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939-80-0

Basic Information
CAS No.: 939-80-0
Name: 4-CHLORO-3-NITROBENZONITRILE
Article Data: 30
Molecular Structure:
Molecular Structure of 939-80-0 (4-CHLORO-3-NITROBENZONITRILE)
Formula: C7H3ClN2O2
Molecular Weight: 182.566
Synonyms: 2-Chloro-5-cyanonitrobenzene;3-Nitro-4-chlorobenzonitrile;4-Cyano-2-nitro-1-chlorobenzene;
EINECS: 213-364-2
Density: 1.479 g/cm3
Melting Point: 98-100 °C(lit.)
Boiling Point: 284.758 °C at 760 mmHg
Flash Point: 126.017 °C
Solubility: Slightly soluble in water
Appearance: light yellow crystalline powder
Hazard Symbols: IrritantXi,HarmfulXn
Risk Codes: 36/37/38-20/21/22
Safety: 26-36
PSA: 69.61000
LogP: 2.64308
Synthetic route
623-03-0

4-Cyanochlorobenzene

939-80-0

4-chloro-3-nitrobenzonitrile

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 18h;74%
16588-24-2

4-bromo-1-chloro-2-nitrobenzene

939-80-0

4-chloro-3-nitrobenzonitrile

Conditions
ConditionsYield
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
ConditionsYield
With ammonium acetate In acetic acid under 760 Torr; for 2h; Heating;A n/a
B n/a
C 56%
635-22-3

4-Chloro-3-nitroaniline

939-80-0

4-chloro-3-nitrobenzonitrile

Conditions
ConditionsYield
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

623-03-0

4-Cyanochlorobenzene

7697-37-2

nitric acid

939-80-0

4-chloro-3-nitrobenzonitrile

Conditions
ConditionsYield
at 5℃;
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  • CAS No.939-80-0	4-CHLORO-3-NITROBENZONITRILE

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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.