Product Name

  • Name

    L-(+)-TARTARIC ACID DI-N-BUTYL ESTER

  • EINECS 201-784-9
  • CAS No. 87-92-3
  • Article Data4
  • CAS DataBase
  • Density 1.09 g/cm3
  • Solubility 4.827g/L(temperature not stated)
  • Melting Point 20-22 °C
  • Formula C12H22O6
  • Boiling Point 182 °C (11 mmHg)
  • Molecular Weight 262.303
  • Flash Point 167 °C
  • Transport Information
  • Appearance clear colourless to yellowish liquid after melting
  • Safety 24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 87-92-3 (L-(+)-TARTARIC ACID DI-N-BUTYL ESTER)
  • Hazard Symbols
  • Synonyms Butanedioicacid, 2,3-dihydroxy- (2R,3R)-, dibutyl ester (9CI);Butanedioic acid,2,3-dihydroxy- [R-(R*,R*)]-, dibutyl ester;Tartaric acid, dibutyl ester(6CI,7CI,8CI);(+)-Dibutyl tartrate;(+)-Tartaric acid dibutyl ester;(2R,3R)-Di-n-butyl tartrate;(2R,3R)-Dibutyl tartrate;Dibutyl (+)-L-tartrate;Dibutyl (R,R)-tartrate;Dibutyl L-(+)-tartrate;Dibutyl L-tartrate;Dibutyltartrate;ENT 396;L-(+)-Tartaric acid dibutyl ester;
  • PSA 93.06000
  • LogP 0.39480

Synthetic route

L-Tartaric acid
87-69-4

L-Tartaric acid

butan-1-ol
71-36-3

butan-1-ol

(+)-(2R,3R)-dibutyl tartrate
87-92-3

(+)-(2R,3R)-dibutyl tartrate

Conditions
ConditionsYield
With H+ resin; Zerolit 225 In benzene for 8h; Heating;68%
With thionyl chloride
tartaric acid
87-69-4

tartaric acid

butan-1-ol
71-36-3

butan-1-ol

(+)-(2R,3R)-dibutyl tartrate
87-92-3

(+)-(2R,3R)-dibutyl tartrate

Conditions
ConditionsYield
durch Destillation;
dibenzyl (2R,3R)-2,3-dihydroxybutanedioate
622-00-4

dibenzyl (2R,3R)-2,3-dihydroxybutanedioate

butan-1-ol
71-36-3

butan-1-ol

(+)-(2R,3R)-dibutyl tartrate
87-92-3

(+)-(2R,3R)-dibutyl tartrate

Conditions
ConditionsYield
In various solvent(s) at 39℃; for 24h; lipase from Pseudomonas fluorescens;86.2 % Spectr.
(+)-(2R,3R)-dibutyl tartrate
87-92-3

(+)-(2R,3R)-dibutyl tartrate

potassium bis(di-n-butyl-L-tartrate(2-)-O,O')borate

potassium bis(di-n-butyl-L-tartrate(2-)-O,O')borate

Conditions
ConditionsYield
With boric acid; potassium hydrogencarbonate In water at 20℃; Heating;100%
(+)-(2R,3R)-dibutyl tartrate
87-92-3

(+)-(2R,3R)-dibutyl tartrate

chloroacetyl chloride
79-04-9

chloroacetyl chloride

(2R,3R)-2,3-Bis-(2-chloro-acetoxy)-succinic acid dibutyl ester
226710-53-8

(2R,3R)-2,3-Bis-(2-chloro-acetoxy)-succinic acid dibutyl ester

Conditions
ConditionsYield
With pyridine In chloroform for 5h; Ambient temperature;84.6%
(+)-(2R,3R)-dibutyl tartrate
87-92-3

(+)-(2R,3R)-dibutyl tartrate

Dibenzyl N,N-diisopropylphosphoramidite
108549-23-1

Dibenzyl N,N-diisopropylphosphoramidite

dibutyl-2,3-bis(dibenzylphospho)-L-tartrate
1610451-59-6

dibutyl-2,3-bis(dibenzylphospho)-L-tartrate

Conditions
ConditionsYield
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

(+)-(2R,3R)-dibutyl tartrate

6-methoxy-2-propionylnaphthalene
2700-47-2

6-methoxy-2-propionylnaphthalene

(4R,5R)-2-ethyl-2-(6-methoxy-2-naphthyl)-1,3-dioxolane-4,5-dicarboxylic acid di-n-butyl ester
105785-45-3

