79463-77-7

Basic information

• Product Name: Diphenyl N-cyanocarbonimidate
• Synonyms: AURORA KA-4382;CYANOCARBONIMIDIC ACID DIPHENYL ESTER;DIPHENYL N-CYANOCARBONIMIDATE;DIPHENYL CYANOCARBONIMIDATE;N-CYANODIPHENYLIMIDOCARBONATE;Diphenyl cyanocarbonimidate (Diphenoxymethylenecyanamide);Cyanocarbonimidiaaciddiphenylaester;Diphenylcyanocarbonimidate,97%
• CAS NO: 79463-77-7
• Molecular Formula: C14H10N2O2
• Molecular Weight: 238.24
• EINECS: 427-300-8
• Product Categories: Aromatic Nitriles;Amidates/Imidates;Nitrogen Compounds;Organic Building Blocks
• Mol File: 79463-77-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 155-158 °C(lit.)
• Boiling Point: 380.84°C (rough estimate)
• Flash Point: 160.2 °C
• Appearance: White/Fluffy Powder
• Density: 1.1907 (rough estimate)
• Vapor Pressure: 8.13E-05mmHg at 25°C
• Refractive Index: 1.6500 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -6.70±0.50(Predicted)
• Water Solubility: Insoluble in water.
• Sensitive: Moisture Sensitive
• BRN: 4254248
• CAS DataBase Reference: Diphenyl N-cyanocarbonimidate(CAS DataBase Reference)
• NIST Chemistry Reference: Diphenyl N-cyanocarbonimidate(79463-77-7)
• EPA Substance Registry System: Diphenyl N-cyanocarbonimidate(79463-77-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37
• RIDADR: 3439
• WGK Germany: 3
• F: 10-21
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 79463-77-7(Hazardous Substances Data)

Usage

Chemical Properties

white fluffy powder

Uses

Diphenyl N-cyanocarbonimidate has been used in the preparation of N-substituted 2-amino-4H-3,1-benzoxazines, cyanoguanidine derivatives, oxadiazoles.

InChI:InChI=1/C14H10N2O2/c15-11-16-14(17-12-7-3-1-4-8-12)18-13-9-5-2-6-10-13/h1-10H

Synthetic route

CYANAMID (420-04-2) + dichlorodiphenoxymethane (4885-03-4) → N-cyanodiphenylcarbonimidate (79463-77-7)

Conditions	Yield
In ethyl acetate 1.) not above 80 deg C, 2.) R.T., 3.5 h.;	91%
In ethyl acetate <60 deg C;	51%

bis(phenyl) carbonate (102-09-0) → N-cyanodiphenylcarbonimidate (79463-77-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / PCl5 / 16 h / 155 °C 2: 51 percent / ethyl acetate / <60 deg C View Scheme
Multi-step reaction with 2 steps 1: 96 percent / phosphorus pentachloride / 1.) 160 deg C, 24 h, 2.) 200 deg 15 min. 2: 91 percent / ethyl acetate / 1.) not above 80 deg C, 2.) R.T., 3.5 h. View Scheme

N-cyanodiphenylcarbonimidate (79463-77-7) → 3-Amino-5-phenoxy-1H-1,2,4-triazole (146335-71-9)

Conditions	Yield
With hydrazine In methanol at 0 - 20℃; for 2h;	100%
With hydrazine In isopropyl alcohol for 3h; Heating;	59.5%

N-cyanodiphenylcarbonimidate (79463-77-7) + aniline (62-53-3) → N-cyano-N'-phenylcarbamimidic acid phenyl ester (84859-47-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 20℃; for 3h;	100%
In isopropyl alcohol for 2h; Ambient temperature;	98%
In acetonitrile at 20℃; for 18h;
In isopropyl alcohol
In isopropyl alcohol at 20℃;

N,N-dimethylammonium chloride (506-59-2) + N-cyanodiphenylcarbonimidate (79463-77-7) → O-phenyl-N-cyano-N',N'-dimethylurea (167494-04-4)

Conditions	Yield
In tetrahydrofuran	100%

N-[(10R,14S)-5-amino-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1(19),2(7),3,5,15,17-hexaen-14-yl]-1-(3-chloro-2-fluorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxamide dihydrochloride + N-cyanodiphenylcarbonimidate (79463-77-7) → 1-(3-chloro-2-fluorophenyl)-N-[(10R,14S)-5-{[(1Z)-(cyanoimino)(phenoxy)methyl]amino}-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1(19),2(7),3,5,15,17-hexaen-14-yl]-5-methyl-1H-1,2,3-triazole-4-carboxamide (1422448-80-3)

