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

Base Information

• Chemical Name: 3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione
• CAS No.: 3647-74-3
• Molecular Formula: C9H9 N O2
• Molecular Weight: 163.176
• Hs Code.: 2925190090
• NSC Number: 147237,53245,31978,31977
• DSSTox Substance ID: DTXSID00859959
• Nikkaji Number: J993.991A
• ChEMBL ID: CHEMBL1972318
• Mol file: 3647-74-3.mol

Synonyms:K 2154;K-2154;norborn-5-ene-2,3-cis-exo-dicarboximide;norendimide;noreximide;noreximide, (3aalpha,4alpha,7alpha,7aalph )-isomer;noreximide, (3aalpha,4beta,7beta,7aalpha)-isomer;noreximide, potassium salt

Chemical Property of 3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

Chemical Property:

• Vapor Pressure: 1.97E-05mmHg at 25°C
• Melting Point: 186.0 to 190.0 °C
• Boiling Point: 362.1°Cat760mmHg
• Flash Point: 177.1°C
• PSA: 46.17000
• Density: 1.339g/cm³
• LogP: 0.40990
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 163.063328530
• Heavy Atom Count: 12
• Complexity: 280

Purity/Quality:

99% ^*data from raw suppliers

5-Norbornene-2,3-dicarboximide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C=CC1C3C2C(=O)NC3=O

Technology Process of 3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

There total 4 articles about 3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione 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: 86.0%

5-norbornene-2,3-dicarboxylic anhydride (826-62-0,85081-15-8,85081-16-9) → bicyclo<2.2.1>-5-hepten-2,3-dicarbonimide (3647-74-3)

Guidance literature:

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

DOI:10.1007/s11696-019-00969-6

Reference yield:

5-norbornene-2,3-dicarboxylic anhydride (826-62-0,85081-15-8,85081-16-9) + methylamine (74-89-5) → bicyclo<2.2.1>-5-hepten-2,3-dicarbonimide (3647-74-3)

Guidance literature:

In water; at 95 ℃; for 2h;

DOI:10.1021/jo00314a006

Reference yield:

→ Bicyclo<2.2.1>hept-5-en-2,3-endodicarboximid (3647-74-3,6265-30-1,6319-06-8)

Guidance literature:

Norbornen-(5)-dicarbonsaeure-(endo-cis-2,3)-anhydrid, konz. wss. NH3, Kochen, 9 h;

DOI:10.1021/ja01506a037

upstream raw materials:

5-norbornene-2,3-dicarboxylic anhydride

methylamine

Downstream raw materials:

4-aza-4-(3-phenyl(2H,4H-benzo[2,4-3]1,3-oxazaperhydroin-6yl))tri-cycle[5.2.1.0<2,6>]dec-8-ene-3,5-dione

Refernces

• 1、 Markevich, I. N.,Borisova, G. S.,Glebova, N. N.,Sharaev, O. K.,Ostrovskaya, I. Ya.,Gol'berg, A. I.. "RELATIVE REACTIVITIES OF DOUBLE BONDS IN COMPOUNDS WITH FUNCTIONAL GROUPS TOWARDS THE DIMETHYLCYANOMETHYL RADICAL". . p. 789 - 792. Retrieved 2007/10/02.
• 2、 Maruyama, Kazuhiro,Ishitoku, Takeshi,Kubo, Yasuo. "Photochemistry of Aliphatic Imides. Synthesis of Azetidine-2,4-diones via Photochemical Isomerization of Succinimides and N-Formyl-N-methyl α, β -Unsaturated Amides". . p. 27 - 34. Retrieved 2007/10/02.