Methyl 2-(difluoromethyl)benzoate

Base Information

• Chemical Name: Methyl 2-(difluoromethyl)benzoate
• CAS No.: 1018678-48-2
• Molecular Formula: C9H8F2O2
• Molecular Weight: 186.158
• Hs Code.: 2916399090
• DSSTox Substance ID: DTXSID50700740
• Wikidata: Q72463399
• Mol file: 1018678-48-2.mol

Synonyms:methyl 2-(difluoromethyl)benzoate;1018678-48-2;2-DIFLUOROMETHYL-BENZOIC ACID METHYL ESTER;BENZOIC ACID,1-(DIFLUOROMETHYL)-METHYL ESTER;MFCD16140192;SCHEMBL465679;DTXSID50700740;BBL101413;CK2184;STL555209;AKOS005258377;Methyl 2-(difluoromethyl)benzoate, 95%;AS-45875;SY266020;CS-0210666;FT-0684568;2-DIFLUOROMETHYL-BENZOICACIDMETHYLESTER;A897025;AU-004/43508006;methyl 2-difluoromethylbenzoate

Chemical Property of Methyl 2-(difluoromethyl)benzoate

Chemical Property:

• Melting Point: 31-35°C
• Boiling Point: 239℃
• Flash Point: 96℃
• PSA: 26.30000
• Density: 1.198
• LogP: 2.41080
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 186.04923582
• Heavy Atom Count: 13
• Complexity: 183

Purity/Quality:

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

1-(Difluoromethyl)-methylEsterBenzoicAcid ^*data from reagent suppliers

Safty Information:

• Statements: 52

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC=CC=C1C(F)F

Technology Process of Methyl 2-(difluoromethyl)benzoate

There total 3 articles about Methyl 2-(difluoromethyl)benzoate 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: 87.0%

2-Methyl-benzoic acid methyl ester (89-71-4) → methyl 5-phenyl-2-difluoromethylbenzoate (1018678-48-2)

Guidance literature:

With sodium persulfate; silver nitrate; 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(hexafluorophosphate); In water; acetonitrile; at 80 ℃; for 3h; Inert atmosphere; Schlenk technique; Cooling with liquid nitrogen;

DOI:10.1002/anie.201400225

Reference yield: 66.0%

methyl o-formylbenzoate (4122-56-9) → methyl 5-phenyl-2-difluoromethylbenzoate (1018678-48-2)

Guidance literature:

With diethylamino-sulfur trifluoride; In ethanol; dichloromethane; at 20 ℃;

DOI:10.1055/s-0035-1560592

Reference yield:

bromodifluoromethane (1511-62-2) + 2-bromobenzoic acid methyl ester (610-94-6) → methyl 5-phenyl-2-difluoromethylbenzoate (1018678-48-2)

Guidance literature:

2-bromobenzoic acid methyl ester; With 2,6-dimethylpyridine; tris-(trimethylsilyl)silane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; 4,4'-di-tert-butyl-2,2'-bipyridine; In 1,2-dimethoxyethane; for 0.25h; Inert atmosphere;

bromodifluoromethane; In 1,2-dimethoxyethane; at 30 ℃; for 18h; Sealed tube; Irradiation; Inert atmosphere;

DOI:10.1002/anie.201807629

upstream raw materials:

methyl o-formylbenzoate

2-Methyl-benzoic acid methyl ester

bromodifluoromethane

2-bromobenzoic acid methyl ester

Downstream raw materials:

[2-(difluoromethyl)phenyl]methanol

C₄₈H₄₄F₂O₇

C₄₈H₄₄F₂O₇

C₄₈H₄₄F₂O₇

Refernces

• 1、 Bacauanu, Vlad,Cardinal, Sébastien,Yamauchi, Motoshi,Kondo, Masaru,Fernández, David F.,Remy, Richard,MacMillan, David W. C.. "Metallaphotoredox Difluoromethylation of Aryl Bromides". supporting information. p. 12543 - 12548. Retrieved 2018/09/18.
• 2、 Verhoog, Stefan,Pfeifer, Lukas,Khotavivattana, Tanatorn,Calderwood, Samuel,Collier, Thomas Lee,Wheelhouse, Katherine,Tredwell, Matthew,Gouverneur, Véronique. "Silver-Mediated 18F-Labeling of Aryl-CF3 and Aryl-CHF2 with 18F-Fluoride". supporting information. p. 25 - 28. Retrieved 2015/12/26.