Product Name

  • Name

    2-Chloro-4-nitrobenzonitrile

  • EINECS
  • CAS No. 28163-00-0
  • Article Data11
  • CAS DataBase
  • Density 1.47 g/cm3
  • Solubility
  • Melting Point 83-84 °C
  • Formula C7H3ClN2O2
  • Boiling Point 337 °C at 760 mmHg
  • Molecular Weight 182.566
  • Flash Point 157.6 °C
  • Transport Information UN 3276
  • Appearance beige powder
  • Safety 36/37/39-26-22
  • Risk Codes 36/37/38-20/21/22
  • Molecular Structure Molecular Structure of 28163-00-0 (2-Chloro-4-nitrobenzonitrile)
  • Hazard Symbols HarmfulXn, IrritantXi
  • Synonyms 2-Chlor-4-nitrobenzonitril;
  • PSA 69.61000
  • LogP 2.64308

Synthetic route

2-chloro-4-nitro-benzaldehyde phenylhydrazone
98606-58-7

2-chloro-4-nitro-benzaldehyde phenylhydrazone

A

4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

B

N,N-dimethyl-N'-phenylcarbamimidic chloride
7684-30-2

N,N-dimethyl-N'-phenylcarbamimidic chloride

Conditions
ConditionsYield
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

Novastat

4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

Conditions
ConditionsYield
With trimethylsilylphosphate for 0.416667h; Heating;88%
With thionyl chloride In benzene79%
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

(2-chloro-4-nitrophenyl)methanol

4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

Conditions
ConditionsYield
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

(2-chloro-4-nitrophenyl)methanamine

4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

Conditions
ConditionsYield
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

1-(bromomethyl)-2-chloro-4-nitrobenzene

4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

Conditions
ConditionsYield
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

sodium cyanide

Reaxys ID: 23021485

Reaxys ID: 23021485

4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

Conditions
ConditionsYield
With copper(l) cyanide at 20℃;83%
4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

Conditions
ConditionsYield
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

2-chloro-4-nitrobenzyl chloride

4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

Conditions
ConditionsYield
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

2-chloro-4-nitrobenzaldehyde

4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

Conditions
ConditionsYield
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

(2-chloro-4-nitro-benzoyl)-amidophosphoryl chloride

4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

Conditions
ConditionsYield
at 100 - 105℃;
2-chloro-N-dichlorophosphoryl-4-nitro-benzimidoyl chloride
119211-32-4

2-chloro-N-dichlorophosphoryl-4-nitro-benzimidoyl chloride

4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

Conditions
ConditionsYield
at 100 - 105℃; Zersetzung;
acetic acid
64-19-7

acetic acid

2-Chloro-4-nitroaniline
121-87-9

2-Chloro-4-nitroaniline

4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

Conditions
ConditionsYield
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

N-tosyl-2-chloroaniline

4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

Conditions
ConditionsYield
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

2-chloro-4-nitro-benzoic acid-(trichlorophosphoranyliden-amide)

4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

Conditions
ConditionsYield
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

N-(2-chloro-4-nitrophenyl)-4-methylbenzenesulfonamide

4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

Conditions
ConditionsYield
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

4-nitro-2-chlorobenzonitrile

2-chloro-4-fluorobenzonitrile
60702-69-4

2-chloro-4-fluorobenzonitrile

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In dimethyl sulfoxide at 25℃; for 0.166667h; Inert atmosphere; Microwave irradiation; Anhydrous conditions;95%
methanol
67-56-1

methanol

4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

2-chloro-4-methoxylbenzonitrile
127666-99-3

2-chloro-4-methoxylbenzonitrile

Conditions
ConditionsYield
With sodium hydroxide89%
4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

sodium methylate
124-41-4

sodium methylate

2-methoxy-4-nitrobenzonitrile
101084-96-2

2-methoxy-4-nitrobenzonitrile

Conditions
ConditionsYield
In methanol for 13h; Reflux;83%
4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

4-amino-2-chlorobenzonitrile
20925-27-3

4-amino-2-chlorobenzonitrile

Conditions
ConditionsYield
With hydrazine hydrate In (2S)-N-methyl-1-phenylpropan-2-amine hydrate78%
With hydrogen In ethanol at 80℃; under 15001.5 Torr; for 3.5h; Catalytic behavior; chemoselective reaction;
4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

sodium 4-methylbenzenesulfinate
824-79-3

sodium 4-methylbenzenesulfinate

2,4-bis(toluene-4-sulfonyl)benzonitrile

2,4-bis(toluene-4-sulfonyl)benzonitrile

Conditions
ConditionsYield
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

4-nitro-2-chlorobenzonitrile

phenylacetonitrile
140-29-4

phenylacetonitrile

(3-chloro-4-cyanophenyl)-phenylacetonitrile

(3-chloro-4-cyanophenyl)-phenylacetonitrile

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃;68%
4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

2-chloro-N'-hydroxy-4-nitrobenzamidine
96898-76-9

2-chloro-N'-hydroxy-4-nitrobenzamidine

Conditions
ConditionsYield
With hydroxylamine hydrochloride; triethylamine In ethanol at 20 - 85℃;68%
4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

