Apraclonidine

Base Information

• Chemical Name: Apraclonidine
• CAS No.: 66711-21-5
• Molecular Formula: C9H10Cl2N4
• Molecular Weight: 245.111
• Hs Code.: 2933290090
• European Community (EC) Number: 636-293-2
• UNII: 843CEN85DI
• DSSTox Substance ID: DTXSID1048415
• Nikkaji Number: J247.956G
• Wikipedia: Apraclonidine
• Wikidata: Q4781812
• NCI Thesaurus Code: C61640
• RXCUI: 14845
• Pharos Ligand ID: 1NQSHR3BBNW5
• Metabolomics Workbench ID: 43220
• ChEMBL ID: CHEMBL647
• Mol file: 66711-21-5.mol

Synonyms:2-(4-amino-2,6-dichloro)phenyliminoimidazolidine;4-aminoclonidine;ALO 2145;ALO-2145;apraclonidine;apraclonidine hydrochloride;Iopidine;Iopimax;p-aminoclonidine;para-aminoclonidine

Chemical Property of Apraclonidine

Chemical Property:

• Vapor Pressure: 1.83E-06mmHg at 25°C
• Melting Point: >230°
• Boiling Point: 395.5 °C at 760 mmHg
• Flash Point: 193 °C
• PSA: 62.44000
• Density: 1.63 g/cm³
• LogP: 3.16730
• Storage Temp.: 2-8°C
• Solubility.: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.4 mg/mL
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 244.0282517
• Heavy Atom Count: 15
• Complexity: 247

Purity/Quality:

98%,99%, ^*data from raw suppliers

Apraclonidine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 22-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CN=C(N1)NC2=C(C=C(C=C2Cl)N)Cl
• Recent ClinicalTrials: Efficacy of Topical Apraclonidine for the Treatment of Ocular Synkinesis

Technology Process of Apraclonidine

There total 9 articles about Apraclonidine 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: 78.0%

p-Nitroclonidine (65936-26-7,741202-17-5) → para-aminoclonidine (66711-21-5)

Guidance literature:

With hydrazine hydrate; 5%-palladium/activated carbon; In ethanol; for 8h; Reflux;

DOI:10.1080/00304948.2016.1206429

Reference yield: 77.0%

2-(2',6'-dichloro-4'-nitroanilino)-2-imidazoline (65936-26-7) → p-aminoclonidine (66711-21-5)

Guidance literature:

With hydrogenchloride; iron; In ethanol; for 3h; Heating;

DOI:10.1021/jm00390a021

Reference yield:

(2,6-dichloro-4-nitrophenyl)carbonimidic dichloride (73218-65-2) → para-aminoclonidine (66711-21-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / tetrahydrofuran / 0.25 h / Cooling with ice

1.2: 6.5 h / 5 - 20 °C

2.1: 5%-palladium/activated carbon; hydrazine hydrate / ethanol / 8 h / Reflux

With hydrazine hydrate; 5%-palladium/activated carbon; triethylamine; In tetrahydrofuran; ethanol;

DOI:10.1080/00304948.2016.1206429

upstream raw materials:

2-(2',6'-dichloro-4'-nitroanilino)-2-imidazoline

4-nitro-2,6-dichloroaniline

N-(2,6-dichloro-4-nitrophenyl)formamide

(2,6-dichloro-4-nitrophenyl)carbonimidic dichloride

Downstream raw materials:

p-aminoclonidine hydrochloride

2-[(4-amino-2,6-dichlorophenyl)imino]imidazolidine monohydrochloride

isothiocyanato-4 clonidine

2-({2,6-dichloro-4-[3,3-(1,4-butanediyl)triazeno]phenyl}imino)imidazolidine

Refernces

• 1、 Zhang, He-Hui,An, Yu-Long,Xin, Wei-Xiang,Zhao, Sheng-Yin. "An Improved Procedure for the Preparation of Apraclonidine Hydrochloride". . p. 401 - 404. Retrieved 2016/09/14.
• 2、 -. "Feed additive for improving growth in agricultural animals". . . Retrieved 2008/06/13.