3-(2-Thienyl)acrylic acid

Base Information

• Chemical Name: 3-(2-Thienyl)acrylic acid
• CAS No.: 15690-25-2
• Molecular Formula: C₇H₆O₂S
• Molecular Weight: 154.189
• European Community (EC) Number: 214-402-0
• NSC Number: 4247
• UNII: INO5ATY68D
• DSSTox Substance ID: DTXSID50901215
• Nikkaji Number: J1.100.543H,J124.140K
• Wikidata: Q27280816
• ChEMBL ID: CHEMBL1771765
• Mol file: 15690-25-2.mol

Synonyms:3-(2-Thienyl)acrylic acid;1124-65-8;15690-25-2;2-Thiopheneacrylic acid;3-(Thiophen-2-yl)acrylic acid;(E)-3-(thiophen-2-yl)acrylic acid;(2E)-3-(thiophen-2-yl)prop-2-enoic acid;(2E)-3-(2-Thienyl)acrylic acid;2-Thienylacrylic acid;2-Thiopheneacrylic acid, (E)-;(E)-3-thiophen-2-ylprop-2-enoic acid;3-(Thien-2-yl)acrylic acid;(E)-2-thiopheneacrylic acid;UNII-INO5ATY68D;MFCD00005455;INO5ATY68D;2-Propenoic acid, 3-(2-thienyl)-, (E)-;CHEMBL1771765;2-Propenoic acid, 3-(2-thienyl)-, (2E)-;Acrylic acid, .beta.-2-thienyl-;2-Propenoic acid, 3-(2-thienyl)-;(E)-3-(2-Thienyl)acrylic acid;Acrylic acid, beta-2-thienyl-;(E)-3-(2-thienyl)-2-propenoic acid;3-(2-Thienyl)-2-propenoic acid;NSC 4247;EINECS 214-402-0;2-Propenoic acid,3-(2-thienyl)-;3-(thiophen-2-yl)prop-2-enoic acid;NoName_302;(2E)-3-THIEN-2-YLACRYLIC ACID;3-(2-Thienyl)acrylic acid, predominantly trans;3-(2-thienyl)-acrylic acid;trans-3-Thiopheneacrylic acid;E-3-(2-thienyl)propenoic acid;DTXSID50901215;NSC4247;CHEBI:188283;HMS1404J14;NSC-4247;3-(2-Thienyl)acrylic acid, 98%;BBL037013;BDBM50342412;GEO-02856;STK057349;trans-3-(thiophen-2-yl)acrylic acid;AKOS000266291;AKOS025310061;CS-W018039;IDI1_007375;AM808025;PS-11882;T1138;EN300-00019;A22502;EN300-305660;(E)-3-(THIOPHEN-2-YL)-2-PROPENOIC ACID;3T-0655;A855561;(2Z)-3-(THIOPHEN-2-YL)PROP-2-ENOIC ACID;J-511004;J-640121;J-800125;Q27280816;Z56855126;F3145-2787

Chemical Property of 3-(2-Thienyl)acrylic acid

Chemical Property:

• Appearance/Colour: Slightly beige powder
• Vapor Pressure: 0.000551mmHg at 25°C
• Melting Point: 145-148 °C(lit.)
• Refractive Index: 1.5100 (estimate)
• Boiling Point: 298.9oC at 760 mmHg
• PKA: 4.34±0.10(Predicted)
• Flash Point: 134.6oC
• PSA: 65.54000
• Density: 1.2950 (rough estimate)
• LogP: 1.84590
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: Chloroform, Methanol
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 154.00885060
• Heavy Atom Count: 10
• Complexity: 154

Purity/Quality:

98%,99%, ^*data from raw suppliers

(E)-2-ThiopheneacrylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CSC(=C1)C=CC(=O)O
• Isomeric SMILES: C1=CSC(=C1)/C=C/C(=O)O
• Uses: (E)-2-Thiopheneacrylic Acid is used in the synthesis of anti-HIV HEPT analogs. Also used in the synthesis of benzimidazole and caffeine (C080100) analogs as inhibitors of monoamine oxidase B.

Technology Process of 3-(2-Thienyl)acrylic acid

There total 34 articles about 3-(2-Thienyl)acrylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

thiophene-2-carbaldehyde (98-03-3) + malonic acid (141-82-2) → 3-(2-thienyl)-2-propenoic acid (1124-65-8,15690-25-2,51019-83-1)

Guidance literature:

With ammonium acetate; for 0.05h; Irradiation;

Reference yield: 97.0%

2-Iodothiophene (3437-95-4,149762-92-5) + acrylic acid (79-10-7) → 3-(2-thienyl)-2-propenoic acid (1124-65-8,15690-25-2,51019-83-1)

Guidance literature:

With potassium hydroxide; PS-PEG-NH-C(O)C6H4PPh2-PdCl(η³-C3H5); at 50 ℃;

DOI:10.1055/s-2002-35605

Reference yield: 92.0%

ethyl (E)-3-(thiophen-2-yl)acrylate (13979-15-2,70326-81-7) → 3-(2-thienyl)-2-propenoic acid (1124-65-8,15690-25-2,51019-83-1)

Guidance literature:

With potassium hydroxide; for 4h; Heating;

DOI:10.1002/chem.200501034

upstream raw materials:

thiophene-2-carbaldehyde

malonic acid

ethyl (E)-3-(thiophen-2-yl)acrylate

methyl (E)-3-(2-thienyl)propenoate

Downstream raw materials:

3-thiophen-2-yl-acryloyl chloride

oenanthic acid

trans-β-(2-thienyl)acrylamide

L-3-(2-thienyl)alanine

Refernces

• 1、 Pitchumani, Venkatachalam,Breugst, Martin,Lupton, David W.. "Enantioselective Rauhut–Currier Reaction with β-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes". supporting information. p. 9413 - 9418. Retrieved 2021/12/09.
• 2、 Liu, Feng,Wu, Na,Cheng, Xu. "Chlorination Reaction of Aromatic Compounds and Unsaturated Carbon-Carbon Bonds with Chlorine on Demand". supporting information. p. 3015 - 3020. Retrieved 2021/05/05.