218449-30-0

Basic information

• Product Name: 2-aMino-2-(3,4-difluorophenyl)acetonitrile
• Synonyms: 2-aMino-2-(3,4-difluorophenyl)acetonitrile
• CAS NO: 218449-30-0
• Molecular Formula: C₈H₆F₂N₂
• Molecular Weight: 168.1434464
• Mol File: 218449-30-0.mol

Chemical Properties

• Boiling Point: 237.4±40.0 °C(Predicted)
• Appearance: /
• Density: 1.308±0.06 g/cm3(Predicted)
• PKA: 4.72±0.10(Predicted)
• CAS DataBase Reference: 2-aMino-2-(3,4-difluorophenyl)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-aMino-2-(3,4-difluorophenyl)acetonitrile(218449-30-0)
• EPA Substance Registry System: 2-aMino-2-(3,4-difluorophenyl)acetonitrile(218449-30-0)

Safety Data

• Hazardous Substances Data: 218449-30-0(Hazardous Substances Data)

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 34036-07-2 3,4 difluorobenzaldehyde 
• 72235-53-1 3,4-difluorobenzylamine 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 

Downstream Products

• 225641-94-1 DL-(3,4-difluorophenyl)glycine 
• 218451-28-6 (+)-3-(3-(4-cyano-4-(2,4-dichloro)phenylpiperidin-1-yl)propyl)aminocarbonyl-4-(3,4-difluorophenyl)-2-oxazolidinone 
• 218451-40-2 (+)-3-(3-(4-Aminocarbonyl-4-(4-chloro)phenylpiperidin-1-yl)-propyl)aminocarbonyl-4-(3,4-difluoro)phenyl-2-oxazolidinone 
• 277295-97-3 1-(3,4-difluorophenyl)-2-methyl-2-hydroxypropylamine 
• 218449-37-7 4-(3,4-difluorophenyl)-2-oxo-oxazolidine-3-carboxylic acid-4-nitro-phenyl ester 
• 218450-42-1 4-(3,5-difluorophenyl)-5,5-dimethyl-2-oxo-oxazolidine 
• 218449-35-5 [1-(3,4-difluorophenyl)-2-hydroxy-ethyl]-carbamic acid-tert-butyl ester 
• 225641-91-8 4-(3,4-difluorophenyl)-2-oxazolidinone 
• 277295-93-9 2-amino-2-(3,4-difluorophenyl)-ethanol 
• 218449-31-1 amino-(3,4-difluorophenyl)-acetic acid methyl ester 

Relevant articles and documents

Facile Access to 1,4-Disubstituted Pyrrolo[1,2- a ]pyrazines from α-Aminoacetonitriles

An efficient and practical synthetic protocol for the synthesis of 1,4-disubstituted pyrrolo[1,2- a ]pyrazine derivatives is described that originates from α-substituted pyrroloacetonitriles which, in turn, are readily available from aryl and alkyl aldehydes. The α-pyrroloacetonitriles were subjected to a Friedel-Crafts acylation with methyl chlorooxoacetate followed by reduction of the nitrile group under Pd-catalyzed hydrogenation conditions and finally aromatization with DDQ leading to the desired pyrrolo[1,2- a ]pyrazine derivatives. This method was generalized and successfully applied to various aryl, heteroaryl, and alkyl substrates. The developed protocol provides direct and convenient access to 1,4-disubstituted ring systems in moderate to good overall yields (51-68percent) without the need for purification of the intermediates. Further functionalization via the stepwise halogenation (bromination, iodination) and nitration was also demonstrated. In addition, the potential of the ester functionality for elaboration was demonstrated by manipulating into heterocyclic ring systems, exemplified by conversion into benzoxazole derivatives.

Flow synthesis of fluorinated α-amino acids

Fluorinated α-amino acids are versatile compounds that are used for many purposes in medicinal and biochemistry. However, their synthesis remains a significant hurdle, often requiring multiple steps, multiple protecting groups, and/or the use of highly toxic reagents. These challenges have limited the application of fluorinated α-amino acids. A convenient, protecting-group-free and semi-continuous process for the synthesis of racemic fluorinated α-amino acids from fluorinated amines is described. Following a singlet-oxygen-driven photooxidative cyanation, an acid-mediated hydrolysis of the intermediate α-amino nitrile yields the desired α-amino acid. Aliphatic, benzylic, and homobenzylic residues with different fluorination degrees are tolerated, providing good overall yields (50-67?%). This semi-continuous process is particularly advantageous for an aliphatic amine, the intermediate α-amino nitrile of which decomposes upon isolation. An efficient, semi-continuous, and protecting-group-free method for the synthesis of fluorinated α-amino acids from the corresponding amines has been developed. A low temperature photooxidative cyanation of benzylic and aliphatic amines provided α-amino nitriles with varying fluorination patterns. These unstable intermediates were trapped with an acid-mediated hydrolysis with good overall yields.

Discovery of novel spiro-piperidine derivatives as highly potent and selective melanin-concentrating hormone 1 receptor antagonists

Optimization of high-throughput screening hit 1a led to the identification of a novel spiro-piperidine class of melanin-concentrating hormone 1 receptor (MCH-1R) antagonists. Compound 3c was identified as a highly potent and selective MCH-1R antagonist, which has an IC50 value of 0.09 nM at hMCH-1R. The synthesis and structure-activity relationships of the novel spiro-piperidine MCH-1R antagonists are described.

Development of a new α-aminonitrile synthesis

α-Aminonitriles are prepared upon reaction of aryl carboxaldehydes with LiHMDS and acetone cyanohydrin. This new method provides a general route to the synthesis of various substituted α-aminoarylacetonitriles in high yield and purity, and avoids the use of the highly toxic cyanide salts.

SUBSTITUTED ANILINIC PIPERIDINES AS MCH SELECTIVE ANTAGONISTS

This invention is directed to compounds which are selective antagonists for melanin concentrating hormone-1 (MCH1) receptors. The invention provides a pharmaceutical composition comprising a therapeutically effective amount of the compound of the invention and a pharmaceutically acceptable carrier. This invention provides a pharmaceutical composition made by combining a therepeutically effective amount of the compound of this invention and a pharmaceutically acceptable carrier. This invention further provides a process for making a pharmaceutical composition comprising combining a therapeutically effective amount of the compound of the invention and a pharmaceutically acceptable carrier.

MORPHOLINONE AND MORPHOLINE DERIVATIVES AND USES THEREOF

This invention is directed to morpholinone and morpholine derivatives which are selective antagonists for human α 1a receptors. This invention is also related to uses of these compounds for lowering intraocular pressure, inhibiting cholesterol synthesis, relaxing lower urinary tract tissue, the treatment of benign prostatic hyperplasia, impotency, cardiac arrhythmia, sympathetic mediated pain, migraine, and for the treatment of any disease where the antagonism of the α 1a receptor may be useful. The invention further provides a pharmaceutical composition comprising a therapeutically effective amount of the above-defined compounds and a pharmaceutically acceptable carrier.

Oxazolidinones as alpha 1A receptor antagonists

This invention is directed to oxazolidinone compounds which are selective antagonists for human alpha 1A receptors. This invention is also related to uses of these compounds for lowering intraocular pressure, inhibiting cholesterol synthesis, relaxing lower urinary tract tissue, the treatment of benign prostatic hyperplasia, impotency, cardiac arrhythmia and for the treatment of any disease where the antagonism of the alpha 1A receptor may be useful. The invention further provides a pharmaceutical composition comprising a therapeutically effective amount of the above-defined compounds and a pharmaceutically acceptable carrier.