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Phenolphthalein
PHENOLPHTALEIN · Fenolftalein · phenolphtaleine · colax · PHENOLPHTHALEIN INDICATOR SOLUTION · 3,3-bis(4-hydroxyphenyl)isobenzofuran-1(3H)-one · alophen · phthalin
Identifikatoren & physikalische Daten
| CAS No. | 5768-87-6 |
|---|---|
| Summenformel | C20H14O4 |
| Durchschnittliche Molmasse | 318,3 g/mol |
| Monoisotopische Masse | 318,08920893 g/mol |
| SMILES | O=C1OC(c2ccc(O)cc2)(c2ccc(O)cc2)c2ccccc21 |
| InChIKey | KJFMBFZCATUALV-UHFFFAOYSA-N |
| PubChem CID | 4764 |
| ChEMBL | CHEMBL63857 |
| ChEBI | CHEBI:34914 |
| EC No. | 201-004-7 |
| DTXSID | DTXSID0021125 |
| Lokaler Name | Phenolphthalein |
Chemische & physikalische Eigenschaften
| XLogP | 3,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 66,8 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 24 |
| Formalladung | 0 |
| Komplexität | 438 |
| Stoffklassen | Dyes -> Indicator DyesCarcinogens |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Used in Switzerland |
| SpringerMaterials Properties | Fusion temperature |
| LogP (Verteilungskoeffizient) | log Kow = 2.413.36 |
| Geruch | ODORLESS |
| Dichte | 1.299 at 77 °F (NTP, 1992) - Denser than waterwill sink1.277 @ 32 °C1.299 @25 °C1.27 g/cm3 at 32 °C |
| Color/Form | White or yellowish-white minute, triclinic crystals, often twinnedWhite rhombic needlesPale yellow powder |
| Löslichkeit | less than 1 mg/mL at 66 °F (NTP, 1992)1 g dissolves in 12 ml alcohol, in about 100 ml ethersol in dil solutions of Alkali hydroxides and hot solutions of alkali carborates forming a red solnInsoluble in benzene and petroleum etherslightly soluble in carbon disulfidesoluble in ethyl ether, chloroform, and toluenevery soluble in ethanol, acetone, and pyrene.In water, 400 mg/L @ room temperatureSoluble in alcohol. Slightly soluble in ether. Slightly soluble in dimethyl sulfoxide and insoluble in benzene or hexane.<0.1 g/100 mL |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| Schmelzpunkt | 496 to 504 °F (NTP, 1992)262.5 °C261-263 °C (lit.) |
| Dampfdruck | 6.7X10-13 mm Hg @ 25 °C /Estimated/<0.00001 Pa ( 50 °C) |
| Siedepunkt | 417.49°C (rough estimate) |
| Brechungsindex | 1.5400 (estimate) |
| Flammpunkt | 24 °C |
| Lagerbedingungen | no restrictions. |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 9.4(at 25℃) |
| Farbe | White to yellow-white |
| Geruch | Odorless |
| pH | 7.8~10.0 |
| Merck | 14,7243 |
| BRN | 284423 |
| Henry-Konstante | 1.1×1010 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Incompatible with strong oxidizing agents, alkalies. |
| Hauptanwendungen | Display device, sensors, semiconductors, fuel cells, photoreceptors, electronic packaging, authentication system for secure documents, inks, correction fluid, paints, detection of defects in films, floor coatings, textiles, corrosion testing, explosive, concrete, toys, detecting lipase activity of crop seeds, soaps, method for prevention of drugmisuse, cosmetics, diapers, detecting viable cells, carbohydrates, antimalarial, treating amyloid-associated diseases |
| InChI | 1S/C20H14O4/c21-15-9-5-13(6-10-15)20(14-7-11-16(22)12-8-14)18-4-2-1-3-17(18)19(23)24-20/h1-12,21-22H |
| InChIKey | KJFMBFZCATUALV-UHFFFAOYSA-N |
| SMILES | Oc1ccc(cc1)C2(OC(=O)c3ccccc23)c4ccc(O)cc4 |
| LogP (Verteilungskoeffizient) | 2.410 |
| CAS Datenbank | 77-09-8(CAS DataBase Reference) |
| NIST chemische Informationen | Phenolphthalein(77-09-8) |
| EPA chemische Informationen | 3,3-Bis(4-hydroxyphenyl)phthalide (77-09-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH341: Suspected of causing genetic defects [Warning Germ cell mutagenicity]P203, P280, P318, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.2% (2 of 1181) of reports.H341 (99.5%): Suspected of causing genetic defects [Warning Germ cell mutagenicity] |
|---|---|
| Regulatorische Informationen | Chemical: 1(3H)-Isobenzofuranone, 3,3-bis(4-hydroxyphenyl)-Hazard Traits - CarcinogenicityStatus: Active Update: 01-12-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/2203Substance: PhenolphthaleinPhenolphthalein: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| Weitere Sicherheitsinformationen | IMAP assessments - 1(3H)-Isobenzofuranone, 3,3-bis(4-hydroxyphenyl)-: Human health tier II assessment |
| DOT-Kennzeichnung | Combustible Liquid |
