533-98-2

Basic information

• Product Name: 1,2-Dibromobutane
• Synonyms: 1,2-DIBROMOBUTANE;1,2-BUTYLENE BROMIDE;ALPHA-BUTYLENE BROMIDE;1,2-Dibrombutan;1,2-dibromo-butan;alpha-Butylene dibromide;butane,1,2-dibromo-;α-butylenedibromide
• CAS NO: 533-98-2
• Molecular Formula: C₄H₈Br₂
• Molecular Weight: 215.91
• EINECS: 208-581-4
• Product Categories: Alkyl;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 533-98-2.mol
• Article Data: 12

Chemical Properties

• Melting Point: -65°C
• Boiling Point: 59-60 °C (20 mmHg)
• Flash Point: >110°C
• Appearance: slightly yellow liquid
• Density: 1.789 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.51mmHg at 25°C
• Refractive Index: 1.513-1.515
• Solubility: alcohol: miscible(lit.)
• Merck: 14,1566
• BRN: 1731380
• CAS DataBase Reference: 1,2-Dibromobutane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Dibromobutane(533-98-2)
• EPA Substance Registry System: 1,2-Dibromobutane(533-98-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/38-36/37/38-20/21/22
• Safety Statements: 37/39-26
• RIDADR: 2810
• WGK Germany: 3
• TSCA: T
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 533-98-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 3116, 1983 DOI: 10.1021/jo00166a041

General Description

Mechanism of Co(II) (N,N′-disalicylidene-ethylenediamine) catalyzed reduction of 1,2-dibromobutane in DMF has been investigated by microelectrode voltammetry.

InChI:InChI=1/C4H8Br2/c1-2-4(6)3-5/h4H,2-3H2,1H3

Upstream product

• 106-98-9 1-butylene 
• 107-00-6 but-1-yne 
• 78-76-2 s-butyl bromide 
• 67-56-1 methanol 
• 616-27-3 1-chlorobutan-2-one 
• 109-65-9 1-bromo-butane 
• 7726-95-6 bromine 
• 533-98-2 1,2-dibromobutane 
• 26256-82-6 (S)-2-bromo-butan-1-ol 
• 106-97-8 n-butane 
• 109-69-3 n-Butyl chloride 
• 593-71-5 Chloroiodomethane 
• 123-38-6 propionaldehyde 
• 592-34-7 carbonochloridic acid, butyl ester 

Downstream Products

• 23074-36-4 2-bromobutene 
• 13814-27-2 1,2-butanediol diacetate 
• 106-98-9 1-butylene 
• 5408-86-6 2,3-dibromobutane 
• 584-03-2 1,2-dihydroxybutane 
• 4426-48-6 1,2-butanediamine 
• 3195-86-6 2-ethylthiirane 
• 78186-85-3 4-ethyl ethylene trithiocarbonate 
• 31844-98-1 (E)/(Z)-1-bromo-1-butene 
• 107-00-6 but-1-yne 
• 533-98-2 (S)-1,2-dibromobutane 
• 4096-21-3 N-phenylpyrrolidine 
• 1679-36-3 3-hexyn-2-one 
• 710351-70-5 1-(2-methyl-5-nitrophenyl)pyrrolidine 

Relevant articles and documents

Induced Fitting and Polarization of a Bromine Molecule in an Electrophilic Inorganic Molecular Cavity and Its Bromination Reactivity

Dodecavanadate, [V12O32]4? (V12), possesses a 4.4 ? cavity entrance, and the cavity shows unique electrophilicity. Owing to the high polarizability, Br2 was inserted into V12, inducing the inversion of one of the VO5 square pyramids to form [V12O32(Br2)]4? (V12(Br2)). The inserted Br2 molecule was polarized and showed a peak at 185 cm?1 in the IR spectrum. The reaction of V12(Br2) and toluene yielded bromination of toluene at the ring, showing the electrophilicity of the inserted Br2 molecule. Compound V12(Br2) also reacted with propane, n-butane, and n-pentane to give brominated alkanes. Bromination with V12(Br2) showed high selectivity for 3-bromopentane (64 %) among the monobromopentane products and preferred threo isomer among 2-,3-dibromobutane and 2,3-dibromopenane. The unique inorganic cavity traps Br2 leading the polarization of the diatomic molecule. Owing to its new reaction field, the trapped Br2 shows selective functionalization of alkanes.

Enantioselectivity of haloalkane dehalogenases and its modulation by surface loop engineering

In the loop: Engineering of the surface loop in haloalkane dehalogenases affects their enantiodiscrimination behavior. The temperature dependence of the enantioselectivity (lnE versus 1/T) of β-bromoalkanes by haloalkane dehalogenases is reversed (red data points) by deletion of the surface loop; the selectivity switches back when an additional single-point mutation is made. This behavior is not observed for -bromoesters.

Bromochlorination of Alkenes with Dichlorobromate (1-) ion. IV. Regiochemistry of Bromochlorinations of Alkenes with Molecular Bromine Chloride and Dichlorobromate (1-) Ion

The regioselectivity of the addition of molecular bromine chloride to alkenes is dependent on both the steric and electronic effects of the alkyl substituent.In contrast, the regioselectivity of the addition of dichlorobromate (1-) ion to alkenes is controlled mainly by the steric effect of the substituent.