4-Hydroxy-2,6-dimethylbenzonitrile

Base Information

• Chemical Name: 4-Hydroxy-2,6-dimethylbenzonitrile
• CAS No.: 58537-99-8
• Molecular Formula: C9H9 N O
• Molecular Weight: 147.177
• Hs Code.: 2926909090
• European Community (EC) Number: 875-173-6
• DSSTox Substance ID: DTXSID70343512
• Nikkaji Number: J136.393J
• Wikidata: Q72483829
• ChEMBL ID: CHEMBL3765491
• Mol file: 58537-99-8.mol

Synonyms:4-Hydroxy-2,6-dimethylbenzonitrile;58537-99-8;2,6-Dimethyl-4-hydroxybenzonitrile;Benzonitrile, 4-hydroxy-2,6-dimethyl-;4-Cyano-3,5-dimethylphenol;MFCD00238591;4-hydroxy-2,6-dimethyl-benzonitrile;3,5-Dimethyl-4-cyanophenol;SCHEMBL1128572;CHEMBL3765491;DTXSID70343512;BCP05911;4-Hydroxy-2,6-dimethylbenzonitrile #;AKOS005259316;AC-4482;CS-W002579;PS-4472;BP-10351;SY018896;A8284;AM20040786;FT-0618624;4-hydroxy-2,6-dimethylbenzonitrile, AldrichCPR;EN300-301970;Q-103462

Chemical Property of 4-Hydroxy-2,6-dimethylbenzonitrile

Chemical Property:

• Appearance/Colour: off-white Solid Not available
• Vapor Pressure: 0.000265mmHg at 25°C
• Melting Point: 176 ºC
• Boiling Point: 313.7°Cat760mmHg
• PKA: 8.08±0.23(Predicted)
• Flash Point: 143.5°C
• PSA: 44.02000
• Density: 1.13g/cm³
• LogP: 1.88068
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 147.068413911
• Heavy Atom Count: 11
• Complexity: 169

Purity/Quality:

4-Hydroxy-2,6-dimethylbenzonitrile ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-36
• Safety Statements: 26-36/37/39-36/37-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1C#N)C)O

Technology Process of 4-Hydroxy-2,6-dimethylbenzonitrile

There total 9 articles about 4-Hydroxy-2,6-dimethylbenzonitrile 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: 84.0%

4-((tert-butyldimethylsilyl)oxy)-2,6-dimethylbenzonitrile → 4-hydroxy-2,6-dimethylbenzonitrile (58537-99-8)

Guidance literature:

With hydrogenchloride; water;

DOI:10.1055/s-0035-1562781

Reference yield: 77.0%

potassium thioacyanate (333-20-0) + 3,5-Dimethylphenol (108-68-9,50356-23-5) → 4-hydroxy-2,6-dimethylbenzonitrile (58537-99-8)

Guidance literature:

With silica sulfuric acid; In neat (no solvent, solid phase); at 100 ℃; for 12h; regioselective reaction;

DOI:10.1021/acs.joc.8b02191

Reference yield: 61.0%

4-bromo-3,5-dimethylphenol (7463-51-6) + dicyanozinc (557-21-1) → 4-hydroxy-2,6-dimethylbenzonitrile (58537-99-8)

Guidance literature:

With tri-tert-butyl phosphine; zinc; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In hexane; N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1055/s-2003-42069

upstream raw materials:

4-acetoxy-2,6-dimethyl-benzonitrile

trimethylsilyl cyanide

2,6-dimethyl-1,4-benzoquinone

4-bromo-3,5-dimethylphenol

Downstream raw materials:

4-(1-Cyclopropanecarbonyl-2-cyclopropyl-2-oxo-ethoxy)-2,6-dimethyl-benzonitrile

4-(2-cyclopropyl-2-oxoethoxy)-2,6-dimethylbenzonitrile

4-[1-(cyclopropylcarbonyl)-2-oxopropoxy]-2,6-dimethylbenzonitrile

3-bromo-4-methoxy-2,6-dimethylbenzonitrile

Refernces

• 1、 Coman, Anca G.,Paraschivescu, Codruta C.,Hadade, Niculina D.,Juncu, Andrei,Vlaicu, Ovidiu,Popescu, Costin-Ioan,Matache, Mihaela. "New Acyloxymethyl Ketones: Useful Probes for Cysteine Protease Profiling". . p. 3917 - 3923. Retrieved 2016/11/11.
• 2、 Marshall, Laura J.,Cable, Karl M.,Botting, Nigel P.. "The synthesis of substituted phenols from pyranone precursors". experimental part. p. 8165 - 8170. Retrieved 2009/12/26.