1-[2-[[3-(2-Cyanophenoxy)-2-hydroxypropyl]amino]ethyl]-3-phenylurea

Base Information

• Chemical Name: 1-[2-[[3-(2-Cyanophenoxy)-2-hydroxypropyl]amino]ethyl]-3-phenylurea
• CAS No.: 53671-71-9
• Deprecated CAS: 71538-43-7
• Molecular Formula: C19H22 N4 O3
• Molecular Weight: 354.409
• Hs Code.: 2926909090
• UNII: C027IY98WE
• DSSTox Substance ID: DTXSID50968444
• Nikkaji Number: J227.909F
• Wikidata: Q27163326
• ChEMBL ID: CHEMBL11268
• Mol file: 53671-71-9.mol

Synonyms:ICI 89 406;ICI 89,406;ICI 89406;ICI-89406

Chemical Property of 1-[2-[[3-(2-Cyanophenoxy)-2-hydroxypropyl]amino]ethyl]-3-phenylurea

Chemical Property:

• Melting Point: 155-156 °C(Solv: acetonitrile (75-05-8))
• Boiling Point: 575 °C at 760 mmHg
• PKA: 12.29±0.46(Predicted)
• Flash Point: 301.5 °C
• PSA: 106.41000
• Density: 1.25 g/cm³
• LogP: 2.56408
• Storage Temp.: Store at RT
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 354.16919058
• Heavy Atom Count: 26
• Complexity: 459

Purity/Quality:

98%Min ^*data from raw suppliers

ICI89406 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)NC(=O)NCCNCC(COC2=CC=CC=C2C#N)O
• Uses: ICI 89406 is beta-1-selective antagonist.

Technology Process of 1-[2-[[3-(2-Cyanophenoxy)-2-hydroxypropyl]amino]ethyl]-3-phenylurea

There total 4 articles about 1-[2-[[3-(2-Cyanophenoxy)-2-hydroxypropyl]amino]ethyl]-3-phenylurea 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: 41.0%

2-<<(phenylamino)carbonyl>amino>ethylamine hydrochloride (85850-48-2) + 1,2-epoxy-3-(2-cyanophenyl)propane (38465-16-6) → 1-(2-cyanophenoxy)-3-β-(3-phenylureido)ethylamino-2-propanol (53671-71-9,71538-43-7)

Guidance literature:

With sodium hydroxide; In propan-1-ol; water; at 90 ℃; for 0.5h;

DOI:10.1016/S0968-0896(03)00297-9

Reference yield: 11.0%

1-(2-aminoethyl)-3-phenylurea (53673-01-1) + 1,2-epoxy-3-(2-cyanophenyl)propane (38465-16-6) → 1-(2-cyanophenoxy)-3-β-(3-phenylureido)ethylamino-2-propanol (53671-71-9,71538-43-7)

Guidance literature:

With sodium hydroxide; In propan-1-ol; for 18h; Heating;

DOI:10.1021/jm00353a004

Reference yield:

salicylonitrile (611-20-1) → 1-(2-cyanophenoxy)-3-β-(3-phenylureido)ethylamino-2-propanol (53671-71-9,71538-43-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / NaOH / H₂O / 50 °C

2: 41 percent / NaOH / propan-1-ol; H₂O / 0.5 h / 90 °C

With sodium hydroxide; In propan-1-ol; water;

DOI:10.1016/S0968-0896(03)00297-9

upstream raw materials:

1-(2-aminoethyl)-3-phenylurea

1,2-epoxy-3-(2-cyanophenyl)propane

2-<<(phenylamino)carbonyl>amino>ethylamine hydrochloride

salicylonitrile

Refernces

• 1、 Large, M.S.,Smith, L.H.. "β-Adrenergic Blocking Agents. 22. 1-Phenoxy-3-amino>-2-propanols". . p. 1286 - 1292. Retrieved 2007/10/02.