Product Name

  • Name

    L(+)-Diethyl L-tartrate

  • EINECS 201-783-3
  • CAS No. 87-91-2
  • Article Data50
  • CAS DataBase
  • Density 1.262 g/cm3
  • Solubility insoluble in water
  • Melting Point 17 °C
  • Formula C8H14O6
  • Boiling Point 280 °C at 760 mmHg
  • Molecular Weight 206.196
  • Flash Point 93.3 °C
  • Transport Information
  • Appearance Colorless to light yellow liquid
  • Safety 24/25-36-26
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 87-91-2 (L(+)-Diethyl L-tartrate)
  • Hazard Symbols IrritantXi
  • Synonyms Butanedioicacid, 2,3-dihydroxy- (2R,3R)-, diethyl ester (9CI);Butanedioic acid,2,3-dihydroxy-[R-(R*,R*)]-, diethyl ester;Tartaric acid, diethyl ester(6CI,7CI,8CI);(+)-(R,R)-Diethyl tartrate;(R,R)-Diethyl tartrate;(R,R)-Tartaric acid diethyl ester;Diethyl (+)-tartrate;Diethyl(2R,3R)-(+)-tartrate;Diethyl (2R,3R)-2,3-dihydroxysuccinate;Diethyl(2R,3R)-tartrate;Diethyl (R,R)-tartrate;Diethyl1,2-dihydroxy-1,2-ethanedicarboxylate;Diethyl L-(+)-tartrate;DiethylL-(+)-tartrate;Diethyl L-tartarate;Diethyl L-tartrate;Diethyl tartrate;Ethyl(+)-tartrate;Ethyl tartrate;L-Diethyl tartrate;L-Tartaric acid diethylester;NSC 44808;NSC 8878;L(+)-Diethyl L-Tartrate;
  • PSA 93.06000
  • LogP -1.16560

Synthetic route

ethanol
64-17-5

ethanol

L-Tartaric acid
87-69-4

L-Tartaric acid

diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

Conditions
ConditionsYield
With thionyl chloride100%
With methanesulfonic acid at 30 - 35℃; for 12h;99%
With thionyl chloride at 0 - 50℃; for 3.5h; Temperature;96.2%
ethanol
64-17-5

ethanol

(R,R)-tartaric acid ethyl ester
608-89-9

(R,R)-tartaric acid ethyl ester

diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

Conditions
ConditionsYield
at 160℃;
ethyl iodide
75-03-6

ethyl iodide

diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

Conditions
ConditionsYield
With silver tartrate
ethanol
64-17-5

ethanol

tartaric acid
87-69-4

tartaric acid

diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

diethyl Fumarate
623-91-6

diethyl Fumarate

diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

Conditions
ConditionsYield
With diethyl ether; dihydrogen peroxide Irradiation.mit rechts-zirkular polarisiertem UV-Licht entsteht ein schwach rechtsdrehendes Praeparat;
ethanol
64-17-5

ethanol

dibenzyl (2R,3R)-2,3-dihydroxybutanedioate
622-00-4

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

diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

Conditions
ConditionsYield
In various solvent(s) at 39℃; for 168h; lipase from Pseudomonas fluorescens;96.5 % Spectr.
ethanol
64-17-5

ethanol

L-Tartaric acid
87-69-4

L-Tartaric acid

dehydrocholic acid
81-23-2

dehydrocholic acid

A

diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

B

3,7,12-trioxo-5β-cholan-24-oic acid ethyl ester
52718-49-7

3,7,12-trioxo-5β-cholan-24-oic acid ethyl ester

Conditions
ConditionsYield
With methanesulfonic acid for 5 - 6h; Heating / reflux;
...Expand
octanol
111-87-5

octanol

C12H24Cl2O6Si2

C12H24Cl2O6Si2

A

diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

B

dimethyl-bis-octyloxy-silane
18536-88-4

dimethyl-bis-octyloxy-silane

C

chloro(dimethyl)octyloxysilane
52322-14-2

chloro(dimethyl)octyloxysilane

Conditions
ConditionsYield
With gallium(III) trichloride at 20℃; for 6h; Inert atmosphere;
...Expand
(+/-)-diethyl tartrate
57968-71-5

(+/-)-diethyl tartrate

A

diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

B

diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

Conditions
ConditionsYield
With (S)-aminopropyl alcohol(at)silica 1 In hexane; isopropyl alcohol at 20℃; for 1h; Purification / work up; Resolution of racemate; Inert atmosphere;A n/a
B n/a
L-Tartaric acid
87-69-4

