873-32-5 Usage
Chemical Properties
white to light yellow crystal powder
Uses
Different sources of media describe the Uses of 873-32-5 differently. You can refer to the following data:
1. Intermediate 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.
2. 2-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.
Preparation
2-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 Explosibility
Notclassified
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 Cland CN-. See also NITRILES.
Synthesis
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 Methods
Crystallise the nitrile to a constant melting point from *benzene/pet ether (b 40-60o). [Beilstein 9 IV 965.]
Check Digit Verification of cas no
The CAS Registry Mumber 873-32-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,7 and 3 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 873-32:
(5*8)+(4*7)+(3*3)+(2*3)+(1*2)=85
85 % 10 = 5
So 873-32-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H4ClN/c8-7-4-2-1-3-6(7)5-9/h1-4H
873-32-5Relevant articles and documents
A DFT-assisted mechanism for evolution of the ammoxidation of 2-chlorotoluene (2-CLT) to 2-chlorobenzonitrile (2-CLBN) over alumina-supported V2O5 catalyst prepared by a solution combustion method
Dwivedi, Ritambhara,Sharma, Prabhakar,Sisodiya, Akrati,Batra, Manohar Singh,Prasad, Rajendra
, p. 245 - 257 (2017)
Ammoxidation of 2-chlorotoluene (2-CLT) has been carried out over vanadates and supported vanadates in the temperature range 350–450 °C. The catalysts were characterized by XRD, XPS, FT-IR, and Raman and surface area measurement. A maximum yield of 76% of 2-CLBN was obtained at a temperature of 425 °C and a 2-CLT:NH3:air mole ratio of 1:8:22. DFT computations suggest that the reaction follows a Mars–van Krevelen (MVK) type of redox mechanism. The catalyst is first reduced by ammonia, producing an imine species. The 2-CLT molecule is also adsorbed through a vanadyl oxygen to produce a CH2[dbnd]C6H5 species. This moiety is adsorbed over the catalyst through an imine formed on the surface to produce 2-chlorobenzonitrile. XPS spectra of fresh and spent catalysts confirm reduction of the catalyst during ammoxidation.
Synthetic method of o-chlorobenzonitrile
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Paragraph 0037-0044; 0069-0076, (2021/03/18)
The invention discloses a synthesis method of o-chlorobenzonitrile, which comprises the following steps: by using one or more than two of o-chlorobenzyl alcohol, o-chlorobenzaldehyde and o-chlorobenzoic acid as raw materials, carrying out ammoxidation reaction in an ammonia gas and oxygen atmosphere under the actions of a copper-manganese composite catalyst and a cooxidant to synthesize the o-chlorobenzonitrile. By adopting the copper-manganese composite catalyst, one or more than two of the raw materials of o-chlorobenzyl alcohol, o-chlorobenzaldehyde and o-chlorobenzoic acid are subjected toammoxidation reaction to generate o-chlorobenzonitrile in the atmosphere of ammonia gas and oxygen under the synergistic action of the oxidant, so that the generation of byproducts is reduced, the difficulty of subsequent separation and purification is reduced, and the yield of o-chlorobenzonitrile is improved. The yield and purity of o-chlorobenzonitrile are improved, and the problems of low yield and high cost of o-chlorobenzonitrile caused by difficult separation and purification of products in the prior art are avoided.
One pot synthesis of aryl nitriles from aromatic aldehydes in a water environment
Chen, Qingqing,Han, Hongwei,Lin, Hongyan,Ma, Xiaopeng,Qi, Jinliang,Wang, Xiaoming,Yang, Yonghua,Zhou, Ziling
, p. 24232 - 24237 (2021/07/29)
In this study, we found a green method to obtain aryl nitriles from aromatic aldehyde in water. This simple process was modified from a conventional method. Compared with those approaches, we used water as the solvent instead of harmful chemical reagents. In this one-pot conversion, we got twenty-five aryl nitriles conveniently with pollution to the environment being minimized. Furthermore, we confirmed the reaction mechanism by capturing the intermediates, aldoximes.