Guaiacol

Base Information

• Chemical Name: Guaiacol
• CAS No.: 90-05-1
• Molecular Formula: C7H8O2
• Molecular Weight: 124.139
• Hs Code.: 29095010
• European Community (EC) Number: 201-964-7,232-287-5
• ICSC Number: 0572
• NSC Number: 760376,3815
• UN Number: 1993
• UNII: 6JKA7MAH9C
• DSSTox Substance ID: DTXSID0023113
• Nikkaji Number: J3.217D
• Wikipedia: Guaiacol
• Wikidata: Q412403
• NCI Thesaurus Code: C76663
• RXCUI: 5031
• Metabolomics Workbench ID: 37774
• ChEMBL ID: CHEMBL13766
• Mol file: 90-05-1.mol

Synonyms:2-Hydroxy-Anisole;2-Hydroxyanisole;2-Methoxy-Phenol;2-Methoxyphenol;Catechol, Methyl;Guaiacol;Guaicol;Methyl Catechol

Chemical Property of Guaiacol

Chemical Property:

• Appearance/Colour: off-white crystals
• Vapor Pressure: 0.11 mm Hg ( 25 °C)
• Melting Point: 26-29 ºC(lit.)
• Refractive Index: 1.5430
• Boiling Point: 205 ºC at 760 mmHg
• PKA: 9.98(at 25℃)
• Flash Point: 82.2 ºC
• PSA: 29.46000
• Density: 1.109 g/cm³
• LogP: 1.40080
• Storage Temp.: Refrigerator
• Sensitive.: Air Sensitive
• Solubility.: H2O: insoluble
• Water Solubility.: 17 g/L (15 ºC)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 124.052429494
• Heavy Atom Count: 9
• Complexity: 83

Purity/Quality:

98% ^*data from raw suppliers

2-Methoxyphenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T,Xi
• Hazard Codes: Xn,T,Xi
• Statements: 22-36/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: UVCB,Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: COC1=CC=CC=C1O
• Recent ClinicalTrials: Research of the Application of Triple Antibiotic Paste in Primary Teeth With Pericpical Periodontitis
• Inhalation Risk: A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C , especially on spraying.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. Exposure to sun may enhance the irritating effect of this substance. This may result in burns. Ingestion could cause death. Medical observation is indicated.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis and hyperpigmentation of skin. This substance is probably carcinogenic to humans.
• Uses: Guaiacol is a precursor of vanillin and santalidol (a synthetic sandal- wood fragrance). it is obtained from wood tar by the destructive distillation of hardwood, by the distillation of the phenol fraction of coal tar, or through the use of o-dichlorobenzene. it is processed to yield vanillin. Synthetic flavors, medicine (expectorant). A phenolic natural product and reducing co-substrate for COX reactions.

Technology Process of Guaiacol

There total 880 articles about Guaiacol 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%

2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-ol → 2-methoxy-phenol (90-05-1) + 1-(4-methoxyphenyl)ethanone (100-06-1)

Guidance literature:

With sodium tetrahydroborate; palladium on activated charcoal; In water; ethyl acetate; at 80 ℃; for 1h;

DOI:10.1002/cssc.201500117

Reference yield: 91.0%

p-methoxyphenacyl acetate (58518-78-8) → 2-methoxy-phenol (90-05-1) + 1-(4-methoxyphenyl)ethanone (100-06-1)

Guidance literature:

With formic acid; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 18h; Inert atmosphere; Irradiation;

DOI:10.1021/acscatal.7b01010

Reference yield: 40.0%

perbenzoyl p-nitrophenyl carbonate (42464-09-5) + methoxybenzene (100-66-3) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 4-methoxyphenyl benzoate (1523-19-9) + 2-methoxyphenyl benzoate (531-37-3) + 4-methoxy-phenol (150-76-5) + 2-methoxy-phenol (90-05-1) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With trifluoroacetic acid; at 70 ℃; for 60h; Product distribution; Mechanism; influence of temperature, reagent;

DOI:10.1021/ja00405a043

upstream raw materials:

emetine

(+-)-Emetin

tetrahydrofuran

n-butyl magnesium bromide

Downstream raw materials:

2-(2-methoxyphenoxy)ethanol

2-Methoxy-6-piperidinomethyl-phenol

nicotinic acid-(2-methoxy-phenyl ester)

2-methoxyphenyl furan-2-carboxylate

Refernces

• 1、 Duran-Giner, Neus,Encinas, Susana,Miranda, Miguel A.. "Solar filters as feasible acceptors of atomic oxygen". . p. 725 - 728. Retrieved 2013.
• 2、 Bridger. "-". . p. 1174,1179. Retrieved 1938.
• 3、 Oussaid, Abdelouahad,Thach, Le Ngoc,Loupy, Andre. "Selective dealkylations of alkyl aryl ethers in heterogeneous basic media under microwave irradiation". . p. 2451 - 2454. Retrieved 1997.
• 4、 Sahakari,Mukhedkar. "-". . p. 888,889-892. Retrieved 1971.
• 5、 Martos, Mario,Pastor, Isidro M.. "Imidazolium-urea low transition temperature mixtures for the UHP-promoted oxidation of boron compounds". . . Retrieved 2022/01/03.
• 6、 Guo, Tao,He, Jianghua,Liu, Tianwei,Zhang, Yuetao. "One-Pot Transformation of Lignin and Lignin Model Compounds into Benzimidazoles". supporting information. . Retrieved 2022/02/07.