基本情報
- 標準SMILES
c1ccc(OP(Oc2ccccc2)Oc2ccccc2)cc1- InChIKey
HVLLSGMXQDNUAL-UHFFFAOYSA-N- 分子式
- C18H15O3P
- 平均分子量
- 310.3 g/mol
- 単同位体質量
- 310.07588097
概要
Triphenyl phosphite is a clear, pale yellow liquid with a clean, pleasant odor. (NTP, 1992)
名称と識別子
- 優先名称
- Triphenyl phosphite
- IUPAC
- triphenyl phosphite
- 現地名
- 亜りん酸トリフェニル
- 英語名
- Triphenyl phosphite
- 分子式
- C18H15O3P
- 分子量
- 310.28
名称と別名
名称をさらに表示
データベース識別子
- CAS
101-02-0- PubChem CID
- 7540
- DTXSID
DTXSID0026252- ChEMBL
CHEMBL1875503- UNII
- 9P45GRD24X
- EC Number
- 202-908-4
- Nikkaji
- J3.594G
物性
構造計算による物性
- XLogP
- 5.5
- 極性表面積
- 27.7 Ų
- 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
実験および物理化学的性質
Polymers
Plastics -> PVC (soft); PVC (rigid)
Plastics -> Heat stabilisers
Plastics -> Other functions -> Other stabiliser
Density
1.1844 at 68 °F (NTP, 1992) - Denser than water; will sink
1.1842 @ 20 °C
Relative density (water = 1): 1.18
1.184 @25 °C
Solubility
less than 0.1 mg/mL at 68 °F (NTP, 1992)
Insoluble in water. Very soluble in ethanol, organic solvents.
Solubility in water: none
Flash Point
425 °F (NTP, 1992)
425 °F (218 °C) (OPEN CUP)
218 °C o.c.
Boiling Point
680 °F at 760 mmHg (NTP, 1992)
360 °C
360 °C
Melting Point
72 to 75 °F (NTP, 1992)
25 °C
22-25 °C
物理化学的性質
- 融点
- 22 · 22-24 °C (lit.)
- 沸点
- 360 °C · 360 °C (lit.)
- 比重(密度)
- 1.184 g/mL · 1.184 g/mL at 25 °C (lit.)
- 蒸気密度
- 10.7 · 10.7 (vs air)
- 蒸気圧
- 5 mm · 5 mm Hg ( 205 °C)
- 屈折率
- 20 · n20/D 1.59(lit.)
- 闪点
- 425 °F · 425 °F
- 貯蔵温度
- 30 °C · Store below +30°C.
- 溶解性
- 25 mg/mL、透明 · メタノール: 25 mg/mL、透明
- 外見
- 液体
- 色
- 無色透明~淡黄色
- PH
- 1 · 1 (200g/l, H2O, 20℃)
- 水溶解度
- 不溶性
- BRN
- 1079456 · 1079456
- Henry's Law Constant
- 1.8 · 1.8×101 mol/(m3Pa) at 25℃, Zhang et al. (2010)
- Dielectric constant
- 3.2 · 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 · 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)
化学的性質
化学的特性Water-white to pale-yellow solid or oily liquid; pleasant odor. Combustible.
安全と法規制
GHS分類
GHS Classification
Warning
H315: 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)
Warning
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)
危険有害性情報
Regulatory Information
Chemical: Phosphorous acid, triphenyl ester
Phosphorous 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/14793
Triphenyl phosphite: Does not have an individual approval but may be used under an appropriate group standard
Fire Hazards
This chemical is combustible. (NTP, 1992)
Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
Fire Potential
COMBUSTIBLE
COMBUSTIBLE WHEN EXPOSED TO HEAT OR FLAME
Health Hazards
SYMPTOMS: This compound exhibits symptoms similar to those caused by phenols: dizziness muscle weakness; dimness of vision; ringing in the ears; irregular and rapid breathing; weak pulse; shortness of breath. All these may be followed by loss of consciousness, collapse and death.
