28163-00-0

Basic information

• Product Name: 2-Chloro-4-nitrobenzonitrile
• Synonyms: 2-CHLORO-4-NITROBENZONITRILE;3-Chloro-4-cyanonitrobenzene;2-CHLORO-4-NITROBENZONITRIL;2-chloro-4-nitrobenzenecarbonitrile;2-Chloro-4-nitrobenzonitrile,98%;4-nitro-2-chlorobenzonitrile
• CAS NO: 28163-00-0
• Molecular Formula: C₇H₃ClN₂O₂
• Molecular Weight: 182.56
• Product Categories: Aromatic Nitriles
• Mol File: 28163-00-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 83-84 °C
• Boiling Point: 337 °C at 760 mmHg
• Flash Point: 157.6 °C
• Appearance: beige powder
• Density: 1.6133 (rough estimate)
• Vapor Pressure: 0.000108mmHg at 25°C
• Refractive Index: 1.5557 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• CAS DataBase Reference: 2-Chloro-4-nitrobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4-nitrobenzonitrile(28163-00-0)
• EPA Substance Registry System: 2-Chloro-4-nitrobenzonitrile(28163-00-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/21/22
• Safety Statements: 36/37/39-26-22-36
• RIDADR: 3276
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 28163-00-0(Hazardous Substances Data)

Usage

Chemical Properties

beige powder

InChI:InChI=1/C7H3ClN2O2/c8-7-3-6(10(11)12)2-1-5(7)4-9/h1-3H

Synthetic route

2-chloro-4-nitro-benzaldehyde phenylhydrazone (98606-58-7) → 4-nitro-2-chlorobenzonitrile (28163-00-0) + N,N-dimethyl-N'-phenylcarbamimidic chloride (7684-30-2)

Conditions	Yield
With dichloromethylenedimethyliminium chloride In 1,2-dichloro-ethane 1.) room temp., 1 h, 2.) reflux, 4 h;	A 89% B n/a

Novastat (3011-89-0) → 4-nitro-2-chlorobenzonitrile (28163-00-0)

Conditions	Yield
With trimethylsilylphosphate for 0.416667h; Heating;	88%
With thionyl chloride In benzene	79%
Multi-step reaction with 3 steps 1: CCl4; PCl5 2: formic acid; benzene 3: 100 - 105 °C View Scheme
With phosphorus pentachloride In tetrachloromethane

(2-chloro-4-nitrophenyl)methanol (52301-88-9) → 4-nitro-2-chlorobenzonitrile (28163-00-0)

Conditions	Yield
With ammonium hydroxide; trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane; ammonium bromide at 20℃; for 1.66667h; Green chemistry;	86%

(2-chloro-4-nitrophenyl)methanamine → 4-nitro-2-chlorobenzonitrile (28163-00-0)

Conditions	Yield
With ammonium hydroxide; trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane; ammonium bromide at 20℃; for 1.66667h; Green chemistry;	86%

1-(bromomethyl)-2-chloro-4-nitrobenzene (42533-63-1) → 4-nitro-2-chlorobenzonitrile (28163-00-0)

Conditions	Yield
With ammonium hydroxide; trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane; ammonium bromide at 20℃; for 1.5h; Green chemistry;	85%

sodium cyanide (773837-37-9) + Reaxys ID: 23021485 → 4-nitro-2-chlorobenzonitrile (28163-00-0)

Conditions	Yield
With copper(l) cyanide at 20℃;	83%

4-nitrobenzonitrile (619-72-7) → 4-nitro-2-chlorobenzonitrile (28163-00-0)

Conditions	Yield
With N-chloro-succinimide; palladium diacetate; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 70℃; for 12h; Sealed tube;	83%

2-chloro-4-nitrobenzyl chloride (50274-95-8) → 4-nitro-2-chlorobenzonitrile (28163-00-0)

Conditions	Yield
With ammonium hydroxide; trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane; ammonium bromide at 20℃; for 2h; Green chemistry;	80%

2-chloro-4-nitrobenzaldehyde (5568-33-2) → 4-nitro-2-chlorobenzonitrile (28163-00-0)

Conditions	Yield
With ammonium hydroxide; trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane; ammonium bromide at 20℃; for 0.833333h; Green chemistry;	78%

(2-chloro-4-nitro-benzoyl)-amidophosphoryl chloride (856800-39-0) → 4-nitro-2-chlorobenzonitrile (28163-00-0)

Conditions	Yield
at 100 - 105℃;

2-chloro-N-dichlorophosphoryl-4-nitro-benzimidoyl chloride (119211-32-4) → 4-nitro-2-chlorobenzonitrile (28163-00-0)

