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Triphenyl phosphite

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Name

Triphenyl phosphite

EINECS 202-908-4
CAS No. 101-02-0 Density 1.184 g/mL at 25 °C(lit.)
PSA 41.28000 LogP 5.45030
Solubility insoluble in water Melting Point 22-24 °C
Formula C18H15O3P Boiling Point 360 °C at 760 mmHg
Molecular Weight 310.289 Flash Point 218.3 °C
Transport Information UN 3077 9/PG 3 Appearance colourless to pale yellow liquid
Safety 28-60-61-28A Risk Codes 36/38-50/53
Molecular Structure Molecular Structure of 101-02-0 (Triphenyl phosphite) Hazard Symbols HarmfulXn,DangerousN,IrritantXi
Synonyms

Phenylphosphite ((C6H5O)3P) (6CI,7CI);ADK Stab TPP;Advance TPP;Doverphos 10;Irgafos TPP;Irgastab CH 55;Mark TPP;Mellite 310;Phosclere T 36;Plastistab 2334;Sumilizer TPP-R;Sumilizer TTP-R;TPP (plasticizer);TPP-R;Triphenoxyphosphine;Tris(phenoxy)phosphine;Weston TPP;

Article Data 73

Triphenyl phosphite Synthetic route

108-95-2

phenol

101-02-0

triphenyl phosphite

Conditions
ConditionsYield
With Hexamethylphosphorous triamide In toluene at 130℃; for 8h; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction;100%
With phosphorus trichloride at 35 - 160℃; under 7.50075 Torr; for 6h; Temperature; Flow reactor; Inert atmosphere;94%
With 1H-imidazole; carbon disulfide; Hexamethylphosphorous triamide In benzene at 20 - 25℃; for 24h;86%

triphenylphosphite-borane complex

101-02-0

triphenyl phosphite

Conditions
ConditionsYield
With tert-butyl alcohol; 4 A molecular sieve In tetrahydrofuran at 25℃; for 72h;100%
With piperazinomethyl polystyrene resin In toluene at 60℃; for 1.5h;
4519-35-1

phenylphosphonic acid bis(N,N-diethylamide)

62-53-3

aniline

A

101-02-0

triphenyl phosphite

B

15159-51-0

N,N',N''-triphenylphosphorous triamide

C

26350-11-8

phenyl N,N'-diphenylphosphorodiamidite

D

26350-10-7

diphenyl phenylphosphoramidite

E

109-89-7

diethylamine

Conditions
ConditionsYield
for 17h; Product distribution; Heating;A n/a
B n/a
C n/a
D n/a
E 94.5%
4519-35-1

phenylphosphonic acid bis(N,N-diethylamide)

106-40-1

4-bromo-aniline

A

101-02-0

triphenyl phosphite

B

109-89-7

diethylamine

C

diphenyl (p-bromophenyl)phosphoramidite

D

phenyl N,N'-bis(p-bromophenyl)phosphorodiamidite

E

N,N',N''-tris(p-bromophenyl)phosphorous triamide

Conditions
ConditionsYield
for 22h; Product distribution; Heating;A n/a
B 91.4%
C n/a
D n/a
E n/a
67-56-1

methanol

7719-12-2, 52843-90-0

phosphorus trichloride

A

101-02-0

triphenyl phosphite

B

18351-42-3

dimethyl phenylphosphonite

C

7526-26-3

diphenyl methylphosphonate

Conditions
ConditionsYield
Stage #1: phosphorus trichloride; phenol at 65 - 250℃; for 3 - 4h;
Stage #2: methanol; methyl iodide at 210 - 250℃; for 1h; Product distribution / selectivity;
A 4.5%
B 4.8%
C 85.5%
139-02-6

sodium phenoxide

108-95-2

phenol

101-02-0

triphenyl phosphite

Conditions
ConditionsYield
With tetrachloromethane; phosphorous; 15-crown-5 at 50 - 70℃; for 3h;85%
160067-03-8

2-diethylamino-5-methyl-1,3,2-oxathiaphospholene

108-95-2

phenol

101-02-0

triphenyl phosphite

Conditions
ConditionsYield
at 20℃; for 2h;85%
108-95-2

phenol

A

101-02-0

triphenyl phosphite

B

115-86-6

phosphoric acid triphenyl ester

Conditions
ConditionsYield
With pyridine In acetonitrile at 50℃; electrosynthesis;A 78%
B 20%
73569-84-3

chlorotriphenoxy(trichloroacetyl)phosphorane

A

101-02-0

triphenyl phosphite

B

5382-00-3

Diphenyl phosphorochloridite

C

76-02-8

Trichloroacetyl chloride

Conditions
ConditionsYield
at 50℃; under 10 Torr; Mechanism;A n/a
B n/a
C 63.6%
3582-11-4

trichloromethylphosphonous dichloride

108-95-2

phenol

A

101-02-0

triphenyl phosphite

B

67-66-3

chloroform

C

115-86-6

phosphoric acid triphenyl ester

Conditions
ConditionsYield
A 55.6%
B 34%
C 6.7%

Triphenyl phosphite Chemical Properties

Molecular Structure of Triphenyl phosphite (CAS NO.101-02-0):

