2,2-DIFLUOROACETAMIDE CAS 359-38-6

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2,2-DIFLUOROACETAMIDE | Acetamide, 2,2-difluoro

CAS 359-38-6 | C2H3F2NO | 95.05

Appearance: White powder
Purity: 99. 0%min
Stock: In stock
Sample: Available
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Basic Info of 2,2-DIFLUOROACETAMIDE

CAS No:	359-38-6
Name:	2,2-DIFLUOROACETAMIDE
Formula:	C2H3F2NO
Weight:	95.05

Other Names:	Acetamide, 2,2-difluoro
Type:	Organic Raw Material, Other Chemicals
Shelf Life:	3 years
Brand Name:	Zhishang Chemical
Place of Origin:	China

What is 2,2-DIFLUOROACETAMIDE?

2,2-Difluoroacetamide is a stable, opaque powder at room temperature and pressure. It is slightly soluble in water and ether-based organic solvents, but insoluble in N,N-dimethylformamide. 2,2-Difluoroacetamide is a common and essential chemical. Studies have shown that this compound can undergo Mannich condensation reactions with aromatic aldehydes and imines, and can be used as an antioxidant. It has been reported to have high efficiency in the synthesis of α,α-difluoro-β-aminoamides.

2,2-Difluoroacetamide is an organic compound characterized by two fluorine atoms attached to the second carbon atom of the acetaminophen functional group. Its molecular formula is C₂H₂F₂N₂O, thus containing carbon, nitrogen, and sulfur. This compound is usually a white crystalline solid, soluble in water or polar solvents (such as alcohols).

2,2-Difluoroacetamide is a very useful compound in chemical research and industrial applications. Fluorine atoms increase reactivity and affect physical properties such as boiling and melting points. 2,2-Difluoroacetamide is widely used in organic synthesis and also functions as an antioxidant. In addition to its amide properties, it also has the ability to form hydrogen bonds. Safety precautions should be observed when using this compound.

Preparation

The synthesis of 2,2-difluoroacetamide typically involves reducing difluoroacetic acid or its esters to the corresponding acyl chloride, followed by treatment with ammonia to obtain the amide. Furthermore, it has been reported that direct amidation using a coupling enzyme can improve the efficiency of this compound’s synthesis.

2,2-DIFLUOROACETAMIDE Uses

The parent compound in the 2,2-difluoroacetamide structure can be treated with common dehydrating agents to generate the corresponding cyano derivatives. The acyl group of difluoroacetamide can also undergo a cyclic condensation reaction with phenylenediamine at high temperatures. Literature reports that difluoroacetamide can react with aryl iodides and other compounds in the presence of urinary iodine.

Dehydration Condensation Reaction

In a dry reaction flask, 11.6 g of trifluoroacetic acid was added to 146.7 g of pyridine, followed by the slow dropwise addition of 19.2 g of 2,2-difluoroacetamide. Next, 51.2 g of 2,2-dimethylpropionyl chloride was slowly added dropwise to the reaction mixture at 60 °C, and the reaction proceeded for 3 hours. The reaction mixture was then heated to 100 °C, at which point the difluoroacetonitrile was oxidized to give difluoroacetonitrile in 88% yield.

Coupling Reaction

A pressure tube containing 2,2-difluoroacetamide (428 mg, 4.50 mmol) was used for degassing by purging with nitrogen for 10 min. Tris(dibenzylacetone)dipalladium(O) (23.2 mg, 0.025 mmol) was added to the mixture. The mixture was heated to 100 °C and stirred for 16 h. After the reaction was complete, the mixture was cooled to room temperature, and water and the reaction mixture were added. The mixture was extracted with ethyl acetate (3 times), dried over anhydrous sodium sulfate, filtered, and concentrated. The product was purified by silica gel column chromatography.

Mannich Reaction (0-50% ethyl acetate/hexane)

The Mannich reaction of 2,2-difluoroacetamide was carried out at -78 °C in a sodium hexamethyldisilazane (NaHMDS) base. The reaction successfully underwent the Mannich addition reaction, yielding α,α-difluoro-β-aminoamide in 84% yield and with a reaction selectivity of 88:12.

Specifications & Packaging

Specification

Product Nature

Specification

Product Nature

Product Packaging

Application of 2,2-DIFLUOROACETAMIDE

2,2-Difluoroacetamide has a melting point of 51.8°C, a boiling point of 108.63°C (Press: 35 Torr), and a density of 1.291 ± 0.06 g/cm³ (predicted). It is a white to off-white solid, primarily used as an organometallic compound and as a raw material in organic synthesis.

2,2-Difluoroacetamide is a fluorinated compound with the chemical formula CHF₂CONH₂. It possesses a unique skeletal structure in which two hydrogen atoms on the α-carbon are replaced by fluorine atoms. Compared to unsubstituted acetamide, this compound exhibits a strong electron-withdrawing ability, which is related to its higher electron density. This compound was first synthesized in the mid-20th century during systematic studies of fluorinated amides and has been shown to have higher sensitivity and specificity. The difluoromethyl group (-CF₂H) has attracted considerable attention in the field of biochemistry due to its ability to mimic hydroxyl or thiol functional groups.

2,2-Difluoroacetamide is primarily used in pharmaceutical and agrochemicals. The presence of the difluoromethyl group makes it an important structural element in molecular design, capable of modulating chemical stability and biological activity. For example, fluorinated amides in pharmaceutical formulations can serve as biocompatible materials and bioactive compounds. 2,2-Difluoroacetamide can be used in reactions involving the parent functional group and the electron-withdrawing difluoromethyl group.

For example, it can undergo substitution reactions with acyl groups and water to generate complex fluorinated derivatives. Its high reactivity makes it an ideal starting material for introducing difluoromethyl groups into heterocycles and other nitrogen-containing skeletons. This compound is also used in biochemical research. Even small changes in electron distribution can significantly affect activity and selectivity, making these properties valuable in the design of enzyme inhibitors.

In short, 2,2-difluoroacetamide is an important fluorine-containing structural unit in biochemistry and medicinal chemistry. Its discovery and development highlight the crucial role of fluorine chemistry in constructing molecules with unique behaviors and properties, which have immeasurable value for both basic research and applied technologies.

Safety Information

Wear appropriate protective clothing, gloves, and eye/face protection.
If contact with eyes occurs, immediately flush with plenty of water and seek medical attention.
Irritating to eyes, respiratory system, and skin.

References

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Melting point	51.8 °C
boiling point	108.63 °C
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
solubility	DMSO (slightly soluble), water (slightly soluble)
form	Crystalline Powder
color	White to light beige
density	1.291±0.06 g/cm3
pKa	13.16±0.50