化工社化工社 化学情報印刷レポート · 研究参考用
亜りん酸トリフェニル
亜りん酸トリフェニル · トリフェニル=ホスファイト · ホスクレールT36 · ドベルホス-10 · トリフェノキシホスフィン · トリフェニルホスファイト · ホスホン酸トリフェニル · トリアルキル亜リン酸エステル
識別子と物理属性
| CAS No. | 101-02-0 |
|---|---|
| 分子式 | C18H15O3P |
| 平均分子量 | 310.3 g/mol |
| 単同位体質量 | 310.07588097 g/mol |
| SMILES | c1ccc(OP(Oc2ccccc2)Oc2ccccc2)cc1 |
| InChIKey | HVLLSGMXQDNUAL-UHFFFAOYSA-N |
| PubChem CID | 7540 |
| ChEMBL | CHEMBL1875503 |
| EC No. | 202-908-4 |
| DTXSID | DTXSID0026252 |
| 現地名 | 亜りん酸トリフェニル |
化学・物理的性質
| XLogP | 5.5 |
|---|---|
| 極性表面積 | 27.7 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 6 |
| 重原子数 | 22 |
| 形式電荷 | 0 |
| 複雑度 | 247 |
| 物質分類 | Other Classes -> Phosphite Compounds |
| Polymers | Plastics -> PVC (soft)PVC (rigid)Plastics -> Heat stabilisersPlastics -> Other functions -> Other stabiliser |
| SpringerMaterials Properties | Chemical shift |
| 臭い | Pleasant odor |
| 密度 | 1.1844 at 68 °F (NTP, 1992) - Denser than waterwill sink1.1842 @ 20 °CRelative density (water = 1): 1.181.184 @25 °C1.184 g/mL at 25 °C (lit.) |
| Color/Form | Water-white to pale yellow solid or oily liquid |
| 溶解度 | less than 0.1 mg/mL at 68 °F (NTP, 1992)Insoluble in water. Very soluble in ethanol, organic solvents.Solubility in water: noneメタノール: 25 mg/mL、透明不溶性 |
| 引火点 | 425 °F (NTP, 1992)425 °F (218 °C) (OPEN CUP)218 °C o.c. |
| 沸点 | 680 °F at 760 mmHg (NTP, 1992)360 °C360 °C (lit.) |
| Decomposition | When heated to decomp ... emits toxic fumes of /phosphorus oxides/. |
| 融点 | 72 to 75 °F (NTP, 1992)25 °C22-25 °C22-24 °C (lit.) |
| 蒸気密度 | >1 (air = 1)10.7 (vs air) |
| 蒸気圧 | 5 mm Hg ( 205 °C) |
| 屈折率 | n20/D 1.59(lit.) |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | 液体 |
| 色 | 無色透明～淡黄色 |
| pH | 1 (200g/l, H2O, 20℃) |
| BRN | 1079456 |
| ヘンリー定数 | 1.8×101 mol/(m3Pa) at 25℃, Zhang et al. (2010) |
| 誘電率 | 3.2(24℃) |
| 安定性 | 安定。可燃性。強力な酸化剤とは相容れない。 |
| InChI | 1S/C18H15O3P/c1-4-10-16(11-5-1)19-22(20-17-12-6-2-7-13-17)21-18-14-8-3-9-15-18/h1-15H |
| InChIKey | HVLLSGMXQDNUAL-UHFFFAOYSA-N |
| SMILES | O(P(Oc1ccccc1)Oc2ccccc2)c3ccccc3 |
| CAS データベース | 101-02-0(CAS DataBase Reference) |
| NISTの化学物質情報 | Phosphorous acid, triphenyl ester(101-02-0) |
| EPAの化学物質情報 | Triphenyl phosphite (101-02-0) |
化学的特性
Water-white to pale-yellow solid or oily liquid; pleasant odor. Combustible.
