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Merck
CN

25980

Sigma-Aldrich

4-Chlorophenylhydrazine hydrochloride

purum, ≥98.0% (AT)

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About This Item

Linear Formula:
ClC6H4NHNH2 · HCl
CAS Number:
1073-70-7
Molecular Weight:
179.05
Beilstein:
3596254
EC Number:
214-030-9
MDL number:
MFCD00012943
UNSPSC Code:
12352100
PubChem Substance ID:
329752839

Key Documents

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grade

purum

Assay

≥98.0% (AT)

mp

216 °C (dec.) (lit.)

SMILES string

Cl.NNc1ccc(Cl)cc1

InChI

1S/C6H7ClN2.ClH/c7-5-1-3-6(9-8)4-2-5;/h1-4,9H,8H2;1H

InChI key

YQVZREHUWCCHHX-UHFFFAOYSA-N

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General description

4-Chlorophenylhydrazine hydrochloride reacts with 3-acetonyl-5-cyano-1,2,4-thiadiazole to yield 5-cyano-3-(5-chloro-2-methylindol-3-yl)-1,2,4-thiadiazole and 5-cyano-3-[1-(4-chlorophenyl)-3,5-dimethylpyrazol-4-yl]-1,2,4-thiadiazole.

Application

4-Chlorophenylhydrazine hydrochloride has been used in preparation of:
  • 5-methoxy-1H-indole-3-carbaldehyde(4-chlorophenyl)hydrazone
  • 4-iodoacetophenone 4-chlorophenylhydrazone

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H312 + H332

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

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

Regulatory Information

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Taryn P Homes et al.
Bioorganic & medicinal chemistry, 14(11), 3938-3946 (2006-02-17)
A series of N,N-dialkyl-2-phenylindol-3-ylglyoxylamides bearing the halogens iodine and bromine were synthesised and their binding affinity for the peripheral benzodiazepine binding sites (PBBS) in rat kidney mitochondrial membranes was evaluated using [(3)H]PK11195. Central benzodiazepine receptor (CBR) affinities were also evaluated
Marco Catto et al.
European journal of medicinal chemistry, 45(4), 1359-1366 (2010-02-09)
Biological screening of (hetero)aromatic compounds allowed the identification of some novel inhibitors of Abeta(1-40) aggregation, bearing indane and indole rings as common scaffolds. Molecular decoration of lead compounds led to inhibitors exhibiting a potency, measured by the Thioflavin T fluorimetric
J P Mahy et al.
European journal of biochemistry, 226(2), 445-457 (1994-12-01)
The reaction of p-chlorophenylhydrazine with prostaglandin H synthase (PGHS) Fe(III) under aerobic conditions leads to a partial destruction of the heme and to a new complex absorbing at 436 nm. This complex is also obtained by reaction of p-chlorophenyldiazene (pClPhN
T Iwakawa et al.
Chemical & pharmaceutical bulletin, 48(1), 160-162 (2000-03-08)
Treatment of 3-acetonyl-5-cyano-1,2,4-thiadiazole (1) with 4-methyl or 4-methoxyphenylhydrazine hydrochloride provided 5-cyano-3-(2,5-dimethylindol-3-yl)-1,2,4-thiadiazole (2) or 5-cyano-3-(5-methoxy-2-methylindol-3-yl)-1,2,4-thiadiazole (3) as the sole product, respectively. In contrast, treatment of 1 with phenylhydrazine hydrochloride resulted in the formation of 5-cyano-3-(2-methylindol-3-yl)-1,2,4-thiadiazole (4) and the unexpected 5-cyano-3-(3,5-dimethyl-1-phenylpyrazol-4-yl)-1,2,4-thiadiazole (5).

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