4-Bromocrotonic acid

Base Information

• Chemical Name: 4-Bromocrotonic acid
• CAS No.: 13991-36-1
• Molecular Formula: C4H5 Br O2
• Molecular Weight: 164.986
• Hs Code.: 29161900
• European Community (EC) Number: 678-082-8
• DSSTox Substance ID: DTXSID80878724
• Nikkaji Number: J950.409E,J3.152.358C
• Wikidata: Q72452174
• Mol file: 13991-36-1.mol

Synonyms:4-bromocrotonic acid

Chemical Property of 4-Bromocrotonic acid

Chemical Property:

• Vapor Pressure: 0.000626mmHg at 25°C
• Melting Point: 74 °C
• Boiling Point: 287.6°Cat760mmHg
• PKA: 4.13±0.10(Predicted)
• Flash Point: 127.7°C
• PSA: 37.30000
• Density: 1.718g/cm³
• LogP: 1.02210
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 163.94729
• Heavy Atom Count: 7
• Complexity: 87.7

Purity/Quality:

(E)-4-BromocrotonicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R34:
• Hazard Codes: R34:
• Statements: 34
• Safety Statements: 36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C=CC(=O)O)Br
• Isomeric SMILES: C(/C=C/C(=O)O)Br
• Uses: (E)-4-Bromocrotonic Acid acts as a fatty acid blocking agent. It is used to selectively adjust levels of long-chain acyl CoA and carnitine in aerobic and ischemic myocardium. It is also an intermediate used to prepare tetrahydropyridothienopyrimidine derivatve with antiproliferative activities.

Technology Process of 4-Bromocrotonic acid

There total 18 articles about 4-Bromocrotonic 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%

(E)-but-2-enoic acid (107-93-7) → 4-bromocrotonic acid (13991-36-1)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; Reflux;

DOI:10.1002/ardp.201400098

Reference yield: 84.4%

methyl-4-bromo-2-butenoate (1117-71-1,56699-18-4,6000-00-6) → 4-bromocrotonic acid (13991-36-1)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; for 3h;

DOI:10.1039/c8cc09558b

Reference yield: 81.0%

(E)-4-chlorobut-2-enoic acid (26340-58-9) → 4-bromocrotonic acid (13991-36-1)

Guidance literature:

With sodium bromide; In acetone; at 50 ℃; for 120h;

DOI:10.1021/ja9042824

upstream raw materials:

methyl-4-bromo-2-butenoate

4-bromo-trans-crotonic acid ethyl ester

vinyl glycolic acid

(E)-but-2-enoic acid

Downstream raw materials:

(E)-4-phenylbut-2-enoic acid

trans-2-undecenoic acid

(E)-2-Hexenoic acid

trans-4-aminocrotonic acid

Refernces

• 1、 Gammack Yamagata, Adam D.,Datta, Swarup,Jackson, Kelvin E.,Stegbauer, Linus,Paton, Robert S.,Dixon, Darren J.. "Enantioselective desymmetrization of prochiral cyclohexanones by organocatalytic intramolecular michael additions to α,β-unsaturated esters". . p. 4899 - 4903. Retrieved 2015.
• 2、 Pinza,Pifferi. "Convenient synthesis of (RS)-4-amino-3-hydroxybutyric acid.". . p. 120 - 121. Retrieved 1978.
• 3、 Bai, Chengfeng,Luo, Guoshun,Ren, Shengnan,Wu, Shuangjie,Xiang, Hua,Zhu, Meiqi. "Benzothiophene derivatives as selective estrogen receptor covalent antagonists: Design, synthesis and anti-ERα activities". . . Retrieved 2021/09/13.
• 4、 Qian, Linghui,Pan, Sijun,Lee, Jun-Seok,Ge, Jingyan,Li, Lin,Yao, Shao Q.. "Live-cell imaging and profiling of c-Jun N-terminal kinases using covalent inhibitor-derived probes". supporting information. p. 1092 - 1095. Retrieved 2019/01/29.