(2R,3R)-butane-2,3-diol

• ChemBase ID: 151261
• Molecular Formular: C4H10O2
• Molecular Mass: 90.121
• Monoisotopic Mass: 90.06807956
• SMILES: C[C@H]([C@@H](C)O)O
• Canonical SMILES: C[C@H]([C@H](O)C)O
• InChI: InChI=1S/C4H10O2/c1-3(5)4(2)6/h3-6H,1-2H3/t3-,4-/m1/s1
• InChIKey: OWBTYPJTUOEWEK-QWWZWVQMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-butane-2,3-diol
• IUPAC Traditional name: (R,R)-butane-2,3-diol
• Synonyms: (2R,3R)-(-)-2,3-Butanediol; D-(-)-2,3-Butanediol; (R,R)-2,3-Butanediol; D-(-)-2,3-Butanediol; (2R,3R)-Butane-2,3-diol; (2R,3R)-(-)-2,3-丁二醇; (R,R)-2,3-丁二醇; D-(-)-2,3-丁二醇

Database IDs

• CAS Number: 24347-58-8
• EC Number: 246-186-9
• MDL Number: MFCD00064267
• Beilstein Number: 1718901; 4290593
• Merck Index: 141568
• PubChem SID: 24854259; 162245417
• PubChem CID: 225936

CALCULATED PROPERTIES

• Acid pKa: 14.224482
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.37552902
• LogD (pH = 7.4): -0.3755291
• Log P: -0.37552902
• Molar Refractivity: 23.3912 cm^3
• Polarizability: 9.358869 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 16°C
• Boiling Point: 177-179 °C(lit.); 179-180°C; 77.3-77.4 °C/10 mmHg(lit.)
• Flash Point: 185 °F; 85 °C; 85°C(185°F)
• Density: 0.987 g/mL at 25 °C(lit.); 0.988; 0.992 g/mL at 20 °C(lit.)
• Refractive Index: 1.4315; n20/D 1.433; n20/D 1.433(lit.)
• Optical Rotation: [α]20/D -13±1°, neat; [α]23/D -13.2°, neat; -13 (neat)

Safety Information

• Storage Warning: Hygroscopic
• German water hazard class: 3
• TSCA Listed: 否
• GHS Hazard statements: H227
• GHS Precautionary statements: P210-P280-P370+P378A-P403+P235-P501A
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: -20°C

Product Information

• Purity: ≥96.0% (sum of enantiomers, GC); 97%; 98%
• Grade: purum
• Optical Purity: ee: 99% (GLC); enantiomeric ratio: ~98:2 (GC)
• Linear Formula: CH3CH(OH)CH(OH)CH3
• Empirical Formula (Hill Notation): C4H10O2

DETAILS

Sigma Aldrich - 237639

Packaging
1, 5 g in glass bottle
Application
C2 symmetric chiral diol with versatile applications as a chiral auxiliary,1,2 building block,3,4,5 and chiral ligand.6,7 Cyclocondenses with ketones8 for 13C NMR determination of optical purity.9,10
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 237639.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 18965

Other Notes
Chiral diol; used for determining the enantiomeric purity of ketones by acetal formation and 13C-NMR1,2; or chromatography3; Resolution of ketones4; Determination of enantiomeric purity of lactones by ortho esterification and GC5

REFERENCES

• 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.
• 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):