1-Bromo-1-propene

Base Information

• Chemical Name: 1-Bromo-1-propene
• CAS No.: 590-14-7
• Molecular Formula: C3H5 Br
• Molecular Weight: 120.977
• Hs Code.: 29033919
• European Community (EC) Number: 209-671-6
• Wikidata: Q105182253
• Mol file: 590-14-7.mol

Synonyms:1-Bromo-1-propene;1-bromoprop-1-ene;590-14-7;Propenyl bromide;bromopropene;1-propene, 1-bromo-, (1Z)-;C3-H5-Br;1-Bromo-1-propene (cis and trans);1 -bromopropene;alpha-bromopropene;Bromo-1-propene;1-bromo 1-propene;1-bromanylprop-1-ene;AKOS028109014;AB00109;B1038;FT-0607429;FT-0694222;D88739;A801548

Chemical Property of 1-Bromo-1-propene

Chemical Property:

• Vapor Pressure: 219mmHg at 25°C
• Melting Point: −116 °C(lit.)
• Refractive Index: n20/D 1.454
• Boiling Point: 64-65 °C(lit.)
• Flash Point: °C
• PSA: 0.00000
• Density: 1.425g/cm³
• LogP: 1.91490
• Storage Temp.: 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 119.95746
• Heavy Atom Count: 4
• Complexity: 22.5

Purity/Quality:

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

1-PropenylBromide(mixtureofisomers) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Halogenated Aliphatics, Unsaturated
• Canonical SMILES: CC=CBr
• Uses: 1-Propenyl bromide is a useful building block, especially when a 3 carbon addition is required, such as its use in the synthesis of the pharmaceutical spilanthol. 1-Bromo-1-propene upon n-BuLi treatment generates the propynyllithium anion, in situ, which later undergoes nucleophilic addition reactions. Some of its other applications are:Synthesis of organic reagents such as methyl but-2-ynoate and 1-iodopropyne.Preparation o f intermediates in the total synthesis of (+)-aphanamol I and skyllamycins A-C.Synthesis of allylated pyrazoles, aryl alkynyl sulfides and allenamides.

Technology Process of 1-Bromo-1-propene

There total 17 articles about 1-Bromo-1-propene 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: 92.0%

2-butenoic acid (3724-65-0) → 1-bromo-1-propene (590-14-7)

Guidance literature:

With [bis(acetoxy)iodo]benzene; tetraethylammonium bromide; In dichloromethane; at 20 ℃; for 8h;

DOI:10.1248/cpb.57.1243

Reference yield: 65.0%

(E)-but-2-enoic acid (107-93-7) → 1-bromo-1-propene (590-14-7)

Guidance literature:

With N,N-dimethyl-formamide; potassium bromide; trichlorophosphate; In acetonitrile; at 20 ℃; Reagent/catalyst; Sonication;

DOI:10.1080/15533174.2014.989573

Reference yield:

erythro-2,3-dibromobutanoic acid (600-30-6,26697-68-7,90429-42-8,125810-56-2) + water (7732-18-5) → 1-bromo-1-propene (590-14-7) + (E)-2-bromo-2-butenoic acid (36297-22-0) + hydrogen bromide (10035-10-6,12258-64-9)

Guidance literature:

DOI:10.1111/j.1467-842X.2003.tb00402.x

upstream raw materials:

pyridine

2,3-dibromobutanoic acid

1,2-Dibromopropane

sodium phenoxide

Downstream raw materials:

1-phenyl-2-butyn-1-one

1,1,2-tribromo-propane

1,2,3-tribromopropane

hept-2-yn-4-one

Refernces

• 1、 Fursule, Ravindra Abhykumar,Patil, Pravin Onkar,Shewale, Bharti Devaji,Kosalge, Satish Bhaskar,Deshmukh, Prashant Krishnarao,Patil, Dilip Ashok. "Novel system for decarboxylative bromination of α,β-unsaturated carboxylic acids with diacetoxyiodobenzene". experimental part. p. 1243 - 1245. Retrieved 2010/08/06.