4-Chloro-3-nitrobenzonitrile supplier

Name
4-CHLORO-3-NITROBENZONITRILE
EINECS 213-364-2
CAS No. 939-80-0
Article Data30
CAS DataBase
Density 1.479 g/cm³
Solubility Slightly soluble in water
Melting Point 98-100 °C(lit.)
Formula C₇H₃ClN₂O₂
Boiling Point 284.758 °C at 760 mmHg
Molecular Weight 182.566
Flash Point 126.017 °C
Transport Information
Appearance light yellow crystalline powder
Safety 26-36
Risk Codes 36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xi,Xn
Synonyms 2-Chloro-5-cyanonitrobenzene;3-Nitro-4-chlorobenzonitrile;4-Cyano-2-nitro-1-chlorobenzene;
PSA 69.61000
LogP 2.64308

Synthetic route

: 623-03-0
4-Cyanochlorobenzene

: 939-80-0
4-chloro-3-nitrobenzonitrile

Conditions

Conditions	Yield
With sulfuric acid; nitric acid In methanol Solvent; Large scale;	95%
With sulfuric acid; potassium nitrate at 3 - 5℃; for 3h;	88%
With nitronium tetrafluoborate In acetonitrile at 0 - 20℃; for 20h;	75.47%

: 16588-06-0
4-chloro-3-nitrobenzamide

: 939-80-0
4-chloro-3-nitrobenzonitrile

Conditions

Conditions	Yield
With trimethylsilyl methanesulfonate; phosphorus pentoxide at 70 - 75℃; for 3h; further reagents;	87%
With trichlorophosphate at 170℃;
With Hexamethyldisiloxane; phosphorus pentoxide In chloroform for 2h; Inert atmosphere; Reflux;

: 59670-78-9
4-chloro-3-nitro-benzaldehyde phenylhydrazone

A: 939-80-0
4-chloro-3-nitrobenzonitrile

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

Conditions

Conditions	Yield
With dichloromethylenedimethyliminium chloride In 1,2-dichloro-ethane 1.) room temp., 1 h, 2.) reflux, 4 h;	A 87% B n/a

: 16588-34-4
4-chloro-3-nitro-benzaldehyde

: 939-80-0
4-chloro-3-nitrobenzonitrile

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; ammonium acetate for 0.05h; Microwave irradiation; Neat (no solvent);	81%

: potassiumhexacyanoferrate(II) trihydrate

: 89-61-2
2,5-dichloronitrobenzene

: 939-80-0
4-chloro-3-nitrobenzonitrile

Conditions

Conditions	Yield
With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 18h;	74%

: 16588-24-2
4-bromo-1-chloro-2-nitrobenzene

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

: 939-80-0
4-chloro-3-nitrobenzonitrile

Conditions

Conditions	Yield
With 1,3,5-trichloro-2,4,6-triazine; palladium on activated charcoal; potassium carbonate; triphenylphosphine at 25 - 130℃; for 12.1667h;	74%

: 79-24-3
Nitroethane

: 16588-34-4
4-chloro-3-nitro-benzaldehyde

A: 939-80-0
4-chloro-3-nitrobenzonitrile

B: 66399-01-7
2-chloro-5-hydroxyiminomethylnitrobenzene

C: 134538-49-1
1-chloro-2-nitro-4-((E)-2-nitro-propenyl)-benzene

Conditions

Conditions	Yield
With ammonium acetate In acetic acid under 760 Torr; for 2h; Heating;	A n/a B n/a C 56%

...Expand

: 635-22-3
4-Chloro-3-nitroaniline

: 939-80-0
4-chloro-3-nitrobenzonitrile

Conditions

Conditions	Yield
durch Austausch von NH2 gegen CN nach Sandmeyer;

: 3272-08-0
4-hydroxy-3-nitrobenzonitrile

: 98-59-9
p-toluenesulfonyl chloride

: 91-66-7
N,N-diethylaniline

A: 939-80-0
4-chloro-3-nitrobenzonitrile

B: 3-nitro-4-(toluene-4-sulfonyloxy)-benzonitrile

...Expand

: 623-03-0
4-Cyanochlorobenzene

: 7697-37-2
nitric acid

: 939-80-0
4-chloro-3-nitrobenzonitrile

Conditions

Conditions	Yield
at 5℃;

