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Sigma-Aldrich

4,5-Dichlorophthalonitrile

99%

Synonym(s):

1,2-Dichloro-4,5-dicyanobenzene, 4,5-Dichloro-1,2-benzenedicarbonitrile, 4,5-Dichloro-1,2-dicyanobenzene, 4,5-Dichlorobenzene-1,2-dicarbonitrile, 4,5-Dicyano-1,2-dichlorobenzene

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About This Item

Linear Formula:
Cl2C6H2-1,2-(CN)2
CAS Number:
139152-08-2
Molecular Weight:
197.02
MDL number:
MFCD00191408
UNSPSC Code:
12352100
PubChem Substance ID:
24866445
NACRES:
NA.22

Assay

99%

mp

180-184 °C (lit.)

SMILES string

Clc1cc(C#N)c(cc1Cl)C#N

InChI

1S/C8H2Cl2N2/c9-7-1-5(3-11)6(4-12)2-8(7)10/h1-2H

InChI key

SRIJSZQFAMLVQV-UHFFFAOYSA-N

General description

4,5-Dichlorophthalonitrile (4,5-dichloro-1,2-dicyanobenzene) is a phthalonitrile derivative. It has been synthesized from 4,5-dichloro-1,2-benzenedicarboxamide and characterized by 1H ,13C-NMR and IR. 4,5-dichlorophthalonitrile undergoes base catalyzed nucleophilic aromatic substitution reaction with O-, S- nucleophiles and acidic -CH containing compounds to form corresponding phthalonitrile derivatives, which are the precursors in the synthesis of phthalocyanines.

Application

4,5-Dichlorophthalonitrile is suitable as a reactant in the synthesis of 4,5-bis(3,4-dimethoxyphenyl) phthalonitrile and 4,5-bis(2,6-dimethoxyphenoxy) phthalonitrile. It may be used in the synthesis of 4,5-diphenoxyphthalonitrile.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sterically demanded unsymmetrical zinc phthalocyanines for dye-sensitized solar cells.
Giribabu L, et al.
Dyes and Pigments, 98(3), 518-529 (2013)
A simple synthesis of 4,5-disubstituted 1,2-dicyanobenzenes and 2,3,9,10,16,17,23,24-octasubstituted phthalocyanines.
Wohrle D, et al.
Synthesis, 194-196 (1993)
A novel route to 4-chloro-5-alkyl-phthalonitrile and phthalocyanines derived from it.
Dincer, HA, et al.
Journal of Porphyrins and Phthalocyanines, 8(10), 1204-1208 (2004)
Discotic liquid crystals of transition metal complexes 37*: a thermotropic cubic mesophase having Pn m symmetry exhibited by phthalocyanine-based derivatives.
Ichihara M, et al.
Liq. Cryst., 34(5), 555-567 (2007)
Synthesis and characterization of novel symmetrical phthalocyanines substituted with mono-or bi-macrocycles.
Kandaz M, et al.
Polyhedron, 19(1), 115-121 (2000)
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