location in patent: Paragraph 0056; 0057

40
[ 2491-38-5 ]
[ 4254-67-5 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 9713 - 9721
[2]Journal of Organic Chemistry,2015,vol. 80,p. 9713 - 9721

41
[ 2491-38-5 ]
[ 37904-72-6 ]
[ 79-40-3 ]
[ 39696-20-3 ]
C₂₂H₂₂N₄S₂ [ No CAS ]
C₂₀H₁₇N₃OS₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;Reflux;	A one-step combinatorial approach for synthesis of the bithiazoles was performed in ethanol The mixture of three possible products was purified by means of flash chromatography or preparative HPLC.

Reference： [1]Patent: WO2016/1422,2016,A1 .Location in patent: Page/Page column 25

42
[ 2491-38-5 ]
[ 100-39-0 ]
[ 4254-67-5 ]

Yield	Reaction Conditions	Operation in experiment
43%	With silver carbonate; In tetrahydrofuran; at 0 - 20℃; for 16h;	Step 1: Preparation of l-(4-(benzyloxy)phenyl)-2-bromoethanone [00170] To a solution of 2-bromo- 1 -(4-hydroxyphenyl)ethanone (2 g, 9.3 mmol) in tetrahydrofuran (70 mL) was added silver carbonate (5.128 g, 18.6 mmol) and the reaction mixture was cooled to 0 C. Benzyl bromide (1.32 m L, 11.16 mmol) was added drop wise and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was filtered through celite, the filtrate was diluted with ethyl acetate (200 mL) and washed with water (60 mL x 2). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The crude was purified by column chromatography using 6% ethyl acetate in hexane to afford title l-(4-(benzyloxy)phenyl)-2-bromoethanone (1.22 g, 43% yield) as a white solid. Calculated M+H: 306.17; Found M+H: 306.

Reference： [1]Patent: WO2016/49165,2016,A1 .Location in patent: Paragraph 00170

43
[ 15761-39-4 ]
[ 2491-38-5 ]
1-(tert-butyl) 2-(2-(4-hydroxyphenyl)-2-oxoethyl) (S)-pyrrolidine-1,2-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 5h;	5.1.1.14 1-(tert-Butyl) 2-(2-(4-hydroxyphenyl)-2-oxoethyl) (S)-pyrrolidine-1,2-dicarboxylate (10a) 2-Bromo-4-hydroxyacetophenone 9a (1.00g, 4.65mmol) and N-Boc-l-proline (1.10g, 5.12mmol) in Acetonitrile (50mL) put into the flask. Diisopropylethylamine (1.44mL, 5.58mmol) was added dropwise to the mixture and was stirred at room temperature for 5h. The mixture was then poured in 1N aq HCl solution and extracted with CH2Cl2. The organic layer dried over magnesium sulfate, and then was purified by the column chromatography (n-hexane/ethyl acetate). The residue 10a was obtained as white solid (1.20g, 74%). 1H NMR (DMSO-d6, δ=2.5ppm, 400MHz): 10.49 (s, 1H), 7.86-7.85 (d, 2H), 6.88-6.86 (t, 2H), 5.53-5.32 (m, 2H), 4.32-4.29 (m, 1H), 3.11 (m, 2H), 2.29-2.14 (m, 2H), 1.90-1.85 (m, 2H), 1.36 (app br s, 9H). 13C NMR (DMSO-d6, δ=39.52ppm, 100MHz): 190.5, 172.3, 162.7, 153.0, 130.4, 125.4, 115.4, 78.9, 66.1, 58.6, 46.2, 30.4, 27.9, 23.1. HRMS (ESI) m/z: Anal. calcd. for [M+Na]+ C18H23NNaO6: 372.1418; found 372.1419.
74%	With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 5h;	21 Preparation of (S)-1-tert-butyl 2-(2-(4-hydroxyphenyl)-2-oxoethyl)pyrrolidine-1,2-dicarboxylate 2-Bromo-4-hydroxyacetophenone (1.00 g, 4.65 mmol) And N-Boc-L-proline (1.10 g, 5.12 mmol) Was dissolved in acetonitrile (50 mL) Diisopropylethylamine (1.44 mL, 5.58 mmol) was added portionwise, And the mixture was stirred at room temperature for 5 hours. The reaction mixture was diluted with 1 N aqueous hydrochloric acid solution and extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then concentrated in vacuo. The residue was purified by silica gel flash column chromatography using hexane: ethyl acetate as mobile phase to give the desired compound (1.20 g, 74% yield) as a white solid.
74%	With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 5h;

