(+)-Dibenzoyl-D-tartaric acid supplier

Name
(+)-Dibenzoyl-D-tartaric acid
EINECS 241-097-1
CAS No. 17026-42-5
Article Data19
CAS DataBase
Density 1.438 g/cm³
Solubility insoluble in water
Melting Point 154-156 ºC (lit.)
Formula C₁₈H₁₄O₈
Boiling Point 606.6 ºC at 760 mmHg
Molecular Weight 358.304
Flash Point 221.8 ºC
Transport Information
Appearance white to light yellow crystal powder
Safety 26-36/37/39
Risk Codes 36
Molecular Structure
Hazard Symbols Xi
Synonyms [+]-Dibenzoyltartaric acid;Dibenzoyl-D-tartaric acid;D-(+)-Di-Benzoyltartaric Acid (D-DBTA);D-(+)-Di-Benzoyltartaric acid;D-DBTA;
PSA 127.20000
LogP 1.60680

Synthetic route

: L-1-phenyl-2-(1-pyrrolidinyl)-1-propanone-(-)-dibenzoyl-L-tartaric acid salt

A: 19134-50-0
(SR)-(+/-)-1-phenyl-2-(1-pyrrolidinyl)-1-propanone

B: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide In water; ethyl acetate at 80℃; for 5h; pH=2 - 11.5;	A 87.6% B n/a

: S-nicotine dibenzoyl-d-tartrate

A: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

B: 54-11-5
nicotin

Conditions

Conditions	Yield
With hydrogenchloride In water for 0.166667h; Product distribution / selectivity;	A n/a B 65.5%

: 147-71-7
D-tartaric acid

: 98-88-4
benzoyl chloride

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: 2743-38-6, 17026-42-5, 22333-70-6, 100632-52-8, 111955-48-7
(+/-)-2,3-O-dibenzoyltartaric acid

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

di-O-benzoyl-Dg-tartaric acid-anhydride: di-O-benzoyl-Dg-tartaric acid-anhydride

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

Conditions

Conditions	Yield
With water

: 2743-38-6, 17026-42-5, 22333-70-6, 100632-52-8, 111955-48-7
(+/-)-2,3-O-dibenzoyltartaric acid

A: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

B: 2743-38-6
O,O'-dibenzoyl-L-tartaric acid

Conditions

Conditions	Yield
With N-isopropylcarbamoyl-derivatized cyclofructan-6 column In methanol; acetic acid; triethylamine; acetonitrile at 20℃; Resolution of racemate;

: 2743-38-6, 17026-42-5, 22333-70-6, 100632-52-8, 111955-48-7
rac-tartaric acid dibenzoate

A: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

B: 2743-38-6
O,O'-dibenzoyl-L-tartaric acid

Conditions

Conditions	Yield
With chiral stationary phase including (R)-naphthylethyl-carbamate-functionalized CF6 In methanol; acetic acid; triethylamine; acetonitrile at 20℃; Purification / work up; Resolution of racemate;
With (3R,7R)-1,9-dimethyl-3,7-diphenyl-2,3,5,7,8,9-hexahydro-1H-diimidazo[1,2-c:2',1'-f][1,3,2]diazaphosphinin-4-ium-5-olate-5-oxide In chloroform-d1 at 23℃; Resolution of racemate;

: 175591-23-8
tapentadol

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol hemi-(2S,3S)-dibenzoyltartrate

Conditions

Conditions	Yield
In acetone at 20℃; for 3h;	100%

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: 2-phenyl-2-(piperidin-2-yl)acetic acid

: d-threo-ritalinic acid dibenzoyl-D-tartrate

Conditions

Conditions	Yield
Stage #1: 2-phenyl-2-(piperidin-2-yl)acetic acid With oxalic acid In methanol; water at 25 - 30℃; for 1h; Stage #2: O,O'-dibenzoyl-D-tartaric acid In methanol; water at 5 - 70℃; for 10h;	100%

