phenolphthalein
Phenolphthalein
CAS: 77-09-8
Molecular Formula: C20H14O4
phenolphthalein - Names and Identifiers
| Name | Phenolphthalein |
| Synonyms | Phenolphthalien Phenolphthalein Phenolphthalein solution 2,2-bis(p-hydroxyphenyl)phthalide 3,3-bis(p-hydroxyphenyl)phthalide alpha-di(p-hydroxyphenyl)phthalide alpha-di-(p-hydroxyphenyl)phthalide 2-[bis(4-hydroxyphenyl)methyl]benzoic acid .alpha, alpha.-Di(p-hydroxyphenyl)phthalide ,3-bis(4-hydroxyphenyl)-1(3H)-isobenzofuranore 3,3-bis(4-hydroxyphenyl)-1(3h)-isobenzofuranon 3,3-bis(4-hydroxyphenyl)-2-benzofuran-1(3H)-one 1(3H)-Isobenzofuranone,3,3-bis(4-hydroxyphenyl)- 1(3H)-Isobenzofuranone, 3,3-bis(4-hydroxyphenyl)- alpha-(p-hydroxyphenyl)-alpha-(4-oxo-2,5-cyclohexadien-1-ylidine)-o-toluicacid |
| CAS | 77-09-8 |
| EINECS | 201-004-7 |
| InChI | InChI=1/C20H16O4/c21-15-9-5-13(6-10-15)19(14-7-11-16(22)12-8-14)17-3-1-2-4-18(17)20(23)24/h1-12,19,21-22H,(H,23,24) |
phenolphthalein - Physico-chemical Properties
| Molecular Formula | C20H14O4 |
| Molar Mass | 318.32 |
| Density | 1.27 g/cm3 at 32 °C |
| Melting Point | 261-263 °C (lit.) |
| Boling Point | 417.49°C (rough estimate) |
| Flash Point | 24°C |
| Water Solubility | <0.1 g/100 mL |
| Solubility | acetone: soluble. Soluble in ethanol and alkali solution, slightly soluble in ether, 1g soluble in 12ml ethanol, about 100ml ether, soluble in dilute alkali solution is dark red, very slightly soluble in chloroform, insoluble in water. |
| Vapor Presure | 7.12E-13mmHg at 25°C |
| Appearance | White powder |
| Color | White to yellow-white |
| Odor | Odorless |
| Maximum wavelength(λmax) | ['552nm, 553nm, 374nm, 205nm, 229nm, 276nm'] |
| Merck | 14,7243 |
| BRN | 284423 |
| pKa | 9.4(at 25℃) |
| PH | 7.8～10.0 |
| Storage Condition | no restrictions. |
| Stability | Stable. Incompatible with strong oxidizing agents, alkalies. |
| Sensitive | Easily absorbing moisture |
| Refractive Index | 1.5400 (estimate) |
| MDL | MFCD00005913 |
| Physical and Chemical Properties | Density 1.299 melting point 258-263°C water solubility <0.1g/100 mL |
| Use | Used as an acid-base indicator stimulant laxative for the treatment of constipation |
phenolphthalein - Risk and Safety
| Risk Codes | R40 - Limited evidence of a carcinogenic effect R22 - Harmful if swallowed R10 - Flammable R36/38 - Irritating to eyes and skin. R23/25 - Toxic by inhalation and if swallowed. R11 - Highly Flammable R36/37/38 - Irritating to eyes, respiratory system and skin. R68 - Possible risk of irreversible effects R62 - Possible risk of impaired fertility R45 - May cause cancer R39/23/24/25 - R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. |
| Safety Description | S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37 - Wear suitable protective clothing and gloves. S33 - Take precautionary measures against static discharges. S24 - Avoid contact with skin. S16 - Keep away from sources of ignition. S7 - Keep container tightly closed. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S53 - Avoid exposure - obtain special instructions before use. |
| UN IDs | UN 1993 |
| WGK Germany | 3 |
| RTECS | SM8380000 |
| TSCA | Yes |
| HS Code | 29322910 |
phenolphthalein - Reference
| Reference Show more | 1. Zhong Hongxing, Zhang Jing, Lu Jianhua et al. Comparison of three methods for determination of acid value of oil [J]. Journal of Food Safety and quality testing 2019(10):3197-3201. 2. Lu, Y., zhang, M., zhang, H. et al. On-chip acoustic mixer integration of electro-microfluidics destinations in-situ and efficient mixing in droplets. Microfluid Nanofluid 22,146 (2018). https://doi.org/10.1007/s10404-018-2169-7 3. [IF = 2.529] Lu Yao et al."On-chip acoustic mixer integration of electro-microfluidics towards in-situ and efficient mixing in droplets."Microfluid Nanofluid. 2018 Dec;22(12):1-12 4. [IF=5.537] Sen Yang et al."NAC transcription factors SNAC4 and SNAC9 synergistically regulate tomato fruit ripening by affecting expression of genes involved in ethylene and abscisic acid metabolism and signal transduction."Postharvest Biol Tec. 2021 Aug;178:111555 |
phenolphthalein - Introduction
Stable in the air. Soluble in ethanol and alkali solution, slightly soluble in ether, 1g soluble in 12ml ethanol, about 100ml ether, soluble in dilute alkali solution is dark red, very slightly soluble in chloroform, insoluble in water. The maximum absorption wavelength (in methanol) is 205, 229, 276nm(ε27261 · 147, 14692 · 144, 2006 · 369). The minimum lethal dose (rat, abdominal cavity) is 500mg/kg. It's irritating.
