6574-99-8

Basic information

• Product Name: 3,4-Dichlorobenzonitrile
• Synonyms: 3,4-Dichlorobenzonitrle;3,4-Dichlorbenzonitril;3,4-Dichlorobenzonitrile 97%;3,4-DICHLOROBENZONITRILE HPLC99%;3,4-Dichlorobenzonitrile ,99%;3,4-Dichlorobenzonit;Benzonitrile, 3,4-dichloro-;BUTTPARK 87\02-72
• CAS NO: 6574-99-8
• Molecular Formula: C₇H₃Cl₂N
• Molecular Weight: 172.01
• EINECS: 229-494-8
• Product Categories: Aromatic Nitriles;Nitrile;Chlorine Compounds;Nitriles;C6 to C7;Cyanides/Nitriles;Nitrogen Compounds;intermediate
• Mol File: 6574-99-8.mol
• Article Data: 29

Chemical Properties

• Melting Point: 74-78 °C(lit.)
• Boiling Point: 235.5 °C at 760 mmHg
• Flash Point: 95 °C
• Appearance: White to brown/Powder or Crystalline Powder
• Density: 1.4 g/cm³
• Vapor Pressure: 0.0498mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water
• BRN: 2326352
• CAS DataBase Reference: 3,4-Dichlorobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dichlorobenzonitrile(6574-99-8)
• EPA Substance Registry System: 3,4-Dichlorobenzonitrile(6574-99-8)

Safety Data

• Hazard Codes: Xn,T,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• RIDADR: 3276
• WGK Germany: 2
• TSCA: N
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 6574-99-8(Hazardous Substances Data)

Usage

Description

3,4-Dichlorobenzonitrile (3,4-DCBN) is an aromatic nitrile compound characterized by its white solid appearance. It is synthesized from 3,4-dichlorobenzamide and is known for its versatile chemical properties, making it a valuable intermediate in the synthesis of various organic compounds.

Uses

Used in Pharmaceutical Industry:
3,4-Dichlorobenzonitrile is used as a synthetic intermediate for the preparation of various pharmaceutical compounds. Its application reason lies in its ability to be transformed into different molecules with potential therapeutic properties.
Used in Chemical Synthesis:
3,4-Dichlorobenzonitrile is used as a key building block in the synthesis of several organic compounds, including:
1. 3,4-difluorobenzonitrile: It serves as a precursor for the development of molecules with potential applications in various fields, such as pharmaceuticals and materials science.
2. 3-chloro-4-fluorobenzonitrile: 3,4-Dichlorobenzonitrile is utilized in the creation of fluorinated aromatic compounds, which have a wide range of applications in the chemical industry.
3. 5-chloromethyl-3-(3,4-dichlorophenyl)isoxazole: This molecule can be used in the development of novel isoxazole-based compounds with potential applications in various industries.
4. N-[3-(2-pyridyl)isoquinolin-1-yl]-3,4-dichlorobenzamidine: This complex molecule can be employed in the design and synthesis of new compounds with potential applications in the pharmaceutical and chemical industries.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C7H3Cl2N/c8-6-2-1-5(4-10)3-7(6)9/h1-3H

Synthetic route

4-bromo-1,2-dichlorobenzene (18282-59-2) + copper(I) cyanide (544-92-3) → 3,4-dichloro-benzonitrile (6574-99-8)

Conditions	Yield
With L-proline In N,N-dimethyl-formamide at 128℃; for 3h; Temperature;	96.5%

3,4-dichlorobenzaldehyde oxime (5331-92-0) → 3,4-dichloro-benzonitrile (6574-99-8)

Conditions	Yield
With trifluoromethylsulfonic anhydride; triethylamine; triphenylphosphine In dichloromethane at 0℃; for 0.166667h;	95%
With diethyl cyanophosphonate; triethylamine In dichloromethane at 20℃; for 10h; Inert atmosphere;	84%
With bis(trichloromethyl) carbonate In chloroform at 20℃;
With thionyl chloride In benzene Heating;
With fluorosulfonyl fluoride; sodium carbonate In dimethyl sulfoxide at 20℃; for 12h;	337 mg