: 106-88-7
ethyloxirane

: 75-18-3
dimethylsulfide

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: 140427-67-4
dimethyl 2-hydroxybutyl sulfonium dibenzoyltartrate

Conditions

Conditions	Yield
In dichloromethane for 24h; Ambient temperature;	99%

...Expand

: N,N'-bis(1,3-dimethyl-2-imidazolidinylidene)-o-benzenediamine

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: C16H24N6*2C18H14O8

Conditions

Conditions	Yield
In water; ethyl acetate at 20℃; for 3h;	97.9%

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

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: (R)-5-((E)-2-pyrrolidin-3-ylvinyl)pyrimidine hemi-di-benzoyl-D-tartarate

Conditions

Conditions	Yield
In ethanol at 20℃; Reflux;	95.2%
In ethanol Reflux;	95.2%

: 75-18-3
dimethylsulfide

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: 556-52-5
oxiranyl-methanol

: 140630-30-4
2,3-dihydroxypropyl dimethyl sulfonium dibenzoyltartrate

Conditions

Conditions	Yield
In dichloromethane for 16h; Ambient temperature;	95%

...Expand

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: 2-(1-azabicyclo[2.2.2]oct-2-yl)-6-(3-methyl-1H-pyrazol-4-yl)thieno[3,2-d]pyrimidin-4(3H)-one

A: (2S,3S)-2,3-bis(benzoyloxy)butanedioic acid 2-[1-azabicyclo[2.2.2]oct-2-yl]-6-(3-methyl-1H-pyrazol-4-yl)thieno[3,2-d]pyrimidin-4(3H)-one

B: (2S,3S)-2,3-bis(benzoyloxy)butanedioic acid 2-[(2S)-1-azabicyclo[2.2.2]oct-2-yl]-6-(3-methyl-1H-pyrazol-4-yl)thieno[3,2-d]pyrimidin-4(3H)-one

Conditions

Conditions	Yield
In acetic acid; butan-1-ol at 80 - 90℃; for 3h; Solvent; Temperature; Large scale;	A n/a B 94.8%

...Expand

: 75-18-3
dimethylsulfide

: 7501-44-2
hexadecanoic acid, glycidyl ester

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: 140427-55-0
dimethyl (3-hexadecanoyloxy-2-hydroxypropyl) sulfonium dibenzoyltartrate

Conditions

Conditions	Yield
In dichloromethane for 24h; Ambient temperature;	93%

...Expand

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

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: 1228391-42-1
(R)-5-((E)-2-pyrrolidin-3-ylvinyl)pyrimidine mono-di-benzoyl-D-tartarate

Conditions

Conditions	Yield
In ethanol at 20℃; Heating;	93%
In ethanol Heating;	93%

: 110-01-0
thiophene

: 106-88-7
ethyloxirane

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: 140427-51-6
2-(2-hydroxybutyl)thiolanium dibenzoyltartrate

Conditions

Conditions	Yield
In dichloromethane for 24h; Ambient temperature;	92%

...Expand

: 1221278-64-3
6-phenethyl-octahydro-pyrrolo[2,3-c]pyridine

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: C15H22N2*C18H14O8

Conditions

Conditions	Yield
In ethanol; isopropyl alcohol; toluene at 20℃; for 15h; Resolution of racemate;	92%

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: 6-phenethyloctahydropyrrolo[2,3-c]pyridine

A: C15H22N2*C18H14O8

B: C15H22N2

Conditions

Conditions	Yield
In ethanol; isopropyl alcohol; toluene at 20℃; for 16h; Inert atmosphere;	A 92% B n/a

...Expand

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: (2RS,3S)-2-amino-3-methylpentanoic acid

A: C18H14O8*C6H13NO2

B: (2S,3S)-2,3-Bis-benzoyloxy-succinic acid; compound with (2R,3S)-2-amino-3-methyl-pentanoic acid

Conditions

Conditions	Yield
With salicylaldehyde; acetic acid In n-heptane; acetic acid butyl ester at 80℃; for 5h;	A n/a B 90%

