cis-Hexahydrophthalic anhydride

Base Information

• Chemical Name: cis-Hexahydrophthalic anhydride
• CAS No.: 13149-00-3
• Molecular Formula: C8H10O3
• Molecular Weight: 154.166
• Hs Code.: 29420000
• European Community (EC) Number: 236-086-3
• UNII: B52Z7TNV87
• DSSTox Substance ID: DTXSID001026621
• Nikkaji Number: J147.581I
• Wikidata: Q27274379
• Mol file: 13149-00-3.mol

Synonyms:13149-00-3;cis-1,2-Cyclohexanedicarboxylic anhydride;cis-Hexahydroisobenzofuran-1,3-dione;cis-Hexahydrophthalic anhydride;cis-Cyclohexane-1,2-dicarboxylic anhydride;Hexahydrophthalic anhydride, cis-;1,3-Isobenzofurandione, hexahydro-, (3aR,7aS)-rel-;(3aS,7aR)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione;UNII-B52Z7TNV87;1,3-Isobenzofurandione, hexahydro-, cis-;B52Z7TNV87;EINECS 236-086-3;AI3-05984;1,2-Cyclohexanedicarboxylic anhydride, cis-;cis-1,2-cyclohexanedicarboxylic acid anhydride;cis-cyclohexane-1,2-dicarboxylic acid anhydride;(3aR,7AS)-hexahydroisobenzofuran-1,3-dione;NSC-8622;trans-1,2-Cyclohexanedicarboxylic anhydride;(3aR,7aS)-hexahydro-2-benzofuran-1,3-dione;SCHEMBL34170;DTXSID001026621;13-Isobenzofurandione hexahydro-cis-;cis-Hexahydro-1,3-isobenzofurandione;MFCD00005926;AKOS016010286;CS-W018042;(cis)-hexahydroisobenzofuran-1,3-dione;cis-1,2-Cyclohexanecarboxylic anhydride;cis-1,2-cyclohexanedicarboxyic anhydride;1,2-cis-cyclohexanedicarboxylic anhydride;AS-75452;cis-1 2-Cyclohexanedicarboxylic anhydride;cis-1,2-cyclohexane-dicarboxyic anhydride;HEXAHYDROPHTHALIC ANHYDRIDE [HSDB];cis-1,2-cyclohexane dicarboxylic anhydride;cis-1,2-cyclohexane-dicarboxylic anhydride;cis-1,2-cyclohexanedicar-boxylic anhydride;cis-1,2-cyclohexanecarboxylic acid anhydride;cis-3-Oxabicyclo[3.4.0]nonane-2,4-dione;racemic cis-hexahydroisobenzofuran-1,3-dione;(3aR,7aS)-octahydro-2-benzofuran-1,3-dione;12-Cyclohexanedicarboxylic anhydride cis-(8CI);cis-cyclohexan-1,2-dicarboxylic acid anhydride;cis-Cyclohexane-1 2-dicarboxylic acid anhydride;E83027;EN300-120136;(3aR,7aS)-rel-Hexahydro-1,3-isobenzofurandione;rel-(3aR 7aS)-Hexahydroisobenzofuran-1 3-dione;1,3-isobenzofurandione, hexahydro-, (3aR,7aS)-;A852543;rel-(3aR,7aS)-hexahydro-2-benzofuran-1,3-dione;1,3-Isobenzofurandiona, hexahidro, (3AR, 7AS)-rel-;Q27274379;1,2-Cyclohexanedicarboxylic anhydride, predominantly cis, 95%;cis-1,2-Cyclohexanecarboxylic anhydride, analytical reference material;cis-cyclohexane-1,2-dicarboxylicacidanhydride, (3aR,7aS)-Hexahydro-isobenzofuran-1,3-dione, 3aa,4,5,6,7,7aa-Hexahydroisobenzofuran-1,3-dione

Chemical Property of cis-Hexahydrophthalic anhydride

Chemical Property:

• Appearance/Colour: white to almost white cryst. low melting solid
• Vapor Pressure: 0.003mmHg at 25°C
• Melting Point: 32-34 °C(lit.)
• Refractive Index: 1.502
• Boiling Point: 283.351 °C at 760 mmHg
• Flash Point: 143.909 °C
• PSA: 43.37000
• Density: 1.236 g/cm³
• LogP: 0.87620
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Moisture Sensitive
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 154.062994177
• Heavy Atom Count: 11
• Complexity: 187

Purity/Quality:

99%min ^*data from raw suppliers

(3aR,7aS)-rel-Hexahydro-1,3-isobenzofurandione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 41-42/43
• Safety Statements: 23-24-26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Plastics & Rubber -> Acid Anhydrides, Cyclic
• Canonical SMILES: C1CCC2C(C1)C(=O)OC2=O
• Isomeric SMILES: C1CC[C@H]2[C@@H](C1)C(=O)OC2=O
• Uses: (3aR,7aS)-rel-Hexahydro-1,3-isobenzofurandione is a reagent used in the synthesis of Pregabalin (P704800), a GABA analogue used as an anticonvulsant. Also used to prepare P2X7 receptor antagonists.

Technology Process of cis-Hexahydrophthalic anhydride

There total 10 articles about cis-Hexahydrophthalic 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: 98.0%

(1R,2R)-(-)-trans-cyclohexane-1,2-dicarboxylic acid (46022-05-3) → trans-1,2-cyclohexanedicarboxylic anhydride (85-42-7,13149-00-3,14166-21-3,31982-85-1,71749-03-6,97233-90-4)

Guidance literature:

With acetyl chloride;

DOI:10.1002/1099-0690(200209)2002:17<2948::AID-EJOC2948>3.0.CO;2-E

Reference yield: 96.0%

cis-1,2,3,6-tetrahydrophthalic anhydride (935-79-5) → 1,2-cis-cyclohexanedicarboxylic anhydride (13149-00-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In 1,4-dioxane; for 24h;

Reference yield: 94.0%

(1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) → 1,2-cis-cyclohexanedicarboxylic anhydride (13149-00-3)

Guidance literature:

With Isopropenyl acetate; Montmorillonite KSF; for 0.0666667h; Irradiation;

DOI:10.1080/00397919308009796

upstream raw materials:

(1R,2S)-cyclohexane-1,2-dicarboxylic acid

trans-1,2-cyclohexanedicarboxylic acid

cis-1,2,3,6-tetrahydrophthalic anhydride

(+/-)-trans-1,2-cyclohexanedicarboxylic anhydride

Downstream raw materials:

2-(3-morpholino-propyl)-(3ar,7ac)-hexahydro-isoindole-1,3-dione

cis-2-(ethoxycarbonyl)cyclohexanecarboxylic acid

(+/-)-2t-(4-methoxy-benzoyl)-cyclohexane-r-carboxylic acid

cis-2-(4'-methoxybenzoyl)cyclohexane-1-carboxylic acid

Refernces

• 1、 -. "Synthesis method of trans 1 and 2 - cyclohexane dicarboxylic acid monomethylester". Paragraph 0033-0039; 0040-0043. . Retrieved 2021/08/25.
• 2、 Rovira, Xavier,Harrak, Youssef,Trapero, Ana,Gonzlez-Bulnes, Patricia,Malhaire, Fanny,Pin, Jean-Philippe,Goudet, Cyril,Giraldo, Jesffls,Llebaria, Amadeu. "Exploring the active conformation of cyclohexane carboxylate positive allosteric modulators of the type 4 metabotropic glutamate receptor". . p. 2685 - 2698. Retrieved 2015/02/02.