Reference： [1]You, Youngsu; Kim, Hee Sun; Bae, Il Hak; Lee, Seung Gi; Jee, Min Hyeok; Keum, Gyochang; Jang, Sung Key; Kim, B. Moon [European Journal of Medicinal Chemistry, 2017, vol. 125, p. 87 - 100]
[2]Current Patent Assignee: POHANG UNIVERSITY OF SCIENCE AND TECHNOLOGY; SEOUL NATIONAL UNIVERSITY - KR2017/31307, 2017, A Location in patent: Paragraph 0262-0264
[3]You, Youngsu; Kim, Hee Sun; Park, Jung Woo; Keum, Gyochang; Jang, Sung Key; Kim, B. Moon [RSC Advances, 2018, vol. 8, # 55, p. 31803 - 31821]

44
[ 2491-38-5 ]
[ 7659-07-6 ]
2-(4-fluorophenyl)-6-(4-hydroxyphenyl)imidazo[2,1-b]-1,3,4-oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44.2%	In ethanol; for 0.00694444h;Microwave irradiation; Green chemistry;	1) added to the drying in the crucible 0.01mol abromo-p-hydroxyacetophenone, 0.01mol 2-amino-5-(pfluorophenyl)-1,3,4-oxadiazole is dissolved in anhydrous ethanol, get mixed solution A1, to a crucible of the reaction liquid is placed in the microwave oven, power modulation high fire files 700W, opening microwave oven radiation 25 seconds after the closing, of the crucible is taken out of the glass rod for stirring cooling, every 5 to detect reaction TLC (developing agent to volume ratio is: dichloromethane: methanol =10:1 mixture); 2) if the crucible is ethanol volatilizes in adding ethanol, to TLC detection reaction is complete, add water to the reaction solution of 15 ml, then the saturated NaOH solution for pH value adjusted to 7-8, to get mixed solution B1; 3) the mixture solution B1off the solvent, the crude product obtained after water washing, filtering, drying and recrystallized with absolute ethanol, to obtain 2 - (4-fluoro phenyl) - 6 - (4-hydroxy-phenyl)-imidazo [2,1-b] - 1, 3, 4-oxadiazole, yield 44.2%,

Reference： [1]Patent: CN105418636,2016,A .Location in patent: Paragraph 0052; 0053; 0054; 0055; 0056

45
[ 2491-38-5 ]
[ 25812-30-0 ]
[ 57260-73-8 ]
C₃₃H₄₀N₂O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.64 g		<strong>[25812-30-0]Gemfibrozil</strong> lg,Dicyclohexylcarbodiimide 1.07 g,1-Boc ethylenediamine 0.64 g,Dichloromethane 60ml placed in a single mouth bottle 100ml,The reaction was carried out at room temperature for 4 hours. The residue was recrystallized from ethanol and evaporated to dryness to give 1.44 g of a white solid, 50 ml of a single-necked flask, 20 ml of methylene chloride and 4 ml of trifluoroacetic acid,After 1 hour, lmol / L potassium carbonate aqueous solution to adjust pH to alkaline,The organic layer was dried,The solvent was evaporated,Ethanol recrystallization,Obtained as a white solid. 94 g,50ml single-mouth bottle,2-Bromo-1- (4-hydroxyphenyl) ethanone (1.37 g)Potassium carbonate 3.5 g,TLC was used to monitor the reaction end point,Column chromatography gave 1.64 g of the title compound

Reference： [1]Patent: CN103087009,2016,B .Location in patent: Paragraph 0091; 0092

46
[ 2491-38-5 ]
[ 41859-67-0 ]
C₂₇H₂₆ClNO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.93 g	With potassium carbonate; In tetrahydrofuran; at 20℃; for 3.5h;	<strong>[41859-67-0]Bezafibrate</strong> lg,0.6 g of 2-bromo-1- (4-hydroxyphenyl) ethanone,0.84 g of potassium carbonate, 50 ml of tetrahydrofuran,The reaction was carried out at room temperature for 3.5 hours, and the filtrate was evaporated to dryness to afford the desired compound (0.93 g)

