5652-84-6

Basic information

• Product Name: Methyl N-cyanoethanimideate
• Synonyms: methyln-cyanoethanimidate;n-cyano-acetimidicacimethylester;n-cyano-ethanimidicacimethylester;N-CYANOETHANIMIDIC METHYL ESTER;METHYL N-CYANOACETIMIDATE;METHYL N-CYANOACETOIMIDATE;methyl n-cyanoethanimideate;N-CYANO METHYL ACETIMIDATE
• CAS NO: 5652-84-6
• Molecular Formula: C₄H₆N₂O
• Molecular Weight: 98.1
• Mol File: 5652-84-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 107.7 °C at 760 mmHg
• Flash Point: 18.9 °C
• Appearance: Colourless transparent liquid
• Density: 0.95 g/cm³
• Vapor Pressure: 26.8mmHg at 25°C
• Refractive Index: 1.438
• PKA: -3.10±0.50(Predicted)
• CAS DataBase Reference: Methyl N-cyanoethanimideate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl N-cyanoethanimideate(5652-84-6)
• EPA Substance Registry System: Methyl N-cyanoethanimideate(5652-84-6)

Safety Data

• Hazardous Substances Data: 5652-84-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C4H6N2O/c1-4(7-2)6-3-5/h1-2H3/b6-4+

Synthetic route

CYANAMID (420-04-2) + methyl acetimidate hydrochloride (14777-27-6) → methyl N-cyanoacetimidate (5652-84-6)

Conditions	Yield
In methanol

methanol (67-56-1) + (N-Cyano)diazoethanimin (15328-19-5) → methyl N-cyanoacetimidate (5652-84-6)

Conditions	Yield
Irradiation;

2,2-difluorethylamine (430-67-1) + methyl N-cyanoacetimidate (5652-84-6) → N'-cyano-N-(2,2-difluoroethyl)ethanimidamide (1003859-01-5)

Conditions	Yield
In methanol at 20℃; for 3h;	98%

2-chloro-5-(chloromethyl)pyridine (70258-18-3) + methyl N-cyanoacetimidate (5652-84-6) + methylamine (74-89-5) → acetamiprid

Conditions	Yield
Stage #1: 2-chloro-5-(chloromethyl)pyridine; methylamine In toluene at 3 - 25℃; for 6h; Large scale; Stage #2: methyl N-cyanoacetimidate With ethanol In toluene at 35℃; for 4h; Temperature; Large scale;	93%

methyl N-cyanoacetimidate (5652-84-6) + phenylhydrazine (100-63-0) → 3-methyl-1-phenyl-1H-1,2,4-triazol-5-amine (68557-26-6)

Conditions	Yield
In methanol for 4h; Reflux;	83%

methyl N-cyanoacetimidate (5652-84-6) + 5-(aminomethyl)-2-chloropyridine (97004-04-1) → acetamiprid-N-desmethyl (135410-03-6, 190604-92-3)

Conditions	Yield
In methanol at 20℃; for 3h;	52%

methyl N-cyanoacetimidate (5652-84-6) + 2-pyridinecarboxamide hydrochloride → 4-methyl-6-(pyridin-2-yl)-1,3,5-triazin-2-amine (657411-85-3)

Conditions	Yield
Stage #1: picolinamide hydrochloride With sodium methylate In methanol at 20℃; for 0.333333h; Stage #2: methyl N-cyanoacetimidate In methanol at 20℃; for 12h;	50%

methyl N-cyanoacetimidate (5652-84-6) + N-[(6-chloropyridin-3-yl)methyl]-3-fluoropropane-1-amine (1003859-15-1) → N-[(6-chloropyridin-3-yl)methyl]-N'-cyano-N-(3-fluoropropyl)ethanimidamide (1003858-98-7)

Conditions	Yield
In methanol at 20℃; for 96h;	8%

2-cyanoethylamine (151-18-8) + methyl N-cyanoacetimidate (5652-84-6) → N'-Cyano-N-(2-cyanoethyl)acetamidin (56563-05-4)

Conditions	Yield
In isopropyl alcohol

N-(2-cyanoethyl)-N-methylamine (693-05-0) + methyl N-cyanoacetimidate (5652-84-6) → C7H10N4

Conditions	Yield
In isopropyl alcohol

methyl N-cyanoacetimidate (5652-84-6) → N-methyl cyanoacetamide (87718-98-7)

Conditions	Yield
at 160 - 165℃;

methyl N-cyanoacetimidate (5652-84-6) → N-cyano-acetamidine (56563-07-6)

Conditions	Yield
With ammonia In methanol

methyl N-cyanoacetimidate (5652-84-6) + aniline (62-53-3) → N'-Phenyl-N-cyano-acetamidin (57292-74-7)

Conditions	Yield
In ethanol

methyl N-cyanoacetimidate (5652-84-6) + (3S,4R)-4-Amino-3-hydroxy-2,2-bis-methoxymethyl-chroman-6-carbonitrile (169102-78-7) → C17H20N4O4

Conditions	Yield
In methanol at 50 - 70℃; for 1h;

5(S)-aminomethyl-3-[4-(1-cyanocyclopropan-1-yl)phenyl]oxazolidin-2-one (543682-79-7) + methyl N-cyanoacetimidate (5652-84-6) → N'-cyano N-[5(S)-3-[4-(1-cyanocyclopropan-1-yl)phenyl]-2-oxooxazolidin-5-ylmethyl]acetamidine

