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251380

Sigma-Aldrich

L-(+)-Tartaric acid

ACS reagent, ≥99.5%

Synonym(s):

(2R,3R)-(+)-Tartaric acid, L-Threaric acid

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About This Item

Linear Formula:
HO2CCH(OH)CH(OH)CO2H
CAS Number:
87-69-4
Molecular Weight:
150.09
Beilstein/REAXYS Number:
1725147
EC Number:
201-766-0
MDL number:
MFCD00064207
UNSPSC Code:
12352100
PubChem Substance ID:
24855129
NACRES:
NA.21

grade

ACS reagent

Quality Level

200

agency

suitable for EPA 200.7
suitable for EPA 200.8

vapor density

5.18 (vs air)

assay

≥99.5%

form

crystalline powder
crystals

optical activity

[α]20/D +12.4°, c = 20 in H2O

optical purity

ee: 99% (GLC)

autoignition temp.

797 °F

impurities

≤0.002% S compounds
≤0.005% insolubles

ign. residue

≤0.02%

mp

170-172 °C (lit.)

anion traces

chloride (Cl-): ≤0.001%
oxalate (C2O42-): passes test
phosphate (PO43-): ≤0.001%

cation traces

Fe: ≤5 ppm
heavy metals (as Pb): ≤5 ppm

functional group

carboxylic acid
hydroxyl

SMILES string

O[C@H]([C@@H](O)C(O)=O)C(O)=O

InChI

1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2-/m1/s1

InChI key

FEWJPZIEWOKRBE-JCYAYHJZSA-N

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Application

L-(+)-Tartaric acid may be used in the synthesis of (R,R)-1,2-diammoniumcyclohexane mono-(+)-tartrate, an intermediate to prepare an enantioselective epoxidation catalyst. It may also be used as a starting material in the multi-step synthesis of 1,4-di-O-benzyl-L-threitol. It can be used a chiral resolving agent for the resolution of 2,2′-bispyrrolidine.
Chiral building block for natural products. Also forms a Diels-Alder catalyst with TiCl2(O-i-Pr)2.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H318

Hazard Classifications

Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

302.0 °F - closed cup

flash_point_c

150 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK7140
BCCK2827
BCCK3423
BCCH4566
BCBP1276V

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Dorothy N Nyangena et al.
Foods (Basel, Switzerland), 9(5) (2020-05-08)
Edible insects are increasingly being considered as food and feed ingredients because of their rich nutrient content. Already, edible insect farming has taken-off in Africa, but quality and safety concerns call for simple, actionable hazard control mechanisms. We examined the
(R,R)-2,2'-bispyrrolidine and (S,S)-2,2'-bispyrrolidine: useful ligands for asymmetric synthesis
Denmark SE, et al.
Organic Syntheses, 83, 121-121 (2006)
1,4-Di-O-alkyl threitols from tartaric acid: 1,4-di-O-benzyl-L-threitol
Mash EA, et al.
Organic Syntheses, 68, 92-92 (1990)
(R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamino manganese(iii) chloride, a highly enantioselective epoxidation catalyst
Jay F. Larrow and Eric N. Jacobsen
Organic Syntheses, 75, 1-1 (1998)
Chemistry Letters (Jpn), 1967-1967 (1986)
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