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2-Phenylphenol

Basic information Chemical properties uses Identification test Content analysis Toxicity Usage limit Production method Hazards & Safety Information Safety Related Supplier
2-Phenylphenol Basic information
2-Phenylphenol Chemical Properties
  • Melting point:57-59 °C(lit.)
  • Boiling point:282 °C(lit.)
  • Density 1.21
  • vapor pressure 7 mm Hg ( 140 °C)
  • refractive index 1.6188 (estimate)
  • FEMA 3959 | 2-PHENYLPHENOL
  • Flash point:255 °F
  • storage temp.  0-6°C
  • solubility Soluble in ethanol, acetone, benzene,sodium hydroxide, chloroform, acetonitrile, toluene, hexane, ligroin, ethyl ether, pyridine, ethylene glycol, isopropanol, glycol ethers and polyglycols.
  • pka10.01(at 25℃)
  • form Crystalline Flakes
  • color White
  • PH7 (0.1g/l, H2O, 20℃)
  • explosive limit1.4-9.5%(V)
  • Water Solubility 0.7 g/L (20 ºC)
  • Sensitive Hygroscopic
  • Merck 14,7304
  • JECFA Number735
  • BRN 606907
  • Stability:Stable. Combustible. Incompatible with strong oxidizing agents, halogens.
  • InChIKeyLLEMOWNGBBNAJR-UHFFFAOYSA-N
  • CAS DataBase Reference90-43-7(CAS DataBase Reference)
  • IARC3 (Vol. 73) 1999
  • NIST Chemistry Referenceo-Hydroxybiphenyl(90-43-7)
  • EPA Substance Registry System2-Phenylphenol (90-43-7)
Safety Information
  • Hazard Codes Xi,N
  • Risk Statements 36/37/38-50-37/38/50-36
  • Safety Statements 22-61
  • RIDADR UN 3077 9/PG 3
  • WGK Germany 2
  • RTECS DV5775000
  • Autoignition Temperature>520 °C
  • TSCA Yes
  • HazardClass 9
  • PackingGroup III
  • HS Code 29071900
  • Hazardous Substances Data90-43-7(Hazardous Substances Data)
  • ToxicityLD50 orally in rats: 2.48 g/kg (Hodge)
MSDS
2-Phenylphenol Usage And Synthesis
  • Chemical propertiesBright purple crystals
  • uses1. Fungicides: fruit and vegetable preservative. It is mainly used for the treatment of citrus epidermis mold.
    2. For the European Economic Community countries and the United States, in addition to be applied citrus, can still use it for cucumber, carrot, apple, melon, tomatoes and so on. Japan is limited to citrus with the maximum residue 0.01g/kg (1990).
    3. The usage condition of each country is as follows (allowable amount, mg/kg) Canadian cherry, 5; citrus, cucumber, pepper, pineapple, tomato, 10; sweet potato, 15; carrot, peach, plum fruit, 20; ; Melon, 12. European citrus, 12. Dutch citrus, 10. English citrus, 70; apple, pear, pineapple, 10; melon, 125. Orange, pepper, pineapple, tomato, sweet potatoes, 15; carrots, peaches, plums, pears, pears, pears, pears, pears, pomegranates, citrus, cucumber, grapefruit: 20; apple, pear, 25; Roman melon, 125 (edible part ≤10).
    4. Usage method: The goods is embedded into wax at about 0.8% with spray or dipping way for treatment, being able to prevent the corruption caused by the Gectricnumdidum. This product is of the best efficacy with biphenyl. For the treatment of mildew caused by P. digitation in citrus, 60.% of the untreated product was moldy in about 3 to 5 weeks while only 3.4% of the treated product became moldy finally.
    5. 2-Phenylphenol can be used as antiseptic fungicide. China provides that it can be used for citrus preservation with the maximum usage amount of 3.0g/kg and the residue amount being not greater than 12 mg/kg.
    6. As antiseptic fungicide, the provisions of China can also be used for citrus preservation, the maximum use of 3.0g/kg and residue being not greater than 12mg/kg.
    7. 2-Phenylphenol is used for strong bactericidal function, being used for the preservation of wood, leather and paper as well as storage of fruits and vegetables and meat preservation.
