87-92-3

Basic information

• Product Name: L-(+)-TARTARIC ACID DI-N-BUTYL ESTER
• Synonyms: L-(+)-TARTARIC ACID DIBUTYL ESTER;L-(+)-TARTARIC ACID DI-N-BUTYL ESTER;DI-N-BUTYL L-(+)-TARTRATE;DIBUTYL TARTRATE;DIBUTYL L-TARTRATE;L-(+)-DIBUTYL TARTRATE;(2R,3R)-(+)-DI-N-BUTYL TARTRATE;N-BUTYL TARTRATE
• CAS NO: 87-92-3
• Molecular Formula: C₁₂H₂₂O₆
• Molecular Weight: 262.3
• EINECS: 201-784-9
• Mol File: 87-92-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 20-22 °C
• Boiling Point: 182 °C (11 mmHg)
• Flash Point: 167 °C
• Appearance: clear colourless to yellowish liquid after melting
• Density: 1.09
• Refractive Index: 1.446-1.448
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 11.42±0.20(Predicted)
• Water Solubility: 4.827g/L(temperature not stated)
• CAS DataBase Reference: L-(+)-TARTARIC ACID DI-N-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: L-(+)-TARTARIC ACID DI-N-BUTYL ESTER(87-92-3)
• EPA Substance Registry System: L-(+)-TARTARIC ACID DI-N-BUTYL ESTER(87-92-3)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 87-92-3(Hazardous Substances Data)

Usage

Uses

L-(+)-TARTARIC ACID DI-N-BUTYL ESTER is used as resolving agent

InChI:InChI=1/C12H22O6/c1-3-5-7-17-11(15)9(13)10(14)12(16)18-8-6-4-2/h9-10,13-14H,3-8H2,1-2H3/t9-,10-/m1/s1

Synthetic route

L-Tartaric acid (87-69-4) + butan-1-ol (71-36-3) → (+)-(2R,3R)-dibutyl tartrate (87-92-3)

Conditions	Yield
With H+ resin; Zerolit 225 In benzene for 8h; Heating;	68%
With thionyl chloride

tartaric acid (87-69-4) + butan-1-ol (71-36-3) → (+)-(2R,3R)-dibutyl tartrate (87-92-3)

Conditions	Yield
durch Destillation;

dibenzyl (2R,3R)-2,3-dihydroxybutanedioate (622-00-4) + butan-1-ol (71-36-3) → (+)-(2R,3R)-dibutyl tartrate (87-92-3)

Conditions	Yield
In various solvent(s) at 39℃; for 24h; lipase from Pseudomonas fluorescens;	86.2 % Spectr.

(+)-(2R,3R)-dibutyl tartrate (87-92-3) → potassium bis(di-n-butyl-L-tartrate(2-)-O,O')borate

Conditions	Yield
With boric acid; potassium hydrogencarbonate In water at 20℃; Heating;	100%

(+)-(2R,3R)-dibutyl tartrate (87-92-3) + chloroacetyl chloride (79-04-9) → (2R,3R)-2,3-Bis-(2-chloro-acetoxy)-succinic acid dibutyl ester (226710-53-8)

Conditions	Yield
With pyridine In chloroform for 5h; Ambient temperature;	84.6%

(+)-(2R,3R)-dibutyl tartrate (87-92-3) + Dibenzyl N,N-diisopropylphosphoramidite (108549-23-1) → dibutyl-2,3-bis(dibenzylphospho)-L-tartrate (1610451-59-6)

Conditions	Yield
Stage #1: (+)-(2R,3R)-dibutyl tartrate; Dibenzyl N,N-diisopropylphosphoramidite With 1H-tetrazole at 20℃; for 24h; Stage #2: With 3-chloro-benzenecarboperoxoic acid at -40 - 20℃; for 12h;	84%

(+)-(2R,3R)-dibutyl tartrate (87-92-3) + 6-methoxy-2-propionylnaphthalene (2700-47-2) → (4R,5R)-2-ethyl-2-(6-methoxy-2-naphthyl)-1,3-dioxolane-4,5-dicarboxylic acid di-n-butyl ester (105785-45-3)

Conditions	Yield
With methanesulfonic acid; Tributyl orthoformate at 100℃; for 1h;	80%

dimethyltitanocene (1271-66-5) + (+)-(2R,3R)-dibutyl tartrate (87-92-3) → [(C5H5)2Ti(CH3)]2((OCH(COOC4H9))2)

