4-Hydroxy-3-methoxybenzonitrile

Base Information

• Chemical Name: 4-Hydroxy-3-methoxybenzonitrile
• CAS No.: 4421-08-3
• Molecular Formula: C8H7NO2
• Molecular Weight: 149.149
• Hs Code.: 29269090
• European Community (EC) Number: 224-589-0
• NSC Number: 158285
• DSSTox Substance ID: DTXSID20196070
• Nikkaji Number: J126.364A
• Wikidata: Q72484761
• Mol file: 4421-08-3.mol

Synonyms:4-Hydroxy-3-methoxybenzonitrile;4421-08-3;Vanillonitrile;4-hydroxy-3-methoxy-benzonitrile;m-Anisonitrile, 4-hydroxy-;3-methoxy-4-hydroxybenzonitrile;2-methoxy-4-cyanophenol;4-cyano-2-methoxyphenol;5-cyano-2-hydroxyanisole;2-methoxy-4-cyano-phenol;4-Hydroxy-meta-anisonitrile;SCHEMBL459931;3-Methoxy-4-hydroxy-benzonitrile;DTXSID20196070;EINECS 224-589-0;N-CYCLOPROPYL-N-ETHYLTHIOUREA;BBL036404;MFCD00001820;NSC158285;STK346864;AKOS000304372;4-Hydroxy-3-methoxybenzonitrile, 98%;CCG-302543;NSC 158285;NSC-158285;AS-15906;CS-0046224;FT-0618641;H0620;EN300-07946;J-200068;Z56963393;F0001-1204

Chemical Property of 4-Hydroxy-3-methoxybenzonitrile

Chemical Property:

• Appearance/Colour: beige crystalline powder
• Vapor Pressure: 0.00111mmHg at 25°C
• Melting Point: 85-87 °C(lit.)
• Refractive Index: 1.568
• Boiling Point: 291.559 °C at 760 mmHg
• PKA: 7.84±0.18(Predicted)
• Flash Point: 130.131 °C
• PSA: 53.25000
• Density: 1.245 g/cm³
• LogP: 1.27248
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.5
• 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:

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

Safty Information:

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

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C#N)O
• Uses: 4-Hydroxy-3-methoxybenzonitrile was used in the synthesis of 1,5-bis(4-cyano-2-methoxyphenoxy)-3-oxapentane.

Technology Process of 4-Hydroxy-3-methoxybenzonitrile

There total 31 articles about 4-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: 99.0%

vanillin (121-33-5,8014-42-4) → 3-methoxy-4-hydroxybenzonitrile (4421-08-3)

Guidance literature:

With phenoxyamine hydrochloride; In methanol; aq. phosphate buffer; water-d2; at 60 ℃; for 8h; pH=6.5;

DOI:10.1016/j.carres.2021.108282

Reference yield: 98.0%

vanillin oxime (2874-33-1) → 3-methoxy-4-hydroxybenzonitrile (4421-08-3)

Guidance literature:

With iron(III) chloride; silica gel; In neat (no solvent); at 110 ℃; for 1.5h; Concentration; Temperature; Catalytic behavior; Green chemistry;

DOI:10.1080/00397911.2016.1167910

Reference yield: 97.0%

4-bromo-3-methoxy-benzonitrile (120315-65-3) → 3-methoxy-4-hydroxybenzonitrile (4421-08-3)

Guidance literature:

With nickel(II) sulfate hexahydrate; 4,4'-Dimethoxy-2,2'-bipyridin; water; C₄₁H₄₀O₁₆; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; acetonitrile; at 20 ℃; for 24h; Schlenk technique; Irradiation; Inert atmosphere;

DOI:10.1016/j.jcat.2021.05.003

upstream raw materials:

4-cyano-2-methoxyphenyl acetate

vanillin

4-(benzyloxy)-3-methoxybenzonitrile

vanillin oxime

Downstream raw materials:

3,3'-dimethoxy-4,4'-hexanediyldioxy-di-benzonitrile

C₁₂H₁₅N₂O₃PS

C₁₂H₁₅N₂O₅P

3-methoxy-4-hydroxybenzoic acid

Refernces

• 1、 Cheewawisuttichai, Thamrongsak,Hurst, Robert D.,Brichacek, Matthew. "Transformation of aldehydes into nitriles in an aqueous medium using O-phenylhydroxylamine as the nitrogen source". . . Retrieved 2021/03/24.
• 2、 Guo, Baodang,Huang, Shuping,Li, Jia,Li, Min,Liu, Xuanzhong,Rao, Yijian,Wu, Yawen,Yin, Huimin,Yuan, Zhenbo,Zhang, Yan. "Discovery and characterization of a novel perylenephotoreductant for the activation of aryl halides". . p. 111 - 120. Retrieved 2021/06/16.