4-Hydroxy-3,5-dimethoxybenzonitrile

Base Information

• Chemical Name: 4-Hydroxy-3,5-dimethoxybenzonitrile
• CAS No.: 72684-95-8
• Molecular Formula: C9H9 N O3
• Molecular Weight: 179.175
• Hs Code.: 2926909090
• European Community (EC) Number: 700-251-2,615-787-1
• DSSTox Substance ID: DTXSID60888169
• Nikkaji Number: J972.119C
• Wikidata: Q82867701
• Mol file: 72684-95-8.mol

Synonyms:4-hydroxy-3,5-dimethoxybenzonitrile;72684-95-8;4-Cyano-2,6-dimethoxyphenol;Benzonitrile, 4-hydroxy-3,5-dimethoxy-;4-Hydroxy-3,5-dimethoxy-Benzonitrile;EC 700-251-2;SCHEMBL443285;DTXSID60888169;XCA68495;3,5-dimethoxy-4-hydroxy-benzonitrile;3,5 Dimethoxy-4-hydroxy-benzonitrile;AKOS006243107;TS-02495;NS00006558;A19101;EN300-238626;F2147-0720

Chemical Property of 4-Hydroxy-3,5-dimethoxybenzonitrile

Chemical Property:

• Vapor Pressure: 0.000298mmHg at 25°C
• Refractive Index: 1.554
• Boiling Point: 311.9°C at 760 mmHg
• Flash Point: 142.4°C
• PSA: 62.48000
• Density: 1.26g/cm³
• LogP: 1.28108
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 179.058243149
• Heavy Atom Count: 13
• Complexity: 196

Purity/Quality:

99.9% ^*data from raw suppliers

4-Cyano-2,6-dimethoxyphenol 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1O)OC)C#N
• Uses: 4-Hydroxy-3,5-dimethoxybenzonitrile is used as a reactant in the switching and extension of daisy-chain dimer polymer.

Technology Process of 4-Hydroxy-3,5-dimethoxybenzonitrile

There total 7 articles about 4-Hydroxy-3,5-dimethoxybenzonitrile 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: 98.0%

syringic aldehyde (134-96-3) → 3,5-dimethoxy-4-hydroxybenzonitrile (72684-95-8)

Guidance literature:

With acetic acid; hydroxylamine-O-sulfonic acid; In water; at 50 ℃; for 6h;

DOI:10.1016/j.tetlet.2016.07.047

Reference yield: 67.0%

3,4,5-trimethoxybenzonitrile (1885-35-4) → 3,5-dimethoxy-4-hydroxybenzonitrile (72684-95-8)

Guidance literature:

With 2-(diethylamino)ethanethiol hydrochloride; sodium t-butanolate; In N,N-dimethyl-formamide; for 0.8h; Heating;

DOI:10.1021/jo0611059

Reference yield: 10.0%

3,5-dimethoxy-benzonitrile (19179-31-8) → 3,5-dimethoxy-4-hydroxybenzonitrile (72684-95-8) + 2-Hydroxy-3,5-dimethoxy-benzonitrile

Guidance literature:

With dihydrogen peroxide; In formic acid; water; at 40 ℃; for 0.0666667h;

DOI:10.1246/bcsj.62.1652

upstream raw materials:

4-acetoxy-3,5-dimethoxy-benzonitrile

3,5-dimethoxy-benzonitrile

syringic aldehyde

3,4,5-trimethoxybenzonitrile

Downstream raw materials:

1,5-bis(4-cyano-2,6-dimethoxyphenoxy)-N-methyl-3-azapentane

N,N-bis[2-(4-cyano-2,6-dimethoxyphenoxy)ethyl]benzenesulfonamide

3,5-dimethoxy-4-(2-morpholine-4-yl-ethoxy)benzonitrile

3,5-dimethoxy-4-(4-tetrahydropyranyloxy)benzonitrile

Refernces

• 1、 Quinn, Dylan J.,Haun, Graham J.,Moura-Letts, Gustavo. "Direct synthesis of nitriles from aldehydes with hydroxylamine-O-sulfonic acid in acidic water". supporting information. p. 3844 - 3847. Retrieved 2016/08/02.
• 2、 Rokade, Balaji V.,Prabhu, Kandikere Ramaiah. "Chemoselective Schmidt reaction mediated by triflic acid: Selective synthesis of nitriles from aldehydes". experimental part. p. 5364 - 5370. Retrieved 2012/09/07.