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| | Catechol Basic information |
| | Catechol Chemical Properties |
| Melting point | 100-103 °C (lit.) | | Boiling point | 245 °C (lit.) | | density | 1,371 g/cm3 | | vapor density | 3.8 (vs air) | | vapor pressure | 1 mm Hg ( 75 °C) | | refractive index | 1.6120 (estimate) | | Fp | 279 °F | | storage temp. | Store below +30°C. | | solubility | 430g/l | | form | Crystalline Flakes | | pka | 9.85(at 20℃) | | color | white to faintly beige | | PH | 6 (100g/l, H2O, 20℃) | | explosive limit | 1.97%(V) | | Water Solubility | 430 g/L (20 ºC) | | Sensitive | Air & Light Sensitive | | Merck | 14,7999 | | BRN | 471401 | | Exposure limits | TLV-TWA 5 ppm (～22 mg/m3) (ACGIH). . | | Stability: | Stable. Substances to be avoided include acid chlorides, acid anhydrides, bases, oxidizing agents, nitric acid. Light sensitive; may discolour on exposure to air. Combustible. | | LogP | 0.93 | | CAS DataBase Reference | 120-80-9(CAS DataBase Reference) | | NIST Chemistry Reference | 1,2-Benzenediol(120-80-9) | | IARC | 2B (Vol. 15, Sup 7, 71) 1999 | | EPA Substance Registry System | Catechol (120-80-9) |
| | Catechol Usage And Synthesis |
| Chemical Properties | Off-white powder | | Chemical Properties | Catechol also called Pyrocatechol is a white crystalline solid. Turns
brown on contact with light and air. | | Uses | Catechol is used in photography, in dyeing fur, and as a topical antiseptic. | | Uses | 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 | | Uses | In photography; dyeing fur; as reagent. | | Definition | A colourless crystalline
PHENOL containing two hydroxyl groups. It
is used in photographic developing. | | Production Methods | Catechol may be obtained by the fusion of o-phenolsulfonic
acid with alkali, by heating chorophenol with a
solution of sodium hydroxide at 200°C in an autoclave, or
by cleavage of the methyl ether group of guaiacol (obtained
from beechwood tar) with hydriodic acid. | | Synthesis Reference(s) | The Journal of Organic Chemistry, 45, p. 4275, 1980 DOI: 10.1021/jo01310a003 | | General Description | Solid; white; odorless. Sinks and mixes with water. | | Air & Water Reactions | Turns brown on exposure to air and light, especially when moist. Water soluble. Aqueous solutions soon turn brown on exposure to air and light. | | Reactivity Profile | POISONOUS GASES MAY BE PRODUCED WHEN HEATED. Pyrocatechol may form toxic fumes at high temperatures. [USCG, 1999]. Pyrocatechol can react with acid chlorides, acid anhydrides, bases and oxidizing agents. Pyrocatechol reacts violently on contact with concentrated nitric acid. Pyrocatechol acts as a reducing agent . | | Hazard | Strong irritant. Toxic by skin absorption.
Eye and upper respiratory tract irritant, and der-
matitis. Possible carcinogen.
| | Health Hazard | Acute oral and percutaneous toxicity of pyrocatechol is greater than that of phenol; inhalation toxicity is less than that of phenol. The toxic symptoms include weakness, muscular pain, dark urine, tremor, dyspnea, and convulsions. Large amounts can produce degenerative changes in renal tubules. Large doses can cause death due to respiratory failure. Skin contact can cause eczematous dermatitis.
LD50 value, oral (rats): 260 mg/kg
LD50 value, skin (rabbits): 800 mg/kg. | | Health Hazard | DUST: Irritating to eyes, nose and throat. If inhaled will cause coughing or difficult breathing. SOLID: Will burn skin and eyes. Harmful if swallowed. | | Fire Hazard | Combustible. POISONOUS GASES MAY BE PRODUCED WHEN HEATED. May form toxic fumes at high temperatures. | | Flammability and Explosibility | Nonflammable | | Safety Profile | Poison by ingestion,
subcutaneous, intraperitoneal, intravenous,
and parenteral routes. Moderately toxic by
skin contact. Experimental reproductive
effects. Can cause dermatitis on skin
contact. An allergen. Human mutation data
reported. Questionable carcinogen. Systemic
effects sirmlar to those of phenol.
