4-Methoxyphenylhydrazine hydrochloride
[CAS# 19501-58-7]

Identification

• Classification: Organic raw materials >> Organic derivative of hydrazine or hydrazine
• Name: 4-Methoxyphenylhydrazine hydrochloride
• Synonyms: 1-(4-Methoxyphenyl)hydrazine hydrochloride
• Molecular Formula: C₇H₁₀N₂O.HCl
• Molecular Weight: 174.63
• CAS Registry Number: 19501-58-7
• EC Number: 243-115-3
• SMILES: COC1=CC=C(C=C1)NN.Cl

Properties

• Melting point: 160-162 °C (dec.)
• Water solubility: soluble

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H317-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P272-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Skin sensitization	Skin Sens.	1	H317
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

4-Methoxyphenylhydrazine hydrochloride is a compound of interest in organic chemistry, primarily used for its role in synthesis. This chemical consists of a methoxy group (-OCH3) attached to a phenyl ring, with a hydrazine group (-NHNH2) forming the core of its reactivity. The hydrochloride salt form enhances its stability, making it easier to handle and use in various applications.

The discovery of 4-methoxyphenylhydrazine hydrochloride was driven by efforts to explore the utility of hydrazine derivatives in organic reactions. Hydrazines are known for their ability to undergo various transformations, such as forming hydrazones, which are key intermediates in organic synthesis. The addition of a methoxy group to the phenyl ring of hydrazine further expands its usefulness by altering its electronic properties, making it more reactive under certain conditions.

In pharmaceutical chemistry, 4-methoxyphenylhydrazine hydrochloride has been used as a precursor for synthesizing bioactive molecules. The hydrazine group is reactive toward carbonyl compounds, allowing the formation of hydrazones, which can further be transformed into other functional groups. Research has indicated that derivatives of 4-methoxyphenylhydrazine may exhibit significant biological activity, including potential anticancer and antiviral effects. Its role as an intermediate makes it a valuable compound in drug development and discovery.

This compound also finds applications in dye chemistry, where it is employed in the synthesis of azo dyes. The hydrazine group reacts with diazonium salts to form azo compounds, which are widely used in the textile and pigment industries due to their vibrant colors and stability. The presence of the methoxy group can influence the color properties of the resulting dyes, making 4-methoxyphenylhydrazine hydrochloride a useful reagent in this sector.

Furthermore, 4-methoxyphenylhydrazine hydrochloride is valuable in organic synthesis. Its functional groups allow for a range of chemical transformations, and it is often used to introduce the hydrazine functionality into more complex molecules. This versatility makes it an important reagent for creating novel compounds in academic and industrial research.

Overall, 4-methoxyphenylhydrazine hydrochloride plays a crucial role in various fields, including pharmaceuticals, dye chemistry, and organic synthesis, making it a compound of broad utility in modern chemical research.

References

2023. Novel pyrazolothienopyridinones as potential GABAA receptor modulators. Monatshefte für Chemie - Chemical Monthly, 154(4).
DOI: 10.1007/s00706-023-03063-6

2023. Tunable Aggregation-induced Emission and Emission Colors of Imidazolium and Pyridinium Based Hydrazones. Journal of Fluorescence, 33(3).
DOI: 10.1007/s10895-023-03202-6

2022. Radical Reaction and Photoreaction. Handbook of Fullerene Science and Technology.
DOI: 10.1007/978-981-16-8994-9_46"