| Identification | More | [Name]
p-Cresol | [CAS]
106-44-5 | [Synonyms]
1-HYDROXY-4-METHYLBENZENE
4-HYDROXYTOLUENE
4-METHYLPHENOL
AKOS BBS-00004354
FEMA 2337
METHYL PHENOL
P-CRESOL
P-CRESYLIC ACID
P-HYDROXYTOLUENE
P-METHYLPHENOL
1-Methyl-4-hydroxybenzene
4-Cresol
4-methyl-pheno
CRESOL, PARA
cresol,para-isomer
femanumber2337
Paracresol
para-cresol
para-cresolsaka
para-cresylicacid | [EINECS(EC#)]
203-398-6 | [Molecular Formula]
C7H8O | [MDL Number]
MFCD00002376 | [Molecular Weight]
108.14 | [MOL File]
106-44-5.mol |
| Chemical Properties | Back Directory | [Appearance]
Cresol is a mixture of the three isomeric cresols, o-, m-, and p-cresol. Cresols are slightly soluble in water. m-Isomer: Colorless or yellow liquid with characteristic odor. | [Melting point ]
32-34 °C(lit.)
| [Boiling point ]
202 °C(lit.)
| [density ]
1.034 g/mL at 25 °C(lit.)
| [vapor density ]
3.72 (vs air)
| [vapor pressure ]
1 mm Hg ( 20 °C)
| [FEMA ]
2337 | [refractive index ]
nD20 1.5395 | [Fp ]
193 °F
| [storage temp. ]
2-8°C
| [solubility ]
20g/l | [form ]
Crystalline Solid or Liquid | [pka]
10.17(at 25℃) | [color ]
Colorless to light yellow, may darken on exposure to light | [Specific Gravity]
1.0341 (20/4℃) | [Odor]
at 0.10 % in dipropylene glycol. phenolic narcissus animal mimosa | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents. Air and light-sensitive. Hygroscopic. | [explosive limit]
1%(V) | [Odor Threshold]
0.000054ppm | [Odor Type]
phenolic | [Water Solubility ]
20 g/L (20 ºC) | [Sensitive ]
Light Sensitive | [Usage]
Intermediates of Liquid Crystals | [JECFA Number]
693 | [Merck ]
14,2579 | [BRN ]
1305151 | [Henry's Law Constant]
6.17 at 20.00 °C, 9.31 at 25.00 °C (dynamic equilibrium system-GC, Feigenbrugel et al., 2004a) | [Dielectric constant]
5.6（21.0℃） | [Exposure limits]
NIOSH REL: TWA 2.3 ppm (10 mg/m3), IDLH 250 ppm; OSHA PEL: TWA 5
ppm (22 mg/m3); ACGIH TLV: TWA for all isomers 5 ppm (adopted). | [LogP]
1.94 | [CAS DataBase Reference]
106-44-5(CAS DataBase Reference) | [NIST Chemistry Reference]
Phenol, 4-methyl-(106-44-5) | [EPA Substance Registry System]
106-44-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T,Xi | [Risk Statements ]
R24/25:Toxic in contact with skin and if swallowed .
R34:Causes burns.
R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
UN 3455 6.1/PG 2
| [WGK Germany ]
1
| [RTECS ]
GO6475000
| [F ]
8 | [Autoignition Temperature]
555 °C | [Hazard Note ]
Irritant | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29071200 | [Safety Profile]
Poison by ingestion,
skin contact, subcutaneous, intravenous, and
intraperitoneal routes. A severe skin and eye
irritant. Questionable carcinogen with
experimental neoplastigenic data by itself
and with 7,12-dirnethyl benz(a)anthracene.