Conditions	Yield
at 100 - 105℃; Zersetzung;

acetic acid (64-19-7) + 2-Chloro-4-nitroaniline (121-87-9) → 4-nitro-2-chlorobenzonitrile (28163-00-0)

Conditions	Yield
With sulfuric acid; sodium nitrite Eintragen der Reaktionsloesung in eine wss. Loesung von Kalium-tetracyanoniccolat(II) und Natriumcarbonat;

N-tosyl-2-chloroaniline (6380-05-8) → 4-nitro-2-chlorobenzonitrile (28163-00-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: water; acetic acid; nitric acid 2: aqueous sulfuric acid 3: sulfuric acid; sodium nitrite / Eintragen der Reaktionsloesung in eine wss. Loesung von Kalium-tetracyanoniccolat(II) und Natriumcarbonat View Scheme
Multi-step reaction with 3 steps 1: acetic acid; water; nitric acid 2: aqueous sulfuric acid 3: sulfuric acid; sodium nitrite / Eintragen der Reaktionsloesung in eine wss. Loesung von Kalium-tetracyanoniccolat(II) und Natriumcarbonat View Scheme

2-chloro-4-nitro-benzoic acid-(trichlorophosphoranyliden-amide) (100524-03-6) → 4-nitro-2-chlorobenzonitrile (28163-00-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: formic acid; benzene 2: 100 - 105 °C View Scheme

N-(2-chloro-4-nitrophenyl)-4-methylbenzenesulfonamide (7230-61-7) → 4-nitro-2-chlorobenzonitrile (28163-00-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous sulfuric acid 2: sulfuric acid; sodium nitrite / Eintragen der Reaktionsloesung in eine wss. Loesung von Kalium-tetracyanoniccolat(II) und Natriumcarbonat View Scheme

4-nitro-2-chlorobenzonitrile (28163-00-0) → 2-chloro-4-fluorobenzonitrile (60702-69-4)

Conditions	Yield
With tetrabutyl ammonium fluoride In dimethyl sulfoxide at 25℃; for 0.166667h; Inert atmosphere; Microwave irradiation; Anhydrous conditions;	95%

methanol (67-56-1) + 4-nitro-2-chlorobenzonitrile (28163-00-0) → 2-chloro-4-methoxylbenzonitrile (127666-99-3)

Conditions	Yield
With sodium hydroxide	89%

4-nitro-2-chlorobenzonitrile (28163-00-0) + sodium methylate (124-41-4) → 2-methoxy-4-nitrobenzonitrile (101084-96-2)

Conditions	Yield
In methanol for 13h; Reflux;	83%

4-nitro-2-chlorobenzonitrile (28163-00-0) → 4-amino-2-chlorobenzonitrile (20925-27-3)

Conditions	Yield
With hydrazine hydrate In (2S)-N-methyl-1-phenylpropan-2-amine hydrate	78%
With hydrogen In ethanol at 80℃; under 15001.5 Torr; for 3.5h; Catalytic behavior; chemoselective reaction;

4-nitro-2-chlorobenzonitrile (28163-00-0) + sodium 4-methylbenzenesulfinate (824-79-3) → 2,4-bis(toluene-4-sulfonyl)benzonitrile

Conditions	Yield
With {(Pd{Fe(η5-C5H5)(η5-C5H3C(CH3)=NC6H4CH3-4)}(μ-Cl))2}; potassium carbonate In dimethyl sulfoxide at 110℃; for 12h; Inert atmosphere;	76%

4-nitro-2-chlorobenzonitrile (28163-00-0) + phenylacetonitrile (140-29-4) → (3-chloro-4-cyanophenyl)-phenylacetonitrile

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃;	68%

4-nitro-2-chlorobenzonitrile (28163-00-0) → 2-chloro-N'-hydroxy-4-nitrobenzamidine (96898-76-9)

Conditions	Yield
With hydroxylamine hydrochloride; triethylamine In ethanol at 20 - 85℃;	68%

4-nitro-2-chlorobenzonitrile (28163-00-0) + 2-anilineboronic acid pinacol ester (191171-55-8) → 6-amino-9-nitrophenanthridine (1617497-66-1)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane at 75 - 100℃; for 8.08333h; Suzuki-Miyaura Coupling; Inert atmosphere;	45%

4-nitro-2-chlorobenzonitrile (28163-00-0) → 2-chloro-N'-hydroxy-4-nitrobenzene-1-carboximidamide

