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144894

Sigma-Aldrich

4-Amino-3-methylphenol

97%

Synonym(s):

2-Amino-5-hydroxytoluene, 4-Amino-m-cresol, 4-Hydroxy-2-methylaniline

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About This Item

Linear Formula:
H2NC6H3(CH3)OH
CAS Number:
2835-99-6
Molecular Weight:
123.15
Beilstein:
2078803
EC Number:
220-621-2
MDL number:
MFCD00007871
UNSPSC Code:
12352100
PubChem Substance ID:
24848689
NACRES:
NA.22

Quality Level

200

Assay

97%

form

solid

mp

176-179 °C (lit.)

SMILES string

Cc1cc(O)ccc1N

InChI

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

InChI key

QGNGOGOOPUYKMC-UHFFFAOYSA-N

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General description

4-Amino-3-methylphenol is a metabolite of 3-methyl-4-nitrophenol. It is a major metabolite of carcinogenic o-toluidine and causes DNA damage in the presence of Cu(II).

Application

4-Amino-3-methylphenol was used in synthesis of a new type of tweezer-molecule in which a strongly preferred binding conformation is generated by convergent, intramolecular hydrogen bonding.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H317,H410

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Skin Sens. 1A

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Y Ohkuma et al.
Archives of biochemistry and biophysics, 372(1), 97-106 (1999-11-24)
Mechanisms of DNA damage by metabolites of carcinogenic o-toluidine in the presence of metals were investigated by the DNA sequencing technique using (32)P-labeled human DNA fragments. 4-Amino-3-methylphenol, a major metabolite, caused DNA damage in the presence of Cu(II). Predominant cleavage
Robert A Kanaly et al.
Journal of agricultural and food chemistry, 53(16), 6426-6431 (2005-08-04)
Biotransformation of the environmental pollutant 3-methyl-4-nitrophenol (MNP), a newly characterized estrogenic chemical, and the primary breakdown product of the heavily used insecticide fenitrothion was investigated using a common soil fungus. In 96 h, daily culture sacrifice, extraction, and analysis showed
Howard M Colquhoun et al.
Faraday discussions, 143, 205-220 (2009-01-01)
A novel type of tweezer molecule containing electron-rich 2-pyrenyloxy arms has been designed to exploit intramolecular hydrogen bonding in stabilising a preferred conformation for supramolecular complexation to complementary sequences in aromatic copolyimides. This tweezer-conformation is demonstrated by single-crystal X-ray analyses
Emel Ermiş et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 243, 118761-118761 (2020-08-28)
Eight new azomethine compounds (3a-3h) containing thiophene and aminophenol functionality were synthesized in excellent yields by using conventional heating and microwave assisted synthesis methods. The structures of newly synthesized compounds were characterized by spectroscopic techniques such as UV-Vis, FTIR, 1H

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