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Phenol

Hydron phenoxide

HCID 20488062
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Grundinformationen

CAS
108-95-2
Standard-SMILES
[H+].[O-]c1ccccc1
InChIKey
ISWSIDIOOBJBQZ-UHFFFAOYSA-N
Summenformel
C6H6O
Durchschnittliche Molmasse
94,11 g/mol
Monoisotopische Masse
94,04186481

Überblick

Phenol is an antiseptic and disinfectant. It is active against a wide range of micro-organisms including some fungi and viruses, but is only slowly effective against spores. Phenol has been used to disinfect skin and to relieve itching. Phenol is also used as an oral analgesic or anesthetic in products such as Chloraseptic to treat pharyngitis. Additionally, phenol and its related compounds are used in surgical ingrown toenail treatment, a process termed phenolization. Research indicates that parental exposure to phenol and its related compounds are positively associated with spontaneous abortion. During the second world war, phenol injections were used as a means of execution by the Nazis. Phenol is a toxic compound whose vapours are corrosive to the skin, eyes, and respiratory tract.

Namen und Bezeichner

Bevorzugter Name
Hydron phenoxide
IUPAC
hydron phenoxide
Lokaler Name
Phenol
Englischer Name
Phenol
Summenformel
C6H6O
Molmasse
94.11

Namen und Synonyme

SCHEMBL11137144PhOHFenolCARBOLIC ACIDHYDROXYBENZENEPHENOL CRYSTALSLIQUIFIED PHENOLBENZENOLPhenol, water saturated, stabilizedBenzophenolPhenyl alcohol

Datenbank-Bezeichner

CAS
108-95-2
PubChem CID
20488062

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
23,1 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
0
Schwere Atome
7
Formalladung
0
Komplexität
46,1

Experimentelle und physikochemische Eigenschaften

LogP1.46
Solubility82.8 mg/mL at 25 °C
Melting Point40.9 °C
Physical DescriptionSolid
Dissociation Constants9.99 (at 25 °C)

Physikochemische Eigenschaften

Schmelzpunkt
40.5 °C · 40.5 °C (104.9 °F; 313.6 K)
Siedepunkt
181.7 °C · 181.7 °C (359.1 °F; 454.8 K)
Dichte
1.07 g/cm3 · 1.07 g/cm3
Dampfdichte
3.24 · 3.24 (vs air)
Dampfdruck
0.09 psi · 0.09 psi ( 55 °C)
FEMA
3223 · 3223 | PHENOL
Brechungsindex
1.4222 · n /D 1.4222
Flammpunkt
79 °C · 79 °C (174 °F; 352 K)
storage temp.

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Sicherheitsdaten

F
8-23
OEB
A
OEL
TWA: 5 ppm (19 mg/m3), Ceiling: 15.6 ppm (60 mg/m3) [15-minute] [skin]
wgk
2
IDLA
250 ppm
tsca
TSCA listed
ridadr
UN 2821 6.1/PG II/III (PHENOL SOLUTION)
hs_code
29071100
RTECS-Nr.
SJ3325000
risk_code
23/24/25-34-48/20/21/22-68-40-39/23/24/25-11-36-20/21/22-24/25
Toxizität
LD50 orally in rats: 530 mg/kg (Deichmann, Witherup)
hazard_code
T,C,F,Xn
safety_code
26-36/37/39-45-36/37-28A-28-24/25-1/2-36-16-7
hazard_class
6.1
packing_group
II
Speicherklasse
3 - Flammable liquids
Giftige Stoffe Daten
108-95-2(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
Selbstentzündungstemperatur
715 °C

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

Phenol is a potent proteolytic agent. Concentrations in the 5% to 7% range dissolve tissue on contact via proteolysis. In high concentrations when injected next to a nerve, phenol produces a chemical neurolysis which is nonselective across nerve fiber size and most prominent on its outer aspect. Local anesthetic effects occur within 5-10 minutes.

Metabolism/MetabolitesPhenyl sulfate, phenyl glucuronide, quinol sulfate, and quinol glucuronide were detected in human beings as phenol metabolites.
Absorption, Distribution and Excretion · 4 Einträge

Phenol is rapidly absorbed through the skin and into the lungs.

The kidney is the primary route of elimination of phenol.

At I5 min after exposure, the liver contained the highest level of phenol, consisting mainly of free phenol. After 82 minutes post administration, phenol is uniformly distributed in the liver, blood, kidneys, lungs, along with the heart, testes, thymus and the spleen. With the passage of time, the proportion of free to conjugated phenol changed. By 360 minutes most phenol appears in conjugated forms.

In rabbits, 72% is excreted in the urine, 1% in the feces, 4% in the carcass following sacrifice, and trace amounts were exhaled.

Tissue LocationsAdipose Tissue
Metabolite PathwaysSulfite oxidase deficiency
Anwendungen · 4 Einträge

BeschreibungPhenol is a stable chemical substance and appear as colourless/white crystals with a characteristic, distinct aromatic/acrid odour. It is reactive and incompatible with strong oxidising agents, strong bases, strong acids, alkalis, and calcium hypochlorite. Phenol is flammable and may discolour in light. Phenol is used in the manufacture or production of explosives, fertiliser, coke, illuminating gas, lampblack, paints, paint removers, rubber, perfumes, asbestos goods, wood preservatives, synthetic resins, textiles, drugs, and pharmaceutical preparations. It is also extensively used as a disinfectant in the petroleum, leather, paper, soap, toy, tanning, dye, and agricultural industries.

