117482-84-5

Basic information

• Product Name: 3-Chloro-4-fluorobenzonitrile
• Synonyms: 3-CHLORO-4-FLUOROBENZONITRILE;3-Chloro-4-fluorobenzonitrile 99%;3-Chloro-4-fluorobenzonitrile99%;3-Chloro-4-fluorobenzonitrile, 98+%;3-chloro-4-fluorophenyl-carbonitrile
• CAS NO: 117482-84-5
• Molecular Formula: C₇H₃ClFN
• Molecular Weight: 155.56
• EINECS: -0
• Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Nitriles;Fluorobenzene;Nitrile;C6 to C7;Cyanides/Nitriles;Nitrogen Compounds;Fluorine series;Pyridines
• Mol File: 117482-84-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: 69-71 °C(lit.)
• Boiling Point: 135 °C / 65mmHg
• Flash Point: 83 °C
• Appearance: Slightly yellow crystalline powder
• Density: 1.3760 (estimate)
• Vapor Pressure: 0.0035mmHg at 25°C
• Refractive Index: 1.569
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• BRN: 4740501
• CAS DataBase Reference: 3-Chloro-4-fluorobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloro-4-fluorobenzonitrile(117482-84-5)
• EPA Substance Registry System: 3-Chloro-4-fluorobenzonitrile(117482-84-5)

Safety Data

• Hazard Codes: Xn,T,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39-36/37/39
• RIDADR: 3439
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 117482-84-5(Hazardous Substances Data)

Usage

Chemical Properties

Slightly yellow crystalline powder

Uses

3-Chloro-4-fluorobenzonitrile may be used in the preparation of ethyl 5-(2-chloro-4-cyanophenoxy)indoline-1-carboxylate and 3-chloro-4-(indolin-5-yloxy)benzonitrile.

General Description

The FTIR and Raman spectra of 3-chloro-4-fluorobenzonitrile by ab initio HF and density functional method has been reported. Reaction of 3-chloro-4-fluorobenzonitrile with potassium fluoride in 1,3-dimethylimidazolidine-2-one (DMI) has been reported.

InChI:InChI=1/C11H6BrF3/c12-10-6-2-3-7-8(10)4-1-5-9(7)11(13,14)15/h1-6H

Synthetic route

(N,N-dimethylimidazolidino)tris-(diethylamino)phosphazenium chloride + 3,4-dichloro-benzonitrile (6574-99-8) → 3-chloro-4-fluorobenzonitrile (117482-84-5)

Conditions	Yield
With potassium fluoride In water; dimethyl sulfoxide	92%

3-Chloro-4-fluorobenzaldehyde (34328-61-5) → 3-chloro-4-fluorobenzonitrile (117482-84-5)

Conditions	Yield
With hydroxylamine hydrochloride; zinc(II) oxide for 0.0166667h; Microwave irradiation; neat (no solvent);	91%
With hydroxylamine hydrochloride; toluene-4-sulfonic acid for 0.0111111h; Microwave irradiation;	85%

3-chloro-4-fluoro-thiobenzamide (130560-97-3) → 3-chloro-4-fluorobenzonitrile (117482-84-5)

Conditions	Yield
With methylene blue; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 25℃; Sealed tube; Irradiation;	89%

3,4-dichloro-benzonitrile (6574-99-8) → 3-chloro-4-fluorobenzonitrile (117482-84-5)

Conditions	Yield
With fluorosulfonyl fluoride; tetramethylammonium 2,6-dimethylphenoxide In N,N-dimethyl-formamide at 20℃; for 24h; Sealed tube;	85%
With tetrabutyl ammonium fluoride In dimethyl sulfoxide at 20℃; for 0.333333h;
With potassium fluoride In cyclohexane; water at 130℃; for 3h; Solvent; Temperature;

2-(3-chloro-4-fluorophenyl)acetic acid (705-79-3) → 3-chloro-4-fluorobenzonitrile (117482-84-5)

Conditions	Yield
With oxygen; copper(II) trifluoroacetate; urea In dimethyl sulfoxide at 110℃; for 24.5h; Green chemistry;	82%

3,4-dichloro-benzonitrile (6574-99-8) → 3,4-Difluorobenzonitrile (64248-62-0) + 3-chloro-4-fluorobenzonitrile (117482-84-5)

Conditions	Yield
With potassium fluoride In various solvent(s) at 225℃; for 6h;	A 11% B 78%
With potassium fluoride In various solvent(s) at 225℃; for 6h; Product distribution; variation of solvent, temperature, concentration of reagent and catalyst, also without catalyst and with pressure;	A 65 % Chromat. B 23 % Chromat.

