L(+)-Diethyl L-tartrate Chemical Properties

Melting point:

17 °C

Boiling point:

280 °C (lit.)

alpha 

7.5 º (neat)

Density 

1.204 g/mL at 25 °C (lit.)

vapor pressure 

0.402Pa at 25℃

refractive index 

n20/D 1.446(lit.)

FEMA 

2378 | DIETHYL TARTRATE

Flash point:

200 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Water (Slightly)

pka

11.61±0.20(Predicted)

form 

Viscous Liquid

color 

Clear

Odor

at 100.00 %. mild fruity wine caramellic

Odor Type

fruity

biological source

synthetic

optical activity

[α]20/D +8.5°, neat

Water Solubility 

insoluble

JECFA Number

622

Merck 

14,3855

BRN 

1727145

Dielectric constant

4.5（20℃）

InChIKey

YSAVZVORKRDODB-PHDIDXHHSA-N

LogP

0.2 at 25℃

CAS DataBase Reference

87-91-2(CAS DataBase Reference)

NIST Chemistry Reference

Diethyl tartrate(87-91-2)

EPA Substance Registry System

Butanedioic acid, 2,3-dihydroxy- (2R,3R)-, 1,4-diethyl ester (87-91-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

3

TSCA 

Yes

HS Code 

29181300

MSDS

• Language:English Provider:(2R,3R)(+)-Dihydroxybutane-1,4-dioic acid diethyl ester
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

L(+)-Diethyl L-tartrate Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Chemical Properties

Diethyl tartrate has a mild, fruity, wine aroma.

Occurrence

The d-isomer has not been reported found in nature; the l-isomer and the racemic form are of little importance. Reported found in sherry, white and red wine.

Uses

(+)-Diethyl L-tartrate is used as a chiral auxiliary in the Sharpless enantioselective epoxidation of allylic alcohols, for Sharpless-type enantioselective oxidation of sulfides to sulfoxides and as a chiral auxiliary in the enantioselective construction of cyclopropanes from allylic alcohols by an asymmetric Simmons-Smith reaction. It is also used as a chiral reagent in a host of chemical reactions, such as the synthesis of isoquinoline alkaloids and arundic acid, which has been used in acute ischemic stroke therapy.

Uses

(+)-Diethyl L-tartrate can be used in the synthesis of biologically active compounds such as (+)-altholactone, (-)-aspicilin, (+)-monomorine I and (+)-(1R,2R,3S,6S)-3,6-di-O-methyl conduritol-E.

Uses

Diethyl L-(+)-Tartrate is used as a chiral reagent in a host of chemical reactions, such as the synthesis of isoquinoline alkaloids and arundic acid, which has been used in acute ischemic stroke thera py.

General Description

Made from natural tartaric acid

Flammability and Explosibility

Non flammable

Synthesis

(1) 30 g of L-(+)-tartaric acid was added to a 500 mL three-necked flask followed by 150 mL of anhydrous ethanol. The stirrer was turned on to make the mixture homogeneously mixed, and the reaction temperature was controlled in the range of 0 to 30 °C. 95.4 g of thionyl chloride was slowly added dropwise for 1.5 h, taking care to control the rate of dropwise acceleration to manage the exothermic process. After the dropwise addition, the reaction system was warmed up to 50 °C and the reaction was continued for 2 hours. After completion of the reaction, ethanol was removed by distillation under reduced pressure to obtain the crude product of diethyl L-(+)-tartarate. (2) To the above crude product, 3.3 g of potassium bicarbonate was added, the temperature was raised to 20 °C and the reaction was stirred for 3 hours. At the end of the reaction, the solid insoluble matter was removed by filtration to obtain 39.6 g of L-(+)-diethyl L-tartrate, and the product was a colorless or light yellow oily liquid with a molar yield of 96.2%. The purity of the product was tested to be 99.4%.

References

[1] Tetrahedron Letters, 2013, vol. 54, # 36, p. 4851 - 4853
[2] RSC Advances, 2015, vol. 5, # 15, p. 11687 - 11696
[3] Patent: CN107337603, 2017, A. Location in patent: Paragraph 0025; 0026; 0027; 0028; 0029; 0030; 0031-0040
[4] Journal of Organic Chemistry, 2012, vol. 77, # 19, p. 8465 - 8479,15
[5] Patent: CN106966943, 2017, A. Location in patent: Paragraph 0090; 0091

L(+)-Diethyl L-tartrate(87-91-2)Related Product Information

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