N-Benzylethylenediamine

N-Benzylethylenediamine Property

Boiling point:

162 °C/20 mmHg (lit.)

Density 

1 g/mL at 25 °C (lit.)

refractive index 

1.5400

Flash point:

95°C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

clear liquid

pka

9.27±0.10(Predicted)

color 

Colorless to Light yellow

Water Solubility 

negligible

BRN 

907505

InChI

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

InChIKey

ACYBVNYNIZTUIL-UHFFFAOYSA-N

SMILES

C(NCC1=CC=CC=C1)CN

CAS DataBase Reference

4152-09-4(CAS DataBase Reference)

NIST Chemistry Reference

1,2-Ethanediamine, n-(phenylmethyl)-(4152-09-4)

EPA Substance Registry System

1,2-Ethanediamine, N-(phenylmethyl)- (4152-09-4)

Safety

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

23-26-36/37/39-45

RIDADR 

2735

WGK Germany 

3

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29335990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P363Wash contaminated clothing before reuse.

P405Store locked up.

N-Benzylethylenediamine Chemical Properties,Usage,Production

Chemical Properties

Colorless liquid

Uses

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.

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.

Flammability and Explosibility

Not classified

Synthesis

Ethylenediamine (3.4 mL, 51 mmol) with anhydrous methanol (38 mL) was added to a 100 mL aubergine vial. Benzaldehyde (1000 μL, 9.8 mmol) was dissolved in anhydrous methanol (5 mL) and slowly added dropwise into the above aiguille. After the dropwise addition, the reaction mixture was continued to be stirred for 30 min. Subsequently, sodium borohydride (0.371 g, 11 mmol) was added in batches under ice bath conditions. The reaction mixture was cooled and stirred overnight. Upon completion of the reaction, the solvent was removed by evaporation and dichloromethane (50 mL) was added to dissolve the residue. The organic phase was washed twice with saturated saline (5 mL) and the organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated to give N-benzylethylenediamine (colorless liquid, 938 mg, 64% yield).

References

[1] Tetrahedron Letters, 2006, vol. 47, # 35, p. 6277 - 6280
[2] Russian Chemical Bulletin, 2010, vol. 59, # 6, p. 1254 - 1266
[3] Patent: CN107721925, 2018, A. Location in patent: Paragraph 0104; 0105
[4] European Journal of Medicinal Chemistry, 2012, vol. 57, p. 417 - 428
[5] Journal of Medicinal Chemistry, 1990, vol. 33, # 2, p. 781 - 789