...Expand

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: 43200-80-2
zopiclon

A: 144025-94-5
(R)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate D-(+)-O,O'-dibenzoyltartaric acid salt

B: 144025-93-4
eszopiclone dibenzoyl-D-tartrate

Conditions

Conditions	Yield
In acetonitrile at 21℃; for 2h; Temperature; Solvent; Optical yield = 87.4 %ee;	A 89.8% B n/a
In 1-methyl-pyrrolidin-2-one; water at 60 - 65℃; for 1h; Resolution of racemate;	A n/a B 86.25%
In dichloromethane at 20℃; for 3h; Purification / work up; Resolution of racemate;
In acetonitrile at 25 - 35℃; for 6 - 7h;
In water; acetonitrile at 25 - 80℃; for 3 - 4.5h; Purification / work up; Resolution of racemate;

...Expand

: 1186316-72-2
(S)-3-(4-chlorophenyl-2-chloropyrid-3-ylmethoxy)azetidine

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: 1186316-77-7
(S)-3-(4-chlorophenyl-2-chloropyrid-3-ylmethoxy)azetidine dibenzoyl tartate

Conditions

Conditions	Yield
In isopropyl alcohol	89%

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: 69082-94-6
meso-mono(β-o-aminophenyl)triphenylporphyrin

: C106H72N10O6

Conditions

Conditions	Yield
Stage #1: O,O'-dibenzoyl-D-tartaric acid With thionyl chloride for 10h; Schlenk technique; Inert atmosphere; Reflux; Stage #2: meso-mono(β-o-aminophenyl)triphenylporphyrin With triethylamine In dichloromethane at 20℃; for 8h;	89%

: 19395-39-2
(±)-erythro/threo-2-phenyl-2-(piperidin-2-yl)acetamide

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: 741272-48-0
d-threo-[R(R*,R*)]-2-phenyl-2-piperidine-2-yl acetamide dibenzoyl-d-tartrate

Conditions

Conditions	Yield
In isopropyl alcohol at 20 - 55℃; for 6.5h; Resolution of racemate;	88%

: 951760-12-6
(+/-)-2-iodo-6H,12H,5,11-methanodibenzo[b,f][1,5]diazocine

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: 1478192-94-7
(+)-S,S-2-iodo-6,12-dihydro-5,11-methanodibenzo[b,f ][1,5]-diazocine*(+)-O,O′-dibenzoyl-D-tartaric acid

Conditions

Conditions	Yield
In 1,2-dichloro-ethane at 55 - 60℃; for 120h; Resolution of racemate;	88%

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: 390357-42-3, 1042268-76-7, 1042269-05-5
2,8-dibromo-6H,12H-5,11-methanodibenzo[b,f][1,5]-diazocine

: 1478192-77-6
(+)-S,S-2,8-dibromo-6,12-dihydro-5,11-methanodibenzo-[b,f ][1,5]diazocine*(+)-O,O′-dibenzoyl-D-tartaric acid

Conditions

Conditions	Yield
In 1,2-dichloro-ethane at 55 - 60℃; for 120h; Resolution of racemate;	88%

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: 43200-80-2
zopiclon

: 1020156-02-8
D(+)-O,O-dibenzoyl tartarate of zopiclone

Conditions

Conditions	Yield
In water; acetonitrile at 25 - 35℃; for 7h;	86.63%

: 33105-81-6
2-amino-3,3-dimethylbutanoic acid

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

A: 26782-71-8
D-tert-leucine

B: L-tert-leucine dibenzoyl-D-tartrate

Conditions

Conditions	Yield
In water at 28℃; for 24h; Resolution of racemate;	A 85% B n/a

...Expand

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

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

: C18H14O8*C13H19NO

Conditions

Conditions	Yield
With sodium hydroxide In water; acetone at 20℃;	85%

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: C19H24O4S

: C12H20N2O*C18H14O8

Conditions

Conditions	Yield
Stage #1: C19H24O4S With hydrazine hydrate In ethanol at 65℃; for 16h; Inert atmosphere; Autoclave; Stage #2: O,O'-dibenzoyl-D-tartaric acid In tert-butyl methyl ether for 3.5h;	85%

