2,3-Di-O-para-toluoyl-D-tartaric acid Chemical Properties

Melting point:

169-171 °C(lit.)

alpha 

136 º (c=1, EtOH)

Boiling point:

432.57°C (rough estimate)

Density 

1.3084 (rough estimate)

vapor pressure 

0Pa at 25℃

refractive index 

139 ° (C=1, EtOH)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Ethanol (Sparingly), Methanol (Slightly)

form 

Solid

pka

1.46±0.25(Predicted)

color 

White to Off-White

optical activity

[α]19/D +138°, c = 1 in ethanol

Water Solubility 

112.55mg/L at 25℃

BRN 

3225584

LogP

2.97 at 25℃

CAS DataBase Reference

32634-68-7(CAS DataBase Reference)

NIST Chemistry Reference

(+)-Di-o-4-toluoyl-d-tartaric acid(32634-68-7)

EPA Substance Registry System

Butanedioic acid, 2,3-bis[(4-methylbenzoyl)oxy]-, (2S,3S)- (32634-68-7)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36/37-26

WGK Germany 

3

F 

3-10

TSCA 

T

HS Code 

29181300

MSDS

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2,3-Di-O-para-toluoyl-D-tartaric acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

blood volume expander

Uses

Inhibitor of enzyme. Rivastigmine USP Related Compound A.

Flammability and Explosibility

Not classified

Synthesis

General procedure for the synthesis of D-(+)-di-p-toluoyltartaric acid from L-(-)-p-toluoyltartaric anhydride: 150 g of D-tartaric acid and 200 mL of toluene were added to a 1000 mL three-necked flask, and 1.5 g of copper sulfate was added as a catalyst under stirring conditions. 330 g of methylbenzoyl chloride was slowly added dropwise for a controlled period of 3 hours. After the dropwise addition, the reaction was continued for 6 hours. Upon completion of the reaction, the mixture was transferred to a centrifuge for separation. Next, 495.4 g of DP-methyldibenzoyltartaric anhydride, appropriate amount of water and toluene were added to a 2000 mL three-necked flask, heated to reflux and kept for 5 hours. At the end of the reaction, it was cooled to room temperature and 374.4 g of DP-methyldibenzoyltartaric acid was isolated. The product was used for TEM test and its structure is shown in Figure 1. The purity of the finished product D-p-methyldibenzoyltartaric acid was determined to be 99.61% with an overall yield of 96.6%.

References

[1] Patent: CN104447338, 2016, B. Location in patent: Paragraph 0034-0036

2,3-Di-O-para-toluoyl-D-tartaric acid(32634-68-7)Related Product Information

• (-)-Di-p-toluoyl-L-tartaric acid
• Di-p-toluoyl-D-tartaric acid monohydrate
• DL-Malic acid
• (+)-Dibenzoyl-D-tartaric acid monohydrate
• Di-p-anisoyl-L-tartaric acid
• (-)-Dibenzoyl-L-tartaric acid monohydrate
• Dibenzoyl-L-tartaric acid
• (+)-Dibenzoyl-D-tartaric acid
• Dibenzoyltartaric acid
• tert-Butanesulfinamide
• D-Tartaric acid
• 2,3-Di-O-para-toluoyl-D-tartaric acid
• 4-[(1S)-(4-Dimethylamino)-1-(4-fluotophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile (2R,3R)-2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid
• (+)-NICOTINE (+)-DI-P-TOLUOYLTARTRATE SALT
• R-VENLAFAXINE-DI-P-TOLUOYL-D-TARTRATE SALT