Conditions	Yield
In diethyl ether; dichloromethane elem. anal.;	76%

(+)-(2R,3R)-dibutyl tartrate (87-92-3) → (4R,5R)-2-Chloro-[1,3,2]dioxaphospholane-4,5-dicarboxylic acid dibutyl ester

Conditions	Yield
With pyridine; phosphorus trichloride In diethyl ether at 0℃; for 6h;	54%

(+)-(2R,3R)-dibutyl tartrate (87-92-3) → butyl glyoxalate (6295-06-3)

Conditions	Yield
With sodium periodate In water for 40h;	50%
With sodium periodate
With lead(IV) acetate; benzene
With sodium periodate In water; isopropyl alcohol Heating;

(+)-(2R,3R)-dibutyl tartrate (87-92-3) → threitol (2319-57-5)

Conditions	Yield
With tetrahydrofuran; lithium aluminium tetrahydride; diethyl ether

(+)-(2R,3R)-dibutyl tartrate (87-92-3) + benzaldehyde (100-52-7) → O,O'-benzylidene-Lg-tartaric acid dibutyl ester

Conditions	Yield
With phosphorus pentoxide
With toluene-4-sulfonic acid In benzene Dean-Stark; Reflux;

(+)-(2R,3R)-dibutyl tartrate (87-92-3) + benzoyl chloride (98-88-4) → di-O-benzoyl-Lg-tartaric acid dibutyl ester

Conditions	Yield
at 140 - 150℃;

perillene (539-52-6) + (+)-(2R,3R)-dibutyl tartrate (87-92-3) → (4R,5R)-2-((E)-4-Furan-3-yl-1-methyl-but-1-enyl)-[1,3]dioxolane-4,5-dicarboxylic acid dibutyl ester (125029-42-7)

Conditions	Yield
1) SeO2, tert-C4H9OOH, CH2Cl2; Multistep reaction;

(+)-(2R,3R)-dibutyl tartrate (87-92-3) + thymidyl acetic acid (20924-05-4) → (2R,3R)-2,3-Bis-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetoxy]-succinic acid dibutyl ester (129697-22-9)

Conditions	Yield
With 1,1'-carbonyldiimidazole

(+)-(2R,3R)-dibutyl tartrate (87-92-3) → (2R,3R,7R,8R)-1,4,6,9-Tetraoxa-5λ5-phospha-spiro[4.4]nonane-2,3,7,8-tetracarboxylic acid tetrabutyl ester

Conditions	Yield
With sodium acetate; phosphorus trichloride at 20℃; for 3h;

(+)-(2R,3R)-dibutyl tartrate (87-92-3) → (2R,3R,7R,8R)-5-(Dodecylamino-phenyl-methyl)-1,4,6,9-tetraoxa-5λ5-phospha-spiro[4.4]nonane-2,3,7,8-tetracarboxylic acid tetrabutyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: PCl3; NaOAc / 3 h / 20 °C 2: 240 h / 20 °C View Scheme

(+)-(2R,3R)-dibutyl tartrate (87-92-3) → (2R,3R,7R,8R)-5-(Hexadecylamino-phenyl-methyl)-1,4,6,9-tetraoxa-5λ5-phospha-spiro[4.4]nonane-2,3,7,8-tetracarboxylic acid tetrabutyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: PCl3; NaOAc / 3 h / 20 °C 2: 240 h / 20 °C View Scheme

(+)-(2R,3R)-dibutyl tartrate (87-92-3) → (2R,3R,7R,8R)-5-(Octadecylamino-phenyl-methyl)-1,4,6,9-tetraoxa-5λ5-phospha-spiro[4.4]nonane-2,3,7,8-tetracarboxylic acid tetrabutyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: PCl3; NaOAc / 3 h / 20 °C 2: 240 h / 20 °C View Scheme

(+)-(2R,3R)-dibutyl tartrate (87-92-3) → (4'R,5'R)-25,27-dihydroxy-26,28-(4',5'-dibutoxycarbonyl-3',6'-dioxa-2',7'-dioxooctylene)-dioxycalix<4>arene

Conditions	Yield
Multi-step reaction with 2 steps 1: 84.6 percent / pyridine / CHCl3 / 5 h / Ambient temperature 2: 24.8 percent / K2CO3, KI / acetone; toluene / 48 h / Heating View Scheme

