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Basic Information
CAS No.: 32634-66-5
Name: (-)-Di-p-toluoyl-L-tartaric acid
Article Data: 10
Molecular Structure:
Molecular Structure of 32634-66-5 ((-)-Di-p-toluoyl-L-tartaric acid)
Formula: C20H18O8
Molecular Weight: 386.358
Synonyms: Butanedioicacid, 2,3-bis[(4-methylbenzoyl)oxy]-, [R-(R*,R*)]-;(-)-Di-O,O'-p-toluoyltartaric acid;(-)-O,O-Di-p-toluoyltartaric acid;(2R,3R)-(-)-Di(p-toluoyl)tartaric acid;(R,R)-O,O'-Di-p-toluoyltartaric acid;Di-4-toluoyl-L-tartaric acid;L-Di-O,O'-p-toluyltartaric acid;L-Di-p-toluoyltartaric acid;O,O'-Di-p-toluoyl-(2R,3R)-tartaric acid;Tartaricacid, di-p-toluate;
EINECS: 251-131-7
Density: 1.371 g/cm3
Melting Point: 169-171 °C(lit.)
Boiling Point: 626.5 °C at 760 mmHg
Flash Point: 223.2 °C
Solubility: soluble
Appearance: off-white crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 22-24/25-36/37-26
PSA: 136.43000
LogP: 2.15930
Synthetic route
72842-25-2

di-O-p-toluoyl-L-threaric acid-anhydride

32634-66-5

Di-p-toluoyl-L-tartaric acid

Conditions
ConditionsYield
With water
di-O-p-toluoyl-Lg-tartaric acid-anhydride

di-O-p-toluoyl-Lg-tartaric acid-anhydride

32634-66-5

Di-p-toluoyl-L-tartaric acid

Conditions
ConditionsYield
With water; acetone
87-69-4

L-Tartaric acid

874-60-2

4-methyl-benzoyl chloride

32634-66-5

Di-p-toluoyl-L-tartaric acid

Conditions
ConditionsYield
at 170℃; for 1h;
869749-09-7

(R)-α-(2,3-dimethoxyphenyl)-4-piperidinemethanol, (2R,3R)-(-)-di-(p-toluoyl)tartaric acid salt

A

32634-66-5

Di-p-toluoyl-L-tartaric acid

B

243640-19-9

(2,3‐dimethoxyphenyl)(piperidine‐4‐yl)methanol

Conditions
ConditionsYield
Stage #1: (R)-α-(2,3-dimethoxyphenyl)-4-piperidinemethanol, (2R,3R)-(-)-di-(p-toluoyl)tartaric acid salt With ammonia In methanol; water for 2h;
Stage #2: With hydrogenchloride In water Product distribution / selectivity;
A n/a
B n/a

3-aminomethyl-5-methylhexanoic acid (-)-(O,O')-di-p-toluoyl-L-tartaric acid salt

32634-66-5

Di-p-toluoyl-L-tartaric acid

Conditions
ConditionsYield
In tetrahydrofuran; water at 30℃; for 2.33333 - 3h;

C10H14N2*C20H18O8

32634-66-5

Di-p-toluoyl-L-tartaric acid

Conditions
ConditionsYield
With hydrogenchloride In tert-butyl methyl ether; water for 0.5h;345.5 g
32634-66-5, 32634-68-7, 100168-11-4, 104528-81-6

rac-O,O'-di-p-toluoyltartaric acid

A

32634-66-5

Di-p-toluoyl-L-tartaric acid

B

32634-68-7

(2S,3S)-di-4-toluoyltartaric acid

Conditions
ConditionsYield
With C22H24N2(2+)*2CF3O3S(1-) In aq. acetate buffer at 20℃; pH=8.1; Resolution of racemate;
59729-33-8