C14H7ClN2OS + 2-fluoro-1,3-benzothiazole (1123-98-4) → 3-chloro-4-fluorobenzonitrile (117482-84-5) + 1-(2-benzothiazolyl)benzothiazolone (4846-47-3)

Conditions	Yield
With bis[1,2-bis(diphenylphosphino)benzene]hydriderhodium(I) In chlorobenzene for 3h; Inert atmosphere; Reflux;

3-chloro-4-fluorobenzonitrile (117482-84-5) + 1-benzyl-1H-indol-5-ol (142769-36-6) → 4-[(1-benzyl-1H-indol-5-yl)oxy]-3-chlorobenzonitrile (161460-39-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 6h; Substitution;	100%

indole (120-72-9) + 3-chloro-4-fluorobenzonitrile (117482-84-5) → 3-chloro-4-(1H-indol-1-yl)benzonitrile (930572-44-4)

Conditions	Yield
Stage #1: indole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Stage #2: 3-chloro-4-fluorobenzonitrile at 45℃; for 1.5h;	100%
Stage #1: indole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Stage #2: 3-chloro-4-fluorobenzonitrile In N,N-dimethyl-formamide at 45℃; for 1.5h;	100%

tert-butyl (13-(4-((3,5-dimethyl-1H-pyrazol-4-yl)methyl)phenyl)-13-oxo-3,6,9-trioxa-12-azatridec-1-yl)carbamate + 3-chloro-4-fluorobenzonitrile (117482-84-5) → tert-butyl (13-(4-((1-(2-chloro-4-cyanophenyl)-3,5-dimethyl-1H-pyrazol-4-yl)methyl)phenyl)-13-oxo-3,6,9-trioxa-12-azatridec-1-yl)carbamate

Conditions	Yield
Stage #1: tert-butyl (13-(4-((3,5-dimethyl-1H-pyrazol-4-yl)methyl)phenyl)-13-oxo-3,6,9-trioxa-12-azatridec-1-yl)carbamate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 3-chloro-4-fluorobenzonitrile In N,N-dimethyl-formamide at 20℃;	97%

2-Amino-1-propanol (6168-72-5) + 3-chloro-4-fluorobenzonitrile (117482-84-5) → 3-chloro-4-(2-hydroxy-1-methyl-ethylamino)-benzonitrile (864297-00-7)

Conditions	Yield
In dimethyl sulfoxide at 60℃; for 2h;	96%
In dimethyl sulfoxide at 60℃; for 2h;	96%

3-chloro-4-fluorobenzonitrile (117482-84-5) + isopropyl alcohol (67-63-0) → 3-chloro-4-isopropoxybenzonitrile (916596-04-8)

Conditions	Yield
With sodium hydride In tetrahydrofuran at -10 - 10℃; for 3h;	95%
With sodium hydride
With sodium hydride In tetrahydrofuran at -10 - 10℃; for 2h;

3-chloro-4-fluorobenzonitrile (117482-84-5) + ethyl 5-hydroxy-2,3-dihydroindole-1-carboxylate (170147-32-7) → ethyl 5-(2-chloro-4-cyanophenoxy)indoline-1-carboxylate (170148-05-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 5h;	94%

3-chloro-4-fluorobenzonitrile (117482-84-5) + 2-methyl-1-pyrrolidine (765-38-8) → 3-chloro-4-(2-methyl-pyrrolidin-1-yl)-benzonitrile (864296-26-4)

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 90℃; for 60h;	94%
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 90℃; for 60h;	94%

propylamine (107-10-8) + 3-chloro-4-fluorobenzonitrile (117482-84-5) → 3-chloro-4-(propylamino)benzonitrile (917388-71-7)

Conditions	Yield
In tetrahydrofuran at 50℃;	94%

3-chloro-4-fluorobenzonitrile (117482-84-5) + 4-methoxy-phenol (150-76-5) → 3-chloro-4-(4-methoxyphenoxy)benzonitrile

