3-Amino-2-methylphenol Chemical Properties

Melting point:

129-130 °C(lit.)

Boiling point:

229.26°C (rough estimate)

Density 

1.0877 (rough estimate)

refractive index 

1.5380 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

pka

10.36±0.10(Predicted)

form 

Solid

color 

White to Gray to Brown

InChI

InChI=1S/C7H9NO/c1-5-6(8)3-2-4-7(5)9/h2-4,9H,8H2,1H3

InChIKey

FLROJJGKUKLCAE-UHFFFAOYSA-N

SMILES

C1(O)=CC=CC(N)=C1C

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

29222900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

3-Amino-2-methylphenol Usage And Synthesis

Chemical Properties

brown to black crystalline powder

Uses

3-Amino-2-methylphenol is used in production of (Diimido)dicarboxylic Acid, Imide, Polyamic Acid, Polyamides, Polyesters, and Polyureas.

Synthesis

The general procedure for the synthesis of 2-methyl-3-aminophenol from 2-methyl-3-nitrophenol was as follows: 2-methyl-3-nitrophenol (2.0 g, 13.1 mmol) was dissolved in methanol (50 mL) at room temperature, and 10 wt% palladium carbon catalyst (100 mg) was added. The reaction mixture was stirred under hydrogen atmosphere for 24 hours. Upon completion of the reaction, the palladium carbon catalyst was filtered through diatomaceous earth to remove the palladium carbon catalyst. The filtrate was concentrated under reduced pressure to afford the dark solid product 2-methyl-3-aminophenol (1.62 g, 99% yield). The product was analyzed by 1H NMR (CD3OD, δ=3.31 ppm, 400 MHz) showing: 6.77-6.73 (t, 1H), 6.29-6.27 (d, 1H), 6.22-6.20 (d, 1H), 2.02 (s, 3H). 13C NMR (CD3OD, δ=49.00 ppm, 100 MHz) analysis showed: 156.7,147.5,127.2,110.9,108.8,106.7,9.2. High-resolution mass spectrometry (HRMS-ESI) analysis showed that the calculated value of [M+H]+ (C7H10NO) was 124.0757 and the measured value was 124.0759.

References

[1] Patent: US5952362, 1999, A
[2] Patent: EP887346, 1998, A2
[3] European Journal of Medicinal Chemistry, 2017, vol. 125, p. 87 - 100
[4] Patent: KR2017/31307, 2017, A. Location in patent: Paragraph 0182-0184
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 5, p. 1964 - 1978

3-Amino-2-methylphenol(53222-92-7)Related Product Information

• 3-Aminophenol
• o-Cresol
• 6-Aminocaproic acid
• Glycine
• ALTRENOGEST
• 3-Ethylphenol
• p-Cresol
• 4-Aminophenol
• m-Cresol
• o-Cresolphthalein
• Acetaminophen
• 3-Aminopyridine
• Cresol
• 2-AMINO-4-METHYLPHENOL,O-AMINO-P-METHYLPHENOL,2-AMINO-4-METHYLPHENOL / 2-AMINO-P-CRESOL / 3-AMINO-4-HYDROXYTOLUENE
• 2-Aminophenol
• Tris(hydroxymethyl)aminomethane
• O-Methyl phenolic epoxy resin
• Coumarin 102