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873-32-5

Basic Information
CAS No.: 873-32-5
Name: 2-Chlorobenzonitrile
Article Data: 257
Cas Database
Molecular Structure:
Molecular Structure of 873-32-5 (2-Chlorobenzonitrile)
Formula: C7H4ClN
Molecular Weight: 137.568
Synonyms: Benzonitrile, 2-chloro-;Benzonitrile, o-chloro-;o-Chlorbenzonitril [Czech];o-Cyanochlorobenzene;o-Chlorocyanobenzene;Nitril kyseliny o-chlorbenzoove [Czech];2-Chloro-Benzonitrile;2-chloro benzonitrile;o-chlorotolunitrile;
EINECS: 212-836-5
Density: 1.23 g/cm3
Melting Point: 43-46 °C(lit.)
Boiling Point: 232.8 °C at 760 mmHg
Flash Point: 100.8 °C
Solubility: N/A
Appearance: white to light yellow crystal powder
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 21/22-36-21/22/23
Safety: 23
Transport Information: UN 3439
PSA: 23.79000
LogP: 2.21168
Synthetic route
89-98-5

2-chloro-benzaldehyde

873-32-5

2-Chlorobenzonitrile

Conditions
ConditionsYield
With ammonium hydroxide; sodium persulfate; sodium iodide; iron(II) chloride In 1,2-dichloro-ethane at 20 - 50℃; for 16h;99%
With copper(II) oxide; hydroxylamine hydrochloride In neat (no solvent) for 0.0208333h; Mechanism; Reagent/catalyst; Microwave irradiation; Green chemistry;96%
With ammonium hydroxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In ethanol at 40℃; under 1500.15 - 3000.3 Torr; for 4h;96%
17849-38-6

2-Chlorobenzyl alcohol

873-32-5

2-Chlorobenzonitrile

Conditions
ConditionsYield
Stage #1: 2-Chlorobenzyl alcohol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tert-butylhypochlorite In dichloromethane at 20℃; for 0.5h; Inert atmosphere;
Stage #2: With ammonia; iodine In dichloromethane; water at 20℃; for 2h; Inert atmosphere;
99%
With ammonium hydroxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In ethanol at 40℃; under 1500.15 - 3000.3 Torr; for 4h; Reagent/catalyst;97.1%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ammonia; oxygen; copper(II) nitrate In water; dimethyl sulfoxide at 80℃; under 760.051 Torr; for 7h;95%
15717-17-6

2-chlorothiobenzamide

873-32-5

2-Chlorobenzonitrile

Conditions
ConditionsYield
With polystyrene-bound diaryl telluroxide In dichloromethane for 1h; Ambient temperature;98%
With polystyrne-bound selenoxide In ethanol for 24h; Heating;95%
89-97-4

2-CHLOROBENZYLAMINE

873-32-5

2-Chlorobenzonitrile

Conditions
ConditionsYield
With pyridine; Oxone; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; Pyridine hydrobromide In dichloromethane at 20℃; for 12h; Green chemistry;98%
With C68H64Cl2N6P2Ru2(4+)*2F6P(1-)*2Cl(1-); caesium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; Green chemistry;91.9%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; free radical; trichloroisocyanuric acid In dichloromethane at 10℃; for 2h;90%

2-(dodecylthio)benzonitrile

A

2634-33-5

1,2-benzisothiazolin-3-one

B

873-32-5

2-Chlorobenzonitrile

C

112-52-7

1-chlorododecane

Conditions
ConditionsYield
Stage #1: 2-(dodecylthio)benzonitrile With sulfuryl dichloride; water In chlorobenzene at 20 - 65℃; for 3h;
Stage #2: With sodium hydroxide In water at 60 - 65℃; pH=9 - 10;
Stage #3: With hydrogenchloride In water at 20 - 30℃; pH=3 - 4; Reagent/catalyst;
A 106 g
B 97.2%
C 143 g
3717-28-0

2-chloro benzaldehyde oxime

873-32-5

2-Chlorobenzonitrile

Conditions
ConditionsYield
With N-trifluoroacetylimidazole In tetrahydrofuran for 3.5h; Heating;97%
With cerium(IV) oxide In o-xylene at 160℃; for 0.5h; Dean-Stark; Inert atmosphere;97%
With phosphoric acid diethyl ester 2-phenylbenzimidazol-1-yl ester; triethylamine In acetonitrile at 20℃; for 0.416667h;96%
75-05-8

acetonitrile

118-91-2

ortho-chlorobenzoic acid

873-32-5

2-Chlorobenzonitrile

Conditions
ConditionsYield
at 350℃; under 48754.9 Torr; for 0.416667h; Supercritical conditions; Flow reactor;97%
With molybdenum hexacarbonyl In tetrachloromethane at 150℃; for 6h; Autoclave;28%

