2-(TRICHLOROACETYL)PYRROLE Chemical Properties

Melting point:

72-74 °C (lit.)

Boiling point:

285℃

Density 

1.591

Flash point:

126℃

storage temp. 

2-8°C

solubility 

Chloroform, Methanol

form 

Powder

pka

14.18±0.50(Predicted)

color 

Pale gray

CAS DataBase Reference

35302-72-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-36/37//38

Safety Statements 

26-36

RIDADR 

UN 1759 8/PG III

WGK Germany 

3

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

2-(TRICHLOROACETYL)PYRROLE Usage And Synthesis

Uses

2-(Trichloroacetyl)pyrrole, is a building block used for the synthesis of more complex pharmaceutical compounds, such as Oroidin, Hymenidin and Clathrodin.

General Description

2-(Trichloroacetyl)pyrrole is a 2-substituted pyrrole. It undergoes acylation to afford 4-acyl derivatives (4-formyl to 4-hexanoyl).

Synthesis

To a stirred solution of 2,2,2-trichloroacetyl chloride (25.5 mL, 0.227 mol) in anhydrous ether (45 mL) was added pyrrole (14.3 mL, 0.206 mol) slowly and dropwise at 0°C in an ice bath. The reaction mixture was stirred continuously. After the reaction was carried out for 2 days, brine solution (300 mL) was added to the reaction solution. Subsequently, the mixture was extracted with ethyl acetate (3 x 100 mL) and water (100 mL). The organic extracts were combined, dried with anhydrous magnesium sulfate (MgSO?), and then evaporated to remove the solvent to afford the target product 2,2,2-trichloro-1-(1H-pyrrol-2-yl)ethanone as a brown solid (43.6 g, 99% yield).

References

[1] Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 897 - 905
[2] Journal of Organic Chemistry, 1993, vol. 58, # 25, p. 7245 - 7257
[3] Tetrahedron Letters, 2014, vol. 55, # 49, p. 6698 - 6702
[4] Patent: EP3248968, 2017, A1. Location in patent: Paragraph 0097
[5] Organic Letters, 2011, vol. 13, # 17, p. 4550 - 4553

2-(TRICHLOROACETYL)PYRROLE(35302-72-8)Related Product Information

• 2-(TRICHLOROACETYL)PYRROLE
• 2,2,2-TRICHLORO-1-[4-(4-CHLOROBENZOYL)-1H-PYRROL-2-YL]-1-ETHANONE
• 2,2,2-TRICHLORO-1-[4-(2,4-DICHLOROBENZOYL)-1H-PYRROL-2-YL]-1-ETHANONE
• 1-[5-(2,2,2-TRICHLOROACETYL)-1H-PYRROL-3-YL]-1-PROPANONE
• 2-TRICHLOROACETYL-1-METHYLPYRROLE
• 2-([1-METHYL-5-(2,2,2-TRICHLOROACETYL)-1H-PYRROL-3-YL]CARBONYL)BENZENECARBOXYLIC ACID
• 2,2,2-TRICHLORO-1-[4-(2-PHENYLACETYL)-1H-PYRROL-2-YL]-1-ETHANONE
• 2-(Trichloroacetyl)pyrrole-4-sulfonyl chloride
• 4-NITRO-2-(TRICHLOROACETYL)-PYRROLE
• 4-IODO-2-(TRICHLOROACETYL)PYRROLE
• 2,2,2-TRICHLORO-1-(4-[(5-METHYL-3-PHENYL-4-ISOXAZOLYL)CARBONYL]-1H-PYRROL-2-YL)-1-ETHANONE
• 2,2,2-TRICHLORO-1-[4-(2-CHLOROBENZOYL)-1H-PYRROL-2-YL]-1-ETHANONE
• 2,2,2-TRICHLORO-1-(4-[2-FLUORO-4-(TRIFLUOROMETHYL)BENZOYL]-1H-PYRROL-2-YL)-1-ETHANONE
• 2,2,2-TRICHLORO-1-(4-[4-(TRIFLUOROMETHYL)BENZOYL]-1H-PYRROL-2-YL)-1-ETHANONE
• 2,2,2-TRICHLORO-1-(4-[2-(TRIFLUOROMETHYL)BENZOYL]-1H-PYRROL-2-YL)-1-ETHANONE
• 1-[4-(2-BROMOBENZOYL)-1H-PYRROL-2-YL]-2,2,2-TRICHLORO-1-ETHANONE
• 4-[1-METHYL-5-(2,2,2-TRICHLOROACETYL)-1H-PYRROL-3-YL]-4-OXO-2-BUTENOIC ACID
• 2,2,2-TRICHLORO-1-(4-[(3-CHLORO-2-THIENYL)CARBONYL]-1H-PYRROL-2-YL)-1-ETHANONE