description Chemical properties Uses Production method Toxicity
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p-Cresol

description Chemical properties Uses Production method Toxicity
Product Name
p-Cresol
CAS No.
106-44-5
Chemical Name
p-Cresol
Synonyms
4-METHYLPHENOL;para-cresol;P-HYDROXYTOLUENE;4-Cresol;P-METHYLPHENOL;p-Tolyl alcohol;Paracresol;Phenol,4-methyl-;Paramethyl phenol;p-Cresol, extra pure
CBNumber
CB5453502
Molecular Formula
C7H8O
Formula Weight
108.14
MOL File
106-44-5.mol
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p-Cresol Property

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)
refractive index 
nD20 1.5395
FEMA 
2337 | P-CRESOL
Flash point:
193 °F
storage temp. 
Store below +30°C.
solubility 
20g/l
pka
10.17(at 25℃)
form 
Crystalline Solid or Liquid
Specific Gravity
1.0341 (20/4℃)
color 
Colorless to light yellow, may darken on exposure to light
Odor
at 0.10 % in dipropylene glycol. phenolic narcissus animal mimosa
Odor Type
phenolic
Odor Threshold
0.000054ppm
explosive limit
1%(V)
Water Solubility 
20 g/L (20 ºC)
Sensitive 
Light Sensitive
Merck 
14,2579
JECFA Number
693
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)
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).
Dielectric constant
5.6（21.0℃）
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents. Air and light-sensitive. Hygroscopic.
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
p-Cresol (106-44-5)
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Safety

Hazard Codes 
T,Xi
Risk Statements 
24/25-34-39/23/24/25-23/24/25
Safety Statements 
36/37/39-45-36/37
OEB
B
OEL
TWA: 2.3 ppm (10 mg/m3)
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
Hazardous Substances Data
106-44-5(Hazardous Substances Data)
Toxicity
LD50 orally in rats: 1.8 g/kg (Deichmann, Witherup)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
W233706
Product name
p-Cresol
Purity
≥99%, FG
Packaging
1kg
Price
$106
Updated
2024/03/01
Sigma-Aldrich
Product number
W233706
Product name
p-Cresol
Purity
≥99%, FG
Packaging
5kg
Price
$336
Updated
2024/03/01
Sigma-Aldrich
Product number
W233706
Product name
p-Cresol
Purity
≥99%, FG
Packaging
10Kg
Price
$557
Updated
2024/03/01
Sigma-Aldrich
Product number
W233706
Product name
p-Cresol
Purity
≥99%, FG
Packaging
25kg
Price
$1260
Updated
2024/03/01
Sigma-Aldrich
Product number
8.05223
Product name
p-Cresol
Purity
for synthesis
Packaging
100g
Price
$42.8
Updated
2024/03/01
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p-Cresol Chemical Properties,Usage,Production

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).

Chemical Properties

Cresol is a mixture of three isomeric forms: o-, m-, and p-cresol. These compounds are slightly soluble in water. The m-isomer is a colorless or yellow liquid with characteristic odor. The p-cresol is a colorless to pink crystals with a characteristics phenol-like odor. The concentration at which the odor becomes detectable in water is 55 parts per billion (Buttery et al., 1988). Another study by Leonardos et al. (1969) reported an experimental odor threshold concentration of 1 parts per billion, which is higher than the 0.054 parts per billion 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).

Uses

p-Cresol is utilized in the production of artificial resins, liquid crystal intermediates, disinfectants, fumigants, and as an industrial solvent. It is also involved in the manufacturing of Bupranolol, a non-selective beta blocker.

Definition

ChEBI: P-cresol is 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. It has a role as a uremic toxin, a human metabolite and an Escherichia coli metabolite.

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

General Description

Colorless solid with a tar like odor. Sinks and mixes slowly with water.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

p-Cresol is sensitive to heat. p-Cresol is also sensitive to light. p-Cresol is incompatible with strong oxidizers and strong alkalis. p-Cresol will attack some forms of plastics, coatings and rubber.

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.

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.

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.

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).

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).

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.

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.]

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.

p-Cresol Preparation Products And Raw materials

Raw materials

Sodium p-toluenesulfonate m-cresol and p-cresol mixture p-Toluenesulfonic acid Naphthol AS-OL PHENOLPHTHALIN o-Cresol Cresol Sodium nitrite 2-METHYLANILINE SULFATE m-Cresol

Preparation Products

p-Tolyl phenylacetate 4-Methylanisole Tolterodine 2,2-Dimethyl-3-(2-methylpropyl)cyclopropanecarboxylic acid p-(methoxymethyl)benzyl ester P-TOLYL ACETATE 2-Bromo-4-methylphenol 3,5-DIMETHYL-BENZOFURAN-2-CARBOXYLIC ACID 2-[3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-methylphenol 2-[[4-[[4-[bis(2-hydroxyethyl)amino]-6-chloro-1,3,5-triazin-2-yl]amino]phenyl]azo]-p-cresol Mn(Ⅲ)salen epoxidation catalyst ETHYL 4-ETHOXYPHENYLACETATE 2-tert-Butyl-4-methylphenol 4-CHLOROMETHYL-6-METHYL-CHROMEN-2-ONE 4-Hydroxybenzaldehyde Ethyl 3,5-dimethylbenzofuran-2-carboxylate ,95% P-TOLYL ISOBUTYRATE 1-(2-Hydroxy-5-methylphenyl)ethanone p-Anisaldehyde m-Cresol Acid Orange 116 Butylated Hydroxytoluene 2-HYDROXY-5-METHYLISOPHTHALALDEHYDE Neutral Brown Rl
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View Lastest Price from p-Cresol manufacturers

Qingdao RENAS Polymer Material Co., Ltd.
Product
p-Cresol 106-44-5
Price
US $0.00/kg
Min. Order
20kg
Purity
99%
Supply Ability
20 tons
Release date
2024-09-29
Hebei Weibang Biotechnology Co., Ltd
Product
p-Cresol 106-44-5
Price
US $100.00/kg
Min. Order
1kg
Purity
99%min
Supply Ability
200TON
Release date
2024-10-24
Hebei Chuanghai Biotechnology Co,.LTD
Product
4-methyl phenol 106-44-5
Price
US $10.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
10 ton
Release date
2024-08-20

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  • P-CRESOL GR 99+%
  • P-CRESYLIC ACID
  • P-CRESOL
  • P-HYDROXYTOLUENE
  • P-METHYLPHENOL
  • FEMA 2337
  • 4-HYDROXYTOLUENE
  • 4-METHYLPHENOL
  • AKOS BBS-00004354
  • p-Cresol 98+ %
  • 4-Methylhydroxybenzene
  • 4-Hydroxytoluol
  • P-CRESOL OEKANAL, 250 MG
  • P-CRESOL, STANDARD FOR GC
  • 4-METHYLPHENOL, 1000MG, NEAT
  • P-CRESOL GC STANDARD
  • P-CresolForSynthesis
  • 4-Cresol99%
  • P-CresolPurple
  • 4-Methylphenol,1PoC7H8O
  • 1-HYDROXY-4-METHYLBENZENE
  • p-cresol,4-methylphenol
  • 4-methylphenol solution
  • P-CRESOL,HIGHPURITY
  • PARA-OXYTOLUENE
  • PARA-HYDROXYTOLUENE
  • PARA-TOLYLALCOHOL
  • p-Cresol, extra pure, 99+%