IUPAC Name: triphenyl phosphite 
Empirical Formula: C18H15O3P
Molecular Weight: 310.2837
H bond acceptors: 3
H bond donors: 0
Freely Rotating Bonds: 6
Polar Surface Area: 41.28 Å2
Flash Point: 218.3 °C
Enthalpy of Vaporization: 58.18 kJ/mol
Boiling Point: 360 °C at 760 mmHg
Denny: 1.184 g/mL at 25 °C(lit.)
Vapour Pressure: 4.74E-05 mmHg at 25°C
Water solubility: insoluble
Melting point: 22-24 ºC
EINECS: 202-908-4
Sensitive: Air & Moisture Sensitive
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
Product Categories: Catalysis and Inorganic Chemistry; Phosphite Ligands; Phosphorus Compounds
InChI
InChI=1/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
Smiles
P(Oc1ccccc1)(Oc1ccccc1)Oc1ccccc1

Triphenyl phosphite Uses

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

Triphenyl phosphite Production

Triphenyl phosphite is prepared from phosphorus trichloride and phenol in the presence of a base:
PCl3 + 3 HOC6H5 → P(OC6H5)3 + 3HCl
Trimethyl phosphine is prepared from triphenylphosphite:
3 CH3MgBr + P(OC6H5)3 → P(CH3)3 + 3 MgBrOC6H5

Triphenyl phosphite Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intraperitoneal 100mg/kg (100mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR
National Technical Information Service. Vol. OTS0570901,
cat LDLo subcutaneous 300mg/kg (300mg/kg) BEHAVIORAL: ATAXIA Journal of Pharmacology and Experimental Therapeutics. Vol. 49, Pg. 78, 1933.
chicken LDLo intravenous 50mg/kg (50mg/kg) AUTONOMIC NERVOUS SYSTEM: GAGLION BLOCK Nippon Eiseigaku Zasshi. Japanese Journal of Hygiene. Vol. 44, Pg. 118, 1989.
chicken LDLo oral 250mg/kg (250mg/kg) BEHAVIORAL: ATAXIA National Technical Information Service. Vol. OTS0532280,
chicken LDLo subcutaneous 375mg/kg (375mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

BEHAVIORAL: ATAXIA
National Technical Information Service. Vol. OTS0532280,
mammal (species unspecified) LD50 intraperitoneal 250mg/kg (250mg/kg) BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES

CARDIAC: OTHER CHANGES

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 5, Pg. 311, 1952.
mouse LD50 intraperitoneal 266mg/kg (266mg/kg)   Agricultural and Biological Chemistry. Vol. 31, Pg. 1288, 1967.
mouse LD50 oral 1080mg/kg (1080mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(12), Pg. 53, 1987.
mouse LD50 unreported 1360mg/kg (1360mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 21(9), Pg. 55, 1977.
rabbit LDLo skin 5gm/kg (5000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) National Technical Information Service. Vol. OTS0532280,
rat LC inhalation > 6700mg/m3/1H (6700mg/m3)   National Technical Information Service. Vol. OTS0532280,
rat LD50 intraperitoneal 250mg/kg (250mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1117, 1986.
rat LD50 oral 444mg/kg (444mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 46(12), Pg. 13, 1981.
rat LD50 unreported 1490mg/kg (1490mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 21(9), Pg. 55, 1977.
rat LDLo subcutaneous 2gm/kg (2000mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: TREMOR

BEHAVIORAL: MUSCLE WEAKNESS
Journal of Pharmacology and Experimental Therapeutics. Vol. 49, Pg. 78, 1933.

Triphenyl phosphite Consensus Reports

Reported in EPA TSCA Inventory.

Triphenyl phosphite Safety Profile

Poison by intraperitoneal and subcutaneous routes. Moderately toxic by ingestion. An experimental eye and severe human skin irritant. Combustible when exposed to heat or flame. To fight fire, use CO2, mist, dry chemical. When heated to decomposition, it emits toxic fumes of POx. See also Phenol.
Hazard Codes: HarmfulXnDangerousN,IrritantXi
Risk Statements: 36/38-50/53
R36/38:Irritating to eyes and skin. 
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 28-60-61-28A
S28:After contact with skin, wash immediately with plenty of soap-suds. 
S60:This material and its container must be disposed of as hazardous waste. 
S61:Avoid release to the environment. Refer to special instructions / safety data sheets. 
S28:After contact with skin, wash immediately with plenty of soap-suds.
RIDADR: UN 3077 9/PG 3
WGK Germany: 2
RTECS: TH1575000
HazardClass: 9
PackingGroup: III
HS Code: 29209085

Triphenyl phosphite Specification

  Triphenyl phosphite , with CAS number of 101-02-0, can be called phosphorous acid, triphenyl ester ; Advance TPP ; Phenyl phosphite ; Sumilizer TPP-R ; Trifenoxyfosfin ; Tris(phenoxy)phosphine . It is a colourless to pale yellow liquid, be insoluble in water. Triphenyl phosphite (CAS NO.101-02-0) are susceptible to form highly toxic and flammable phosphine gas in the presence of strong reducing agents, such as hydrides. Partial oxidation may result in the release of toxic phosphorus oxides.

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