2-bromo-2,2-difluoro-N-(2-hydroxyphenyl)acetamide

Base Information

• Chemical Name: 2-bromo-2,2-difluoro-N-(2-hydroxyphenyl)acetamide
• CAS No.: 239136-81-3
• Molecular Formula: C₈H₆BrF₂NO₂
• Molecular Weight: 266.042
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID60442846
• Wikidata: Q82260385
• Mol file: 239136-81-3.mol

Synonyms:2-bromo-2,2-difluoro-N-(2-hydroxyphenyl)acetamide;239136-81-3;DTXSID60442846;KYMHHFWTYFGZEK-UHFFFAOYSA-N;2-bromanyl-2,2-bis(fluoranyl)-N-(2-hydroxyphenyl)ethanamide;MFCD11035865;AKOS025311273;GS-1902;CS-0359085;A816986

Chemical Property of 2-bromo-2,2-difluoro-N-(2-hydroxyphenyl)acetamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.612
• Boiling Point: 326.017°C at 760 mmHg
• Flash Point: 150.97°C
• PSA: 52.82000
• Density: 1.834g/cm³
• LogP: 2.96790
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 264.95500
• Heavy Atom Count: 14
• Complexity: 225

Purity/Quality:

97% ^*data from raw suppliers

2-Bromo-2,2-difluoro-N-(2-hydroxyphenyl)acetamide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)NC(=O)C(F)(F)Br)O

Technology Process of 2-bromo-2,2-difluoro-N-(2-hydroxyphenyl)acetamide

There total 2 articles about 2-bromo-2,2-difluoro-N-(2-hydroxyphenyl)acetamide 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%

Ethyl bromodifluoroacetate (667-27-6) + 2-amino-phenol (95-55-6) → 2-Bromo-2,2-difluoro-N-(2-hydroxyphenyl)acetamide (239136-81-3)

Guidance literature:

With triethylamine; In ethyl acetate; for 1h; Heating;

DOI:10.1016/S0022-1139(99)00007-X

Reference yield:

2-(1-bromodifluoromethyl)benzo-1,3-oxazole (186828-50-2) → 2-(Difluoromethyl)benzoxazole (91437-09-1) + 2-Bromo-2,2-difluoro-N-(2-hydroxyphenyl)acetamide (239136-81-3) + 2,2-difluoro-N-(2-hydroxy-phenyl)-acetamide

Guidance literature:

With N,N,N,N-tetraethylammonium tetrafluoroborate; In N,N-dimethyl-formamide; Electrochemical reaction;

DOI:10.1016/S0022-1139(01)00378-5

Reference yield:

2-Bromo-2,2-difluoro-N-(2-hydroxyphenyl)acetamide (239136-81-3) → N-{2-[(tert-butyldimethylsilyl)oxy]phenyl}-N-(2-fluoroethynyl)benzamide + 4-benzoyl-2-fluorobenzo[b][1,4]oxazine

Guidance literature:

Multi-step reaction with 4 steps

1: 1H-imidazole / dichloromethane / 17 h / 20 °C / Inert atmosphere

2: dimethylsulfide borane complex / dichloromethane / 72 h / Reflux

3: triethylamine / dichloromethane / 5 h / Reflux

4: sodium hexamethyldisilazane / tetrahydrofuran / 6 h / 20 °C

With 1H-imidazole; dimethylsulfide borane complex; sodium hexamethyldisilazane; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/acs.joc.5b00507

upstream raw materials:

Ethyl bromodifluoroacetate

2-amino-phenol

2-(1-bromodifluoromethyl)benzo-1,3-oxazole

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