Reference： [1]Patent: CN103087009,2016,B .Location in patent: Paragraph 0105; 0106

47
[ 2491-38-5 ]
[ 41859-67-0 ]
C₂₇H₂₆ClNO₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.7 g		<strong>[41859-67-0]Bezafibrate</strong> 1g,0.49 g of N, N-carbonyldiimidazole (CDI)N, N-dimethylformamide (DMF)Stirring at room temperature 4h, access to hydrogen sulfide gas,After 20 minutes, the solvent was evaporated to dryness, 20 ml of ethyl acetate was added,Cold dilute aqueous solution of hydrochloric acid 20ml,The organic layer was dried, concentrated and evaporated to dryness to give a yellow solid.2-bromo-1- (4-hydroxyphenyl) ethanone,Potassium carbonate 0.84 g,The yellow crude product obtained above,Tetrahydrofuran (50 ml)Room temperature reaction,3 hours,The filtrate was evaporated to dryness to afford 0.7 g of the title compound

Reference： [1]Patent: CN103087009,2016,B .Location in patent: Paragraph 0109; 0110

48
[ 461-88-1 ]
[ 2491-38-5 ]
4-(7-aminoimidazo[1,2-a]pyridin-2-yl)phenol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 7350 - 7370

49
[ 5346-38-3 ]
[ 2491-38-5 ]
[ 764623-45-2 ]

Reference： [1]Archiv der Pharmazie,2018,vol. 351

50
[ 2491-38-5 ]
[ 4919-43-1 ]
C₁₉H₁₅NO₄ [ No CAS ]

Reference： [1]RSC Advances,2018,vol. 8,p. 15009 - 15020

51
[ 2491-38-5 ]
[ 39809-25-1 ]
3-(4-hydroxy-3-(hydroxymethyl)butyl)-6-(4-hydroxyphenyl)-3,5-dihydro-9H-imidazo[1,2-a]purin-9-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%		General procedure: To a suspension of penciclovir (6) or hydroxybutylguanine (7)(0.2 g, 0.8 mmol or 0.9 mmol, respectively) in dry dimethylformamide(16 mL), sodium hydride (60% suspension in mineral oil, 1.2 eq.) wasadded and the reaction stirred at room temperature (21 C) for 1.5 h.Bromoketone (8) (1.3 eq.) was then added and the reaction stirred for6 h. Aqueous ammonia (25% solution 5 mL) was added to quench thereaction, which was concentrated under reduced pressure and the residualoil purified by flash column chromatography using gradientelution (CH2Cl2-MeOH). The obtained products were recrystallisedfrom a mixture of CH2Cl2 and MeOH.

Reference： [1]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 1023 - 1033

52
[ 2491-38-5 ]
[ 1612-76-6 ]
4-(2-phenylimidazo[2,1-b][1,3,4]oxadiazol-5-yl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70.4%	In ethanol for 0.416667h; Microwave irradiation;	The microwave method General procedure: The 2-Amino-5-aryl-1,3,4-oxadiazole (0.01 mol), α-bromoacetophenones derivatives (0.01 mol) and catalyst were treated by a microwave system for about the appropriate time. The microwave-accelerated reaction system was operated at 200 W. The progress of the reaction was monitored by TLC using dichloromethane/methanol (10:1) as eluent. After completion of the reaction, the solution pH was adjusted to 7-8. The crude product thus obtained was filtered, and recrystallized from N,N-Dimethylformamide to get the compounds (1a-1v).

