22037-73-6

Basic information

• Product Name: 3-BROMO-1-BUTENE
• Synonyms: 3-BROMO-1-BUTENE;1-Butene, 3-bromo-;1-butene,3-bromo-;3-bromo-but-1-ene;1-Methyl-2-propenyl bromide;1-Methylallyl bromide
• CAS NO: 22037-73-6
• Molecular Formula: C₄H₇Br
• Molecular Weight: 135
• Mol File: 22037-73-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: -115.07°C (estimate)
• Boiling Point: 88.08°C (estimate)
• Flash Point: 7.2°C
• Appearance: /
• Density: 1.3260
• Vapor Pressure: 68.2mmHg at 25°C
• Refractive Index: 1.4686
• CAS DataBase Reference: 3-BROMO-1-BUTENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-1-BUTENE(22037-73-6)
• EPA Substance Registry System: 3-BROMO-1-BUTENE(22037-73-6)

Safety Data

• Hazardous Substances Data: 22037-73-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C4H7Br/c1-3-4(2)5/h3-4H,1H2,2H3

Upstream product

• 504-61-0 (E)-but-2-enol 
• 598-32-3 2-hydroxy-3-butene 
• 106-99-0 buta-1,3-diene 
• 106-98-9 1-butylene 
• 590-18-1 (Z)-2-Butene 
• 4784-77-4 (E/Z)-crotyl bromide 
• 110-86-1 pyridine 
• 10035-10-6 hydrogen bromide 
• 7789-60-8 phosphorus tribromide 
• 7726-95-6 bromine 
• 113984-37-5 2-((E)-But-2-enyl)-1,3-diisopropyl-isourea 
• 18269-32-4 crotyl alcohol trimethylsilyl ether 
• 624-64-6 trans-2-Butene 
• 6117-91-5 (E/Z)-2-buten-1-ol 

Downstream Products

• 23086-43-3 4-hexen-1-ylbenzene 
• 106-98-9 1-butylene 
• 107-01-7 butene-2 
• 1569-59-1 3-methylpent-4-en-2-ol 
• 760-20-3 3-methyl-1-pentene 
• 4974-27-0 2,6-octadiene 
• 4894-62-6 3-methylhepta-1,5-diene 
• 592-43-8 2-hexene 
• 80188-12-1 2-methyl-N-phenylbut-3-enamide 
• 4784-77-4 (E/Z)-crotyl bromide 
• 5408-86-6 2,3-dibromobutane 
• 107-80-2 1,3-dibromobutane 
• 4784-77-4 (E)-1-Bromo-2-butene 
• 590-18-1 (Z)-2-Butene 

Relevant articles and documents

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ELECTROPHILIC SUBSTITUTION OF STRUCTURALLY RIGID n1-ALLYLPALLADIUM COMPLEXES

h1-Allyl(aryl)palladium complexes react with some electrophiles to result in the selective Pd-allyl bond cleavage with 1,3-transposition, while the corresponding η3-allyl(aryl)palladiums and the electrophiles give rise to the selective Pd-Ar bond cleavage.The η1-allyl complexes also react with CCl4 and CHCl3 under very mild conditions to give good yields of CH2=CHCHR(CR'Cl2) (R=H, Me; R'=Cl, H).

A mild method for the replacement of a hydroxyl group by halogen: 3. the dichotomous behavior of α-haloenamines towards allylic and propargylic alcohols

A study of the deoxyhalogenation of allylic and propargylic alcohols with tetramethyl-α-halo-enamines is reported. Primary allylic and primary and secondary propargylic alcohols gave the corresponding halides in high yields. Secondary allylic and propargylic alcohols yielded the corresponding secondary halides but the reaction also produced some rearranged primary halides (I > Br > Cl). The reactions with tertiary allylic and tertiary propargylic alcohols gave several products and was therefore of little synthetic value. However, the addition of triethylamine to the reaction mixture or the use of lithium alkoxide instead of alcohol brought about a major change of the course of the reaction which led to amides carrying an allyl or an allenyl group at C2. This was shown to result from a Claisen-Eschenmoser rearrangement of an intermediate α-allyloxy- or propargyloxy-enamine.

SYNTHESIS OF ALKYL HALIDES UNDER NEUTRAL CONDITIONS

Primary and secondary alcohols are efficiently converted to the corresponding alkyl halides under neutral conditions.

CONVERSION OF ALCOHOLS INTO ALKYL BROMIDES AND IODINES VIA O-ALKYLISOUREAS

Treatment of O-alkylisoureas with trifluoromethanesulphonic acid and a tetrabutylammonium salt (bromide or iodide) affords alkyl halides in high yields.