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2-Amino-4-chloro-benzenemethanol

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2-Amino-4-chloro-benzenemethanol Basic information
Product Name:2-Amino-4-chloro-benzenemethanol
Synonyms:(2-AMino-4-chloro-phenyl)-Methanol;2-Amino-4-chlorobenzyl alcohol;Benzenemethanol, 2-amino-4-chloro-;2-Amino-4-chlorobenzyl alcohol 98%;2-amino-4-chlorobenzenemethylol;2-Amino-4-chloro-benzenemethanol
CAS:37585-16-3
MF:C7H8ClNO
MW:157.6
EINECS:
Product Categories:
Mol File:37585-16-3.mol
2-Amino-4-chloro-benzenemethanol Structure
2-Amino-4-chloro-benzenemethanol Chemical Properties
Melting point 138-142°C
Boiling point 324.2±27.0 °C(Predicted)
density 1.341±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
pka14.01±0.10(Predicted)
AppearanceWhite to off-white Solid
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38-43
Safety Statements 26-36/37
WGK Germany 3
MSDS Information
2-Amino-4-chloro-benzenemethanol Usage And Synthesis
Synthesis
4-CHLORO-2-NITROBENZYL ALCOHOL

22996-18-5

2-AMINO-4-CHLORO-BENZENEMETHANOL

37585-16-3

General procedure for the synthesis of (2-amino-4-chlorophenyl)methanol from 4-chloro-2-nitrobenzenemethanol: 4-chloro-2-nitrobenzenemethanol (1 g, 5.33 mmol, ALDRICH) and platinum(IV) oxide (100 mg, 0.44 mmol) were suspended in ethanol (100 mL) and hydrogenated for 1 hr at room temperature and 1300 mbar hydrogen pressure. . After completion of the reaction, the suspension was filtered, the filter cake was washed with ethanol, and the filtrates were combined and concentrated to dryness to give the crude product (2-amino-4-chlorophenyl)methanol as a light orange solid. The crude product was purified by rapid chromatography on silica gel, the eluent being a gradient of dichloromethane solution of 0 to 3% methanol. The target fraction was collected and the solvent was evaporated to dryness to give the pure product (2-amino-4-chlorophenyl)methanol (0.650 g, 77% yield) as a light orange solid. NMR hydrogen spectrum (DMSO-d6) data: δ 4.34 (d, 2H), 5.06 (t, 1H), 5.20 (s, 2H), 6.51 (dd, 1H), 6.64 (d, 1H), 7.05 (d, 1H).

References[1] Angewandte Chemie - International Edition, 2017, vol. 56, # 35, p. 10573 - 10576
[2] Angew. Chem., 2017, vol. 129, # 35, p. 10709 - 10712,4
[3] Synlett, 2017, vol. 28, # 14, p. 1724 - 1728
[4] Patent: WO2008/104754, 2008, A1. Location in patent: Page/Page column 178-179
[5] Journal of Medicinal Chemistry, 1993, vol. 36, # 22, p. 3397 - 3408
2-Amino-4-chloro-benzenemethanol Preparation Products And Raw materials
Raw materials4-Chloro-2-nitrobenzyl alcohol-->2-Amino-4-chlorobenzoic acid-->2-Amino-4-chlorobenzoic acid-->Hydrogen-->Ethanol
Preparation ProductsBenzyl 2-(hydroxymethyl)phenylcarbamate
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