L-Tartaric acid

diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

Conditions
ConditionsYield
With hydrogenchloride In ethanol
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

dimethyl sulfate
77-78-1

dimethyl sulfate

(+)-(2R,3R)-diethyl di-O-methyltartrate
27957-93-3

(+)-(2R,3R)-diethyl di-O-methyltartrate

Conditions
ConditionsYield
With sodium hydride In diethyl ether at 0 - 20℃; Inert atmosphere;100%
With sodium hydride In diethyl ether at 0 - 20℃; Inert atmosphere;100%
With sodium hydride In diethyl ether at 0 - 20℃;100%
With sodium hydride In diethyl ether
Trimethyl orthoacetate
1445-45-0

Trimethyl orthoacetate

diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

diethyl (4R)-trans-2-methoxy-2-methyl-1,3-dioxolan-4,5-dicarboxylate
134745-01-0

diethyl (4R)-trans-2-methoxy-2-methyl-1,3-dioxolan-4,5-dicarboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 12h;100%
With sulfuric acid In benzene at 80℃;98%
Dimethoxymethane
109-87-5

Dimethoxymethane

diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

(+)-(2R,3R)-diethyl 2,3-bismethoxymethoxybutanedioate
100449-52-3

(+)-(2R,3R)-diethyl 2,3-bismethoxymethoxybutanedioate

Conditions
ConditionsYield
With phosphorus pentaoxide In chloroform for 2.5h; Ambient temperature;100%
With phosphorus pentoxide In dichloromethane for 5h; Ambient temperature;100%
With phosphorus pentoxide In chloroform for 2h; Alkylation;97%
With phosphorus pentoxide In dichloromethane96%
With phosphorus pentoxide In dichloromethane
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

diethyl (4R,5R)-1,3,2-dioxathiolane-4,5-dicarboxylate 2-oxide
136087-36-0

diethyl (4R,5R)-1,3,2-dioxathiolane-4,5-dicarboxylate 2-oxide

Conditions
ConditionsYield
With thionyl chloride; N,N-dimethyl-formamide at 50℃; for 1h;100%
With thionyl chloride In tetrachloromethane for 2h; Heating;
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 0 - 50℃; for 2.5h;
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(2R,3R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-succinic acid diethyl ester
124224-83-5

(2R,3R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-succinic acid diethyl ester

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 35℃; for 14h;100%
With 1H-imidazole In N,N-dimethyl-formamide at 60℃; for 12h;100%
With 1H-imidazole In N,N-dimethyl-formamide95%
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

A

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate
59779-75-8

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

B

(4R,5R)-2,2-Dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid 4-ethyl ester 5-methyl ester

(4R,5R)-2,2-Dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid 4-ethyl ester 5-methyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 8h; Heating; Title compound not separated from byproducts.;A 100%
B n/a
for 2.5h; Heating;
...Expand
Dimethoxymethane
109-87-5

Dimethoxymethane

diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

trans-(4R,5R)-1,3-dioxolane-4,5-dicarboxylic acid diethyl ester
21154-13-2, 60077-28-3, 70561-17-0

trans-(4R,5R)-1,3-dioxolane-4,5-dicarboxylic acid diethyl ester

Conditions
ConditionsYield
With 3 A molecular sieve; Amberlyst 15 ion-exchange resin In ethyl acetate for 24h; Heating;100%
With boron trifluoride diethyl etherate In Isopropyl acetate100%
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

bis(diethyl-L-tartrateglycolato)diboron

bis(diethyl-L-tartrateglycolato)diboron

Conditions
ConditionsYield
With tetrakis(dimethylamido)diborane In toluene at 105℃; for 0.116667h;100%
1,1-dimethoxyethylene
922-69-0

1,1-dimethoxyethylene

diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

C16H30O10
1092455-59-8

C16H30O10

Conditions
ConditionsYield
at 20℃; for 0.5h; Inert atmosphere; neat (no solvent);100%
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

acetone
67-64-1

acetone

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate
59779-75-8

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

Conditions
ConditionsYield
With orthoformic acid triethyl ester99%
With hydrogenchloride; orthoformic acid triethyl ester In N,N-dimethyl-formamide at 20℃; for 72h;85%
boron trifluoride diethyl etherate at 23℃; for 5.5h; protection;80%
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

(+)-(2R,3R)-diethyl 2,3-bismethoxymethoxybutanedioate
100449-52-3

(+)-(2R,3R)-diethyl 2,3-bismethoxymethoxybutanedioate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 10h;99%
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere;99%
With N-ethyl-N,N-diisopropylamine In chloroform at 60℃; for 36h;79%
With N-ethyl-N,N-diisopropylamine for 48h; Ambient temperature;
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 25℃; for 18h;130 g
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

