6283-74-5

Basic information

• Product Name: (+)-DIACETYL-L-TARTARIC ANHYDRIDE
• Synonyms: (R,R)-DIACETYLTARTARIC ACID ANHYDRIDE;L-(+)-O,O'-DIACETYL-TARTARIC ACID ANHYDRIDE;(+)-DIACETYL-L-TARTARIC ANHYDRIDE;DIACETYL-L-TARTARIC ANHYDRIDE;DATA;(+)-DI-O-ACETYL-L-TARTARIC ACID ANHYDRIDE;(+)-DI-O-ACETYL-L-TARTARIC ANHYDRIDE;DI-O-ACETYL-L-TARTARIC ANHYDRIDE
• CAS NO: 6283-74-5
• Molecular Formula: C₈H₈O₇
• Molecular Weight: 216.14
• EINECS: 228-502-7
• Product Categories: Chiral Reagents;for Resolution of Bases;Optical Resolution;Synthetic Organic Chemistry
• Mol File: 6283-74-5.mol
• Article Data: 28

Chemical Properties

• Melting Point: 130-135 °C(lit.)
• Boiling Point: 316.55°C (rough estimate)
• Flash Point: 158.2 °C
• Appearance: White/Crystals or Needles
• Density: 1.5197 (rough estimate)
• Vapor Pressure: 4.34E-05mmHg at 25°C
• Refractive Index: 90 ° (C=0.5, CHCl3)
• Storage Temp.: −20°C
• Solubility: Acetone, Chloroform (Slightly, Heated)
• Water Solubility: Soluble in methanol and dichloromethane. Slightly soluble in water.
• Sensitive: Moisture Sensitive
• BRN: 87315
• CAS DataBase Reference: (+)-DIACETYL-L-TARTARIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-DIACETYL-L-TARTARIC ANHYDRIDE(6283-74-5)
• EPA Substance Registry System: (+)-DIACETYL-L-TARTARIC ANHYDRIDE(6283-74-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 6283-74-5(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

Uses

Different sources of media describe the Uses of 6283-74-5 differently. You can refer to the following data:
1. Di-O-acetyl-L-tartaric Anhydride (cas# 6283-74-5) is a compound useful in organic synthesis.
2. (+)-O,O′-Diacetyl-L-tartaric anhydride may be used as a chiral derivatizating agent in the following:determination of enantiomeric vigabatrin in mouse serum samples using ultra-high performance liquid chromatography-quadrupole-time-of-flight mass spectrometry (UHPLC-Q-TOF-M)????????determination of trantinterol in rat plasma by ultra performance liquid chromatography–electrospray ionization mass spectrometry (UPLC–MS/MS)

General Description

(+)-O,O′-Diacetyl-L-tartaric anhydride is an HPLC derivatization reagent for UV/Vis detection. It is mainly employed as a reagent for the chiral derivatization of amino alcohols. It also reacts with alkanoamines in aprotic medium containing trichloroacetic acid and produces tartaric acid monoesters.

Purification Methods

If the IR is good, i.e. no OH bands, then keep it in a vacuum desiccator overnight (over P2O5/paraffin) before use. If OH bands are present then reflux 4g in Ac2O (12.6mL) containing a few drops of conc H2SO4 for 10minutes (use a relatively large flask), pour onto ice, collect the crystals, wash with dry *C6H6 (2 x 2mL), stir with 17mL of cold Et2O, filter and dry in it a vacuum desiccator as above, or store it in dark evacuated ampoules under N2 in small aliquots. It is not very stable in air, the melting point of the crystals drop one degree in the first four days then remains constant (132-134o). If placed in a stoppered bottle, it becomes gummy and the m falls 100o in three days. Recrystllisation leads to decomposition. If good quality anhydride is required it, should be prepared freshly from tartaric acid. It sublimes in a CO2 atmosphere. [Shriner & Furrow Org Synth Coll Vol IV 242 1963, Bell Aust J Chem 34 671 1981, Beilstein 18 III/IV 2296.]

