2-Bromo-2-butenal

Base Information

• Chemical Name: 2-Bromo-2-butenal
• CAS No.: 24247-53-8
• Molecular Formula: C4H5 Br O
• Molecular Weight: 148.987
• Hs Code.: 2913000090
• DSSTox Substance ID: DTXSID001023346
• Mol file: 24247-53-8.mol

Synonyms:2-bromobut-2-enal;C4H5BrO;C4-H5-Br-O;2-Butenal, 2-bromo- (9CI);55947-13-2;3-01-00-02981 (Beilstein Handbook Reference);DTXSID001023346;AKOS026727923

Chemical Property of 2-Bromo-2-butenal

Chemical Property:

• Vapor Pressure: 1.26mmHg at 25°C
• Refractive Index: 1.5184
• Boiling Point: 173.6°C at 760 mmHg
• Flash Point: 92.1°C
• PSA: 17.07000
• Density: 1.512g/cm³
• LogP: 1.48400
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 147.95238
• Heavy Atom Count: 6
• Complexity: 75.6

Purity/Quality:

99% ^*data from raw suppliers

2-bromobut-2-enal ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C(C=O)Br

Technology Process of 2-Bromo-2-butenal

There total 21 articles about 2-Bromo-2-butenal 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%

crotonaldehyde (123-73-9,4170-30-3) → 2-bromocrotonaldehyde (24247-53-8)

Guidance literature:

With pyridine; Phenylselenyl bromide; for 24h; Ambient temperature;

DOI:10.1016/S0040-4039(01)81890-6

Reference yield: 89.0%

trans-Crotonaldehyde (123-73-9,4170-30-3) → (Z)-2-bromobut-2-enal (33718-99-9,24247-53-8,55947-13-2)

Guidance literature:

trans-Crotonaldehyde; With bromine; In dichloromethane; at 0 ℃; for 1.16667h; Inert atmosphere;

With triethylamine; In dichloromethane; at 20 ℃; for 1.5h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/jo2020246

Reference yield: 86.0%

(2-Bromo-3,3-dihydroxy-1-methyl-propyl)-dimethyl-sulfonium; bromide (83769-15-7,83784-48-9) → (Z)-2-bromobut-2-enal (33718-99-9,24247-53-8,55947-13-2) + 2-bromocrotonaldehyde (55947-13-2)

Guidance literature:

With sodium hydrogencarbonate; for 72h; Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1139/v82-322

upstream raw materials:

2,3-dibromo-butyraldehyde

sodium acetate

2-bromo-crotonaldehyde diethylacetal

4,5-dibromo-hex-2-enoic acid

Downstream raw materials:

N-Formylpiperidine

α-piperidinocrotonaldehyde

1,2-dipiperidino-ethene

1,2-Dipiperidinoethylen