N,N-Dimethylformamide
[CAS# 68-12-2]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: N,N-Dimethylformamide
• Synonyms: Dimethyl formamide; Formyldimethylamine; DMF; DMFA
• Molecular Formula: C₃H₇NO
• Molecular Weight: 73.09
• CAS Registry Number: 68-12-2
• EC Number: 200-679-5
• SMILES: CN(C)C=O

Properties

• Water solubility: Miscible
• Density: 0.9±0.1 g/cm³, Calc.^*, 0.944 g/mL
• Melting point: -61 °C
• Index of Refraction: 1.396, Calc.^*, 1.431
• Boiling Point: 153.0±0.0 °C (760 mmHg), Calc.^*, 153 °C
• Flash Point: 57.8±0.0 °C, Calc.^*, 58 °C
• alpha: 0.94 °

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

Safety Data

• Hazard Symbols: GHS02;GHS07;GHS08 Danger
• Risk Statements: H226-H312-H319-H332-H360
• Safety Statements: P203-P210-P233-P240-P241-P242-P243-P261-P264+P265-P271-P280-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P317-P318-P321-P337+P317-P362+P364-P370+P378-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Reproductive toxicity	Repr.	1B	H360
Flammable liquids	Flam. Liq.	3	H226
Reproductive toxicity	Repr.	1B	H360D
Acute toxicity	Acute Tox.	3	H331
Organic peroxides	Org. Perox.	C	H242
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin sensitization	Skin Sens.	1	H317
Skin irritation	Skin Irrit.	2	H315
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Reproductive toxicity	Repr.	1B	H360Df
Specific target organ toxicity - single exposure	STOT SE	1	H370
Germ cell mutagenicity	Muta.	2	H341
Serious eye damage	Eye Dam.	1	H318
Reproductive toxicity	Repr.	1A	H360
Eye irritation	Eye Irrit.	2A	H319
Carcinogenicity	Carc.	1B	H350
Reproductive toxicity	Repr.	1B	H360D

• Transport Information: UN 2265

Discovery and Applications

N,N-Dimethylformamide (DMF) is an organic compound with the molecular formula C3H7NO, known for its versatility as a polar aprotic solvent. It is a colorless, hygroscopic liquid that possesses a faint amine-like odor. The compound has gained significance in various industrial and research applications due to its unique chemical properties.

The discovery of DMF dates back to the early 1950s, with its first synthesis reported by German chemist Hermann Staudinger and his colleagues. They produced DMF through the reaction of dimethylamine with formic acid, leading to the formation of this important solvent. Following its discovery, DMF quickly gained attention for its ability to dissolve a wide range of polar and nonpolar substances, making it a valuable resource in many fields.

One of the primary applications of N,N-Dimethylformamide is in the pharmaceutical industry. It serves as a solvent for various reactions and processes, including the synthesis of active pharmaceutical ingredients (APIs). Its ability to solubilize both polar and nonpolar compounds makes it an ideal medium for the chemical reactions involved in drug development. Additionally, DMF is utilized in the formulation of certain medications, enhancing the solubility and stability of active ingredients.

In the field of polymer science, DMF plays a crucial role as a solvent in the preparation of polymers and polymeric materials. It is commonly used in the production of polyacrylonitrile (PAN) and polyurethanes, among other polymers. The solvent's ability to dissolve polymers at elevated temperatures facilitates the spinning of fibers and the formation of coatings, contributing to the development of various advanced materials used in textiles, coatings, and adhesives.

Another significant application of DMF is in the field of organic synthesis. It is often employed as a solvent for reactions such as nucleophilic substitutions and coupling reactions. Its polar nature allows for better solvation of reactants, promoting reaction efficiency and yields. Furthermore, DMF is used in the preparation of various chemical intermediates, including agrochemicals, dyes, and specialty chemicals.

DMF is also utilized in the extraction and purification processes in analytical chemistry. Its properties enable it to act as a solvent for the separation and identification of various compounds in complex mixtures. This capability is essential for environmental monitoring, food safety testing, and quality control in various industries.

Despite its many beneficial applications, safety considerations surrounding DMF are important. The compound is known to be toxic and potentially harmful upon prolonged exposure. Inhalation or skin contact can lead to irritation and other health issues, making proper handling and protective measures essential for those working with DMF in laboratory or industrial settings.

In summary, N,N-Dimethylformamide is a valuable organic compound with a diverse range of applications in pharmaceuticals, polymer science, organic synthesis, and analytical chemistry. Its discovery in the early 1950s marked the beginning of its widespread use, and it continues to play a vital role in various scientific and industrial processes today.

References

1979. Synthesis of amino acyl adenylates using the tert-butoxycarbonyl protecting group. Journal of Molecular Evolution, 13(3).
DOI: 10.1007/bf01732866