608-68-4

Basic information

• Product Name: (+)-Dimethyl L-tartrate
• Synonyms: (+)-TARTARIC ACID DIMETHYL ESTER;2,3-dihydroxy-[theta-(theta,theta)]-butanedioicacidimethylester;DimethylL-(+)-tartarate;Lg-tartaricaciddimethylester;(2R,3R)-(+)-DIMETHYL TARTRATE;(2R,3R)-2,3-DIHYDROXY-SUCCINIC ACID DIMETHYL ESTER;(+)-DIMETHYL TARTRATE;DIMETHYL (2R,3R)-DIHYDROXYSUCCINATE
• CAS NO: 608-68-4
• Molecular Formula: C₆H₁₀O₆
• Molecular Weight: 178.14
• EINECS: 210-166-8
• Product Categories: FINE Chemical & INTERMEDIATES;Chiral Compounds;chiral;Chiral Building Blocks;Esters (Chiral);Synthetic Organic Chemistry;CHIRAL CHEMICALS;Hydroxy Acids & Deriv.;Chiral Compound
• Mol File: 608-68-4.mol
• Article Data: 48

Chemical Properties

• Melting Point: 57-60 °C (dec.)(lit.)
• Boiling Point: 163 °C23 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White/Crystals
• Density: 1.238 g/mL at 25 °C(lit.)
• Refractive Index: 21 ° (C=2.5, H2O)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 11.44±0.20(Predicted)
• Water Solubility: Soluble in water.
• BRN: 1726256
• CAS DataBase Reference: (+)-Dimethyl L-tartrate(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Dimethyl L-tartrate(608-68-4)
• EPA Substance Registry System: (+)-Dimethyl L-tartrate(608-68-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37-26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 608-68-4(Hazardous Substances Data)

Usage

Description

(+)-Dimethyl L-tartrate is an organic compound that is colorless to light yellow in appearance. It is a chiral compound, which means it has a non-superimposable mirror image, and is used as a starting reagent in the synthesis of various chemicals.

Uses

Used in Chemical Synthesis:
(+)-Dimethyl L-tartrate is used as a starting reagent for the synthesis of (+)-Monomorine I, a pyrrolidine-based alkaloid that serves as a trail pheromone for the Pharaoh's ant (Monomorium pharaonis). This application is significant for studying and understanding the chemical communication and behavior of this particular ant species.
Used in Asymmetric Synthesis:
(+)-Dimethyl L-tartrate can react with sulfur tetrafluoride to form dimethyl meso-2,3-difluorosuccinate, which may be used in the synthesis of chiral ligands for asymmetric synthesis. These ligands, such as (2R, 3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl-2,3-butanediol and (-)-(4S,5R)-4-(2-pyridyl)-5-(diphenylphosphino)methyl-2,2-dimethyl-1,3-dioxolane (PYDIPHOS), are crucial in the development of enantioselective catalysts and the production of chiral compounds with high purity and selectivity.
Used in Pharmaceutical Industry:
(+)-Dimethyl L-tartrate is also utilized in the pharmaceutical industry for the synthesis of various chiral drugs and drug intermediates. The ability to produce chiral compounds with high purity and selectivity is essential in the development of new drugs and the improvement of existing ones, as the efficacy and safety of a drug can be significantly influenced by its chirality.

InChI:InChI=1/C6H10O6/c1-11-5(9)3(7)4(8)6(10)12-2/h3-4,7-8H,1-2H3/t3-,4-/m1/s1

Upstream product

• 186581-53-3 diazomethane 
• 147-73-9 meso-tartaric acid 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 11003-23-9 Elaiophylin 
• 67-56-1 methanol 
• 87-69-4 tartaric acid 
• 87-69-4 L-tartaric acid 
• 87-69-4 L-Tartaric acid 
• 149-73-5 trimethyl orthoformate 
• 181586-74-3 (2R,3R,5R,6R)-5,6-dimethoxy-5,6-dimethyl[1,4]dioxane-2,3-dicarboxylic acid dimethyl ester 
• 22335-52-0 dimethyl (4R,5R)-1,3,2-dioxathiolane-4,5-dicarboxylate 2-oxide 
• 624-49-7 dimethylfumarate 
• 622-00-4 dibenzyl (2R,3R)-2,3-dihydroxybutanedioate 
• 87-91-2 diethyl (2R,3R)-tartrate 