3,4-dichloro-1-trichloromethylbenzene (13014-24-9) → 3,4-dichloro-benzonitrile (6574-99-8)

Conditions	Yield
With copper; ammonium chloride at 120 - 220℃; for 20h; Temperature; Reagent/catalyst; Green chemistry;	94.6%

3,4-dichlorobenzamide (2670-38-4) → 3,4-dichloro-benzonitrile (6574-99-8)

Conditions	Yield
With thionyl chloride In chlorobenzene for 15h; Heating;	93%

3.4-Dichlorbenzaldehyd-phenylhydrazon (21719-62-0) → N,N-dimethyl-N'-phenylcarbamimidic chloride (7684-30-2) + 3,4-dichloro-benzonitrile (6574-99-8)

Conditions	Yield
With dichloromethylenedimethyliminium chloride In 1,2-dichloro-ethane 1.) room temp., 1 h, 2.) reflux, 4 h;	A n/a B 90%

3,4-dichlorobenzyl amine (102-49-8) → 3,4-dichloro-benzonitrile (6574-99-8)

Conditions	Yield
With potassium hydroxide; nickel copper formate; (Bu4N)2S2O8 In 1,2-dichloro-ethane at 20℃; for 13h; Oxidation;	90%
With ammonium hydroxide; oxygen In tert-Amyl alcohol at 110℃; under 2250.23 Torr; for 15h; Autoclave; Green chemistry;	96 %Chromat.
With ammonium hydroxide; oxygen In tert-Amyl alcohol at 110℃; under 1500.15 Torr; Autoclave; Green chemistry;	96 %Chromat.
With ammonia; oxygen; silica gel; 11-pyridino[3,2-h]quinoxalino[2,3-f]quinolin-11-ylpyridino[3,2-h]quinoxalino[2,3-f]quinoline In tert-Amyl alcohol; N,N-dimethyl-formamide at 120 - 800℃; under 1500.15 Torr; for 16h; Sonication; Inert atmosphere; Calcination;	62.74 %Chromat.

3,4-dichlorobenzaldehyde (6287-38-3) → 3,4-dichloro-benzonitrile (6574-99-8)

Conditions	Yield
With phthalic anhydride; hydroxylamine hydrochloride; triethylamine for 0.05h; Reduction; Irradiation;	90%
With aluminum oxide; hydroxylamine hydrochloride; di(n-butyl)tin oxide for 0.0833333h; microwave irradiation;	90%
With acetic acid; hydroxylamine-O-sulfonic acid In water at 50℃; for 6h;	89%

3,4-dichlorobenzyl alcohol (1805-32-9) → 3,4-dichloro-benzonitrile (6574-99-8)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; TEMPOL; ammonia; copper(l) chloride In water; acetonitrile at 20℃; for 24h;	75%

3,4-Dichlorotoluene (95-75-0) → 3,4-dichloro-benzonitrile (6574-99-8)

Conditions	Yield
With bismuth(III) vanadate; ammonia at 440℃; under 760.051 Torr; Catalytic behavior; Temperature;	73.1%
With ammonia at 380℃; Reagent/catalyst; Flow reactor;	72.5%
With vanadyl pyrophosphate; ammonia; water; oxygen at 414.84℃;	55%
With ammonia; oxygen; DC-108 at 425℃; Yield given;

1-(3,4-dichlorophenyl)-2-methylpropan-1-one O-acetyl oxime → 3,4-dichloro-benzonitrile (6574-99-8)

Conditions	Yield
With copper(l) iodide In dimethyl sulfoxide at 90℃; for 12h;	73%

benzenesulfonamide (98-10-2) + 3,4-dichlorbenzoic acid (51-44-5) → 3,4-dichloro-benzonitrile (6574-99-8) + 3,4-dichlorobenzenecarboximidamide (25412-64-0)

Conditions	Yield
With ammonia at 260℃;

m,p-dichloroaniline (95-76-1) → 3,4-dichloro-benzonitrile (6574-99-8)