Conditions	Yield
With pyridine In isopropyl alcohol at 20℃; for 2h;	99%

N-cyanodiphenylcarbonimidate (79463-77-7) + (R)-N-[1-(3-bromophenyl)ethyl] acetamide (176707-77-0) → (R)-N3-(1-(3-bromophenyl)ethyl)-4H-1,2,4-triazole-3,5-diamine

Conditions	Yield
Stage #1: N-cyanodiphenylcarbonimidate; (R)-N-[1-(3-bromophenyl)ethyl] acetamide In isopropyl alcohol at 20 - 60℃; Stage #2: With hydrazine hydrate In methanol at 50℃; for 4h;	99%

4-benzyloxyaniline hydrochloride (51388-20-6) + N-cyanodiphenylcarbonimidate (79463-77-7) → C21H17N3O2 (929267-13-0)

Conditions	Yield
Stage #1: 4-benzyloxyaniline hydrochloride With triethylamine In isopropyl alcohol at 20℃; for 0.166667h; Stage #2: N-cyanodiphenylcarbonimidate In isopropyl alcohol at 20℃; for 3.5h;	98%

N-cyanodiphenylcarbonimidate (79463-77-7) + 4-(piperazin-1-yl)pyridine (1008-91-9) → C17H17N5O (1400691-99-7)

Conditions	Yield
In dichloromethane at 20℃; for 1h;	98%

(8S)-N-methyl-N-({1-[(3S)-3-piperidinylmethyl]-1H-benzimidazol-2-yl}methyl)-5,6,7,8-tetrahydro-8-quinolinamine (876590-12-4) + N-cyanodiphenylcarbonimidate (79463-77-7) → phenyl (3R)-N-cyano-3-{[2-({methyl[(8S)-5,6,7,8-tetrahydro-8-quinolinyl]amino}methyl)-1H-benzimidazol-1-yl]methyl}-1-piperidinecarboximidoate

Conditions	Yield
In isopropyl alcohol at 20℃;	97%

3-[4-(aminomethyl)-1,2,5-oxadiazol-3-yl]-4-(3-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5(4h)-one trifluoroacetate (943598-71-8) + N-cyanodiphenylcarbonimidate (79463-77-7) + trifluoroacetic acid (76-05-1) → N-(3-chloro-4-fluorophenyl)-4-[((E/Z)-((cyanoimino)[(4-methoxybenzyl)amino]methyl)-amino)methyl]-N'-hydroxy-1,2,5-oxadiazole-3-carboximidamide trifluoroacetate

Conditions	Yield
Stage #1: 3-[4-(aminomethyl)-1,2,5-oxadiazol-3-yl]-4-(3-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5(4h)-one trifluoroacetate; N-cyanodiphenylcarbonimidate With triethylamine In tetrahydrofuran at 20℃; for 2h; Stage #2: With sodium hydroxide; water In tetrahydrofuran at 20℃; for 0.5h; Stage #3: trifluoroacetic acid With acetic acid more than 3 stages;	97%

(+/-)-cis-[3-(1H-imidazol-4-yl)cyclopentyl]methanamine + N-cyanodiphenylcarbonimidate (79463-77-7) → (+/-)-1-cyano-3-{[cis-3-(1H-imidazol-4-yl)cyclopentyl]methyl}-2-phenylisourea

Conditions	Yield
In isopropyl alcohol at 20℃; for 1h;	97%

N-cyanodiphenylcarbonimidate (79463-77-7) + 2-(4,5-Diphenyl-1H-imidazol-2-yl)-ethylamine (88883-83-4) → <<2-(4,5-Diphenyl-1H-imidazol-2-yl)ethylamino>phenoxymethylen>cyanamid (92095-56-2)

Conditions	Yield
In ethanol; dichloromethane for 0.5h; Ambient temperature;	96%

(3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-[4-(2-aminoethoxy)benzyl]-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxypropylcarbamate (313680-01-2) + N-cyanodiphenylcarbonimidate (79463-77-7) → (3R,3aS,6aR).-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-1-[4-(2-{[(E and/or Z)-(cyanoimino)(phenoxy)methyl]amino}ethoxy)benzyl]-2-hydroxypropylcarbamate

Conditions	Yield
With triethylamine In dichloromethane; isopropyl alcohol at 20℃; for 2.5h;	96%

1-(4-methoxyphenyl)piperazine (38212-30-5) + N-cyanodiphenylcarbonimidate (79463-77-7) → C19H20N4O2 (1400691-98-6)

