20038-12-4

Basic information

• Product Name: 3-Methyl-3-butenyl bromide
• Synonyms: 1-Bromo-3-methyl-3-butene;2-Methyl-4-bromo-1-butene;3-Methyl-3-butenyl bromide;4-Bromo-2-methyl-1-butene;1-Butene, 4-bromo-2-methyl-
• CAS NO: 20038-12-4
• Molecular Formula: C₅H₉Br
• Molecular Weight: 149.02896
• Mol File: 20038-12-4.mol
• Article Data: 26

Chemical Properties

• Melting Point: -106.7°C (estimate)
• Boiling Point: 125℃
• Flash Point: 26℃
• Appearance: /
• Density: 1.250
• Refractive Index: 1.4600
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-Methyl-3-butenyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-3-butenyl bromide(20038-12-4)
• EPA Substance Registry System: 3-Methyl-3-butenyl bromide(20038-12-4)

Safety Data

• Hazardous Substances Data: 20038-12-4(Hazardous Substances Data)

Usage

General Description

3-Methyl-3-butenyl bromide, also known as isopentenyl bromide, is a chemical compound with the molecular formula C5H9Br. It is a colorless liquid with a sharp, sweet odor, and is primarily used in organic synthesis as a reagent for the introduction of the isopentenyl group. It is a highly reactive alkylating agent that can undergo nucleophilic substitution reactions with nucleophiles such as amines and thiolates. It is also used as an intermediate in the synthesis of various pharmaceuticals and other organic compounds. Due to its highly reactive nature and potential health hazards, proper safety precautions should be taken when handling and using 3-Methyl-3-butenyl bromide.

Upstream product

• 763-32-6 2-methyl-1-buten-4-ol 
• 80352-66-5 4-mesyloxy-2-methylbutene 
• 781-03-3 isopentenyl tosylate 
• 1246996-36-0 C₈H₁₃Br 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 28322-39-6 2-Methyl-1-buten-triphenylphosphoniumbromid 
• 143008-65-5 2,4-dimethyl-3-(3-methyl-3-butenyl)-2-cyclohexen-1-one 
• 114838-13-0 3-<(1-methylethyl)thio>-1-(3-methyl-3-buten-1-yl)cyclohexa-2,5-diene-1-carboxylic acid 
• 73617-70-6 9-((8S,9R)-9-Benzyloxy-8-methyl-1,4,7-trioxa-spiro[4.6]undec-8-yl)-2,6-dimethyl-non-1-en-5-ol 
• 75463-14-8 1-Methyl-4-(1-methyl-cyclopropylmethanesulfonyl)-benzene 
• 208335-13-1 5-[Benzoyl-(3-methyl-but-3-enyl)-amino]-furan-2-carboxylic acid methyl ester 
• 208335-26-6 5-[[3-(3,4-Dimethoxy-phenyl)-propionyl]-(3-methyl-but-3-enyl)-amino]-furan-2-carboxylic acid methyl ester 
• 208335-24-4 5-[[2-(3,4-Dimethoxy-phenyl)-acetyl]-(3-methyl-but-3-enyl)-amino]-furan-2-carboxylic acid methyl ester 
• 231298-24-1 tert-butyl N-<3-(2-methylbutenyl)>-N-<2-(5-p-nitrophenyl)furyl>carbamate 
• 72128-68-8 6-methyl-1-phenylhept-6-en-3-one 
• 496808-23-2 4-[(E/Z)-1,5-dimethylhex-5-enylidene]-1-methylcyclohex-1-ene 
• 181874-83-9 3-(3-methylbut-3-enyl)-1-trimethylsilyloxylcyclohex-1-ene 
• 860438-01-3 (7S,8R,9S)-8-Benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxy)-10-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-1-en-5-ol 

Relevant articles and documents

A C10 Chiron Applicable to the Synthesis of Archaebacterial Lipids

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Theoretical elucidation of kinetic and thermodynamic control of radical addition regioselectivity

The cyclizations of two structurally similar 2-oxo-5-hexenyl-type radicals have been investigated by ab initio and density functional (UB3LYP/6-31+G**//UHF/6-31G* and UB3LYP/6-31G*//UB3LYP/6-31G*) calculations. The origin of apparently contradictory reports of 6-endo and 5-exo cyclizations is determined. Kinetic control favors 6-endo cyclization, while thermodynamic control gives 5-exo cyclization, and the observation of different products from different research groups arises from the difference in experimental conditions used by the two groups. The outcome of a new cyclization reaction was predicted by using these theoretical techniques. Kinetic control is predicted to yield exclusively the products of 6-endo cyclization, while thermodynamic control would lead to an approximately equal mixture of one 6-endo and one 5-exo cyclized product. Experimental studies revealed that the reaction yields only the products of 6-endo cyclization through kinetic control.

Cu-Catalyzed C-H Allylation of Benzimidazoles with Allenes

CuH-catalyzed intramolecular cyclization and intermolecular allylation of benzimidazoles with allenes have been described. The reaction proceeded smoothly with the catalytic system of Cu(OAc)2/Xantphos and catalytic amount of (MeO)2MeSiH. This protocol features mild reaction conditions and a good tolerance of substrates bearing electron-withdrawing, electron-donating, or electron-neutral groups. A new catalytic mechanism was proposed for this copper hydride catalytic system.

Hydroalkylation of Olefins to Form Quaternary Carbons

Metal-hydride hydrogen atom transfer (MHAT) functionalizes alkenes with predictable branched (Markovnikov) selectivity. The breadth of these transformations has been confined to π-radical traps; no sp3 electrophiles have been reported. Here we describe a Mn/Ni dual catalytic system that hydroalkylates unactivated olefins with unactivated alkyl halides, yielding aliphatic quaternary carbons.