Downstream Products

• 28843-34-7 N,N'-diallyl-tartramide 
• 68572-77-0 O,O'-sec-butylidene-L_g-tartaric acid dimethyl ester 
• 62138-50-5 (R,R)-2,3-dimethoxy-succinic acid dimethyl ester 
• 104333-70-2 (2R,3R)-2-benzyloxy-3-hydroxy-1,4-butanedioic acid dimethyl ester 
• 104333-84-8 dimethyl 2,3-di-O-benzyl-L-tartrate 
• 109771-12-2 dimethyl (2R,3R)-2-O-(p-nitrobenzyl)tartrate 
• 183057-52-5 (4R,5R)-2-(4-Vinyl-phenyl)-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester 
• 183057-61-6 (4R,5R)-2-Phenyl-2-(4-vinyl-phenyl)-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester 
• 189322-75-6 (4R,5R)-2-(3-Hydroxy-phenyl)-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester 
• 306972-70-3 Dimethyl (4R,5R)-2-(4-methoxyphenyl)-2-propyl-1,3-dioxolane-4,5-dicarboxylate 
• 922-68-9 Methyl glyoxylate 
• 303988-74-1 (2R,6R,7R,9R)-dimethyl 2,9-diphenyl-1,8,13,16-tetraoxadispiro-[5.0.5.4]hexadec-14-ene-14,15-dicarboxylate 
• 100791-76-2 (4R,5R)-2-ethyl-2-(4-methoxyphenyl)-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester 

Relevant articles and documents

Synthesis and characterization of monoaryl esters of l-tartaric acid and their process for fries rearrangement

Chiral protected monoaryl esters (2a-2h) were synthesized from monoester of l-tartaric acid, having two asymmetric centers and C2 axis of symmetry. l-tartaric acid was protected and partially hydrolyzed to give the corresponding monoester. Monoester upon treatment with different substituted phenols gave desired monoaryl esters (2a-2h). Fries rearrangement of monoaryl esters was then tried under various conditions by using different Lewis acids. All the compounds were purified and characterized by using spectroscopic techniques like IR, 1H-NMR, 13C-NMR, HRMS-ESI, and elemental analysis. The structure of compound 2e was obtained by X-ray crystallography.

Selective Monoacylation of Diols and Asymmetric Desymmetrization of Dialkyl meso-Tartrates Using 2-Pyridyl Esters as Acylating Agents and Metal Carboxylates as Catalysts

With 2-pyridyl benzoates as acylating agents and Zn(OAc)2 as a catalyst, 1,2-diols, 1,3-diols, and catechol were selectively monoacylated. Furthermore, the highly enantioselective desymmetrization of meso-tartrates was achieved for the first time, utilizing 2-pyridyl esters and NiBr2/AgOPiv/Ph-BOX in CH3CN or CuCl2/AgOPiv/Ph-BOX in EtOAc catalyst systems (up to 96% ee). The latter catalyst system was also effective for the kinetic resolution of dibenzyl dl-tartrate.

Enantioselective Dihydroxylation of Alkenes Catalyzed by 1,4-Bis(9-O-dihydroquinidinyl)phthalazine-Modified Binaphthyl–Osmium Nanoparticles

A series of unprecedented binaphthyl–osmium nanoparticles (OsNPs) with chiral modifiers were applied in the heterogeneous asymmetric dihydroxylation of alkenes. A remarkable size effect of the OsNPs, depending on the density of the covalent organic shells, on the reactivity and enantioselectivity of the dihydroxylation reaction was revealed. Successful recycling of the OsNPs was also demonstrated and high reaction efficiency and enantioselectivity were maintained.