4-chlorobenzoylmethylenetriphenylphosphorane
1777-56-6

4-chlorobenzoylmethylenetriphenylphosphorane

(E)-ethyl 4-(4-chlorophenyl)-4-oxobut-2-enoate
89781-40-8

(E)-ethyl 4-(4-chlorophenyl)-4-oxobut-2-enoate

Conditions
ConditionsYield
Stage #1: diethyl (2R,3R)-tartrate With periodic acid In diethyl ether at 20 - 25℃; for 3h;
Stage #2: 4-chlorobenzoylmethylenetriphenylphosphorane In tetrahydrofuran; diethyl ether at 0 - 25℃; for 16h;		99%
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate
59779-75-8

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 8h; Heating;98%
With toluene-4-sulfonic acid for 8h; Reflux;98%
With toluene-4-sulfonic acid97%
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

butylboronic acid
4426-47-5

butylboronic acid

(4R,5S)-2-butyl-4,5-dicarboethoxy-1,3,2-diazaborolane

(4R,5S)-2-butyl-4,5-dicarboethoxy-1,3,2-diazaborolane

Conditions
ConditionsYield
In benzene equiv. amts. of tratrate and boronic acid were refluxed for 2 h with Dean-Stark trap; distn.; elem. anal.;98%
bis(cyclopentadienyl)dimethylzirconium(IV)
12636-72-5

bis(cyclopentadienyl)dimethylzirconium(IV)

diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

((C5H5)2Zr(C2H5OOCCH(O)CH(O)COOC2H5))2

((C5H5)2Zr(C2H5OOCCH(O)CH(O)COOC2H5))2

Conditions
ConditionsYield
In dichloromethane byproducts: CH4; (N2 or Ar); to a soln. of dimethylzirconocene added dropwise tartrate at room temp. over a period of 0.5 h; stirred for 1 h; evapd.; washed with pentane; dried in vacuo; elem. anal.;98%
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

diethyl 2,3-difluorosuccinate
868-24-6

diethyl 2,3-difluorosuccinate

Conditions
ConditionsYield
With sulfur tetrafluoride; hydrogen fluoride at 90℃; for 5h;97%
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

allyl bromide
106-95-6

allyl bromide

(2R,3R)-2,3-Bis-allyloxy-succinic acid diethyl ester
65973-54-8

(2R,3R)-2,3-Bis-allyloxy-succinic acid diethyl ester

Conditions
ConditionsYield
With silver(l) oxide In diethyl ether 2 h reflux in the dark, 1-3 d stirring;97%
With 18-crown-6 ether; tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran at 0 - 25℃; for 4h; Etherification;93%
With sodium hydride In tetrahydrofuran68%
Stage #1: diethyl (2R,3R)-tartrate With sodium hydride In tetrahydrofuran at 0℃; for 1h;
Stage #2: allyl bromide With 18-crown-6 ether; tetra-(n-butyl)ammonium iodide In tetrahydrofuran at 20℃; for 1.5h;
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

2-Methoxypropene
116-11-0

2-Methoxypropene

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate
59779-75-8

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane97%
With camphor-10-sulfonic acid In toluene at 20℃; for 5h;74%
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

methyl iodide
74-88-4

methyl iodide

(+)-(2R,3R)-diethyl di-O-methyltartrate
27957-93-3

(+)-(2R,3R)-diethyl di-O-methyltartrate

Conditions
ConditionsYield
With silver(l) oxide for 19h; Inert atmosphere; Schlenk technique; Reflux;96%
(i) TlOEt, benzene, (ii) /BRN= 969135/; Multistep reaction;
With silver(l) oxide
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

L-(R,R)-2-ethoxy-1,3-dioxolane-4,5-dicarboxylic acid diethyl ester
162491-34-1

L-(R,R)-2-ethoxy-1,3-dioxolane-4,5-dicarboxylic acid diethyl ester

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In ethanol at 130 - 140℃; for 2h;96%
With camphor-10-sulfonic acid In toluene at 95℃;95%
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

1,4-Cyclohexanedione
637-88-7

1,4-Cyclohexanedione

tetraethyl (2R,3R,10R,11R)-1,4,9,12-tetraoxadispiro[4.2.48.25]tetradecane-2,3,10,11-tetracarboxylate
216373-63-6

tetraethyl (2R,3R,10R,11R)-1,4,9,12-tetraoxadispiro[4.2.48.25]tetradecane-2,3,10,11-tetracarboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 30h; cyclocondensation; Heating;96%
With toluene-4-sulfonic acid In toluene for 120h; Condensation; Heating;92%
With boron trifluoride diethyl etherate In ethyl acetate at 0 - 20℃;55%
With boron trifluoride diethyl etherate In ethyl acetate at 0℃;
3,3-dimethoxypentane
25636-49-1

