Benzamidine

Base Information

• Chemical Name: Benzamidine
• CAS No.: 618-39-3
• Molecular Formula: C7H8N2
• Molecular Weight: 120.154
• Hs Code.: 29299000
• European Community (EC) Number: 216-795-4,210-546-3
• NSC Number: 243704
• UNII: KUE3ZY3J1F
• DSSTox Substance ID: DTXSID8045012
• Nikkaji Number: J95.743G,J3.531.736H
• Wikipedia: Benzamidine
• Wikidata: Q4890748
• Pharos Ligand ID: KZ3BN1XM8FFH
• Metabolomics Workbench ID: 52271
• ChEMBL ID: CHEMBL20936
• Mol file: 618-39-3.mol

Synonyms:benzamidine;benzamidine hydrochloride

Chemical Property of Benzamidine

Chemical Property:

• Melting Point: 65-70 °C
• Boiling Point: 208.5 °C at 760 mmHg
• PKA: 11.90±0.40(Predicted)
• Flash Point: 79.9 °C
• PSA: 49.87000
• Density: 1.09 g/cm³
• LogP: 1.77070
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 120.068748264
• Heavy Atom Count: 9
• Complexity: 104

Purity/Quality:

97% ^*data from raw suppliers

Benzamidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=N)N
• General Description: Benzamidine is utilized as a nucleophile in a micelle-catalyzed, one-pot synthesis of biologically active benzo[a]phenazines and naphtho[2,3-d]imidazoles, demonstrating its role in facilitating regio- and chemoselective reactions under environmentally friendly aqueous conditions.

Technology Process of Benzamidine

There total 48 articles about Benzamidine 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: 93.0%

N-hydroxybenzenecarboximidamide (613-92-3) → benzamidin (618-39-3)

Guidance literature:

With palladium diacetate; triphenylphosphine; In dimethyl sulfoxide; at 100 ℃; for 6h; Sealed tube;

DOI:10.1002/adsc.202100142

Reference yield: 92.0%

sodium thiophenolate (930-69-8) + 3-bromo-3-phenyl-3H-diazirine (4222-25-7) → benzonitrile (100-47-0) + benzamidin (618-39-3) + diphenyldisulfane (882-33-7)

Guidance literature:

In methanol; at 25 ℃; Rate constant; Mechanism; var. NaSPh conc.; also 15N-labelled phenylbromodiaziryne, other bromo- and chloro-aryldiazirines, also with sodium thioacetate;

DOI:10.1021/ja00070a003

Reference yield: 83.0%

benzamidine monohydrochloride (1670-14-0) → benzamidin (618-39-3)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 1h;

DOI:10.1002/adsc.201900954

upstream raw materials:

3-cyano-1-isopropylguanidine

benzylidenamine

ethyl benzimidate hydrochloride

ammonium thiocyanate

Downstream raw materials:

2-phenyl-5,6,7,8-tetrahydroquinazoline

2-phenyl-1,3,5-triazine

2,4-diphenyl-1,3,5-triazine

2-phenyl-5-[1-furan-2-yl-meth-(Z)-ylidene]-3,5-dihydro-imidazol-4-one

Refernces

Micelles catalyzed one pot regio- and chemoselective synthesis of benzo[a]phenazines and naphtho[2,3-d]imidazoles 'in H₂O'

10.1016/j.tetlet.2014.09.103

The study presents an efficient and environmentally friendly one-pot synthesis method for benzo[a]phenazines and naphtho[2,3-d]imidazoles, which are important due to their biological properties such as antibiotic, antimalarial, antiparasitic, and antitumor activities. The synthesis was achieved using 2,3-dichloro-1,4-naphthoquinone as the starting material, o-phenylenediamine and benzamidines as nucleophiles, and sodium dodecyl sulfate (SDS) micelles as a catalyst in water. The purpose of these chemicals was to undergo nucleophilic substitution reactions, leading to the formation of the desired benzo[a]phenazine and naphtho[2,3-d]imidazole derivatives with excellent yields, demonstrating a green and regio- and chemoselective approach to synthesizing these potentially pharmaceutically significant compounds.