70591-20-7

Basic information

• Product Name: N-(Diphenylmethylene)aminoacetonitrile
• Synonyms: LABOTEST-BB LT00159830;N-(DIPHENYLMETHYLENE)AMINOACETONITRILE;[(Diphenylmethylene)amino]methyl cyanide;(Benzhydrylideneamino)acetonitrile;(Diphenylmethyleneamino)acetonitrile;[(Benzhydrylidene)amino]acetonitrile;[(Diphenylmethylene)amino]acetonitrile;2-[(Diphenylmethylene)amino]acetonitrile
• CAS NO: 70591-20-7
• Molecular Formula: C₁₅H₁₂N₂
• Molecular Weight: 220.27
• EINECS: 1533716-785-6
• Product Categories: C10 to C27;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 70591-20-7.mol
• Article Data: 19

Chemical Properties

• Melting Point: 83-86 °C
• Boiling Point: 351.21°C (rough estimate)
• Flash Point: 161.617 °C
• Appearance: White to yellow or slightly gray/Powder or Crystals
• Density: 1.1405 (rough estimate)
• Vapor Pressure: 6.95E-05mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: 0-6°C
• Solubility: 95% ethanol: soluble50mg/mL, clear, colorless to faintly yellow
• PKA: 1.03±0.50(Predicted)
• CAS DataBase Reference: N-(Diphenylmethylene)aminoacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: N-(Diphenylmethylene)aminoacetonitrile(70591-20-7)
• EPA Substance Registry System: N-(Diphenylmethylene)aminoacetonitrile(70591-20-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• Hazardous Substances Data: 70591-20-7(Hazardous Substances Data)

Usage

Chemical Properties

white to slightly grey crystals or cryst. powder

Uses

N-(Diphenylmethylene)aminoacetonitrile is a reagent for?α-amino acids using transition metal catalysis. It can also be used to synthesize Cathepsin B inhibitors.

InChI:InChI=1/C15H12N2/c16-11-12-17-15(13-7-3-1-4-8-13)14-9-5-2-6-10-14/h1-10H,12H2

Synthetic route

Benzophenone imine (1013-88-3) + 2-aminoacetonitrile hydrochloride (6011-14-9) → N-(diphenylmethylene)aminoacetonitrile (70591-20-7)

Conditions	Yield
In dichloromethane for 24h; Ambient temperature;	93%
With acetic acid In acetonitrile for 16h; Heating;
In dichloromethane at 20℃; for 120h;

benzophenone (119-61-9) + 2-aminoacetonitrile hydrochloride (6011-14-9) → N-(diphenylmethylene)aminoacetonitrile (70591-20-7)

Conditions	Yield
With titanium tetrachloride; triethylamine In N,N-dimethyl-formamide; pentane at 35 - 40℃; for 1h;	83%
With titanium tetrachloride; triethylamine In N,N-dimethyl-formamide
In dichloromethane at 20℃; Schlenk technique; Inert atmosphere;

diphenylmethanone O-benzoyl oxime (3362-33-2) + acetonitrile (75-05-8) → N-(diphenylmethylene)aminoacetonitrile (70591-20-7)

Conditions	Yield
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate at 20 - 22℃; for 2h; Inert atmosphere; Irradiation; Sealed tube;	73%

sodium cyanide (143-33-9) + <(Diphenylmethylen)aminomethyl>trimethylammoniumiodid (69414-68-2) → N-(diphenylmethylene)aminoacetonitrile (70591-20-7)

Conditions	Yield
In water for 2h; Heating;	42%

N-(diphenylmethylene)aminoacetonitrile (146495-24-1) → N-(diphenylmethylene)aminoacetonitrile (70591-20-7) + [(E)-Benzhydrylimino]-acetonitrile

Conditions	Yield
With sodium hypochlorite In 1,4-dioxane; water at 20℃; for 1h; Chlorination; dehydrochlorination; Title compound not separated from byproducts;
With sodium hypochlorite In water at 10℃; for 2.33333h; Dehydrogenation;	A 60 % Spectr. B 25 % Spectr.

N-Diphenylmethylen-N',N'-(dimethyl)methylendiamin (69414-67-1) → N-(diphenylmethylene)aminoacetonitrile (70591-20-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / ethanol / 2 h 2: 42 percent / H2O / 2 h / Heating View Scheme

Benzophenone imine (1013-88-3) + cyanomethylamine sulfate (151-63-3) → N-(diphenylmethylene)aminoacetonitrile (70591-20-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 48h;

Benzophenone oxime (574-66-3) → N-(diphenylmethylene)aminoacetonitrile (70591-20-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 0 - 20 °C 2: [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate / 2 h / 20 - 22 °C / Inert atmosphere; Irradiation; Sealed tube View Scheme

N-(diphenylmethylene)aminoacetonitrile (70591-20-7) + 2-ethoxycarbonylethyl halide → ethyl 4-cyano-4-[(diphenylmethylene)amino]butanoate (82680-27-1)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane	99%