: 38818-50-7
4-chloro-3-nitro-benzoyl chloride

: 939-80-0
4-chloro-3-nitrobenzonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrachloromethane; aqueous ammonia 2: phosphorus oxychloride / 170 °C View Scheme
Multi-step reaction with 2 steps 1: ammonia / dichloromethane; chloroform; methanol / cooling with ice 2: Hexamethyldisiloxane; phosphorus pentoxide / chloroform / 2 h / Inert atmosphere; Reflux View Scheme

: 96-99-1
4-chloro-3-nitrobenzoate

: 939-80-0
4-chloro-3-nitrobenzonitrile

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: oxalyl dichloride / N,N-dimethyl-formamide / Dichlorofluoromethane / 2 h / 20 °C 2: ammonia / dichloromethane; chloroform; methanol / cooling with ice 3: Hexamethyldisiloxane; phosphorus pentoxide / chloroform / 2 h / Inert atmosphere; Reflux View Scheme

: 104-88-1
4-chlorobenzaldehyde

: 939-80-0
4-chloro-3-nitrobenzonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium acetate / formic acid / 1 h / Reflux 2: sulfuric acid; potassium nitrate / water / 3 h / 0 - 5 °C View Scheme

: potassiumhexacyanoferrate(II) trihydrate

: 4-chloro-3-nitrophenyl-1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate

: 939-80-0
4-chloro-3-nitrobenzonitrile

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In N,N-dimethyl-formamide at 40℃; for 3h; Sealed tube; Green chemistry;

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 108-91-8
cyclohexylamine

: 28096-55-1
4-Cyclohexylamino-3-nitrobenzonitrile

Conditions

Conditions	Yield
In DMF (N,N-dimethyl-formamide) Heating / reflux;	100%
With N,N-dimethyl-formamide Heating;	93.2%
Heating;
In N,N-dimethyl-formamide
In N,N-dimethyl-formamide at 100℃;

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 96898-75-8
4-chloro-N'-hydroxy-3-nitrobenzenecarboximideamide

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; triethylamine In ethanol at 20℃; Heating / reflux;	100%

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 5680-79-5
glycine ethyl ester hydrochloride

: 186666-78-4
3-oxo-1 ,2,3,4-tetrahydroquinoxaline-6-carbonitrile

Conditions

Conditions	Yield
With sodium hydrogencarbonate In methanol; Pd on carbon; ethanol; ethyl acetate	100%

: 110-86-1
pyridine

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 1-(4-cyano-2-nitrophenyl)pyridinium chloride

Conditions

Conditions	Yield
at 90℃; for 1h;	99%
at 90℃;

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 591-35-5
3,5-dichlorophenol

: 261761-44-8
5-cyano-2-(3,5-dichlorophenoxy)nitrobenzene

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran for 1h; Heating / reflux;	98.4%

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 107-15-3
ethylenediamine

: 125901-97-5
4-(2-Amino-ethylamino)-3-nitro-benzonitrile

Conditions

Conditions	Yield
With triethylamine In dimethyl sulfoxide for 30h; Ambient temperature;	98%

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 98-80-6
phenylboronic acid

: 166263-24-7
2-nitro-(1,1'-biphenyl)-4-carbonitrile

Conditions

Conditions	Yield
With caesium carbonate; [PdCl(NNCNHC-nBu)]BF4 In water; N,N-dimethyl-formamide at 120℃; for 1h; Suzuki-Miyaura reaction;	98%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 19h; Suzuki-Miyaura cross coupling; Heating;	92%
With 1-methyl-pyrrolidin-2-one; cesium fluoride; bis(triphenylphosphine)palladium(II) dichloride	79%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate monohydrate; tris-(dibenzylideneacetone)dipalladium(0) In water; toluene Reflux;	72.2%

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 819-46-5
4,4,4-trifluorobutan-1-amine

: 1243325-58-7
3-nitro-4-(4,4,4-trifluorobutylamino)benzonitrile

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 16h; Product distribution / selectivity;	98%
With triethylamine In acetonitrile at 20℃; for 21h; Inert atmosphere;	92%

