(+)-Diacetyl-D-tartaric Acid

Base Information

• Chemical Name: (+)-Diacetyl-D-tartaric Acid
• CAS No.: 66749-60-8
• Molecular Formula: C₈H₁₀O₈
• Molecular Weight: 234.163
• Hs Code.: 2918990090
• European Community (EC) Number: 679-975-5
• Nikkaji Number: J2.637.900H
• Mol file: 66749-60-8.mol

Synonyms:(+)-Diacetyl-D-tartaric Acid;66749-60-8;(2S,3S)-2,3-diacetyloxybutanedioic acid;(2S,3S)-2,3-Diacetoxysuccinic acid;SCHEMBL7092944;MFCD02093460;(2S,3S)-2,3-Diacetoxysuccinicacid;CS-0454709;D2636;D90095;J-500054

Chemical Property of (+)-Diacetyl-D-tartaric Acid

Chemical Property:

• Vapor Pressure: 1.77E-07mmHg at 25°C
• Melting Point: 118°C
• Refractive Index: 22.5 ° (C=5, Acetone)
• Boiling Point: 398.9°C at 760 mmHg
• PKA: 2.12±0.25(Predicted)
• Flash Point: 159.4°C
• PSA: 127.20000
• Density: 1.486g/cm³
• LogP: -0.98100
• Solubility.: almost transparency in Acetone
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 234.03756727
• Heavy Atom Count: 16
• Complexity: 288

Purity/Quality:

98%,99%, ^*data from raw suppliers

(+)-Diacetyl-D-tartaric Acid ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC(C(C(=O)O)OC(=O)C)C(=O)O
• Isomeric SMILES: CC(=O)O[C@@H]([C@@H](C(=O)O)OC(=O)C)C(=O)O

Technology Process of (+)-Diacetyl-D-tartaric Acid

There total 2 articles about (+)-Diacetyl-D-tartaric Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

D-tartaric acid (147-71-7,138508-61-9) + acetyl chloride (75-36-5) → 2,3-diacetoxy-(2S,3S)-butanedioic acid (66749-60-8)

Guidance literature:

for 48h; Heating;

DOI:10.1016/S0014-827X(02)00016-2

Reference yield:

D-tartaric acid (147-71-7,138508-61-9) + acetic anhydride (108-24-7) → 2,3-diacetoxy-(2S,3S)-butanedioic acid (66749-60-8)

Guidance literature:

With sulfuric acid;

Reference yield:

2,3-diacetoxy-(2S,3S)-butanedioic acid (66749-60-8) → Acetic acid (1S,2S)-2-acetoxy-1,2-bis-benzylcarbamoyl-ethyl ester (432555-93-6)

Guidance literature:

Multi-step reaction with 2 steps

1: (COCl)2 / dimethylformamide; CH₂Cl₂ / 2 h / 20 °C

2: 1.69 g / Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

With oxalyl dichloride; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0014-827X(02)00016-2

upstream raw materials:

D-tartaric acid

acetic anhydride

acetyl chloride

Downstream raw materials:

Acetic acid (1S,2S)-2-acetoxy-1,2-bis-benzylcarbamoyl-ethyl ester

1N,4N-di[1-phenyl-(1R)-ethyl]-2,3-diacetoxy-(2S,3S)-butanediamide

1N,4N-di[1-phenyl-(1S)-ethyl]-2,3-diacetoxy-(2S,3S)-butanediamide

1N,4N-di[1-carboethoxy-2-phenyl-(1S)-ethyl]-2,3-diacetoxy-(2S,3S)-butanediamide

Refernces

• 1、 Muto,Kuroda,Kawato,Karasawa,Kubo,Nakamizo. "Synthesis and pharmacological activity of stereoisomers of 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 1-(phenylmethyl)-3-piperidinyl ester". . p. 1662 - 1665. Retrieved 2007/10/02.