Conditions	Yield
With potassium carbonate In acetonitrile Inert atmosphere; Reflux;	94%

4-n-propylsyringol (6766-82-1) + 3-chloro-4-fluorobenzonitrile (117482-84-5) → 3-chloro-4-(2,6-dimethoxy-4-propylphenoxy)benzonitrile (1240613-84-6)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 100℃; for 12h; Inert atmosphere;	93%

dimethyl-pyrrolidin-3-yl-amine (69478-75-7, 108138-38-1, 132883-44-4, 132958-72-6) + 3-chloro-4-fluorobenzonitrile (117482-84-5) → 3-chloro-4-(3-dimethylamino-pyrrolidin-1-yl)-benzonitrile (864297-30-3)

Conditions	Yield
With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃; for 3.5h;	92%
With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃; for 3.5h;	92%

(1R,2S)-2-amino-1-(6-methoxypyridin-3-yl)propan-1-ol (1196452-56-8) + 3-chloro-4-fluorobenzonitrile (117482-84-5) → 4-((1R,2S)-2-amino-1-(6-methoxypyridin-3-yl)propoxy)-3-chlorobenzonitrile

Conditions	Yield
Stage #1: (1R,2S)-2-amino-1-(6-methoxypyridin-3-yl)propan-1-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 18 - 25℃; for 0.5h; Inert atmosphere; Stage #2: 3-chloro-4-fluorobenzonitrile In N,N-dimethyl-formamide; mineral oil at 18 - 25℃; Inert atmosphere;	92%

[N-(2-aminoethyl)-N-{N-(2-pyrimidinyl)-piperidin-4-ylmethyl}]-1-methyl-1H-imidazole-4-sulfonamide (1247018-10-5) + 3-chloro-4-fluorobenzonitrile (117482-84-5) → [N-{2-(2-chloro-4-cyanophenyl)-aminoethyl}-N-{N-(2-pyrimidinyl)-piperidin-4-ylmethyl}]-1-methyl-1H-imidazole-4-sulfonamide (1247018-12-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 120℃; for 48h; Inert atmosphere;	91%

4-hydroxy-benzaldehyde (123-08-0) + 3-chloro-4-fluorobenzonitrile (117482-84-5) → 3-chloro-4-(4-formylphenoxy)benzonitrile (676494-58-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2h; Inert atmosphere;	91%
With potassium carbonate In N,N-dimethyl-formamide for 2h; Heating;	84%

3-chloro-4-fluorobenzonitrile (117482-84-5) + 2-amino-1-benzylamine (4403-69-4) → C14H10ClFN2

Conditions	Yield
With copper(II) cinnamic acid complex In toluene at 110℃; Green chemistry;	91%

3-chloro-4-fluorobenzonitrile (117482-84-5) + sodium thiomethoxide (5188-07-8) → 3-chloro-4-methylsulfanylbenzonitrile (189628-36-2)

Conditions	Yield
In N,N-dimethyl-formamide at 80℃;	90%
In N,N-dimethyl-formamide at 80℃; for 18h;

3-chloro-4-fluorobenzonitrile (117482-84-5) + 4-anilinophenol (122-37-2) → 4-(4-anilinophenoxy)-3-chlorobenznitrile (158769-75-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 5h;	90%

3-chloro-4-fluorobenzonitrile (117482-84-5) + N-acetylhomopiperizine (61903-11-5) → 4-(4-N-acetyl-[1,4]diazepan-1-yl)-3-chloro-benzonitrile (864296-08-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 90℃; for 6h;	90%
With N-ethyl-N,N-diisopropylamine at 90℃; for 6h;	90%

(S)-1-(5-bromo-2-methoxyphenyl)ethanamine hydrochloride + 3-chloro-4-fluorobenzonitrile (117482-84-5) → (S)-4-((1-(5-bromo-2-methoxyphenyl)ethyl)amino)-3-chlorobenzonitrile

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 120℃; for 16h;	90%

N-Boc-1,3-diaminopropane (75178-96-0) + 3-chloro-4-fluorobenzonitrile (117482-84-5) → 4-(3-tert-butoxycarbonylamino-propyl-amino)-3-chloro-benzonitrile (864296-50-4)

