1,4-Dibromo-2,3-butanediol

Base Information

• Chemical Name: 1,4-Dibromo-2,3-butanediol
• CAS No.: 14396-65-7
• Molecular Formula: C4H8Br2O2
• Molecular Weight: 247.91
• Hs Code.: 2905590090
• European Community (EC) Number: 627-179-3
• NSC Number: 142325,241568
• DSSTox Substance ID: DTXSID20861852
• Nikkaji Number: J803.180K
• Mol file: 14396-65-7.mol

Synonyms:1,4-Dibromo-2,3-butanediol;14396-65-7;1,4-dibromobutane-2,3-diol;2,3-Butanediol, 1,4-dibromo-;299-70-7;19396-65-7;19953-61-8;Dibromo-L-(+)-threitol;1,4-Dibromo-2,3-dihydroxybutane;AI3-61923;WLN: E1YQYQ1E;NCIOpen2_004735;1,4-dideoxy-L-+-erythritol;SCHEMBL561011;(L)-(+)-1,3-butanediol;1,4-dibromo-butan-2,3-diol;dl-1,4-dibromo-2,3-butanediol;DTXSID20861852;NSC142325;NSC241568;AKOS015890553;NSC 142325;NSC-142325;NSC-241568;AS-59392;FT-0606846;FT-0637073;Threitol,4-dibromo-1,4-dideoxy-, L-(+)-;F87122;Erythritol,4-dibromo-1,4-dideoxy-, (O)-(+)-;J-007887

Chemical Property of 1,4-Dibromo-2,3-butanediol

Chemical Property:

• Vapor Pressure: 8.09E-07mmHg at 25°C
• Melting Point: 82-84 °C(lit.)
• Refractive Index: 1.583
• Boiling Point: 365.3 °C at 760 mmHg
• PKA: 12.49±0.20(Predicted)
• Flash Point: 174.7 °C
• PSA: 40.46000
• Density: 2.124 g/cm³
• LogP: 0.49800
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 247.88706
• Heavy Atom Count: 8
• Complexity: 52

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,4-Dibromo-2,3-butanediol 95% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C(C(CBr)O)O)Br
• Uses: 1,4-Dibromo-2,3-butanediol has been used in the preparation of diquaternary gemini surfactants.

Technology Process of 1,4-Dibromo-2,3-butanediol

There total 5 articles about 1,4-Dibromo-2,3-butanediol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

butanediamide (110-14-5) → 1,4-dibromo-2,3-dihydroxybutane (14396-65-7)

Guidance literature:

butanediamide; With 2-pyrrolidinon; at 7 ℃;

With bismuth(III) carbonate; hydrogen bromide; at 3 ℃; for 2.83333h; Temperature;

Reference yield:

D-threitol (2418-52-2,10030-58-7,188346-77-2,149-32-6) → (S,S)-1,4-dibromo-butane-2,3-diol (299-70-7,1947-59-7,14396-65-7,15410-44-3,24677-99-4)

Guidance literature:

With hydrogen bromide;

Reference yield:

threo-1,4-dibromo-2,3-butanediol (299-70-7) + 4-trifluoromethyl-phenyl acetyl chloride (329-15-7) → 4-Trifluoromethyl-benzoic acid (1S,2S)-3-bromo-1-bromomethyl-2-hydroxy-propyl ester + 4-Trifluoromethyl-benzoic acid (1R,2R)-3-bromo-1-bromomethyl-2-hydroxy-propyl ester + (S,S)-1,4-dibromo-butane-2,3-diol (299-70-7,1947-59-7,14396-65-7,15410-44-3,24677-99-4) + (2R,3R)-1,4-dibromobutane-2,3-diol (15410-44-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; (9S)-6'-methoxycinchonan-9-yl diphenylphosphinite; In various solvent(s); at -78 ℃; for 1h; Title compound not separated from byproducts;

DOI:10.1016/j.tetlet.2006.09.109

upstream raw materials:

butanediamide

D-threitol

(R,R)-butane-1,2:3,4-bisoxide

threo-1,4-dibromo-2,3-butanediol

Downstream raw materials:

treosulfan

Refernces

• 1、 Mizuta, Shinya,Ohtsubo, Yutaka,Tsuzuki, Takeo,Fujimoto, Tetsuya,Yamamoto, Iwao. "Kinetic resolution of d,l-1,2-diols catalyzed by amine-phosphinite bifunctional organocatalysis derived from quinidine". . p. 8227 - 8229. Retrieved 2007/10/03.