1,4-Cyclohexadiene-1,2-dicarboxylic anhydride

Base Information

• Chemical Name: 1,4-Cyclohexadiene-1,2-dicarboxylic anhydride
• CAS No.: 4773-89-1
• Molecular Formula: C8H6O3
• Molecular Weight: 150.134
• NSC Number: 122938
• DSSTox Substance ID: DTXSID00197262
• Nikkaji Number: J640.893A
• Wikidata: Q83070183
• Mol file: 4773-89-1.mol

Synonyms:4773-89-1;1,4-Cyclohexadiene-1,2-dicarboxylic anhydride;4,7-Dihydro-2-benzofuran-1,3-dione;1,3-Isobenzofurandione, 4,7-dihydro-;1,4-CYCLOHEXADIENE-1,2-DICARBOXYLICANHYDRIDE;3,6-Dihydrophthalic anhydride;NSC122938;SCHEMBL1045077;DTXSID00197262;isobenzofuran-1,3(4H,7H)-dione;AKOS006274922;NSC 122938;NSC-122938;4,7-Dihydro-2-benzofuran-1,3-dione #;FT-0606818;Cyclohexa-1,4-diene-1,2-dicarboxylic acid, anhydride

Chemical Property of 1,4-Cyclohexadiene-1,2-dicarboxylic anhydride

Chemical Property:

• Vapor Pressure: 0.000414mmHg at 25°C
• Refractive Index: 1.571
• Boiling Point: 316.3 °C at 760 mmHg
• Flash Point: 156.3 °C
• Density: 1.35 g/cm³
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 150.031694049
• Heavy Atom Count: 11
• Complexity: 269

Purity/Quality:

99.0%Min ^*data from raw suppliers

1,4-CYCLOHEXADIENE-1,2-DICARBOXYLIC ANHYDRIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=CCC2=C1C(=O)OC2=O

Technology Process of 1,4-Cyclohexadiene-1,2-dicarboxylic anhydride

There total 11 articles about 1,4-Cyclohexadiene-1,2-dicarboxylic 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: 99.0%

1,4-Cyclohexadien-1,2-dicarbonsaeure-di-tert-butylester (70332-97-7) → 1,4-cyclohexadiene-1,2-dicarboxylic anhydride (4773-89-1)

Guidance literature:

With toluene-4-sulfonic acid; at 100 ℃; for 0.75h;

Reference yield: 86.0%

buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) + Acetylenedicarboxylic acid (142-45-0) → 1,4-cyclohexadiene-1,2-dicarboxylic anhydride (4773-89-1)

Guidance literature:

In tetrahydrofuran; at 90 ℃; for 12h;

DOI:10.1016/j.jphotochem.2021.113336

Reference yield:

dimethyl cyclohexa-1,4-diene-1,2-dicarboxylate (14309-54-7) → 1,4-cyclohexadiene-1,2-dicarboxylic anhydride (4773-89-1)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 0 - 20 ℃; for 56h;

upstream raw materials:

cyclohexa-2,4-diene-1,2-dicarboxylic acid-anhydride

sodium acetate

acetic anhydride

2,4-cyclohexadiene-1,2-dicarboxylic acid

Downstream raw materials:

Bicyclo<4.4.0>deca-3,8-dien-1,6-dicarbonsaeureanhydrid

3,4,5,6-Tetrahydrophthalic anhydride

7-Phenylbicyclo<4.2.0>octa-3,7-dien-1,6-dicarbonsaeureanhydrid

5-Phenyltetracyclo<3.3.0.0^2,8.0^4,6>octan-2,8-dicarbonsaeureanhydrid

Refernces

• 1、 -. "PYRIDAZINONE-BASED BROAD SPECTRUM ANTI-INFLUENZA INHIBITORS". Page/Page column 91. . Retrieved 2018/02/28.
• 2、 Weber, Gisela,Menke, Klaus,Hopf, Henning. "Alkynes and Cumulenes, XII. The Application of Di-tert-butyl Acetylenedicarboxylate in Diels-Alder Additions". . p. 531 - 541. Retrieved 2007/10/02.