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
2 · 2-8°C
Löslichkeit
2 O: · H2O: 50 mg/mL at 20 °C, clear, colorless
pka
9.89 · 9.89(at 20℃)
Aggregatzustand
Transparent crystalline solid
Wichte
1.071 · 1.071
Farbe
faintly yellow
Geruch (Odor)
0.06 ppm · Sweet, medicinal odor detectable at 0.06 ppm
PH
6.47 · 6.47(1 mM solution);5.99(10 mM solution);5.49(100 mM solution);
Explosionsgrenze
1.3 · 1.3-9.5%(V)
Odor Threshold
0.0056 ppm · 0.0056ppm
Geruchsart
phenolic
Biologische Quelle
synthetic
Wasserlöslichkeit
8 g/100 · 8 g/100 mL
Spezifische Wärmekapazität
1.35 J/ · Cp(crystal): 1.35 J/(g·K), at 25℃
Merck
14 · 14,7241
JECFA Number
690 · 690
BRN
969616 · 969616
Henry's Law Constant
1.09 at · 1.09 at 5 °C (average derived from six field experiments, Lüttke and Levsen, 1997)
Dielectric constant
4.3 · 4.3(10℃)
Stabilität
Hygroscopic
Major Application
agriculturecleaning productscosmeticsenvironmentalfood and beveragespersonal care
Kosmetik-Inhaltsstoffe Funktionen
PRESERVATIVEORAL CAREFRAGRANCEDENATURANTANTIMICROBIALDEODORANT
InChI
1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
InChIKey
ISWSIDIOOBJBQZ-UHFFFAOYSA-N
SMILES
Oc1ccccc1
LogP
1.47 at · 1.47 at 30℃
CAS Datenbank
108 · 108-95-2(CAS DataBase Reference)
NIST chemische Informationen
Phenol(108-95-2)
EPA chemische Informationen
Phenol (108-95-2)
Absorption
294 nm · cut-off at 294nm in H2O at 0.5M

OccurrenceIt is reported found in over 150 natural products including apricot, sour cherry, black currant, bilberry, cranberry, other berries, grapes, guava fruit, peach, pineapple, asparagus, onion, cooked potato, tomato, cinnamon bark, cassia leaf, ginger, pennyroyal oil, many cheeses, butter, milk, milk powder, boiled egg, fish and fish oil, cooked and cured meats, beer, wheaten bread, crisp bread, cognac, rose wine, cocoa, coffee, tea, whiskies, roasted filbert, roasted peanut, soybean, pecans, honey, avocado, Arctic bramble, passion fruit, beans, mushrooms, burley tobacco, cooked beef and chicken, fermented soy sauce, trassi, roasted almonds, sesame seed, fenugreek, mango, tamarind, Brazil nut, rice, rhubarb, licorice, buckwheat, watercress, malt, wort, dried bonito, loquat, myrtle berry, rosemary, Tahiti and Bourbon vanilla, endive, shrimp, crab, crayfish, clam, squid, truffle and Chinese quince.

HistoryPhenol’s first prominent use was by Joseph Lister (1827–1912) as an antiseptic. Throughout human history,infection often resulted in death,even when the wound could be surgically treated.A broken bone piercing the skin, which today is a painful but not life-threatening injury,historically resulted in infection and possible amputation or death. Lister was inspired by Louis Pasteur’s (1822–1895) germ theory of disease,and he began to use antiseptic methods during routine surgery during the 1860s.

Verwendenphenol is frequently used for medical chemical face peels. It may trap free radicals and can act as a preservative. Phenol, however, is an extremely caustic chemical with a toxicity potential. It is considered undesirable for use in cosmetics. even at low concentrations, it frequently causes skin irritation, swelling, and rashes.

Darstellung

synthetischePhenol is formed in dry distillation of wood, peat and coal; coal tar is one of the commercial sources of phenol and its homologues.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

4-IsopropylanilinErdoelgase, verflüssigt3-(4-Isopropylphenyl)-1,1-dime-thylharnstoff(1-Methylethyl)benzolExtrakte, alkalische Kohlenteeroel-PropyleneNatriumsulfatNatriumsulfitSchwefeldioxidNatriumbenzolsulfonatSchwefeltrioxidDestillate (Kohlenteer)BenzolCumolhydroperoxidNatriumhydroxidGlas, Oxid, ChemikalienLigroinSchwefelsure

Nachgelagerte Produkte

MCPA (ISO)3-Chloro-4-phenoxyanilineSODIUM PHENOLATE TRIHYDRATE4,4'-(4,5,6,7-Tetrabrom-3H-2,1-benzoxathiol-3-yliden)bis[2,6-dibromphenol]-S,S-dioxidBisacodyl3-Phenoxypropionsure2,4,6-Tri-tert-butylphenolDispersing agent S4,4'-Isopropylidendiphenyldimethacrylat4-Nitrophenylphenylether2,4,6-TrichlorphenolDiphenylphthalat4-Phenoxybutanoic acidChroman-4-on2-PhenoxypropionsureTris(isopropylphenyl)phosphatOctadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionat2,4-Di-tert-butylphenolTris(2,4-ditert-butylphenyl)phosphit3-Phenoxyanilin4'-PhenoxyacetophenoneNatriumpentachlorphenolatHigh temperature levelling agent BOFp-Coumaric acid6-PhenoxynicotinonitrileRoxatidine acetateFenpropathrinALKYLPHENOL DISULFIDESulphur Indanthrene Blue RNX3-Amino-1-phenoxy-2-propanol hydrochlorideAcid Red 111p-HydroxyvalerophenonAntioxidant T502synthetic tanning agent No.28Seratrodast4-Hydroxymandelic acid monohydrateDisperse purple H-FRLXanthen2,4-Dichlorphenyl-4-nitrophenyletherAdhesive 706

Ergänzende Hinweise

DefinitionChEBI: An organic hydroxy compound that consists of benzene bearing a single hydroxy substituent. The parent of the class of phenols.