N-Vinylformamide
[CAS# 13162-05-5]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: N-Vinylformamide
• Molecular Formula: C₃H₅NO
• Molecular Weight: 71.08
• CAS Registry Number: 13162-05-5
• EC Number: 236-102-9
• SMILES: C=CNC=O

Properties

• Density: 0.9±0.1 g/cm³ Calc.^*, 1.014 g/mL (Expl.)
• Melting point: -16 ºC (Expl.)
• Boiling point: 184.3±13.0 ºC 760 mmHg (Calc.)^*, 210 ºC (Expl.)
• Flash point: 84.5±4.8 ºC (Calc.)^*, 102 ºC (Expl.)
• Index of refraction: 1.406 (Calc.)^*, 1.494 (Expl.)

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

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H302-H315-H318-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P354+P338-P317-P319-P321-P330-P332+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Reproductive toxicity	Repr.	1B	H360

Discovory and Applicatios

N-Vinylformamide is an unsaturated amide that belongs to the class of vinyl monomers developed for polymer chemistry and industrial applications. Its discovery is closely associated with the broader effort, beginning in the mid twentieth century, to design water soluble and highly reactive vinyl monomers that could be polymerized into functional materials. During this period, chemists sought alternatives to existing vinyl compounds that would offer improved control over polymer structure, hydrolysis behavior, and end use properties.

The initial interest in N-vinylformamide arose from systematic studies of N-vinyl amides, a family of compounds characterized by a vinyl group attached to an amide nitrogen. These studies demonstrated that the electronic properties of the amide group could significantly influence polymerization kinetics and the physical characteristics of the resulting polymers. N-Vinylformamide, with the simplest possible amide substituent, became an important reference compound for understanding structure–property relationships within this class of monomers.

Early synthetic routes to N-vinylformamide were established using well defined chemical transformations that avoided excessive byproduct formation and enabled production on a laboratory and later industrial scale. Once reliable synthesis had been achieved, the compound was evaluated for its polymerization behavior under free radical conditions. These investigations showed that N-vinylformamide readily undergoes polymerization to form poly(N-vinylformamide), a polymer notable for its high polarity and strong hydrogen bonding capability.

The major application of N-vinylformamide emerged through its polymer and the derivatives obtained from it. Poly(N-vinylformamide) can be hydrolyzed in a controlled manner to yield polyvinylamine, a polymer that is otherwise difficult to prepare directly. This conversion involves cleavage of the formamide groups while retaining the polymer backbone, producing primary amine functionalities along the chain. The availability of N-vinylformamide as a precursor monomer thus enabled access to polyvinylamine with defined molecular weight and architecture.

Polyvinylamine and partially hydrolyzed poly(N-vinylformamide) have found applications in several industrial sectors. These polymers are used as flocculants and retention aids in paper manufacturing, where their cationic character enhances fiber bonding and filler retention. They have also been applied in water treatment processes, exploiting their ability to interact with negatively charged particles and dissolved contaminants. The role of N-vinylformamide in these applications is indirect but essential, as it provides the chemical entry point for producing these functional polymers.

Beyond paper and water treatment, polymers derived from N-vinylformamide have been studied for use in coatings, adhesives, and textile processing. Their strong affinity for polar surfaces and tunable charge density make them suitable for modifying surface properties and improving adhesion. In research contexts, N-vinylformamide has also served as a model monomer for studying polymerization mechanisms of vinyl amides, contributing to fundamental understanding of reactivity and copolymerization behavior.

From a regulatory and safety perspective, N-vinylformamide has been handled primarily as an industrial chemical intermediate rather than a consumer product. Its assessment has focused on occupational exposure and environmental fate associated with large scale polymer production. The scientific literature describing its properties and uses is grounded in experimental studies of synthesis, polymerization, and application performance, rather than speculative or theoretical claims.

Overall, the discovery and application of N-vinylformamide illustrate how targeted monomer design can enable the creation of entirely new classes of functional polymers. Although the compound itself is rarely encountered outside industrial or research settings, its role as a precursor to technologically important materials has made it a significant substance in the development of modern polymer chemistry.

References

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