80822-15-7

Basic information

• Product Name: (+)-Dibenzoyl-D-tartaric acid monohydrate
• Synonyms: (+)-Dibenzoyl-D-tartaric acid Monohydrate, 99% ee, 98% 50GR;(+)-Dibenzoyl-D-tartaric acid Monohydrate, 98%, ee: 99%;D-DBTA(H20);D-(+)DBTA, Dibenzoyl-D-tartaric acid, Monohydrate;DBTA (Di-O,O'-benzoyl-D-(+)tartaric Acid Monohydrate);(+)-2,3-DIBENZOYL-D-TARTARIC ACID MONOHYDRATE;2,3-di-o-benzoyl-d-tartaric acid hydrate;(2S,3S)-(+)-DIBENZOYL-D-TARTARIC ACID MONOHYDRATE
• CAS NO: 80822-15-7
• Molecular Formula: C₁₈H₁₄O₈*H₂O
• Molecular Weight: 376.31
• EINECS: 241-097-1
• Product Categories: Pharmaceutical Intermediates;FINE Chemical & INTERMEDIATES;chiral;API;Carboxylic Acids (Chiral);Chiral Building Blocks;for Resolution of Bases;Optical Resolution;Synthetic Organic Chemistry;CHIRAL CHEMICALS;Hydroxy Acids & Deriv.;Chiral Compound
• Mol File: 80822-15-7.mol
• Article Data: 0

Chemical Properties

• Melting Point: 150-153 °C
• Boiling Point: 606.6 °C at 760 mmHg
• Flash Point: 221.8 °C
• Appearance: white to light yellow crystal powder
• Vapor Pressure: 1.45E-15mmHg at 25°C
• Refractive Index: 109 ° (C=1, EtOH)
• Storage Temp.: Refrigerator, Under inert atmosphere
• Solubility: DMSO (Soluble), Ethanol (Slightly, Sonicated), Methanol (Sparingly)
• Water Solubility: Soluble in methanol. Slightly soluble in water.
• BRN: 6121616
• CAS DataBase Reference: (+)-Dibenzoyl-D-tartaric acid monohydrate(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Dibenzoyl-D-tartaric acid monohydrate(80822-15-7)
• EPA Substance Registry System: (+)-Dibenzoyl-D-tartaric acid monohydrate(80822-15-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 37/39-26
• TSCA: Yes
• Hazardous Substances Data: 80822-15-7(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

(+)-Dibenzoyl-D-tartaric acid monohydrate is used as a chiral separation and racemization agent for amines. It is also used as a pharmaceutical raw material.

InChI:InChI=1/C18H14O8.H2O/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);1H2/t13-,14-;/m0./s1

Synthetic route

ethanol (64-17-5) + (+/-)-crispine A (15889-93-7) + (+)-dibenzoyl-D-tartaric acid monohydrate (80822-15-7) → (+)-crispine A*(+)-dibenzoyl-D-tartaric acid*ethanol

Conditions	Yield
Reflux; optical yield given as %ee;	87%

(+)-dibenzoyl-D-tartaric acid monohydrate (80822-15-7) + 3-quinuclidinol (1619-34-7) → C7H13NO*C18H14O8

Conditions	Yield
In methanol for 3h; Reflux; Resolution of racemate;	83%

(+)-dibenzoyl-D-tartaric acid monohydrate (80822-15-7) → (+/-)-Trans-4-[6-chloro-3-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl]-1,2,2-trimethylpiperazine, maleate

Conditions	Yield
In ethyl acetate; acetone
In ethyl acetate; acetone

2-bromophenylacetic acid (4870-65-9) + copper(II) acetate monohydrate (6046-93-1) + (+)-dibenzoyl-D-tartaric acid monohydrate (80822-15-7) → Cu(D-O,O'-dibenzoyltartaric acid(1-))(α-bromophenylacetate)*1.5H2O

Conditions	Yield
In acetonitrile to soln. D-O,O'-dibenzoyltartaric acid*H2O and α-halocarboxylic acid in MeCN at 40°C was added Cu(OAc)2*H2O, mixt. was stirred for 7 days; ppt. was filtered, washed with MeCN, air-dried overnight at room temp.; elem. anal.;

2-bromo-2-(4-chlorophenyl)acetic acid (3381-73-5) + copper(II) acetate monohydrate (6046-93-1) + (+)-dibenzoyl-D-tartaric acid monohydrate (80822-15-7) + acetonitrile (75-05-8) → Cu2(D-O,O'-dibenzoyltartrate)(α-bromo-4-chlorophenylacetate)(OAc)(H2O)2

Conditions	Yield
In acetonitrile to soln. D-O,O'-dibenzoyltartaric acid*H2O and α-halocarboxylic acid in MeCN at 40°C was added Cu(OAc)2*H2O, mixt. was stirred for 7 days; ppt. was filtered, washed with MeCN, air-dried overnight at room temp.; elem. anal.;

copper(II) acetate monohydrate (6046-93-1) + rac-α-chloro-2-chlorophenylacetic acid (109904-41-8) + (+)-dibenzoyl-D-tartaric acid monohydrate (80822-15-7) + acetonitrile (75-05-8) → [Cu2(D-O,O'-dibenzoyltartrate)((R)-α-chloro-2-chlorophenylacetate)(OAc)(H2O)2]*1.5MeCN

