5780-13-2

Basic information

• Product Name: 2,3-DIBROMOPENTANE
• Synonyms: (R*,S*)-2,3-dibromobutane;Butane, 2,3-dibromo-, erythro;butane,2,3-dibromo-,(R*,S*)-;butane,2,3-dibromo-,meso-;erythro-2,3-Dibromobutane;2,3-DIBROMOPENTANE;MESO-2,3-DIBROMOBUTANE;(2R,3S)-2,3-Dibromobutane
• CAS NO: 5780-13-2
• Molecular Formula: C₄H₈Br₂
• Molecular Weight: 229.94
• EINECS: 226-476-1
• Product Categories: Alkyl;Halogenated Hydrocarbons;Organic Building Blocks;Building Blocks;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 5780-13-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: -34.5°C
• Boiling Point: 91 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.671 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.02mmHg at 25°C
• Refractive Index: n20/D 1.508(lit.)
• CAS DataBase Reference: 2,3-DIBROMOPENTANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIBROMOPENTANE(5780-13-2)
• EPA Substance Registry System: 2,3-DIBROMOPENTANE(5780-13-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36
• Safety Statements: 26-36-37/39
• RIDADR: 2810
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 5780-13-2(Hazardous Substances Data)

Usage

Description

2,3-Dibromopentane, also known as meso-2,3-dibromobutane, is a dihaloalkane with two forms of rotational isomers: the trans and gauche isomer. It is characterized by its unique chemical structure and has been the subject of various studies, including investigations into its IR and Raman spectra, as well as its different conformations through NMR studies.

Uses

Used in Chemical Synthesis:
2,3-Dibromopentane is used as a synthetic intermediate for the production of haloalcohols, which are catalyzed by haloalkane dehalogenases. This application takes advantage of its unique dihaloalkane structure, allowing for the creation of valuable compounds in the chemical industry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3-dibromopentane can be utilized as a building block for the synthesis of various drugs and pharmaceutical compounds. Its unique chemical properties make it a versatile starting material for the development of new medications.
Used in Research and Development:
Due to its distinct chemical structure and the various studies conducted on its properties, 2,3-dibromopentane is also used in research and development for understanding the behavior of dihaloalkanes and their potential applications in various fields, including materials science and chemical engineering.

InChI:InChI=1/C4H8Br2/c1-3(5)4(2)6/h3-4H,1-2H3/t3-,4+

Upstream product

• 17998-02-6 meso 2,3-butanediol diacetate 
• 590-18-1 (Z)-2-Butene 
• 624-64-6 trans-2-Butene 
• 19246-45-8 threo-2-bromo-3-chlorobutane 
• 19246-45-8 erythro-2-bromo-3-chlorobutane 
• 78-76-2 s-butyl bromide 
• 1114-92-7 2,3-diacetoxybutane 
• 10035-10-6 hydrogen bromide 
• 64-19-7 acetic acid 
• 3017-68-3 (Z)-2-Bromo-2-butene 
• 3017-71-8 (E)-2-bromobut-2-ene 
• 7726-95-6 bromine 
• 503-17-3 dimethylacetylene 
• 2211-67-8 racemic 2,3-dichlorobutane 

Downstream Products

• 3017-71-8 (E)-2-bromobut-2-ene 
• 1114-92-7 2,3-diacetoxybutane 
• 590-18-1 (Z)-2-Butene 
• 624-64-6 trans-2-Butene 
• 4613-11-0 2,3-diphenylbutane 
• 3017-68-3 (Z)-2-Bromo-2-butene 
• 78-93-3 butanone 
• 5798-80-1 threo-3-bromo-2-butanol 
• 19246-39-0 3-bromo-2-butanol 
• 107-01-7 butene-2 

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.

Efficient Conversion of Alkyl Chlorides into Bromides

The convenient and selective catalytic conversion of secondary and tertiary alkyl chlorides into bromides with hydrogen bromide in the presence of small amounts of anhydrous iron(III) bromide is described.

Free Radical Substitution. Part 38. The Effect of Solvent on the Atomic Chlorination and Bromination of 2-Substituted Butanes and the Importance of Steric Effects

The relative selectivity of atomic halogenation of 2-substituted butanes is influenced by the phase and by solvents.There are solvents which increase the selectivity compared with the gas phase and solvents which decrease the relative selectivity.However the most striking feature of the halogenation (especially the bromination) of 2-substituted butanes is the high reactivity of the 2-position notwithstanding very unfavourable polar effects.This reactivity is attributed to the release of steric compression associated with the abstraction of the tertiary hydrogen atom.The halogenation of butan-2-ol esters is associated with some decomposition of 2-butyl radical (OCOR)CH3> and the chlorination of 2-phenylbutane with the formation of olefins 2-phenylbut -1-ene and 2-phenylbut-2-ene.