2-AMINO-4-PHENYL-THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER

2-AMINO-4-PHENYL-THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER Property

Melting point:

92-97 °C

Boiling point:

391.0±42.0 °C(Predicted)

Density 

1.231

storage temp. 

2-8°C(protect from light)

solubility 

DMF: 30 mg/ml; DMSO: 30 mg/ml; DMSO:PBS (pH 7.2) (1:10): 0.1 mg/ml; Ethanol: 20 mg/ml

form 

A crystalline solid

pka

-0.14±0.10(Predicted)

CAS DataBase Reference

4815-36-5(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29349990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

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

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

2-AMINO-4-PHENYL-THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER Chemical Properties,Usage,Production

Chemical Properties

Yellow solid

Uses

Ethyl 2-Amino-4-phenylthiophene-3-carboxylate is used in the design and synthesis of thieno[2,3-d]pyrimidine analogs which exhibits antiproliferative activity against human cancer cells such as liver, pancreatic and colorectal cancer.

Uses

2-Amino-4-phenyl-thiophene-3-carboxylic acid ethyl ester is a synthetic intermediate useful for pharmaceutical synthesis.

Synthesis

Ethyl 2-cyano-3-phenylbut-2-enoate (513.25 g, 2.3 mol) was slowly added to a vigorously stirred ethanol (500 mL) suspension of sulfur powder (76 g, 2.3 mol) at room temperature. Subsequently, diethylamine (200 mL) was added in batches over a period of 20 min, and the temperature was raised to 62 °C during the reaction. Upon completion of the reaction, the mixture was cooled to 36 °C, then heated to 50 °C and stirred continuously for 1 h at this temperature. After stopping stirring, unreacted sulfur was removed by decantation and the hot solution was cooled to room temperature. The resulting orange solid product, ethyl 2-amino-4-phenylthiophene-3-carboxylate (195 g) was collected by filtration and washed with a small amount of cold ethanol and finally dried under vacuum. The resulting product was used for subsequent experiments without further purification.

References

[1] Synthetic Communications, 2007, vol. 37, # 23, p. 4273 - 4279
[2] Patent: WO2012/131379, 2012, A1. Location in patent: Page/Page column 19
[3] Patent: US2014/206703, 2014, A1. Location in patent: Paragraph 0033; 0084; 0085