1-Bromo-2-butanone

Base Information

• Chemical Name: 1-Bromo-2-butanone
• CAS No.: 816-40-0
• Molecular Formula: C4H7BrO
• Molecular Weight: 151.003
• Hs Code.: 29147000
• European Community (EC) Number: 212-431-3
• UN Number: 1693
• UNII: 4UPM4J7CVA
• DSSTox Substance ID: DTXSID00231216
• Nikkaji Number: J42.075A
• Wikipedia: Bromomethyl_ethyl_ketone
• Wikidata: Q9127828
• Mol file: 816-40-0.mol

Synonyms:1-BROMO-2-BUTANONE;816-40-0;1-bromobutan-2-one;2-Butanone, 1-bromo-;Bromomethyl ethyl ketone;1-Bromobutanone;TL 819;1-bromo-butan-2-one;EINECS 212-431-3;4UPM4J7CVA;BRN 0741894;4-01-00-03258 (Beilstein Handbook Reference);(bromomethyl)ethyl ketone;bromobutanone;bromobutan-2-one;2-Oxobutyl bromide;l-bromo-2-butanone;1-bromo-2-oxo-butane;UNII-4UPM4J7CVA;1-Bromo-2-butanone, 95%;SCHEMBL113452;DTXSID00231216;BCP08723;MFCD00000207;AKOS005207050;LS-46645;CS-0131119;FT-0607448;F10475;1-Bromo-2-butanone,with calcium carbonate stabilizer;J-504459;Q9127828;1-Bromo-2-butanone (stabilized with calcium carbonate)

Chemical Property of 1-Bromo-2-butanone

Chemical Property:

• Appearance/Colour: colorless to light yellow liquid
• Vapor Pressure: 2.96mmHg at 25°C
• Refractive Index: n20/D 1.465(lit.)
• Boiling Point: 155.9 °C at 760 mmHg
• Flash Point: 68.3 °C
• PSA: 17.07000
• Density: 1.439 g/cm³
• LogP: 1.36040
• Storage Temp.: Keep Cold
• Sensitive.: Lachrymatory
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 149.96803
• Heavy Atom Count: 6
• Complexity: 51.5
• Transport DOT Label: Poison

Purity/Quality:

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

1-Bromo-2-butanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi,F
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-27-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(=O)CBr
• Uses: 1-Bromo-2-butanone (bromomethyl ethyl ketone) was used as a potential regulatory site-directed reagent for the residue C221 on pyruvate decarboxylase. It was also used as a reagent for aromatic bromination with sodium hydride in DMSO and in a microwave-assisted preparation of fused heterocycles.

Technology Process of 1-Bromo-2-butanone

There total 21 articles about 1-Bromo-2-butanone 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%

1-(trimethylsilyl)-2-butanone (14091-67-9) → 1-Bromo-2-butanone (816-40-0)

Guidance literature:

With bromine; In dichloromethane; at -78 ℃;

DOI:10.1016/0022-328X(86)80349-7

Reference yield: 95.0%

1-morpholinopropane-1-one (30668-14-5) + dimethyltitanocene (1271-66-5) → 1-Bromo-2-butanone (816-40-0)

Guidance literature:

1-morpholinopropane-1-one; dimethyltitanocene; 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: 94.0%

N-propionylpiperidine (14045-28-4) + dimethyltitanocene (1271-66-5) → 1,1-dibromo-butan-2-one (3479-86-5) + 1-Bromo-2-butanone (816-40-0)

Guidance literature:

N-propionylpiperidine; dimethyltitanocene; 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

upstream raw materials:

diazomethane

propanoyl bromide

1-butylene

butanone

Downstream raw materials:

4-ethylthiazole

N-phenylglycine ethyl ester

2-oxo-1-(2-oxo-butyl)-cyclohexanecarboxylic acid ethyl ester

pseudoionone

Refernces

• 1、 Altmann, Karl-Heinz,Liniger, Marc,Neuhaus, Christian M.. "Ring-closing metathesis approaches towards the total synthesis of rhizoxins". supporting information. . Retrieved 2020/10/18.
• 2、 Gholizadeh, Saeed,Safa, Kazem D.,Noroozi Pesyan, Nader. "Synthesis of various cyclopropyl methyl bromide and its derivatives from ketones and/or aldehydes and some β-dicarbonyl compounds in the presence of BrCN and Et3N". . p. 1239 - 1253. Retrieved 2019/04/27.