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144916

Sigma-Aldrich

2-Amino-5-methylphenol

98%

Synonym(s):

2-Hydroxy-4-methylaniline, 4-Amino-3-hydroxytoluene, 6-Amino-m-cresol

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About This Item

Linear Formula:
H2NC6H3(CH3)OH
CAS Number:
2835-98-5
Molecular Weight:
123.15
Beilstein/REAXYS Number:
386144
EC Number:
220-620-7
MDL number:
MFCD00007693
UNSPSC Code:
12352100
PubChem Substance ID:
24848691
NACRES:
NA.22

assay

98%

form

powder

mp

159-162 °C (lit.)

SMILES string

Cc1ccc(N)c(O)c1

InChI

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

InChI key

HCPJEHJGFKWRFM-UHFFFAOYSA-N

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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.

Application

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

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Sigma-Aldrich

122513

2-Amino-3-hydroxypyridine

Akiko Iwata et al.
The Tohoku journal of experimental medicine, 200(3), 161-165 (2003-10-03)
2-Amino-4,4alpha-dihydro-4alpha-7-dimethyl-3H-phenoxazine-3-one (Phx), which was produced by the reaction of bovine hemoglobin with 2-amino-5-methylphenol, inhibited the proliferation of poliovirus in Vero cells between 0.25 microg/ml and 2 microg/ml with maximal antiviral acitivity at 1 microg/ml. These results suggest that Phx may
The investigation of novel non-metallocene catalysts with phenoxy-imine ligands for ethylene (co-) polymerization.
Zhang X, et al.
Polymer International, 62(3), 419-426 (2012)
Synthesis,structural characterization and catalytic activity study of Mn(II), Fe(III), Ni(II), Cu(II) and Zn(II) complexes of quinoxaline-2-carboxalidine-2-amino-5-methylphenol: Crystal structure of the nickel (II) complex.
Sebastian M, et al.
Polyhedron, 29(15), 3014-3020 (2010)
A Tomoda et al.
Biochimica et biophysica acta, 1117(3), 306-314 (1992-10-27)
We found that 2-amino-5-methylphenol was converted to the dihydrophenoxazinone with a reddish brown color by purified human hemoglobin, lysates of human erythrocytes, and human erythrocytes. The reddish brown compound was identified as 2-amino-4,4 alpha-dihydro-4 alpha,7-dimethyl-3H-phenoxazin-3-one by the measurement of NMR
N Sundaraganesan et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 67(2), 550-558 (2006-09-26)
The laser Raman and Fourier transform infrared spectra of 2-amino-5-methylphenol were recorded in the solid phase. The equilibrium geometry, harmonic vibrational frequencies, infrared intensities, Raman scattering activities, depolarization ratios and reduced masses were calculated by HF and density functional B3LYP
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