501-00-8

Basic information

• Product Name: 3-Fluorophenylacetonitrile
• Synonyms: 3-fluoro-benzeneacetonitril;Acetonitrile, (m-fluorophenyl)-;m-Fluorobenzylcyanide;3-FLUOROBENZYL CYANIDE;3-FLUOROBENZENEACETONITRILE;3-FLUOROPHENYLACETONITRILE;M-FLUOROPHENYLACETONITRILE;3-Fluorophenylacetonitrile,98+%
• CAS NO: 501-00-8
• Molecular Formula: C₈H₆FN
• Molecular Weight: 135.14
• EINECS: 207-918-2
• Product Categories: Aromatic Nitriles;Fluorobenzene;Nitrile;Fluorine series
• Mol File: 501-00-8.mol
• Article Data: 9

Chemical Properties

• Melting Point: 21 °C
• Boiling Point: 113-114 °C18 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: clear light yellow to slightly brown liquid
• Density: 1.163 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0802mmHg at 25°C
• Refractive Index: n20/D 1.502(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 1861071
• CAS DataBase Reference: 3-Fluorophenylacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Fluorophenylacetonitrile(501-00-8)
• EPA Substance Registry System: 3-Fluorophenylacetonitrile(501-00-8)

Safety Data

• Hazard Codes: Xn,Xi,T
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39-24/25-36
• RIDADR: 3276
• WGK Germany: 3
• TSCA: T
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 501-00-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H6FN/c9-8-3-1-2-7(6-8)4-5-10/h1-3,6H,4H2

Synthetic route

potassium thioacyanate (333-20-0) + 4-methyl-N'-(3-fluorobenzylidene)benzenesulfonohydrazide (343229-18-5) → 3-fluorophenylacetonitrile (501-00-8)

Conditions	Yield
With copper(l) iodide; oxygen; 1,8-diazabicyclo[5.4.0]undec-7-ene; toluene-4-sulfonic acid hydrazide In 1-methyl-pyrrolidin-2-one; acetonitrile at 80℃; under 760.051 Torr; for 7h; Molecular sieve; Green chemistry;	65%

sodium cyanide (773837-37-9) + 1-(Bromomethyl)-3-fluorobenzene (456-41-7) → 3-fluorophenylacetonitrile (501-00-8)

Conditions	Yield
In dimethyl sulfoxide at 30℃;	50%
In dimethyl sulfoxide at 30℃;	50%

fluorobenzene (462-06-6) + chloroacetonitrile (107-14-2) → butanedinitrile (110-61-2) + 3-fluorophenylacetonitrile (501-00-8) + 2-fluorophenyl acetonitrile (326-62-5) + 4-fluorophenylacetonitrile (459-22-3)

Conditions	Yield
In acetonitrile Product distribution; Mechanism; Irradiation; different concentration ratios;	A 0.5% B n/a C n/a D n/a
In acetonitrile for 22h; Kinetics; Product distribution; Mechanism; Irradiation;

sodium cyanide (143-33-9) + 1-(Bromomethyl)-3-fluorobenzene (456-41-7) → 3-fluorophenylacetonitrile (501-00-8)

sodium cyanide (143-33-9) + m-fluorobenzyl chloride (456-42-8) → 3-fluorophenylacetonitrile (501-00-8)

phenylacetonitrile (140-29-4) → 3-fluorophenylacetonitrile (501-00-8) + 2-fluorophenyl acetonitrile (326-62-5) + 4-fluorophenylacetonitrile (459-22-3) + α-(Fluorophenyl)acetonitrile (10036-43-8)

Conditions	Yield
With triethylamine tris(hydrogen fluoride) In sulfolane at 50℃; electrolysis; Further byproducts given. Yields of byproduct given;	A n/a B n/a C n/a D 48 % Chromat.

potassium cyanide (151-50-8) + 1-(Bromomethyl)-3-fluorobenzene (456-41-7) → 3-fluorophenylacetonitrile (501-00-8)

Conditions	Yield
In ethanol

ethanolic solution of 3-fluoro-benzyl bromide + aqueous sodium cyanide solution → 3-fluorophenylacetonitrile (501-00-8)

m-Fluorotoluene (352-70-5) → 3-fluorophenylacetonitrile (501-00-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: benzene; bromine / Irradiation.UV-Licht View Scheme
Multi-step reaction with 2 steps 1: Cl2 / Irradiation View Scheme
Multi-step reaction with 2 steps 1: (bromination) 2: aq. ethanol View Scheme
Multi-step reaction with 2 steps 1: SO2Cl2 / Heating 2: ethanol / Heating View Scheme
Multi-step reaction with 2 steps 1: NBS View Scheme

sodium cyanide (773837-37-9) + 3-fluorobenzyl methanesulfonate (1000370-26-2) → 3-fluorophenylacetonitrile (501-00-8)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 0.5h;