Last Update：2022-10-16 17:28:35
phenolphthalein - Reference Information
| Color index | 764 |
| pH range of acid-base indicator discoloration | 8.0(colorless)-10(Red) |
| Main application | 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, textures, corlot testing, exploratory, concrete, method for prevention of drugmisuse, cosmetics, diapers, detecting viable cells, carbohydrates, antimalarial, treating amyloid-associated diseases |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| (IARC) carcinogen classification | 2B (Vol. 76) 2000 |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | phenolphthalein is a weak organic acid, white or yellow tiny crystals at room temperature, odorless, tasteless, insoluble in water and soluble in alcohol (ethanol), ether. Dissolved in alcohol solution to make acid-base indicator, colorless in acidic solution, red in alkali or alkali metal carbonate solution, but if in concentrated alkali solution, it will produce colorless three metal salts, the red color fades. In view of this characteristic, it is often used as an indicator of acid-base titration in the laboratory. The pH value of the color change range is 8.2~10.0, and the color change from colorless to red. When the phenolphthalein reagent is dropped into water or a neutral, acidic aqueous solution, a white turbid substance will appear, which is due to the fact that alcohol is easily soluble in water, so that phenolphthalein which is hardly soluble in water in the reagent is precipitated. |
| molecular structure of phenolphthalein | phenolphthalein is also called phenolphthalein, chemical name 2-[bis-(4-hydroxyphenyl) methyl] benzoic acid. Molecular formula C20H16O4, relative molecular mass 318.33. The structural formula is shown in Figure 1 below (in fact often in the form of a colorless lactone, see figure 2). Triclinic white to yellowish crystalline powder, melting point 237~259 deg C, the relative density of 1.277(20/4 deg C). Soluble in ethanol, ether and other organic solvents, slightly soluble in water. It is weakly acidic and exists almost entirely in the molecular state even in very dilute solutions. Soluble in alkali solution, red in alkaline solution, colorless in acidic solution. Phenolphthalein molecules in the three benzene ring and a sp3 hybrid center carbon atom, no conjugated relationship between benzene ring, is colorless. In the case of alkali, The lactone ring opens and generates disodium salt, and the central carbon atom is converted into sp2 hybrid state, which contains benzoquinone structure. At this time, a conjugated system is formed with three benzene rings, thus showing red color; however, in the case of excess alkali, it is converted to the sp3 hybrid state, the conjugated system disappears, and the color also disappears. preparation method: phthalic anhydride can be produced by condensation with phenol in the presence of concentrated sulfuric acid or anhydrous zinc chloride. |
| phenolphthalein color change principle | phenolphthalein indicator commonly used in analytical chemistry, the colorless lactone ring-opening results in a quinone-like structure with a red color. Phenolphthalein, in turn, can be converted to colorless carboxylates when exposed to strong bases. Its color range is pH7.0 (colorless) to 10.0 (red). The test solution was prepared by dissolving 1g per liter of 90% ethanol. Phenolphthalein is colorless in solution with pH lower than 8.5, red when higher than 9, if the alkali is added in excess and does not color, the color change process is as follows: phenolphthalein is used as acid-base titration indicator, generally, a 1% concentration of the indicator solution is used. Dissolve 1g of Phenolphthalein in 100 of 80% alcohol and slowly drop 0.1 mol/L sodium hydroxide to a reddish color (to neutralize small amounts of acid that may be present in alcohol). The pH value of the color change range is 8.2 to 10. PH <8.2 for colorless,>10 red. The principle of color change is that the structure of the molecule itself changes under different acid and alkali conditions, resulting in different colors. Phenolphthalein mixed with other indicators can be formulated into a wide range of indicators commonly used today (also known as universal indicators). Mix 1.3g of phenolphthalein, 0.9g of bromothymol blue, 0.4g of Methyl red and 0.2g of Thymol Blue and dissolve them in 1 L of 70% ~ 80% alcohol, after complete dissolution, add 0.1 mol/L sodium hydroxide to make it just green and ready for use. The advantage is that there is a significant change in color with the change of pH: pH = 4 is red, 5 is orange, 6 is yellow, 7 is green, 8 is cyan, 9 is blue, 10 is purple. A wide variety of indicators can be formulated as needed. |
