(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;ETHYL TARTRATE;D(-)diethyl tartarate;(2R,3R)-diethyl 2,3-dihydroxysuccinate;diethyl (2S,3S)-2,3-dihydroxybutanedioate;(2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl
- CBNumber:
- CB7105982
- Molecular Formula:
- C8H14O6
- Molecular Weight:
- 206.19
- MDL Number:
- MFCD00064451
- MOL File:
- 13811-71-7.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| 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 |
n |
| 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 |
| 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) |
| UNSPSC Code | 12352108 |
| NACRES | NA.22 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H227 | |||||||||
| Precautionary statements | P210e-P280a-P370+P378a-P403+P235-P501a | |||||||||
| PPE | Eyeshields, Gloves | |||||||||
| Hazard Codes | Xi | |||||||||
| Risk Statements | 36/37/38 | |||||||||
| Safety Statements | 24/25-36-26 | |||||||||
| WGK Germany | 3 | |||||||||
| Hazard Note | Irritant | |||||||||
| HS Code | 29181300 | |||||||||
| Storage Class | 10 - Combustible liquids | |||||||||
| REACH Registrations | Active | |||||||||
| NFPA 704 |
|
(2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester price More Price(69)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 213969 | (?)-Diethyl D-tartrate ≥99% | 13811-71-7 | 5g | $57.8 | 2026-04-30 | Buy |
| Sigma-Aldrich | 8.18685 | (2S,3S)-(-)-Diethyl tartrate for synthesis | 13811-71-7 | 25mL | $95.2 | 2026-04-30 | Buy |
| Sigma-Aldrich | 213969 | (?)-Diethyl D-tartrate ≥99% | 13811-71-7 | 25g | $99.6 | 2026-04-30 | Buy |
| TCI Chemical | T1195 | Diethyl D-(-)-Tartrate >97.0%(GC) | 13811-71-7 | 25g | $26 | 2026-04-30 | Buy |
| TCI Chemical | T1195 | Diethyl D-(-)-Tartrate >97.0%(GC) | 13811-71-7 | 250g | $111 | 2026-04-30 | Buy |
(2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester Chemical Properties, Uses, 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
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Shanghai Hanhong Scientific Co.,Ltd. | 021-54306202 13764082696 | info@hanhongsci.com | China | 42917 | 64 |
| SHANGHAI BANGCHENG CHEMICAL Co.,Ltd. | 021-69106960 13701823997 | 13701823733@163.com | China | 4634 | 60 |
| Chengdu rongchuangyiheng Biomedical Technology Co., Ltd | 13438025684 | 28296972@qq.com | China | 146 | 58 |
| Hubei YiKangYuan Chemical Co., Ltd. | 027-87182908 18064088908 | 65824125@qq.com | China | 90 | 55 |
| Shandong Xibang Biological Technology Development Co. LTD | 0536-3611186 15063661551 | 196056703@qq.com | China | 59 | 58 |
| Sigma-Aldrich | 021-61415566 800-8193336 | orderCN@merckgroup.com | China | 51389 | 80 |
| SICHUAN JILONGXINGRUI PHARMA CO,.LTD | 0830-8999890 13883082125 | 511598975@qq.com | China | 13 | 58 |
| Chengdu Likai Chiral Tech LTD. | 028-85247892 | suriya@lkchiralchina.com | China | 45 | 58 |
| J & K SCIENTIFIC LTD. | 18210857532 18210857532 | jkinfo@jkchemical.com | China | 96815 | 76 |
| Meryer (Shanghai) Chemical Technology Co., Ltd. | 4006356688 18621169109 | market03@meryer.com | China | 40202 | 62 |
View Latest Price from (2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2026-08-25 | (2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester
13811-71-7
|
$80.00-800.00 | 10kg | 0.99 | 20tons | Zibo Hangyu Biotechnology Development Co., Ltd | |
 |
2026-05-28 | Diethyl D Tartrate
13811-71-7
|
$2.00-5.00 | 1KG | 99% | 10000kg | Hebei Chuanghai Biotechnology Co,.LTD | |
 |
2026-03-20 | (2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester
13811-71-7
|
$10.00 | 1KG | 99% | 10 mt | Hebei Chuanghai Biotechnology Co., Ltd |
-
- (2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester
13811-71-7
- $80.00-800.00
- 0.99
- Zibo Hangyu Biotechnology Development Co., Ltd
-
- Diethyl D Tartrate
13811-71-7
- $2.00-5.00
- 99%
- Hebei Chuanghai Biotechnology Co,.LTD
-
- (2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester
13811-71-7
- $10.00
- 99%
- Hebei Chuanghai Biotechnology Co., Ltd
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