Conditions	Yield
With hydrogenchloride; sodium nitrite Eintragen der erhaltenen Diazonium-Salz-Loesung in eine aus Kaliumcyanid und Kupfer(II)-sulfat in Wasser bereitete Loesung bei 60-70grad;

3,4-dichlorbenzoic acid (51-44-5) → 3,4-dichloro-benzonitrile (6574-99-8)

Conditions	Yield
With ammonium hydroxide; thionyl chloride 2.) dioxane, 3.) reflux; Multistep reaction;

3,4-dichlorobenzaldehyde (6287-38-3) + (S)-(Fmoc-amino)-(4-fluoro-phenyl)-acetic acid on Wang resin → 3,4-dichloro-benzonitrile (6574-99-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: (NH2OH)2*H2SO4; sodium acetate / ethanol / Heating 2: SOCl2 / benzene / Heating View Scheme

3,4-dichlorobenzoyl chloride (3024-72-4) → 3,4-dichloro-benzonitrile (6574-99-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 25percent aq. NH3 / H2O / 2 h / Ambient temperature 2: 93 percent / thionyl chloride / chlorobenzene / 15 h / Heating View Scheme

4-Cyanochlorobenzene (623-03-0) → 3,4-dichloro-benzonitrile (6574-99-8)

Conditions	Yield
With iron(III) chloride; chlorine; zirconium(IV) chloride; pyrographite; nickel dichloride In water at 200 - 245℃; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere;

1,2-dichloro-benzene (95-50-1) + potassium hexacyanoferrate(III) → 3,4-dichloro-benzonitrile (6574-99-8) + 2,3-dichlorobenzonitrile (6574-97-6)

Conditions	Yield
With 2,3-diethynylquinoxaline; (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid; palladium diacetate; potassium trifluoroacetate; silver carbonate at 80℃; for 24h; Inert atmosphere; Sealed tube; Overall yield = 69 %; Overall yield = 59.3 mg;

3,4-dichloro-benzonitrile (6574-99-8) + methyl 2-diazo-2-(fluorosulfonyl)acetate → 2-(3,4-dichlorophenyl)-5-methoxyoxazole-4-sulfonyl fluoride

Conditions	Yield
Stage #1: 3,4-dichloro-benzonitrile With dirhodium tetraacetate In chloroform at 70℃; Stage #2: methyl 2-diazo-2-(fluorosulfonyl)acetate In chloroform at 70℃; for 12h;	98%

3,4-dichloro-benzonitrile (6574-99-8) → 5-(3,4-dichlorophenyl)-1H-tetrazole

Conditions	Yield
Stage #1: 3,4-dichloro-benzonitrile With sodium azide; tris(pentafluorophenyl)borate In N,N-dimethyl-formamide at 120℃; for 6h; Stage #2: With hydrogenchloride In water; ethyl acetate; N,N-dimethyl-formamide for 0.25h;	96%

3,4-dichloro-benzonitrile (6574-99-8) + N-phenylbenzamidine (1527-91-9) → 3-(3,4-dichlorophenyl)-1,5-diphenyl-1H-1,2,4-triazole

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; zinc(II) iodide In chlorobenzene at 130℃; for 36h; Sealed tube;	96%
With copper(l) iodide; 1,10-Phenanthroline; zinc(II) iodide In chlorobenzene at 130℃; for 36h;	22.6 mg

3,4-dichloro-benzonitrile (6574-99-8) → 3,4-dichlorobenzyl amine (102-49-8)

Conditions	Yield
With sodium tetrahydroborate In water at 95℃; for 1h; chemoselective reaction;	96%

3,4-dichloro-benzonitrile (6574-99-8) + n-butylmagnesium halide → 1-(3,4-dichloro-phenyl)-pentan-1-one (68120-72-9)

Conditions	Yield
In toluene at -25℃; for 2h;	95%

3,4-dichloro-benzonitrile (6574-99-8) → 3,4-Difluorobenzonitrile (64248-62-0)

