Carbohydrazide
[CAS# 497-18-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Hydrazine
• Name: Carbohydrazide
• Synonyms: 1,3-Diaminourea; Carbonic dihydrazide
• Molecular Formula: CH₆N₄O
• Molecular Weight: 90.08
• CAS Registry Number: 497-18-7
• EC Number: 207-837-2
• SMILES: C(=O)(NN)NN

Properties

• Density: 1.02
• Melting point: 152-153 °C

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H302-H315-H317-H319-H335-H411
• Safety Statements: P261-P264-P264+P265-P270-P271-P272-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1	H317
Skin sensitization	Skin Sens.	1B	H317
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Self-reactive substances or mixtures	Self-react.	A	H240
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Carbohydrazide, a chemical compound with the formula C2H4N4O, has found widespread use in various industrial and chemical applications due to its unique properties. The substance, also known by its systematic name 1,2-dihydrazinecarboxamide, is a versatile agent in the fields of polymer chemistry, material science, and analytical chemistry.

The discovery of carbohydrazide dates back to the early 20th century when it was first synthesized as part of research into hydrazine derivatives. Its synthesis involves the reaction of hydrazine with carbon dioxide, resulting in a compound with two hydrazine groups attached to a central carbonyl group. This structure provides carbohydrazide with its distinctive reactivity and functional properties.

In the realm of polymer chemistry, carbohydrazide is utilized as a curing agent and cross-linker. Its ability to form strong covalent bonds with other polymers makes it an effective agent for enhancing the mechanical properties and stability of polymeric materials. For instance, in the production of polyurethanes and epoxy resins, carbohydrazide can be used to improve the hardness and chemical resistance of the final product. The compound reacts with isocyanates and epoxy groups, facilitating the formation of cross-linked networks that contribute to the durability and performance of the polymers.

Another significant application of carbohydrazide is in the field of water treatment. The compound is employed as a reducing agent in various water purification processes, including the removal of heavy metals and the treatment of industrial effluents. Its ability to donate electrons makes it useful in neutralizing oxidizing agents and facilitating the reduction of contaminants in water systems. This application is crucial for maintaining water quality and ensuring environmental compliance in industrial settings.

Carbohydrazide also plays a role in analytical chemistry as a reagent in various assays and detection methods. It is used in the synthesis of hydrazone derivatives, which are valuable in the detection and quantification of aldehydes and ketones. The reaction of carbohydrazide with carbonyl compounds forms stable hydrazone products, which can be measured to determine the concentration of these compounds in a sample.

In addition to these applications, carbohydrazide is explored for its potential use in pharmaceutical and medicinal chemistry. Research into its biological activity has indicated that it may have potential as an antimicrobial and anticancer agent. Its hydrazine moiety, combined with its ability to interact with various biological targets, makes it a subject of interest in drug development.

Overall, carbohydrazide is a versatile chemical with diverse applications across several fields. Its role as a curing agent, reducing agent, and analytical reagent highlights its importance in industrial processes, environmental management, and chemical analysis. As research continues, new applications and improvements in its usage may further expand its utility.

References

2024. A novel copper(ii) complex with a salicylidene carbohydrazide ligand that promotes oxidative stress and apoptosis in triple negative breast cancer cells. Dalton Transactions, 53(43).
DOI: 10.1039/d4dt01914h

2024. Design, synthesis, and in silico insights of novel N’-(2-oxoindolin-3-ylidene)piperidine-4-carbohydrazide derivatives as VEGFR-2 inhibitors. Bioorganic Chemistry, 153.
DOI: 10.1016/j.bioorg.2024.107829