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Home > Encyclopedia > 2-Chloro-1,3-benzenedicarbonitrile

2-Chloro-1,3-benzenedicarbonitrile

2-Chloro-1,3-benzenedicarbonitrile structure

2-Chloro-1,3-benzenedicarbonitrile 

structure
  • CAS No:

    28442-78-6

  • Formula:

    C8H3ClN2

  • Chemical Name:

    2-Chloro-1,3-benzenedicarbonitrile

  • Synonyms:

    1,3-Benzenedicarbonitrile,2-chloro-;Isophthalonitrile,2-chloro-;2-Chloro-1,3-benzenedicarbonitrile;2-Chloroisophthalonitrile;2-Chloro-1,3-dicyanobenzene

  • Categories:

    Chemical Reagents  >  Organic Reagents

2-Chloro-1,3-benzenedicarbonitrile Basic Attributes

162.57582

162.58

DTXSID90182642

2926909090

Characteristics

47.6

2

1.3±0.1 g/cm3

154-156 °C

294.4°C at 760 mmHg

135.6±16.0 °C

1.586

0.00163mmHg at 25°C

2-Chloro-1,3-benzenedicarbonitrile Use and Manufacturing

Methods of Manufacturing

3-Amino-2-carbomethoxy-7-cyano-benzthiophene 1.00 g (3.01 mmol) of 3, 3'-non-9H-carbazole and 1.66 g (12.0 mmol) of potassium carbonate were placed in a 100 ml three-necked flask, and the flask was purged with nitrogen. N, N-dimethylformamide (24.0 ml) was added to the mixture, and the mixture was stirred at room temperatureAnd stirred for 2 hours. After 1.80 g (11.1 mmol) of In a 500-mL round-bottom flask, is added p-CP-2Br (1.2 equiv.) and 250 mL of anhydrous THF. The solution is placed in dry ice / acetone bath for 15 mm before dropwisely adding nBuLi (2.5 M in n-hexane, 1.3 equiv.) to result in a yellow slurry. The reaction mixture is allowed to stir at -78 C for 0.5 h. Then THF solution (30 mL) of 1.63 g (10.0 mmol) of 2-chloro-1 , 3-dicyano-benzene, 2.07 g (10.0 mmol) of 6H- benzimidazolo[1 , 2-a]benzimidazole and 2.12 g (10.0 mmol) of tripotassium phosphate in 50 ml of DMF are stirred for 24 h at 150 C. The reaction mixture is cooled at room temperature and added water, then the precipitate is filterted off. Gradient column chromatography on silica gel with dichloromethane/ethyl acetate (dichloromethane100%, 9/1 , 4/1 ) gives the product. Yield 2.80 g (84 %). 1H NMR (400 MHz, CDCI3): delta 8.19 (d, 2H); 7.95 - 7.87 (m, 2H); 7.86 (t, 1 H); 7.79 (dd, 1 H); 7.49 (td, 1 H); 7.46 - 7.35 (m, 3H); 7.15 (dt, 1 H).A mixture of 3, 3?-dicarbazyl (3 mmol, 1 g),

Environmental transformation -> Pesticide transformation products (metabolite, successor)

2-chloroisophthalonitrile is a known environmental transformation product of Chlorothalonil.

Computed Properties

Molecular Weight:162.57
XLogP3:2
Hydrogen Bond Acceptor Count:2
Exact Mass:161.9984758
Monoisotopic Mass:161.9984758
Topological Polar Surface Area:47.6
Heavy Atom Count:11
Complexity:207
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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