3009-97-0

Basic information

• Product Name: N-Phenylglycinonitrile
• Synonyms: N-PHENYLGLYCINONITRILE;1-anilinoacetonitrile;anilino-acetonitril;anilinoacetonitrile;n-(cyanomethyl)aniline;n-phenylglycinenitrile;phenylamino-acetonitril;phenylglycinenitrile
• CAS NO: 3009-97-0
• Molecular Formula: C₈H₈N₂
• Molecular Weight: 132.16
• EINECS: 221-129-0
• Mol File: 3009-97-0.mol
• Article Data: 33

Chemical Properties

• Melting Point: 40 °C
• Boiling Point: 234.08°C (rough estimate)
• Flash Point: 137.4 °C
• Appearance: Yellow/Crystalline Low Melting Solid
• Density: 1.1083 (rough estimate)
• Vapor Pressure: 0.000924mmHg at 25°C
• Refractive Index: 1.6013 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 1.28±0.50(Predicted)
• CAS DataBase Reference: N-Phenylglycinonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: N-Phenylglycinonitrile(3009-97-0)
• EPA Substance Registry System: N-Phenylglycinonitrile(3009-97-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-22
• Safety Statements: 36/37
• Hazardous Substances Data: 3009-97-0(Hazardous Substances Data)

Usage

Uses

N-Phenylglycinonitrile is a useful building block used in the preparation of purine derivatives with ability to inhibit protein kinases by competitive displacement of ATP.

InChI:InChI=1/C8H8N2/c9-6-7-10-8-4-2-1-3-5-8/h1-5,10H,7H2

Upstream product

• 107-14-2 chloroacetonitrile 
• 62-53-3 aniline 
• 107-16-4 glycolonitrile 
• 149-44-0 rongalite 
• 6011-14-9 2-aminoacetonitrile hydrochloride 
• 74-90-8 hydrogen cyanide 
• 91-78-1 1,3,5-triphenylhexahydro-1,3,5-triazine 
• 590-17-0 cyanomethyl bromide 
• 13314-99-3 N-(anilomethyl)succinimide 
• 151-50-8 potassium cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 103-01-5 N-Phenylglycine 
• 103-70-8 Formanilid 
• 22821-76-7 4-(methylsulfonyl)benzonitrile 

Downstream Products

• 135481-41-3 N-(2-cyanoethyl)-N-(cyanonmethyl)aniline 
• 22977-96-4 2-Chloro-N-cyanomethyl-4-nitro-N-phenyl-benzamide 
• 117679-34-2 2-(allyl(phenyl)amino)acetonitrile 
• 103-01-5 N-Phenylglycine 
• 76182-44-0 N-methoxycarbonylanilinobromoacetonitrile 
• 76182-46-2 α-(N-methoxycarbonylanilino)cinnamonitrile 
• 76182-51-9 cis-1-methoxycarbonyl-3-phenylindoline-2-carbonitrile 
• 76182-51-9 trans-1-methoxycarbonyl-3-phenylindoline-2-carbonitrile 
• 62423-82-9 N-(1-methyl-1,2⁽⁴⁾,5,6-tetrahydro-[1,2,4]triazin-3-ylmethyl)-aniline 
• 502767-60-4 ({4-cycloheptylamino-6-[((R)-1-ethyl-pyrrolidin-2-ylmethyl)-amino]-1,3,5-triazin-2-yl}-phenyl-amino)-acetonitrile 
• 502767-59-1 ({4-cycloheptylamino-6-[((S)-1-ethyl-pyrrolidin-2-ylmethyl)-amino]-1,3,5-triazin-2-yl}-phenyl-amino)-acetonitrile 
• 502766-65-6 [(4-(cycloheptylamino)-6-{[(1-ethyl-2-pyrrolidinyl)methyl]amino}-1,3,5-triazin-2-yl)(phenyl)amino]acetonitrile 
• 1425864-74-9 3-amino-1-phenylpyrazin-2(1H)-one 
• 1425865-07-1 2-methyl-8-phenyl-4H-pyrimido[1,2-a]pyrazine-4,9(8H)-dione 

Relevant articles and documents

Iron-catalyzed reductive strecker reaction

Strecker reaction is widely applied for the synthesis of amino acids from aldehydes, amines and cyanides. Herein, we report the FeI2-catalyzed reductive Strecker type reaction of formamides instead of aldehydes to produce amino acetonitriles. The challenging capture of carbinolamine intermediates by CN? was achieved via Fe catalysis. This approach afforded better yields than the use of Ir- or Rh-catalysts. The application ability of this methodology is demonstrated by 1) one-pot construction of (13C labeled) complex molecules from CO2 via amino acetonitrile intermediates and 2) convenient production of homologated carboxylic acids from aldehydes.

Dynamics in Catalytic Asymmetric Diastereoconvergent (3 + 2) Cycloadditions with Isomerizable Nitrones and α-Keto Ester Enolates

Reaction design in asymmetric catalysis has traditionally been predicated on a structurally robust scaffold in both substrates and catalysts, to reduce the number of possible diastereomeric transition states. Herein, we present the stereochemical dynamics in the Ni(II)-catalyzed diastereoconvergent (3 + 2) cycloadditions of isomerizable nitrile-conjugated nitrones with α-keto ester enolates. Even in the presence of multiple equilibrating species, the catalytic protocol displays a wide substrate scope to access a range of CN-containing building blocks bearing adjacent stereocenters with high enantio- and diastereoselectivities. Our computational investigations suggest that the enantioselectivity is governed in the deprotonation process to form (Z)-Ni-enolates, while the unique syn addition is mainly controlled by weak noncovalent bonding interactions between the nitrone and ligand.

Decarboxylative Cyanation of Aliphatic Carboxylic Acids via Visible-Light Flavin Photocatalysis

An operationally simple method is disclosed for the decarboxylative cyanation of aliphatic carboxylic acids at room temperature. Riboflavin tetraacetate, which is an inexpensive organic photocatalyst, promotes the oxidation of carboxylic acids upon visible-light activation. After decarboxylation, the generated radicals are trapped by TsCN, yielding the desired nitriles without any further additive, in a redox-neutral process. Importantly, this protocol can be adapted to flow conditions.