1-(3-Methylphenyl)cyclopropanecarboxylic acid

Base Information

• Chemical Name: 1-(3-Methylphenyl)cyclopropanecarboxylic acid
• CAS No.: 886366-16-1
• Molecular Formula: C₁₁H₁₂O₂
• Molecular Weight: 176.215
• European Community (EC) Number: 894-304-8
• DSSTox Substance ID: DTXSID101254629
• Mol file: 886366-16-1.mol

Synonyms:886366-16-1;1-(3-Methylphenyl)cyclopropanecarboxylic acid;1-(3-methylphenyl)cyclopropane-1-carboxylic acid;1-(m-Tolyl)cyclopropanecarboxylic acid;1-m-Tolyl-cyclopropanecarboxylic acid;1-M-TOLYLCYCLOPROPANECARBOXYLIC ACID;SCHEMBL1561226;DTXSID101254629;1-(m-Tolyl)cyclopropanecarboxylicacid;AKOS000125553;AB39484;MCULE-4948550170;DA-29132;CS-0088464;EN300-53537;F79167;Z363997682

Chemical Property of 1-(3-Methylphenyl)cyclopropanecarboxylic acid

Chemical Property:

• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 176.083729621
• Heavy Atom Count: 13
• Complexity: 218

Purity/Quality:

97% ^*data from raw suppliers

1-(3-Methylphenyl)cyclopropanecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC=C1)C2(CC2)C(=O)O
• Uses: 1-(3-Methylphenyl)cyclopropanecarboxylic Acid is derived from (3-Methylphenyl)acetonitrile (M288715), which was used as a reactant to synthesize potential non-nucleoside reverse transcriptase inhibitors (NNRTIs) against HIV. It was also used as a reactant to prepare hepatitis C virus inhibitors.

Technology Process of 1-(3-Methylphenyl)cyclopropanecarboxylic acid

There total 2 articles about 1-(3-Methylphenyl)cyclopropanecarboxylic 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:

1-(m-tolyl)cyclopropanecarbonitrile (124276-71-7) → 1-(3-methylphenyl)-1-cyclopropanecarboxylic acid (886366-16-1)

Guidance literature:

With lithium hydroxide; In water; at 100 ℃;

DOI:10.1002/anie.201603153

Reference yield:

3-methylbenzyl cyanide (2947-60-6) → 1-(3-methylphenyl)-1-cyclopropanecarboxylic acid (886366-16-1)

Guidance literature:

Multi-step reaction with 2 steps

1: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / water / 50 °C

2: lithium hydroxide / water / 100 °C

With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide; lithium hydroxide; In water;

DOI:10.1002/anie.201603153

Reference yield: 85.0%

N-hydroxyphthalimide (524-38-9) + 1-(3-methylphenyl)-1-cyclopropanecarboxylic acid (886366-16-1) → 1,3-dioxoisoindolin-2-yl 1-(m-tolyl)cyclopropane-1-carboxylate

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃;

DOI:10.1039/d1cc02930d

upstream raw materials:

3-methylbenzyl cyanide

1-(m-tolyl)cyclopropanecarbonitrile