2-Methylenecyclopropaneacetic Acid

Base Information

• Chemical Name: 2-Methylenecyclopropaneacetic Acid
• CAS No.: 1073-00-3
• Molecular Formula: C6H8 O2
• Molecular Weight: 112.13
• European Community (EC) Number: 663-620-6
• UNII: 516144FI4M
• DSSTox Substance ID: DTXSID30910284
• Nikkaji Number: J976.519K
• Wikipedia: Methylene_cyclopropyl_acetic_acid
• Wikidata: Q21099575
• ChEMBL ID: CHEMBL314481
• Mol file: 1073-00-3.mol

Synonyms:MCPPA;methylenecyclopropaneacetic acid;methylenecyclopropylacetic acid;methylenecyclopropylacetic acid, sodium salt

Chemical Property of 2-Methylenecyclopropaneacetic Acid

Chemical Property:

• Vapor Pressure: 0.0188mmHg at 25°C
• Boiling Point: 234°C at 760 mmHg
• PKA: 4.54±0.10(Predicted)
• Flash Point: 140.9°C
• PSA: 37.30000
• Density: 1.2g/cm³
• LogP: 1.03720
• Storage Temp.: ?20°C
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 112.052429494
• Heavy Atom Count: 8
• Complexity: 138

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-MethylenecyclopropaneaceticAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-38

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=C1CC1CC(=O)O
• Uses: 2-Methylenecyclopropaneacetic Acid is an intermediate in the preparation of novel agents for the therapy of non-insulin dependent diabetes mellitus.

Technology Process of 2-Methylenecyclopropaneacetic Acid

There total 7 articles about 2-Methylenecyclopropaneacetic 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: 82.0%

2-(methylenecyclopropyl)ethan-1-ol (120477-28-3) → (methylenecyclopropyl)acetic acid (1073-00-3)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In acetone; at -5 ℃; for 6h;

DOI:10.1021/jo00384a017

Reference yield:

2-[2-(1-chloro-1-methylcycloprop-2-yl)ethoxy]tetrahydro-2H-pyran (107616-97-7) → (methylenecyclopropyl)acetic acid (1073-00-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / t-BuOK / dimethylsulfoxide / 7 h / 70 °C

2: 60 percent / p-TsOH*H₂O / methanol / Ambient temperature

3: 70 percent / Jones reagent / acetone / 1 h

With jones reagent; potassium tert-butylate; toluene-4-sulfonic acid; In methanol; dimethyl sulfoxide; acetone;

DOI:10.1021/ja9737634

Reference yield:

2-[2-(methylenecycloprop-2-yl)ethoxy]tetrahydro-2H-pyran (107616-98-8) → (methylenecyclopropyl)acetic acid (1073-00-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / p-TsOH*H₂O / methanol / Ambient temperature

2: 70 percent / Jones reagent / acetone / 1 h

With jones reagent; toluene-4-sulfonic acid; In methanol; acetone;

DOI:10.1021/ja9737634

upstream raw materials:

diazomethane

methylenecyclopropanecarboxylic acid chloride

2-(methylenecyclopropyl)ethan-1-ol

2-[2-(1-chloro-1-methylcycloprop-2-yl)ethoxy]tetrahydro-2H-pyran

Downstream raw materials:

N-<(R)-1'-phenyl-2'-hydroxyethyl>-(1R)-methylenecyclopropaneacetamide

N-(2-hydroxy-1(R)-phenylethyl)-(S)-(2-methylenecyclopropane)acetamide

(1S)-(+)-methylenecyclopropaneacetic acid

spiropentaneacetic acid

Refernces

• 1、 Baldwin, John E.,Parker, David W.. "Stereospecific (Methylenecyclopropyl)acetyl-CoA Inactivation of General Acyl-CoA Dehydrogenase from Pig Kidney". . p. 1475 - 1477. Retrieved 1987.