Triphenyl phosphite

HCID 7540CAS 101-02-0

Basic information

Standard SMILES
c1ccc(OP(Oc2ccccc2)Oc2ccccc2)cc1
InChIKey
HVLLSGMXQDNUAL-UHFFFAOYSA-N
Molecular formula
C18H15O3P
Average molar mass
310.3 g/mol
Monoisotopic mass
310.07588097

Overview

Triphenyl phosphite is a clear, pale yellow liquid with a clean, pleasant odor. (NTP, 1992)

Names & identifiers

Preferred name
Triphenyl phosphite
IUPAC
triphenyl phosphite
English name
Triphenyl phosphite
Molecular formula
C18H15O3P
Molecular weight
310.28

Names & synonyms

TRIPHENYL PHOSPHITE101-02-0Phosphorous acid, triphenyl esterTriphenoxyphosphinePhenyl phosphiteAdvance TPPTris(phenoxy)phosphineSumilizer TPP-RTrifenoxyfosfinTrifenylfosfitStabilizer P 36Phosclere T 36
Show more names
TPOP(OPh)3(PhO)3Pp36P 36SK28jp360
EFEDMellite 310P 36 (stabilizer)Sumilizer TTP-RWeston TPPTPP (plasticizer)ADK Stab TPPTP 1 (plasticizer)

Database identifiers

CAS
101-02-0
PubChem CID
7540
DTXSID
DTXSID0026252
ChEMBL
CHEMBL1875503
UNII
9P45GRD24X
EC Number
202-908-4
Nikkaji
J3.594G

Properties

Computed structural properties

XLogP
5.5
Topological polar surface area
27.7 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
6
Heavy atoms
22

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Phosphite Compounds
Polymers · 3 items

Plastics -> PVC (soft); PVC (rigid)

Plastics -> Heat stabilisers

Plastics -> Other functions -> Other stabiliser

SpringerMaterials PropertiesChemical shift
OdorPleasant odor
Density · 4 items

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

Color/FormWater-white to pale yellow solid or oily liquid

Physicochemical properties

Melting point
22 · 22-24 °C (lit.)
Boiling point
360 °C · 360 °C (lit.)
Density
1.184 g/mL · 1.184 g/mL at 25 °C (lit.)
vapor density
10.7 · 10.7 (vs air)
vapor pressure
5 mm · 5 mm Hg ( 205 °C)
refractive index
20 · n20/D 1.59(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

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)

Hazard information

Regulatory Information · 4 items

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

DOT LabelPoison
Fire Hazards · 2 items

This chemical is combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Fire Potential · 2 items

COMBUSTIBLE

COMBUSTIBLE WHEN EXPOSED TO HEAT OR FLAME

Health Hazards · 1 item

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 · 1 item

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.

Safety & protection

Fire Fighting · 2 items

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 · 4 items

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 · 1 item

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.

Safe StorageSeparated from strong oxidants. Well closed.
Fire Fighting Procedures · 2 items

To fight fire use, use /carbon dioxide/, mist, dry chemical.

WATER OR FOAM MAY CAUSE FROTHING.

Nonfire Spill Response · 1 item

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.

Toxicology

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol and by ingestion.
Signs and Symptoms · 3 items

Cough. Sore throat.

Redness. Pain.

Redness. Pain.

TSCA Test Submissions · 1 item

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 · 3 items

...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 · 5 items

...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.

Safety data

wgk
2
tsca
TSCA listed
rtecs
TH1575000
ridadr
UN 3077 9/PG 3
hs_code
29209085
Toxicity
LD50 oral in rat: 444mg/kg

Chemistry & industry

Pharmacology

Metabolism/Metabolites...LIKELY THAT.../TRIPHENYL PHOSPHITE/ MAY BE HYDROLYZED READILY.
Absorption, Distribution and Excretion · 2 items

...(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/

Uses & manufacturing

Uses · 6 items

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

U.S. Production2023: 10,000,000 - <25,000,000 lb
Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesStabilizing agent
Methods of Manufacturing · 2 items

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 · 3 items

Plastics -> Polymer Type -> PVC (soft); PVC (rigid)

Plastics -> Heat stabilisers

Plastics -> Other functions -> Other stabiliser

Applications · 5 items

Uses(1) Triphenyl phosphite is used as chelating agents, plastics antioxidant, alkyd resin and pesticide intermediate raw material. (2) It is used for synthetic rubber and resin stabilizer, PVC antioxidant, alkyd resin and pesticide intermediate raw material. (3) Triphenyl phosphite is used as secondary antioxidants, it has effect of light stability, it is suitable for polyvinyl chloride, polypropylene, polystyrene, polyester, ABS resin, and epoxy resin. (4) It is used as chelating agent in PVC products, it can enable products to maintain transparency, and suppresse color change. It can also be used for the production of trimethyl phosphite. (5) Antioxidants, stabilizers TPPi is mainly applied to polyvinyl chloride, polyethylene, polypropylene, polystyrene, polyester, ABS resin, epoxy resin, synthetic rubber antioxidant stabilizer for PVC vinyl products as chelating agent, when the metal is as based stabilizer, coordinating with the product can reduce the harm of metal chloride (6) Chelating agent. Plastic products antioxidant. The synthesis of alkyd resins and polyester resins. (7) Chelating agent. Plastic products antioxidant. The synthesis of alkyd resins and polyester resins. (8) Chelating agent, it is widely used in all kinds of PVC products, it can enable products to maintain its transparency and suppress color change, and it can increase the antioxidant and light and heat stability of the primary stabilizer. In addition, the product is also used for PE, PP, ABS, SBS and other products, and it can be used for pesticide intermediates. It can be used for synthetic alkyd resins and polyester materials and polyester resins.

UsesTriphenyl phosphite (TPP) is the chemical compound with the formula P(OC6H5)3. This colourless viscous liquid is the ester of phosphorous acid and phenol. It is used as a ligand in organometallic chemistry. Nickel complexes of this ligand are homogeneous catalysts for the hydrocyanation of alkenes.

UsesStabilizer/antioxidant for vinyl plastics and polyethylene, polypropylene, styrene copolymers, and rubber.

UsesTriphenyl 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.

UsesChemical intermediate, stabilizer systems for resins, metal scavenger, diluent for epoxy resins.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]

Related reactions

321 records

Linked notes

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