Methyl formate (107-31-3) + 3-fluorophenylacetonitrile (501-00-8) → 2-(3-fluorophenyl)-3-hydroxyacrylonitrile (154858-22-7)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	100%
With sodium hydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;

3-fluorophenylacetonitrile (501-00-8) → 5-[(3-fluorophenyl)methyl]-1H-1,2,3,4-tetrazole

Conditions	Yield
With sodium azide; triethylamine hydrochloride In toluene at 110℃; for 16h; Inert atmosphere;	99%

2-Aminonicotinaldehyde (7521-41-7) + 3-fluorophenylacetonitrile (501-00-8) → 2-amino-3-(3-fluorophenyl)-1,8-naphthyridine (1082419-13-3)

Conditions	Yield
With potassium hydroxide In water for 0.0416667h; Microwave irradiation;	98%

ethanol (64-17-5) + 3-fluorophenylacetonitrile (501-00-8) → ethyl 2-(3-fluorophenyl)acetimidate hydrochloride

Conditions	Yield
With hydrogenchloride at 0℃; for 48h;	94%
With acetyl chloride at 0℃; Inert atmosphere;	87%
With hydrogenchloride at 0 - 5℃;
With hydrogenchloride In toluene at 0 - 20℃; for 1h;	6.12 g

3-fluorophenylacetonitrile (501-00-8) + methyl iodide (74-88-4) → 2-(3-fluoro-phenyl)-2-methyl-propionitrile (93748-10-8)

Conditions	Yield
Stage #1: 3-fluorophenylacetonitrile With lithium hexamethyldisilazane In tetrahydrofuran at -70 - -50℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at -50 - 20℃;	93%
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 17.5h;
With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; for 0.75h;

3-fluorophenylacetonitrile (501-00-8) + diisopropyl-carbodiimide (693-13-0) → C15H20FN3

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at 60℃; under 760.051 Torr; for 6h; Inert atmosphere; Sealed tube;	92%

3-fluorophenylacetonitrile (501-00-8) + 3,3,3-trifluoro-2-phenylpropene (384-64-5) → C26H18F5N

Conditions	Yield
With lithium tert-butoxide In dimethyl sulfoxide at 80℃; for 12h; Inert atmosphere;	92%

3-fluorophenylacetonitrile (501-00-8) + methyl chloroformate (79-22-1) → methyl 2-cyano-2-(3-fluorophenyl)acetate

Conditions	Yield
Stage #1: 3-fluorophenylacetonitrile With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at 20℃; for 0.166667h; Stage #2: methyl chloroformate In tetrahydrofuran; hexane at -78℃; for 4.5h;	91%

3-fluorophenylacetonitrile (501-00-8) + Phenyl azide (622-37-7) → C14H11FN4

Conditions	Yield
With caesium carbonate In water; dimethyl sulfoxide at 25℃; regioselective reaction;	90%

3-fluorophenylacetonitrile (501-00-8) + benzyl alcohol (100-51-6) → 2-(3-fluorophenyl)-3-phenylpropanamide

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triphenylphosphine; potassium hydroxide In tert-Amyl alcohol at 130℃; for 2h; Microwave irradiation;	89%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triphenylphosphine; potassium hydroxide at 130℃; for 2h; Microwave irradiation; Green chemistry;	89%

3-fluorophenylacetonitrile (501-00-8) + N-hydroxybenzenecarboximidamide (613-92-3) → 5-(3-fluorobenzyl)-3-phenyl-1,2,4-oxadiazole (1165931-58-7)

Conditions	Yield
With toluene-4-sulfonic acid; zinc(II) chloride In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	88%

3-fluorophenylacetonitrile (501-00-8) + benzoic acid tert-butyl ester (774-65-2) → N-(tert-butyl)-2-(3-fluorophenyl)acetamide (1091953-80-8)

Conditions	Yield
With zinc perchlorate In neat (no solvent) at 50℃; for 5h; Ritter Amidation;	87%

acetic acid tert-butyl ester (540-88-5) + 3-fluorophenylacetonitrile (501-00-8) → N-(tert-butyl)-2-(3-fluorophenyl)acetamide (1091953-80-8)

