2-(Bromomethyl)acrylic acid

Base Information

• Chemical Name: 2-(Bromomethyl)acrylic acid
• CAS No.: 72707-66-5
• Molecular Formula: C4H5 Br O2
• Molecular Weight: 164.986
• Hs Code.: 2916190090
• European Community (EC) Number: 276-774-0
• DSSTox Substance ID: DTXSID30223008
• Nikkaji Number: J149.970J
• Wikidata: Q83101373
• Mol file: 72707-66-5.mol

Synonyms:2-(Bromomethyl)acrylic acid;72707-66-5;2-(bromomethyl)prop-2-enoic acid;2-(Bromomethyl)propenoic acid;2-Propenoic acid, 2-(bromomethyl)-;2-Bromomethyl-acrylic acid;EINECS 276-774-0;bromomethylacrylic acid;a-Bromomethacrylic Acid;2-Bromomethylacrylic acid;2-bromomethyl acrylic acid;2-(Bromomethyl)acrylicacid;2-(bromomethyl) acrylic acid;2-(bromomethyl)-acrylic acid;SCHEMBL346921;NOOYFQLPKUQDNE-UHFFFAOYSA-;DTXSID30223008;.alpha.-(Bromomethyl)acrylic acid;2-(Bromomethyl)-2-propenoic acid;2-(Bromomethyl)acrylic acid, 98%;MFCD00004259;AKOS015919370;AS-40257;BP-31115;B4048;FT-0608741;A837600

Chemical Property of 2-(Bromomethyl)acrylic acid

Chemical Property:

• Vapor Pressure: 0.00214mmHg at 25°C
• Melting Point: 70-73 °C(lit.)
• Boiling Point: 268.8°C at 760 mmHg
• PKA: 3.45±0.11(Predicted)
• Flash Point: 116.4°C
• PSA: 37.30000
• Density: 1.696g/cm³
• LogP: 1.02210
• Storage Temp.: 2-8°C
• Solubility.: soluble in Methanol
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 163.94729
• Heavy Atom Count: 7
• Complexity: 97.9

Purity/Quality:

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

2-(Bromomethyl)acrylic Acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C=C(CBr)C(=O)O
• Uses: 2-(Bromomethyl)acrylic Acid is a chemical intermediate in the synthesis of various complex organic compounds and pharmaceuticals. Reacts with aldehydes and ketones to form α-methylene-butyrolactones. Used in the synthesis of methotrexate analogues.

Technology Process of 2-(Bromomethyl)acrylic acid

There total 5 articles about 2-(Bromomethyl)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: 74.0%

poly(methacrylic acid) (79-41-4,25087-26-7,50867-57-7) → 2-(bromomethyl)acrylic acid (72707-66-5)

Guidance literature:

With N,N'-dibromo-N,N'-1,2-ethylene bis(2,5-dimethylbenzene sulfonamide); dibenzoyl peroxide; In tetrachloromethane; at 20 ℃; for 6h;

DOI:10.1081/SCC-120005417

Reference yield: 65.0%

diethyl bis(hydroxymethyl)malonate (20605-01-0) → 2-(bromomethyl)acrylic acid (72707-66-5)

Guidance literature:

With hydrogen bromide; at 120 ℃; for 14h;

DOI:10.1002/jccs.200800065

Reference yield: 57.0%

→ 2-(bromomethyl)acrylic acid (72707-66-5)

Guidance literature:

upstream raw materials:

3-bromo-2-(bromomethyl)propionic acid

diethyl bis(hydroxymethyl)malonate

poly(methacrylic acid)

ethyl 2-(hydroxymethyl)acrylate

Downstream raw materials:

ethyl 2-bromomethyl-2-propenoate

γ-benzyl-α-methylene-γ-butyrolactone

5-(4-chlorophenyl)-3-methylenedihydrofuran-2(3H)-one

1,5-Hexadien

Refernces

• 1、 Sun, Chong-Si,Cheng, Hsiu-Yi,Lin, Yu-Shiang,Hou, Duen-Ren. "Practical preparation of 2-halomethyl-allyl carboxylates". . p. 435 - 438. Retrieved 2008/12/22.
• 2、 Khazaei, Ardeshir,Vaghei, Ramin Ghorbani,Karkhanei, Ebrahim. "Bromination of organic allylic compounds by using N,N′-dibromo-N,N′-1,2-ethane diyl bis(2,5-dimethyl benzene sulphonyl)amine". . p. 2107 - 2113. Retrieved 2007/10/03.