2-Bromoacrylic acid

Base Information

• Chemical Name: 2-Bromoacrylic acid
• CAS No.: 10443-65-9
• Molecular Formula: C3H3BrO2
• Molecular Weight: 150.96
• Hs Code.: 2916190090
• European Community (EC) Number: 233-928-1
• NSC Number: 227848
• DSSTox Substance ID: DTXSID50146487
• Nikkaji Number: J212.398C
• Wikidata: Q72451357
• ChEMBL ID: CHEMBL34533
• Mol file: 10443-65-9.mol

Synonyms:2-Bromoacrylic acid;10443-65-9;2-bromoprop-2-enoic acid;2-BROMOACRYLICACID;EINECS 233-928-1;CCRIS 5478;.alpha.-Bromoacrylic acid;NSC 227848;bromoacrylic acid;C3H3BrO2;2-Bromo-acrylic acid;Alpha-Bromo Acrylic Acid;2-Bromoacrylic acid, 95%;2-Propenoic acid, 2-bromo-;CHEMBL34533;SCHEMBL287264;DTXSID50146487;MFCD00014333;NSC227848;AKOS015894446;NSC-227848;AS-44486;LS-188420;CS-0376420;FT-0611519;EN300-146230;2,2,2-TRIFLUOROETHYL3-NITROPHENYLCARBAMATE

Chemical Property of 2-Bromoacrylic acid

Chemical Property:

• Vapor Pressure: 0.0333mmHg at 25°C
• Melting Point: 62-65 °C(lit.)
• Refractive Index: 1.4804 (estimate)
• Boiling Point: 224.5 °C at 760 mmHg
• PKA: 2.41±0.11(Predicted)
• Flash Point: 89.6 °C
• PSA: 37.30000
• Density: 1.869 g/cm³
• LogP: 0.97960
• Storage Temp.: Amber Vial, Hygroscopic, Refrigerator, Under inert atmosphere
• Sensitive.: Hygroscopic
• Solubility.: DMSO (Soluble), Methanol (Sparingly)
• Water Solubility.: It is miscible with water.
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 149.93164
• Heavy Atom Count: 6
• Complexity: 86.8

Purity/Quality:

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

2-Bromo-2-propenoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-36/37
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=C(C(=O)O)Br
• Uses: 2-Bromoacrylic acid is used as a raw material on QSAR models to predict mutagenicity of acrylates. It is used as a pharmaceutical intermediate.

Technology Process of 2-Bromoacrylic acid

There total 17 articles about 2-Bromoacrylic 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: 94.0%

2,3-dibromopropionic acid (600-05-5) → 2-bromo-2-propenoic acid (10443-65-9)

Guidance literature:

In water; dimethyl sulfoxide; at 75 ℃; for 8h;

DOI:10.1021/ol7021142

Reference yield: 40.0%

2,3-dibromopropionic acid (600-05-5) + cyanoacetic acid (372-09-8) → 2-bromo-2-propenoic acid (10443-65-9) + cyclopropane-1,1,2-tricarboxylic acid (702-90-9)

Guidance literature:

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In water; at 20 ℃; for 1h;

DOI:10.1016/j.molstruc.2004.03.018

Reference yield: 24.5%

Methyl 2,3-dibromopropionate (1729-67-5) → 2-bromo-2-propenoic acid (10443-65-9)

Guidance literature:

With barium dihydroxide;

DOI:10.1021/j100162a026

upstream raw materials:

2,3-dibromopropionic acid

Methyl 2,3-dibromopropionate

2,2-dibromopropionic acid

2-bromo-3-chloro-propionic acid

Downstream raw materials:

8-Hydroxy-dihydrothiazolo<3,2-a>-pyridinium-3-carboxylat

1-(1'-bromoacroyl)-1,2,5,6-tetrahydropyridine

3-(benzylthio)acrylic acid

2,3-dibromopropionic acid

Refernces

• 1、 Khachikyan,Tovmasyan,Indzhikyan. "Reaction of 2,3-dihalopropionic acids and their derivatives with P- and N-nucleophiles". . p. 1889 - 1894. Retrieved 2005.
• 2、 Durig, J. R.,Wang, Ai-Ying,Little, T. S.,Brletic, P. A.. "Conformational Stability, Barriers to Internal Rotation, Vibrational Assignment, and RHF/STO-3G* Calculations of 2-Bromopropenoyl Fluoride". . p. 3569 - 3578. Retrieved 1991.
• 3、 Li, Wei,Li, Jianchang,Wan, Zhao-Kui,Wu, Junjun,Massefski, Walter. "Preparation of α-haloacrylate derivatives via dimethyl sulfoxide-mediated selective dehydrohalogenation". . p. 4607 - 4610. Retrieved 2008/03/13.