(4R,5R)-2-ethyl-2-(6-methoxy-2-naphthyl)-1,3-dioxolane-4,5-dicarboxylic acid di-n-butyl ester

Conditions
ConditionsYield
With methanesulfonic acid; Tributyl orthoformate at 100℃; for 1h;80%
dimethyltitanocene
1271-66-5

dimethyltitanocene

(+)-(2R,3R)-dibutyl tartrate
87-92-3

(+)-(2R,3R)-dibutyl tartrate

[(C5H5)2Ti(CH3)]2((OCH(COOC4H9))2)

[(C5H5)2Ti(CH3)]2((OCH(COOC4H9))2)

Conditions
ConditionsYield
In diethyl ether; dichloromethane elem. anal.;76%
(+)-(2R,3R)-dibutyl tartrate
87-92-3

(+)-(2R,3R)-dibutyl tartrate

(4R,5R)-2-Chloro-[1,3,2]dioxaphospholane-4,5-dicarboxylic acid dibutyl ester

(4R,5R)-2-Chloro-[1,3,2]dioxaphospholane-4,5-dicarboxylic acid dibutyl ester

Conditions
ConditionsYield
With pyridine; phosphorus trichloride In diethyl ether at 0℃; for 6h;54%
(+)-(2R,3R)-dibutyl tartrate
87-92-3

(+)-(2R,3R)-dibutyl tartrate

butyl glyoxalate
6295-06-3

butyl glyoxalate

Conditions
ConditionsYield
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

(+)-(2R,3R)-dibutyl tartrate

threitol
2319-57-5

threitol

Conditions
ConditionsYield
With tetrahydrofuran; lithium aluminium tetrahydride; diethyl ether
(+)-(2R,3R)-dibutyl tartrate
87-92-3

(+)-(2R,3R)-dibutyl tartrate

benzaldehyde
100-52-7

benzaldehyde

O,O'-benzylidene-Lg-tartaric acid dibutyl ester

O,O'-benzylidene-Lg-tartaric acid dibutyl ester

Conditions
ConditionsYield
With phosphorus pentoxide
With toluene-4-sulfonic acid In benzene Dean-Stark; Reflux;
(+)-(2R,3R)-dibutyl tartrate
87-92-3

(+)-(2R,3R)-dibutyl tartrate

benzoyl chloride
98-88-4

benzoyl chloride

di-O-benzoyl-Lg-tartaric acid dibutyl ester

di-O-benzoyl-Lg-tartaric acid dibutyl ester

Conditions
ConditionsYield
at 140 - 150℃;
perillene
539-52-6

perillene

(+)-(2R,3R)-dibutyl tartrate
87-92-3

(+)-(2R,3R)-dibutyl tartrate

(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

(4R,5R)-2-((E)-4-Furan-3-yl-1-methyl-but-1-enyl)-[1,3]dioxolane-4,5-dicarboxylic acid dibutyl ester

Conditions
ConditionsYield
1) SeO2, tert-C4H9OOH, CH2Cl2; Multistep reaction;
(+)-(2R,3R)-dibutyl tartrate
87-92-3

(+)-(2R,3R)-dibutyl tartrate

thymidyl acetic acid
20924-05-4

thymidyl acetic acid

(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

(2R,3R)-2,3-Bis-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetoxy]-succinic acid dibutyl ester

Conditions
ConditionsYield
With 1,1'-carbonyldiimidazole
(+)-(2R,3R)-dibutyl tartrate
87-92-3

(+)-(2R,3R)-dibutyl tartrate

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

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

Conditions
ConditionsYield
With sodium acetate; phosphorus trichloride at 20℃; for 3h;
(+)-(2R,3R)-dibutyl tartrate
87-92-3

(+)-(2R,3R)-dibutyl tartrate

(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

(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
ConditionsYield
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)-dibutyl tartrate

