ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Thiophene compounds 2-AMINO-4-PHENYL-THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER

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

Product Name2-AMINO-4-PHENYL-THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER
CAS4815-36-5
MFC13H13NO2S
MW247.31
EINECS
MOL File4815-36-5.mol

Chemical Properties

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)
InChI	1S/C13H13NO2S/c1-2-16-13(15)11-10(8-17-12(11)14)9-6-4-3-5-7-9/h3-8H,2,14H2,1H3
InChIKey	WYTHTMKMOSPACP-UHFFFAOYSA-N
SMILES	CCOC(=O)c1c(N)scc1-c2ccccc2
CAS DataBase Reference	4815-36-5(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36/37/39
WGK Germany	3
HazardClass	IRRITANT
HS Code	29349990
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Usage And Synthesis

Chemical Properties

Yellow solid

Uses

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

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.

Synthesis

2-Butenoic acid, 2-cyano-3-phenyl-, ethyl ester, (2Z)-

17277-47-3

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

4815-36-5

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

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

Chemical Properties

Safety Information

Usage And Synthesis

Preparation Products And Raw materials

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