1,2,3,6-Tetrahydrophthalimide

Base Information

• Chemical Name: 1,2,3,6-Tetrahydrophthalimide
• CAS No.: 85-40-5
• Molecular Formula: C8H9 N O2
• Molecular Weight: 151.165
• Hs Code.: 2925190090
• European Community (EC) Number: 201-602-8
• NSC Number: 59011
• DSSTox Substance ID: DTXSID8026513
• Nikkaji Number: J36.757E
• Wikidata: Q21045269
• Metabolomics Workbench ID: 46269
• ChEMBL ID: CHEMBL3187796
• Mol file: 85-40-5.mol

Synonyms:cis-4-cycloxexene-1,2-dicarboximide;tetrahydrophthalimide

Chemical Property of 1,2,3,6-Tetrahydrophthalimide

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.00011mmHg at 25°C
• Melting Point: 132-140 ºC
• Refractive Index: 1.5810 (estimate)
• Boiling Point: 337 ºC
• PKA: 11.69±0.20(Predicted)
• Flash Point: 165 ºC
• PSA: 46.17000
• Density: 1.228
• LogP: 0.55400
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 12.2g/L at 20℃
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 151.063328530
• Heavy Atom Count: 11
• Complexity: 221

Purity/Quality:

98% ^*data from raw suppliers

1,2,3,6-Tetrahydrophthalimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Fungicides
• Canonical SMILES: C1C=CCC2C1C(=O)NC2=O
• Uses: 1,2,3,6-Tetrahydrophthalimide, is shown to be urinary metabolites of the fungicide Captan (C175725) in rat and humans.

Technology Process of 1,2,3,6-Tetrahydrophthalimide

There total 7 articles about 1,2,3,6-Tetrahydrophthalimide 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: 95.0%

4-cyclohexene 1-carboxylic acid 2-carboxamide (2028-12-8) → 1,2,3,6-tertahydrophthalimide (85-40-5)

Guidance literature:

In 1,3,5-trimethyl-benzene; at 170 ℃; for 2.5h; Temperature; Solvent; Large scale;

Reference yield: 81.0%

1,2,3,6-Tetrahydrophthalic anhydride (85-43-8) → 1,2,3,6-tertahydrophthalimide (85-40-5)

Guidance literature:

With choline chloride; urea; at 140 ℃; for 1h; Green chemistry;

DOI:10.1007/s11696-019-00969-6

Reference yield: 74.0%

→ 1,2,3,6-tertahydrophthalimide (85-40-5)

Guidance literature:

With ammonia; at 180 ℃;

DOI:10.1016/0040-4020(82)85067-9

upstream raw materials:

1,2,3,6-Tetrahydrophthalic anhydride

N-Hydroxymethyl-cis-4-cyclohexene-1,2-dicarboximide

4-cyclohexene 1-carboxylic acid 2-carboxamide

Downstream raw materials:

2-(4r-methyl-5t-phenyl-oxazolidin-3-ylmethyl)-3a,4,7,7a-tetrahydro-isoindole-1,3-dione

2-(4r-methyl-5c-phenyl-oxazolidin-3-ylmethyl)-3a,4,7,7a-tetrahydro-isoindole-1,3-dione

2-butyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione

(3aR,7aS)-tert-butyl 3a,4,7,7a-tetrahydro-1H-isoindole-2(3H)-carboxylate

Refernces

• 1、 -. "Preparation method of 1,2,3,6-tetrahydrophthalimide". Paragraph 0061; 0063; 0064; 0066; 0067; 0069; 0070; 0072. . Retrieved 2020/01/12.
• 2、 Salakhov,Agadzhanov,Umaeva. "Diels-Alder reactions of hexachlorocyclopentadiene with N-hydroxy- and N-hydroxyalkyl-cis-4-cyclohexene-1,2-dicarboximides". . p. 1313 - 1317. Retrieved 2007/10/03.