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24347-58-8 - (2R,3R)-(-)-2,3-Butanediol, 98% - D-(-)-2,3-Butanediol - L06586 - Alfa Aesar

L06586 (2R,3R)-(-)-2,3-Butanediol, 98%

CAS Number
24347-58-8
Synonyms
D-(-)-2,3-Butanediol

Size Price ($) Quantity Availability
1g 49.75
5g 192.61
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(2R,3R)-(-)-2,3-Butanediol, 98%

MDL
MFCD00064267
EINECS
246-186-9

Chemical Properties

Formula
C4H10O2
Formula Weight
90.12
Melting point
16°
Boiling Point
179-180°
Flash Point
85°(185°F)
Density
0.988
Refractive Index
1.4315
Sensitivity
Hygroscopic
Solubility
Fully miscible in water.

Applications

(2R,3R)-(-)-2,3-Butanediol is used as a chiral auxiliary, chiral ligand and building block. Cyclocondenses with ketones for (13)C NMR determination of optical purity. It is used in the resolution of carbonyl compounds in gas chromatography.

Notes

Hygroscopic. Store away from oxidizing agents. Incompatible with oxidizing agents, Acid chlorides, Acid anhydrides, Chloroformates, Reducing agents. Air sensitive.

Literature References

James A. Marshall; Shiping Xie. Synthesis of a C22-34 Subunit of the Immunosuppressant FK-506.J. Org. Chem.1995,60 (22), 7230-7237.

Mark J. Burk; John E. Feaster; William A. Nugent; Richard L. Harlow. Preparation and use of C2-symmetric bis(phospholanes): production of .alpha.-amino acid derivatives via highly enantioselective hydrogenation reactions.J. Am. Chem. Soc.1993,115 (22), 10125-10138.

Forms cyclic acetals with aldehydes, which have been used in an enantioselective Lewis acid catalyzed aldol condensation: J. Am. Chem. Soc., 104, 7371,7372 (1982); Tetrahedron, 40, 4685 (1984):

Similarly, acetals react with Li organocuprates in the presence BF3 etherate to give only one of the two possible enantiomeric ethers: Tetrahedron, 45, 507 (1989):

Has been used for the resolution and determination of enantiomeric excess of chiral ketones by formation of the cyclic acetal and 13C-NMR: Tetrahedron Lett., 2183 (1977); J. Am. Chem. Soc., 109, 1363 (1987).

With boronic acids forms cyclic boronates, useful in asymmetric syntheses; reviews: Acc. Chem. Res., 21, 294 (1988); Tetrahedron, 45, 1859 (1989). See Appendix 5.

GHS Hazard and Precautionary Statements

Hazard Statements: H227

Combustible liquid.

Precautionary Statements: P210-P280-P370+P378a-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. In case of fire: Use for extinction: CO2, powder or water spray. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,1568
Beilstein
4290593
Harmonized Tariff Code
2905.39
TSCA
No

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