Methyl 1-(4-fluorophenyl)cyclopropanecarboxylate

Base Information

• Chemical Name: Methyl 1-(4-fluorophenyl)cyclopropanecarboxylate
• CAS No.: 943111-83-9
• Molecular Formula: C11H11FO2
• Molecular Weight: 194.206
• Hs Code.: 2916399090
• DSSTox Substance ID: DTXSID30602571
• Wikidata: Q82499699
• Mol file: 943111-83-9.mol

Synonyms:METHYL 1-(4-FLUOROPHENYL)CYCLOPROPANECARBOXYLATE;943111-83-9;methyl 1-(4-fluorophenyl)cyclopropane-1-carboxylate;SCHEMBL20601546;DTXSID30602571;MFCD18434442;AKOS000348633;CS-15784;DB-230660;CS-0045093;D72712;METHYL1-(4-FLUOROPHENYL)CYCLOPROPANECARBOXYLATE

Chemical Property of Methyl 1-(4-fluorophenyl)cyclopropanecarboxylate

Chemical Property:

• PSA: 26.30000
• LogP: 2.03030
• Storage Temp.: Room temperature.
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 194.07430775
• Heavy Atom Count: 14
• Complexity: 227

Purity/Quality:

≥95% ^*data from raw suppliers

Methyl1-(4-fluorophenyl)cyclopropanecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1(CC1)C2=CC=C(C=C2)F

Technology Process of Methyl 1-(4-fluorophenyl)cyclopropanecarboxylate

There total 5 articles about Methyl 1-(4-fluorophenyl)cyclopropanecarboxylate 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: 100.0%

methanol (67-56-1) + 1-(4-fluorophenyl)cyclopropane-1-carboxylic acid (773100-29-1) → methyl 1-(4-fluorophenyl)cyclopropane-1-carboxylate (943111-83-9)

Guidance literature:

With sulfuric acid; for 8h; Reflux;

DOI:10.1016/j.bmc.2008.08.065

Reference yield: 73.0%

4-fluorobenzeneacetic acid methyl ester (34837-84-8) + diphenyl(vinyl)sulfonium trifluoromethanesulfonate → methyl 1-(4-fluorophenyl)cyclopropane-1-carboxylate (943111-83-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 21 ℃; for 12h;

DOI:10.1016/j.tetlet.2018.02.080

Reference yield:

4-fluorophenylacetonitrile (459-22-3) → methyl 1-(4-fluorophenyl)cyclopropane-1-carboxylate (943111-83-9)

Guidance literature:

Multi-step reaction with 4 steps

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

2: sodium hydroxide; dihydrogen peroxide / water; acetone / 2 h / 20 °C / Cooling with ice

3: water; hydrogenchloride / 1,4-dioxane / 100 °C / Reflux

4: sulfuric acid / 8 h / Reflux

With hydrogenchloride; sulfuric acid; N-benzyl-N,N,N-triethylammonium chloride; water; dihydrogen peroxide; sodium hydroxide; In 1,4-dioxane; water; acetone;

upstream raw materials:

methanol

1-(4-fluorophenyl)cyclopropane-1-carboxylic acid

4-fluorobenzeneacetic acid methyl ester

4-fluorophenylacetonitrile

Downstream raw materials:

1-(4-fluorophenyl)cyclopropanecarbohydrazide

Refernces

• 1、 Zhou, Mingwei,Hu, Yimin,En, Ke,Tan, Xuefei,Shen, Hong C.,Qian, Xuhong. "Efficient cyclopropanation of aryl/heteroaryl acetates and acetonitriles with vinyl diphenyl sulfonium triflate". supporting information. p. 1443 - 1445. Retrieved 2018/03/12.