| Brandgefahren | Literature sources indicate that this compound is nonflammable. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: Exposure to this compound may cause purging, collapse and erythematous, itching skin rash that may progress to persistent ulceration. Acute exposure may cause hypotension, vomiting, watery or bloody diarrhea, pallor, rapid heart rate, coma and death. Other symptoms include burning pain in the mouth and stomach and tenesmus. Eye contact may result in edema of the eyelids and conjunctival ecchymoses. It may also result in irritation, redness and pain. It has occasionally caused albuminuria and hemoglobinurea. It may also cause skin rash. Other symptoms include pink coloring of the urine and feces, allergic reactions including fixed-drug eruption, Stevens-Johnson syndrome (resembles lupus erythematosus), osteomalacia, protein-losing gastroenteropathy, and fluid and electrolyte deficits. Exposure has also caused cerebral and pulmonary edema, oliguria and severe acidosis. Hypothermia has also been reported. Other symptoms include abdominal cramps, cardiac and respiratory distress, lack of sphincter control, flaccid paralysis, fixed mydriasis, intense cyanosis, undetectable blood pressure or pulse, toxic epidermal necrolysis, and bullous lesions on the hands, lips, mouth and tongue. |
| Gefahrenübersicht | Reported health effects include itching rash after skin contact and purging and collapse after ingestion[CAMEO] Dust may be irritating if inhaled, but probably not irritating to the skin[CHEMINFO] |
| FDA-Anforderungen | Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: Danthron phenolphthalein is included in laxative drug products. |
| Reaktive Gruppe | Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters |
| Special Reports | National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Phenolphthalein (77-09-8) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s145phen.pdf] |
| Reactivity Profile | PHENOLPHTHALEIN is incompatible with alkaloids. (NTP, 1992) |
| Air and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories | Muta. 2 (99.5%)Carcinogenicity - category 1BSerious eye damage/eye irritation - Category 2Germ cell mutagenicity - Category 2Carcinogens |
| Brandbekämpfung | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992) |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| Lagerbedingungen | PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/ |
| Reinigungsverfahren | PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/ |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| Entsorgungsverfahren | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/For more Disposal Methods (Complete) data for PHENOLPHTHALEIN (6 total), please visit the HSDB record page. |
| Preventive Measures | SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/For more Preventive Measures (Complete) data for PHENOLPHTHALEIN (10 total), please visit the HSDB record page. |
| Isolation and Evacuation | Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: |
| Protective Action Criteria (PAC) | 0.12 [mg/m3]1.4 [mg/m3]20 [mg/m3] |
| Personal Protective Equipment (PPE) | RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/ |
| Wechselwirkungen | Pretreatment of rats with sodium methotrexate (1 mg, orally, daily for 5 days) or vincristine sulfate (0.03 mg/kg, iv, weekly for 3 wk) markedly reduced biliary excretion of phenolphthalein (10 mg/kg, iv) indicating that hepatic function was decreased. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 490(SRC), determined from a log Kow of 490(2) and a regression-derived equation(3), indicates that phenolphthalein is expected to have moderate mobility in soil(SRC). Volatilization of phenolphthalein from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.0X10-16 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Phenolphthalein is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.7X10-13 mm Hg(5).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 490(SRC), determined from a log Kow of 2.41(2) and a regression-derived equation(3), indicates that phenolphthalein is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 9.0X10-16 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 14(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), phenolphthalein, which has an estimated vapor pressure of 6.7X10-13 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase phenolphthalein may be removed from the air by wet and dry deposition(SRC). |
