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348015

Sigma-Aldrich

2-Aminobenzylamine

98%

Synonym(s):

(2-Aminomethylphenyl)amine, 2-(Aminomethyl)aniline, 2-(Aminomethyl)benzenamine, 2-Amino-1-benzylamine, [(2-Aminophenyl)methyl]amine, o-Aminobenzylamine

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About This Item

Linear Formula:
H2NC6H4CH2NH2
CAS Number:
4403-69-4
Molecular Weight:
122.17
MDL number:
MFCD00075408
UNSPSC Code:
12352100
PubChem Substance ID:
24861542
NACRES:
NA.22

Assay

98%

form

solid

mp

58-61 °C (lit.)

SMILES string

NCc1ccccc1N

InChI

1S/C7H10N2/c8-5-6-3-1-2-4-7(6)9/h1-4H,5,8-9H2

InChI key

GVOYKJPMUUJXBS-UHFFFAOYSA-N

General description

2-Aminobenzylamine undergoes three-component cyclisation reactions with methyl 3,3,3-trifluoropyruvate, 2-aminobenzylamine and oxo compounds to afford regio- and stereoisomers of tetrahydropyrroloquinazolinones.

Application

2-Aminobenzylamine may be used:
  • in the synthesis of 1,2,3,4-tetrahydroquinazoline oxime, via condensation reaction with 2-(naphthalen-2-yl)-2-oxoacetaldehyde oxime
  • in the synthesis of alkyl 5H-1,4-benzodiazepine-3-carboxylates
  • to modify the phosphate groups on phosphoserine peptides

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

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)

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Wen-Yun Hsueh et al.
Journal of medicinal chemistry, 64(3), 1435-1453 (2021-01-26)
In this paper, we present a copper(I)-catalyzed nitrile-addition/N-arylation ring-closure cascade for the synthesis of 5,11-dihydro-6H-indolo[3,2-c]quinolin-6-ones from 2-(2-bromophenyl)-N-(2-cyanophenyl)acetamides. Using CuBr and t-BuONa in dimethylformamide (DMF) as the optimal reaction conditions, the cascade reaction gave the target products, in high yields, with
G Sirikçi et al.
Acta chimica Slovenica, 59(4), 904-911 (2013-09-26)
A novel 1,2,3,4-tetrahydroquinazoline oxime was synthesised from a condensation reaction of 2-(naphthalen-2-yl)-2-oxoacetaldehyde oxime with 2-aminobenzylamine. Subsequently, a-imine oxime complexes of this compound that formed with Co(III) and Ni(II) metal ions were obtained. All structures were characterised by spectral methods (FT-IR
Yu Shi et al.
Analytical chemistry, 80(19), 7614-7623 (2008-09-11)
A novel method is reported to modify the phosphate groups on phosphoserine peptides to the corresponding phosphoramidates, using 2-aminobenzylamine. Upon collision-induced dissociation, the modified peptides release the positively charged phosphoramidate that via gas-phase intramolecular elimination forms a cyclophosphoramidate (CyPAA) ion
Orazio A Attanasi et al.
The Journal of organic chemistry, 76(20), 8320-8328 (2011-09-13)
A novel and simple one-pot synthesis of 3-substituted 2,5,6,7-tetrahydro-1H-1,4-diazepin-2-ones from 1,2-diaza-1,3-dienes (DDs) and N-unsubstituted aliphatic 1,3-diamines is described. Here we also report a procedure to selectively obtain alkyl 5H-1,4-benzodiazepine-3-carboxylates from the DDs and 2-aminobenzylamine. Both processes occur by means of
Lukas K Filak et al.
Organometallics, 30(2), 273-283 (2011-01-22)
The synthesis of new modified indolo[3,2-c]quinoline ligands L(1)-L(8) with metal-binding sites is reported. By coordination to ruthenium- and osmium-arene moieties 16 complexes of the type [(η(6)-p-cymene)M(L)Cl]Cl (1a,b-8a,b), where M is Ru(II) or Os(II) and L is L(1)-L(8), have been prepared.
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