安全性と法規制
| GHS 分類 | WarningH315: Causes skin irritation [Warning Skin corrosion/irritation]P264, P264+P265, P273, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)H302 (43.6%): Harmful if swallowed [Warning Acute toxicity, oral]P260, P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement) |
|---|---|
| 規制情報 | Chemical: Phosphorous acid, triphenyl esterPhosphorous acid, triphenyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phosphorous acid, triphenyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 28-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14793Triphenyl phosphite: Does not have an individual approval but may be used under an appropriate group standard |
| 輸送ラベル（DOT） | Poison |
| 火災危険 | This chemical is combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| 火災の可能性 | COMBUSTIBLECOMBUSTIBLE WHEN EXPOSED TO HEAT OR FLAME |
| 健康有害性 | SYMPTOMS: This compound exhibits symptoms similar to those caused by phenols: dizziness muscle weaknessdimness of visionringing in the earsirregular and rapid breathingweak pulseshortness of breath. All these may be followed by loss of consciousness, collapse and death. |
| 有害性の概要 | Reacts with waterA skin, eye, and respiratory tract irritantMay cause skin sensitizationHigh concentrations may cause nervous system effects[ICSC] An eye and severe skin irritantA mild sensitizerEmergency treatment: TOCP and related agentsFollowing exposure to >6-7 mg/kg of TOCP, patients have acute GI symptoms of vomiting, diarrhea and abdominal painAfter a delay of 8-35 days, patients develop peripheral neuropathy (flaccid paralysis) that resolves over the next 2-3 months in some patientsSome patients remain permanently paralyzed[HSDB] Causes flaccid paralysis in rats after subcutaneous doses >2000 mg/kg[RTECS] A skin irritant[CAMEO] A skin and eye irritant[eChemPortal: ESIS] An irritantHarmful if swallowedToxic to aquatic organisms[MSDSonline] See Triorthocresyl phosphate. |
| 反応性グループ | Sulfonates, Phosphonates, and Thiophosphonates, Organic |
| EC 分類 | Symbol: Xi, NR: 36/38-50/53S: (2)-28-60-61 |
| Reactivity Profile | Organophosphates, such as TRIPHENYL PHOSPHITE, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides. |
| Chemical Dangers | Decomposes on burning. This produces toxic fumes including phosphorus oxides. Reacts with strong oxidants. Reacts with water. |
| Air and Water Reactions | Insoluble in water. |
| NFPA Hazard Classification | 0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.0 - Materials that in themselves are normally stable, even under fire conditions. |
| 消火 | Fires involving this compound should be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)Use water spray, powder, foam, carbon dioxide. |
| 応急処置措置 | Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Refer for medical attention . |
| 応急処置 | 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. |
| 安全保管 | Separated from strong oxidants. Well closed. |
| 消火手順 | To fight fire use, use /carbon dioxide/, mist, dry chemical.WATER OR FOAM MAY CAUSE FROTHING. |
| 非火災時の漏出対応 | SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed 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. |
| 処分方法 | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| 漏出処分 | Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| Eye Prevention | Wear safety goggles or face shield. |
| Fire Prevention | NO open flames. |
| Inhalation Risk | No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C. |
| 有害作用 | Neurotoxin - Other CNS neurotoxin |
| 暴露経路 | The substance can be absorbed into the body by inhalation of its aerosol and by ingestion. |
| Signs and Symptoms | Cough. Sore throat.Redness. Pain. |
