1947-58-6

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

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

Downstream Products

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

Relevant academic research and scientific papers

A new recyclable ditribromide reagent for efficient bromination under solvent free condition

1,2-Dipyridiniumditribromide-ethane (DPTBE) has been synthesized and explored as a new efficient brominating agent. The crystalline ditribromide reagent is stable for months and acts as a safe source of bromine requiring just 0.5 equiv for complete bromination. It has high active bromine content per molecule and shows a remarkable reactivity compared to other tribromide reagents toward various substrates by just grinding the reagent and substrates in a porcelain mortar at room temperature. No organic solvent has been used during any stage of the reaction for substrates giving product as solid. Product can easily be isolated by just washing the highly water soluble 1,2- dipyridiniumdibromide-ethane (DPDBE) from the brominated product. The spent reagent can be recovered, regenerated, and reused without any significant loss.

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.