1-Benzyl-2,5-dihydro-1H-pyrrole Chemical Properties

Boiling point:

60 °C1 mm Hg(lit.)

Density 

0.837 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.542(lit.)

Flash point:

198 °F

storage temp. 

Sealed in dry,Store in freezer, under -20°C

pka

8.95±0.50(Predicted)

form 

Liquid

color 

Colorless to pale yellow

Sensitive 

Air Sensitive

BRN 

111101

InChIKey

LRFHKHHUKGZIGE-UHFFFAOYSA-N

CAS DataBase Reference

6913-92-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-27-36/37/39-45-20

RIDADR 

UN 3267 8/PG 2

WGK Germany 

3

HazardClass 

8

PackingGroup 

III

HS Code 

29339900

MSDS

• Language:English Provider:1-Benzyl-3-pyrroline
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1-Benzyl-2,5-dihydro-1H-pyrrole Usage And Synthesis

Uses

1-Benzyl-3-pyrroline was used in synthesis of (S)-1-benzyl-3-hydroxypyrrolidine.

Synthesis

The general procedure for the synthesis of N-benzyl-3-pyrroline from cis-1,4-dichloro-2-butene and benzylamine was as follows: the synthesis was carried out according to the literature method with the following modifications: a) cis-1,4-dichloro-2-butene (0.76 g, 5.77 mmol) was dissolved in anhydrous dichloromethane (4 ml) at 5 °C; b) benzylamine was slowly added dropwise to the above solution ( 3.75 g, 34.66 mmol) to the above solution. The reaction mixture was stirred at 5°C for 10 min and then moved to room temperature and continued stirring for 24 hrs. After completion of the reaction, the resulting white solid was collected by filtration and washed with dichloromethane. The filtrate was cooled to 0°C, 37% hydrochloric acid (0.6 ml) was added, and the white solid was collected by filtration again and washed with dichloromethane. The filtrate was concentrated to give an orange oil, which was purified by fast chromatography (silica gel as stationary phase, hexane: ethyl acetate = 1:1 as eluent) to finally obtain N-benzyl-3-pyrroline (0.76 g, 82% yield) as a yellow oil. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3) and 13C NMR (75 MHz, CDCl3): 1H NMR δ 7.38-7.21 (m, 5H), 5.78 (s, 2H), 3.80 (s, 3H), 3.81 (s, 2H), 3.48 (s, 4H); 13C NMR δ 139.67, 128.69, 128.34, 127.78, 126.96, 60.40, 59.70.

References

[1] Patent: EP1849770, 2007, A1. Location in patent: Page/Page column 14
[2] Patent: EP1849781, 2007, A1. Location in patent: Page/Page column 88
[3] Patent: EP1849772, 2007, A1. Location in patent: Page/Page column 18
[4] Synthetic Communications, 1983, vol. 13, # 13, p. 1117 - 1124
[5] Synlett, 2002, # 1, p. 167 - 169

1-Benzyl-2,5-dihydro-1H-pyrrole(6913-92-4)Related Product Information

• Benzyl acetate
• Benzyl alcohol
• Dimethylbenzylcarbinyl acetate
• Pyrrolidine
• 3-Pyrroline
• DIBENZYLTOLUENE
• Polyvinylpyrrolidone
• Benzyltrimethylammonium hydroxide
• Benzyldimethylcarbinyl butyrate
• Benzyl chloride
• Pyrrole
• N-Methyl-2-pyrrolidone
• Benzyl benzoate
• Benzoyl peroxide
• Benzyltriethylammonium chloride
• Benzyl butyrate
• Dihydromyrcenol
• N-BENZYL-2-CYANOACETAMIDE