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

Chemical Properties

Colorless to light yellow liqui

Uses

Different sources of media describe the Uses of 608-68-4 differently. You can refer to the following data:
1. (+)-Dimethyl L-tartrate is used as a starting reagent in the synthesis of (+)-Monomorine I, a pyrrolidine-based alkaloid that is a trail pheromone of the Pharaoh’s ant (Monomorium pharaonis).
2. (+)-Dimethyl L-tartrate can react with sulfur tetrafluoride to form dimethyl meso-2,3-difluorosuccinate.It may be used in the synthesis of the following chiral ligands for use in asymmetric synthesis:(2R, 3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl-2,3-butanediol(-)-(4S,5R)-4-(2-pyridyl)-5-(diphenylphosphino)methyl-2,2-dimethyl-1,3-dioxolane (PYDIPHOS)(4R,5R)-α,α,α′,α′-2,2-hexaphenyl-4,5-dimethanol-1,3-dioxolane

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 
• 67-56-1 methanol 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 11003-23-9 Elaiophylin 
• 21066-72-8 diethyl tartrate 
• 87-69-4 tartaric acid 
• 87-69-4 L-Tartaric acid 
• 149-73-5 trimethyl orthoformate 
• 22335-52-0 dimethyl (4R,5R)-1,3,2-dioxathiolane-4,5-dicarboxylate 2-oxide 
• 181586-74-3 (2R,3R,5R,6R)-5,6-dimethoxy-5,6-dimethyl[1,4]dioxane-2,3-dicarboxylic acid dimethyl ester 
• 681-84-5 tetramethylorthosilicate 
• 87-69-4 L-tartaric acid 
• 624-49-7 dimethylfumarate 

Downstream Products

• 38270-72-3 dimethyl 2,3-O-benzylidene-L-tartrate 
• 28843-34-7 N,N'-diallyl-tartramide 
• 88393-56-0 (2R,3R)-N¹,N⁴-dibenzyl-2,3-dihydroxysuccinamide 
• 38270-70-1 dimethyl meso-2,3-O-benzylidenetartrate 
• 38270-70-1 4,5-trans-bis(methoxycarbonyl)-2-phenyl-1,3-dioxolan 
• 100297-58-3 dimethyl 2-<(p-tolylsulfonyl)oxy>-3-hydroxybutanedioate 
• 114026-66-3 (4R,5R)-2-cyclohexyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester 
• 172794-68-2 (4R,5R)-2-(2-Bromo-benzyl)-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester 
• 115115-93-0 L-(+)-(2,3-dibenzoyl)tartaric acid dimethyl ester 
• 189322-75-6 (4R,5R)-2-(3-Hydroxy-phenyl)-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester 
• 100791-77-3 (4R,5R)-2-ethyl-2-phenyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester 
• 922-68-9 Methyl glyoxylate 
• 306972-70-3 Dimethyl (4R,5R)-2-(4-methoxyphenyl)-2-propyl-1,3-dioxolane-4,5-dicarboxylate 
• 181586-74-3 (2R,3R,5R,6R)-5,6-dimethoxy-5,6-dimethyl[1,4]dioxane-2,3-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.

Practical Cleavage of Acetals by Using an Odorless Thiol Immobilized on Silica

A practical, efficient and general method was developed for the deprotection of a variety of aromatic and aliphatic acetals to their corresponding catechol or diol derivatives using thiol immobilized on silica gel. This is an application for the well-known commercial solid-supported thiol (SiliaMetS Thiol). The procedure is mild and amenable to scale-up. It does not require inert atmosphere and clean conversions were observed. This method is applicable to substituted 1,3-benzodioxole and aliphatic acetals with different functionalities. It offers the advantage of a general route with high yield, which can be undertaken at ambient temperature.

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.