3-Methylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Base Information

• Chemical Name: 3-Methylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid
• CAS No.: 4397-23-3
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.193
• NSC Number: 167999,167991,167492,110658
• DSSTox Substance ID: DTXSID90963155
• Mol file: 4397-23-3.mol

Synonyms:53624-84-3;4397-23-3;3-Methylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid;6-Methylbicyclo[2.2.1]hept-2-ene-5-carboxylic acid;SCHEMBL352543;DTXSID90963155;SSVKYZDOIWXDIO-UHFFFAOYSA-N;NSC110658;NSC167492;NSC167991;NSC167999;NSC-110658;NSC-167492;NSC-167991;NSC-167999;3-Methylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid #;4397-24-4

Chemical Property of 3-Methylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 0.00216mmHg at 25°C
• Boiling Point: 268.7°Cat760mmHg
• Flash Point: 124.1°C
• Density: 1.164g/cm³
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 152.083729621
• Heavy Atom Count: 11
• Complexity: 220

Purity/Quality:

90%,98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CC(C1C(=O)O)C=C2

Technology Process of 3-Methylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid

There total 38 articles about 3-Methylbicyclo[2.2.1]hept-5-ene-2-carboxylic 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: 97.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + crotonyl chloride (10487-71-5) → endo-3-methylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid (4397-23-3,4397-24-4,16651-50-6,31329-97-2,53624-84-3,65942-11-2,127179-45-7,130793-97-4,139891-78-4)

Guidance literature:

In diethyl ether; for 96h; Ambient temperature;

DOI:10.1016/0040-4020(80)80229-8

Reference yield: 90.0%

2-butenoic acid (3724-65-0) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → endo-3-methylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid (4397-23-3,4397-24-4,16651-50-6,31329-97-2,53624-84-3,65942-11-2,127179-45-7,130793-97-4,139891-78-4) + (3-endo,2-exo)-3-methylbicyclo<2.2.1>hept-5-ene-2-carboxylic acid (4397-23-3,4397-24-4,16651-50-6,31329-97-2,53624-84-3,65942-11-2,127179-45-7,130793-97-4,139891-78-4)

Guidance literature:

With tetraacetyl diborate; In neat (no solvent); at 0 ℃; Reagent/catalyst;

Reference yield: 90.0%

2-butenoic acid (3724-65-0) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → endo-3-methylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid (4397-23-3,4397-24-4,16651-50-6,31329-97-2,53624-84-3,65942-11-2,127179-45-7,130793-97-4,139891-78-4) + (3-endo,2-exo)-3-methylbicyclo<2.2.1>hept-5-ene-2-carboxylic acid (4397-23-3,4397-24-4,16651-50-6,31329-97-2,53624-84-3,65942-11-2,127179-45-7,130793-97-4,139891-78-4)

Guidance literature:

With tetraacetyl diborate; In neat (no solvent); at 0 ℃; Reagent/catalyst;

upstream raw materials:

(E)-but-2-enoic acid

endo-Dicyclopentadien

3-methylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde

cyclopenta-1,3-diene

Downstream raw materials:

6-endo-hydroxy-3-exo-methylnorborn-2-endo-ylcarboxylic acid γ-lactone

1-((1R,2R,3S,4S)-3-Methyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-1,3-bis-((S)-1-phenyl-ethyl)-urea

3-exo-methylnorborn-7-anti-ylcarboxylic acid γ-lactone

endo-2-carbomethoxy-exo-3-methylbicyclo[2,2,1]hept-5-ene