Combustible when exposed to heat or
flame. Moderately explosive in the form ofvapor when exposed to heat or flame. To
fight fire, use CO2, dry chemical, alcohol
foam. See also other cresol entries and
PHENOL. | [Hazardous Substances Data]
106-44-5(Hazardous Substances Data) |
| Hazard Information | Back Directory | [General Description]
Colorless solid with a tar like odor. Sinks and mixes slowly with water. | [Reactivity Profile]
P-CRESOL(106-44-5) is sensitive to heat. P-CRESOL(106-44-5) is also sensitive to light. This chemical is incompatible with strong oxidizers and strong alkalis. P-CRESOL(106-44-5) will attack some forms of plastics, coatings and rubber. | [Air & Water Reactions]
Insoluble in water. | [Hazard]
Questionable carcinogen. | [Health Hazard]
INHALATION: Irritation of nose or throat. EYES: Intense irritation and pain, swelling of conjunctiva and corneal damage may occur. SKIN: Intense burning, loss of feeling, white discoloration and softening. Gangrene may occur. INGESTION: Burning sensation in mouth and esophagus. Vomiting may result. Absorption by all routes may cause muscular weakness, gastroenteric disturbance, severe depression and collapse. Effects are primarily on central nervous system, edema of lungs, injury of spleen and pancreas may occur. | [Potential Exposure]
Cresol is used as a disinfectant and fumigant; as an ore flotation agent, and as an intermediate in the manufacture of chemicals, dyes, plastics, and antioxidants. A mixture of isomers is generally used; the concentrations of the components are determined by the source of the cresol. | [First aid]
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. Medical observation is recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema Cresols 931 may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy | [Shipping]
UN2076 Cresols, liquid, Hazard class: 6.1; Labels: 6.1-Poisonous materials, 8-Corrosive material. UN3455 Cresols, solid, Hazard class: 6.1; Labels: 6.1- Poisonous materials, 8-Corrosive material. | [Incompatibilities]
Vapors may form explosive mixture with air. Incompatible with strong acids; oxidizers, alkalies, aliphatic amines; amides, chlorosulfonic acid; oleum. Decomposes on heating, producing strong acids and bases, causing fire and explosion hazard. Liquid attacks some plastics and rubber. Attacks many metals. | [Waste Disposal]
Wastewaters may be subjected to biological treatment. Concentrations may be further reduced by ozone treatment. High concentration wastes may be destroyed in special waste incinerators. | [Physical properties]
Colorless to pink crystals with a phenolic odor. Odor threshold concentration in water is 55 ppb
(Buttery et al., 1988). An experimentally determined odor threshold concentration of 1 ppbv was
reported by Leonardos et al. (1969) which exceeds the odor threshold concentration of 0.054 ppbv
reported by Nagata and Takeuchi (1990). | [Occurrence]
Has been found in a score of essential oils including ylang ylang and oil of jasmine (Gildemeister & Hoffman, 1966). | [Definition]
ChEBI: A cresol that consists of toluene substituted by a hydroxy group at position 4. It is a metabolite of aromatic amino acid metabolism produced by intestinal microflora in humans and animals. | [Preparation]
It can be prepared by fractional distillation of coal tar where it occurs together with the ortho- and para- isomers. | [Production Methods]
The cresols (cresylic acids) are methyl phenols and generally
appear as a mixture of isomers. p-Cresol is a 4-methyl
derivative of phenol and is prepared from m-toluic acid
or obtained from coal tar or petroleum. Crude
cresol is obtained by distilling “gray phenic acid” at a
temperature of ～180–201°C. p-Cresol may be separated
from the crude or purified mixture by repeated fractional
distillation in vacuo. It can also be prepared synthetically by
diazotization of the specific toluene or by fusion of the
corresponding toluenesulfonic acid with sodium hydroxide. | [Aroma threshold values]
Detection: 55 to 100 ppb. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 81, p. 4230, 1959 DOI: 10.1021/ja01525a028
Chemical and Pharmaceutical Bulletin, 31, p. 749, 1983 DOI: 10.1248/cpb.31.749
Tetrahedron Letters, 21, p. 3731, 1980 DOI: 10.1016/0040-4039(80)80164-X | [Flammability and Explosibility]
Notclassified | [Carcinogenicity]
o-Cresol has been induced a few
papillomas but no carcinomas in tumor studies. | [Source]
As 3+4-methylphenol, detected in distilled water-soluble fractions of 87 octane gasoline
(6.03 mg/L), 94 octane gasoline (0.60 mg/L), Gasohol (1.76 mg/L), No. 2 fuel oil (1.84 mg/L), jet
fuel A (0.43 mg/L), diesel fuel (1.318 mg/L), and military jet fuel JP-4 (0.92 mg/L) (Potter, 1996).
A high-temperature coal tar contained 4-methylphenol at an average concentration of 0.27 wt %
(McNeil, 1983).
Occurs naturally in brown juniper, Spanish cedar, peppermint (2 to 20 ppb), tarragon, asparagus
shoots, ylang-ylang, jasmine, tea leaves, coffee beans, Japanese privet, white mulberries,
raspberries, vanilla, blueberries, sour cherries, anise, and tamarind (Duke, 1992).
A liquid swine manure sample collected from a waste storage basin contained 4-methylphenol
at a concentration of 4.9 mg/L (Zahn et al., 1997). | [Environmental Fate]
Biological. Protocatechuic acid (3,4-dihydroxybenzoic acid) is the central metabolite in the
bacterial degradation of 4-methylphenol. Intermediate by-products include 4-hydroxybenzyl
alcohol, 4-hydroxybenzaldehyde, and 4-hydroxybenzoic acid. In addition, 4-methylphenol may
undergo hydroxylation to form 4-methylcatechol (Chapman, 1972). Chloroperoxidase, a fungal
enzyme isolated from Caldariomyces fumago, reacted with 4-methylphenol forming 4-methyl-2-
chlorophenol (Wannstedt et al., 1990). Under methanogenic conditions, inocula from a municipal sewage treatment plant digester degraded 4-methylphenol to phenol prior to being mineralized to
carbon dioxide and methane (Young and Rivera, 1985).
