3-(2,6-Difluorophenyl)-3-oxopropanenitrile

Base Information

• Chemical Name: 3-(2,6-Difluorophenyl)-3-oxopropanenitrile
• CAS No.: 40017-76-3
• Molecular Formula: C9H5F2NO
• Molecular Weight: 181.142
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID60504998
• Wikidata: Q82359818
• Mol file: 40017-76-3.mol

Synonyms:40017-76-3;3-(2,6-difluorophenyl)-3-oxopropanenitrile;2,6-Difluorobenzoylacetonitrile;2,6-Difluorophenacyl cyanide;3-(2',6'-DIFLUOROPHENYL)-3-OXOPROPANENITRILE;MFCD02260806;SCHEMBL7001279;DTXSID60504998;2',6'-Difluorobenzoylacetonitrile;AM976;AKOS000168127;AB93144;SY012836;A6684;CS-0314818;FT-0604197;Benzenepropanenitrile, 2,6-difluoro-beta-oxo-;1,2-[BIS-(4-TRIFLUOROMETHYL)PHENYL]ETHANE97

Chemical Property of 3-(2,6-Difluorophenyl)-3-oxopropanenitrile

Chemical Property:

• Boiling Point: 289.9 °C at 760 mmHg
• Flash Point: 129.2 °C
• PSA: 40.86000
• Density: 1.3 g/cm³
• LogP: 2.06118
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 181.03392011
• Heavy Atom Count: 13
• Complexity: 235

Purity/Quality:

98.5% ^*data from raw suppliers

2,6-Difluorobenzoylacetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)F)C(=O)CC#N)F
• Uses: 2,6-Difluorobenzoylacetonitrile is used in the synthesis of thienodiazepinones which can have poor central nervous system depressant activity.

Technology Process of 3-(2,6-Difluorophenyl)-3-oxopropanenitrile

There total 6 articles about 3-(2,6-Difluorophenyl)-3-oxopropanenitrile 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: 70.0%

potassium cyanide (151-50-8) + 2-bromo-1-(2,6-difluorophenyl)ethanone (56159-89-8) → 3-(2,6-difluorophenyl)-3-oxopropanenitrile (40017-76-3)

Guidance literature:

In ethanol; for 1.5h;

DOI:10.1002/ardp.19803130704

Reference yield: 62.0%

methyl 2,6-difluorobenzoate (13671-00-6) + acetonitrile (75-05-8,26809-02-9) → 3-(2,6-difluorophenyl)-3-oxopropanenitrile (40017-76-3)

Guidance literature:

acetonitrile; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1.03333h; Inert atmosphere;

methyl 2,6-difluorobenzoate; In tetrahydrofuran; at -78 - 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.0c01777

Reference yield:

2,6 difluorobenzonitrile (1897-52-5) → 3-(2,6-difluorophenyl)-3-oxopropanenitrile (40017-76-3)

Guidance literature:

Multi-step reaction with 2 steps

1: Na / benzene / Heating

2: conc. aq. HCl

With hydrogenchloride; sodium; In benzene;

DOI:10.1002/ardp.19803130704

upstream raw materials:

potassium cyanide

2-bromo-1-(2,6-difluorophenyl)ethanone

2,6 difluorobenzonitrile

2,6-difluoroacetophenone

Downstream raw materials:

5-(2,6-difluorophenyl)-2H-pyrazole-3-yl-amine

7-chloro-5-(2,6-difluoro-phenyl)-1,3-dihydro-thieno[2,3-e][1,4]diazepin-2-one

5-(2,6-difluoro-phenyl)-1-methyl-1,3-dihydro-thieno[2,3-e][1,4]diazepin-2-one

5-(2,6-difluoro-phenyl)-1,3-dihydro-thieno[2,3-e][1,4]diazepin-2-one

Refernces

• 1、 Binder,Hromatka,Noe,Hillebrand,Veit,Blum. "Thiophene as a structural element of physiologically active compounds. IV. o-substituted 5-phenylthieno[2,3-e][1,4]diazepines". . p. 587 - 602. Retrieved 2007/10/02.