    8.  2-hydroxy biphenyl is used as the carrier of carrier dyeing method of hydrophobic synthetic fiber polyvinyl chloride and polyester, surfactants, bactericidal preservatives, dye intermediates. In Japan, 2-hydroxy biphenyl and sodium salt is used for the prevention of citrus mildew. We can embed into wax with 0.8% of the product and spray into the post-harvest citrus, or can also use it in combination with biphenyl, being able to minimize the corruption. Britain, the United States, and Canada allow the use of a larger range of fruits, including apples, pears, pineapple and so on. The goods, as a preservative is also used in cosmetics. The oral LD50 of 2-hydroxybiphenyl to rats was 2.7-3.0 g/kg.
    9. It can be used for preservation of fruits and vegetables.
    10. 2-Phenylphenol can be applied to fluorescence determination of triose. It can also be used as Dye intermediates.
    11. Used as a deoxyribonuclease (DNase) inhibitor;
  • Identification testTake 1 mL of 1% ethanol solution, plus 4 mL of 0.2% borax solution and a small amount of small crystals of 2,6-dichloro benzoquinone chloride imine, after shaking, the solution should be green to blue.
    Take 1 mL of 1% of the sample ethanol solution, plus 1 mL of formaldehyde sulfuric acid solution (TS-113), the interface should be red.
  • Content analysisAccurately weigh about 2 g of powder sample, add 25 mL of sodium hydroxide test solution (TS-224), if necessary, it can be warmly dissolved. Add water to 500ml after cooling and take it as a sample solution. Take 25 mL of this sample solution and transfer into the iodine bottle, accurately add 30 mL of 0.1mol/L potassium bromate solution plus 5 mL potassium bromide test solution (TS-181) 5 mL and 50 mL methanol for thoroughly shaking. Quickly add about 10 mL of 1: 1 dilute hydrochloric acid, immediately plug and gently shake for a reaction of 30s. Take 15 ml of potassium iodide solution (TS-192) and place into the upper part of the iodine bottle, and the stopper was let out to let it flow in. After thoroughly rinsing the stopper and bottle with water, the sample was shaken for 5 min. The free iodine was titrated with 0.1 mol/L sodium thiosulfate solution and the starch test solution (TS-235) was used as the indicator. The same method is applied for blank test to obtain content according to the following formula.
    Content (%) = 4.255 × (a-b) /sample amount (g) × 50 × 100%
    Where a-blank consumption of sodium thiosulfate volume, m1;
    B-Sample solution consumption of sodium thiosulfate volume, ml.
  • ToxicityADI: 0 to 0.2 mg/kg (0.2 to 1.0 mg/kg under certain conditions; FAO/WHO, 2001).
    LD50: 2.7 to 3.0 g/kg (rat, oral).
    The Tokyo health institute in Japan has found that experimental animals have a significant role in bladder cancer.
  • Usage limitGB 2760-2001: citrus fresh 1.0g/kg, residues ≤ 12mg/kg.
  • Production method(1) It can be recovered from the distillation residue of the process of phenol production via sulfonation. The phenol distillation residue contains about 40% of phenyl phenol with the other components including phenol, inorganic salts, water and so on. After vacuum distillation, the mixed phenyl phenol fraction is separated out with the vacuum being 53.3-66.7kPa. The temperature, started to be cut at 65-75 ℃ to until 100 ℃ above, but should not higher than 1345 ℃. Then take advantage of the solubility difference of ortho, p-hydroxy biphenyl in the trichlorethylene, the two are separated into pure product. The mixed material (mainly 2-hydroxy biphenyl and 4-hydroxy biphenyl) is heated to be dissolved in the trichlorethylene, after cooling, first precipitate out 4-hydroxy biphenyl crystal. After centrifuge filtration, dry to obtain 4-hydroxy biphenyl. The mother liquor was washed with a sodium carbonate solution, followed by dilute alkaline to make the 2-hydroxybiphenyl salt. After standing stratification, take the upper 2-hydroxybiphenyl sodium salt for dehydration under reduced pressure, namely, sodium salt products. The 2-hydroxybiphenylsodium salt is white to light red powder, being easily soluble in water with the solubility in 100g of water being 122g. The pH value of the 2% aqueous solution is 11.1-12.2. It is also easily soluble in acetone, methanol, soluble in glycerol, but insoluble in oil. The sodium salt of 2-hydroxy biphenyl, after acidification, can lead to the formation of 2-hydroxy biphenyl with both of them being food additives.
