3-(4-Hydroxy-3-methyl-phenyl)propanenitrile

Base Information

• Chemical Name: 3-(4-Hydroxy-3-methyl-phenyl)propanenitrile
• CAS No.: 22516-99-0
• Molecular Formula: C10H11NO
• Molecular Weight: 161.203
• DSSTox Substance ID: DTXSID801279408
• Nikkaji Number: J141.672C
• Mol file: 22516-99-0.mol

Synonyms:22516-99-0;3-(4-Hydroxy-3-methyl-phenyl)propanenitrile;3-(4-hydroxy-3-methylphenyl)propanenitrile;4-Hydroxy-3-methylbenzenepropanenitrile;SCHEMBL10775914;HJZKXUMPVHDEBH-UHFFFAOYSA-N;DTXSID801279408;MFCD00053074;AKOS005215963;EN300-6493844

Chemical Property of 3-(4-Hydroxy-3-methyl-phenyl)propanenitrile

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 60 °C
• Boiling Point: 345.932°C at 760 mmHg
• PKA: 10.26±0.20(Predicted)
• Flash Point: 163.014°C
• PSA: 44.02000
• Density: 1.098g/cm³
• LogP: 2.15678
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 161.084063974
• Heavy Atom Count: 12
• Complexity: 182

Purity/Quality:

3-(4-Hydroxy-3-methyl-phenyl)propanenitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C=CC(=C1)CCC#N)O

Technology Process of 3-(4-Hydroxy-3-methyl-phenyl)propanenitrile

There total 4 articles about 3-(4-Hydroxy-3-methyl-phenyl)propanenitrile 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: 99.0%

3-(4-methoxy-3-methylphenyl)propanenitrile (22446-57-7) → 3-(4-hydroxy-3-methylphenyl)propanenitrile (22516-99-0)

Guidance literature:

With boron tribromide; In dichloromethane; at 20 ℃; for 9h;

DOI:10.1002/anie.200462316

Reference yield:

1-iodo-4-methoxy-3-methylbenzene (75581-11-2) → 3-(4-hydroxy-3-methylphenyl)propanenitrile (22516-99-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / Bu₄NCl; NaHCO₃ / Pd(OAc)2 / dimethylformamide / 19 h / 40 °C

2: 96 percent / Mg / methanol / 5 h / 20 °C

3: 99 percent / BBr₃ / CH₂Cl₂ / 9 h / 20 °C

With tetrabutyl-ammonium chloride; boron tribromide; sodium hydrogencarbonate; magnesium; palladium diacetate; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.200462316

Reference yield:

(E)-3-(4-Methoxy-3-methyl-phenyl)-acrylonitrile → 3-(4-hydroxy-3-methylphenyl)propanenitrile (22516-99-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / Mg / methanol / 5 h / 20 °C

2: 99 percent / BBr₃ / CH₂Cl₂ / 9 h / 20 °C

With boron tribromide; magnesium; In methanol; dichloromethane;

DOI:10.1002/anie.200462316

upstream raw materials:

ortho-cresol

acrylonitrile

3-(4-methoxy-3-methylphenyl)propanenitrile

1-iodo-4-methoxy-3-methylbenzene

Downstream raw materials:

methyl 3-(4-hydroxy-3-methylphenyl)propanoate

β-<3-Methyl-4-oxo-cyclohexyl>-propionsaeure-methylester

Refernces