4-methyl-chalcone (4224-87-7) + N-(diphenylmethylene)aminoacetonitrile (70591-20-7) → C31H26N2O

Conditions	Yield
In water	99%

di-tert-butyl-diazodicarboxylate (870-50-8) + N-(diphenylmethylene)aminoacetonitrile (70591-20-7) → (2R)-di-tert-butyl 1-{1-[(diphenylmethylene)amino]-2-cyano}hydrazine-1,2-dicarboxylate + C25H30N4O4

Conditions	Yield
With C62H61BrN4O2Pd; silver(I) acetylacetonate In tetrahydrofuran at -40℃; for 18h; enantioselective reaction;	A 99% B n/a

N-(diphenylmethylene)aminoacetonitrile (70591-20-7) + Carbonic acid methyl ester (Z)-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl ester → (Z)-2-(Benzhydrylidene-amino)-6-(tetrahydro-pyran-2-yloxy)-hex-4-enenitrile

Conditions	Yield
With palladium	98%

N-(diphenylmethylene)aminoacetonitrile (70591-20-7) + benzalacetophenone (94-41-7) → C30H24N2O

Conditions	Yield
In water	98%

N-(diphenylmethylene)aminoacetonitrile (70591-20-7) + C-phenyl-N-methylnitrone (3376-23-6, 7372-59-0, 59862-60-1) + Triethylsilyl trifluoromethanesulfonate (79271-56-0) → 2-((diphenylmethylene)amino)-3-(methyl((triethylsilyl)oxy)amino)-3-phenylpropanenitrile

Conditions	Yield
With triethylamine In 1,2-dichloro-ethane at -30℃; for 0.5h; Inert atmosphere;	98%

(E)-N-benzylidenepyridine-2-sulfonamide (721453-65-2) + N-(diphenylmethylene)aminoacetonitrile (70591-20-7) → (2R,3S)-2-amino-3-phenyl-3-(2-pyridinesulfonyl)aminopropionitrile

Conditions	Yield
Stage #1: (E)-N-benzylidenepyridine-2-sulfonamide; N-(diphenylmethylene)aminoacetonitrile With Trimethylsilanol; C50H37BrN4O2Pd; silver(I) acetylacetonate In tetrahydrofuran at -60℃; for 24h; Stage #2: With hydrogenchloride In water	95%

N-(diphenylmethylene)aminoacetonitrile (70591-20-7) + 1-(t-butyldimethylsilyl)-2-phenylethane-1,2-dione → 2-(3-((tert-butyldimethylsilyl)oxy)-4-oxo-2,2,3-triphenylazetidin-1-yl)acetonitrile

Conditions	Yield
In acetonitrile at 20℃; for 1.5h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation;	94%

N-(diphenylmethylene)aminoacetonitrile (70591-20-7) + methyl iodide (74-88-4) → 2-(diphenylmethylene)amino-2-methylpropanenitrile

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 0 - 20℃; for 17h; Temperature;	93.6%

N-(diphenylmethylene)aminoacetonitrile (70591-20-7) + 1,3-chlorobromopropane (109-70-6) → 5-chloro-2-[(N-diphenylmethylene)amino]pentanenitrile (211450-07-6)

Conditions	Yield
Stage #1: N-(diphenylmethylene)aminoacetonitrile With sodium hydride In tetrahydrofuran at 20℃; Metallation; Stage #2: 1.3-chlorobromopropane In tetrahydrofuran at 20℃; for 1h; Substitution;	93.5%

N-(diphenylmethylene)aminoacetonitrile (70591-20-7) + p-nitrobenzyl halide → 2-[(diphenylmethylene)amino]-3-(4-nitrophenyl)propanenitrile (488152-04-1)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane	93%

N-(diphenylmethylene)aminoacetonitrile (70591-20-7) + methyl iodide (74-88-4) → C16H14N2 (70591-21-8)

Conditions	Yield
Stage #1: N-(diphenylmethylene)aminoacetonitrile With n-butyllithium In tetrahydrofuran; hexane at -90 - 20℃; Metallation; Stage #2: methyl iodide In tetrahydrofuran; hexane at 20℃; Methylation;	92%

N-(diphenylmethylene)aminoacetonitrile (70591-20-7) + 3-chloropropyl halide → 5-chloro-2-[(N-diphenylmethylene)amino]pentanenitrile (211450-07-6)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane	92%

N-(diphenylmethylene)aminoacetonitrile (70591-20-7) + 4-Fluorobenzyl bromide (459-46-1) → 2-((diphenylmethylene)amino)-3-(4-fluorophenyl)propanenitrile (1289648-80-1)

Conditions	Yield
With sodium hydroxide; benzyltrimethylammonium chloride In dichloromethane for 18h;	92%
With benzyltrimethylammonium chloride; sodium hydroxide In dichloromethane; water for 18h;	92%
With benzyltrimethylammonium chloride; sodium hydroxide In water for 18h;	92%

