3017-68-3

Basic information

• Product Name: (Z)-2-BROMO-2-BUTENE
• Synonyms: 2-BROMO-CIS-2-BUTENE;CIS-2-BROMO-2-BUTENE;(Z)-2-BROMO-2-BUTENE;2-Butene, 2-bromo-, (Z)-;2-butene,2-bromo-,(Z)-;cis-2-bromo-but-2-ene;(Z)-2-BROMO-2-BUTENE 97%;(Z)-2-bromobut-2-ene
• CAS NO: 3017-68-3
• Molecular Formula: C₄H₇Br
• Molecular Weight: 135
• Product Categories: Alkenyl;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 3017-68-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: -111.2°C
• Boiling Point: 84 °C(lit.)
• Flash Point: 30 °F
• Appearance: /
• Density: 1.332 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.459(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (Z)-2-BROMO-2-BUTENE(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-2-BROMO-2-BUTENE(3017-68-3)
• EPA Substance Registry System: (Z)-2-BROMO-2-BUTENE(3017-68-3)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 16-29-33-7/9
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 3017-68-3(Hazardous Substances Data)

Usage

General Description

(Z)-2-Bromo-2-butene, also known as cis-2-bromo-2-butene, is an organic compound with the formula C4H7Br. It is a colorless liquid with a pungent odor and is primarily used as a reagent in organic synthesis and as an intermediate in the production of pharmaceuticals and agrochemicals. It is also used as a monomer in the production of polymers and plastics. (Z)-2-Bromo-2-butene is a highly reactive compound and should be handled with care due to its potential to cause irritation to the skin, eyes, and respiratory system. It is also flammable and should be stored and handled in accordance with appropriate safety protocols.

InChI:InChI=1S/C4H7Br/c1-3-4(2)5/h3H,1-2H3/b4-3+

Upstream product

• 503-17-3 dimethylacetylene 
• 598-71-0 DL-2,3-dibromobutane 
• 590-18-1 (Z)-2-Butene 
• 5408-86-6 2,3-dibromobutane 
• 13294-71-8 2-bromo-but-2-ene 
• 13170-43-9 (trimethylsilyl)methylmagnesium chloride 
• 10035-10-6 hydrogen bromide 
• 64-17-5 ethanol 
• 62127-47-3 1,2,2-tribromo-1-methylpropane 
• 107-21-1 ethylene glycol 
• 3017-71-8 (E)-2-bromobut-2-ene 
• 7726-95-6 bromine 
• 107-00-6 but-1-yne 

Downstream Products

• 3017-71-8 (E)-2-bromobut-2-ene 
• 565-63-9 Angelic acid 
• 62127-47-3 1,2,2-tribromo-1-methylpropane 
• 91345-39-0 2-p-tolylsulfanyl-but-2t-ene 
• 57024-90-5 (Z)-3-Methyl-2-undecene 
• 72138-56-8 (Z)-(1-Methyl-1-propenyl)diphenylphosphine 
• 598-71-0 DL-2,3-dibromobutane 
• 50341-35-0 2,2-dibromobutane 
• 5780-13-2 meso-2,3-dibromo-butane 
• 513-86-0 3-hydroxy-2-butanon 
• 104722-44-3 (1E,3Z)-1-(3-methylpenta-1,3-dienyl)benzene 
• 20414-99-7 ((1E,3E)-3-methyl-1,3-pentadien-1-yl)benzene 
• 814-75-5 3-bromo-butanone 
• 862167-35-9 (Z)-N-(4-methoxyphenyl)-6-methyloct-6-en-4-ynamide 

Relevant articles and documents

PALLADIUM-CATALYZED DIASTEREOSELECTIVE SYNTHESES OF (E)-1-TRIMETHYLSILYL-2-ALKENES, (E)-1-TRIMETHYLSILYL-1-ALKEN-3-YNES, (1E,5E)-1-TRIMETHYLSILYL-1,5-ALKADIEN-3-YNES, (1E,3Z)- AND (1E,3E)-1-TRIMETHYLSILYL-1,3-ALKADIENES

On the basis of our observation that (E)-1-bromo-1-alkenes undergo preferentially stereospecific Pd-catalyzed cross-couplings with a variety of organometallics, in the presence of the corresponding (Z)-stereoisomers, efficient and convenient diastereoselective procedures have been developed to prepare nearly stereoisomerically pure (E)-1-trimethylsilyl-2-alkenes (4), (E)-1-trimethylsilyl-1-alken-3-ynes (5), (1E,5E)-1-trimethylsilyl-1,5-alkadien-3-ynes (6), and (1E,3E)-1-trimethylsilyl-1,3-alkadienes (8) from stereoisomeric mixtures of alkenyl bromides.Compounds 5 have been stereoselectively converted into (1E,3Z)-1-trimethylsilyl-1,3-dienes (7) by selective hydrometallations, followed by hydrolysis.Some synthetic applications of compounds 5-8 have been also examined.