Bicyclo[2.2.1]heptane-2,5-dione

Base Information

• Chemical Name: Bicyclo[2.2.1]heptane-2,5-dione
• CAS No.: 27943-47-1
• Molecular Formula: C7H8 O2
• Molecular Weight: 124.1372
• NSC Number: 119479
• DSSTox Substance ID: DTXSID00950632
• Nikkaji Number: J1.082.299H
• Mol file: 27943-47-1.mol

Synonyms:bicyclo(2.2.1)heptane-2,5-dione

Chemical Property of Bicyclo[2.2.1]heptane-2,5-dione

Chemical Property:

• Vapor Pressure: 0.0175mmHg at 25°C
• Boiling Point: 254.2°Cat760mmHg
• Flash Point: 93.6°C
• Density: 1.264g/cm³
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 124.052429494
• Heavy Atom Count: 9
• Complexity: 163

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CC(=O)C1CC2=O

Technology Process of Bicyclo[2.2.1]heptane-2,5-dione

There total 11 articles about Bicyclo[2.2.1]heptane-2,5-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: 63.0%

Formic acid (1S,2R,4S,5R)-5-formyloxy-bicyclo[2.2.1]hept-2-yl ester → norbornane-2,5-dione (27943-47-1)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In acetone;

DOI:10.1246/cl.1994.189

Reference yield: 44.0%

formic acid 5-formyloxy-bicyclo[2.2.1]hept-2-yl ester (158666-09-2) → norbornane-2,5-dione (27943-47-1)

Guidance literature:

With jones reagent;

DOI:10.1002/anie.200390265

Reference yield:

bicyclo[2.2.1]hepta-2,5-diene (121-46-0) → norbornane-2,5-dione (27943-47-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / Heating

2: 44 percent / Jones reagent

With jones reagent; 2: Jones oxidation;

DOI:10.1002/anie.200390265

upstream raw materials:

cyclopent-2-enone

(N-methylanilino)prop-2-enenitrile

bicyclo[2.2.1]hepta-2,5-diene

2-exo-5-endo-norbornanediol

Downstream raw materials:

C₂₇H₃₆N₄

(1R*,2R*,4R*,5R*)-bicyclo<2.2.1>heptane-2,5-diol

C₂₇H₃₄N₆O₄

3,3,6,6-tetramethylbicyclo<2.2.1>heptane-2.5-dione