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

32634-66-5

Di-p-toluoyl-L-tartaric acid

1373405-39-0

C20H18O8*C20H21FN2O

Conditions
ConditionsYield
In isopropyl alcohol Reflux;100%
32634-66-5

Di-p-toluoyl-L-tartaric acid

3-amino-1-(5-bromopyridin-2-yl)-2-(2,4-difluorophenyl)-1,1-difluoropropan-2-ol

3-amino-1-(5-bromopyridin-2-yl)-2-(2,4-difluorophenyl)-1,1-difluoropropan-2-ol

Conditions
ConditionsYield
Stage #1: Di-p-toluoyl-L-tartaric acid; 3-amino-1-(5-bromopyridin-2-yl)-2-(2,4-difluorophenyl)-1,1-difluoropropan-2-ol In isopropyl alcohol; acetonitrile at 20 - 50℃; for 1.5h;
Stage #2: With potassium carbonate In methanol; water at 20 - 30℃;
99.54%
32634-66-5

Di-p-toluoyl-L-tartaric acid

103343-47-1

3-amino-5-phenyl-1,3-dihydrobenzo[e][1,4]diazepin-2-one

C15H13N3O*C20H18O8

Conditions
ConditionsYield
With air In 1,4-dioxane at 20℃; for 24h;99%
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32634-68-7
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  • (-)-DI-P-TOLUOYL-L-TARTARIC ACID

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  • L - (-) - Di (p-methylbenzoyl) tartaric acid (anhydrous)

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    L - (-) - Di (p-methylbenzoyl) tartaric acid (anhydrous)

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Specification

The CAS registry number of (-)-Di-p-toluoyl-L-tartaric acid is 32634-66-5. Its EINECS registry number is 251-131-7. The IUPAC name is(2R,3R)-2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid. In addition, the molecular formula is C20H18O8 and the molecular weight is 386.35. What's more, it is a kind of white to light yellow crystal powder and belongs to the classes of Pharmaceutical Intermediates; Chiral Compounds; Miscellaneous; Carboxylic Acids (Chiral); Chiral Building Blocks; for Resolution of Bases; Optical Resolution; Synthetic Organic Chemistry; Hydroxy Acids & Deriv.; Chiral Compound; Inhibitors; Carboxylic Acids Asymmetric Synthesis; Chiral Resolution Reagents; Organic Building Blocks. It should be stored in sealed container, and put in a cool and dry place.

Physical properties about this chemical are: (1)ACD/LogP: 6.74; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 2; (4)ACD/LogD (pH 7.4): 1.99; (5)ACD/BCF (pH 5.5): 1.42; (6)ACD/BCF (pH 7.4): 1.39; (7)ACD/KOC (pH 5.5): 2.02; (8)ACD/KOC (pH 7.4): 1.97; (9)#H bond acceptors: 8; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 9; (12)Polar Surface Area: 105.2 Å2; (13)Index of Refraction: 1.596; (14)Molar Refractivity: 95.96 cm3; (15)Molar Volume: 281.6 cm3; (16)Polarizability: 38.04 ×10-24cm3; (17)Surface Tension: 60.4 dyne/cm; (18)Density: 1.371 g/cm3; (19)Flash Point: 223.2 °C; (20)Enthalpy of Vaporization: 97.48 kJ/mol; (21)Boiling Point: 626.5 °C at 760 mmHg; (22)Vapour Pressure: 1.47E-16 mmHg at 25°C.

Uses of (-)-Di-p-toluoyl-L-tartaric acid: it can react with 2-[(5-Methylimidazol-4-yl)methylthio]-1-propylamine-Dihydrobromid to get C20H18O8*C8H15N3S. This reaction will need reagent NaOEt/EtOH and solvent aq. ethanol. The yield is about 38% with ambient temperature.


 (-)-Di-p-toluoyl-L-tartaric acid can react with 2-[(5-Methylimidazol-4-yl)methylthio]-1-propylamine-Dihydrobromid to get C20H18O8*C8H15N3S

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing and gloves and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. In addition, you should not breathe dust.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O[C@@H](C(=O)O)[C@@H](OC(=O)c1ccc(cc1)C)C(=O)O)c2ccc(cc2)C
(2)InChI: InChI=1/C20H18O8/c1-11-3-7-13(8-4-11)19(25)27-15(17(21)22)16(18(23)24)28-20(26)14-9-5-12(2)6-10-14/h3-10,15-16H,1-2H3,(H,21,22)(H,23,24)/t15-,16-/m1/s1
(3)InChIKey: CMIBUZBMZCBCAT-HZPDHXFCBJ