Triphenylphosphit

TPO · P(OPh)3 · (PhO)3P · Weston TPP · PHENYL PHOSPHITE · p36 · EFED · P 36

Identifikatoren & physikalische Daten

CAS No.	101-02-0
Summenformel	C18H15O3P
Durchschnittliche Molmasse	310,3 g/mol
Monoisotopische Masse	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
Lokaler Name	Triphenylphosphit

Chemische & physikalische Eigenschaften

XLogP	5,5
Polarare Oberfläche (TPSA)	27,7
H-Brücken-Donoren	0
H-Brücken-Akzeptoren	3
Frei drehbare Bindungen	6
Schwere Atome	22
Formalladung	0
Komplexität	247
Stoffklassen	Other Classes -> Phosphite Compounds
Polymers	Plastics -> PVC (soft)PVC (rigid)Plastics -> Heat stabilisersPlastics -> Other functions -> Other stabiliser
SpringerMaterials Properties	Chemical shift
Geruch	Pleasant odor
Dichte	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
Löslichkeit	less than 0.1 mg/mL at 68 °F (NTP, 1992)Insoluble in water. Very soluble in ethanol, organic solvents.Solubility in water: nonemethanol: 25 mg/mL, clear
Flammpunkt	425 °F (NTP, 1992)425 °F (218 °C) (OPEN CUP)218 °C o.c.
Siedepunkt	680 °F at 760 mmHg (NTP, 1992)360 °C360 °C (lit.)
Decomposition	When heated to decomp ... emits toxic fumes of /phosphorus oxides/.
Schmelzpunkt	72 to 75 °F (NTP, 1992)25 °C22-25 °C22-24 °C (lit.)
Dampfdichte	>1 (air = 1)10.7 (vs air)
Dampfdruck	5 mm Hg ( 205 °C)
Brechungsindex	n20/D 1.59(lit.)
Lagerbedingungen	Store below +30°C.
Aggregatzustand	Liquid
Farbe	Clear colorless to pale yellow
pH	1 (200g/l, H2O, 20℃)
BRN	1079456
Henry-Konstante	1.8×101 mol/(m3Pa) at 25℃, Zhang et al. (2010)
Dielektrizitätskonstante	3.2(24℃)
Stabilität	Stable. Combustible. Incompatible with strong oxidizing agents.
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 Datenbank	101-02-0(CAS DataBase Reference)
NIST chemische Informationen	Phosphorous acid, triphenyl ester(101-02-0)
EPA chemische Informationen	Triphenyl phosphite (101-02-0)

Sicherheit & Vorschriften

GHS-Einstufung	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)
Regulatorische Informationen	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
DOT-Kennzeichnung	Poison
Brandgefahren	This chemical is combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
Brandpotenzial	COMBUSTIBLECOMBUSTIBLE WHEN EXPOSED TO HEAT OR FLAME
Gesundheitsgefahren	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.
Gefahrenübersicht	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.
Reaktive Gruppe	Sulfonates, Phosphonates, and Thiophosphonates, Organic
EG-Einstufung	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.
Brandbekämpfung	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.
Erste-Hilfe-Maßnahmen	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 .
Erste Hilfe	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.
Sichere Lagerung	Separated from strong oxidants. Well closed.
Brandbekämpfungsverfahren	To fight fire use, use /carbon dioxide/, mist, dry chemical.WATER OR FOAM MAY CAUSE FROTHING.
Freisetung ohne Brand	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.
Entsorgungsverfahren	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.
Verschüttetes entsorgen	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.
Unerwünschte Wirkungen	Neurotoxin - Other CNS neurotoxin
Expositionspfade	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
Wassergefährdungsklasse (WGK)	2
TSCA-Inventar-Status	TSCA listed
UN-Transportnummer	UN 3077 9/PG 3
Zollcode	29209085
RTECS-Nr.	TH1575000
R-Sätze (R)	36/38-50/53
Toxizität	LD50 oral in rat: 444mg/kg
Gefahrensymbole	Xn,N,Xi
Sicherheitshinweise (S)	28-60-61-28A-26
Gefahrenklasse	9Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT RE 2
Verpackungsgruppe	III
Lagerklasse	10 - Combustible liquids
Gefahrstoffdaten	101-02-0(Hazardous Substances Data)

Anwendungen & Verwendung

Verwenden

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.