Conditions	Yield
In dichloromethane at 20℃; for 24h;	96%

N-cyanodiphenylcarbonimidate (79463-77-7) + 1-(pyridin-4-ylmethyl)piperazine (62089-74-1) → C18H19N5O (1400692-03-6)

Conditions	Yield
In dichloromethane at 20℃; for 1h;	96%

C14H19ClN2O + N-cyanodiphenylcarbonimidate (79463-77-7) → phenyl‐N‐(1‐(3‐(2‐chlorophenyl)propanoyl)piperidin‐4‐yl)‐N’‐cyanocarbamimidate

Conditions	Yield
In dichloromethane for 1h;	96%

N-cyanodiphenylcarbonimidate (79463-77-7) + 4-(4-Aminobenzoyl)-1,3-dihydro-5-methyl-3H-imidazol-2-one (173375-23-0) → N1-Cyano-N2-<4-<(1,3-dihydro-5-methyl-2-oxo-3H-imidazol-4-yl)carbonyl>phenyl>-O-phenyl isourea (173375-92-3)

Conditions	Yield
With pyridine for 5h; Ambient temperature;	95%

N-cyanodiphenylcarbonimidate (79463-77-7) + 1-(3-{N'-[4-(2-Amino-ethylsulfanylmethyl)-thiazol-2-yl]-guanidinomethyl}-phenyl)-3-((R)-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)-urea; hydrochloride → C33H31N11O2S2

Conditions	Yield
With triethylamine In methanol for 4h; Ambient temperature;	95%

N-(6-amino-2,3-dichlorobenzyl)glycine ethyl ester (70406-92-7) + N-cyanodiphenylcarbonimidate (79463-77-7) → ethyl (2-cyanoimino-5,6-dichloro-1,2,3,4-tetrahydroquinazolin-3-yl)-acetate (146374-56-3)

Conditions	Yield
In acetonitrile for 3h; Heating;	95%
In water; ethyl acetate; acetonitrile
In N-methyl-acetamide; benzene

4-morpholino-4-yl-phenylamine (2524-67-6) + N-cyanodiphenylcarbonimidate (79463-77-7) → N-cyano-N'-(4-morpholino-phenyl)-O-phenylisourea (700804-71-3)

Conditions	Yield
In isopropyl alcohol for 22h;	95%
In isopropyl alcohol at 100℃;

N-cyanodiphenylcarbonimidate (79463-77-7) + 2,4-Dimethoxyaniline (2735-04-8) → N-cyano-N'-(2,4-dimethoxy-phenyl)-O-phenylisourea (700804-95-1)

Conditions	Yield
In isopropyl alcohol at 20℃; for 24 - 48h;	95%

3-Phenylpropan-1-amine (2038-57-5) + N-cyanodiphenylcarbonimidate (79463-77-7) → 1-cyano-2-phenyl-3-(3-phenylpropyl)isourea (1192559-65-1)

Conditions	Yield
In dichloromethane at 20℃; for 2h; Inert atmosphere;	95%
In dichloromethane at 20℃; for 1h;	86%
In isopropyl alcohol at 20℃; for 1h;	84%
With isopropyl alcohol at 20℃; for 1h;

N-cyanodiphenylcarbonimidate (79463-77-7) + 3-methoxy-4-(1,3-oxazol-5-yl)aniline (198821-79-3) → C18H14N4O3 (267647-77-8)

Conditions	Yield
In acetonitrile at 20℃;	94%

endo 2-methyl-1-{8-[2-(4-phenylpiperidin-4-yl)ethyl]-8-azabicyclo[3.2.1]oct-3-yl}-1H-benzimidazole dihydrochloride + N-cyanodiphenylcarbonimidate (79463-77-7) → phenyl N-cyano-4-{2-[3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-phenylpiperidine-1-carboximidoate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 4h;	94%

methyl 4-[(4-phenyl-3,6-dihydropyridin-1(2H)-yl)sulfonyl]methylpiperidine-4-carboxylate (869189-73-1) + N-cyanodiphenylcarbonimidate (79463-77-7) → methyl 1-[(cyanoimino)(phenoxy)methyl]-4-{[(4-phenyl-3,6-dihydropyridin-1(2H)-yl)sulfonyl]methyl}piperidine-4-carboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 90℃; for 16h;	94%

endo 2-methyl-1-{8-[2-(4-phenylpiperidin-4-yl)ethyI]-8-azabicyclo[3.2.1]oct-3-yl}-1H-benzimidazole (716348-30-0) + N-cyanodiphenylcarbonimidate (79463-77-7) → phenyl N-cyano-4-{2-[3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-phenylpiperidine-1-carboximidoate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 4h;	94%

