Tricarballylic acid

Base Information

• Chemical Name: Tricarballylic acid
• CAS No.: 99-14-9
• Deprecated CAS: 850848-65-6,854811-52-2,854811-52-2
• Molecular Formula: C6H8O6
• Molecular Weight: 176.126
• Hs Code.: 29171900
• European Community (EC) Number: 202-733-3
• NSC Number: 2347
• UNII: RA5QH2J020
• DSSTox Substance ID: DTXSID8059186
• Nikkaji Number: J4.963H
• Wikipedia: Propane-1,2,3-tricarboxylic_acid
• Wikidata: Q2823313
• Metabolomics Workbench ID: 44740
• ChEMBL ID: CHEMBL1236394
• Mol file: 99-14-9.mol

Synonyms:propane-1,2,3-tricarboxylate;tricarballylic acid;tricarballylic acid, sodium salt;tricarballylic acid, trisodium salt

Chemical Property of Tricarballylic acid

Chemical Property:

• Appearance/Colour: off-white to light brown fine crystalline powder
• Vapor Pressure: 0.00249mmHg at 25°C
• Melting Point: 156-161 °C(lit.)
• Refractive Index: 1.529
• Boiling Point: 266.4 °C at 760 mmHg
• PKA: pK1 (30°): 3.49; pK2: 4.58; pK3: 5.83
• Flash Point: 129.2 °C
• PSA: 111.90000
• Density: 1.574 g/cm³
• LogP: -0.36340
• Storage Temp.: Store below +30°C.
• Solubility.: H2O: 50 mg/mL, clear
• Water Solubility.: Soluble in water (500 mg/ml at 18°C), methanol, and ether (slightly).
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 176.03208797
• Heavy Atom Count: 12
• Complexity: 192

Purity/Quality:

99% ^*data from raw suppliers

1,2,3-Propanetricarboxylic Acid >98.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C(C(CC(=O)O)C(=O)O)C(=O)O
• Uses: It is used as an alternative to DMDHEU (formaldehyde releasing cross- linking agent).

Technology Process of Tricarballylic acid

There total 99 articles about Tricarballylic 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: 86.0%

vinyl glycolic acid (600-17-9) + carbon monoxide (201230-82-2) → tricarallylic acid (99-14-9)

Guidance literature:

With HeMaRaphos; water; toluene-4-sulfonic acid; palladium dichloride; In tetrahydrofuran; at 125 ℃; for 24h; under 30003 Torr; regioselective reaction; Autoclave; Green chemistry;

DOI:10.1002/anie.202008916

Reference yield: 13.0%

(-)-3-dehydroshikimic acid (2922-42-1) → 3,4-Dihydroxybenzoic acid (99-50-3) + tricarallylic acid (99-14-9) + 3,4,5-trihydroxybenzoic acid (149-91-7) + dihydrogallic acid (184105-29-1) + 2-hydroxyresorcinol (87-66-1)

Guidance literature:

With air; Na_1.5H_1.5PO₄; at 40 ℃; for 50h; Rate constant; Mechanism; other oxidant, var. time;

DOI:10.1021/ja952317i

Reference yield:

citric acid (77-92-9,906507-37-7) → 2-methylbutanedioic acid (498-21-5,636-60-2) + tricarallylic acid (99-14-9) + isobutyric Acid (79-31-2) + butyric acid (107-92-6)

Guidance literature:

With hydrogen; In water; at 225 ℃; for 0.67h; under 3000.3 Torr; Pressure; Reagent/catalyst;

upstream raw materials:

methanol

citraconic acid dimethyl ester

potassium cyanide

2,3-Dichloroprop-1-ene

Downstream raw materials:

1,2,3-propanetricarboxylic acid trimethyl ester

2-methylbutanedioic acid

Refernces

• 1、 Krishnamurthy, Ramanarayanan,Pulletikurti, Sunil,Yadav, Mahipal,Yerabolu, Jayasudhan R.. "Cyanide as a primordial reductant enables a protometabolic reductive glyoxylate pathway". . p. 170 - 178. Retrieved 2022/02/11.
• 2、 Beller, Matthias,Ge, Yao,Huang, Weiheng,Jackstell, Ralf,Liu, Jiawang,Neumann, Helfried,Yang, Ji. "Direct and Selective Synthesis of Adipic and Other Dicarboxylic Acids by Palladium-Catalyzed Carbonylation of Allylic Alcohols". supporting information. p. 20394 - 20398. Retrieved 2020/09/21.