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: 19432-37-2
Benzylidene-methyl-naphthalen-1-yl-phenyl-λ5-phosphane

: 84673-94-9
(2S,3S)-2,3-Bis-benzoyloxy-3-carboxy-propionatebenzyl-methyl-naphthalen-1-yl-phenyl-phosphonium;

Conditions

Conditions	Yield
In tetrahydrofuran	84%

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: trans-2,5-diallylpyrrolidine

: bis(trans-2,5-diallylpyrrolidine-1-ium) dibenzoyltartrate (2-)

Conditions

Conditions	Yield
In chloroform for 32h; Acylation;	84%

: 17026-42-5
O,O'-dibenzoyl-D-tartaric acid

: 17637-11-5, 64339-95-3, 111955-47-6, 116780-73-5
(3S,4S)-2,5-dioxotetrahydrofuran-3,4-diyl dibenzoate

Conditions

Conditions	Yield
With acetic anhydride at 85℃; for 2h;	84%
With acetic anhydride at 85℃; for 2h;	84%
With acetic anhydride at 85℃; for 2h;	84%

(+)-Dibenzoyl-D-tartaric acid Specification

The (+)-Dibenzoyl-D-tartaric acid, with its CAS registry number 17026-42-5, has the IUPAC name of 2,3-dibenzoyloxybutanedioic acid. For being a kind of white to light yellow crystal powder, it is sensitive and hygroscopic and is also insoluble in water. As to its usage, it is usually applied as the intermediate of anthelmintic levamisol, with its product categories including Pharmaceutical Intermediates; Fine Chemical & Intermediates; Chiral Compounds; Substrates; chiral; Chiral chemicals; Hydroxy acids & Deriv.; Chiral Compound.

The characteristics of this chemical are as below: (1)ACD/LogP: 5.82; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 1.11; (4)ACD/LogD (pH 7.4): 1.07; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 8; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 9; (12)Polar Surface Area: 105.2; (13)Index of Refraction: 1.609; (14)Molar Refractivity: 86.31 cm³; (15)Molar Volume: 249.1 cm³; (16)Polarizability: 34.21×10^-24 cm³; (17)Surface Tension: 65.9 dyne/cm; (18)Density: 1.438 g/cm³; (19)Flash Point: 221.8 °C; (20)Enthalpy of Vaporization: 94.8 kJ/mol; (21)Boiling Point: 606.6 °C at 760 mmHg; (22)Vapour Pressure: 1.45E-15 mmHg at 25°C; (23)Exact Mass: 358.068867; (24)MonoIsotopic Mass: 358.068867; (25)Topological Polar Surface Area: 127; (26)Heavy Atom Count: 26; (27)Complexity: 483.

When you are dealing with this chemical, you should be cautious. This chemical is irritating to eyes and may cause inflammation to the skin or other mucous membranes. Therefore, you should wear suitable protective clothing, gloves and eye/face protection and if in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

Additionally, you could obtain the molecular structure by converting the following datas:
(1)Canonical SMILES: C1=CC=C(C=C1)C(=O)OC(C(C(=O)O)OC(=O)C2=CC=CC=C2)C(=O)O
(2)InChI: InChI=1S/C18H14O8/c19-15(20)13(25-17(23)11-7-3-1-4-8-11)14(16(21)22)26-18(24)12-9-5-2-6-10-12/h1-10,13-14H,(H,19,20)(H,21,22)
(3)InChIKey: YONLFQNRGZXBBF-UHFFFAOYSA-N

Product Name

(+)-Dibenzoyl-D-tartaric acid

Synthetic route

(+)-Dibenzoyl-D-tartaric acid Specification

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