Conditions	Yield
With 4-methyl-morpholine In DMF (N,N-dimethyl-formamide) at 20 - 105℃; for 3.83333h;	89%
With 4-methyl-morpholine In DMF (N,N-dimethyl-formamide) at 20 - 105℃; for 3.83333h;	89%

vanillin (121-33-5) + 3-chloro-4-fluorobenzonitrile (117482-84-5) → 4-(4-formyl-2-methoxyphenoxy)-3-chlorobenzonitrile (1055361-86-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 95℃; for 5h;	89%
With lithium carbonate In dimethyl sulfoxide at 100℃; for 16h;	80%

4-(4-fluorobenzyl)-3,5-dimethyl-1H-pyrazole (1189140-61-1) + 3-chloro-4-fluorobenzonitrile (117482-84-5) → 3-chloro-4-[4-(4-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-1-yl]benzonitrile (1189135-53-2)

Conditions	Yield
Stage #1: 4-(4-fluorobenzyl)-3,5-dimethyl-1H-pyrazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: 3-chloro-4-fluorobenzonitrile In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 20h;	89%

4-Chloro-3-isopropyl-1H-pyrazolo[3,4-b]pyridine (1260535-94-1) + 3-chloro-4-fluorobenzonitrile (117482-84-5) → 3-Chloro-4-{4-chloro-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrile (1260538-98-4)

Conditions	Yield
Stage #1: 4-Chloro-3-isopropyl-1H-pyrazolo[3,4-b]pyridine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: 3-chloro-4-fluorobenzonitrile In N,N-dimethyl-formamide; mineral oil at 60℃; for 1h;	85%

3-chloro-4-fluorobenzonitrile (117482-84-5) + 2-amino-1-benzylamine (4403-69-4) → C14H8ClFN2

Conditions	Yield
With copper(II) cinnamic acid complex; oxygen In toluene at 110℃; Green chemistry;	84%

3-chloro-4-fluorobenzonitrile (117482-84-5) → 3-chloro-4-fluoro-N'-hydroxybenzenecarboximidamide (885963-77-9)

Conditions	Yield
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water at 70℃; for 8h;	82.5%
With hydroxylamine hydrochloride; triethylamine In ethanol at 50℃; for 13h;	74%
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water for 8h; Reflux;	69%

Upstream product

• 34328-61-5 3-Chloro-4-fluorobenzaldehyde 
• 705-79-3 2-(3-chloro-4-fluorophenyl)acetic acid 
• 130560-97-3 3-chloro-4-fluoro-thiobenzamide 
• 1123-98-4 2-fluoro-1,3-benzothiazole 
• 6574-99-8 3,4-dichloro-benzonitrile 

Downstream Products

• 170147-91-8 3-chloro-4-(1H-indol-5-yloxy)benzonitrile 
• 170147-92-9 3-chloro-4-(1-methyl-1H-indol-5-yloxy)-benzonitrile 
• 161460-37-3 3-chloro-4[(2-phenyl-1H-indol-5-yl)oxy]benzonitrile 
• 320783-95-7 3-chloro-4-[4-(N-methylamino)phenoxy]benzonitrile 
• 170148-05-7 ethyl 5-(2-chloro-4-cyanophenoxy)indoline-1-carboxylate 
• 170148-06-8 5-(2-chloro-4-cyano-phenoxy)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester 
• 158769-75-6 4-(4-anilinophenoxy)-3-chlorobenznitrile 
• 130560-97-3 3-chloro-4-fluoro-thiobenzamide 
• 852241-36-2 4-(8-azabicyclo[3.2.1]oct-8-yl)-3-chlorobenzonitrile 
• 864297-00-7 3-chloro-4-(2-hydroxy-1-methyl-ethylamino)-benzonitrile 
• 864296-50-4 4-(3-tert-butoxycarbonylamino-propyl-amino)-3-chloro-benzonitrile 
• 864296-08-2 4-(4-N-acetyl-[1,4]diazepan-1-yl)-3-chloro-benzonitrile 
• 864297-30-3 3-chloro-4-(3-dimethylamino-pyrrolidin-1-yl)-benzonitrile 
• 864296-26-4 3-chloro-4-(2-methyl-pyrrolidin-1-yl)-benzonitrile 

Relevant articles and documents

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