3,4,5,6-Tetrahydrophthalic anhydride

Base Information

• Chemical Name: 3,4,5,6-Tetrahydrophthalic anhydride
• CAS No.: 2426-02-0
• Molecular Formula: C8H8O3
• Molecular Weight: 152.15
• Hs Code.: H8O3 MOL WT. 152.15
• European Community (EC) Number: 219-374-3
• NSC Number: 61333,11211
• UNII: 01D3M89A2W
• DSSTox Substance ID: DTXSID9075298
• Nikkaji Number: J76.414K
• Wikidata: Q27231422
• Mol file: 2426-02-0.mol

Synonyms:3,4,5,6-tetrahydrophthalic acid anhydride

Chemical Property of 3,4,5,6-Tetrahydrophthalic anhydride

Chemical Property:

• Appearance/Colour: White to cream crystalline powder
• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 69-73 °C(lit.)
• Refractive Index: 1.529
• Boiling Point: 302.3 °C at 760 mmHg
• Flash Point: 146.1 °C
• PSA: 43.37000
• Density: 1.29 g/cm³
• LogP: 0.94040
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly, Sonicated), DMSO (Sparingly)
• Water Solubility.: REACTS
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 152.047344113
• Heavy Atom Count: 11
• Complexity: 237

Purity/Quality:

99% ^*data from raw suppliers

3,4,5,6-Tetrahydrophthalic anhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-52/53-42/43-41
• Safety Statements: 26-36-61-37/39-24-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCC2=C(C1)C(=O)OC2=O
• Uses: 3,4,5,6-Tetrahydrophthalic Anhydride is useful in the synthesis and biological evaluation of 6-hydroxypyridazinone benzisoxazoles as an atypical antipsychotics.

Technology Process of 3,4,5,6-Tetrahydrophthalic anhydride

There total 27 articles about 3,4,5,6-Tetrahydrophthalic anhydride 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: 100.0%

1,4-cyclohexadiene-1,2-dicarboxylic anhydride (4773-89-1) → 3,4,5,6-Tetrahydrophthalic anhydride (2426-02-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; for 0.25h;

DOI:10.1021/tx960074h

Reference yield: 84.0%

3-cyclohexene-1,2-dicarboxylic acid (25079-83-8) → 3,4,5,6-Tetrahydrophthalic anhydride (2426-02-0)

Guidance literature:

With acetic anhydride; for 1.5h; Heating;

DOI:10.1080/00397919308009865

Reference yield:

endothall anhydride (5442-12-6) → phthalic anhydride (85-44-9) + 3,4,5,6-Tetrahydrophthalic anhydride (2426-02-0) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With 1 wtpercent Pd/C loaded on zeolite H-Y with a silica-alumina ratio of 30; In toluene; at 200 ℃; for 4h; under 750.075 Torr; Reagent/catalyst; Inert atmosphere;

DOI:10.1002/cssc.201600776

upstream raw materials:

cis-1,2,5,6-tetrahydrophthalic anhydride

1,2,3,6-Tetrahydrophthalic anhydride

phthalic anhydride

1,4-cyclohexadiene-1,2-dicarboxylic anhydride

Downstream raw materials:

1,2-dimethyl cyclohex-1-ene-1,2-dicarboxylate

3-benzylidene-4,5,6,7-tetrahydro-3H-isobenzofuran-1-one

2-(4-hydroxy-phenyl)-4,5,6,7-tetrahydro-isoindole-1,3-dione

3,4,5,6-Tetrahydrophthal-N-(p-methoxyphenyl)imid

Refernces

• 1、 Fickentscher. "N (3,4,5,6 tetrahydrophthalyl) glutamic acid imide". . p. 520 - 522. Retrieved 1976.
• 2、 Bailey,Amstutz. "-". . p. 3828,3830. Retrieved 1956.
• 3、 Hueckel,Lampert. "-". . p. 1811,1812. Retrieved 1934.
• 4、 Genuino, Homer C.,Thiyagarajan, Shanmugam,van der Waal, Jan C.,de Jong, Ed,van Haveren, Jacco,van Es, Daan S.,Weckhuysen, Bert M.,Bruijnincx, Pieter C. A.. "Selectivity Control in the Tandem Aromatization of Bio-Based Furanics Catalyzed by Solid Acids and Palladium". . p. 277 - 286. Retrieved 2017/01/17.
• 5、 Bae, Yeon Kyu,Cho, Chan Sik. "Palladium-catalyzed carbonylative cyclization of β-Bromo-α, β-unsaturated carboxylic acids leading to maleic anhydrides". . p. 1848 - 1850. Retrieved 2013/09/12.