(2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester
- Product Name
- (2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester
- CAS No.
- 13811-71-7
- Chemical Name
- (2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester
- Synonyms
- DET;D-DET;D-tartrate;DIETHYL D-TARTRATE;(-)-Diethyl D-tartrate;D(-)diethyl tartarate;(2R,3R)-diethyl 2,3-dihydroxysuccinate;ETHYL TARTRATE;diethyl (2S,3S)-2,3-dihydroxybutanedioate;(2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl
- CBNumber
- CB7105982
- Molecular Formula
- C8H14O6
- Formula Weight
- 206.19
- MOL File
- 13811-71-7.mol
(2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester Property
- Melting point:
- 17 °C
- Boiling point:
- 162 °C/19 mmHg (lit.)
- alpha
- -9 º (neat)
- Density
- 1.205 g/mL at 20 °C (lit.)
- refractive index
- n20/D 1.446(lit.)
- Flash point:
- 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 activity
- [α]23/D 8.5°, neat
- Water Solubility
- insoluble
- Merck
- 14,3855
- BRN
- 1727143
- 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
- Hazard Codes
- Xi
- Risk Statements
- 36/37/38
- Safety Statements
- 24/25-36-26
- WGK Germany
- 3
- Hazard Note
- Irritant
- HS Code
- 29181300
N-Bromosuccinimide Price
- Product number
- 213969
- Product name
- (?)-Diethyl D-tartrate
- Purity
- ≥99%
- Packaging
- 5g
- Price
- $54.3
- Updated
- 2025/07/31
- Product number
- 8.18685
- Product name
- (2S,3S)-(-)-Diethyl tartrate
- Purity
- for synthesis
- Packaging
- 25mL
- Price
- $89.4
- Updated
- 2025/07/31
- Product number
- 213969
- Product name
- (?)-Diethyl D-tartrate
- Purity
- ≥99%
- Packaging
- 25g
- Price
- $93.5
- Updated
- 2025/07/31
- Product number
- T1195
- Product name
- Diethyl D-(-)-Tartrate
- Purity
- >97.0%(GC)
- Packaging
- 25g
- Price
- $22
- Updated
- 2025/07/31
- Product number
- T1195
- Product name
- Diethyl D-(-)-Tartrate
- Purity
- >97.0%(GC)
- Packaging
- 250g
- Price
- $120
- Updated
- 2025/07/31
(2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester Chemical Properties,Usage,Production
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
64-17-5
147-71-7
13811-71-7
[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
(2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester Preparation Products And Raw materials
Raw materials
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View Lastest Price from (2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester manufacturers
- Product
- (2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester 13811-71-7
- Price
- US $10.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 10 mt
- Release date
- 2024-11-27
- Product
- (2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester 13811-71-7
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 500000kg
- Release date
- 2024-10-30
- Product
- (2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester 13811-71-7
- Price
- US $60.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 5000kg/week
- Release date
- 2024-06-04