Hydrazide
[CAS# 32687-78-8]

Identification

• Classification: Catalysts and additives >> Antioxidant
• Name: Hydrazide
• Synonyms: 2',3-Bis[[3-[3,5-di-tert-butyl-4-hydroxyphenyl]propionyl]]propionohydrazide; Antioxidant 1024
• Molecular Formula: C₃₄H₅₂N₂O₄
• Molecular Weight: 552.80
• CAS Registry Number: 32687-78-8
• EC Number: 251-156-3
• SMILES: CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)CCC(=O)NNC(=O)CCC2=CC(=C(C(=C2)C(C)(C)C)O)C(C)(C)C

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 60-67 °C
• Index of Refraction: 1.535, Calc.^*
• Boiling Point: 652.6±55.0 °C (760 mmHg), Calc.^*
• Flash Point: 348.5±31.5 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317-H319
• Safety Statements: P280-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	2	H300
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Skin irritation	Skin Irrit.	2	H315
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Hydrazide refers to a class of organic compounds characterized by the presence of a hydrazine functional group (–NH–NH2) attached to a carbonyl group (C=O). This structure lends hydrazides unique properties that have made them significant in various fields, including medicinal chemistry, agriculture, and material science. The discovery of hydrazides can be traced back to the early 20th century when researchers began to explore the reactivity of hydrazine and its derivatives in organic synthesis.

The synthesis of hydrazides typically involves the reaction of hydrazine with carboxylic acids or their derivatives, such as acid chlorides or anhydrides. This straightforward synthetic route enables the preparation of a wide range of hydrazides with varying alkyl or aryl substituents, making them highly versatile compounds.

One of the primary applications of hydrazides is in the field of pharmaceuticals. Many hydrazide derivatives have been investigated for their biological activity and therapeutic potential. For example, isoniazid, a well-known hydrazide, is widely used as an antibiotic in the treatment of tuberculosis. Its mechanism of action involves inhibiting the synthesis of mycolic acids in the cell wall of Mycobacterium tuberculosis, thereby effectively treating the infection. Additionally, other hydrazide compounds have shown promise in anticancer, anti-inflammatory, and antiviral activities, highlighting their potential in drug development.

In agriculture, hydrazides have been utilized as plant growth regulators. Compounds such as maleic hydrazide are employed to control plant growth and development by inhibiting cell division. This property is particularly valuable in crop management, where maleic hydrazide is applied to prevent the sprouting of tubers and bulbs, thus enhancing the shelf life of stored produce. Furthermore, hydrazides have been studied for their potential use in herbicides and fungicides, contributing to sustainable agricultural practices.

Another area where hydrazides find application is in material science, particularly in the development of polymers and composites. Hydrazides can act as crosslinking agents, improving the mechanical and thermal properties of polymer matrices. Their ability to form stable bonds with various substrates makes them useful in enhancing the performance of coatings, adhesives, and sealants. In addition, hydrazide-functionalized polymers have been explored for applications in drug delivery systems and biosensors, owing to their biocompatibility and responsiveness to environmental stimuli.

Despite their many benefits, safety considerations are essential when handling hydrazides. Some hydrazides may pose health risks, including potential carcinogenicity and toxicity upon exposure. Therefore, proper safety protocols must be implemented during their synthesis and application, and regulatory assessments are crucial to ensure safe usage in industrial and agricultural settings.

In summary, hydrazides represent a versatile class of compounds with significant applications across various sectors, including pharmaceuticals, agriculture, and materials science. Their unique chemical properties enable a wide range of functions, from antibiotic activity to plant growth regulation and polymer modification. As research continues to uncover new hydrazide derivatives and their potential uses, this class of compounds is likely to remain an important focus in chemical and material sciences.

References

2019. Conductive cotton fabric through thermal reduction of graphene oxide enhanced by commercial antioxidants used in the plastics industry. Cellulose, 26(3).
DOI: 10.1007/s10570-018-02233-8