(+)-Di-1,4-toluoyl-D-tartaric acid supplier

Name
2,3-Di-O-para-toluoyl-D-tartaric acid
EINECS 251-132-2
CAS No. 32634-68-7
Article Data6
CAS DataBase
Density 1.371 g/cm³
Solubility 112.55mg/L at 25℃
Melting Point 169-171 °C(lit.)
Formula C₂₀H₁₈O₈
Boiling Point 626.5 °C at 760 mmHg
Molecular Weight 386.358
Flash Point 223.2 °C
Transport Information
Appearance off-white crystalline powder
Safety 22-24/25-36/37-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Butanedioicacid,2,3-bis[(4-methylbenzoyl)oxy]-,[S-(R*,R*)]-;Tartaric acid,di-p-toluate, (+)- (8CI);p-Toluic acid, diester with D-tartaric acid (7CI);(2S,3S)-2,3-Bis[(4-methylbenzoyl)oxy]succinic acid;
PSA 127.20000
LogP 2.22360

Synthetic route

: 32634-66-5, 32634-68-7, 100168-11-4, 104528-81-6
rac-O,O'-di-p-toluoyltartaric acid

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

Conditions

Conditions	Yield
ueber das Cinchonin-Salz;

di-O-p-toluoyl-Dg-tartaric acid-anhydride: di-O-p-toluoyl-Dg-tartaric acid-anhydride

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

Conditions

Conditions	Yield
With water; acetone

: 339546-21-3
(R)-2-cyclopropylaminocyclohexanol di-p-toluoyl-D-tartrate

A: 339546-20-2
(R)-2-cyclopropylaminocyclohexanol

B: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

Conditions

Conditions	Yield
With sodium hydroxide In water at 20 - 30℃; for 1h; Product distribution / selectivity;	A n/a B n/a

: (+)-di-O,O'-toluoyl-D-tartaric acid mono-NH4 salt

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

Conditions

Conditions	Yield
With Amberlite 1R In isopropyl alcohol Product distribution / selectivity;
With hydrogenchloride In dichloromethane; water pH=< 0.5; Product distribution / selectivity;

: 72842-25-2
(3S,4S)-2,5-dioxotetrahydrofuran-3,4-diyl bis(4-methylbenzoate)

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

Conditions

Conditions	Yield
With water In toluene for 5h; Reflux; Large scale;	374.4g

: 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

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

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: 128013-69-4, 130912-52-6, 148553-50-8, 148553-51-9
(R,S)-3-iso-butyl-4-aminobutyric acid

A: (S)-pregabalin O,O'-di-p-toluoyl-(D)-tartrate

B: (R)-pregabalin O,O'-di-p-toluoyl-(D)-tartrate

Conditions

Conditions	Yield
In water; butan-1-ol at 20 - 25℃; Resolution of racemate;	A 98% B n/a

...Expand

: 753015-44-0
(R)-5-((E)-2-pyrrolidin-3-ylvinyl)pyrimidine

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: 1228391-41-0
(R)-5-((E)-2-pyrrolidin-3-ylvinyl)pyrimidine mono-di-p-toluoyl-D-tartarate

Conditions

Conditions	Yield
In ethanol Reflux;	96.1%
In ethanol Reflux;	96.1%

: 20431-81-6
rac-trans-2-methylamino-cyclohexanol

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

A: 2C7H15NO*C20H18O8

B: 21651-84-3
trans-2-(methylamino)cyclohexanol

Conditions

Conditions	Yield
In ethanol at 45 - 60℃; for 1h;	A 95% B n/a

...Expand

: 7-trifluoromethyl-2,3,4,5-tetrahydro-1,5-methylene-1H-3-benzazepine

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: 873788-21-7
(1S,8R)-(+)-4-trifluoromethyl-10-azatricyclo[6.3.1.0(2,7)]dodeca-2(7),3,5-triene di-p-toluoyl-D-(-)-tartaric acid salt

Conditions

Conditions	Yield
In acetonitrile at 82℃; for 1 - 24h; Product distribution / selectivity;	94%

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: 510-77-0, 1668-86-6, 7318-55-0
(4aS,8aS)-rel-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-one

