2,3-Dibromosuccinic Acid
Title: 2,3-Dibromosuccinic Acid
CAS Registry Number: 526-78-3
CAS Name: 2,3-Dibromobutanedioic acid
Additional Names: a,-dibromosuccinic acid; sym-dibromosuccinic acid
Molecular Formula: C4H4Br2O4
Molecular Weight: 275.88
Percent Composition: C 17.41%, H 1.46%, Br 57.93%, O 23.20%
Literature References: Prepn of dl-form by bromination of maleic acid: McKenzie, J. Chem. Soc. 101, 1196 (1912); Young et al., J. Am. Chem. Soc. 61, 1640 (1939); of meso-form by bromination of fumaric acid: eidem, ibid.; Rhinesmith, Org. Synth. coll. vol. II, 177 (1943). Resolution of dl-form: McKenzie, loc. cit.
 
Derivative Type: dl-Form
Additional Names: threo-2,3-Dibromosuccinic acid
Properties: Crystals, mp 167°. Very sol in cold water.
Melting point: mp 167°
 
Derivative Type: d-Form
Properties: Crystalline powder from ethyl acetate + CCl4, mp 157-158°. [a]D18 +64.4° (c = 5 in water), +135.8° (c = 5 in alc), +147.8° (c = 5 in ethyl acetate).
Melting point: mp 157-158°
Optical Rotation: [a]D18 +64.4° (c = 5 in water), +135.8° (c = 5 in alc), +147.8° (c = 5 in ethyl acetate)
 
Derivative Type: l-Form
Properties: Needles from benzene, decomp 157-158°. [a]D13 -148.0° (c = 5.8 in ethyl acetate). Very sol in cold water; sol in ethyl acetate, acetone, methanol, ethanol; sparingly sol in chloroform, petr ether, CCl4.
Optical Rotation: [a]D13 -148.0° (c = 5.8 in ethyl acetate)
 
Derivative Type: meso-Form
Additional Names: erythro-2,3-Dibromosuccinic acid
Properties: Cryst from water, dec 255-256°, also reported as mp 270-273°. Sol in 50 parts cold water, more sol in hot water; sol in alcohol, ether; sparingly sol in chloroform.
Melting point: mp 270-273°

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