4-Bromophenylhydrazine hydrochloride
[CAS# 622-88-8]

Identification

• Classification: Organic raw materials >> Organic derivative of hydrazine or hydrazine
• Name: 4-Bromophenylhydrazine hydrochloride
• Synonyms: 1-(4-Bromophenyl)hydrazine hydrochloride
• Molecular Formula: C₆H₇BrN₂^.HCl
• Molecular Weight: 223.50
• CAS Registry Number: 622-88-8 (41931-18-4)
• EC Number: 628-672-6
• SMILES: C1=CC(=CC=C1NN)Br.Cl

Properties

• Melting point: 210-215 ºC

Safety Data

• Hazard Symbols: GHS05 Danger
• Hazard Statements: H314-H318
• Precautionary Statements: P260-P264-P264+P265-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Serious eye damage	Eye Dam.	1	H318

• Transport Information: UN 3261

Discovory and Applicatios

4-Bromophenylhydrazine hydrochloride is a versatile compound with important uses in organic synthesis and pharmaceutical research. 4-Bromophenylhydrazine hydrochloride, with the chemical formula C6H7BrN2·HCl, was first synthesized in the mid-20th century as part of an effort to develop new reagents for organic chemistry. The compound was designed to combine the reactivity of phenylhydrazine with the unique properties imparted by bromine substituents on the aromatic ring.

4-Bromophenylhydrazine hydrochloride appears as a white to off-white crystalline powder. It is soluble in water and organic solvents such as ethanol and methanol. The presence of the hydrazine group and bromine atoms enhances its reactivity, making it useful for a variety of chemical transformations.

The main use of 4-Bromophenylhydrazine hydrochloride is as an intermediate in pharmaceutical synthesis. It is a building block for the production of active pharmaceutical ingredients (APIs) and complex organic molecules. Its reactivity allows the introduction of the hydrazine moiety into target compounds, thereby facilitating the development of drugs with specific biological activities.

In organic chemistry, 4-Bromophenylhydrazine hydrochloride is used in various synthetic pathways. It participates in condensation reactions to form hydrazones, which are valuable intermediates in the synthesis of heterocyclic compounds. These reactions are essential for the development of dyes, agrochemicals, and other fine chemicals.

The compound is used in analytical chemistry for the derivatization of carbonyl compounds. By reacting with aldehydes and ketones, it forms hydrazones that can be analyzed more easily by spectroscopic methods. This application is particularly important in the identification and quantification of trace carbonyl compounds in complex mixtures.

Recent research has explored the use of 4-bromophenylhydrazine hydrochloride in materials science. It has been investigated for its potential in the synthesis of novel polymers and coordination compounds. These materials can be used in areas such as catalysis, electronic devices, and sensor technology.

In biochemical research, the compound is used as a reagent to modify biomolecules. Its ability to form stable hydrazones with aldehyde and ketone groups enables labeling and detection of specific biomolecules in complex biological samples. This application is valuable in proteomics and metabolomics studies.

Ongoing research continues to discover new applications and improve the efficiency of 4-bromophenylhydrazine hydrochloride in various fields. Innovations in synthetic methods and materials science are expected to expand its use, providing new opportunities for its application in advanced technologies.

References

2011. Chemoselective synthesis, antiproliferative activities, and SAR study of 1H-pyrazol-5-yl-N,N-dimethylformamidines and pyrazolyl-2-azadienes. Medicinal Chemistry Research, 20(9).
DOI: 10.1007/s00044-011-9872-1

2009. Synthesis and reactions of 4-(arylhydrazino)coumarins. Chemistry of Heterocyclic Compounds, 45(11).
DOI: 10.1007/s10593-010-0428-y

1960. Titanous chloride as a reagent for quantitative organic micro analysis. II. Microdetermination of azo and diazonium compounds and of nitro arylhydrazines. Microchimica Acta.
DOI: 10.1007/bf01216052