2-Hydroxy-3-methoxybenzonitrile

Base Information

• Chemical Name: 2-Hydroxy-3-methoxybenzonitrile
• CAS No.: 6812-16-4
• Molecular Formula: C8H7NO2
• Molecular Weight: 149.149
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID20500739
• Nikkaji Number: J3.079.636E
• Wikidata: Q82352615
• Mol file: 6812-16-4.mol

Synonyms:2-hydroxy-3-methoxybenzonitrile;6812-16-4;2-Hydroxy-3-methoxybenzenecarbonitrile;MFCD02261936;Benzonitrile,2-hydroxy-3-methoxy-;Benzonitrile, 2-hydroxy-3-methoxy-;SCHEMBL1267795;3-methoxy-2-hydroxybenzonitrile;2-hydroxy-3-methoxy-benzonitrile;DTXSID20500739;NILKMGHUFOHVMU-UHFFFAOYSA-N;AKOS002292407;FB-0600;SY104147;CS-0067940;FT-0681005;EN300-316862;J-509618;N-(4(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalidene)methanamine

Chemical Property of 2-Hydroxy-3-methoxybenzonitrile

Chemical Property:

• Vapor Pressure: 0.005mmHg at 25°C
• Refractive Index: 1.569
• Boiling Point: 268.209 °C at 760 mmHg
• Flash Point: 116.009 °C
• PSA: 53.25000
• Density: 1.245 g/cm³
• LogP: 1.27248
• Storage Temp.: 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 149.047678466
• Heavy Atom Count: 11
• Complexity: 172

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Hydroxy-3-methoxybenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=CC(=C1O)C#N

Technology Process of 2-Hydroxy-3-methoxybenzonitrile

There total 7 articles about 2-Hydroxy-3-methoxybenzonitrile 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%

3-methoxy-2-hydroxybenzaldehyde (148-53-8) → 2-Hydroxy-3-methoxybenzonitrile (6812-16-4)

Guidance literature:

With iron(III) chloride; hydroxylamine hydrochloride; In N,N-dimethyl-formamide; for 3h; Reflux;

DOI:10.1016/j.tetlet.2013.06.134

Reference yield: 97.0%

o-vanillinoxime (2169-99-5) → 2-Hydroxy-3-methoxybenzonitrile (6812-16-4)

Guidance literature:

With iron(III) chloride; silica gel; In neat (no solvent); at 110 ℃; for 2h; Green chemistry;

DOI:10.1080/00397911.2016.1167910

Reference yield:

2-hydroxy-3-methoxy-benzaldehyde-(O-acetyl oxime ) → 2-Hydroxy-3-methoxybenzonitrile (6812-16-4)

Guidance literature:

at 40 - 50 ℃; under 2 Torr;

upstream raw materials:

acetic anhydride

o-vanillinoxime

3-methoxy-2-hydroxybenzaldehyde

Downstream raw materials:

1-(2-hydroxy-3-methoxyphenyl)ethanone

(2-hydroxy-3-methoxyphenyl)(phenyl)methanone

5-bromo-2-hydroxy-3-methoxy-benzonitrile

5-acetyl-2,3-dihydroxy-benzonitrile

Refernces

• 1、 Ghosh, Pranab,Pariyar, Gyan Chandra,Saha, Bittu,Subba, Raju. "FeCl3-silica: A green approach for the synthesis of nitriles from oximes". supporting information. p. 685 - 691. Retrieved 2016/06/08.
• 2、 Ghosh, Pranab,Subba, Raju. "FeCl3 mediated one-pot route to nitriles". supporting information. p. 4885 - 4887. Retrieved 2013/08/28.