| TSCA Test Submissions | The ability of triphenyl phosphite to increase the incidence of micronucleated polychromatic erythrocytes was evaluated in the bone marrow of CD-1 mice. Based on preliminary toxicity determinations, three groups of mice (5/sex/group) were treated with total doses of 1250, 2500 and 5000mg/kg of test material as two equal oral administrations separated by an interval of 24 hours. Animals at the highest dose level experienced tremors and 5 mortalities. The incidence of micronucleated cells were analyzed in 1000 polychromatic erythrocytes per animal. The incidence of micronucleated polychromatic erythrocytes and the ratio of normochromatic to polychromatic erythrocytes were comparable to the vehicle control (corn oil). |
| Human Toxicity Excerpts | ...TRIPHENYLPHOSPHITE IS STRONG IRRITANT SUBSTANCE & MILD SENSITIZER....TRIPHENYL...PHOSPHITE ARE DELAYED NEUROTOXINS LACKING POTENT ANTI-CHOLINESTERASE PROPERTIES.NONE OF THESE COMPD /PHOSPHATE & PHOSPHITE ESTERS/ PRODUCES TYPICAL SYMPTOMS ASSOCIATED WITH CHOLINESTERASE INHIBITION... |
| Non-Human Toxicity Excerpts | ...TRIPHENYL PHOSPHITE...PRODUCE/S/ TYPICAL FLACCID PARALYSIS IN CATS, DOGS, & MONKEYSTREMORS, DIARRHEA, VASODILATATION BY ALL ROUTESNO PARALYSIS IN SURVIVORS. INHIBITION OF CHOLINESTERASE IN WHOLE BLOOD IN MICE. SKIN & EYE IRRITANT. /FROM TABLE/TRIPHENYL PHOSPHITE DID NOT SHOW IRRITATING OR RESORPTIVE EFFECTS WHEN APPLIED TO SKIN OF MICE, BUT CAUSED DERMATITIS WHEN APPLIED TO SKIN OF GUINEA PIGSALSO HAD SENSITIZING ACTION.THRESHOLD DOSES CAUSING CHANGES IN FUNCTION OF RABBIT NERVOUS SYSTEM WAS 17 MG/KG FOR TRIPHENYL PHOSPHATE.For more Non-Human Toxicity Excerpts (Complete) data for TRIPHENYL PHOSPHITE (7 total), please visit the HSDB record page. |
| Antidote and Emergency Treatment | /SRP:/ Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 m1/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Administer activated charcoal ... . If product was ingested, protect yourself from contact with vomitus as it may cause burns. /Phosphorus and related compounds//SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload. Treat seizures with diazepam ... . Monitor for signs of hypoglycemia and administer 50% dextrose if necessary. Draw blood sample before administration ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Phosphorus and related compounds/ |
| Toxicity Data | LC (rat) > 6,700 mg/m3/4h |
| Non-Human Toxicity Values | LD50 MICE ORAL 1330 MG/KGLD50 Rat oral 1600 mg/kgLD50 Mouse ip 1167 mg/kg |
| 水環境危害等級（WGK） | 2 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | TH1575000 |
| 輸送番号（UN） | UN 3077 9/PG 3 |
| 毒性 | LD50 oral in rat: 444mg/kg |
| 税関コード | 29209085 |
| 危険文句（R） | 36/38-50/53 |
| 化審法 | (3)-2501 |
| 消防法 | 危-4-4-III |
| 危険表示 | Xn,N,Xi |
| 安全措置（S） | 28-60-61-28A-26 |
| 危険等級 | 9Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT RE 2 |
| 包装等級 | III |
| 貯蔵分類 | 10 - Combustible liquids |
| 有害物質データ | 101-02-0(Hazardous Substances Data) |
用途
解説
C18H15O3P(310.29)．(C6H5O)3P．亜リン酸トリフェニル(triphenylphosphite)ともいう．三塩化リンと3倍 mol のフェノールとを第三級アミン存在下に反応させると得られる．無色の結晶．融点25 ℃，沸点220 ℃(1.5 kPa)．nD25"1.587．d2525"1.183．メタノール，アセトン，エーテルに可溶，水に不溶．各種合成樹脂の安定剤，石油製品の酸化防止剤として卓効を示す．森北出版「化学辞典（第2版）
用途
各種合成樹脂の安定剤。石油製品の酸化防止剤。各種亜リン酸エステルの中間体。
使用
Triphenyl phosphite can be used:As a source of phosphorus and as a ligand for the synthesis of transition metal phosphide nanoparticles via heating-up process.To convert alcohols to alkyl halides.As a peptide coupling agent.As a low-temperature source of singlet oxygen after forming an adduct with ozone.To synthesize bromotriphenoxyphosphonium bromide, a brominating agent, by reacting with bromine.
製法・合成法
純化方法
Its ethereal solution is washed succesively with aqueous 5% NaOH, distilled water and saturated aqueous NaCl, then dried with Na2SO4 and distilled under vacuum after evaporating the diethyl ether. [Walsh J Am Chem Soc 81 3023 1959, Verkade & Coskren in Organo Phosphorus Compounds (Kosolapoff & Maier eds) Wiley Vol 6 pp 211-577 1973, Beilstein 6 IV 695.]