2-Phenylphenol CAS 90-43-7
Introduction：Basic information about 2-Phenylphenol CAS 90-43-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
2-Phenylphenol Basic information
| Product Name: | 2-Phenylphenol |
| Synonyms: | BIPHENYL-2-OL;BIPHENYLOL-2;HYDROXY-(2-PHENYL)BENZENE;FEMA 3959;DOWICIDE 1(R);[1,1'-BIPHENYL]-2-OL;AKOS BAR-1742;2-PHENYLPHENOL |
| CAS: | 90-43-7 |
| MF: | C12H10O |
| MW: | 170.21 |
| EINECS: | 201-993-5 |
| Product Categories: | Biphenyl & Diphenyl ether;Aromatic Compounds;Industrial/Fine Chemicals;90-43-7 |
| Mol File: | 90-43-7.mol |
2-Phenylphenol Chemical Properties
| Melting point | 57-59 °C(lit.) |
| Boiling point | 282 °C(lit.) |
| bulk density | 600kg/m3 |
| density | 1.21 |
| vapor pressure | 7 mm Hg ( 140 °C) |
| refractive index | 1.6188 (estimate) |
| FEMA | 3959 | 2-PHENYLPHENOL |
| Fp | 255 °F |
| storage temp. | Store below +30°C. |
| solubility | Soluble in ethanol, acetone, benzene,sodium hydroxide, chloroform, acetonitrile, toluene, hexane, ligroin, ethyl ether, pyridine, ethylene glycol, isopropanol, glycol ethers and polyglycols. |
| pka | 10.01(at 25℃) |
| form | Crystalline Flakes |
| color | White |
| Odor | nearly wh. or lt. buff crystals, mild char. sweetish odor |
| PH | 7 (0.1g/l, H2O, 20℃) |
| biological source | synthetic |
| explosive limit | 1.4-9.5%(V) |
| Water Solubility | 0.7 g/L (20 ºC) |
| Sensitive | Hygroscopic |
| Merck | 14,7304 |
| JECFA Number | 735 |
| BRN | 606907 |
| Stability: | Stable. Combustible. Incompatible with strong oxidizing agents, halogens. |
| Major Application | flavors and fragrances |
| Cosmetics Ingredients Functions | PRESERVATIVE |
| InChI | 1S/C12H10O/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9,13H |
| InChIKey | LLEMOWNGBBNAJR-UHFFFAOYSA-N |
| SMILES | Oc1ccccc1-c2ccccc2 |
| LogP | 3.18 at 22.5℃ |
| CAS DataBase Reference | 90-43-7(CAS DataBase Reference) |
| IARC | 3 (Vol. 73) 1999 |
| NIST Chemistry Reference | o-Hydroxybiphenyl(90-43-7) |
| EPA Substance Registry System | 2-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 | TSCA listed |
| HazardClass | 9 |
| PackingGroup | III |
| HS Code | 29071900 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Aquatic Acute 1 Aquatic Chronic 1 Eye Dam. 1 Skin Irrit. 2 STOT SE 3 |
| Hazardous Substances Data | 90-43-7(Hazardous Substances Data) |
| Toxicity | LD50 orally in rats: 2.48 g/kg (Hodge) |
| Description | 2-phenylphenol(OPP) is a broad spectrum fungicide used to protect crops in storage. It is highly soluble in water, moderately voatile but is not expected to be persistent in the environment. OPP is more selective than other free phenols but does produce phytotoxic effects. |
| Chemical Properties | o-Phenylphenol is a white to buff-colored crystalline solid with a distinct odor. When heated to decomposition, it emits acrid smoke and irritating fumes. |
| Uses | 2-Phenylphenol is a agriculture fungicide and is no longer used as a food additive. |
| Definition | ChEBI: 2-Phenylphenol is 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. It has a role as an environmental food contaminant and an antifungal agrochemical. It derives from a hydride of a biphenyl. |
| Preparation | 2-Phenylphenol 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. |
| Production Methods | OPP is produced as a by-product in the manufacture of diphenyl oxide or by aldol condensation of hexazinone. |
| Application | 2-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. It 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. |
| Synthesis Reference(s) | Journal of the American Chemical Society, 75, p. 2947, 1953 DOI: 10.1021/ja01108a047 Tetrahedron, 40, p. 4981, 1984 DOI: 10.1016/S0040-4020(01)91336-5 The Journal of Organic Chemistry, 26, p. 283, 1961 DOI: 10.1021/jo01060a632 |
| General Description | Light lavender crystals or solid. |
| Air & Water Reactions | Insoluble in water. |
| Reactivity Profile | 2-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 Hazard | 2-Phenylphenol is combustible. |
| Flammability and Explosibility | Non flammable |
