1947-58-6

Basic information

• Product Name: 2,3-Dibromo-1,4-butanediol
• Synonyms: 2,3-dibromobutane-1,4-diol;2,3-DibroMo-1,4-butanediol;(2R,3R)-rel-2,3-Dibromobutane-1,4-diol;1,4-BUTANEDIOL, 2,3-DIBROMO-, (+,-)-;1,4-Butanediol, 2,3-dibromo-, (R*,R*)-(.+/-.)-;1,4-Butanediol, d,l-2,3-dibromo-;2,3-dibromo-,(+,-)-4-butanediol;d,l-2,3-dibromo-4-butanediol
• CAS NO: 1947-58-6
• Molecular Formula: C₄H₈Br₂O₂
• Molecular Weight: 247.91
• EINECS: 217-750-1
• Product Categories: Alcohols;Monomers;Polymer Science;Organic Building Blocks;Oxygen Compounds;Polyols
• Mol File: 1947-58-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 88-90 °C(lit.)
• Boiling Point: 148-150 °C1.5 mm Hg(lit.)
• Flash Point: 156.6 °C
• Appearance: /
• Density: 2.124 g/cm³
• Vapor Pressure: 3.73E-05mmHg at 25°C
• Refractive Index: 1.583
• PKA: 13.40±0.10(Predicted)
• CAS DataBase Reference: 2,3-Dibromo-1,4-butanediol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dibromo-1,4-butanediol(1947-58-6)
• EPA Substance Registry System: 2,3-Dibromo-1,4-butanediol(1947-58-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: EK1575000
• Hazardous Substances Data: 1947-58-6(Hazardous Substances Data)

Usage

Chemical Properties

White solid

InChI:InChI=1/C4H8Br2O2/c5-3(1-7)4(6)2-8/h3-4,7-8H,1-2H2

Synthetic route

1,4-butenediol (6117-80-2) → dl-2,3-dibromo-1,4-butanediol (1947-58-6)

Conditions	Yield
With 1,1'-(ethane-1,2-diyl)dipyridinium bistribromide at 20℃; for 0.416667h;	91%
With diethyl ether; bromine
With dichloromethane; bromine
With hydrogen bromide; bromine
With bromine In dichloromethane Irradiation;

(5S,6S)-5,6-Dibromo-2,2-dimethyl-[1,3]dioxepane → dl-2,3-dibromo-1,4-butanediol (1947-58-6)

Conditions	Yield
With sodium benzenesulfonate In N,N-dimethyl-formamide at 60℃; for 3h;	90%

(+-)-5r,6t-dibromo-<1,3>dioxepane → dl-2,3-dibromo-1,4-butanediol (1947-58-6)

Conditions	Yield
With hydrogenchloride; methanol

1,4-butenediol (6117-80-2) + bromine (7726-95-6) → dl-2,3-dibromo-1,4-butanediol (1947-58-6)

3,4-dihydro-2H-pyran (110-87-2) + dl-2,3-dibromo-1,4-butanediol (1947-58-6) → treo-2,3-dibromo-1,4-tetrahydropyranyloxybutane

Conditions	Yield
With hydrogen cation	100%

dl-2,3-dibromo-1,4-butanediol (1947-58-6) + sodium thiophenolate (930-69-8) → racem.-2,3-bis-phenylsulfanyl-butane-1,4-diol (101431-43-0)

dl-2,3-dibromo-1,4-butanediol (1947-58-6) → racem.-2,3-dibromo-1,4-bis-nitryloxy-butane (89033-75-0)

Conditions	Yield
With sulfuric acid; nitric acid at -20℃;

dl-2,3-dibromo-1,4-butanediol (1947-58-6) → rac-1,2,3,4-diepoxybutane (1464-53-5)

Conditions	Yield
With potassium hydroxide

dl-2,3-dibromo-1,4-butanediol (1947-58-6) + aniline (62-53-3) → racem.-2,3-dianilino-butane-1,4-diol

succinic acid anhydride (108-30-5) + dl-2,3-dibromo-1,4-butanediol (1947-58-6) → succinic acid 1,1'-((RS,RS)-2,3-dibromo-butane-1,4-diyl) ester (107927-78-6, 124320-06-5)

Conditions	Yield
With pyridine

dl-2,3-dibromo-1,4-butanediol (1947-58-6) → 1,4-butenediol (6117-80-2) + (E)-2-butene-1,4-diol (821-11-4)

Conditions	Yield
With samarium In methanol for 1h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Upstream product

• 6117-80-2 1,4-butenediol 
• 7726-95-6 bromine 
• 107927-78-6 succinic acid 1,1'-((RS,RS)-2,3-dibromo-butane-1,4-diyl) ester 

Downstream Products

• 1464-53-5 rac-1,2,3,4-diepoxybutane 
• 6117-80-2 1,4-butenediol 
• 821-11-4 trans-butene-1,4-diol 

Relevant articles and documents

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Nickel mdiated Double Bond formation from vic-Dibromides and Ethyl Magnesium Bromide

vic-dibromides are quantitaively converted into alkenes by using a catalityc amount of NidppeCl2 in the presence of two molar equivalents of EtMgBr in THF.Stereochemical aspects of the reaction are given.