| phenolphthalein test paper | phenolphthalein test paper is one of the simple test papers commonly used in chemical analysis. It has strong pertinence, red in case of alkali, colorless in acidic and neutral solution. Test whether there is ammonia in the air, will also be light red. The preparation method is simple, and the filter paper is immersed in the phenolphthalein solution, and the absorption is saturated and then taken out and dried. |
| Application | phenolphthalein indicator is not only used in laboratories, but also widely used in industrial and agricultural production. In addition to the control of the pH of the reaction in the production of chemical products and the acid-base titration analysis of various products, it is used in the printing and dyeing industry to determine the pH of the fabric. This is very important for the printing and dyeing process, for example, if the residual alkali on the mercerized cloth is not washed, the dyeing will have no gloss. If the phenolphthalein indicator alone can only be used to determine whether the fabric is acidic or alkaline and its pH discoloration range, its specific pH value cannot be further determined. The acid-base strength on the cloth is clearly reflected by the broad indicator formulated as described above. Phenolphthalein in medicine can also be used as laxative, because it can stimulate the intestinal wall caused by peristalsis to promote defecation, but occasionally dermatitis and other allergic reactions, the use of attention. |
| uses | The main uses of phenolphthalein: 1, pharmaceutical industry pharmaceutical raw materials: suitable for habitual stubborn constipation, tablets, suppository and other dosage forms. 2, for Organic Synthesis: mainly used for the synthesis of plastics, especially the synthesis of phthalazinone Poly aryl ether ketone polyaryl ether ketone polymer, the polymer has excellent heat resistance, water resistance, chemical corrosion resistance, heat Aging resistance and good processing molding, made from its fibers, coatings and composite materials are soon widely used in electronic and electrical, mechanical equipment, transportation, aerospace, atomic energy engineering and military and other fields. 3, for acid-base indicator, non-aqueous titration indicator, color layer analysis reagent. This product is a commonly used acid indicator agent, and the color change range is pH8.2 (colorless)-10.0 (red). Phenolphthalein is also a drug that acts on the colon as a laxative and is used to treat constipation. used as acid-base indicator stimulant laxative for the treatment of constipation acid-base indicator, non-aqueous titration indicator, chromatographic analysis reagent. |
| pharmacology and toxicology | phenolphthalein can be used to treat habitual intractable constipation, mainly acting on the colon, after oral administration, it is slowly decomposed under the action of small intestinal alkaline intestinal fluid to form soluble sodium salt, thereby stimulating the nerve plexus in the intestinal wall, directly acting on the intestinal smooth muscle and increasing intestinal peristalsis, at the same time, it can inhibit the absorption of water in the intestine, so that water and electrolytes accumulate in the colon, resulting in laxative effect. Its role in relaxation, rarely cause intestinal spasm. |
| pharmacokinetics | about 15% is absorbed after oral administration, absorbed drugs are mainly excreted in urine or with feces in the form of glucuronides, and some are also excreted into the intestinal lumen through bile, which is reabsorbed in the intestine to form the intestinal-hepatic circulation, prolonged duration of action. 4-8 hours after drug administration, the soft stool was discharged, and 3-4 days after drug administration. This product is also secreted from the milk. |
| adverse reactions | phenolphthalein mainly acts on the large intestine, producing semi-liquid feces within 4-8 hours with little or no colic. It has not been demonstrated that yellow phenolphthalein is three times stronger than white. The effect of a single dose can last from 3 to 4 days as a result of enterohepatic circulation. This drug is an active member of many laxative preparations that are sold legally without a physician's prescription. serious adverse effects are rare but can occur in overdose. Phenolphthalein should not be used in the elderly, because its long-lasting effect can be serious depletion of water and electrolytes. Dermatitis (fixed rash, itching, burning sensation, blistering, and residual pigmentation) can occur in allergic patients. Fatal allergic reactions have been reported, but an absolute pathogenic relationship with phenolphthalein has not been established. Occasionally, non-thrombocytopenic purpura has been reported, and even dehydration and electrolyte disturbances due to excessive laxative effects may occur after prolonged use. Phenolphthalein makes alkaline urine or stool pink. |
| production method | is obtained by condensation of phthalic anhydride and phenol. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 15:16:52
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