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144908

Sigma-Aldrich

2-Amino-4-methylphenol

97%

Synonyme(s) :

2-Amino-p-cresol, 2-Hydroxy-5-methylaniline, 3-Amino-4-hydroxytoluene

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About This Item

Formule linéaire :
H2NC6H3(CH3)OH
Numéro CAS:
95-84-1
Poids moléculaire :
123.15
Numéro Beilstein :
606494
Numéro CE :
202-457-3
Numéro MDL:
MFCD00007699
Code UNSPSC :
12352100
ID de substance PubChem :
24848690
Nomenclature NACRES :
NA.22

Pureté

97%

Forme

solid

Pf

133-136 °C (lit.)

Chaîne SMILES 

Cc1ccc(O)c(N)c1

InChI

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

Clé InChI

ZMXYNJXDULEQCK-UHFFFAOYSA-N

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Description générale

2-Amino-4-methylphenol is the major sensitizer in contact allergy to Disperse Yellow 3. It reacts with acetylacetone in absolute ethanol to yield 4-(2-hydroxy-5-methylphenyl)imino-2-pentanone. It was converted to dihydrophenoxazinone by purified human hemoglobin.

Application

2-Amino-4-methylphenol was used in the synthesis of novel functionalized spiropyran derivatives of 2H-1,3-benzoxazinone series.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Hongmei Peng et al.
Inorganic chemistry, 47(21), 9828-9835 (2008-10-03)
The synthesis and reactivity of a series of sodium and rare-earth metal complexes stabilized by a dianionic N-aryloxo-functionalized beta-ketoiminate ligand were presented. The reaction of acetylacetone with 1 equiv of 2-amino-4-methylphenol in absolute ethanol gave the compound 4-(2-hydroxy-5-methylphenyl)imino-2-pentanone (LH2, 1)
Antony O Bulanov et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 71(3), 1146-1152 (2008-06-14)
Six novel functionalized spiropyran's derivatives of 2H-1,3-benzoxazinone series were synthesized by introducing the substituents with chelating ability into 2H-chromene part of the 8'-formyl-7'-hydroxy-3-methyl-4-oxo-3,4-dihydro-2H-1,3-benzoxazine-2-spiro-2'-[2H]-chromene (I) by condensation with 2-aminophenol, 2-amino-4-methylphenol, 2-amino-4-nitrophenol, 2-amino-1-methylbenzimidazole, 4-amino-4H-1,2,4-triazole, N-(4-aminophenyl)acetamide. (1)H NMR, UV/vis, IR spectroscopy combined with
Z He et al.
Applied and environmental microbiology, 66(7), 3010-3015 (2000-07-06)
In spite of the variety of initial reactions, the aerobic biodegradation of aromatic compounds generally yields dihydroxy intermediates for ring cleavage. Recent investigation of the degradation of nitroaromatic compounds revealed that some nitroaromatic compounds are initially converted to 2-aminophenol rather
A Tomoda et al.
Journal of biochemistry, 110(6), 1004-1007 (1991-12-01)
2-Amino-4-methylphenol was converted to a brownish yellow material by the lysates of human erythrocytes or purified human hemoglobin. The reaction proceeded oxidatively, coupled with the oxidation of hemoglobin. The major component of the brownish yellow material produced by oxidative condensation
M Akazawa et al.
The Tohoku journal of experimental medicine, 192(4), 301-312 (2001-04-05)
When human erythrocytes were incubated with o-aminophenol at pH 7.0 at 37 degrees C for 46 hours, intracellular oxyhemoglobin was completely oxidized to methemoglobin during the initial 6 hours, and methemoglobin formed was then reduced to oxyhemoglobin during the following
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