Hazards Summary
Reacts with water; A skin, eye, and respiratory tract irritant; May cause skin sensitization; High concentrations may cause nervous system effects; [ICSC] An eye and severe skin irritant; A mild sensitizer; Emergency treatment: TOCP and related agents; Following exposure to >6-7 mg/kg of TOCP, patients have acute GI symptoms of vomiting, diarrhea and abdominal pain; After a delay of 8-35 days, patients develop peripheral neuropathy (flaccid paralysis) that resolves over the next 2-3 months in some patients; Some 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 irritant; Harmful if swallowed; Toxic to aquatic organisms; [MSDSonline] See Triorthocresyl phosphate.
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.
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.
安全と保護具
Fire Fighting
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.
First Aid Measures
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 .
First Aid
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.
Fire Fighting Procedures
To fight fire use, use /carbon dioxide/, mist, dry chemical.
WATER OR FOAM MAY CAUSE FROTHING.
Nonfire Spill Response
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.
Disposal Methods
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.
Spillage Disposal
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.
毒性情報
Signs and Symptoms
Cough. Sore throat.
Redness. Pain.
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, & MONKEYS
TREMORS, DIARRHEA, VASODILATATION BY ALL ROUTES; NO 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 PIGS; ALSO 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/
Non-Human Toxicity Values
LD50 MICE ORAL 1330 MG/KG
LD50 Rat oral 1600 mg/kg
LD50 Mouse ip 1167 mg/kg
安全データ
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- TH1575000
- ridadr
- UN 3077 9/PG 3
- 毒性
- LD50 oral in rat: 444mg/kg
- hs_code
- 29209085
- risk_code
- 36/38-50/53
- 化審法
- (3)-2501
- 消防法
- 危-4-4-III
- hazard_code
- Xn,N,Xi
- safety_code
- 28-60-61-28A-26
- hazard_class
- 9
- packing_group
- III
- Hazard Classifications
- Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT RE 2
- ストレージクラス
- 10 - Combustible liquids
- 有毒物質データの
- 101-02-0(Hazardous Substances Data)
化学と産業
薬理情報
Absorption, Distribution and Excretion
...(32)P-LABELED TRIPHENYL PHOSPHITE (0.3 ML/KG) IP IN CATS, INDICATED CONSIDERABLE HYDROLYSIS & ONLY SMALL AMT OF LABELED PHOSPHORUS IN CNS. ... PRESENCE OF SMALL CONCN OF PHOSPHOROUS ACID IN NERVOUS TISSUE MAY BE RELATED TO DEGENERATIVE CHANGES...
ABSORBED THROUGH GUINEA PIG SKIN. /FROM TABLE/
用途と製造
Uses
Used as a stabilizer/antioxidant (rubber and plastics industries), metal scavenger, epoxy resin diluent, and insecticide synergist; [HSDB] Used as a reducing agent and in paints, lacquers, and varnishes; [IUCLID]
Painting (Pigments, Binders, and Biocides) [Category: Paint]
Chemical intermediate, stabilizer systems for resins, metal scavenger, diluent for epoxy resins.
ANTIOXIDANT FOR SYN RUBBERS
STABILIZER IN RUBBER & PLASTICS INDUSTRY
COLOR STABILIZER IN ALKYD RESINS
Methods of Manufacturing
REACTION OF PHOSPHORUS TRICHLORIDE & PHENOL IN THE PRESENCE OF A TERTIARY AMINE
The commercial production method for triphenyl phosphite is believed to be based on the reaction of phenol and phosphorus trichloride in a moisture-free atmosphere.
Use Classification
Plastics -> Polymer Type -> PVC (soft); PVC (rigid)
Plastics -> Heat stabilisers
Plastics -> Other functions -> Other stabiliser
General Manufacturing Information
Synthetic Rubber Manufacturing
Phosphorous acid, triphenyl ester: ACTIVE
TRIPHENYL PHOSPHITE USED TO SYNTHESIZE HERBICIDE N-(O,O-DIPHENYLPHOSPHONOMETHYL)GLYCINE ETHYL ESTER.
TRIPHENYL PHOSPHITE DID NOT REACT WITH FERROUS CYTOCHROME P 450 & ITS DENATURED FORM, CYTOCHROME P 420, TO PRODUCE COMPLEXES HAVING 2 PEAKS IN SORET REGION OF OPTICAL DIFFERENCE SPECTRA.
TPP STRONGLY SYNERGIZED TOXICITY OF MALATHION & DIMETHOATE AGAINST RESISTANT GREEN LEAFHOPPER.
応用分野
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.
調製方法
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.]
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