: [(-)-narwedine][di-p-toluoyl-D-tartrate]

Conditions

Conditions	Yield
In ethanol at 40℃; Heating / reflux;	90%

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: 54208-72-9
2-(tert-butylamino)-1-(2,2-dimethyl-4H-benzo[d][1,3]dioxan-6-yl)ethanol

: 2C16H25NO3*C20H18O8

Conditions

Conditions	Yield
In methanol for 0.166667h; Heating / reflux;	90%
In methanol for 0.25h; Heating / reflux;	73%

: 1095823-56-5
2-(1-aminoethyl)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)thiazole-5-carboxamide

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

A: 1095825-44-7
C12H10ClF3N4OS

B: 1095823-60-1
C12H10ClF3N4OS*C20H18O8

Conditions

Conditions	Yield
In water; isopropyl alcohol at 45 - 53℃; for 21h; Purification / work up; Resolution of racemate;	A n/a B 88%

...Expand

: (8-hydroxy-4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-yl)acetonitrile

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: 2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylaminedi-p-toluoyl-L-(-)-tartrate

Conditions

Conditions	Yield
Stage #1: (8-hydroxy-4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-yl)acetonitrile With ammonia; hydrogen In ethanol at 55℃; under 18751.9 Torr; for 15h; Stage #2: (2S,3S)-di-4-toluoyltartaric acid at 20℃; for 0.75h; Temperature; Pressure; Solvent;	87.8%

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: 21498-08-8
lofexidine hydrochloride

A: (+/-)-lofexidine di-p-toluoyl-D-tartarate

B: (+/+)-lofexidine di-p-toluoyl-D-tartarate

Conditions

Conditions	Yield
In ethanol	A 87% B n/a

...Expand

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: 108157-52-4
(S)-1-(2-piperidino-phenyl)-3-methyl-1-butylamine

: 1098066-89-7
(S)-3-methyl-1-(2-piperidino-phenyl)-1-butylamine di-p-toluoyl-D-tartaric acid salt

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In methanol; water at 25 - 60℃; Product distribution / selectivity;	85.7%

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: 510-77-0, 1668-86-6, 7318-55-0
(4aS,8aS)-rel-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-one

: [(-)-narwedine]2[di-p-toluoyl-D-tartrate]

Conditions

Conditions	Yield
In ethanol at 20 - 40℃; for 19h; Heating / reflux;	83%
In ethanol at 40℃; Heating / reflux;	79%

: 5-azaspiro[2.4]heptane-6-carboxylic acid

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: (S)-5-azaspiro[2.4]heptane-6-carboxylic acid D-di-p-methylbenzoyltartrate

Conditions

Conditions	Yield
Stage #1: 5-azaspiro[2.4]heptane-6-carboxylic acid; (2S,3S)-di-4-toluoyltartaric acid With acetic acid at 60℃; for 0.333333h; Stage #2: With ethyl acetate at 50℃; for 1.5h; Enzymatic reaction; Stage #3: With salicylaldehyde at 50℃; for 18h;	83%

: 34737-89-8
1-Benzyl-3-methyl-4-piperidon

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: (R)-1-benzyl-3-methylpiperidin-4-one (2S,3S)-2,3-bis((4-methylbenzoyl)oxy)succinic acid salt

Conditions

Conditions	Yield
In acetonitrile at 40℃; for 12h; Large scale;	83%
In acetonitrile at 40℃; for 12h; Large scale;	83%
In acetonitrile at 40℃; for 12h; Large scale;	83%

: (S)-methyl 2-(8-fluoro-3-(2-methoxy-5-(trifluoromethyl)phenyl)-2-(4-(3-methoxyphenyl)piperazin-1-yl)-3,4-dihydroquinazolin-4-yl)acetate

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: 141-78-6
ethyl acetate

: (S)-methyl 2-(8-fluoro-3-(2-methoxy-5-(trifluoromethyl)phenyl)-2-(4-(3-methoxyphenyl)piperazin-1-yl)-3,4-dihydroquinazolin-4-yl)acetate (2S,3S)-2,3-bis((4-methylbenzoyl)oxy)succinate ethyl acetate

