3-(4-Bromo-2-thienyl)acrylic acid

Base Information

• Chemical Name: 3-(4-Bromo-2-thienyl)acrylic acid
• CAS No.: 103686-16-4
• Molecular Formula: C7H5BrO2S
• Molecular Weight: 233.08200
• Hs Code.: 2934999090
• European Community (EC) Number: 695-468-1
• DSSTox Substance ID: DTXSID101263715
• Nikkaji Number: J308.032C
• ChEMBL ID: CHEMBL1771613
• Mol file: 103686-16-4.mol

Synonyms:3-(4-bromo-2-thienyl)acrylic acid;144558-44-1;103686-16-4;3-(4-bromothiophen-2-yl)acrylic acid;trans-3-(4-Bromothiophen-2-yl)acrylic acid;(E)-3-(4-bromothiophen-2-yl)prop-2-enoic acid;(2E)-3-(4-bromothiophen-2-yl)prop-2-enoic acid;(e)-3-(4-bromothiophen-2-yl)acrylic acid;3-(4-Bromo-thiophen-2-yl)-acrylic acid;3-(4-bromothiophen-2-yl)prop-2-enoic Acid;SCHEMBL380483;SCHEMBL380484;CHEMBL1771613;VHKFUECAKTYKCR-OWOJBTEDSA-N;DTXSID101263715;3-(4-Bromo-2-thienyl)acrylicacid;MFCD00051662;3-(4-Bromothiophen-2-yl)acrylicacid;AKOS009158749;3-(4-bromo-thiophen-2-yl)acrylic acid;(E)-4-Bromo-3-(2-thienyl)acrylic acid;(2E)-3-(4-bromo-2-thienyl)acrylic acid;CS-0345028;3-(4-bromothiophen-2-yl)-(E)-acrylic acid;EN300-94383;(E)-3-(4-Bromo-thiophen-2-yl)-acrylic acid;EN300-384216;(2E)-3-(4-Bromo-2-thienyl)-2-propenoic acid;(2E)-3-(4-bromothiophen-2-yl)prop-2-enoicacid;A808233;trans-3-(4-Bromothiophen-2-yl)acrylic acid, 97%;W-205610;Z2312944403

Chemical Property of 3-(4-Bromo-2-thienyl)acrylic acid

Chemical Property:

• Melting Point: 168-173 °C
• PSA: 65.54000
• LogP: 2.60840
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 231.91936
• Heavy Atom Count: 11
• Complexity: 181

Purity/Quality:

99% ^*data from raw suppliers

trans-3-(4-Bromothiophen-2-yl)acrylic acid 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(SC=C1Br)C=CC(=O)O
• Isomeric SMILES: C1=C(SC=C1Br)/C=C/C(=O)O

Technology Process of 3-(4-Bromo-2-thienyl)acrylic acid

There total 4 articles about 3-(4-Bromo-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: 100.0%

4-Bromothiophen-2-aldehyde (18791-75-8) + malonic acid (141-82-2) → trans-3-(4-bromothiophen-2-yl)propenoic acid (103686-16-4)

Guidance literature:

With piperidine; pyridine; at 100 ℃;

DOI:10.1016/j.bmcl.2006.09.050

Reference yield:

piperidine (110-89-4) + 4-Bromothiophen-2-aldehyde (18791-75-8) + aqueous potassium hydroxide → trans-3-(4-bromothiophen-2-yl)propenoic acid (103686-16-4)

Guidance literature:

With malonic acid; In pyridine;

Reference yield:

thiophene-2-carbaldehyde (98-03-3) → trans-3-(4-bromothiophen-2-yl)propenoic acid (103686-16-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / Br₂; AlCl₃ / CH₂Cl₂

2: 96 percent / piperidine / pyridine / 22 h / 100 °C

With aluminium trichloride; bromine; piperidine; In pyridine; dichloromethane; 2: Knoevenagel reaction;

DOI:10.1016/j.bmcl.2006.12.035

upstream raw materials:

4-Bromothiophen-2-aldehyde

malonic acid

thiophene-2-carbaldehyde

piperidine

Downstream raw materials:

(S)-2-amino-3-(4-bromothiophen-2-yl)propanoic acid

3-bromo-4-chloro-[3,2-c]-thienopyridine

Refernces

• 1、 Ahmed, Syed T.,Parmeggiani, Fabio,Weise, Nicholas J.,Flitsch, Sabine L.,Turner, Nicholas J.. "Synthesis of Enantiomerically Pure Ring-Substituted l -Pyridylalanines by Biocatalytic Hydroamination". supporting information. p. 5468 - 5471. Retrieved 2016/11/17.
• 2、 Van Veldhoven,Blad,Artsen,Klopman,Wolfram,Abdelkadir,Lane,Brussee,Ijzerman. "Structure-activity relationships of trans-substituted-propenoic acid derivatives on the nicotinic acid receptor HCA2 (GPR109A)". supporting information; experimental part. p. 2736 - 2739. Retrieved 2011/06/20.