Conditions	Yield
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water for 6h; Reflux;	16%

piperidine (110-89-4) + 4-nitro-2-chlorobenzonitrile (28163-00-0) → 4-nitro-2-piperidino-benzonitrile

ethanol (64-17-5) + 4-nitro-2-chlorobenzonitrile (28163-00-0) + sodium p-thiocresolate (10486-08-5) → 2-chloro-4-p-tolylsulfanyl-benzonitrile (873378-23-5) + 4-nitro-2-p-tolylsulfanyl-benzonitrile (855290-54-9)

Conditions	Yield
at 40℃;

4-nitro-2-chlorobenzonitrile (28163-00-0) → 2-chloro-4-nitrobenzoic acid (99-60-5)

Conditions	Yield
With sulfuric acid Behandeln des Reaktionsgemisches mit wss. Natriumnitrit-Loesung;

4-nitro-2-chlorobenzonitrile (28163-00-0) + para-thiocresol (106-45-6) → 2-chloro-4-p-tolylsulfanyl-benzonitrile (873378-23-5) + 4-nitro-2-p-tolylsulfanyl-benzonitrile (855290-54-9)

Conditions	Yield
With sodium hydroxide; ethanol

4-nitro-2-chlorobenzonitrile (28163-00-0) → 2,4-difluorobenzonitrile (3939-09-1) + 2-chloro-4-fluorobenzonitrile (60702-69-4)

Conditions	Yield
With potassium fluoride; tetraphenylphosphonium bromide In dimethyl sulfoxide at 130℃; for 1h;	A 10 % Chromat. B 90 % Chromat.

4-nitro-2-chlorobenzonitrile (28163-00-0) → 2-(Cyano-phenyl-methyl)-4-methoxy-benzonitrile (127667-07-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / NaOH 2: 79 percent / potassium tert-butoxide / dimethylformamide / 1 h / 20 °C View Scheme

4-nitro-2-chlorobenzonitrile (28163-00-0) → 4-piperidino-2-(toluene-4-sulfonyl)-benzonitrile

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. NaOH solution; ethanol 2: aqueous hydrogen peroxide; acetic acid View Scheme

4-nitro-2-chlorobenzonitrile (28163-00-0) → 2-piperidino-4-(toluene-4-sulfonyl)-benzonitrile

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. NaOH solution; ethanol 2: hydrogen peroxide; acetic acid View Scheme

Upstream product

• 64-19-7 acetic acid 
• 121-87-9 2-Chloro-4-nitroaniline 
• 3011-89-0 Novastat 
• 98606-58-7 2-chloro-4-nitro-benzaldehyde phenylhydrazone 
• 52301-88-9 (2-chloro-4-nitrophenyl)methanol 
• 50274-95-8 2-chloro-4-nitrobenzyl chloride 
• 42533-63-1 1-(bromomethyl)-2-chloro-4-nitrobenzene 
• 5568-33-2 2-chloro-4-nitrobenzaldehyde 
• 619-72-7 4-nitrobenzonitrile 
• 773837-37-9 sodium cyanide 
• 119211-32-4 2-chloro-N-dichlorophosphoryl-4-nitro-benzimidoyl chloride 
• 856800-39-0 (2-chloro-4-nitro-benzoyl)-amidophosphoryl chloride 
• 7230-61-7 N-(2-chloro-4-nitrophenyl)-4-methylbenzenesulfonamide 
• 100524-03-6 2-chloro-4-nitro-benzoic acid-(trichlorophosphoranyliden-amide) 

Downstream Products

• 873378-23-5 2-chloro-4-p-tolylsulfanyl-benzonitrile 
• 855290-54-9 4-nitro-2-p-tolylsulfanyl-benzonitrile 
• 127666-99-3 2-chloro-4-methoxylbenzonitrile 
• 1006899-23-5 4-amino-2-cyclopropylbenzonitrile 
• 1533425-13-6 2-cyclopropyl-4-isothiocyanatobenzonitrile 
• 1533434-91-1 (Z)-methyl N'-cyano-N-(4-cyano-3-cyclopropylphenyl)carbamimidothioate 
• 1533424-23-5 4-(5-amino-1H-1,2,4-triazol-3-ylamino)-2-cyclopropylbenzonitrile 
• 398487-31-5 4-chloro-7-methoxyquinoline-6-carbonitrile 
• 417716-92-8 lenvatinib 
• 101084-96-2 2-methoxy-4-nitrobenzonitrile 
• 60702-69-4 2-chloro-4-fluorobenzonitrile 
• 96898-76-9 2-chloro-N'-hydroxy-4-nitrobenzamidine 
• 20925-27-3 4-amino-2-chlorobenzonitrile 
• 836610-99-2 4-nitro-2-(toluene-4-sulfonyl)-benzonitrile 

Relevant articles and documents

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