2-(4-Fluorophenyl)-2-oxoacetyl chloride

Base Information

• Chemical Name: 2-(4-Fluorophenyl)-2-oxoacetyl chloride
• CAS No.: 105457-90-7
• Molecular Formula: C8H4 Cl F O2
• Molecular Weight: 186.57
• Hs Code.: 2918300090
• DSSTox Substance ID: DTXSID70456156
• Wikidata: Q82278382
• Mol file: 105457-90-7.mol

Synonyms:105457-90-7;2-(4-fluorophenyl)-2-oxoacetyl chloride;Benzeneacetyl chloride,4-fluoro-a-oxo-;(4-Fluorophenyl)(oxo)acetyl chloride;Benzeneacetyl chloride, 4-fluoro-alpha-oxo- (9CI);SCHEMBL8386482;DTXSID70456156;2-(4-fluorophenyl)-2-oxoacetylchloride;EN300-152706

Chemical Property of 2-(4-Fluorophenyl)-2-oxoacetyl chloride

Chemical Property:

• Boiling Point: 279.2±42.0 °C(Predicted)
• PSA: 34.14000
• Density: 1.395±0.06 g/cm3(Predicted)
• LogP: 1.77380
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 185.9883852
• Heavy Atom Count: 12
• Complexity: 197

Purity/Quality:

99% ^*data from raw suppliers

2-(4-Fluorophenyl)-2-oxoacetylchloride 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-(4-Fluorophenyl)-2-oxoacetyl chloride

There total 5 articles about 2-(4-Fluorophenyl)-2-oxoacetyl chloride 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:

fluorobenzene (462-06-6) + Ethyl oxalyl chloride (4755-77-5) → 4-fluorophenylglyoxylic acid chloride (105457-90-7)

Guidance literature:

With aluminum (III) chloride; In dichloromethane; at 0 - 20 ℃; for 8h;

DOI:10.1021/acs.orglett.6b00748

Reference yield:

ethyl 4-fluorobenzoylformate (1813-94-1) → 4-fluorophenylglyoxylic acid chloride (105457-90-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide; water / tetrahydrofuran / 6 h / Reflux

2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 20 °C

With oxalyl dichloride; water; N,N-dimethyl-formamide; sodium hydroxide; In tetrahydrofuran; dichloromethane;

DOI:10.1002/anie.201400147

Reference yield:

1-(4-fluorophenyl)ethanone (403-42-9) → 4-fluorophenylglyoxylic acid chloride (105457-90-7)

Guidance literature:

Multi-step reaction with 2 steps

1: selenium(IV) oxide / pyridine / 6 h / 90 °C / Inert atmosphere

2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C

With selenium(IV) oxide; oxalyl dichloride; N,N-dimethyl-formamide; In pyridine; dichloromethane;

DOI:10.1002/adsc.201500079

upstream raw materials:

1-Bromo-4-fluorobenzene

ethyl 4-fluorobenzoylformate

2-(4-fluorophenyl)-2-oxoacetic acid

1-(4-fluorophenyl)ethanone

Downstream raw materials:

4-Fluor-N-isopropyl-phenylglyoxylohydroxamsaeure

C₂₃H₁₈FNO₂

tert-butyl 2-oxo-2-(4-fluorophenyl)acetate

(Z)-tert-butyl 2-(4-fluorophenyl)-3-nitroacrylate

Refernces

• 1、 Junaid, Qazi Mohammad,Kandasamy, Jeyakumar,Popuri, Sureshbabu,Sabiah, Shahulhameed,Singh, Shweta. "Diversification of α-ketoamides: Via transamidation reactions with alkyl and benzyl amines at room temperature". supporting information. p. 7134 - 7140. Retrieved 2021/08/30.
• 2、 Li, Jing,Shen, Jiefeng,Xia, Chao,Wang, Yanzhao,Liu, Delong,Zhang, Wanbin. "Asymmetric Hydrogenation of α-Substituted Acrylic Acids Catalyzed by a Ruthenocenyl Phosphino-oxazoline-Ruthenium Complex". supporting information. p. 2122 - 2125. Retrieved 2016/06/01.