Hydrazinecarboximidamide, 2-[cyano(2,3-dichlorophenyl)methylene]-

Base Information

• Chemical Name: Hydrazinecarboximidamide, 2-[cyano(2,3-dichlorophenyl)methylene]-
• CAS No.: 84689-20-3
• Molecular Formula: C9H7Cl2N5
• Molecular Weight: 256.094
• European Community (EC) Number: 303-725-3,617-611-9
• DSSTox Substance ID: DTXSID501178869
• Mol file: 84689-20-3.mol

Synonyms:Lamotrigine Impurity C;84689-20-3;Hydrazinecarboximidamide, 2-[cyano(2,3-dichlorophenyl)methylene]-;94213-23-7;2,3-dichloro-N-(diaminomethylideneamino)benzenecarboximidoyl cyanide;Hydrazinecarboximidamide, 2-(cyano(2,3-dichlorophenyl)methylene)-;(Z)-(Cyano(2,3-dichlorophenyl)methylene)carbazamidine;(Z)-[cyano(2,3-dichlorophenyl)methylene]carbazamidine;2-[Cyano(2,3-dichlorophenyl)methylene]hydrazinecarboximidamide;SCHEMBL3976523;(1Z)-2,3-dichloro-N-(diaminomethylideneamino)benzenecarboximidoyl cyanide;BXDSJOGMJUKSAE-UHFFFAOYSA-N;DTXSID501178869;BCP33645;AKOS028112692;2,3-dichlorobenzoyl cyanide amidinohydrazone;FT-0641978;FT-0778055;FT-0778056

Chemical Property of Hydrazinecarboximidamide, 2-[cyano(2,3-dichlorophenyl)methylene]-

Chemical Property:

• Vapor Pressure: 3.91E-08mmHg at 25°C
• Melting Point: 176-178 °C
• Refractive Index: 1.669
• Boiling Point: 445.6 °C at 760 mmHg
• PKA: 4.06±0.70(Predicted)
• Flash Point: 223.3 °C
• PSA: 98.05000
• Density: 1.52 g/cm³
• LogP: 2.89508
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 255.0078506
• Heavy Atom Count: 16
• Complexity: 352

Purity/Quality:

99.9% ^*data from raw suppliers

2-(2,3-Dichlorphenyl)-2-(guanidinylimino)acetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)Cl)Cl)C(=NN=C(N)N)C#N
• Uses: 2-(2,3-Dichlorphenyl)-2-(guanidinylimino)acetonitrile (Lamotrigine EP Impurity C) is an intermediate in the synthesis of the drug Lamotrigine (L173250). An intermediate in the synthesis of the drug Lamotrigine (L173250).

Technology Process of Hydrazinecarboximidamide, 2-[cyano(2,3-dichlorophenyl)methylene]-

There total 3 articles about Hydrazinecarboximidamide, 2-[cyano(2,3-dichlorophenyl)methylene]- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.3%

2,3-dichlorobenzoyl cyanide (77668-42-9) → 2-(2,3-dichlorophenyl)-2-(guanidinoimino)acetonitrile (84689-20-3)

Guidance literature:

2,3-dichlorobenzoyl cyanide; With sulfuric acid; aminoguanidine bicarbonate; In water; acetonitrile; at 25 - 50 ℃; for 30h;

With ammonia; water; pH=6 - 7;

With sodium hydroxide; water; at 15 - 25 ℃; pH=9.5 - 10;

Reference yield: 67.0%

2,3-dichlorobenzoyl cyanide (77668-42-9) + aminoguanidine (79-17-4) → 2-(2,3-dichlorophenyl)-2-guanidinyliminoacetonitrile (84689-20-3,94213-23-7)

Guidance literature:

With PPA; In 1,2-dimethoxyethane;

Reference yield:

2,3-dichlorobenzoyl cyanide (77668-42-9) + aminoguanidine bicarbonate (2582-30-1) → 2-(2,3-dichlorophenyl)-2-guanidinyliminoacetonitrile (84689-20-3,94213-23-7)

Guidance literature:

aminoguanidine bicarbonate; With sulfuric acid; toluene-4-sulfonic acid; In toluene; at 110 ℃; for 0.25h;

2,3-dichlorobenzoyl cyanide; In toluene; at 80 ℃; for 3.5h; Heating / reflux;

upstream raw materials:

2,3-dichlorobenzoyl cyanide

aminoguanidine

aminoguanidine bicarbonate

Downstream raw materials:

lamotrigine

Refernces

• 1、 -. "Process for the preparation of 6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine, commonly known as lamotrigine". Page/Page column 8-9. . Retrieved 2010/01/31.
• 2、 -. "Process for preparing substituted benzoyl cyanide amidinohydrazones". . . Retrieved 2008/06/13.