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 1160502-30-6
4-iodo-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine

: 1260539-62-5
4-{4-iodo-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-3-nitrobenzonitrile

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile at 70℃; for 4h;	98%

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 4-(aminomethyl)benzonitrile hydrochloride

: 4-(N-4-cyanobenzylamino)-3-nitro-benzonitrile

Conditions

Conditions	Yield
With potassium carbonate In 1,4-dioxane for 24h; Reflux; Inert atmosphere;	98%

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 53312-79-1
3-amino-4-chloro-benzonitrile

Conditions

Conditions	Yield
With sodium hydrogen sulfide In tetrahydrofuran; water at 45℃;	97%
With ethanol; iron; calcium chloride In water at 60℃; for 0.5h; chemoselective reaction;	90%
	84%

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 105-53-3
diethyl malonate

: diethyl (4-cyano-2-nitrophenyl)malonate

Conditions

Conditions	Yield
With hydrogenchloride In N,N-dimethyl-formamide; mineral oil	97%

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 19005-63-1
4-(dimethylamino)-3-nitrobenzonitrile

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-formamide With ammonia In water at 240℃; for 0.666667h; Stage #2: 4-chloro-3-nitrobenzonitrile In water for 0.333333h;	97%
for 14h; Reflux;	83%

: 107-10-8
propylamine

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 438554-06-4
3-nitro-4-propylaminobenzonitrile

Conditions

Conditions	Yield
With N,N-dimethyl-formamide Heating;	96.4%
With ethanol
Heating;

: 26510-52-1
ethyl 2-pyridylcarbonylacetate

: 939-80-0
4-chloro-3-nitrobenzonitrile

: (4-cyano-2-nitro-phenyl)-acetic acid ethyl ester

Conditions

Conditions	Yield
Stage #1: ethyl 2-pyridylcarbonylacetate With potassium tert-butylate In 1,4-dioxane; 1-methyl-pyrrolidin-2-one at 20 - 70℃; Stage #2: 4-chloro-3-nitrobenzonitrile In 1,4-dioxane; 1-methyl-pyrrolidin-2-one at 70℃; Stage #3: With hydrogenchloride	96%

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 701-34-8
4-bromo-benzenesulfonic acid amide

: 4-bromo-N-(4-cyano-2-nitrophenyl)benzenesulfonamide

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 140℃; for 0.2h; Microwave irradiation;	96%

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 27489-62-9
trans-4-hydroxycyclohexylamine

: 926569-03-1
4-(((1R,4R)-4-hydroxycyclohexyl)amino)-3-nitrobenzonitrile

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 70℃; Inert atmosphere;	96%

: 26510-52-1
ethyl 2-pyridylcarbonylacetate

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 698392-52-8
2-(4-cyano-2-nitro-phenyl)-3-oxo-3-pyridin-2-yl-propionic acid ethyl ester

Conditions

Conditions	Yield
Stage #1: ethyl 2-pyridylcarbonylacetate With potassium tert-butylate In 1,4-dioxane; 1-methyl-pyrrolidin-2-one at 20 - 70℃; Stage #2: 4-chloro-3-nitrobenzonitrile In 1,4-dioxane; 1-methyl-pyrrolidin-2-one at 70℃; Stage #3: With hydrogenchloride In 1,4-dioxane	95%

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 4001-61-0
2,5-dimethylthiophenol

: 1252681-55-2
4-(2,5-dimethylphenylthio)-3-nitrobenzonitrile

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran for 16h; Reflux;	95%

: 107-85-7
1-amino-3-methylbutane

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 406945-12-8
4-(isopentylamino)-3-nitrobenzonitrile

Conditions

Conditions	Yield
With N,N-dimethyl-formamide Heating;	94.3%
In N,N-dimethyl-formamide	21.0 g (90%)
In N-ethyl-N,N-diisopropylamine at 90℃; for 15h;

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 75-31-0
isopropylamine

: 355022-17-2
4-(isopropylamino)-3-nitrobenzonitrile

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 35℃; for 1h;	94%
With N,N-dimethyl-formamide Heating;	93.8%

