3234-02-4

Basic information

• Product Name: trans-2,3-Dibromo-2-butene-1,4-diol
• Synonyms: 2,3-dibromo-2-butene-4-diol;4-diol,2,3-dibromo-2-Butene-1;TRANS-2,3-DIBROMO-1,4-DIHYDROXY-2-BUTENE;TRANS-2,3-DIBROMO-2-BUTENE-1,4-DIOL;TRANS-2,3-DIBROMO-2-BUTEN-1,4-DIOL;DBD;DIBROMO(-2,3)-2-BUTENE-1,4-DIOL;2,3-DIBROMO-2-BUTENE-1,4-DIOL
• CAS NO: 3234-02-4
• Molecular Formula: C₄H₆Br₂O₂
• Molecular Weight: 245.9
• EINECS: 221-779-5
• Product Categories: Alcohols;Monomers;Polymer Science
• Mol File: 3234-02-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 112-114 °C(lit.)
• Boiling Point: 318.1 °C at 760 mmHg
• Flash Point: 146.2 °C
• Appearance: /
• Density: 1.9671 (rough estimate)
• Vapor Pressure: 3.07E-05mmHg at 25°C
• Refractive Index: 1.5230 (estimate)
• PKA: 11.91±0.10(Predicted)
• Water Solubility: 1-5 g/100 mL at 21 ºC
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: trans-2,3-Dibromo-2-butene-1,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: trans-2,3-Dibromo-2-butene-1,4-diol(3234-02-4)
• EPA Substance Registry System: trans-2,3-Dibromo-2-butene-1,4-diol(3234-02-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: EM6910000
• Hazardous Substances Data: 3234-02-4(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

General Description

Crystals or white powder.

Air & Water Reactions

Water soluble.

Reactivity Profile

A halogenated alkene and alcohol. The unsaturated aliphatic hydrocarbons are generally much more reactive than the alkanes, which are saturated aliphatic hydrocarbons. Strong oxidizers may react vigorously with them. Reducing agents can react exothermically to release gaseous hydrogen. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.

Fire Hazard

Flash point data for trans-2,3-Dibromo-2-butene-1,4-diol are not available, however trans-2,3-Dibromo-2-butene-1,4-diol is probably combustible.

InChI:InChI=1/C4H6Br2O2/c5-3(1-7)4(6)2-8/h7-8H,1-2H2

Synthetic route

1,4-dihydroxybut-2-yne (110-65-6) → 2,3-dibromo-but-2-ene-1,4-diol (3234-02-4)

Conditions	Yield
With tetraethylammonium bromide; bromine In dichloromethane at 20 - 30℃; for 8h; Green chemistry;	95%
With hexamethonium bis(tribromide) In neat (no solvent) for 0.333333h; Green chemistry; regioselective reaction;	88%
With tetrabutylammomium bromide; dihydrogen peroxide; vanadia In water; acetonitrile at 5℃; for 1.5h; Bromination;	46%

diacetyl compound of 2.3-dibromo-butene-(2)-diol-(1.4) → 2,3-dibromo-but-2-ene-1,4-diol (3234-02-4)

Conditions	Yield
With sodium ethanolate

2,3-dibromo-but-2-ene-1,4-diol (3234-02-4) → 3,4-dibromofuran (32460-02-9)

Conditions	Yield
With potassium dichromate; sulfuric acid In hexane; water at 85℃; for 6h; Heating;	83%
With potassium dichromate; sulfuric acid In water at 140℃; for 4h;	56%

2,3-dibromo-but-2-ene-1,4-diol (3234-02-4) → 1,4-dihydroxybut-2-yne (110-65-6)

Conditions	Yield
With ethanol; zinc

2,3-dibromo-but-2-ene-1,4-diol (3234-02-4) + acetyl chloride (75-36-5) → 1,4-diacetoxy-2,3-dibromo-but-2-ene (63766-44-9)

ethanol (64-17-5) + 2,3-dibromo-but-2-ene-1,4-diol (3234-02-4) + zinc → 1,4-dihydroxybut-2-yne (110-65-6)

2,3-dibromo-but-2-ene-1,4-diol (3234-02-4) + propyl bromide (106-94-5) → 2,3-dibromo-4-propoxybut-2-en-1-ol

Conditions	Yield
With sodium hydroxide In water; toluene at 70 - 72℃; for 4h;	42.5 g

Upstream product

• 110-65-6 1,4-dihydroxybut-2-yne 

Downstream Products

• 110-65-6 1,4-dihydroxybut-2-yne 
• 32460-02-9 3,4-dibromofuran 

Relevant articles and documents

A 2, 3 - dibromo - 1, 4 - butylene diol synthesis method

The invention discloses a 2, 3 - dibromo - 1, 4 - butylene diol synthesis method, solves the technical 2, 3 - dibromo - 1, 4 - butylene glycol of complex synthesis method, harsh reaction conditions not security, and the parameter is not easy to control, the production cost is high, poor quality of the products, the technical problem to limit its use. The invention discloses a 2, 3 - dibromo - 1, 4 - butylene diol synthesis method, comprises the following steps: 1) in dichloromethane solvent, after adding catalyst ammonium bromide, [...] while stirring, to obtain the brominating agent ammonium bromide complex bromide; 2) in dichloromethane solvent, adding butynediol with the step 1) of ammonium bromide complex prepared by brominating electrophilic addition reaction of bromide occurs, generating a 2, 3 - dibromo - 1, 4 - butylene glycol; water washing, cooling, so that the 2, 3 - dibromo - 1, 4 - butylene glycol crystallization, after filtering, a 2, 3 - dibromo - 1, 4 - butylene glycol crude; 3) purification of 2, 3 - dibromo - 1, 4 - butylene glycol crude product. The invention can be widely applied to the technical field of chemical synthesis.

Hexamethonium bis(tribromide) (HMBTB) a recyclable and high bromine containing reagent

A recyclable and high bromine containing di-(tribromide) reagent, hexamethonium bis(tribromide) (HMBTB) has been synthesized and utilized for the bromination of various organic substrates. The spent reagent hexamethonium bromide (HMB) can be effectively recycled by regenerating and reusing it without significant loss of activity. The crystalline and stable bis(tribromide) is an effective storehouse of very high percentage of active bromine requiring just half an equivalent of it for complete bromination. Both the Br3- moieties in HMBTB are nearly linear with Br-Br-Br angle of 179.55°.

Regioselective bromination of organic substrates by tetrabutylammonium bromide promoted by V2O5-H2O2: An environmentally favorable synthetic protocol

(matrix presented) Vanadium pentoxide very effectively promotes the bromination of organic substrates, including selective bromination of some aromatics, by tetrabutylammonium bromide in the presence of hydrogen peroxide; mild conditions, high selectivity, yield, and reaction rate, and redundancy of bromine and hydrobromic acid are some of the major advantages of the synthetic protocol.