C14H10ClNO2

873-32-5

2-Chlorobenzonitrile

Conditions
ConditionsYield
With iron(III) sulfate; 4-nitro-phenol In cyclohexane at 20℃; for 0.116667h;97%
With iron(III) chloride; 2,6-di-tert-butyl-4-methyl-phenol In toluene at 20℃; for 0.116667h; Schlenk technique;86%
609-66-5

2-chlorobenzamide

873-32-5

2-Chlorobenzonitrile

Conditions
ConditionsYield
With trimethylsilyl methanesulfonate; phosphorus pentoxide at 70 - 75℃; for 3h; further reagents;95%
With triethylamine; trifluoroacetyl chloride In dichloromethane93%
With C8H14N2O4S In dichloromethane for 1h; Reflux;93%
17849-38-6

2-Chlorobenzyl alcohol

89-98-5

2-chloro-benzaldehyde

118-91-2

ortho-chlorobenzoic acid

873-32-5

2-Chlorobenzonitrile

Conditions
ConditionsYield
With ammonium hydroxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In ethanol at 40℃; under 1500.15 - 3000.3 Torr; for 4h;95%
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Chemistry

IUPAC Name: 2-Chlorobenzonitrile
Following is the structure of o-chlorotolunitrile (CAS NO.873-32-5):
           
Molecular formula:C7H4ClN
Molecular Weight: 137.57
EINECS: 212-836-5
Index of Refraction: 1.563
Molar Refractivity: 36.14 cm3
Molar Volume: 111.2 cm3
Density: 1.23 g/cm3
Flash Point: 100.8 °C
Melting point: 43-46 °C(lit.)
Polarizability: 14.33 10-24cm3
Surface Tension: 46.2 dyne/cm
Enthalpy of Vaporization: 46.95 kJ/mol
Boiling Point: 232.8 °C at 760 mmHg
Vapour Pressure: 0.0577 mmHg at 25 °C
Appearance of o-chlorotolunitrile (CAS NO.873-32-5): white to light yellow crystal powder
Product Categories: Aromatic Nitriles; Chlorine Compounds; Nitriles; Alpha sort; C; CAlphabetic; CHEnvironmental Standards; Metabolites; Pesticides & Metabolites; C6 to C7; Cyanides/Nitriles; Nitrogen Compounds
Canonical SMILES: C1=CC=C(C(=C1)C#N)Cl
InChI: InChI=1S/C7H4ClN/c8-7-4-2-1-3-6(7)5-9/h1-4H
InChIKey: NHWQMJMIYICNBP-UHFFFAOYSA-N

Toxicity Data With Reference

1.    

eye-rbt 100 mg/24H MOD

    28ZPAK    Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,160.
2.    

orl-mus LD50:>300 mg/kg

    JMCMAR    Journal of Medicinal Chemistry. 21 (1978),906.
3.    

ipr-mus LD50:150 mg/kg

    NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD691-490 .

 o-chlorotolunitrile (CAS NO.873-32-5) hasn't been listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65. And the toxicological properties have not been fully investigated. You can see actual entry in RTECS for complete information.

Consensus Reports

Reported in EPA TSCA Inventory. Cyanide and its compounds are on the Community Right-To-Know List.

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion. An eye irritant. When heated to decomposition or on contact with water, steam, acid, or acid fumes it emits toxic fumes of Cl and CN. See also NITRILES.
Hazard Codes: HarmfulXn,IrritantXi
Hazard Note:Harmful/Irritant
The Risk Statements information of o-chlorotolunitrile (CAS NO.873-32-5): 21/22-36-21/22/23
36:  Irritating to the eyes 
21/22:  Harmful in contact with skin and if swallowed  
20/21/22:  Harmful by inhalation, in contact with skin and if swallowed 
The Safety Statements information of o-chlorotolunitrile (CAS NO.873-32-5): 23
23:  Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) 
RIDADR:3439
WGK Germany:2
RTECS:DI2625000

Specification

 o-chlorotolunitrile , its cas register number 873-32-5. It also can be called NSC 8438 ; Nitril kyseliny o-chlorbenzoove ; Nitril kyseliny o-chlorbenzoove [Czech] ; o-Chlorbenzonitril ; o-Chlorbenzonitril [Czech] ; o-Chlorobenzonitrile ; o-Chlorocyanobenzene ; and o-Cyanochlorobenzene . Its classification code is Skin / Eye Irritant.
 o-chlorotolunitrile (CAS NO.873-32-5) could be stable under normal temperatures and pressures. It should avoid the condition like incompatible materials. It is not compatible with strong oxidizing agents, strong reducing agents, strong acids, strong bases. And also prevent it to broken down into hazardous decomposition products: hydrogen chloride, nitrogen oxides, carbon monoxide, carbon dioxide. However, its hazardous polymerization has not been reported.