2-Chlorobenzonitrile

2-Chlorobenzonitrile Basic information
Product Name:2-Chlorobenzonitrile
Synonyms:2-chloro-benzonitril;2-Chlorophenylcyanide;2-Cyanochlorobenzene;2-Chlorobenzonitrile ,99%;A nitrile o-dichlorobenzene;2-CHLOROBENZONITRILE FOR SYNTHESIS;2-Chlorobenzon;Benzonitrile, 2-chloro-
CAS:873-32-5
MF:C7H4ClN
MW:137.57
EINECS:212-836-5
Product Categories:Nitrogen Compounds;Pesticides intermediate;Aromatic Nitriles;Chlorine Compounds;Nitriles;Alpha sort;C;CAlphabetic;CHEnvironmental Standards;Metabolites;Pesticides&Metabolites;C6 to C7;Cyanides/Nitriles;J's;2-Chlorobenzoni;873-32-5
Mol File:873-32-5.mol
2-Chlorobenzonitrile Structure
2-Chlorobenzonitrile Chemical Properties
Melting point 43-46 °C(lit.)
Boiling point 232 °C(lit.)
density 1,18 g/cm3
refractive index 1.4530 (estimate)
Fp 227 °F
storage temp. Store below +30°C.
solubility 1g/l
form Crystalline Solid
color White to very slightly yellow
BRN 1363916
Exposure limitsNIOSH: IDLH 25 mg/m3
InChIKeyNHWQMJMIYICNBP-UHFFFAOYSA-N
CAS DataBase Reference873-32-5(CAS DataBase Reference)
NIST Chemistry Reference2-Chlorobenzoic acid nitrile(873-32-5)
EPA Substance Registry SystemBenzonitrile, 2-chloro- (873-32-5)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 21/22-36-21/22/23
Safety Statements 23
RIDADR 3439
WGK Germany 2
RTECS DI2625000
Hazard Note Harmful/Irritant
TSCA Yes
HazardClass 6.1
PackingGroup III
HS Code 29269095
MSDS Information
ProviderLanguage
OCBN English
SigmaAldrich English
ACROS English
ALFA English
2-Chlorobenzonitrile Usage And Synthesis
Chemical Propertieswhite to light yellow crystal powder
Uses2-Chlorobenzonitrile is an activated aryl chloride that is commonly used in reactions that involve the Palladium-catalyzed direct arylation of heteroaromatics (e.g. 3-aminopicolinic acid [A627800]). 2-Chlorobenzonitrile and its substituted derivatives (e.g. 2,3-dichloro-6-nitrobenzonitrile [2112-22-3]) also have potential anti-inflammatory properties.
UsesIntermediate for the synthesis of agrochemicals, pharmaceuticals and chemical intermediates. 2-Chlorobenzonitrile is mainly used in the synthesis of dye intermediates 2-cyano-4-nitroaniline, and in the pharmaceutical industry for the synthesis of new anti-malarial drugs such as nitroquine.
Preparation2-chlorobenzonitrile is obtained by the reaction of o-chlorobenzoic acid and urea: o-chlorobenzoic acid, sulfamic acid and urea are mixed and heated to about 140℃ and melted, then reacted vigorously under stirring, and a large amount of gas is released, and the temperature automatically rises to 220-230℃ for 2h. Then it is cooled to below 15℃, filtered, and the solids obtained are washed with 3% ammonia and water to neutral, then dried and the finished products are obtained.
Flammability and ExplosibilityNotclassified
Safety ProfilePoison 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 Cland CN-. See also NITRILES.
SynthesisSynthesis_873-32-5
This embodiment includes the following steps: Step 1. Add 14.3g (0.1mol) o-chlorobenzyl alcohol, 3.7g copper-manganese composite catalyst and 1.6g (0.01mol) 2,2,6,6-tetramethylpiperidine oxide into the reaction kettle, Then add an alcohol-water mixed solution made by mixing 33 mL of ethanol and 66 mL of deionized water, Pour ammonia gas into the reactor until the ammonia gas pressure in the reactor is 0.2MPa, and then close the ammonia gas inlet valve. Continue to feed oxygen into the reaction kettle to a pressure of 0.4MPa, and then continue to supply oxygen at this pressure; The copper-manganese composite catalyst consists of 1.7 g (0.01 mol) copper chloride dihydrate and 2.0 g (0.01 mol) manganese chloride tetrahydrate; Turn on the magnetic stirring device in the reaction kettle, and at the same time heat it to the temperature of the system in the reaction kettle at 40??C to perform ammonia oxidation reaction for 4 hours After the reaction is over, the pressure of the reactor is relieved, the product system after the ammoxidation reaction is cooled to 5??C, and 14.0 g of off-white needle-like solids are obtained by suction filtration, namely crude o-chlorobenzonitrile; Step 2: Using 28 mL of alcohol-water mixed solution to recrystallize 14.0 g of the crude o-chlorobenzonitrile obtained in step 1, to obtain white needle-like crystals, namely o-chlorobenzonitrile; The alcohol-water mixed solution is formed by mixing ethanol and deionized water in a volume ratio of 1:2. The o-chlorobenzonitrile prepared in this example was dried and weighed 13.3g; after calculation, The yield of the o-chlorobenzonitrile prepared in this example was 97.1%, and the mass purity of the o-chlorobenzonitrile prepared in the example was 97.5% as determined by gas chromatography.
Purification MethodsCrystallise the nitrile to a constant melting point from *benzene/pet ether (b 40-60o). [Beilstein 9 IV 965.]
2-Bromomethyl-3-Chlorobenzonitrile 5 - CHLOROBENZONITRILE 5-[3-(4-Amino-2-hydroxyphenyl)ureido]-2-chlorobenzonitrile 2-CHLORO-6-METHOXYBENZONITRILE 2-chloro-6-benzyloxybenzonitrile 2-CHLORO-4-HYDROXYBENZONITRILE 2-(BROMOMETHYL)-5-CHLOROBENZONITRILE 2-Chloro-5-methylbenzonitrile 2-CHLORO-5-NITROBENZONITRILE 2-CHLORO-6-METHYLBENZONITRILE 4-Amino-2-chloro-3-fluorobenzonitrile 2-Nitro-6-chlorobenzonitrile,6-Nitro-2-chlorobenzonitrile 3,5-Bis(trifluoromethyl)-4-chlorobenzonitrile98%,3,5-Bis(trifluoromethyl)-4-chlorobenzonitrile 93% 2-METHYL-4-CHLOROBENZONITRILE 5% 4-BROMO-3-CHLOROBENZONITRILE 4-(aminomethyl)-3-chlorobenzonitrile 2,4-DICHLORO-3,5-DINITROBENZONITRILE 3-Fluoro-2-chlorobenzonitrile

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