Conditions	Yield
With water; iodine In toluene at 110℃; for 6h; Ritter reaction;	86%

3-fluorophenylacetonitrile (501-00-8) + 2-amino-4-(N,N-dimethylamino)benzaldehyde (56669-96-6) → 3-(3-fluorophenyl)-N7,N7-dimethylquinoline-2,7-diamine

Conditions	Yield
Stage #1: 3-fluorophenylacetonitrile With potassium tert-butylate In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: 2-amino-4-(N,N-dimethylamino)benzaldehyde In N,N-dimethyl-formamide at 0 - 90℃;	84%
Stage #1: 3-fluorophenylacetonitrile With potassium tert-butylate In N,N-dimethyl-formamide at 0 - 20℃; for 0.25h; Stage #2: 2-amino-4-(N,N-dimethylamino)benzaldehyde In N,N-dimethyl-formamide at 0 - 90℃;

methanol (67-56-1) + 3-fluorophenylacetonitrile (501-00-8) → 2-(3-fluorophenyl)propanenitrile

Conditions	Yield
With cobalt(II) tetrafluoroborate hexahydrate; tris(2-diphenylphosphinoethyl)phosphine; potassium carbonate at 100℃; for 24h; Autoclave; Glovebox; Inert atmosphere;	84%

3-fluorophenylacetonitrile (501-00-8) + thiosemicarbazide (79-19-6) → 5-[(3-fluorophenyl)methyl]-1,3,4-thiadiazol-2-heptane (39181-54-9)

Conditions	Yield
In trifluoroacetic acid at 60℃; for 3h;	82%

3-fluorophenylacetonitrile (501-00-8) + 1-naphthyl tosylate (68211-49-4) → 2-(3-fluorophenyl)-2-(naphthalen-1-yl)acetonitrile

Conditions	Yield
With potassium phosphate; palladium diacetate; XPhos In dichloromethane; tert-butyl alcohol at 110℃; for 4h; Inert atmosphere; Schlenk technique; Sealed tube;	82%

3-fluorophenylacetonitrile (501-00-8) + 4-tert-butylphenyl mesylate (59970-38-6) → 2-(4-(tert-butyl)phenyl)-2-(3-fluorophenyl)acetonitrile

Conditions	Yield
With potassium phosphate; palladium diacetate; XPhos In dichloromethane; tert-butyl alcohol at 110℃; for 4h; Inert atmosphere; Schlenk technique; Sealed tube;	82%

3-fluorophenylacetonitrile (501-00-8) + N,N-bis(2-chloro-ethyl)-benzenemethanamine (55-51-6) → 1-benzyl-4-(3-fluorophenyl)piperidine-4-carbonitrile (1158750-54-9)

Conditions	Yield
Stage #1: 3-fluorophenylacetonitrile With 18-crown-6 ether; sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: N,N-bis(2-chloro-ethyl)-benzenemethanamine In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃;	80%
Stage #1: 3-fluorophenylacetonitrile With sodium hydride In tetrahydrofuran at 20℃; for 2h; Stage #2: N,N-bis(2-chloro-ethyl)-benzenemethanamine In tetrahydrofuran at 80℃; for 3h;	77%

3-fluorophenylacetonitrile (501-00-8) → 2-(3-fluorophenyl)ethan-1-amine hydrochloride

Conditions	Yield
Stage #1: 3-fluorophenylacetonitrile With borane-ammonia complex; C17H16BrMnN2O3S In hexane at 60℃; for 6h; Stage #2: With hydrogenchloride In diethyl ether; water	80%

3-fluorophenylacetonitrile (501-00-8) + acrylic acid methyl ester (292638-85-8) → C15H14NO3F

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 25℃; for 0.25h;	79%

3-fluorophenylacetonitrile (501-00-8) + acrylic acid methyl ester (292638-85-8) → methyl 5-cyano-5-(3-fluorophenyl)-2-oxocyclohexanecarboxylate

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 0 - 27℃; for 1h;	78.8%

3,4-dimethylbenzaldehyde (5973-71-7) + 3-fluorophenylacetonitrile (501-00-8) → (2E)-3-(3,4-dimethylphenyl)-2-(3-fluorophenyl)acrylonitrile (1379649-42-9)

Conditions	Yield
With sodium methylate In ethanol at 20℃; for 2h;	78%

3-fluorophenylacetonitrile (501-00-8) + N-(4-formylphenyl)carbazole (110677-45-7) → (Z)-3-(-4-(9H-carbazol-9-yl)phenyl)-2-(3-fluorophenyl)acrylonitrile

