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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:
1072211
EC Number:
226-293-7
MDL number:
MFCD00007749
UNSPSC Code:
12352100
PubChem Substance ID:
24847510
NACRES:
NA.22

Quality Level

100

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 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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

122831-25G:
122831-10G:
122831-BULK:
122831-VAR:
122831-1G:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR0173
MKCQ7398
MKCN2940
MKCL8166
MKCJ9712

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Sigma-Aldrich

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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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