Reference： [1]Liu, Yuting; Dang, Yang; Yin, Dawei; Yang, Lan; Zou, Qian [Research on Chemical Intermediates, 2019, vol. 45, # 10, p. 4907 - 4926]

53
[ 2491-38-5 ]
[ 7659-07-6 ]
4-[2-(4-fluorophenyl)-6-piperazin-1-ylmethylimidazo[2,1-b][1,3,4]oxadiazol-5-yl]phenol [ No CAS ]

Reference： [1]Research on Chemical Intermediates,2019,vol. 45,p. 4907 - 4926

54
[ 2491-38-5 ]
[ 7659-07-6 ]
4-[2-(4-fluorophenyl)imidazo[2,1-b][1,3,4]oxadiazol-5-yl]phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72.3%	In ethanol; for 0.333333h;Microwave irradiation;	General procedure: The 2-Amino-5-aryl-1,3,4-oxadiazole (0.01 mol), α-bromoacetophenones derivatives (0.01 mol) and catalyst were treated by a microwave system for about the appropriate time. The microwave-accelerated reaction system was operated at 200 W. The progress of the reaction was monitored by TLC using dichloromethane/methanol (10:1) as eluent. After completion of the reaction, the solution pH was adjusted to 7-8. The crude product thus obtained was filtered, and recrystallized from N,N-Dimethylformamide to get the compounds (1a-1v).

Reference： [1]Research on Chemical Intermediates,2019,vol. 45,p. 4907 - 4926

55
[ 4144-22-3 ]
[ 2491-38-5 ]
2-(tert-butyl)-8-hydroxy-3a,9b-dihydro-1H-benzo[e]isoindole-1,3,5(2H,4H)-trione [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 6270 - 6274

56
[ 2491-38-5 ]
[ 89226-13-1 ]
tert-butyl N-[[4-(4-hydroxyphenyl)thiazol-2-yl]methyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	In ethanol; at 20℃; for 12h;	To a solution of 2-bromo-1-(4-hydroxyphenyl)ethan-1-one (1.5 g, 6.97 mmol) in EtOH (30 mL) was added <strong>[89226-13-1]tert-butyl (2-amino-2-thioxoethyl)carbamate</strong> (1.3 g, 6.97 mmol) at room temperature. The mixture was stirred 12 h then concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 30-40% EtOAc in petroleum ether affording an off white solid (900 mg, 42%). M/z 307.1 (M+H)+.

Reference： [1]Patent: EP3628672,2020,A1 .Location in patent: Paragraph 0272-0274

57
3-(2-((4-methoxyphenyl)amino)ethyl)-4-phenyl-1H-1,2,4-triazole-5(4H)-thione [ No CAS ]
[ 2491-38-5 ]
1-(4-hydroxyphenyl)-2-((5-(2-((4-methoxyphenyl)amino)ethyl)-4-phenyl-4H-1,2,4-triazol-3-yl)thio)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium carbonate In acetone at 40℃; for 3h;	Method C. General procedure: To triazolethione 8 (0.49 g, 1.5 mmol) dissolved in acetone (15 mL), K2CO3 (1 g, 7.2 mmol) and corresponding halocarbonyl compound (2 mmol) were added. The reaction mixture was stirred at 40 °C for 3 h. Afterwards water (20 mL) was added, the precipitate formed was isolated by filtration, and recrystallized from propan-2-ol.

Reference： [1]Jonuškienė, Ilona; Kantminienė, Kristina; Klevinskas, Arnas; Mickevičius, Vytautas; Petrikaitė, Vilma; Tumosienė, Ingrida [Molecules, 2020, vol. 25, # 13]

