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

• ChemBase编号: 151261
• 分子式: C4H10O2
• 平均质量: 90.121
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (2R,3R)-butane-2,3-diol
• IUPAC传统名: (R,R)-butane-2,3-diol
• 别名: (2R,3R)-(-)-2,3-丁二醇; (R,R)-2,3-丁二醇; D-(-)-2,3-丁二醇; (2R,3R)-(-)-2,3-Butanediol; D-(-)-2,3-Butanediol; (R,R)-2,3-Butanediol; D-(-)-2,3-Butanediol; (2R,3R)-Butane-2,3-diol

登记号

• CAS号: 24347-58-8
• EC号: 246-186-9
• MDL号: MFCD00064267
• Beilstein号: 4290593; 1718901
• 默克索引号: 141568
• PubChem SID: 24854259; 162245417
• PubChem CID: 225936

理论计算性质

• Acid pKa: 14.224482
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): -0.37552902
• LogD (pH = 7.4): -0.3755291
• Log P: -0.37552902
• 摩尔折射率: 23.3912 cm^3
• 极化性: 9.358869 Å^3
• 极化表面积: 40.46 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 16°C
• 沸点: 177-179 °C(lit.); 179-180°C; 77.3-77.4 °C/10 mmHg(lit.)
• 闪点: 185 °F; 85 °C; 85°C(185°F)
• 密度: 0.987 g/mL at 25 °C(lit.); 0.988; 0.992 g/mL at 20 °C(lit.)
• 折射率: 1.4315; n20/D 1.433; n20/D 1.433(lit.)
• 比旋光度: [α]20/D -13±1°, neat; [α]23/D -13.2°, neat; -13 (neat)

安全信息

• 保存注意事项: Hygroscopic
• 德国WGK号: 3
• TSCA收录: 否
• GHS危险声明: H227
• GHS警示性声明: P210-P280-P370+P378A-P403+P235-P501A
• 个人保护装置: 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)
• 保存温度: -20°C

产品相关信息

• 纯度: ≥96.0% (sum of enantiomers, GC); 97%; 98%
• 级别: purum
• 光学纯度: ee: 99% (GLC); enantiomeric ratio: ~98:2 (GC)
• 线性分子式: CH3CH(OH)CH(OH)CH3
• Empirical Formula (Hill Notation): C4H10O2

详细说明

Sigma Aldrich - 237639

包装
1, 5 g in glass bottle
Application
C2 对称手性二醇，具有多种用途如手性辅助剂、1,2结构单元、3,4,5和手性配体。6,7与酮发生环缩合反应8以用于 13C NMR 光学纯度测定。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
手性二醇；用于通过乙缩醛的形成和 13C-NMR1,2 测定酮的对映体纯度；或用于色谱分析3；用于酮的拆分4；用于通过邻位酯化反应和气相色谱法测定内酯的对映体纯度5

参考文献

• 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):