3,3-dimethoxypentane

diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

diethyl (4R,5R)-2,2-diethyl-1,3-dioxolane-4,5-dicarboxylate
68572-82-7

diethyl (4R,5R)-2,2-diethyl-1,3-dioxolane-4,5-dicarboxylate

Conditions
ConditionsYield
With 4 A molecular sieve; toluene-4-sulfonic acid In benzene for 3h; Heating;96%
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

(2R,3R)-2,3-dihydroxybutanedihydrazide
76585-39-2, 80081-45-4, 80081-47-6, 80081-49-8, 54789-92-3

(2R,3R)-2,3-dihydroxybutanedihydrazide

Conditions
ConditionsYield
With hydrazine In ethanol; water Heating / reflux;96%
With hydrazine hydrate In ethanol for 7h; Reflux;88%
With hydrazine hydrate In ethanol for 2h; Reflux;87%
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

(4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate
73346-73-3

(4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid; orthoformic acid triethyl ester at 50℃; for 9h; Temperature; Reagent/catalyst; Reflux;95.5%
toluene-4-sulfonic acid In benzene for 1h; Heating;89%
With camphor-10-sulfonic acid
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

benzylamine
100-46-9

benzylamine

(2R,3R)-N1,N4-dibenzyl-2,3-dihydroxysuccinamide
88393-56-0

(2R,3R)-N1,N4-dibenzyl-2,3-dihydroxysuccinamide

Conditions
ConditionsYield
With potassium carbonate In methanol for 7h; Heating;95.3%
With potassium carbonate In methanol Inert atmosphere; Reflux;90%
With potassium carbonate In methanol at 80℃; for 15h; Inert atmosphere;62.4%
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

dibromotriphenylphosphorane
1034-39-5

dibromotriphenylphosphorane

(4R,5R)-2,2,2-Triphenyl-2λ5-[1,3,2]dioxaphospholane-4,5-dicarboxylic acid diethyl ester

(4R,5R)-2,2,2-Triphenyl-2λ5-[1,3,2]dioxaphospholane-4,5-dicarboxylic acid diethyl ester

Conditions
ConditionsYield
With triethylamine In toluene Cyclization;95%
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

ethyl chlorocarbonylacetate
36239-09-5

ethyl chlorocarbonylacetate

1,1'-[(R,R)-1,2-bis(ethoxycarbonyl)ethane-1,2-diyl] 3,3'-diethyl bis(malonate)

1,1'-[(R,R)-1,2-bis(ethoxycarbonyl)ethane-1,2-diyl] 3,3'-diethyl bis(malonate)

Conditions
ConditionsYield
With pyridine In tetrahydrofuran; dichloromethane at 20℃; for 12h;95%
methanol
67-56-1

methanol

diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

butanedioic acid, monoethyl ester
1070-34-4

butanedioic acid, monoethyl ester

Conditions
ConditionsYield
With potassium perrhenate; phosphoric acid; palladium on activated charcoal; hydrogen; pyrographite at 150℃; under 3878.71 Torr;95%
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

(2R,3R)-2,3-O-Bis(diphenylphosphinoxy)weinsaeurediethylester
102139-89-9

(2R,3R)-2,3-O-Bis(diphenylphosphinoxy)weinsaeurediethylester

Conditions
ConditionsYield
With pyridine In diethyl ether at 20℃; for 4h;94%
With dmap In toluene at 20℃; for 3h; Substitution;

L(+)-Diethyl L-tartrate Chemical Properties

MF: C8H14O6
MW: 206.19
EINECS: 201-783-3
(+)-DIETHYL L-TARTRATE(87-91-2),its melting point is 17 °C ,boiling point is  280 °C(lit.);density is 1.204 g/mL at 25 °C(lit.).Appearance is colorless to light yellow liquid.
alpha  :7.5 o (neat)
Following is the molecular structure of (+)-DIETHYL L-TARTRATE(87-91-2):
 

L(+)-Diethyl L-tartrate Uses

(+)-DIETHYL L-TARTRATE(87-91-2) can be used for food additives, pharmaceutical synthesis, chiral compounds split

L(+)-Diethyl L-tartrate Safety Profile

Safty informations about (+)-DIETHYL L-TARTRATE(87-91-2):
Hazard Codes : Xi (Irritant)
Risk Statements :
 R36/37/38 :Irritating to eyes, respiratory system and skin
Safety Statements  :
 S24/25:Avoid contact with skin and eyes
 S36:Wear suitable protective clothing
 S26 :In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany : 3

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