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Catechol information


Catechol
Skeletal formula
Pyrocatechol
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
Benzene-1,2-diol[1]
Other names
Pyrocatechol[1]
1,2-Benzenediol
2-Hydroxyphenol
1,2-Dihydroxybenzene
o-Benzenediol
o-Dihydroxybenzene
Identifiers
CAS Number
  • 120-80-9 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
471401
ChEBI
  • CHEBI:18135 checkY
ChEMBL
  • ChEMBL280998 checkY
ChemSpider
  • 13837760 checkY
DrugBank
  • DB02232
ECHA InfoCard 100.004.025 Edit this at Wikidata
EC Number
  • 204-427-5
Gmelin Reference
2936
KEGG
  • C00090 checkY
PubChem CID
  • 289
RTECS number
  • UX1050000
UNII
  • LF3AJ089DQ checkY
CompTox Dashboard (EPA)
  • DTXSID3020257 Edit this at Wikidata
SMILES
  • Oc1c(O)cccc1
Properties
Chemical formula
C6H6O2
Molar mass 110.112 g·mol−1
Appearance white to brown feathery crystals
Odor faint, phenolic odor
Density 1.344 g/cm3, solid
Melting point 105 °C (221 °F; 378 K)
Boiling point 245.5 °C (473.9 °F; 518.6 K) (sublimes)
Solubility in water
312 g/L at 20 °C[2]
Solubility very soluble in pyridine
soluble in chloroform, benzene, CCl4, ether, ethyl acetate
log P 0.88
Vapor pressure 20 Pa (20 °C)
Acidity (pKa) 9.45, 12.8
Magnetic susceptibility (χ)
−6.876×10−5 cm3/mol
Refractive index (nD)
1.604
Dipole moment
2.62±0.03 D [3]
Structure
Crystal structure
monoclinic
Thermochemistry
Std enthalpy of
formation fH298)
−354.1 kJ·mol−1
Enthalpy of fusion fHfus)
22.8 kJ·mol−1 (at melting point)
Hazards
GHS labelling:
Pictograms
GHS06: ToxicGHS08: Health hazardGHS05: Corrosive
Signal word
Danger
Hazard statements
H301, H311, H315, H317, H318, H332, H341
Precautionary statements
P261, P301, P302, P305, P310, P312, P330, P331, P338, P351, P352
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
Flash point 127 °C (261 °F; 400 K)
Autoignition
temperature
510 °C (950 °F; 783 K)
Explosive limits 1.4%–?[4]
Lethal dose or concentration (LD, LC):
LD50 (median dose)
300 mg/kg (rat, oral)
NIOSH (US health exposure limits):
PEL (Permissible)
none[4]
REL (Recommended)
TWA 5 ppm (20 mg/m3) [skin][4]
IDLH (Immediate danger)
N.D.[4]
Safety data sheet (SDS) Sigma-Aldrich
Related compounds
Related benzenediols
Resorcinol
Hydroquinone
Related compounds
1,2-benzoquinone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Catechol (/ˈkætɪɒl/ or /ˈkætɪkɒl/), also known as pyrocatechol or 1,2-dihydroxybenzene, is an organic compound with the molecular formula C6H4(OH)2. It is the ortho isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amounts. It was first discovered by destructive distillation of the plant extract catechin. About 20,000 tonnes of catechol are now synthetically produced annually as a commodity organic chemical, mainly as a precursor to pesticides, flavors, and fragrances. Small amounts of catechol occur in fruits and vegetables.[2]

  1. ^ a b "Front Matter". Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 691. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ a b Cite error: The named reference Ullmann was invoked but never defined (see the help page).
  3. ^ Lander, John J.; Svirbely, W. J. (1945). "The Dipole Moments of Catechol, Resorcinol and Hydroquinone". Journal of the American Chemical Society. 67 (2): 322–324. doi:10.1021/ja01218a051.
  4. ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0109". National Institute for Occupational Safety and Health (NIOSH).

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