Bromoacetone

Base Information

• Chemical Name: Bromoacetone
• CAS No.: 598-31-2
• Molecular Formula: C3H5BrO
• Molecular Weight: 136.976
• Hs Code.: 29147000
• European Community (EC) Number: 209-928-2
• ICSC Number: 1074
• UN Number: 1569
• UNII: 3O8L0EWR5Q
• DSSTox Substance ID: DTXSID6060507
• Nikkaji Number: J3.305G
• Wikipedia: Bromoacetone
• Wikidata: Q421365
• Pharos Ligand ID: YHCMAS34DGT8
• Metabolomics Workbench ID: 57923
• ChEMBL ID: CHEMBL1085947
• Mol file: 598-31-2.mol

Synonyms:bromoacetone

Chemical Property of Bromoacetone

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 7.19mmHg at 25°C
• Melting Point: -36.5 °C
• Refractive Index: 1.449
• Boiling Point: 136.999 °C at 760 mmHg
• Flash Point: 75.324 °C
• PSA: 17.07000
• Density: 1.55 g/cm³
• LogP: 0.97030
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 135.95238
• Heavy Atom Count: 5
• Complexity: 42.2
• Transport DOT Label: Poison Inhalation Hazard Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Bromoacetone ^*data from reagent suppliers

Safty Information:

• Statements: 11-23/24/25-34
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Other Toxic Gases & Vapors
• Canonical SMILES: CC(=O)CBr
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: Lachrymation. The substance is severely irritating to the eyes, skin and respiratory tract.
• Uses: Chemical war gas.

Technology Process of Bromoacetone

There total 73 articles about Bromoacetone 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: 95.0%

acetone (67-64-1) → 1-bromoacetone (598-31-2)

Guidance literature:

With Cl(CF₂)4SO₂Br; at 0 ℃;

Reference yield: 90.0%

dimethyltitanocene (1271-66-5) + N,N-dimethyl acetamide (127-19-5,116057-81-9) → 1-bromoacetone (598-31-2)

Guidance literature:

dimethyltitanocene; N,N-dimethyl acetamide; In toluene; at 65 ℃; Schlenk technique; Inert atmosphere;

With bromine; In toluene; at -78 ℃; for 0.0333333h; Schlenk technique; Inert atmosphere;

With water; In toluene; at 20 ℃; for 1h; regioselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1080/00397911.2013.765484

Reference yield: 89.0%

methanol (67-56-1) + (E)-1,4-dibromo-2,3-dimethylbut-2-ene (6044-73-1) → 1-bromo-2-hydroperoxy-2-methoxypropane + 1-bromoacetone (598-31-2)

Guidance literature:

With ozone; at 0 ℃; for 0.416667h;

DOI:10.1021/jo00224a007

upstream raw materials:

4-methyleneoxetan-2-one

N-Bromosuccinimide

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

diethyl ether

Downstream raw materials:

N-acetonylpyridinium bromide

6-bromo-2-methylimidazo[1,2-a]pyridine

6-iodo-2-methylimidazo[ 1,2-a]pyridine

6-nitro-2-methylimidazo[1,2-a]pyridine

Refernces

• 1、 Toullec,Dubois. "-". . p. 5518. Retrieved 1976.
• 2、 Fleck et al.. "-". . p. 998,1005. Retrieved 1949.
• 3、 Chiang, Y.,Kresge, A. J.,Morimoto, H.,Williams, P. G.. "Kinetic Isotope Effects on the Hydroxide Ion Catalyzed Enolization of Acetone: Relationship between Deuterium and Tritium Isotope Effects". . p. 3981 - 3982. Retrieved 1992.
• 4、 Berenstein, Igal,Agreda, Jesus,Barragan, Daniel. "Induction period in the BrO3 -, Ce(III), H2SO4, oxalic acid and ketone oscillating reaction". . p. 4601 - 4603. Retrieved 1999.
• 5、 -. "Novel method for synthesizing 1-bromo-2,2-dimethoxypropane". Page/Page column 4-6. . Retrieved 2020/07/15.
• 6、 Ma, Weifeng,Chen, Peng,Huo, Xiansen,Ma, Yufeng,Li, Yanhong,Diao, Pengcheng,Yang, Fang,Zheng, Shengquan,Hu, Mengjin,You, Wenwei,Zhao, Peiliang. "Development of triazolothiadiazine derivatives as highly potent tubulin polymerization inhibitors: Structure-activity relationship, in vitro and in vivo study". . . Retrieved 2020/10/08.