2-Benzoyl-cyclopropanecarboxylic acid

Base Information

• Chemical Name: 2-Benzoyl-cyclopropanecarboxylic acid
• CAS No.: 1601-81-6
• Molecular Formula: C₁₁H₁₀O₃
• Molecular Weight: 190.199
• NSC Number: 167088
• DSSTox Substance ID: DTXSID50304727
• Mol file: 1601-81-6.mol

Synonyms:2-BENZOYL-CYCLOPROPANECARBOXYLIC ACID;1601-81-6;2-benzoylcyclopropane-1-carboxylic acid;2-benzoylcyclopropanecarboxylic acid;22811-70-7;Cyclopropanecarboxylic acid, 2-benzoyl-;Trans-2-benzoyl-cyclopropanecarboxylic acid;NSC167088;rac-(1r,2s)-2-benzoylcyclopropane-1-carboxylic acid;SCHEMBL8775309;DTXSID50304727;MFCD00749300;STK527217;AKOS005260260;NSC-167088;SB34004;SB34005;SB35612;2-BENZOYL-CYCLOPROPANECARBOXYLICACID;2-(phenylcarbonyl)cyclopropanecarboxylic acid;CS-0323947

Chemical Property of 2-Benzoyl-cyclopropanecarboxylic acid

Chemical Property:

• Vapor Pressure: 4.01E-06mmHg at 25°C
• Boiling Point: 369.8°Cat760mmHg
• Flash Point: 191.7°C
• PSA: 54.37000
• Density: 1.334g/cm³
• LogP: 1.59000
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 190.062994177
• Heavy Atom Count: 14
• Complexity: 253

Purity/Quality:

99%min ^*data from raw suppliers

cis-2-Benzoyl-cyclopropanecarboxylicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-Benzoyl-cyclopropanecarboxylic acid

There total 9 articles about 2-Benzoyl-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: 61.0%

3-oxabicyclo[3.1.0]hexane-2,4-dione (5617-74-3) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → cis 2-benzoylcyclopropanecarboxylic acid (1601-81-6,1601-82-7,22811-70-7)

Guidance literature:

With aluminum (III) chloride; Sealed tube; Inert atmosphere;

DOI:10.1021/jacs.6b01728

Reference yield:

2-benzoyl-cyclopropane-1,1-dicarboxylic acid (6366-29-6) → cis 2-benzoylcyclopropanecarboxylic acid (1601-81-6,1601-82-7,22811-70-7)

Guidance literature:

at 180 ℃;

DOI:10.1021/ja01334a056

Reference yield:

3-chloropropiophenone (936-59-4) → cis 2-benzoylcyclopropanecarboxylic acid (1601-81-6,1601-82-7,22811-70-7)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium acetate; methanol. sodium methylate

2: bromine / Erwaermen des Reaktionsprodukts mit Kaliumacetat in Methanol

3: water containing diethyl ether; sodium methylate / Behandeln des Reaktionsprodukts mit wss. Kalilauge

4: 180 °C

With diethyl ether; bromine; sodium methylate; potassium acetate;

DOI:10.1021/ja01334a056

upstream raw materials:

2-benzoyl-cyclopropane-1,1-dicarboxylic acid

3-oxabicyclo[3.1.0]hexane-2,4-dione

benzene

cis-1,2-cyclopropanedicarboxylic acid anhydride

Refernces

• 1、 Amador, Adrian G.,Sherbrook, Evan M.,Yoon, Tehshik P.. "Enantioselective Photocatalytic [3 + 2] Cycloadditions of Aryl Cyclopropyl Ketones". supporting information. p. 4722 - 4725. Retrieved 2016/05/10.