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6-Amino-m-cresol

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6-Amino-m-cresol Basic information
Product Name:6-Amino-m-cresol
Synonyms:JAROCOL 2M5AP;6-amino-meta-cresol;2-AMINO-5-METHYLPHENOL 98%;6-Amino-m-methylphenol;m-Hydroxy-p-toluidine;Phenol, 2-amino-5-methyl-;6-AMINO-M- CRESOL, 4-AMINO- 3- HYDROXYTOLUENE, 2-AMINO-5- METHYLPHENOL, 2- HYDROXY-4- METHYLANILINE;6-Amino-m-cresol;2-Amino-5-methylphenol
CAS:2835-98-5
MF:C7H9NO
MW:123.15
EINECS:220-620-7
Product Categories:Amines;Aromatic Phenols;Phenoles and thiophenoles
Mol File:2835-98-5.mol
6-Amino-m-cresol Structure
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)
pka9.87±0.10(Predicted)
form Solid
color Beige to Dark Beige
Water Solubility soluble
BRN 386144
Stability:Hygroscopic
Cosmetics Ingredients FunctionsHAIR DYEING
Cosmetic Ingredient Review (CIR)6-Amino-m-cresol (2835-98-5)
InChI1S/C7H9NO/c1-5-2-3-6(8)7(9)4-5/h2-4,9H,8H2,1H3
InChIKeyHCPJEHJGFKWRFM-UHFFFAOYSA-N
SMILESCc1ccc(N)c(O)c1
LogP0.900 (est)
CAS DataBase Reference2835-98-5(CAS DataBase Reference)
NIST Chemistry ReferencePhenol, 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
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Skin Sens. 1
MSDS Information
ProviderLanguage
2-Amino-5-methylphenol English
SigmaAldrich English
ACROS English
6-Amino-m-cresol Usage And Synthesis
Chemical PropertiesBeige to brown crystal powder
Uses2-Amino-5-methylphenol was used in the synthesis of tridentate Schiff base ligand and novel non-metallocene catalysts with phenoxy-imine ligands.
General Description2-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
5-Methyl-2-nitrophenol

700-38-9

6-Amino-m-cresol

2835-98-5

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 MethodsCrystallise 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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