4-Fluorobenzoylacetonitrile

Base Information

• Chemical Name: 4-Fluorobenzoylacetonitrile
• CAS No.: 4640-67-9
• Molecular Formula: C9H6FNO
• Molecular Weight: 163.151
• Hs Code.: 29269090
• European Community (EC) Number: 627-421-8
• UNII: K1LTB8K2DH
• DSSTox Substance ID: DTXSID30382482
• Nikkaji Number: J2.260.392B
• Wikidata: Q27281825
• ChEMBL ID: CHEMBL3251049
• Mol file: 4640-67-9.mol

Synonyms:4-Fluorobenzoylacetonitrile;4640-67-9;3-(4-fluorophenyl)-3-oxopropanenitrile;p-Fluorobenzoylacetonitrile;3-(4-fluorophenyl)-3-oxopropionitrile;Acetonitrile, (p-fluorobenzoyl)-;UNII-K1LTB8K2DH;K1LTB8K2DH;3-Oxo-3-(4-fluorophenyl)propanenitrile;alpha-Cyano-4-fluoroacetophenone;3-(4-fluoro-phenyl)-3-oxo-propionitrile;Benzenepropanenitrile, 4-fluoro-beta-oxo-;MFCD00662062;4-fluoro-benzoylacetonitrile;(p-fluorobenzoyl)acetonitrile;(4-Fluorobenzoyl)acetonitrile;4-Fluoro Benzoyl Acetonitrile;SCHEMBL133680;CHEMBL3251049;DTXSID30382482;4-Fluorobenzoylacetonitrile, 97%;LOJBBLDAJBJVBZ-UHFFFAOYSA-N;HMS1741H18;BCP16716;CS-B0665;AM1017;BBL038588;CK2043;STK312286;AKOS000206981;PS-8749;3-(4-Fluorophenyl)-3-oxopropanenitrile;AC-24566;SY023307;.ALPHA.-CYANO-4-FLUOROACETOPHENONE;A7227;F0987;FT-0604212;EN300-14827;BENZENEPROPANENITRILE, 4-FLUORO-.BETA.-OXO-;Q27281825;Z104520972

Chemical Property of 4-Fluorobenzoylacetonitrile

Chemical Property:

• Vapor Pressure: 0.000547mmHg at 25°C
• Melting Point: 84-88 °C
• Refractive Index: 1.516
• Boiling Point: 311.9 °C at 760 mmHg
• PKA: 7.67±0.10(Predicted)
• Flash Point: 142.4 °C
• PSA: 40.86000
• Density: 1.207 g/cm³
• LogP: 1.92208
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Soluble in dimethylformamide, dimethyl sulfoxide.
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 163.043341977
• Heavy Atom Count: 12
• Complexity: 210

Purity/Quality:

99%, ^*data from raw suppliers

4-Fluorobenzoylacetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=O)CC#N)F
• Uses: 4-Fluorobenzoylacetonitrile is used as a reagent in the synthesis of Blonanserin (B595850); a 5-HT2 serotonin receptor and D2 dopamine receptor antagonist, used as an antipsychotic. 4-Fluorobenzoylacetonitrile is also used in the preparation of pyrazolopyrimidines as potential antimicrobial and antioxidant agents.

Technology Process of 4-Fluorobenzoylacetonitrile

There total 36 articles about 4-Fluorobenzoylacetonitrile 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: 93.14%

1-(4-fluorophenyl)-2-methoxyethan-1-one (247179-37-9) + acetonitrile (75-05-8,26809-02-9) → 3-(4-fluorophenyl)-3-oxopropionitrile (4640-67-9)

Guidance literature:

1-(4-fluorophenyl)-2-methoxyethan-1-one; With sodium hydride; In toluene; at 90 ℃; for 2h;

acetonitrile; In toluene; for 6.5h;

Reference yield: 93.0%

4-fluoro-N-methoxy-N-methylbenzamide (116332-54-8) + acetonitrile (75-05-8,26809-02-9) → 3-(4-fluorophenyl)-3-oxopropionitrile (4640-67-9)

Guidance literature:

acetonitrile; With methyllithium; lithium bromide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.5h; Inert atmosphere;

4-fluoro-N-methoxy-N-methylbenzamide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1.5h; Inert atmosphere;

DOI:10.1039/c4ob02398f

Reference yield: 92.39%

fluorobenzene (462-06-6) + malononitrile (109-77-3) → 3-(4-fluorophenyl)-3-oxopropionitrile (4640-67-9)

Guidance literature:

With trifluorormethanesulfonic acid; In chloroform; at 20 - 80 ℃; for 12.5h;

upstream raw materials:

α-(tert-butylcarboxy)-β-hydroxy-p-fluorocinnamonitrile

sodium cyanide

2-Chloro-4'-fluoroacetophenone

4-fluorobenzoic acid ethyl ester

Downstream raw materials:

3,4-dihydroxy-(p-fluorobenzoyl)-cis-cinnamonitrile

(2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-(4-fluoro-phenyl)-methanone

(2-aminothiophen-3-yl)(4-fluorophenyl)methanone

3-amino-1-(4-fluorophenyl)-propan-1-ol

Refernces

• 1、 Liu, Chong,Yuan, Jing,Zhang, Zhenfeng,Gridnev, Ilya D.,Zhang, Wanbin. "Asymmetric Hydroacylation Involving Alkene Isomerization for the Construction of C3-Chirogenic Center". supporting information. p. 8997 - 9002. Retrieved 2021/03/16.
• 2、 -. "Method for synthesizing beta-ketonitrile and derivatives thereof". Paragraph 0056-0060. . Retrieved 2021/04/21.