N-(diphenylmethylene)aminoacetonitrile (70591-20-7) + diethyl <5-(bromomethyl)<1,1'-biphenyl>-3-yl>methylphosphonate (118077-11-5) → {5-[2-(Benzhydrylidene-amino)-2-cyano-ethyl]-biphenyl-3-ylmethyl}-phosphonic acid diethyl ester (142184-03-0)

Conditions	Yield
With sodium hydroxide; benzyltri(n-butyl)ammonium chloride In toluene for 24h; Ambient temperature;	91%

N-(diphenylmethylene)aminoacetonitrile (70591-20-7) + dimethyl [1-(methoxycarbonyloxy)-2-propenyl] phosphonate (180294-79-5) → Triphenylphosphine oxide (791-28-6) + [(Z)-4-(Benzhydrylidene-amino)-4-cyano-but-1-enyl]-phosphonic acid dimethyl ester (193805-96-8) + [(E)-4-(Benzhydrylidene-amino)-4-cyano-but-1-enyl]-phosphonic acid dimethyl ester

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 2.5h;	A n/a B 91% C n/a

N-(diphenylmethylene)aminoacetonitrile (70591-20-7) + methyl (E)-4-bromo-4-methylpenten-2-oate (70335-50-1) → methyl 4-amino-5-benzhydrylideneamino-3,3-dimethylcyclopenta-1,4-dienecarboxylate (133618-79-8)

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran	90%

N-(diphenylmethylene)aminoacetonitrile (70591-20-7) + Methyl cinnamate (103-26-4) → methyl 4-cyano-4--3-phenylbutanoate

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In toluene at 20℃; for 5h;	90%

N-(diphenylmethylene)aminoacetonitrile (70591-20-7) + (2R)-N-triphenylmethyl-3-iodoalanine methyl ester (181637-40-1) → (S)-4-(Benzhydrylidene-amino)-4-cyano-2-(trityl-amino)-butyric acid methyl ester + methyl (2S)-N-tritylaziridine-2-carboxylate (75154-68-6)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water at 20℃; for 4h; Substitution; cyclization;	A 90% B 8%

1-bromo-butane (109-65-9) + N-(diphenylmethylene)aminoacetonitrile (70591-20-7) → 2-(Benzhydrylidene-amino)-hexanenitrile (137283-20-6)

Conditions	Yield
Stage #1: N-(diphenylmethylene)aminoacetonitrile With n-butyllithium In tetrahydrofuran; hexane at -90 - 20℃; Metallation; Stage #2: 1-bromo-butane In tetrahydrofuran; hexane at 20℃; Alkylation;	90%

Upstream product

• 1013-88-3 Benzophenone imine 
• 6011-14-9 2-aminoacetonitrile hydrochloride 
• 143-33-9 sodium cyanide 
• 69414-68-2 <(Diphenylmethylen)aminomethyl>trimethylammoniumiodid 
• 119-61-9 benzophenone 
• 146495-24-1 N-(diphenylmethylene)aminoacetonitrile 
• 69414-67-1 N-Diphenylmethylen-N',N'-(dimethyl)methylendiamin 
• 151-63-3 cyanomethylamine sulfate 
• 3362-33-2 diphenylmethanone O-benzoyl oxime 
• 75-05-8 acetonitrile 
• 574-66-3 Benzophenone oxime 

Downstream Products

• 89985-89-7 1-<(Diphenylmethylene)-amino>-1-cyclopentanecarbonitrile 
• 81167-32-0 2-(N-diphenylmethylene)amino-3-(1H-indol-3-yl)propionitrile 
• 220505-13-5 2-[N-(diphenylmethylene)amino]-3-(²H₃-methyl),4-(²H₃)-butyronitrile 
• 129409-81-0 3-cyano-1,1,4-triphenyl-2-aza-1,3-butadiene 
• 75-04-7 ethylamine 
• 137283-21-7 4-Benzenesulfinyl-2-(benzhydrylidene-amino)-butyronitrile 
• 139616-36-7 2-(Benzhydrylidene-amino)-3-phenylamino-3-p-tolyl-propionitrile 
• 135630-83-0 2-(Benzhydrylidene-amino)-pent-4-enenitrile 
• 119825-46-6 2(diphenyl methylene)amino-4-methyl-4-pentenonitrile 
• 133618-77-6 methyl 2-<(benzhydrylideneamino cyano)methyl>-4-methylpent-3-enoate 
• 133618-79-8 methyl 4-amino-5-benzhydrylideneamino-3,3-dimethylcyclopenta-1,4-dienecarboxylate 
• 87042-98-6 2-(Benzhydrylidene-amino)-3-pentabromophenyl-propionitrile 
• 119825-55-7 2-(diphenyl methylene)amino-4-hexenonitrile 
• 119825-54-6 2(diphenyl methylene)amino-3-methyl-4-pentenonitrile 

Relevant articles and documents

Visible-Light-Induced Cycloaddition of α-Ketoacylsilanes with Imines: Facile Access to β-Lactams

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