2-[4-(Oxiran-2-ylmethoxy)phenyl]acetonitrile

Base Information

• Chemical Name: 2-[4-(Oxiran-2-ylmethoxy)phenyl]acetonitrile
• CAS No.: 35198-42-6
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.214
• DSSTox Substance ID: DTXSID501276079
• Mol file: 35198-42-6.mol

Synonyms:35198-42-6;2-[4-(oxiran-2-ylmethoxy)phenyl]acetonitrile;4-(2-Oxiranylmethoxy)benzeneacetonitrile;[4-(oxiran-2-ylmethoxy)phenyl]acetonitrile;2-{4-[(oxiran-2-yl)methoxy]phenyl}acetonitrile;2-[4-[(Oxiran-2-yl)methoxy]phenyl]acetonitrile;SCHEMBL7774526;WDGZJFDDPCUVPF-UHFFFAOYSA-N;DTXSID501276079;4-(2,3-epoxypropoxy)benzylcyanide;AKOS000200211;AKOS017274232;3-(4-cyanomethylphenoxy)propylene oxide;CS-0233437;EN300-13351;Z90122420

Chemical Property of 2-[4-(Oxiran-2-ylmethoxy)phenyl]acetonitrile

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 189.078978594
• Heavy Atom Count: 14
• Complexity: 225

Purity/Quality:

99% ^*data from raw suppliers

4-(2-Oxiranylmethoxy)benzeneacetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(O1)COC2=CC=C(C=C2)CC#N
• Uses: 4-(2-Oxiranylmethoxy)benzeneacetonitrile is an intermediate for the synthesis of Atenolol (A790075), a cardioselective β-adrenergic blocker.

Technology Process of 2-[4-(Oxiran-2-ylmethoxy)phenyl]acetonitrile

There total 1 articles about 2-[4-(Oxiran-2-ylmethoxy)phenyl]acetonitrile 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:

(4-hydroxyphenyl)methanol (623-05-2) → 1-(4'-Cyanomethylphenoxy)-2,3-epoxypropane (35198-42-6)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N-dimethyl-formamide

2: piperidine / 6 h / 95 - 100 °C

With piperidine; In N,N-dimethyl-formamide;

DOI:10.1021/op9800313

Reference yield: 92.0%

1-(4'-Cyanomethylphenoxy)-2,3-epoxypropane (35198-42-6) + terephthalaldehyde, (623-27-8) → C30H24N2O4

Guidance literature:

With sodium hydroxide; In ethanol;

Reference yield: 65.0%

1-(4'-Cyanomethylphenoxy)-2,3-epoxypropane (35198-42-6) + 6-chloro-2-methylquinazolin-4-(3H)-one (7142-09-8) → 2-(4-(3-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-2-hydroxypropoxy)phenyl)acetonitrile

Guidance literature:

With tetra-(n-butyl)ammonium iodide; caesium carbonate; In acetonitrile; at 100 ℃; for 16h;

DOI:10.1021/acsinfecdis.1c00175

upstream raw materials:

(4-hydroxyphenyl)methanol

Downstream raw materials:

tert-butyl 1,4-diazepine-1-carboxylate

1-(4-cyanomethylphenoxy)-3-diisopropylamino-2-propanol

(RS)-atenolol

1-(4'-cyanomethylphenoxy)-2-hydroxy-3-(isopropylamino)propane

Refernces