TRIMETHYL CITRATE

Base Information

• Chemical Name: TRIMETHYL CITRATE
• CAS No.: 1587-20-8
• Molecular Formula: C9H14O7
• Molecular Weight: 234.206
• Hs Code.: 29181500
• European Community (EC) Number: 216-449-2
• NSC Number: 75824
• UNII: 2P8176332L
• DSSTox Substance ID: DTXSID2061804
• Nikkaji Number: J26.348F
• Wikidata: Q27255361
• Metabolomics Workbench ID: 135445
• ChEMBL ID: CHEMBL455514
• Mol file: 1587-20-8.mol

Synonyms:Citric acid, trimethyl ester(6CI,7CI,8CI);1,2,3-Propanetricarboxylicacid, 2-hydroxy-, trimethyl ester (9CI);3-Hydroxy-3-methoxycarbonylpentanedioic acid dimethyl ester;NSC75824;

Chemical Property of TRIMETHYL CITRATE

Chemical Property:

• Vapor Pressure: 0.00732mmHg at 25°C
• Melting Point: 75-78 °C
• Refractive Index: 1.458
• Boiling Point: 238.8 °C at 760 mmHg
• PKA: 10.43±0.29(Predicted)
• Flash Point: 79.2 °C
• PSA: 99.13000
• Density: 1.265 g/cm³
• LogP: -0.98330
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• Water Solubility.: 53.2g/L at 20℃
• XLogP3: -1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 234.07395278
• Heavy Atom Count: 16
• Complexity: 266

Purity/Quality:

99% ^*data from raw suppliers

Trimethyl Citrate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CC(CC(=O)OC)(C(=O)OC)O
• Description: Trimethyl citrate is an ester of citric acid. It is a kind of non-toxic plasticizer1. Trimethyl citrate is one of the constituents of Dioscorea opposita2. The IC50 value for monoamine oxidase-B of trimethyl citrate was studied. It has various applications3: it can do the main flame retardant candle flame color, its melting point and can fully meet the flammability requirements of candle products. It can be used for the synthesis of pharmaceutical and pesticide. It can act as the main raw material for the production of citric acid hydrochloride, citric acid hydrochloride as well as the synthetic hot melt adhesive. It can also be used as the methyl methacrylate polymer a blowing agent, a stabilizer acrylamide, polyamide adhesive initiators, PVC plasticizers. It can also be used as solvent for household and II cleaner, film-former4.
• Uses: Trimethyl Citrate is a reagent used in the preparation of citrate-ciprofloxacin conjugates which has antibacterial activity.

Technology Process of TRIMETHYL CITRATE

There total 13 articles about TRIMETHYL CITRATE 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: 99.0%

methanol (67-56-1) + citric acid (77-92-9,906507-37-7) → trimethyl citrate (1587-20-8)

Guidance literature:

With zirconium(IV) oxychloride; In toluene; at 120 ℃; for 1h;

DOI:10.1016/j.jde.2005.06.005

Reference yield: 94.0%

methanol (67-56-1) + malonic acid (141-82-2) → trimethyl citrate (1587-20-8)

Guidance literature:

With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; at 70 ℃; for 20h;

DOI:10.3390/molecules24142608

Reference yield: 90.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + citric acid (77-92-9,906507-37-7) → trimethyl citrate (1587-20-8)

Guidance literature:

In methanol; diethyl ether; at 0 ℃;

upstream raw materials:

methanol

citric acid

diazomethane

2-Hydroxy-1,2,3-propanetricarboxylic Acid 2-Methyl Ester

Downstream raw materials:

citric acid tris-benzylamide

citric acid α,α'-diamide

citric acid α-amide

citric acid triamide

Refernces

• 1、 Anet, Frank A.L.,Park, Jaemin. "Proton chemical shift assignments in citrate and trimethyl citrate in chiral media". . p. 411 - 416. Retrieved 1992.
• 2、 -. "Citrate plasticizer". Paragraph 0061-0063. . Retrieved 2021/05/15.
• 3、 ?ebular, Klara,Bo?i?, Bojan ?.,Stavber, Stojan. "1,3-Dibromo-5,5-dimethylhydantoin as a Precatalyst for Activation of Carbonyl Functionality". supporting information. . Retrieved 2019/08/01.