Conditions	Yield
With sodium methylate In methanol at 60℃; for 3h;	78%

2-Chlorobenzonitrile (873-32-5) + 3-fluorophenylacetonitrile (501-00-8) → 2-[Cyano-(3-fluoro-phenyl)-methyl]-benzonitrile (127667-15-6)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 3h;	77%

3-fluorophenylacetonitrile (501-00-8) + formic acid ethyl ester (109-94-4) → 2-(3'-Fluorophenyl)-3-oxopropanenitrile (75175-23-4)

Conditions	Yield
With sodium hydride In various solvent(s) at 70 - 80℃; for 6h; Carbonylation;	77%

3-fluorophenylacetonitrile (501-00-8) + benzenecarbothioamide (2227-79-4) → 3-(3-fluorobenzyl)-5-phenyl-1,2,4-thiadiazole

Conditions	Yield
Stage #1: 3-fluorophenylacetonitrile; benzenecarbothioamide With aluminum (III) chloride In acetic acid butyl ester at 70℃; for 5h; Sealed tube; Stage #2: With water; iodine In acetic acid butyl ester at 20℃; for 24h; Sealed tube; chemoselective reaction;	77%

1,1-Diphenylmethanol (91-01-0) + 3-fluorophenylacetonitrile (501-00-8) → N-benzhydryl-2-(3-fluorophenyl)acetamide (791126-32-4)

Conditions	Yield
With water; iodine In toluene at 110℃; for 7h; Ritter reaction;	76%

3-fluorophenylacetonitrile (501-00-8) + 1-naphthyl mesylate (38262-42-9) → 2-(3-fluorophenyl)-2-(naphthalen-1-yl)acetonitrile

Conditions	Yield
With potassium phosphate; palladium diacetate; XPhos In dichloromethane; tert-butyl alcohol at 110℃; for 4h; Inert atmosphere; Schlenk technique; Sealed tube;	76%

3-fluorophenylacetonitrile (501-00-8) + di-tert-butyl dicarbonate (24424-99-5) → N-(tert-butyl)-2-(3-fluorophenyl)acetamide (1091953-80-8)

Conditions	Yield
Stage #1: 3-fluorophenylacetonitrile; di-tert-butyl dicarbonate With copper(II) bis(trifluoromethanesulfonate) In neat (no solvent) at 20℃; for 5h; Ritter Amidation; Stage #2: With water Ritter Amidation;	76%

Upstream product

• 143-33-9 sodium cyanide 
• 456-41-7 1-(Bromomethyl)-3-fluorobenzene 
• 462-06-6 fluorobenzene 
• 107-14-2 chloroacetonitrile 
• 151-50-8 potassium cyanide 
• 63082-37-1 3,β,β-Trifluorostyrol 
• 773837-37-9 sodium cyanide 
• 1000370-26-2 3-fluorobenzyl methanesulfonate 
• 352-70-5 m-Fluorotoluene 
• 140-29-4 phenylacetonitrile 
• 456-42-8 m-fluorobenzyl chloride 
• 333-20-0 potassium thioacyanate 
• 343229-18-5 4-methyl-N'-(3-fluorobenzylidene)benzenesulfonohydrazide 

Downstream Products

• 370-45-6 2-(3-fluorophenyl)acetamide 
• 331-25-9 (3-fluorophenyl)acetic acid 
• 446-74-2 2-(3-fluorophenyl)-3-oxobutanenitrile 
• 1647-99-0 <3-Fluor-phenyl>-<4'-dimethylamino-phenyl>-α-cyan-azomethin 
• 122376-67-4 (3-Fluoro-phenyl)-pyridin-2-yl-acetonitrile 
• 75175-23-4 2-(3'-Fluorophenyl)-3-oxopropanenitrile 
• 486406-06-8 2-(3-fluorophenyl)-2-(pyridin-2-yl)acetamide 
• 170380-88-8 6-Chloro-3-(3-fluoro-phenyl)-indan-1-one 
• 1737-19-5 (3-fluorophenyl)acetone 
• 32347-95-8 m-Fluorphenylmalononitril 
• 32347-97-0 m-Fluorphenylmethylmalononitril 
• 248588-33-2 1-(3-fluorophenyl)cyclopropane-1-carboxylic acid 
• 116718-96-8 2,4,5-trihydroxyphenyl-3'-fluorobenzylketone 
• 54872-79-6 3-Fluorobenzamideoxime 

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