Conditions	Yield
In tetrahydrofuran; methanol at 20℃; for 24h;

N-[5(S)-3-[4-[(1α,5α,6α)-6-amino-3-azabicyclo[3.1.0]hexan-3-yl]-3,5-difluorophenyl]-2-oxooxazolidin-5-ylmethyl]acetamide + methyl N-cyanoacetimidate (5652-84-6) → N-[5(S)-3-[4-[(1α,5α,6α)-6-[N-Cyano-1-iminoethyl)amino]-3-azabicyclo[3.1.0]hexan-3-yl]-3.5-difluorophenyl]-2-oxooxazolidin-5-ylmethylacetamide + N-[5(S)-3-[4-[(1α,5α,6α)-6-[(N-cyano-1-iminoethyl)amino]-3-azabicyclo[3.1.0]hexan-3-yl]-3,5-difluorophenyl]-2-oxooxazolidin-5-ylmethyl]acetamide (504437-53-0)

Conditions	Yield
In methanol

1-[5-cyclopropyl-1-(piperidin-4-yl)-1H-pyrazole-4-carbonyl]-[(S)-3-(2-trifluoromethylphenyl)]pyrrolidine hydrochloride + methyl N-cyanoacetimidate (5652-84-6) → 1-{1-[1-(1-cyanoiminoethyl)piperidin-4-yl]-5-cyclopropyl-1H-pyrazole-4-carbonyl}-3-[(S)-(2-trifluoromethylphenyl)]pyrrolidine

Conditions	Yield
With triethylamine In chloroform at 20 - 45℃; for 2.5h;

1-[5-cyclopropyl-1-(piperidin-4-yl)-1H-pyrazole-4-carbonyl]-[(S)-3-(2-trifluoromethylphenyl)]pyrrolidine hydrochloride + methyl N-cyanoacetimidate (5652-84-6) → 1-{1-[1-(1-cyanoiminoethyl)piperidin-4-yl]-5-cyclopropyl-1H-pyrazole-4-carbonyl}-[(S)-3-(2-trifluoromethylphenyl)]pyrrolidine (916829-30-6)

Conditions	Yield
With triethylamine In chloroform at 20 - 45℃; for 4h;

N-[5(S)-3-[4-[(1α,5α6β)-(6-cyano-3-azabicyclo[3.1.0]hexan-6-yl)]phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide hydrochloride + methyl N-cyanoacetimidate (5652-84-6) → N-[5(S)-3-[4-[(1α,5α6β)-(6-cyano-3-(N-cyano-1-iminoethyl)-3-azabicyclo[3.1.0]hexan-6-yl)]phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide

Conditions	Yield
Stage #1: N-[5(S)-3-[4-[(1α,5α6β)-(6-cyano-3-azabicyclo[3.1.0]hexan-6-yl)]phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide hydrochloride With N-ethyl-N,N-diisopropylamine In methanol at 20℃; for 0.333333h; Stage #2: methyl N-cyanoacetimidate In methanol at 20℃; for 48h;

2,6-Diaminopyridine (141-86-6) + methyl N-cyanoacetimidate (5652-84-6) → N-Cyano-N'-(6-amino-2-pyridyl)acetamidine (38713-78-9)

Conditions	Yield
In 1,2-dimethoxyethane at 20℃; for 24h; Inert atmosphere;

1-Chlorooctane (111-85-3) + methyl N-cyanoacetimidate (5652-84-6) + bis(trimethylsilyl)carbodi-imide (1000-70-0) → 2-amino-4-methyl-6-octyl-1,3,5-triazine

Conditions	Yield
Stage #1: n-chlorooctane With magnesium In diethyl ether at 35℃; Stage #2: bis(trimethylsilyl)carbodi-imide at 35℃; for 18h; Stage #3: methyl N-cyanoacetimidate Further stages;

Upstream product

• 1445-45-0 Trimethyl orthoacetate 
• 420-04-2 CYANAMID 
• 2742-27-0 1-[14C]-acetic anhydride 
• 67-56-1 methanol 
• 15328-19-5 (N-Cyano)diazoethanimin 
• 14777-27-6 methyl acetimidate hydrochloride 

Downstream Products

• 23945-47-3 2-amino-4-methyl-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile 
• 504437-53-0 N-[5(S)-3-[4-[(1α,5α,6α)-6-[(N-cyano-1-iminoethyl)amino]-3-azabicyclo[3.1.0]hexan-3-yl]-3,5-difluorophenyl]-2-oxooxazolidin-5-ylmethyl]acetamide 
• 68557-26-6 3-methyl-1-phenyl-1H-1,2,4-triazol-5-amine 
• 135410-03-6 acetamiprid-N-desmethyl 
• 916829-30-6 1-{1-[1-(1-cyanoiminoethyl)piperidin-4-yl]-5-cyclopropyl-1H-pyrazole-4-carbonyl}-[(S)-3-(2-trifluoromethylphenyl)]pyrrolidine 
• 96237-42-2 3-Cyanoamino-3-methyl-2-phenylsulphonylpropenenitrile 
• 86700-27-8 2-Amino-4-methyl-6-thioxo-1,6-dihydro-pyrimidine-5-carbonitrile 
• 339550-41-3 N'-Cyano-N-methyl-N-phenacylacetamidin 
• 339363-03-0 N'-cyano-N-(cyanomethyl)-N-methylacetimidamide 
• 58192-80-6 N'-Cyano-N-phenacyl-acetamidin 

Relevant articles and documents

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