Conditions	Yield
In acetonitrile to soln. D-O,O'-dibenzoyltartaric acid*H2O and α-halocarboxylic acid in MeCN at 40°C was added Cu(OAc)2*H2O, mixt. was stirred for 7-14 days; ppt. was filtered, washed with MeCN, air-dried overnight at room temp.; elem. anal.;

rac-α-chloro-2-fluorophenylacetic acid + copper(II) acetate monohydrate (6046-93-1) + (+)-dibenzoyl-D-tartaric acid monohydrate (80822-15-7) + acetonitrile (75-05-8) → [Cu2(D-O,O'-dibenzoyltartrate)((R)-α-chloro-2-fluorophenylacetate)(OAc)(H2O)2]*1.5MeCN

Conditions	Yield
In acetonitrile to soln. D-O,O'-dibenzoyltartaric acid*H2O and α-halocarboxylic acid in MeCN at 40°C was added Cu(OAc)2*H2O, mixt. was stirred for 7-14 days; ppt. was filtered, washed with MeCN, air-dried overnight at room temp.; elem. anal.;

(R)-α-bromo-2-chlorophenylacetic acid (256398-61-5) + copper(II) acetate monohydrate (6046-93-1) + (+)-dibenzoyl-D-tartaric acid monohydrate (80822-15-7) → Cu2(D-O,O'-dibenzoyltartrate)((R)-α-bromo-2-chlorophenylacetate)(OAc)(H2O)2

Conditions	Yield
In ethanol; water EtOH-H2O (3:1), 40°C, 1 day; cooling to -10°C; elem. anal.;

(R)-α-bromo-2-chlorophenylacetic acid (256398-61-5) + copper(II) acetate monohydrate (6046-93-1) + (+)-dibenzoyl-D-tartaric acid monohydrate (80822-15-7) + acetonitrile (75-05-8) → [Cu2(D-O,O'-dibenzoyltartrate)((R)-α-bromo-2-chlorophenylacetate)(OAc)(H2O)2]*1.5MeCN

Conditions	Yield
In acetonitrile to soln. D-O,O'-dibenzoyltartaric acid*H2O and α-halocarboxylic acid in MeCN at 40°C was added Cu(OAc)2*H2O, mixt. was stirred for 30 min;

α-bromo-2-chlorophenyl acetic acid (29270-30-2) + copper(II) acetate monohydrate (6046-93-1) + (+)-dibenzoyl-D-tartaric acid monohydrate (80822-15-7) + acetonitrile (75-05-8) → [Cu2(D-O,O'-dibenzoyltartrate)((R)-α-bromo-2-chlorophenylacetate)(OAc)(H2O)2]*1.5MeCN

Conditions	Yield
In acetonitrile soln. D-O,O'-dibenzoyltartaric acid*H2O, α-halocarboxylic acid, and Cu(OAc)2*H2O in MeCN was stirred at 25-50°C for 7 days; ppt. was filtered, washed with MeCN, air-dried overnight at room temp.; elem. anal.;
In water; acetonitrile soln. D-O,O'-dibenzoyltartaric acid*H2O, α-halocarboxylic acid, and Cu(OAc)2*H2O in aq. MeCN was stirred at 40°C for 5 days; ppt. was filtered, washed with MeCN, air-dried overnight at room temp.;

rac-α-bromo-2-bromophenylacetic acid + copper(II) acetate monohydrate (6046-93-1) + (+)-dibenzoyl-D-tartaric acid monohydrate (80822-15-7) + acetonitrile (75-05-8) → [Cu2(D-O,O'-dibenzoyltartrate)((R)-α-bromo-2-bromophenylacetate)(OAc)(H2O)2]*2MeCN

Conditions	Yield
In water; acetonitrile to soln. D-O,O'-dibenzoyltartaric acid*H2O and α-halocarboxylic acid in aq. MeCN at 40°C was added Cu(OAc)2*H2O, mixt. was stirred for 5 days; ppt. was filtered, washed with MeCN, air-dried overnight at room temp.; elem. anal.;

copper(II) acetate monohydrate (6046-93-1) + (+)-dibenzoyl-D-tartaric acid monohydrate (80822-15-7) + rac-α-bromo-2-fluorophenylacetic acid (134770-09-5, 873838-82-5) + acetonitrile (75-05-8) → [Cu2(D-O,O'-dibenzoyltartrate)((R)-α-bromo-2-fluorophenylacetate)(OAc)(H2O)2]*1.5MeCN

Conditions	Yield
In acetonitrile to soln. D-O,O'-dibenzoyltartaric acid*H2O and α-halocarboxylic acid in MeCN at 40°C was added Cu(OAc)2*H2O, mixt. was stirred for 7 days; ppt. was filtered, washed with MeCN, air-dried overnight at room temp.; elem. anal.;
In water; acetonitrile to soln. D-O,O'-dibenzoyltartaric acid*H2O and α-halocarboxylic acid in aq. MeCN at 40°C was added Cu(OAc)2*H2O, mixt. was stirred for 5 days;