(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

(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
ConditionsYield
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)-dibutyl tartrate

(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

(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
ConditionsYield
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)-dibutyl tartrate

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

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

Conditions
ConditionsYield
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

(+)-(2R,3R)-dibutyl tartrate

(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

(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
ConditionsYield
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

(+)-(2R,3R)-dibutyl tartrate

(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

(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
ConditionsYield
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

(+)-(2R,3R)-dibutyl tartrate

(Z)-4-Ethyl-2-hydroxy-hex-4-enoic acid butyl ester

(Z)-4-Ethyl-2-hydroxy-hex-4-enoic acid butyl ester

Conditions
ConditionsYield
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

(+)-(2R,3R)-dibutyl tartrate

(E)-4-ethyl-2-hydroxy-4-hexenoate

(E)-4-ethyl-2-hydroxy-4-hexenoate

Conditions
ConditionsYield
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

(+)-(2R,3R)-dibutyl tartrate

C26H34N4O12*C20H24N6O5
129784-31-2

C26H34N4O12*C20H24N6O5

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: carbonyldiimidazole
2: acetone; CH2Cl2 / Irradiation
View Scheme
(+)-(2R,3R)-dibutyl tartrate
87-92-3

(+)-(2R,3R)-dibutyl tartrate

C26H34N4O12*C23H30N6O4
129784-30-1

C26H34N4O12*C23H30N6O4

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: carbonyldiimidazole
2: acetone; CH2Cl2 / Irradiation
View Scheme
(+)-(2R,3R)-dibutyl tartrate
87-92-3

(+)-(2R,3R)-dibutyl tartrate

C26H34N4O12*C24H32N6O4
129784-29-8

C26H34N4O12*C24H32N6O4

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: carbonyldiimidazole
2: acetone; CH2Cl2 / Irradiation
3: CDCl3
View Scheme
(+)-(2R,3R)-dibutyl tartrate
87-92-3

(+)-(2R,3R)-dibutyl tartrate

C26H34N4O12
129697-23-0

C26H34N4O12

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: carbonyldiimidazole
2: acetone; CH2Cl2 / Irradiation
View Scheme
(+)-(2R,3R)-dibutyl tartrate
87-92-3

(+)-(2R,3R)-dibutyl tartrate

Tetrabutyl (4R,4'R,5R,5'R)-2,2'-bi-1,3,2-dioxaborolane-4,4',5,5'-tetracarboxylate
230299-40-8

Tetrabutyl (4R,4'R,5R,5'R)-2,2'-bi-1,3,2-dioxaborolane-4,4',5,5'-tetracarboxylate

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

Dibutyl L-(+)-tartrate Specification

The Dibutyl L-(+)-tartrate, with the CAS registry number 87-92-3, is also known as Butanedioic acid, 2,3-dihydroxy- (2R,3R)-, 1,4-dibutyl ester and Butanedioic acid, 2,3-dihydroxy- (2R,3R)-, dibutyl ester. Its EINECS number is 201-784-9. This chemical's molecular formula is C12H22O6 and formula weight is 262.3. What's more, both its IUPAC name and systematic name are the same which is called Dibutyl 2,3-dihydroxybutanedioate. This chemical is clear colourless to yellowish liquid after melting.

Physical properties about this chemical are: (1)ACD/LogP: 1.84; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 6; (4)#H bond donors: 2; (5)#Freely Rotating Bonds: 13; (6)Polar Surface Area: 71.06 Å2; (7)Index of Refraction: 1.471; (8)Molar Refractivity: 64.18 cm3; (9)Molar Volume: 229.3 cm3; (10)Surface Tension: 42.9 dyne/cm; (11)Density: 1.143 g/cm3; (12)Flash Point: 119.2 °C; (13)Enthalpy of Vaporization: 65.1 kJ/mol; (14)Boiling Point: 320 °C at 760 mmHg; (15)Melting Point: 20-22 °C; (16)Vapour Pressure: 2.66E-05 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCCCOC(=O)C(C(C(=O)OCCCC)O)O
(2)InChI: InChI=1S/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
(3)InChIKey: PCYQQSKDZQTOQG-UHFFFAOYSA-N

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