    (2) The mixture of 2-Phenylphenol (o-phenylphenol) and p-phenylphenol is obtained from the by-product of the phenol production by the sulfonation process. The mixture is heated and dissolved in trichlorethylene. After cooling crystallization, we can obtain para-phenylphenol with centrifuge filtering and solid drying to obtain Phenylphenol. The mother liquor was washed with sodium carbonate solution, neutralized with dilute sodium hydroxide and acidified to give o-phenylphenol.
    (3) The distillation residue of sulfonation method for production of phenol production contains about 40% of the mixed (para and ortho) phenyl phenol. Taking advantage of difference of the fractionation and solubility in the trichlorethylene, separate and recover ortho products.
    The above distillation residue is subject to vacuum distillation at 53.3~66.7 kPa, collecting the distillate fraction at 65~100 °C, namely mixed phenyl phenol. The mixture was heated to be dissolved in trichlorethylene with cooling first precipitating out the para-phenyl phenol. After centrifugal filtration, wash the mother liquor with sodium carbonate solution so that the o-phenyl phenol will become sodium salt. After standing, take the upper sodium salt, after acidification, we can obtain the product.
    (4) It can be obtained through the co-heating of dibenzofuran and sodium metal to about 200 °C with the resulting product subjecting to acid decomposition.
    (5) It can be obtained through the diazotization and further hydrolysis of 2-aminobiphenyl.
  • Hazards & Safety InformationCategory Pesticides
    Toxic classification poisoning
    Acute toxicity Oral-rat LD50: 2000 mg/kg; oral-mouse LD50: 1050 mg/kg
    Stimulation Data Skin-Rabbit 20 mg/24hours Moderate; Eyes-Rabbit 0.05 mg/24 h Severe
    EXPLOSIVES HAZARDOUS CHARACTERISTICS being explosive when being mixed with air
    Flammability and Hazardous properties being flammable with combustion producing irritating fumes
    Storage and transportation characteristics Ventilated, low temperature and drying
    Fire extinguishing agent dry powder, foam, sand
  • DescriptionOPP is more selective than other free phenols but does produce phytotoxic effects. Sodium o-phenylphenate (SOPP) is used in practice because it is much less phytotoxic to fruits and has a greater water solubility. Tomkins (42) tried to diminish the phytotoxic effect by esterification of the phenolic group. Acetate and butyrate esters gave efficient control of Botrytis on grapes and Monilia on peaches, but esters of o-phenylphenol are easily hydrolyzed into the free phenol (43). The methyl ether was less active against Diplodia and virtually inactive against Penicillia.
  • Chemical PropertiesOff-white powder
  • Chemical Propertieso-Phenylphenol is a white to buff-colored crystalline solid.
  • Chemical Properties2-Phenylphenol has a distinct odor. It emits acrid smoke and irritating fumes when it is heated to decomposition.
  • Uses2-Phenylphenol is used for the post-harvest control of storage diseases of apples, citrus fruit, stone fruit, tomatoes, cucumbers and other vegetables. It is also used for the protection of textiles and timber and as a fungistat in water-soluble paints. It is used as the sodium salt in paint and some other applications.
  • Uses2-Phenylphenol is a agriculture fungicide and is no longer used as a food additive.
  • Uses2-phenylphenol is remarkably versatile organic chemical products, widely used antiseptic, auxiliaries and surfactant synthesis of new plastics, resins and polymer materials in areas such as stabilizers and flame retardants.
  • DefinitionChEBI: A member of the class of hydroxybiphenyls that is biphenyl substituted by a hydroxy group at position 2. It is generally used as a post-harvest fungicide for citrus fruits.
  • PreparationFrom chlorobenzene.
  • Production MethodsOPP is produced as a by-product in the manufacture of diphenyl oxide or by aldol condensation of hexazinone. Current global production is estimated to be less than 10 million lb per year. Chief uses of products containing OPP are as disinfectants, antimicrobials, preservatives, antioxidants, and sanitizing solutions in various industries.
  • Synthesis Reference(s)Journal of the American Chemical Society, 75, p. 2947, 1953 DOI: 10.1021/ja01108a047
    The Journal of Organic Chemistry, 26, p. 283, 1961
    Tetrahedron, 40, p. 4981, 1984 DOI: 10.1016/S0040-4020(01)91336-5
  • General DescriptionLight lavender crystals or solid.
  • Air & Water ReactionsInsoluble in water.
