359-12-6

Basic information

• Product Name: DIFLUOROACETONITRILE
• Synonyms: 2,2-difluoroethanenitrile;Difluoromethyl cyanide, 2,2-Difluoroethanonitrile;DIFLUOROACETONITRILE;2,2-difluoroacetonitrile
• CAS NO: 359-12-6
• Molecular Formula: C₂HF₂N
• Molecular Weight: 77.03
• Product Categories: 2,2-bis(fluoranyl)ethanenitrile
• Mol File: 359-12-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 0°C
• Boiling Point: 0°C
• Flash Point: 0°C
• Appearance: /
• Density: 1.113
• Vapor Pressure: 1900mmHg at 25°C
• Refractive Index: 1.277
• CAS DataBase Reference: DIFLUOROACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: DIFLUOROACETONITRILE(359-12-6)
• EPA Substance Registry System: DIFLUOROACETONITRILE(359-12-6)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 359-12-6(Hazardous Substances Data)

Usage

General Description

Difluoroacetonitrile is a colorless, nonflammable liquid that has a pungent odor. This chemical compound, also known as 2,2-difluoracetonitrile, is often used in the production of pharmaceuticals and other organic compounds due to its chemical properties. Its molecular formula is C2H1F2N and it normally exists in a liquid state at room temperature. Given its usage in various chemical reactions, it's important to handle it with care. The safety data sheet of this compound indicates that it may cause burns and eye damage, and it is harmful if inhaled. It is not widely found in nature and is typically synthesized in laboratories.

InChI:InChI=1/C2HF2N/c3-2(4)1-5/h2H

Upstream product

• 75-05-8 acetonitrile 
• 773837-37-9 sodium cyanide 
• 75-45-6 Chlorodifluoromethane 
• 359-38-6 2,2-difluoroacetamide 

Downstream Products

• 155094-61-4 N-Ethyl-N-phenyldifluoroacetamide 
• 71025-65-5 1,1-difluoro-3-phenyl-2-aminopropane 
• 14978-91-7 cis-1,2-difluorovinylene dicyanide 
• 41809-92-1 Difluorfumaronitril 
• 2218-52-2 sodium salt of difluoroacetate 
• 454-31-9 ethyl difluoroacetate 
• 1599437-72-5 (Z)-diphenyl (2,2-difluoroethanimidoyl)phosphonate 
• 1599437-72-5 (E)-diphenyl (2,2-difluoroethanimidoyl)phosphonate 
• 395-01-7 2,2-difluoro-1-phenylethanone 
• 1335113-25-1 1-(2,5-dimethoxyphenyl)-2,2-difluoroethanone 
• 1335113-26-2 1-(2,5-dimethylphenyl)-2,2-difluoroethanone 
• 1335113-22-8 1-(5-chloro-2-methoxyphenyl)-2,2-difluoroethanone 
• 1335113-27-3 2,2-difluoro-1-(4-hydroxy-3,5-dimethylphenyl)ethanone 

Relevant articles and documents

METHOD FOR PREPARING DIFLUOROACETONITRILE AND THE DERIVATIVES THEREOF

The present invention relates to a method for preparing difluoracetonitrile and the derivatives thereof. The method for preparing difluoroacetonitrile according to the invention is characterized in that it includes reacting halogenodifluoromethane and a source of cyanide anions in an alkaline medium. The invention also relates to the use of difluoroacetonitrile as an intermediate in the manufacture of difluoroacetic acid and the salts, esters, or amide thereof

Application of the goldilocks effect to the design of potent and selective inhibitors of phenylethanolamine N-methyltransferase: Balancing pKa and steric effects in the optimization of 3-methyl-1,2,3,4- tetrahydroisoquinoline inhibitors by β-fluorination

3-Methyl-1,2,3,4-tetrahydroisoquinolines (3-methyl-THIQs) are potent inhibitors of phenylethanolamine N-methyltransferase (PNMT), but are not selective due to significant affinity for the α2-adrenoceptor. Fluorination of the methyl group lowers the pKa of the THIQ amine from 9.53 (CH3) to 7.88 (CH2F), 6.42 (CHF2), and 4.88 (CF3). This decrease in pKa results in a reduction in affinity for the α2-adrenoceptor. However, increased fluorination also results in a reduction in PNMT inhibitory potency, apparently due to steric and electrostatic factors. Biochemical evaluation of a series of 3-fluoromethyl-THIQs and 3-trifluoromethyl-THIQs showed that the former were highly potent inhibitors of PNMT, but were often nonselective due to significant affinity for the α2-adrenoceptor, while the latter were devoid of α2-adrenoceptor affinity, but also lost potency at PNMT. 3-Difluoromethyl-7-substituted-THIQs have the proper balance of both steric and pKa properties and thus have enhanced selectivity versus the corresponding 3-fluoromethyl-7-substituted-THIQs and enhanced PNMT inhibitory potency versus the corresponding 3-trifluoromethyl-7-substituted- THIQs. Using the "Goldilocks Effect" analogy, the 3-fluoromethyl-THIQs are too potent (too hot) at the α2-adrenoceptor and the 3-trifluoromethyl-THIQs are not potent enough (too cold) at PNMT, but the 3-difluoromethyl-THIQs are just right. They are both potent inhibitors of PNMT and highly selective due to low affinity for the α2- adrenoceptor. This seems to be the first successful use of the β-fluorination of aliphatic amines to impart selectivity to a pharmacological agent while maintaining potency at the site of interest.