143468-96-6

Basic information

• Product Name: 2-Carbethoxy-3-(2-thienyl)propanoic acid
• Synonyms: 2-Carbethoxy-3-(2-Thienyl)-Propionic Acid;(2-Thienylmethyl)propanedioic acid monoethyl ester;2-Carbethoxy-3-(2-thienyl)propanoic acid;2-(2-THIENYLMETHYL) PROPANEDIOIC ACID MONOETHYL ESTER (SB201999);ethyl 2-carboxy-3-(2-thienyl)propionate;2-(2-ThienylMethyl)propanedioic Acid 1-Ethyl Ester;2-(Ethoxycarbonyl)-3-(thien-2-yl)propanoic acid;3-ethoxy-3-oxo-2-(thiophen-2-ylmethyl)propanoic acid
• CAS NO: 143468-96-6
• Molecular Formula: C₁₀H₁₂O₄S
• Molecular Weight: 228.26
• EINECS: 415-680-8
• Product Categories: Aromatics;Heterocycles;Intermediates
• Mol File: 143468-96-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 361.9 °C at 760 mmHg
• Flash Point: 172.7 °C
• Appearance: /
• Density: 1.295
• Vapor Pressure: 7.16E-06mmHg at 25°C
• Refractive Index: 1.548
• Storage Temp.: 2-8°C(protect from light)
• PKA: 2.67±0.34(Predicted)
• CAS DataBase Reference: 2-Carbethoxy-3-(2-thienyl)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Carbethoxy-3-(2-thienyl)propanoic acid(143468-96-6)
• EPA Substance Registry System: 2-Carbethoxy-3-(2-thienyl)propanoic acid(143468-96-6)

Safety Data

• Hazard Codes: Xi
• Statements: 38-41-43
• Safety Statements: 24-26-37/39
• Hazardous Substances Data: 143468-96-6(Hazardous Substances Data)

Usage

Description

2-Carbethoxy-3-(2-thienyl)propanoic acid is an organic compound with the molecular formula C9H10O4S. It is a derivative of propanoic acid, featuring a carbethoxy group at the 2nd position and a 2-thienyl group at the 3rd position. 2-Carbethoxy-3-(2-thienyl)propanoic acid is known for its potential applications in the pharmaceutical industry, particularly in the development of angiotensin II receptor antagonists.

Uses

Used in Pharmaceutical Industry:
2-Carbethoxy-3-(2-thienyl)propanoic acid is used as a key intermediate in the synthesis of angiotensin II receptor antagonists. These antagonists are important for the treatment of hypertension and heart failure, as they block the action of angiotensin II, a potent vasoconstrictor, thereby reducing blood pressure and improving cardiovascular function.
Additionally, 2-(2-Thienylmethyl)propanedioic Acid 1-Ethyl Ester, a related compound, is also used in the preparation of angiotensin II receptor antagonists. This highlights the versatility and importance of these chemical structures in the development of life-saving medications.

InChI:InChI=1/C10H12O4S/c1-2-14-10(13)8(9(11)12)6-7-4-3-5-15-7/h3-5,8H,2,6H2,1H3,(H,11,12)

Upstream product

• 45438-73-1 2-thenyl bromide 
• 105-53-3 diethyl malonate 
• 30313-06-5 diethyl 2-(thiophen-2-ylmethylene)malonate 
• 98-03-3 thiophene-2-carbaldehyde 
• 26420-00-8 diethyl (thien-2-ylmethyl)malonate 

Downstream Products

• 64107-46-6 3-(thien-2-yl)propionic acid ethyl ester 
• 133485-84-4 (E)-3-[2-n-butyl-1-{(2,3-dichlorophenyl)methyl}-1H-imidazol-5-yl]-2-(thien-2-yl)methyl-2-propenoic acid 
• 133485-77-5 SKF 108834 
• 1104528-98-4 (E)-α-[[2-butyl-1-[(4-carboxyphenyl)methyl]-1H-imidazol-5-yl]methylene]-2-thiophene propanoic acid acetate 
• 133040-01-4 eprosartan 
• 133486-13-2 ethyl (αE)-α-[[2-n-butyl-1-[[4-(methoxycarbonyl)phenyl]methyl]-1H-imidazol-5-yl]methylene-2-thiophene]propionate 
• 133485-98-0 2-[2-Butyl-5-((E)-2-carboxy-3-thiophen-2-yl-propenyl)-imidazol-1-ylmethyl]-benzoic acid 

Relevant articles and documents

Preparation of mono-substituted malonic acid half oxyesters (SMAHOs)

The use of mono-substituted malonic acid half oxyesters (SMAHOs) has been hampered by the sporadic references describing their preparation. An evaluation of different approaches has been achieved, allowing to define the best strategies to introduce diversity on both the malonic position and the ester function. A classical alkylation step of a malonate by an alkyl halide followed by a monosaponification gave access to reagents bearing different substituents at the malonic position, including functionalized derivatives. On the other hand, the development of a monoesterification step of a substituted malonic acid derivative proved to be the best entry for diversity at the ester function, rather than the use of an intermediate Meldrum acid. Both these transformations are characterized by their simplicity and efficiency, allowing a straightforward access to SMAHOs from cheap starting materials.

IMPROVED PROCESS FOR MANUFACTURING ANHYDROUS (E)-3-[2-BUTYL-1- {(4-CARBOXYPHENYL) METHYL}-1H-IMIDAZOLE-5-YL]-(THIOPHEN-2- YLMETHYL)PROP-2-ENOIC ACID METHANE SULFONATE

The present invention relates to a simple efficient and cost effective process for commercial manufacture of (E)-3-[2-Butyl-1-{(4-carboxyphenyl) methyl}-1H-imidazole-5-yl]- 2-(thiophen-2-ylmethyl)prop-2-enoic acid and its conversion to substantially pure

Potent Nonpeptide Angiotensin II Receptor Antagonists. 2. (1-Carboxybenzyl)imidazole-5-acrylic Acids

The further evolution of the imidazole-5-acrylic acid series of nonpeptide angiotensin II receptor antagonists is detailed (for Part 1, see: J.Med.Chem. 1992, 35, 3858).Modifications of the N-benzyl ring substitution were undertaken in an effort to mimic the Tyr4 residue of angiotensin II.Introduction of a p-carboxylic acid on the N-benzyl ring resulted in the discovery of compounds with nanomolar affinity for the receptor and good oral activity.SAR studies of these potent antagonists revealed that the thienyl ring, the (E)-acrylic acid, and the imidazole ring in addition to the two acid groups were important for high potency.Also, overlay comparisons of the parent diacid with both angiotensin II and a representative biphenylyltetrazole nonpeptide angiotensin II receptor antagonist are presented.The parent diacid analog, SKF 108566 or (E)-3--2-propenoic acid, is currently in clinical development for the treatment of hypertension.