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462292

Sigma-Aldrich

N-Benzylethylenediamine

97%

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Synonym(s):
2-Benzylaminoethylamine
Linear Formula:
C6H5CH2NHCH2CH2NH2
CAS Number:
Molecular Weight:
150.22
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

refractive index

n20/D 1.54 (lit.)

bp

162 °C/20 mmHg (lit.)

density

1 g/mL at 25 °C (lit.)

SMILES string

NCCNCc1ccccc1

InChI

1S/C9H14N2/c10-6-7-11-8-9-4-2-1-3-5-9/h1-5,11H,6-8,10H2

InChI key

ACYBVNYNIZTUIL-UHFFFAOYSA-N

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General description

N-Benzylethylenediamine participates in the one-pot synthesis of N,N,N′-trisubstituted guanidines. It undergoes condensation with dibenzoylmethane (1,3-diphenyl-1,3-propanedione) in stoichiometric ratio 1:1 to afford the corresponding Schiff monobase.

Application

N-Benzylethylenediamine may be used for the synthesis of N-benzyl-N,N′,N′-tris(tert-butyloxycarbonylmethyl)ethylenediamine and 3-benzyl-2-(phenyl-2-sulfonate)-2-imidazoline tetraheptylammonium salt.

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Skin Corr. 1B

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Nickel (II) Complexes of Dibenzoylmethane and N-benzylethylenediamine, and Their Schiff Monobase.
Gutierrez JA, et al.
Journal of Coordination Chemistry, 28(3-4), 305-312 (1993)
Application of a-chloroaldoxime O-methanesulfonates to one-pot synthesis of N, N', N?-substituted guanidines via Tiemann rearrangement.
Yamamoto Y, et al.
Tetrahedron Letters, 50(42), 5813-5815 (2009)
A new method for the synthesis of tri-tert-butyl diethylenetriaminepentaacetic acid and its derivatives.
Achilefu S, et al.
The Journal of Organic Chemistry, 65(5), 1562-1565 (2000)
Anthony Weatherwax et al.
Organic letters, 7(16), 3461-3463 (2005-07-29)
Trans-disubstituted beta-lactams show increasing utility and prominence in numerous pharmaceutical applications, making their asymmetric synthesis an attractive goal for chemists. We introduce an anionic, nucleophilic catalyst system that provides an efficient, diastereoselective route to trans-disubstituted beta-lactams, a complement to our

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