Conditions

Conditions	Yield
In toluene at 45℃; Inert atmosphere;	82%

...Expand

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: (+)-(S,S)-D-O,O'-di-p-toluoyltartaric acid monosodium salt

Conditions

Conditions	Yield
With sodium hydroxide In water for 0.166667h; Sonication;	82%

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: 171338-27-5
[2R-[2α(R*),3α]]-2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine

: 1404074-27-6
BFM2-(D)-DTTA

Conditions

Conditions	Yield
In isopropyl alcohol at 50 - 55℃; for 0.333333h; Product distribution / selectivity; Industry scale;	80%

: 62498-69-5
didesmethylcitalopram

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

A: S-(+)-1-(3-amino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile (-)-di-p-toluoyltartrate

B: R-1-(3-amino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile (-)-di-p-toluoyltartrate

Conditions

Conditions	Yield
Stage #1: didesmethylcitalopram; (2S,3S)-di-4-toluoyltartaric acid In acetonitrile at 20℃; Stage #2: In water; acetonitrile at 0 - 60℃; Solvent;	A 80% B n/a

...Expand

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: 5933-40-4
(R)-(+)-N,α-dimethylbenzylamine

: (R)-N-methyl-α-methylbenzylammonium di-p-toluoyl-D-tartrate

Conditions

Conditions	Yield
In methanol; ethyl acetate at 20℃; for 1h;	80%

: 19131-99-8
N-methyl-N-[(S)-1-phenylethyl]amine

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: (S)-N-methyl-α-methylbenzylammonium di-p-toluoyl-D-tartrate

Conditions

Conditions	Yield
In methanol; ethyl acetate at 20℃; for 1h;	80%

: 1025064-33-8
α-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-1-naphthalenemethanamine

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: (R)-cinacalcet (-)-di-para-D-toluoyl tartrate

Conditions

Conditions	Yield
In ethyl acetate at 25 - 65℃; for 0.75h;	78%

: C30H30F4N4O4*C7H6O3

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: 917389-30-1
(2S,3S)-2,3-bis[(4-methylbenzoyl)oxy]succinic acid {(4S)-8-fluoro-2-[4-(3-methoxyphenyl)piperazin-1-yl]-3-(2-methoxy-5-(trifluormethyl)phenyl)-3,4-dihydroquinazolin-4-yl}acetic acid methyl ester

Conditions

Conditions	Yield
Stage #1: C30H30F4N4O4*C7H6O3 With potassium phosphate In water; toluene at 20℃; for 1h; Stage #2: With potassium phosphate; (1S,2S,4S,5R)-1-(3,5-bis(trifluoromethyl)benzyl)-2-((R)-hydroxy(1-(3-(trifluoromethyl)benzyl)quinolin-1-ium-4-yl)methyl)-5-vinylquinuclidin-1-ium bromide In water; N,N-dimethyl-formamide; toluene at 0℃; Stage #3: (2S,3S)-di-4-toluoyltartaric acid In ethyl acetate; toluene at 20℃; for 12h;	78%

Yield

Stage #1: C30H30F4N4O4*C7H6O3 With potassium phosphate In water; toluene at 20℃; for 1h;
Stage #2: With potassium phosphate; (1S,2S,4S,5R)-1-(3,5-bis(trifluoromethyl)benzyl)-2-((R)-hydroxy(1-(3-(trifluoromethyl)benzyl)quinolin-1-ium-4-yl)methyl)-5-vinylquinuclidin-1-ium bromide In water; N,N-dimethyl-formamide; toluene at 0℃;
Stage #3: (2S,3S)-di-4-toluoyltartaric acid In ethyl acetate; toluene at 20℃; for 12h;

78%

: 90-84-6, 39648-49-2, 39648-50-5
amfepramone

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: C20H18O8*C13H19NO

Conditions

Conditions	Yield
With sodium hydroxide In water; acetone at 20℃;	78%

: C15H18N2O2

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: C20H18O8*C15H18N2O2

Conditions

Conditions	Yield
In water; acetonitrile Solvent;	78%

: 726201-98-5
trans-N-(2-hydroxycyclohexyl)-N-cyclopropylamine

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: 339546-21-3
(R)-2-cyclopropylaminocyclohexanol di-p-toluoyl-D-tartrate