Conditions	Yield
Stage #1: 3,4-dichloro-benzonitrile With 1,3-dimethylimidazolidin-2-ylidene In water; toluene at 90 - 120℃; Large scale; Stage #2: With potassium fluoride In water; toluene at 130 - 150℃; Large scale;	93%
With potassium fluoride; C6H10BNO4 In N,N-dimethyl-formamide at 110℃; for 11h; Solvent; Temperature;	91%
With potassium fluoride; N,N-bis(1,3-dimethyl-2-imidazolidinyl)ammonium chloride; sodium dodecyl-sulfate; sodium thiosulfate In 1-methyl-pyrrolidin-2-one; toluene at 200 - 210℃; for 4h; Reagent/catalyst; Temperature; Solvent;	90.7%
With potassium fluoride In various solvent(s) at 290℃; under 3677.5 Torr; for 4h;	64%

(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%

3,4-dichloro-benzonitrile (6574-99-8) + benzyl alcohol (100-51-6) → N-benzyl-3,4-dichlorobenzamide (28394-01-6)

Conditions	Yield
Stage #1: 3,4-dichloro-benzonitrile With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; butyraldehyde oxime In toluene at 100℃; for 6h; Schlenk technique; Green chemistry; Stage #2: benzyl alcohol With caesium carbonate In toluene at 130℃; for 12h; Schlenk technique; Green chemistry;	90%

3,4-dichloro-benzonitrile (6574-99-8) → 3,4-dichlorobenzothioamide (22179-73-3)

Conditions	Yield
With sodium hydrogen sulfide; magnesium chloride In N,N-dimethyl-formamide at 40℃;	89%
With pyridine; diammonium sulfide; triethylamine In water at 50℃;	83%

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;

3,4-dichloro-benzonitrile (6574-99-8) + 1-propylmagnesium chloride (2234-82-4) → 1-(3,4-dichlorophenyl)butan-1-one (6582-45-2)

Conditions	Yield
Stage #1: 3,4-dichloro-benzonitrile; 1-propylmagnesium chloride In tetrahydrofuran; diethyl ether at 0 - 20℃; Inert atmosphere; Stage #2: With hydrogenchloride; water In tetrahydrofuran; diethyl ether at 0 - 20℃;	83%
Stage #1: 3,4-dichloro-benzonitrile; 1-propylmagnesium chloride In toluene Stage #2: With sulfuric acid In toluene

3,4-dichloro-benzonitrile (6574-99-8) → (3,4-dichlorophenyl)methylammonium chloride (49552-34-3)

Conditions	Yield
Stage #1: 3,4-dichloro-benzonitrile With MnBr(CO)2[NH(CH2CH2P(iPr)2)2]; hydrogen; sodium t-butanolate In toluene at 120℃; under 37503.8 Torr; for 24h; Autoclave; Stage #2: With hydrogenchloride In diethyl ether	83%

3,4-dichloro-benzonitrile (6574-99-8) + benzenesufonyl hydrazide (80-17-1) → 3,4-dichlorobenzophenone (6284-79-3)

Conditions	Yield
With 2,2'-biquinoline; water; palladium diacetate In dimethyl sulfoxide at 80℃; under 760.051 Torr; for 6h;	83%

3,4-dichloro-benzonitrile (6574-99-8) → 3,4-dichloro-N-hydroxybenzenecarboximidamide (22276-16-0)

Conditions	Yield
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water at 70℃; for 8h;	80.4%
With sodium hydroxide; hydroxylamine hydrochloride In ethanol at 20℃; for 0.333333h;	45%
With hydroxylamine hydrochloride In ethanol	276 mg (45%)
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water at 20℃;
With hydroxylamine hydrochloride; sodium hydrogencarbonate In ethanol; water at 20℃;

3,4-dichloro-benzonitrile (6574-99-8) + butyl magnesium bromide (693-04-9) → 1-(3,4-dichloro-phenyl)-pentan-1-one (68120-72-9)

Conditions	Yield
Stage #1: 3,4-dichloro-benzonitrile; butyl magnesium bromide In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: With hydrogenchloride; water In tetrahydrofuran at 0 - 20℃;	80%
Stage #1: 3,4-dichloro-benzonitrile; butyl magnesium bromide In toluene Stage #2: With sulfuric acid In toluene
Stage #1: 3,4-dichloro-benzonitrile; butyl magnesium bromide In toluene at 20℃; for 2h; Grignard Reaction; Stage #2: With sulfuric acid; water at 0 - 20℃;

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.

