(-)-2,3-Dimethylbutane-1,2,3-tricarboxylic acid

Base Information

• Chemical Name: (-)-2,3-Dimethylbutane-1,2,3-tricarboxylic acid
• CAS No.: 2385-74-2
• Molecular Formula: C9H14 O6
• Molecular Weight: 218.207
• Hs Code.: 2917190090
• European Community (EC) Number: 219-192-4
• DSSTox Substance ID: DTXSID10875822,DTXSID201019894
• Nikkaji Number: J6.237E,J95.918I
• Mol file: 2385-74-2.mol

Synonyms:2385-74-2;(-)-2,3-Dimethylbutane-1,2,3-tricarboxylic acid;2,3-dimethylbutane-1,2,3-tricarboxylic acid;EINECS 219-192-4;camphoronic acid;508-34-9;Camphoronsaure;l-Camohoronic acid;2,3-dimethyl-1,2,3-butanetricarboxylic acid;SCHEMBL233792;1,2,3-Butanetricarboxylic acid, 2,3-dimethyl-, (-)-;DTXSID10875822;DTXSID201019894;1,2,3-Butanetricarboxylic acid, 2,3-dimethyl-;AE-562/12245652

Chemical Property of (-)-2,3-Dimethylbutane-1,2,3-tricarboxylic acid

Chemical Property:

• Vapor Pressure: 0.000483mmHg at 25°C
• Melting Point: 163-164 °C
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 291.5°C at 760 mmHg
• PKA: 3.26±0.15(Predicted)
• Flash Point: 144.3°C
• PSA: 111.90000
• Density: 1.354g/cm³
• LogP: 0.66280
• Water Solubility.: 111g/L(16 oC)
• XLogP3: 0
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 218.07903816
• Heavy Atom Count: 15
• Complexity: 306

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C(=O)O)C(C)(CC(=O)O)C(=O)O

Technology Process of (-)-2,3-Dimethylbutane-1,2,3-tricarboxylic acid

There total 42 articles about (-)-2,3-Dimethylbutane-1,2,3-tricarboxylic 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:

D-(+)-camphoric acid (124-83-4) + water (7732-18-5) → (+-)-camphoronic acid (508-34-9,2385-74-2,102571-53-9) + oxalic acid (144-62-7,97993-78-7) + glycidic acid (503-11-7)

Guidance literature:

Reference yield:

(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (464-49-3,68546-28-1) → (+-)-camphoronic acid (508-34-9,2385-74-2,102571-53-9) + D-(+)-camphoric acid (124-83-4)

Guidance literature:

u.a.Nebenprodukte;

Reference yield:

ethyl 2,2-dimethyl-3-oxobutanoate (597-04-6) → (+-)-camphoronic acid (508-34-9,2385-74-2,102571-53-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / TiCl₄ / 1,2-dichloro-ethane / 1.) 5 deg C to room temperature, 2.) reflux, 12 h

2: ethanol / 10 h / Heating

3: 1.) aq. HCl, 2.) aq. KOH / 1.) reflux, 30 h, 2.) reflux, 70 h

With hydrogenchloride; potassium hydroxide; ethanol; titanium tetrachloride; In 1,2-dichloro-ethane;

upstream raw materials:

3,4-dicyano-2,2,3-trimethyl-glutaric acid diethyl ester

4,7,7-trimethyl-2-oxa-bicyclo[2.2.1]heptan-3-one

nitric acid

water

Downstream raw materials:

trimethylsuccinic anhydride

methylammonium carbonate

isobutyric Acid

Refernces

• 1、 Rajitha,Shylaja,Rajanna,Yadagiri. "Polyethylene Glycols as Efficient Catalysts for the Oxidation of Bicyclic Monoterpenes by Ceric Ammonium Nitrate in Acetonitrile under Acid-Free Conditions: Kinetic and Mechanistic Approach". . p. 383 - 396. Retrieved 2018/03/30.
• 2、 Lange, Jerzy,Kanabus-Kaminska, Jolanta M.,Kral, Agnieszka. "TITANIUM TETRACHLORIDE PROMOTED KNOEVENAGEL CONDENSATION OF A STERICALLY HINDERED KETO ESTER. A HIGH YIELD SYNTHESIS OF CAMPHORONIC ACID". . p. 473 - 478. Retrieved 2007/10/02.