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 60933-65-5
(R)-S-methyl-S-phenylsulfoximine

: C14H11N3O3S

Conditions

Conditions	Yield
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate In toluene at 135℃; for 3h; microwave irradiation;	94%

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 112-55-0
1-dodecylthiol

: 202190-87-2
4-(n-dodecylthio)-3-nitrobenzonitrile

Conditions

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium carbonate; sodium L-ascorbate; L-proline In water; dimethyl sulfoxide at 70℃; for 12h;	94%

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 89-97-4
2-CHLOROBENZYLAMINE

: 3-nitro-4-{[(2-chlorophenyl)methyl]amino}benzonitrile

Conditions

Conditions	Yield
In methanol for 7h; Reflux;	94%

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 109-73-9
N-butylamine

: 143193-44-6
4-butylamino-3-nitrobenzonitrile

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 2h; Heating;	93%
With N,N-dimethyl-formamide Heating;	92.7%
With ethanol
In ethanol Reflux;

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 3124-37-6
carbamic acid 2-trimethylsilylethyl ester

: 1257310-73-8
(4-cyano-2-nitrophenyl)carbamic acid 2-trimethylsilanylethyl ester

Conditions

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 120℃; for 15h; Inert atmosphere;	93%

: 38041-19-9
4-aminotetrahydropyran

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 320406-00-6
3-nitro-4-(tetrahydropyran-4-ylamino)benzonitrile

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 70℃;	93%

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 4403-69-4
2-amino-1-benzylamine

: C14H10ClN3O2

Conditions

Conditions	Yield
With copper(II) cinnamic acid complex In toluene at 110℃; Green chemistry;	92%

: 939-80-0
4-chloro-3-nitrobenzonitrile

: 141-43-5
ethanolamine

: 90349-40-9
4-(2'-hydroxyethyl)amino-3-nitrobenzonitrile

Conditions

Conditions	Yield
With N,N-dimethyl-formamide Heating;	91%
With ethanol
In tetrahydrofuran; ethanol

4-Chloro-3-nitrobenzonitrile Specification

The Benzonitrile,4-chloro-3-nitro- with the CAS number 939-80-0 is also called 2-Chloro-5-cyanonitrobenzene. Both the systematic name and IUPAC name are 4-chloro-3-nitrobenzonitrile. Its molecular formula is C₇H₃ClN₂O₂. The EINECS registry number is 213-364-2. This chemical belongs to the following product categories: (1)Aromatic Nitriles; (2)C6 to C7; (3)Cyanides/Nitriles; (4)Nitrogen Compounds.

The properties of the Benzonitrile,4-chloro-3-nitro- are: (1)ACD/LogP: 1.87; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.867; (4)ACD/LogD (pH 7.4): 1.867; (5)ACD/BCF (pH 5.5): 15.441; (6)ACD/BCF (pH 7.4): 15.441; (7)ACD/KOC (pH 5.5): 246.871; (8)ACD/KOC (pH 7.4): 246.871; (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: 42.181 cm³; (15)Molar Volume: 123.412 cm³; (16)Polarizability: 16.722×10^-24cm³; (17)Surface Tension: 62.662 dyne/cm; (18)Enthalpy of Vaporization: 52.376 kJ/mol; (19)Vapour Pressure: 0.003 mmHg at 25°C.

Preparation: This chemical can be prepared by 4-chloro-benzonitrile. This reaction needs reagent nitric acid at temperature of 0 °C.

Uses: This chemical can react with butylamine to prepare 4-butylamino-3-nitro-benzonitrile. This reaction needs reagent ethanol.

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 wear suitable protective clothing. Then 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: c1cc(c(cc1C#N)[N+](=O)[O-])Cl
(2)InChI: InChI=1/C7H3ClN2O2/c8-6-2-1-5(4-9)3-7(6)10(11)12/h1-3H
(3)InChIKey: XBLPHYSLHRGMNW-UHFFFAOYAQ

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD50	oral	2050mg/kg (2050mg/kg)		"Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 909, 1986.

Product Name

4-CHLORO-3-NITROBENZONITRILE

Synthetic route

4-Chloro-3-nitrobenzonitrile Specification

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