(+)-(2R,3R)-dibutyl tartrate (87-92-3) → (4'R,5'R)-5,11,17,23-tetra-tert-butyl-25,27-dihydroxy-26,28-(4',5'-dibutoxycarbonyl-3',6'-dioxa-2',7'-dioxooctylene)-dioxycalix<4>arene

Conditions	Yield
Multi-step reaction with 2 steps 1: 84.6 percent / pyridine / CHCl3 / 5 h / Ambient temperature 2: 10.5 percent / K2CO3, KI / acetone; toluene / 48 h / Heating View Scheme

(+)-(2R,3R)-dibutyl tartrate (87-92-3) → (4'R,5'R)-5,11,17,23-tetra-allyl-25,27-dihydroxy-26,28-(4',5'-dibutoxycarbonyl-3',6'-dioxa-2',7'-dioxooctylene)-dioxycalix<4>arene

Conditions	Yield
Multi-step reaction with 2 steps 1: 84.6 percent / pyridine / CHCl3 / 5 h / Ambient temperature 2: 9.6 percent / K2CO3, KI / acetone; toluene / 48 h / Heating View Scheme

(+)-(2R,3R)-dibutyl tartrate (87-92-3) → (Z)-4-Ethyl-2-hydroxy-hex-4-enoic acid butyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 50 percent / sodium periodate / H2O / 40 h 2: diisopropoxytitanium(IV) dichloride, (+/-)-1,1'-bi-2-naphthol, 4A / CH2Cl2 / -70 deg C - room temperature, room temperature 24 h View Scheme

(+)-(2R,3R)-dibutyl tartrate (87-92-3) → (E)-4-ethyl-2-hydroxy-4-hexenoate

Conditions	Yield
Multi-step reaction with 2 steps 1: 50 percent / sodium periodate / H2O / 40 h 2: diisopropoxytitanium(IV) dichloride, (+/-)-1,1'-bi-2-naphthol, 4A / CH2Cl2 / -70 deg C - room temperature, room temperature 24 h View Scheme

(+)-(2R,3R)-dibutyl tartrate (87-92-3) → C26H34N4O12*C20H24N6O5 (129784-31-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: carbonyldiimidazole 2: acetone; CH2Cl2 / Irradiation View Scheme

(+)-(2R,3R)-dibutyl tartrate (87-92-3) → C26H34N4O12*C23H30N6O4 (129784-30-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: carbonyldiimidazole 2: acetone; CH2Cl2 / Irradiation View Scheme

(+)-(2R,3R)-dibutyl tartrate (87-92-3) → C26H34N4O12*C24H32N6O4 (129784-29-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: carbonyldiimidazole 2: acetone; CH2Cl2 / Irradiation 3: CDCl3 View Scheme

(+)-(2R,3R)-dibutyl tartrate (87-92-3) → C26H34N4O12 (129697-23-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: carbonyldiimidazole 2: acetone; CH2Cl2 / Irradiation View Scheme

(+)-(2R,3R)-dibutyl tartrate (87-92-3) → Tetrabutyl (4R,4'R,5R,5'R)-2,2'-bi-1,3,2-dioxaborolane-4,4',5,5'-tetracarboxylate (230299-40-8)

Conditions	Yield
With tetrakis(dimethylamido)diborane In toluene at 100℃; for 1.2h;

Upstream product

• 87-69-4 tartaric acid 
• 71-36-3 butan-1-ol 
• 87-69-4 L-Tartaric acid 
• 622-00-4 dibenzyl (2R,3R)-2,3-dihydroxybutanedioate 

Downstream Products

• 74479-40-6 butyl {(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethyl)phenyl-3,7-dimethylnona-2,4,6.8}tetraenoate 
• 1610451-59-6 dibutyl-2,3-bis(dibenzylphospho)-L-tartrate 
• 6295-06-3 butyl glyoxalate 
• 2319-57-5 threitol 

Relevant articles and documents

Synthesis of (E)-1-bromo-3-ethyl-3-pentene

The synthesis of (E)-1-bromo-3-ethyl-3-pentene 1 is described in which the (E)-stereochemistry of the alkene is set up via a diastereoselective glyoxylate ene reaction.

A CONVENIENT METHOD FOR ENZYMATIC BENZYL-ALKYL TRANSESTERIFICATION UNDER MILD NEUTRAL CONDITIONS

Lipases from Candida cylindracea and from Pseudomonas fluorescens efficiently catalyse the benzyl to alkyl transesterification in organic solvents under mild conditions in nearly quantitative yields.