Combustible when exposed to heat or
flame; can react vigorously with oxidizing
materials. Hypergolic reaction with
concentrated nitric acid. To fight fire, use
water, CO2, dry chemical. When heated to
decomposition it emits acrid smoke and
irritating fumes. See also PHENOL. | | Potential Exposure | Used as a chemical intermediate;
pharmaceutical and veterinary drug; as an antiseptic; in
photography; in dyestuff manufacture and application. It is
also used in electroplating, in the formulation of specialty
inks; in antioxidants; and light stabilizers. | | Carcinogenicity | Catechol has been extensively
studied for its role in carcinogenesis of the rat glandular
stomach; it was concluded that pyrocatechol is
carcinogenic. When rats and mice were administered
0.8% pyrocatechol in their feed for life, there was an increase
in glandular stomach adenocarcinoma in both male and
female rats. Pyrocatechol also caused hyperplasia of the
glandular stomach in both rats and mice, a mechanism
that could cause promotion of carcinogen-initiated
cells; no effects on the esophagus or urinary bladder
were reported. There were no cutaneous neoplasms when
pyrocatechol was applied in dermal studies. Catechol
may be classified as a cocarcinogen because it enhanced the
number and/or incidence of lesions in the stomach induced
by several carcinogenic nitrosamines and cutaneous neoplasms
when administered dermally together with several
carcinogens. | | Shipping | UN 2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required. | | Purification Methods | Crystallise catechol from *benzene or toluene and sublime it in vacuo. [Rozo et al. Anal Chem 58 2988 1986, Beilstein 6 IV 5557.] | | Incompatibilities | Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides. |
| | Catechol Preparation Products And Raw materials |
| Raw materials | Hydrogen peroxide-->Phenol-->Chlorosulfonic acid-->2-Butanone-->Cyclohexanone-->Hydroquinone-->4-Methyl-2-pentanone-->Guaiacol-->Montmorillonite K10-->2-Chlorophenol-->CREOSOTE-->Protocatechuic acid-->2-Methoxy-4-methylphenol | | Preparation Products | Hydroquinone-->Carbofuran-->Ethyl vanillin-->Piperonyl aldehyde-->Propoxur-->2,3-Dihydro-2,2-dimethyl-7-benzofuranol-->4'-FORMYLBENZO-15-CROWN 5-ETHER-->1,3-Benzodioxole-->DIETHOFENCARB-->2-(5-BROMO-2-PYRIDYLAZO)-5-(DIETHYLAMINO)PHENOL-->1,2-Dimethoxybenzene-->2,3-DIHYDRO-1,4-BENZODIOXINE-2-CARBONYL CHLORIDE-->4-tert-Butylcatechol-->1-Bromo-1-cyclopentene-->O-BROMANIL-->3,4-(Methylenedioxy)phenylacetonitrile-->Benzo-15-crown-5-->1,2-Diethoxybenzene-->2-Isopropoxyphenol-->[[o-(allyloxy)phenoxy]methyl]oxirane-->2-[(2-METHYL-2-PROPENYL)OXY]-PHENOL-->PIPERONYL FORMALDEHYDE-->BENZO[1,3]DIOXOLE-5-SULFONYL CHLORIDE-->2,3-DIHYDRO-1,4-BENZODIOXIN-2-METHANOL 4-METHYLBENZENESULFONATE-->2-Chloro-3',4'-dihydroxyacetophenone-->CATECHOLBORANE-->Piperonyl chloride-->2-(Allyloxy)phenol-->2-HYDROXYMETHYL-1,4-BENZODIOXANE-->1-Iodoheptane-->Pyrocatechol Violet-->Adrenalone-->1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino]ethan-1-one-->4-BROMOCATECHOL-->Isoproterenol |
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