N-cyanodiphenylcarbonimidate (79463-77-7) + 2-phenoxyethanamine (1758-46-9) → 1-cyano-2-phenyl-3-[2-(phenoxy)ethyl]isourea

Conditions	Yield
In isopropyl alcohol at 20℃; for 1h;	94%

3-Aminomethylpyridine (3731-52-0) + N-cyanodiphenylcarbonimidate (79463-77-7) → phenyl N'-cyano-N-(pyridin-3-ylmethyl)carbamimidate

Conditions	Yield
In isopropyl alcohol at 20℃; for 18h;	94%

3-(3-aminopropoxy)-N,N-dimethylbenzenemethanamine (69384-05-0) + N-cyanodiphenylcarbonimidate (79463-77-7) → N'-cyano-N-<3-<3-<(dimethylamino)methyl>phenoxy>propyl>-O-phenylisourea (84035-82-5)

Conditions	Yield
In diethyl ether for 1h; Ambient temperature;	92%

N-cyanodiphenylcarbonimidate (79463-77-7) + 1,2-diamino-benzene (95-54-5) → 2-benzimidazolylcarbamonitrile (55864-37-4)

Conditions	Yield
In isopropyl alcohol for 1h; Heating;	92%

N-cyanodiphenylcarbonimidate (79463-77-7) + 4-{[(2-aminoethyl)thio]methyl}-5-methylimidazole (38585-67-0) → N-<2<<(5-methyl-1H-imidazol-4-yl)methyl>thio>ethyl>-N'-cyano-O-phenylisourea (110821-25-5, 112528-18-4, 112528-19-5)

Conditions	Yield
With potassium carbonate In water; ethyl acetate for 4h;	92%
In diethyl ether for 1h; Ambient temperature; Yield given;

Upstream product

• 420-04-2 CYANAMID 
• 4885-03-4 dichlorodiphenoxymethane 
• 102-09-0 bis(phenyl) carbonate 

Downstream Products

• 141995-98-4 C₁₅H₁₃BrN₄OS 
• 115063-09-7 C₂₃H₂₈N₄O₂ 
• 117078-41-8 N-cyano-O-phenyl-N'-<4-<3-(1-piperidinylmethyl)phenoxy>butyl>isourea 
• 98078-91-2 N-cyano-O-phenyl-N'-<3-<3-(1-piperidinylmethyl)phenoxy>propyl>isourea 
• 112528-14-0 C₂₃H₂₈N₄O₂ 
• 150059-13-5 N-cyano-N'-octyl-O-phenylisourea 
• 111971-01-8 C₁₄H₁₅N₃O₅ 
• 146335-66-2 C₁₄H₁₇N₃O₃ 
• 146335-67-3 N-cyano-N'-(S)-(1-benzyloxycarbonyl-2-phenylethyl)-O-phenylisourea 
• 146335-70-8 N-cyano-N'-(1-benzyloxycarbonylpropyl)-O-phenylisourea 
• 111970-99-1 C₁₂H₁₃N₃O₃ 
• 26364-65-8 2-(N-cyanoimino)thiazolidine 
• 84035-81-4 C₁₈H₂₂N₄O₂S 
• 133637-86-2 C₂₄H₂₇N₃O₅ 

Relevant articles and documents

Novel Gonadotropin-Releasing Hormone Antagonists: Peptides Incorporating Modified Nω-Cyanoguanidino Moieties

In order to minimize the deleterious effects of histamine release resulting from the administration to rats and humans of some potent gonadotropin-releasing hormone (GnRH) antagonists, various arginine residues were replaced with the less basic Nω-cyano-Nω'-alkyl- or -arylhomoarginine, -arginine, or -p-aminophenylalanine and Nω-triazolyllysine, -ornithine or -p-aminophenylalanine residues in active analogues.These novel analogues were synthesized on a solid-phase support via a two-step modification of the Nω-NH2 of lysine, ornithine, or p-aminophenylalanineresidues in otherwise protected resin bound peptides.Most analogues were tested in the rat antiovulatory assay (AOA) and three in vitro assays: a pituitary cell culture assay, a binding assay to pituitary cell membranes, and a histamine release assay.Introduction of the cyanoguanidino and Nω-triazolyl moieties into GnRH analogues yielded several water-soluble antagonists which showed a desirable therapeutic ratio (low histamine release activity to high in vivo potency).Among them, "Azaline" (10, 1,DCpa2,DPal3,Lys5(atz),DLys6(atz),ILys8,DAla10>GnRH), inhibited ovulation in the rat by 90percent at 2 μg/rat with an ED50 in the in vitro histamine release assay comparable to that of GnRH itself.