  • Reactivity Profile2-Phenylphenol react as a weak organic acid. Exothermically neutralizes bases. May react with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides to generate flammable gas (H2) and the heat of the reaction may ignite the gas. Is sulfonated very readily (for example, by concentrated sulfuric acid at room temperature) in exothermic reactions. May be nitrated very rapidly. Nitrated phenols often explode when heated and also form metal salts that tend toward detonation by rather mild shock. Can react with oxidizing agents .
  • Fire Hazard2-Phenylphenol is combustible.
  • Agricultural UsesFungicide, Disinfectant, Microbiocide: Used to make fungicides. Also used to make dye stuffs and rubber chemicals, but used primarily as a disinfectant cleaner. Registered for use in the U.S. and U.K.
  • Trade nameANTHRAPOLE 73®; DOWCIDE-1®; Invalon OP®; KIWI LUSTR-277®; NECTRYL®; PREVENTOL-O Extra®; REMOL TRF®; TETROSIN OE®; TETROSIN OE-N®; TORSITE®; TUMESCAL OPE®
  • Safety ProfileA poison by intraperitoneal route.Moderately toxic by ingestion and possibly other routes.An experimental teratogen. Other experimentalreproductive effects. Human mutation data reported.Severe eye and moderate skin irritant. Questionablecarcinogen wi
  • Potential Exposureo-Phenylphenol is used in the manufacture of plastics, resins, rubber, as Agricultural chemical, in making fungicides; as an intermediate in making dye stuffs and rubber chemicals; a germicide; used in food packaging.
  • CarcinogenicityIARC classified SOPP as a B2 carcinogen in 1983, based on reports from Japan that high dietary levels of this sodium salt caused bladder tumors in male rats. Both sodium saccharin and sodium cyclamate also cause bladder tumors at high doses in male rats, but classification of these food additives as B2 carcinogens was recently rescinded by IARC at a meeting in 1998.
    The U.S. National Toxicology Program conducted a skin painting study with OPP in groups of 50 mice per sex. The OPP was applied as an acetone solution on 3 days per week for 2 years, both alone and as a promoter with DMBA. No skin neoplasms were observed in either sex treated with OPP alone, and there were no tumor enhancing or inhibiting effects when OPP and DMBA were given in combination.
  • Metabolic pathway2-Phenylphenol is not used on growing plants because it is too phytotoxic and there appears to be no information published on its metabolism in plants. Its widespread use as a preservative, disinfectant and fungistat on stored food (either by direct application or impregnated in packaging) requires studies on its environmental fate and metabolism in mammals. Several studies in mammals are available and the compound has been the subject of an evaluation by the UK MAFF Pesticide Safety Directorate (PSD); the results have been published (PSD, 1993). This evaluation was prompted by the discovery of bladder tumours in rats treated with high doses of the compound.
    2-Phenylphenol is also used as the sodium and potassium salts where water solublity is important. No information is available specifically on the latter. The metabolism of the free phenol and the sodium salt have been studied separately. Once absorbed into a cell, provided that internal pH control is maintained, the two forms should be indistinguishable.
  • ShippingUN3143 Dyes, solid, toxic, n.o.s. or Dye intermediates, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required
  • Purification MethodsCrystallise it from pet ether. [Beilstein 6 IV 4579.]
  • Degradation2-Phenylphenol has limited water solubilty but it is very soluble in base, forming the alkali metal salts. It is a stable compound but it would be expected to react with oxygen to form quinones as do other phenols. The aqueous photolysis of 2-phenylphenol using a high pressure mercury vapour lamp gave phenyl-p-benzoquinone (2) and multi-hydroxylated products (see Scheme 1) (Coulangeon ef al., 1980). Degradation was accelerated by oxygen. The rate of degradation was not given in this paper, the main thrust of which was the primary physical steps in the photolysis process.
    2-Phenylphenol was completely degraded during 14 days exposure to sunlight in aqueous solution under conditions where is was stable for 56 days in the dark (Suzuki et al., 1990). The objective of the study was to demonstrate the photogeneration of mutagens in the presence of nitrate and nitrite. Bacterial mutagens, probably nitro compounds, were formed only in the presence of nitrite.
  • IncompatibilitiesStrong bases, strong oxidizers
  • Waste DisposalIn accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.
2-Phenylphenol Preparation Products And Raw materials
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