58
[ 2491-38-5 ]
6-(benzo[d][1,3]dioxol-5-ylmethyl)-5-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one [ No CAS ]
6-(benzo[d][1,3]dioxol-5-ylmethyl)-2-((2-(4-hydroxyphenyl)-2-oxoethyl) thio)-5-methylpyrimidin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;	4.4 General synthesis of 5-alkyl-6-(benzo[d][1,3]dioxol-5-alkyl)-2-mercapto-pyrimidin-4(3H)-ones (5a-5w) General procedure: K2CO3 (0.3g, 2.2mmol) and R2Br (2.2mmol) were added to a solution of (benzo[d][1,3]dioxol-5-alkyl)-5-alkyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-ones 11a-11d (2mmol) in anhydrous DMF (8mL). The mixture was stirred at room temperature for 8-24h. After TLC revealed the disappearance of the starting material, the reaction mixture was filtered. The suspension was then diluted with cold water (150mL) and extracted with EtOAc (3×50mL). The combined organic extract was washed with brine (3×50mL), dried with Na2SO4, and evaporated to furnish crude product, which was purified by flash chromatography or by crystallization to give the pure target compounds 5a-5w.
	Stage #1: 6-(benzo[d][1,3]dioxol-5-ylmethyl)-5-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone In N,N-dimethyl-formamide at 20℃; for 2h;	2 General procedure: Combine 6-(1,3-benzodioxy-5-methyl)-2-mercapto-5-ethyl-3H-pyrimidin-4-one) (S-DABOs reactant) (3mmol) and K2CO3( 3.6mmol) was placed in a round-bottomed flask, added 5ml of anhydrous dimethylformamide (DMF), stirred at room temperature for 1h, added brominated side chain reactant (3.3mmol), stirred at room temperature for 2h, when TLC (Thin-layer chromatographic analysis) The reaction is stopped after tracking to the disappearance of the raw material point. Pour the reaction solution into 100ml ice water, back-extract three times with EA (ethanol) (50ml×3), combine the organic layers, wash three times with water (50ml×3), and then wash three times with saturated brine (50ml×3). Finally, it was dried with anhydrous Na2SO4 to obtain the crude product of the target compound, which was purified by column chromatography or recrystallized with acetone/petroleum ether, ethyl acetate/petroleum ether or methanol/chloroform system to obtain 6-(1,3-benzodioxy- 5-(methyl)yl)-substituted uracil derivative compounds 1a to 1w are pure products. The purification steps are: column chromatography purification or recrystallization. The solvent is the volume ratio in the column chromatography purification operation.Recrystallization operation: dissolve the compound sample with solvent A, then add solvent B until the resulting solution is turbid and stop adding solvent B. After standing still, a large amount of precipitate is deposited.

Reference： [1]Cui, Yi-Man; He, Yan-Ping; Huang, Si-Ming; Li, Sui-Yuan; Li, Xiao-Li; Li, Yi-Ming; Luo, Rong-Hua; Ni, Dong-Xuan; Tang, E.; Xiao, Wei-Lie; Yang, Liu-Meng; Zhang, Hong-Bin; Zhang, Rui-Han; Zhang, Xing-Jie; Zheng, Yong-Tang; Zheng, Yu-Gui [Bioorganic Chemistry, 2020, vol. 102]
[2]Current Patent Assignee: YUNNAN UNIVERSITY; CHINESE ACADEMY OF SCIENCES - CN111303136, 2020, A Location in patent: Paragraph 0099-0107

59
[ 2491-38-5 ]
[ 142197-65-7 ]
O-ethyl-Se-(p-hydroxyphenacyl)-N-phenylisoselenocarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 5h; Darkness; chemoselective reaction;	3.3.2. General Procedure for the Preparation of Se-Phenacyl Isoselenocarbamates 16-21 General procedure: To a solution of O-ethyl-N-phenylselenocarbamate 14 (110 mg, 0.48 mmol) or O-ethyl-N-(1-naphthyl)selenocarbamate 15 (134 mg, 0.48 mmol) in DMF (5 mL) was added thecorresponding phenacyl halide 4-6 (1.0 equiv.) and DIPEA (84 L, 0.48 mmol, 1.0 equiv.)The resulting mixture was stirred at rt and in the dark for 5 h. Then, it was concentrated todryness and the residue was purified by column chromatography (hexane 2:1 hexane-EtOAc) to give Se-phenacyl isoselenocarbamates 16-21.

Reference： [1]Begines, Paloma; Fernández-Bolaños, José G.; López, Óscar; Lagunes, Irene; Martos, Sergio; Maya, Inés; Padrón, José M. [Molecules, 2022, vol. 27, # 4]

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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

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 2491-38-5 ]

Quality Control of [ 2491-38-5 ]

Related Doc. of [ 2491-38-5 ]

Product Details of [ 2491-38-5 ]

Calculated chemistry of [ 2491-38-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 2491-38-5 ]

Application In Synthesis of [ 2491-38-5 ]

[ 2491-38-5 ] Synthesis Path-Upstream 1~9

[ 2491-38-5 ] Synthesis Path-Downstream 1~59

Related Functional Groups of [ 2491-38-5 ]

Aryls

Bromides

Ketones

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 2491-38-5 ]