trans-1,2,3,6-Tetrahydrophthalic anhydride

Base Information

• Chemical Name: trans-1,2,3,6-Tetrahydrophthalic anhydride
• CAS No.: 13149-03-6
• Molecular Formula: C₈H₈O₃
• Molecular Weight: 152.15
• Nikkaji Number: J410.985F
• Mol file: 13149-03-6.mol

Synonyms:4-Cyclohexene-1,2-dicarboxylic anhydride, trans-;1,3-Isobenzofurandione, 3a,4,7,7a-tetrahydro-, trans-;trans-1,2,3,6-Tetrahydrophthalic anhydride;(3aR,7aS)-3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione;KMOUUZVZFBCRAM-WDSKDSINSA-N;trans-3a,4,7,7a-Tetrahydroisobenzofuran-1,3-dione;3aalpha,4,7,7abeta-Tetrahydroisobenzofuran-1,3-dione;3a,4,7,7a-Tetrahydro-2-benzofuran-1,3-dione, trans-

Chemical Property of trans-1,2,3,6-Tetrahydrophthalic anhydride

Chemical Property:

• Boiling Point: 305.6°Cat760mmHg
• Flash Point: 148.2°C
• PSA: 43.37000
• Density: 1.289g/cm³
• LogP: 0.65220
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 152.047344113
• Heavy Atom Count: 11
• Complexity: 218

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=CCC2C1C(=O)OC2=O
• Isomeric SMILES: C1C=CC[C@H]2[C@H]1C(=O)OC2=O

Technology Process of trans-1,2,3,6-Tetrahydrophthalic anhydride

There total 5 articles about trans-1,2,3,6-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: 79.0%

trans-cyclohex-4-ene-1,2-dicarboxylic acid (88-98-2,2305-26-2,15573-40-7,50987-15-0,51096-07-2,51096-08-3) → trans-4-Cylohexene-1,2-dicarboxylic anhydride (85-43-8,935-79-5,13149-03-6,51268-23-6)

Guidance literature:

With acetic anhydride; at 60 - 70 ℃;

DOI:10.1016/S0040-4020(01)96537-8

Reference yield:

dimethyl cis-1,2,3,6-tetrahydrophthalate (4841-84-3) → trans-4-Cylohexene-1,2-dicarboxylic anhydride (85-43-8,935-79-5,13149-03-6,51268-23-6)

Guidance literature:

Multi-step reaction with 3 steps

1: Na / ethanol / 0.5 h / Heating

2: 2percent H₂SO₄

3: 79 percent / acetic anhydride / 60 - 70 °C

With sulfuric acid; sodium; acetic anhydride; In ethanol;

DOI:10.1016/S0040-4020(01)96537-8

Reference yield:

dimethyl trans-cyclohex-4-ene-1,2-dicarboxylate (17673-68-6) → trans-4-Cylohexene-1,2-dicarboxylic anhydride (85-43-8,935-79-5,13149-03-6,51268-23-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 2percent H₂SO₄

2: 79 percent / acetic anhydride / 60 - 70 °C

With sulfuric acid; acetic anhydride;

DOI:10.1016/S0040-4020(01)96537-8

upstream raw materials:

trans-cyclohex-4-ene-1,2-dicarboxylic acid

dimethyl cis-1,2,3,6-tetrahydrophthalate

dimethyl trans-cyclohex-4-ene-1,2-dicarboxylate

Downstream raw materials:

dimethyl trans-cyclohex-4-ene-1,2-dicarboxylate

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

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

(1R,2R)-Cyclohex-4-ene-1,2-dicarboxylic acid 1-((R)-2-methoxy-1-phenyl-ethyl) ester 2-methyl ester

Refernces

• 1、 Bernath, Gabor,Stajer, Geza,Szabo, Angela E.,Fueloep, Ferenc,Sohar, Pal. "STEREOCHEMICAL STUDIES 83. SATURATED HETEROCYCLES 76. PREPARATION AND CONFORMATIONAL STUDY OF PARTIALLY SATURATED 3,1-BENZOXAZINES, 3,1-BENZOXAZIN-2-ONES AND 3,1-BENZOXAZINE-2-THIONES". . p. 1353 - 1366. Retrieved 2007/10/02.