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122831

Sigma-Aldrich

2-Aminobenzyl alcohol

98%

Synonym(s):

2-(Hydroxymethyl)aniline

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About This Item

Linear Formula:
H2NC6H4CH2OH
CAS Number:
5344-90-1
Molecular Weight:
123.15
Beilstein/REAXYS Number:
1072211
EC Number:
226-293-7
MDL number:
MFCD00007749
UNSPSC Code:
12352100
PubChem Substance ID:
24847510
NACRES:
NA.22

assay

98%

form

solid

bp

162 °C/15 mmHg (lit.)

mp

81-83 °C (lit.)

SMILES string

Nc1ccccc1CO

InChI

1S/C7H9NO/c8-7-4-2-1-3-6(7)5-9/h1-4,9H,5,8H2

InChI key

VYFOAVADNIHPTR-UHFFFAOYSA-N

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General description

2-Aminobenzyl alcohol is oxidatively cyclised with an array of ketones in dioxane at 80°C in the presence of a ruthenium catalyst and KOH to give corresponding quinolines. It undergoes oxidation catalyzed by heterotrimetallic RuMnMn species on the hydrotalcite surface in the presence of O2 to yield 2-aminobenzaldehyde.

Application

2-Aminobenzyl alcohol was used in the synthesis of ethyl 2-hydroxymethylcarbanilate.

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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Heterotrimetallic RuMnMn species on a hydrotalcite surface as highly efficient heterogeneous catalysts for liquid-phase oxidation of alcohols with molecular oxygen.
Kohki Ebitani et al.
Angewandte Chemie (International ed. in English), 44(22), 3423-3426 (2005-04-30)
Facile intramolecular nucleophilic attack by alkoxide ions on ethyl and p-nitrophenyl carbamates.
J E Hutchins et al.
Journal of the American Chemical Society, 95(11), 3786-3790 (1973-05-30)
Ruthenium-catalysed oxidative cyclisation of 2-aminobenzyl alcohol with ketones: modified Friedlaender quinoline synthesis.
Cho CS, et al.
Chemical Communications (Cambridge, England), 24, 2576-2577 (2001)
N Sundaraganesan et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 61(3), 377-385 (2004-12-08)
The Fourier transform Raman and Fourier transform infrared spectra of 2-aminobenzyl alcohol (2ABA) were recorded in the solid phase. Geometry optimizations were done with out any constraint and harmonic vibrational wave numbers and several thermodynamic parameters were calculated for the
J P Chism et al.
Chemical research in toxicology, 2(3), 150-156 (1989-05-01)
Previous results have suggested that key intermediates in the activation of 2-nitrotoluene and 2,6-dinitrotoluene are 2-aminobenzyl alcohol and 2-amino-6-nitrobenzyl alcohol, respectively. In order to determine the metabolic pathway(s) involved in the activation steps, calf thymus DNA and [14C]-2-aminobenzyl alcohol or
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