| Identification | More | [Name]
(2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester | [CAS]
13811-71-7 | [Synonyms]
(2S,3S)-(-)-DIETHYL TARTRATE
(2S,3S)(-)-DIHYDROXYBUTANE-1,4-DIOIC ACID DIETHYL ESTER
D-DET
D(-)-DIETHYL TARTRATE
DET
(-)-DIETHYL-2,3-DIHYDROXYSUCCINATE
(-)-DIETHYL-D-TARTRATE
DIETHYL D-(-)-TARTRATE
DIETHYL D-TARTRATE
D-(-)-TARTARIC ACID DIETHYL ESTER
ETHYL TARTRATE
[-]-TARTARIC ACID DIETHYL ESTER
dlethyl-tartrate
diethyl [S-(R*,R*)]-tartrate
D-tartrate
MINUS-TARTARIC ACID DIETHYL ESTER
DIETHYL D-TARTRATE, 99+%
D (-)Diethy tartrate
(-)-Diethyl D-tartrate, made from unnatural tartaric acid, 99%
Butanedioic acid, 2,3-dihydroxy-, diethyl ester, S-(R*,R*)- | [EINECS(EC#)]
237-458-8 | [Molecular Formula]
C8H14O6 | [MDL Number]
MFCD00064451 | [Molecular Weight]
206.19 | [MOL File]
13811-71-7.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless to light yellow liqui | [Melting point ]
17 °C
| [alpha ]
-9 º (neat) | [Boiling point ]
162 °C/19 mmHg (lit.) | [density ]
1.205 g/mL at 20 °C(lit.)
| [refractive index ]
n20/D 1.446(lit.)
| [Fp ]
200 °F
| [storage temp. ]
Store below +30°C. | [solubility ]
Chloroform (Slightly), Water (Slightly) | [form ]
Viscous Liquid | [pka]
11.61±0.20(Predicted) | [color ]
Clear colorless | [Specific Gravity]
1.21 | [Optical Rotation]
[α]23/D 8.5°, neat | [Water Solubility ]
insoluble | [Merck ]
3855 | [BRN ]
1727143 | [InChI]
1S/C8H14O6/c1-3-13-7(11)5(9)6(10)8(12)14-4-2/h5-6,9-10H,3-4H2,1-2H3/t5-,6-/m0/s1 | [InChIKey]
YSAVZVORKRDODB-WDSKDSINSA-N | [SMILES]
CCOC(=O)[C@@H](O)[C@H](O)C(=O)OCC | [CAS DataBase Reference]
13811-71-7(CAS DataBase Reference) | [NIST Chemistry Reference]
Butanedioic acid, 2,3-dihydroxy-, diethyl ester, [S-(R*,R*)]-(13811-71-7) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29181300 | [Storage Class]
10 - Combustible liquids |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless to light yellow liqui | [Uses]
Diethyl D(-)-tartrate is mainly used in chiral pharmaceuticals, chiral intermediates and chiral catalysts. It can be used with titanium in enolic asymmetric epoxidization. The compound d-alpha-tocopherol is the principal compound present in natural vitamin E sources. At present, d-alpha-tocopherol and other tocopherol derivatives are used in pharmaceuticals, foods and animal feeds. It is used as a food additive. | [Synthesis]
[Refining Procedure No. 1]: In a reactor equipped with a thermometer and a stirrer, 60.0 g of D-tartaric acid (containing 0.20% malic acid and 0.07% fumaric acid) and 36.0 g of ethanol were added, and stirred for 2 hr. at 10° C. The reaction was completed by filtration. After completion of the reaction, 48.1 g of D-tartaric acid was recovered by filtration. [Method 1]: [1st refining step] Dried D-tartaric acid was mixed with 28.8 g of ethanol, 1.9 g of 35% hydrochloric acid was added, and the reaction was carried out at 80°C. Subsequently, the same amount of ethanol and 35% hydrochloric acid was added again at 70 °C, and the reaction was concentrated. The moisture content was confirmed to be 0.1% by weight, and the first esterification reaction solution was obtained. [Method 2]: Ethanol was added to the first esterification reaction solution for stirring, and then 11.4 g of thionyl chloride was added, and the reaction was carried out at 30-40 °C. The reaction was concentrated after completion to obtain the second esterification reaction solution. [Method 3]: Sodium bicarbonate was added to the second esterification reaction solution, and the filtrate was filtered after the reaction to obtain the filtrate (diethyl D-tartrate, 97% yield). Finally, diethyl D-(-)-tartaric acid with an optical purity of 99.8% ee was isolated by film distillation (hot medium temperature 145 °C) under reduced pressure, with diethyl malate and diethyl fumarate contents of less than 0.01%. In addition, the contents of diethyl sulfite and monoethyl tartrate were less than 0.01% and 0.02%, respectively. | [Purification Methods]
Distil the esters under high vacuum and store them under vacuum or in an inert atmosphere in a desiccator in round bottomed flasks equiped with a vacuum stopcock. They have also been distilled by Kügelrohr distillation and/or by 'wiped-film' molecular distillation. They are slightly soluble in H2O but miscible with EtOH and Et2O. [Gao et al. J Am Chem Soc 109 5770 (5771) 1987, IR: Pristera Anal Chem 25 844 1953, Beilstein 3 III 1025 for D-(-), 3 IV 1232 for L(+).] | [References]
[1] Tetrahedron, 2007, vol. 63, # 27, p. 6346 - 6357
[2] Tetrahedron Asymmetry, 2011, vol. 22, # 3, p. 257 - 263
[3] RSC Advances, 2014, vol. 4, # 90, p. 48827 - 48835
[4] RSC Advances, 2013, vol. 3, # 43, p. 20298 - 20307
[5] Patent: CN104003883, 2016, B. Location in patent: Paragraph 0165-0170 |
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