| Unerwünschte Wirkungen | IARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer. |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=77-09-8] |
| Medical Surveillance | PRECAUTIONS FOR "CARCINOGENS": Whenever medical surveillance is indicated, in particular when exposure to a carcinogen has occurred, ad hoc decisions should be taken concerning ... /cytogenetic and/or other/ tests that might become useful or mandatory. /Chemical Carcinogens/ |
| Soil Adsorption/Mobility | The Koc of phenolphthalein is estimated as 490(SRC), using a log Kow of 2.41(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that phenolphthalein is expected to have moderate mobility in soil. |
| Natural Pollution Sources | Phenolphthalein is not known to occur as a natural product(1). |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ Only ocular complications reported have been edema of eyelids and conjunctival ecchymoses accompanying widespread reactions of skin, which may be severe./HUMAN EXPOSURE STUDIES/ ... Major danger /from/ overdosage ... is fluid and electrolyte deficits resulting from excessive laxative effect. However, allergic reactions, including fixed-drug eruption, stevens-johnson syndrome, and a syndrome that resembles lupus erythematosus, have been reported ... /diphenylmethane derivatives//HUMAN EXPOSURE STUDIES/ Phenolphthalein was used by 236 mother-child pairs during the first trimester and 806 anytime during pregnancy...No evidence was found to associate the use of this drug with major or minor malformations./HUMAN EXPOSURE STUDIES/ A retrospective study of 172 phenolphthalein ingestions, ranging from 32.5 to 1620 mg... in children indicated that about 20% had no symptoms. Most had minor symptoms that resolved within 24 hours.For more Human Toxicity Excerpts (Complete) data for PHENOLPHTHALEIN (12 total), please visit the HSDB record page. |
| Artificial Pollution Sources | Phenolphthalein's production and use an acid/base indicator, as a laboratory reagent, and its former use as a laxative(1), may result in its release to the environment through various waste streams(SRC). |
| Carcinogen Classification | PhenolphthaleinGroup 2B: Possibly carcinogenic to humansVolume 76: (2000) Some Antiviral and Antineoplastic Drugs, and Other Pharmaceutical Agents1999 |
| Environmental Bioconcentration | An estimated BCF of 14 was calculated for phenolphthalein(SRC), using a log Kow of 2.41(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for phenolphthalein is estimated as 9.0X10-16 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that phenolphthalein is expected to be essentially nonvolatile from water surfaces(2). Phenolphthalein's Henry's Law constant indicates that volatilization from moist soil surfaces may not occur(SRC). Phenolphthalein is not expected to volatilize from dry soil surfaces(SRC) based uponan estimated vapor pressure of 6.7X10-13 mm Hg(3). |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29322910 |
| RTECS-Nr. | SM8380000 |
| R-Sätze (R) | 40-22-10-36/38-23/25-11-36/37/38-68-62-45-39/23/24/25-23/24/25 |
| Gefahrensymbole | Xn,T,F,Xi |
| Sicherheitshinweise (S) | 45-36/37-33-24-16-7-36-26-53 |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrstoffdaten | 77-09-8(Hazardous Substances Data) |
| Gefahrenklasse | Carc. 1BMuta. 2Repr. 2Skin Irrit. 2 |
Anwendungen & Verwendung
Beschreibung
Phenolphthalein bildet weiße bis gelbliche trikline Kristalle mit einem Schmelzpunkt von 258-262 ℃. Es löst sich in Ethanol und Ether, aber nur wenig in Chloroform. Ein Gramm Phenolphthalein löst sich in 12 ml Ethanol oder in ungefähr 100 ml Ether. In Wasser ist es praktisch nicht löslich. In Alkali-Laugen und heißen Alkalicarbonat-Lösungen löst es sich mit fuchsinroter Farbe. Eine 1%-ige alkoholische Phenolphthalein-Lösung wird oft als Titrations-Indikator verwendet. Der Umschlagsbereich von farblos nach rot liegt dabei bei pH 8-9. Eine ausführliche Beschreibung der Reaktionen von Phenolphthalein bei verschiedenen pH-Werte ist im folgen Artikel zu finden: G. Wittke,
Verwenden
Phenolphthalein can be used as an inhibitor and pH indicator. It also induces centrosome amplification and tubulin depolymerization in vitro.