| Agricultural Uses | Fungicide, Disinfectant, Microbiocide: Used to make fungicides. Also used to make dyestuffs and rubber chemicals, but used primarily as a disinfectantcleaner. Registered for use in the U.S. and U.K. |
| Trade name | ANTHRAPOLE 73®; DOWCIDE-1®;Invalon OP®; KIWI LUSTR-277®; NECTRYL®;PREVENTOL-O Extra®; REMOL TRF®; TETROSINOE®; TETROSIN OE-N®; TORSITE®; TUMESCALOPE® |
| Safety Profile | A 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 Exposure | o-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. |
| Carcinogenicity | IARC classified SOPP as a B2carcinogen in 1983, based on reports from Japan that high dietary levels of this sodium salt caused bladder tumors inmale rats. Both sodium saccharin and sodiumcyclamate also cause bladder tumors at high doses in malerats, but classification of these food additives as B2 carcinogenswas recently rescinded by IARC at a meeting in 1998. The U.S. National Toxicology Program conducted a skinpainting study with OPP in groups of 50 mice per sex. TheOPP was applied as an acetone solution on 3 days per weekfor 2 years, both alone and as a promoter with DMBA.No skin neoplasms were observed in either sex treatedwith OPP alone, and there were no tumor enhancing orinhibiting effects when OPP and DMBA were given incombination. |
| Metabolic pathway | 2-Phenylphenol is not used on growing plants because it is too phytotoxicand there appears to be no information published on its metabolism inplants. Its widespread use as a preservative, disinfectant and fungistat onstored 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 thesubject of an evaluation by the UK MAFF Pesticide Safety Directorate(PSD); the results have been published (PSD, 1993). This evaluation wasprompted by the discovery of bladder tumours in rats treated with highdoses of the compound. 2-Phenylphenol is also used as the sodium and potassium salts wherewater solublity is important. No information is available specifically onthe latter. The metabolism of the free phenol and the sodium salt havebeen studied separately. Once absorbed into a cell, provided that internalpH control is maintained, the two forms should be indistinguishable. |
| Shipping | UN3143 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 Methods | Crystallise it from pet ether. [Beilstein 6 IV 4579.] |
| Degradation | 2-Phenylphenol is readily degraded in surface waters and municipal waste mixtures, and the degradation is biologically mediated. In river water, radiolabelled 2- phenylphenol at concentrations ranging from 1.2 to 120 μg/litre was degraded to about 50% of the initial concentration in 1 week. The addition of mercuric chloride to inhibit biological activity reduced the decrease to only 10% after 30 days. In activated sludge, radiolabelled 2-phenylphenol at 9.6 mg/litre was degraded to 50% of the initial concentration in 24 h. 2-Phenylphenol therefore meets the criteria to be classified as readily biodegradable (FAO/WHO, 1999). |
| Toxicity evaluation | 2-phenylphenol has a moderate to low toxicity to biodiversity. This substance has a low oral mammalian toxicity, is carcinogenic, a neurotoxin and recognised irritant. 2-Phenylphenol and its sodium salt have a low acute toxicity in mammals when administered orally, with LD50 values ranging from 600 to 3500 mg/kg of body weight. http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/1340.htm |
| Incompatibilities | Strong bases, strong oxidizers |
| Toxics Screening Level | The Initial Risk Screening Level (IRSL) for Ortho-phenylphenol is 1.1 μg/m3 based on an annual averaging time. |
| Waste Disposal | In 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
| Raw materials | Sodium hydroxide-->Sodium carbonate-->Trichloroethylene-->Biphenyl-->2-Aminobiphenyl-->4-Phenylphenol-->Sodium 2-biphenylate-->Dibenzofuran |
| Preparation Products | 4-Phenylphenol-->Sodium 2-biphenylate-->Diflunisal-->dibenzyl biphenyl polyoxyethylene ether-->2-Phenylthiophenol-->2-Biphenylcarboxylic acid-->4-NITRO-2,6-DIPHENYLPHENOL-->o-(Trimethylsilyl)phenol-->2-CYCLOHEXYLCYCLOHEXANOL-->2-METHOXYBIPHENYL-->2,2-BIS(2-HYDROXY-5-BIPHENYLYL)PROPANE-->2,6-Diphenylphenol-->5-[[4-[(2,4-dinitrophenyl)amino]phenyl]azo][1,1'-biphenyl]-2-ol |
