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422649

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

Quality Level

100

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP6868
MKCN4737
MKCN2170
MKCM4057
MKCJ0884

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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)
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)
Synthesis of sulfonamide-substituted phthalocyanines.
Carvalho EFA, et al.
Tetrahedron Letters, 50(49), 6882-6885 (2009)
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)
Sterically demanded unsymmetrical zinc phthalocyanines for dye-sensitized solar cells.
Giribabu L, et al.
Dyes and Pigments, 98(3), 518-529 (2013)
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