3,4-dichloro-benzonitrile (6574-99-8) → 3,4-dichlorobenzamide (2670-38-4)

Conditions	Yield
With sodium perborate In 1,4-dioxane; water at 89℃; for 1h;	77%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; valeraldoxime In toluene at 100℃; for 6h; Inert atmosphere; Schlenk technique;
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold bis(trifluoromethanesulfonyl)imidate; water In tetrahydrofuran at 130℃; for 12h;
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold bis(trifluoromethanesulfonyl)imidate; water In tetrahydrofuran at 130℃; for 12h; Schlenk technique;

3,4-dichloro-benzonitrile (6574-99-8) + 4-methoxy-phenol (150-76-5) → 3-chloro-4-(4-methoxyphenoxy)benzonitrile

Conditions	Yield
With potassium fluoride on basic alumina; 18-crown-6 ether In dimethyl sulfoxide at 140℃; for 16h;	72%

3,4-dichloro-benzonitrile (6574-99-8) → 3,4-dichlorobenzenecarboximidamide (25412-64-0)

Conditions	Yield
Stage #1: 3,4-dichloro-benzonitrile With hydrogenchloride In ethanol; chloroform at 20℃; Cooling; Stage #2: With ammonium carbonate In ethanol at 20℃;	68%
With lithium hexamethyldisilazane

2,2,2-trifluoroethanol (75-89-8) + 3,4-dichloro-benzonitrile (6574-99-8) → 3-chloro-4-2',2',2'-trifluoroethoxybenzonitrile (93624-58-9)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 150℃; for 15h;	63%

Upstream product

• 98-10-2 benzenesulfonamide 
• 51-44-5 3,4-dichlorbenzoic acid 
• 95-76-1 m,p-dichloroaniline 
• 21719-62-0 3.4-Dichlorbenzaldehyd-phenylhydrazon 
• 2670-38-4 3,4-dichlorobenzamide 
• 95-75-0 3,4-Dichlorotoluene 
• 102-49-8 3,4-dichlorobenzyl amine 
• 6287-38-3 3,4-dichlorobenzaldehyde 
• 5331-92-0 3,4-dichlorobenzaldehyde oxime 
• 3024-72-4 3,4-dichlorobenzoyl chloride 
• 623-03-0 4-Cyanochlorobenzene 
• 1805-32-9 3,4-dichlorobenzyl alcohol 
• 18282-59-2 4-bromo-1,2-dichlorobenzene 
• 544-92-3 copper(I) cyanide 

Downstream Products

• 51-44-5 3,4-dichlorbenzoic acid 
• 20925-53-5 3-chloro-4-morpholin-4-yl-benzonitrile 
• 96994-72-8 3-chloro-4-(N,N-dimethylamino)benzonitrile 
• 4278-03-9 3,4-dichloro-benzimidic acid ethyl ester hydrochloride salt 
• 93624-58-9 3-chloro-4-2',2',2'-trifluoroethoxybenzonitrile 
• 132236-05-6 3,4-dichloro-N-(1,10-phenanthrolin-2-yl)benzamidine 
• 64248-62-0 3,4-Difluorobenzonitrile 
• 117482-84-5 3-chloro-4-fluorobenzonitrile 
• 2670-38-4 3,4-dichlorobenzamide 
• 118112-06-4 VUF 8471 
• 6582-42-9 1-(3,4-dichlorophenyl)propan-1-one 
• 22276-16-0 (Z)-3,4-dichloro-N'-hydroxybenzimidamide 
• 22276-16-0 3,4-dichloro-N-hydroxybenzenecarboximidamide 
• 41421-27-6 5-(3,4-dichloro-phenyl)-1⁽²⁾H-tetrazole 

Relevant articles and documents

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