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 20 - 70℃; for 2.5h; Resolution of racemate;	77.8%

: 646055-67-6
rac-7-(3-pyridinyl)-1,7-diazaspiro[4.4]nonane

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: 1174118-94-5
(S)-7-(3-pyridinyl)-1,7-diazaspiro[4.4]nonane mono-(+)-di-O,O'-p-toluoyl-D-tartrate

Conditions

Conditions	Yield
In ethanol at 20 - 50℃; Purification / work up; Reflux; Resolution of racemate;	76.4%

: 273748-55-3
(±)-2-(pyridin-3-ylmethylidene)-1-azabicyclo[2.2.2]octan-3-one

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: 1111942-08-5
(2S)-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]octan-3-one di-p-toluoyl-D-tartrate

Conditions

Conditions	Yield
Stage #1: (±)-2-(pyridin-3-ylmethylidene)-1-azabicyclo[2.2.2]octan-3-one With hydrogen; palladium 10% on activated carbon In methanol at 20℃; for 12h; Industry scale; Stage #2: (2S,3S)-di-4-toluoyltartaric acid In ethanol at 15 - 30℃; for 13h; Industry scale; Heating / reflux;	76.2%

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: 72842-25-2
(3S,4S)-2,5-dioxotetrahydrofuran-3,4-diyl bis(4-methylbenzoate)

Conditions

Conditions	Yield
With acetic anhydride at 85℃; for 2h;	76%

: 1206633-34-2
C23H24F3N

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: C20H18O8*(x)C23H24F3N

Conditions

Conditions	Yield
In ethyl acetate at 25 - 65℃; for 0.75h;	74.3%

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: 3-amino-5-phenyl-1,3-dihydro-2H-benzo[b]azepin-2-one

: (S)-3-amino-5-phenyl-1,3-dihydro-2H-benzo[b]azepin-2-one

Conditions

Conditions	Yield
Stage #1: (2S,3S)-di-4-toluoyltartaric acid; 3-amino-5-phenyl-1,3-dihydro-2H-benzo[b]azepin-2-one In 1,4-dioxane at 20℃; for 24h; Stage #2: With sodium hydroxide In water at 20℃; for 4h;	73.2%
Stage #1: (2S,3S)-di-4-toluoyltartaric acid; 3-amino-5-phenyl-1,3-dihydro-2H-benzo[b]azepin-2-one In 1,4-dioxane at 20℃; for 24h; Stage #2: With sodium hydroxide at 20℃; for 4h;	73.2%

: 17279-31-1
(-)-(S)-N,N-dimethyl-1-phenylethylamine

: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

: (S)-N,N-dimethyl-α-methylbenzylammonium di-p-toluoyl-D-tartrate

Conditions

Conditions	Yield
In Isopropyl acetate Reflux;	73%

(+)-Di-1,4-toluoyl-D-tartaric acid Specification

The CAS registry number of (-)-Di-p-toluoyl-L-trataric acid is 32634-68-7. The IUPAC name systematic name is (2S,3S)-2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid. Its EINECS registry number is 251-132-2. In addition, the molecular formula is C₂₀H₁₈O₈ and the molecular weight is 386.35. It is a kind of white to light yellow crystal powder and belongs to the classes of Pharmaceutical Intermediates; Fine Chemical & Intermediates; Chiral Compounds; Miscellaneous; Carboxylic Acids (Chiral); Chiral Building Blocks; Optical Resolution; Synthetic Organic Chemistry; Hydroxy Acids & Deriv.; Chiral Compound.

Physical properties about (-)-Di-p-toluoyl-L-trataric acid 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.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing and gloves. And you should avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. In addition, do 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-/m0/s1
(3)InChIKey: CMIBUZBMZCBCAT-HOTGVXAUBA

Product Name

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

Synthetic route

(+)-Di-1,4-toluoyl-D-tartaric acid Specification

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