Photolytic. Photooxidation products reported include 2,2′-dihydroxy-4,4′-dimethylbiphenyl, 2-
hydroxy-3,4′-dimethylbiphenyl ether, and 4-methylcatechol (Smith et al., 1978). Anticipated
products from the reaction of 4-methylphenol with ozone or OH radicals in the atmosphere are
hydroxynitrotoluene and ring cleavage compounds (Cupitt, 1980). Absorbs UV light at a
maximum wavelength of 278 nm (Dohnal and Fenclová, 1995).
Chemical/Physical. Kanno et al. (1982) studied the aqueous reaction of 4-methylphenol and
other substituted aromatic hydrocarbons (toluidine, 1-naphthylamine, phenol, 2- and 3-
methylphenol, pyrocatechol, resorcinol, hydroquinone, and 1-naphthol) with hypochlorous acid in
the presence of ammonium ion. They reported that the aromatic ring was not chlorinated as
expected but was cleaved by chloramine forming cyanogen chloride. The amount of cyanogen
chloride formed was increased as the pH was lowered (Kanno et al., 1982). | [Metabolism]
p-Cresol is oxidized at the methyl group in both dogs and rabbits to yield ρ-hydroxybenzoic acid. In the rabbit up to 10% of oral doses of 0.25-0.5 g is excreted as free and conjugated p-hydroxybenzoic acid (Williams, 1959). | [Purification Methods]
It can be separated from m-cresol by fractional crystalisation of its melt. Purify it by distillation, by precipitation from *benzene solution with pet ether, and via its benzoate, as for phenol. Dry it under vacuum over P2O5. It has also been crystallised from pet ether (b 40-60o) and by conversion to sodium p-cresoxyacetate which, after crystallisation from water is decomposed by heating with HCl in an autoclave [Savard Ann Chim (Paris) 11 287 1929]. The 3,5-dinitrobenzoate (prepared with 3,5-dinitrobenzoyl chloride in dry pyridine, and recrystallised from EtOH or aqueous Me2CO) has m 189o. [Beilstein 6 II 2093.] |
| Questions And Answer | Back Directory | [description]
p-Cresol is a low-molecular-weight compound, is a starting material in the synthesis of bupranolol which is a non-selective beta blocker.
p-cresol is found in extracts from the plants Mentha pulegium and Hedeoma pulegioides, commonly known as pennyroyal oil and pennyroyal tea. These extracts are popular as unconventional herbal therapeutic agents and are applied as abortiva, diaphoretics, emmenagogues, and psychedelic drugs. Pennyroyal oil is extensively used for its pleasant mint-like smell in the flavoring industry.
It is also used in the production of antioxidants like butylated hydroxytoluene. Furthermore, it is used as an adhesive and a sealant in chemicals, dyes, intermediates, odor agents, plasticizers, plating agents and surface treating agents. It acts as an antioxidant and a disinfectant in pharmaceuticals. | [Chemical properties]
It appears as colorless to pink crystal with smoked and herbal smell. The relative density (d420) is 1.0178; the refractive index (nD20) is 1.5312; the melting point is 34.8 °C; the boiling point is 201.9 °C and the flash point is 86.1 °C. It is soluble in water (2.3%/40 ℃), easily soluble in caustic soda and common organic solvents.
Natural products exist in ylang oil, strawberry, cheese, coffee and cocoa and so on. | [Uses]
1. It can be used as germicide, fungicide. Used for organic Synthesis.
2. This product is the raw material for the manufacture of antioxidant 2,6-di-tert-butyl-p-cresol and rubber antioxidant. At the same time, it is also an important fundamental raw material for the production of pharmaceutical TMP and dyes para-Cresidine sulfonic acid.
3. P-cresol is the intermediate for the manufacturing of fungicide methylphosophos, an insecticide flufenvalerate, and Etofenprox, but also the intermediate of antioxidant additives 2, 6-di-tert-butyl-4-methyl phenol and p-hydroxybenzene formaldehyde.
4. It can be used as raw materials for the preparation of antioxidant 264 (2, 6-di-tert-butyl-p-cresol) and rubber antioxidant. In the plastics industry, it can produce phenolic resin and plasticizer. In medicine, it can be used as a disinfectant. In addition, it can be used as the raw materials of dyes and pesticides. | [Production method]
Production method of p-Cresol: sulfonate toluene with sulfuric acid to get p-toluenesulfonic acid, after cooling, crystallization, filtration, and then add sodium sulfite to neutralize to get sodium p-toluenesulfonate, and then sodium hydroxide alkaline melting to get sodium p-toluene phenol, and then acidified by sulfurous acid to become. Finally, it is separated by distillation and crystallization. | [Toxicity]
Central nervous system: toxic effects with being fatal in severe cases.
LD50:1800 mg/kg (rat, oral);
As fragrances, it can be safely used in food (FDA, §172.515, 2000);
GRAS (FEMA). |
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