6-amino-9-nitrophenanthridine
1617497-66-1

6-amino-9-nitrophenanthridine

Conditions
ConditionsYield
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

4-nitro-2-chlorobenzonitrile

2-chloro-N'-hydroxy-4-nitrobenzene-1-carboximidamide

2-chloro-N'-hydroxy-4-nitrobenzene-1-carboximidamide

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water for 6h; Reflux;16%
piperidine
110-89-4

piperidine

4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

4-nitro-2-piperidino-benzonitrile

4-nitro-2-piperidino-benzonitrile

ethanol
64-17-5

ethanol

4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

sodium p-thiocresolate
10486-08-5

sodium p-thiocresolate

A

2-chloro-4-p-tolylsulfanyl-benzonitrile
873378-23-5

2-chloro-4-p-tolylsulfanyl-benzonitrile

B

4-nitro-2-p-tolylsulfanyl-benzonitrile
855290-54-9

4-nitro-2-p-tolylsulfanyl-benzonitrile

Conditions
ConditionsYield
at 40℃;
...Expand
4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

2-chloro-4-nitrobenzoic acid
99-60-5

2-chloro-4-nitrobenzoic acid

Conditions
ConditionsYield
With sulfuric acid Behandeln des Reaktionsgemisches mit wss. Natriumnitrit-Loesung;
4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

para-thiocresol
106-45-6

para-thiocresol

A

2-chloro-4-p-tolylsulfanyl-benzonitrile
873378-23-5

2-chloro-4-p-tolylsulfanyl-benzonitrile

B

4-nitro-2-p-tolylsulfanyl-benzonitrile
855290-54-9

4-nitro-2-p-tolylsulfanyl-benzonitrile

Conditions
ConditionsYield
With sodium hydroxide; ethanol
...Expand
4-nitro-2-chlorobenzonitrile
28163-00-0

4-nitro-2-chlorobenzonitrile

A

2,4-difluorobenzonitrile
3939-09-1

2,4-difluorobenzonitrile

B

2-chloro-4-fluorobenzonitrile
60702-69-4

2-chloro-4-fluorobenzonitrile

Conditions
ConditionsYield
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

4-nitro-2-chlorobenzonitrile

2-(Cyano-phenyl-methyl)-4-methoxy-benzonitrile
127667-07-6

2-(Cyano-phenyl-methyl)-4-methoxy-benzonitrile

Conditions
ConditionsYield
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-nitro-2-chlorobenzonitrile

4-piperidino-2-(toluene-4-sulfonyl)-benzonitrile

4-piperidino-2-(toluene-4-sulfonyl)-benzonitrile

Conditions
ConditionsYield
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

4-nitro-2-chlorobenzonitrile

2-piperidino-4-(toluene-4-sulfonyl)-benzonitrile

2-piperidino-4-(toluene-4-sulfonyl)-benzonitrile

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

2-Chloro-4-nitrobenzonitrile Specification

The Benzonitrile,2-chloro-4-nitro- with the CAS number 28163-00-0 is also called 2-Chlor-4-nitrobenzonitril. Both the systematic name and IUPAC name are 2-chloro-4-nitrobenzonitrile. Its molecular formula is C7H3ClN2O2. The product category is Aromatic Nitriles. This chemical is a kind of organics. It should be stored in dry and cool environment.

The properties of the Benzonitrile,2-chloro-4-nitro- are: (1)ACD/LogP: 1.85; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.85; (4)ACD/LogD (pH 7.4): 1.85; (5)ACD/BCF (pH 5.5): 14.88; (6)ACD/BCF (pH 7.4): 14.88; (7)ACD/KOC (pH 5.5): 240.39; (8)ACD/KOC (pH 7.4): 240.39; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 69.61 Å2; (13)Index of Refraction: 1.599; (14)Molar Refractivity: 42.18 cm3; (15)Molar Volume: 123.4 cm3; (16)Polarizability: 16.72×10-24cm3; (17)Surface Tension: 62.6 dyne/cm; (18)Enthalpy of Vaporization: 58.02 kJ/mol; (19)Vapour Pressure: 0.000108 mmHg at 25°C.

Preparation: This chemical can be prepared by 2-chloro-4-nitro-benzoic acid amide. This reaction needs reagent trimethylsilyl polyphosphate at heating condition. The reaction time is 25 min. The yield is 88%.

Uses: This chemical can react with methanol to prepare 2-chloro-4-methoxy-benzonitrile. This reaction needs reagent NaOH. The yield is 89%.

While using this chemical, you should be very cautious. This chemical is harmful by inhalation, in contact with skin and if swallowed. It is not only irritating to skin, but also irritating to eyes and respiratory system. Therefore, you should take the following instructions. Firstly, you should not breathe dust. Then you should wear suitable protective clothing, gloves and eye/face protection. Finally in case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: N#Cc1ccc(cc1Cl)[N+]([O-])=O
(2)InChI: InChI=1/C7H3ClN2O2/c8-7-3-6(10(11)12)2-1-5(7)4-9/h1-3H
(3)InChIKey: ZIGQFRQZYVQQDR-UHFFFAOYAO

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