bicyclo[2.2.1]hept-2-ene-2,3-dicarboxylic acid

Base Information

• Chemical Name: bicyclo[2.2.1]hept-2-ene-2,3-dicarboxylic acid
• CAS No.: 16508-04-6
• Molecular Formula: C₉H₁₀O₄
• Molecular Weight: 182.176
• Mol file: 16508-04-6.mol

Synonyms:2-Norbornene-2,3-dicarboxylicacid (6CI,7CI,8CI); NSC 239113

Chemical Property of bicyclo[2.2.1]hept-2-ene-2,3-dicarboxylic acid

Chemical Property:

• Vapor Pressure: 1.25E-06mmHg at 25°C
• Boiling Point: 374.2°Cat760mmHg
• Flash Point: 194.3°C
• Density: 1.53g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of bicyclo[2.2.1]hept-2-ene-2,3-dicarboxylic acid

There total 11 articles about bicyclo[2.2.1]hept-2-ene-2,3-dicarboxylic acid 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: 88.0%

bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid (15872-28-3) → bicyclo<2,2,1>hept-2-ene-2,3-dicarboxylic acid (16508-04-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; ethyl acetate;

DOI:10.1021/jo00185a006

Reference yield: 59.0%

Dimethyl Bicyclo<2.2.1>hept-2-ene-2,3-dicarboxylate (17931-56-5) → bicyclo<2,2,1>hept-2-ene-2,3-dicarboxylic acid (16508-04-6)

Guidance literature:

Dimethyl Bicyclo<2.2.1>hept-2-ene-2,3-dicarboxylate; With water; sodium hydroxide; In methanol; at 60 ℃; for 10h;

With hydrogenchloride; In water; pH=1;

Reference yield:

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → bicyclo<2,2,1>hept-2-ene-2,3-dicarboxylic acid (16508-04-6)

Guidance literature:

Multi-step reaction with 3 steps

1: anschliessendes Erwaermen mit H₂O

2: platinum; ethyl acetate / Hydrogenation

With ethyl acetate; platinum;

upstream raw materials:

(1R,2S,3R,4S)-2,3-dibromobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride

bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid

Dimethyl Bicyclo<2.2.1>hept-2-ene-2,3-dicarboxylate

cyclopenta-1,3-diene

Downstream raw materials:

norbornane-2endo,3endo-dicarboxylic acid

C₂₇H₃₀ClN₅O₂

C₄₃H₅₀N₈O₄

C₃₃H₃₄N₈

Refernces

• 1、 -. "Bridged Ring compounds As Hepatitis C Virus (HCV) Inhibitors And Pharmaceutical Applications Thereof". Paragraph 1020; 1029; 1030; 1031; 1032. . Retrieved 2015/03/28.
• 2、 Bartlett, Paul D.,Roof, Antonius A. M.,Subramanyam, Ravi,Winter, William J.. "Addition Reactions to syn- and anti-Sesquinorbornenes Involving Ionic Mechanisms. The Role of Tetracyanoethylene". . p. 1875 - 1880. Retrieved 2007/10/02.