Formamide
[CAS# 75-12-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Fluoropyrimidine
• Name: Formamide
• Synonyms: Carbamoyl
• Molecular Formula: CH₃NO
• Molecular Weight: 45.04
• CAS Registry Number: 75-12-7
• EC Number: 200-842-0
• SMILES: C(=O)N

Properties

• Density: 1.133 g/mL (20 )
• Melting point: 2-3 °C
• Boiling point: 210 °C
• Refractive index: 1.4475
• Flash point: 175 °C
• Water solubility: miscible

Safety Data

• Hazard Symbols: GHS08 Danger
• Risk Statements: H351-H360-H373
• Safety Statements: P203-P260-P280-P318-P319-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Reproductive toxicity	Repr.	1B	H360
Carcinogenicity	Carc.	2	H351
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Reproductive toxicity	Repr.	1B	H360D
Eye irritation	Eye Irrit.	2	H319
Reproductive toxicity	Repr.	1B	H360D

Discovery and Applications

Formamide, with the chemical formula CH3NO, is a colorless, hygroscopic liquid that is the simplest amide derived from formic acid. It has a distinctive odor and is soluble in water and organic solvents. The discovery of formamide can be traced back to the early 19th century when it was first identified by chemists studying the properties of formic acid. In 1859, the French chemist Auguste Laurent reported the synthesis of formamide through the reaction of formic acid with ammonia, marking a significant milestone in understanding its chemical properties.

Formamide has since gained widespread recognition for its various applications across multiple fields, particularly in chemistry, biology, and industry. One of its primary uses is as a solvent in chemical reactions and laboratory processes. Its ability to dissolve a wide range of organic and inorganic compounds makes it an essential medium in various synthetic procedures. Formamide is particularly valuable in peptide synthesis, where it is used to solubilize amino acids and promote their coupling during the formation of peptide bonds.

In addition to its role as a solvent, formamide serves as a reagent in organic synthesis. It is commonly employed in the preparation of other chemical compounds, including pharmaceuticals and agrochemicals. Formamide is utilized in the synthesis of formamide derivatives, which exhibit diverse biological activities, including anti-inflammatory, antitumor, and antimicrobial properties. Its role in drug discovery has made it a crucial component in the development of new therapeutic agents.

Formamide is also significant in molecular biology, where it is used in various laboratory techniques. It is commonly employed in the preparation of nucleic acid solutions and hybridization experiments, particularly in techniques such as in situ hybridization and fluorescence in situ hybridization (FISH). Formamide's ability to disrupt hydrogen bonding between nucleic acid strands allows for improved accessibility during hybridization, enhancing the sensitivity and specificity of these methods.

Moreover, formamide plays a role in the production of plastics and resins. It is used as a plasticizer and a solvent in the formulation of thermosetting plastics, contributing to improved flexibility and processability. Its presence in these materials enhances their mechanical properties, making formamide-containing plastics suitable for various applications, including coatings, adhesives, and composites.

Despite its many beneficial applications, safety considerations are crucial when handling formamide. It is classified as a hazardous substance due to its potential health effects, including skin and eye irritation, as well as respiratory sensitization. Prolonged exposure may lead to more severe health issues, including reproductive toxicity. Therefore, appropriate safety measures, including the use of personal protective equipment and proper ventilation, should be implemented when working with formamide.

In summary, formamide is a versatile and essential chemical compound with a rich history of discovery and a broad spectrum of applications in organic synthesis, molecular biology, and materials science. Its significance in both historical and contemporary contexts underscores its value in various scientific and industrial fields.

References

1990. Expression patterns of mRNAs for ammonia-metabolizing enzymes in the developing rat: the ontogenesis of hepatocyte heterogeneity. Journal of Molecular Histology, 22(9).
DOI: 10.1007/bf01007229

1979. Free cytoplasmic messenger ribonucleoprotein complexes from rabbit reticulocytes. Molecular Biology Reports, 5(2).
DOI: 10.1007/bf00777489