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3-Hydroxy-2-methylbenzoic acid

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3-Hydroxy-2-methylbenzoic acid manufacturers

3-Hydroxy-2-methylbenzoic acid Basic information
Product Name:3-Hydroxy-2-methylbenzoic acid
Synonyms:2-Methyl-3-hydroxybenzoicacid;HMBA;3-HYDROXY-O-TOLUIC ACID;3-HYDROXY-2-TOLUIC ACID;3-HYDROXY-2-METHYLBENZOIC ACID;Hydroxytoluicacid,98%;3,2-Cresotic Acid;NSC 73133
CAS:603-80-5
MF:C8H8O3
MW:152.15
EINECS:629-955-7
Product Categories:Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Pesticide Intermediate;Organic acids;Aromatics Compounds;Aromatics;Nelfinavir Mesylate;Acids and Derivatives;Alcohols and Derivatives;bc0001
Mol File:603-80-5.mol
3-Hydroxy-2-methylbenzoic acid Structure
3-Hydroxy-2-methylbenzoic acid Chemical Properties
Melting point 143-148°C
Boiling point 336.6±30.0 °C(Predicted)
density 1.304±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
solubility DMSO (Slightly), Methanol (Slightly)
form Solid
pka3.83±0.10(Predicted)
color Light Yellow
BRN 2613791
InChIInChI=1S/C8H8O3/c1-5-6(8(10)11)3-2-4-7(5)9/h2-4,9H,1H3,(H,10,11)
InChIKeyRIERSGULWXEJKL-UHFFFAOYSA-N
SMILESC(O)(=O)C1=CC=CC(O)=C1C
CAS DataBase Reference603-80-5(CAS DataBase Reference)
Safety Information
Risk Statements 36/37/38
Safety Statements 26-36
HazardClass IRRITANT
HS Code 29182900
MSDS Information
ProviderLanguage
ALFA English
3-Hydroxy-2-methylbenzoic acid Usage And Synthesis
Chemical PropertiesLight Yellow Crystalline Solid
Uses3-Hydroxy-2-methylbenzoic Acid (cas# 603-80-5) is a compound useful in organic synthesis.
Synthesis
3-Amino-2-methylbenzoic acid

52130-17-3

3-Hydroxy-2-methylbenzoic acid

603-80-5

General procedure for the synthesis of 2-methyl-3-hydroxybenzoic acid from 3-amino-2-methylbenzoic acid: to 5 mL of water containing 0.65 mL of concentrated sulfuric acid, a cold (0°C) suspension of 0.54 g (3.3 mmol) of 2-methyl-3-aminobenzoic acid was added, followed by 0.25 g (3.6 mmol) of solid sodium nitrite. After about 15 minutes of reaction, the mixture was poured into 20 mL of warm water containing 4 mL of concentrated sulfuric acid. The reaction mixture was slowly heated to 90°C and gas was observed to escape. When gas release ceased, the solution was cooled to room temperature and extracted with ethyl acetate. The organic layers were combined, washed with 0.5 N hydrochloric acid, dried and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: 5% dichloromethane solution in methanol) to give 350 mg of white solid (melting point: 137-138°C) in 69% yield.1H NMR (CDCl3) data: δ 8.18 (br.s, 1H), 7.42 (d, J = 7.7 Hz, 1H), 7.13 (t, J = 7.9 Hz, 1H) , 6.93 (d, J = 7.9 Hz, 1H), 2.46 (s, 3H). Elemental analysis (C8H8O3) results: calculated values: C, 63.15; H, 5.29; measured values: C, 63.32; H, 5.36.

References[1] Patent: US6335/459, 2002, B1. Location in patent: Page column 29
[2] Patent: US6335459, 2002, B1. Location in patent: Page column 29
[3] Tetrahedron Letters, 2000, vol. 41, # 11, p. 1741 - 1745
[4] Patent: US5952343, 1999, A
[5] Patent: US5484926, 1996, A
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