Catechol

Base Information

• Chemical Name: Catechol
• CAS No.: 120-80-9
• Deprecated CAS: 16474-89-8,16474-90-1,37349-32-9,16474-90-1,37349-32-9
• Molecular Formula: C6H6O2
• Molecular Weight: 110.112
• Hs Code.: 2907 29 00
• European Community (EC) Number: 204-427-5
• ICSC Number: 0411
• NSC Number: 1573
• UN Number: 2811
• UNII: LF3AJ089DQ
• DSSTox Substance ID: DTXSID3020257
• Nikkaji Number: J2.921A
• Wikipedia: Catechol
• Wikidata: Q282440
• NCI Thesaurus Code: C28138
• Metabolomics Workbench ID: 37520
• ChEMBL ID: CHEMBL280998
• Mol file: 120-80-9.mol

Synonyms:1,2-benzenediol;1,2-dihydroxybenzene;1,3-dihydroxybenzene;2-hydroxyphenol;catechol;catechol dipotassium salt;catechol sodium salt;catechol, 14C-labeled cpd;pyrocatechol

Chemical Property of Catechol

Chemical Property:

• Appearance/Colour: off-white powder
• Vapor Pressure: 1 mm Hg ( 75 °C)
• Melting Point: 103-106 ºC
• Refractive Index: 1.612
• Boiling Point: 245.5 ºC at 760 mmHg
• PKA: 9.85(at 20℃)
• Flash Point: 137.2 ºC
• PSA: 40.46000
• Density: 1.275 g/cm³
• LogP: 1.09780
• Storage Temp.: Store at RT.
• Sensitive.: Air & Light Sensitive
• Solubility.: 430g/l
• Water Solubility.: 430 g/L (20 ºC)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 110.036779430
• Heavy Atom Count: 8
• Complexity: 62.9
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Catechol 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 21/22-36/38-68-43
• Safety Statements: 22-26-37-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Phenols
• Canonical SMILES: C1=CC=C(C(=C1)O)O
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the skin and respiratory tract. The substance is corrosive to the eyes. The substance may cause effects on the central nervous system. This may result in depression, convulsions and respiratory failure. Exposure could cause rise of blood pressure.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. This substance is possibly carcinogenic to humans. May cause heritable genetic damage to human germ cells.
• Uses: Pyrocatechol is used in photography, in dyeing fur, and as a topical antiseptic. In photography; dyeing fur; as reagent. In the manufacture of rubber antioxidants and monomer inhibitors to stop radical polymerization; in dyes, as a photographic developer; in formulations for pharmaceuticals, perfumes, inks, and insecticides

Technology Process of Catechol

There total 629 articles about Catechol 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: 2.0%

phenol (108-95-2,27073-41-2) → 2,2'-dihydroxybiphenyl (1806-29-7) + benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) + hydroquinone (123-31-9,8027-02-9)

Guidance literature:

With 3,10-di-n-butylisoalloxazine N-oxide; In acetonitrile; for 6h; Yields of byproduct given; Irradiation;

DOI:10.1039/P19900003339

Reference yield:

phenol (108-95-2,27073-41-2) → o-Phenoxyphenol (2417-10-9) + 2,2'-dihydroxybiphenyl (1806-29-7) + cis,cis-Muconic acid (1119-72-8) + 2,4'-dihydroxybiphenyl (611-62-1) + benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) + hydroquinone (123-31-9,8027-02-9)

Guidance literature:

With sodium hydroxide; ozone; at 0 - 20 ℃; Kinetics; Mechanism; Product distribution; dependence from NaOH concn.;

DOI:10.1007/BF00965412

Reference yield:

phenol (108-95-2,27073-41-2) → 2,2'-dihydroxybiphenyl (1806-29-7) + cis,cis-Muconic acid (1119-72-8) + benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) + 4,6-dioxo-2-hexenoic acid (121259-83-4) + hydroquinone (123-31-9,8027-02-9) + p-benzoquinone (106-51-4)

Guidance literature:

With ozone; In water; at 19.9 ℃; Mechanism; Product distribution; Kinetics; other solvents; other phenols;

DOI:10.1007/BF00965413

upstream raw materials:

2-acetylpropanoic acid ethyl ester

Methylenedioxybenzene

1,3-benzodioxol-2-one

o-toluidine

Downstream raw materials:

1-(2,3-dihydroxy-phenyl)-pyridinium; bromide

phenol 2-[(tetrahydro-2H-pyran-2yl)oxy]

1,2-bis-tetrahydropyran-2-yloxy-benzene

hystazarin

Refernces

• 1、 Richardson, Amie M.,Chen, Chun-Hsing,Snider, Barry B.. "Synthesis of methyl 1-hydroxy-6-oxo-2-cyclohexenecarboxylate, a component of salicortin and tremulacin, and the monomer of idesolide". . p. 8099 - 8102. Retrieved 2007.
• 2、 Woodward,Ebert. "". . p. 1666. Retrieved 1948.
• 3、 Guarneri, Alice,Westphal, Adrie H.,Leertouwer, Jos,Lunsonga, Joy,Franssen, Maurice C. R.,Opperman, Diederik J.,Hollmann, Frank,van Berkel, Willem J. H.,Paul, Caroline E.. "Flavoenzyme-mediated Regioselective Aromatic Hydroxylation with Coenzyme Biomimetics". . p. 1368 - 1375. Retrieved 2020.
• 4、 Nematollahi, Davood,Workentin, Mark S.,Tammari, Esmail. "Electrochemical oxidation of catechol in the presence of cyclopentadiene. Investigation of electrochemically induced Diels-Alder reactions". . p. 1631 - 1633. Retrieved 2006.
• 5、 Chen, Hong Li,Li, Shang Wei,Wang, Yi Meng. "Synthesis and catalytic properties of multilayered MEL-type titanosilicate nanosheets". . p. 5889 - 5900. Retrieved 2015.
• 6、 Potekhin,Kulikova,Vasil'Ev,Kohina,Potekhin. "Hydroxylation of phenol with hydrogen peroxide in protic and aprotic solvents on TS-1 catalyst". . p. 640 - 648. Retrieved 2011.
• 7、 Jones et al.. "-". . p. 1051,1052-1054. Retrieved 1965.
• 8、 Machovina, Melodie M.,Mallinson, Sam J.B.,Knott, Brandon C.,Meyers, Alexander W.,Garcia-Borràs, Marc,Bu, Lintao,Gado, Japheth E.,Oliver, April,Schmidt, Graham P.,Hinchen, Daniel J.,Crowley, Michael F.,Johnson, Christopher W.,Neidle, Ellen L.,Payne, Christina M.,Houk, Kendall N.,Beckham, Gregg T.,McGeehan, John E.,DuBois, Jennifer L.. "Enabling microbial syringol conversion through structure-guided protein engineering". . p. 13970 - 13976. Retrieved 2019.
• 9、 Sutar, Alekha Kumar,Das, Yasobanta,Pattnaik, Sasmita,Routaray, Anita,Nath, Nibedita,Rath, Prasanta,Maharana, Tungabidya. "Novel polystyrene-anchored zinc complex: Efficient catalyst for phenol oxidation". . p. 1701 - 1708. Retrieved 2014.
• 10、 Shao, Wenjie,Clive, Derrick L.J.. "A Family of Routes to Substituted Phenols, Including Meta-Substituted Phenols". . p. 12280 - 12287. Retrieved 2015.