InChI:InChI=1/C8H8O7/c1-3(9)13-5-6(14-4(2)10)8(12)15-7(5)11/h5-6H,1-2H3/t5-,6-/m1/s1

Upstream product

• 147-71-7 D-tartaric acid 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 87-69-4 tartaric acid 
• 87-69-4 L-Tartaric acid 

Downstream Products

• 106942-29-4 L_g-tartaric acid di-p-toluidide 
• 6249-84-9 N-(4-sulfamoyl-phenyl)-L_g-tartramic acid 
• 3019-58-7 N-phenyl-L_g-tartramic acid 
• 78814-80-9 O-benzyl diacetoxysuccinohydroxamate 
• 115061-72-8 phenylammonium salt of (2R,3R)-3-acetoxy-2-hydroxy-3-(phenylcarbamoyl)propanoic acid 
• 115061-70-6 benzylammonium salt of (2R,3R)-3-acetoxy-3-benzylcarbamoyl-2-hydroxypropanoic acid 
• 115061-64-8 benzylammonium salt of (2R,3R)-2,3-diacetoxy-3-(benzylcarbamoyl)propanoic acid 
• 123524-99-2 benzyl diacetoxysuccinic acid 
• 115061-63-7 (2R,3R)-2,3-diacetoxy-4-(benzylamino)-4-oxobutanoic acid 
• 164027-62-7 (R,R)-N-(3-nitrophenyl)-O,O-diacetyltartaric acid monoamide 
• 209625-83-2 (3R,4R)-1-cyclohexyl-3,4-diacetoxypyrrolidine-2,5-dione 
• 209625-79-6 (3R,4R)-3,4-diacetoxy-1-phenylpyrrolidine-2,5-dione 
• 515821-68-8 (2R,3R)-2,3-diacetoxy-N-benzhydryl-N-(2-oxo-2-phenylethyl)succinamic acid 
• 136137-85-4 (3R,4R)-1-benzyl-2,5-dioxopyrrolidine-3,4-diyl diacetate 

Relevant articles and documents

First Room Temperature Chiral Anionic Liquid Forming Micelles and Reverse Micelles

We report the first chiral surface active anionic liquid, T12M, derived from biodegradable tartaric acid, and its unusual properties. T12M features unprecedented combination of characteristics not found in other ionic liquids (ILs): (a) T12M is the first surface active ionic liquid that is fully chiral, by virtue of the presence of chirality in both anionic headgroup and the counterion; (b) T12M remains as room temperature IL for 3 days and then transforms to a semisolid with melting point at ～55 °C. The d-spacings in solid T12M, and T12M lyophilized from its aqueous solution, are 13.89 and 14.54 ?, respectively. (c) Tartaric acid is unconventional and unprecedented starting material for the synthesis of ILs. (d) T12M dissolves in both hydrogen bonding (water) and non-hydrogen bonding (chloroform) solvents and forms anionic chiral micellar aggregates (CMAs) and reverse-CMAs, at very low concentrations 0.32 mM and ～10 mM, respectively. (e) CMAs of T12M adopt structures ranging from spherical to lamellar in shape in water in the 10-200 mM range; however, the zeta potential remained constant at ～ -13 mV. The alkyl chains, are interdigited in the CMAs of T12M in water to form lamellar structures and are extended outward to form reverse micelles in CHCl3.

Determination of the absolute configuration of picrasidine Y, a naturally occurring β-carboline alkaloid

Abstract The absolute configuration of picrasidine Y, a β-carboline alkaloid isolated from Picrasma quassioides (Simaroubaceae), has not been determined. To determine the absolute configuration of picrasidine Y, we synthesized stereoisomers of picrasidine Y through 7-step chemical reactions using tartaric acid as a starting material. Moreover, we extended the scope of application of this synthetic method to canthin-5,6-dione compounds. The absolute configuration of natural picrasidine Y was elucidated based on comparisons of chemically synthesized isoforms with the naturally occurring compound in 1H and 13C NMR spectra, specific optical rotation, HPLC analysis with chiral columns, computational molecular simulation, and analysis with the CD exciton chirality method.

Diastereoselective ritter-like reaction on cyclic trifluoromethylated N,O-acetals derived from L-tartaric acid

Despite the presence of the highly electron-withdrawing fluorinated substituent, cyclic α-trifluoromethylated N-acyliminium ions were successfully generated from fluorinated O-acetyl-N,O-acetal L-tartaric acid derivatives. The addition of nitriles on these intermediates occurred with high to excellent syn diastereoselectivity and led, in most cases, to oxazolines and amides as single diastereomers. The diastereoselectivity of the addition and the nature of the reaction product depend on the substituents on the hydroxyl groups of the tartaric acid scaffold. This methodology gave access to enantiopure, highly functionalized 5-(trifluoromethyl)pyrrolidin-2-one derivatives, bearing the fluorinated substituent on a tetrasubstituted carbon.

RESVERATROL GLYCOLATE AND TARTRATE DERIVATIVES AND SYNTHETIC METHODS THEREFOR

The invention is in the field of resveratrol derivative compounds and compositions, and methods for synthesizing same.