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2-Amino-3-methylphenol

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2-Amino-3-methylphenol Basic information
Product Name:2-Amino-3-methylphenol
Synonyms:2-AMINO-3-METHYLPHENOL;2-AMINO-3-CRESOL;2-AMINO-M-CRESOL;2-HYDROXY-6-METHYLANILINE;2-Amino-m-methylphenol;2-AMINO-3-METHLYPHENOL;2- AMINO -M-CRESOL:2- AMINO-3- METHYLPHENOL;3-Methyl-2-aminophenol
CAS:2835-97-4
MF:C7H9NO
MW:123.15
EINECS:
Product Categories:Phenol&Thiophenol&Mercaptan;Aromatic Phenols
Mol File:2835-97-4.mol
2-Amino-3-methylphenol Structure
2-Amino-3-methylphenol Chemical Properties
Melting point 149-152 °C (lit.)
Boiling point 229.26°C (rough estimate)
density 1.0877 (rough estimate)
refractive index 1.5706 (estimate)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
pka9.87±0.10(Predicted)
form powder to crystalline
color White to Brown
InChI1S/C7H9NO/c1-5-3-2-4-6(9)7(5)8/h2-4,9H,8H2,1H3
InChIKeyFEDLEBCVFZMHBP-UHFFFAOYSA-N
SMILESCc1cccc(O)c1N
CAS DataBase Reference2835-97-4(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-37/39
WGK Germany 3
HS Code 29222990
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
SigmaAldrich English
2-Amino-3-methylphenol Usage And Synthesis
Chemical PropertiesLight yellow solid
Uses2-Amino-3-methylphenol was used in the preparation of Schiff base ligands.
General Description2-Amino-3-methylphenol is an aminophenol formed by incubating isopropyl-β-D-thiogalactopyranoside-induced E. coli JS996 strain cells with various nitroaromatic compounds.
Synthesis
3-Methyl-2-nitrophenol

4920-77-8

2-Amino-3-methylphenol

2835-97-4

The general procedure for the synthesis of 2-amino-3-methylphenol from 2-nitro-3-methylphenol was as follows: 3-methyl-2-nitrophenol (1.0 g, 6.53 mmol) was dissolved in methanol (10 mL) at 23 °C, and Pd/C catalyst (10 wt%, 400 mg) was added. The reaction mixture was deoxygenated under vacuum and then hydrogenated with a hydrogen balloon. After the reaction was carried out under stirring for 5 h, the reaction mixture was filtered through a diatomaceous earth pad and the diatomaceous earth pad was washed with methanol (100 mL). The combined filtrates were concentrated under vacuum to afford the target product 2-amino-3-methylphenol (803 mg, 100% yield).

References[1] Patent: US2006/211603, 2006, A1. Location in patent: Page/Page column 68
[2] Patent: EP1346982, 2003, A1
[3] Journal of the Chemical Society, 1925, vol. 127, p. 498
[4] Chemische Berichte, 1961, vol. 94, p. 2551 - 2561
[5] Journal of Organic Chemistry, 1989, vol. 54, # 15, p. 3740 - 3744
2-Amino-3-methylphenol Preparation Products And Raw materials
Raw materials3-Methyl-2-nitrophenol-->Methanol-->Hydrogen
Preparation Productsα-Aminoorcein-->N-(2-hydroxy-6-methylphenyl)acetamide(SALTDATA: FREE)-->4-Methyl-1,3-benzoxazole-2-thiol
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