6-Amino-m-cresol Chemical Properties

Melting point:

160-162 °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,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

9.87±0.10(Predicted)

color 

Beige to Dark Beige

Water Solubility 

soluble

BRN 

386144

Stability:

Hygroscopic

LogP

0.900 (est)

CAS DataBase Reference

2835-98-5(CAS DataBase Reference)

NIST Chemistry Reference

Phenol, 2-amino-5-methyl-(2835-98-5)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36-37/39

WGK Germany 

1

RTECS 

SJ6090000

Hazard Note 

Irritant

HS Code 

29222900

MSDS

• Language:English Provider:2-Amino-5-methylphenol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

6-Amino-m-cresol Usage And Synthesis

Chemical Properties

Beige to brown crystal powder

Uses

2-Amino-5-methylphenol was used in the synthesis of tridentate Schiff base ligand and novel non-metallocene catalysts with phenoxy-imine ligands.

General Description

2-Amino-5-methylphenol reacts with bovine hemoglobin to form 2-amino-4,4α-dihydro-4α-7-dimethyl-3H-phenoxazine-3-one, which inhibits the proliferation of Poliovirus in Vero cells. It is converted to dihydrophenoxazinone by purified human hemoglobin.

Synthesis

The general procedure for the synthesis of 6-aminoresorcinol from 6-nitroresorcinol was as follows: 5-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 at low temperature, followed by replacement of air in the system with hydrogen (supplied via a balloon). After the reaction was stirred for 5 h under hydrogen atmosphere, the reaction mixture was filtered through a diatomaceous earth pad and the diatomaceous earth pad was washed with methanol (100 mL). Finally, the combined filtrates were concentrated under reduced pressure to afford 2-amino-5-methylphenol (801 mg, 100% yield).

Purification Methods

Crystallise it from H2O, 50% EtOH, or toluene. [Beilstein

References

[1] Patent: US2006/211603, 2006, A1. Location in patent: Page/Page column 69
[2] Advanced Synthesis and Catalysis, 2013, vol. 355, # 5, p. 907 - 911
[3] Journal of Heterocyclic Chemistry, 1982, vol. 19, # 6, p. 1545 - 1547
[4] Synthesis, 2001, # 1, p. 81 - 84
[5] Justus Liebigs Annalen der Chemie, 1902, vol. 322, p. 18

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