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Triphenylphosphine

Triphenylphosphine Structure
CAS No.
603-35-0
Chemical Name:
Triphenylphosphine
Synonyms
PPh3;Triphenylphosphane;Triphenyl phosphine;Triphenyl;Triphenyphosphine;triphenyl-phosphane;TRIPHENYLPHOSPHORUS;LPO Assay Triphenylphosphine;PP-360;'LGC' (4006)
CBNumber:
CB8771461
Molecular Formula:
C18H15P
Molecular Weight:
262.29
MOL File:
603-35-0.mol
MSDS File:
SDS
Modify Date:
2024/7/26 17:49:17

Triphenylphosphine Properties

Melting point 79-81 °C(lit.)
Boiling point 377 °C(lit.)
Density 1.132
vapor density 9 (vs air)
vapor pressure 5 mm Hg ( 20 °C)
refractive index 1.6358
Flash point 181 °C
storage temp. Store below +30°C.
solubility water: soluble0.00017 g/L at 22°C
form Crystals, Crystalline Powder or Flakes
Specific Gravity 1.132
color White
Odor odorless
Water Solubility Insoluble
Hydrolytic Sensitivity 8: reacts rapidly with moisture, water, protic solvents
Merck 14,9743
BRN 610776
Stability Stable. Incompatible with oxidizing agents, acids.
InChIKey RIOQSEWOXXDEQQ-UHFFFAOYSA-N
CAS DataBase Reference 603-35-0(CAS DataBase Reference)
NIST Chemistry Reference Phosphine, triphenyl-(603-35-0)
EPA Substance Registry System Triphenylphosphine (603-35-0)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS05,GHS07,GHS08
Signal word  Danger
Hazard statements  H302-H317-H318-H372
Precautionary statements  P260-P280-P301+P312-P302+P352-P305+P351+P338-P314
Hazard Codes  Xn,N
Risk Statements  22-43-53-50/53-48/20/22
Safety Statements  36/37-60-61-36/37/39-26
RIDADR  3077
WGK Germany  2
RTECS  SZ3500000
9
Autoignition Temperature 425 °C
TSCA  Yes
HS Code  29310095
Toxicity LD50 orally in Rabbit: 700 mg/kg LD50 dermal Rabbit > 4000 mg/kg
NFPA 704
1
2 0

Triphenylphosphine price More Price(29)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) T84409 Triphenylphosphine ReagentPlus?, 99% 603-35-0 1G ₹2200 2022-06-14 Buy
Sigma-Aldrich(India) T84409 Triphenylphosphine ReagentPlus?, 99% 603-35-0 25G ₹2490 2022-06-14 Buy
Sigma-Aldrich(India) T84409 Triphenylphosphine ReagentPlus?, 99% 603-35-0 100G ₹3130 2022-06-14 Buy
Sigma-Aldrich(India) T84409 Triphenylphosphine ReagentPlus?, 99% 603-35-0 500G ₹13834.35 2022-06-14 Buy
Sigma-Aldrich(India) T84409 Triphenylphosphine ReagentPlus?, 99% 603-35-0 1KG ₹14029.2 2022-06-14 Buy
Product number Packaging Price Buy
T84409 1G ₹2200 Buy
T84409 25G ₹2490 Buy
T84409 100G ₹3130 Buy
T84409 500G ₹13834.35 Buy
T84409 1KG ₹14029.2 Buy

Triphenylphosphine Chemical Properties,Uses,Production

Chemical Properties

Triphenylphosphine is a white to light tan flaked solid. Insoluble inwater; slightly soluble in alcohol; soluble in benzene, acetone, carbon tetrachloride. Combustible.

Uses

Triphenylphosphine is used in the synthesis of Chlorambucil with cytotoxicity in breast and pancreatic cancers. Also used in the preparation of α-Tocopherol analogues for monitoring antioxidant status.

Production Methods

Triphenylphosphine is one of the most widely used phosphorus-containing reagents in organic synthesis for many types of transformations such as the Mitsunobu, the Wittig, and the Staudinger reaction. Triphenylphosphine can be prepared in the laboratory by treatment of phosphorus trichloride with phenylmagnesium bromide or phenyllithium. The industrial synthesis involves the reaction between phosphorus trichloride, chlorobenzene, and sodium.
PCl3 + 3 PhCl + 6 Na → PPh3 + 6 NaCl

General Description

Rhodium and triphenylphosphine catalyst system has been used for the hydroformylation of soybean, safflower and linseed oils and their methyl esters. Polymer supported triphenylphosphine has been reported to efficiently catalyze the γ-addition of pronucleophiles to alkynoate. Triphenylphosphine reacts with hydrated ruthenium trichloride in methanol to afford [RuCl2(PPh3)4], [RuCl2(PPh3)3] and [RuCl3(PPh3)2CH3OH]. It participates in the Heck reaction of 4-bromoanisole and ethyl acrylate in ionic liquids.

Reactivity Profile

Triphenylphosphine reacts vigorously with oxidizing materials. .

Health Hazard

ACUTE/CHRONIC HAZARDS: Toxic; when heated to decomposition, emits highly toxic fumes of phosphine and POx.

Safety Profile

Moderately toxic by ingestion. Mildly toxic by inhalation. A skin and eye irritant. Combustible when exposed to heat or flame. Slight explosion hazard in the form of vapor when exposed to flame. Can react vigorously with oxidizing materials. To fight fire, use dry chemical, fog, CO2. When heated to decomposition it emits highly toxic fumes of phosphne and POx. See also PHOSPHINE and PHENOL.

Purification Methods

It crystallises from hexane, MeOH, diethyl ether, CH2Cl2/hexane or 95% EtOH. Dry it at 65o/<1mm over CaSO4 or P2O5. Chromatograph it through alumina using (4:1) *benzene/CHCl3 as eluent. [Blau & Espenson et al. J Am Chem Soc 108 1962 1986, Buchanan et al. J Am Chem Soc 108 1537 1986, Randolph & Wrighton J Am Chem Soc 108 3366 1986, Asali et al. J Am Chem Soc 109 5386 1987.] It has also been crystallised twice from pet ether and 5 times from Et2O/EtOH to give m 80.5o. Alternatively, dissolve it in conc HCl, and upon dilution with H2O it separates because it is weakly basic, it is then crystallised from EtOH/Et2O. It recrystallises unchanged from AcOH. [Forward et al. J Chem Soc Suppl. p121 1949, Muller et al. J Am Chem Soc 78 3557 1956.] 3Ph3P.4HCl crystallises out when HCl gas is bubbled through an Et2O solution, it has m 70-73o, but recrystallises very slowly and is deliquescent. The hydriodide, made by adding Ph3P to hydriodic acid, is not hygroscopic and decomposes at ~100o. The chlorate (1:1) salt has m 165-167o, but decomposes slowly at 100o. All salts hydrolyse in H2O to give Ph3P [IR, UV: Sheldon & Tyree J Am Chem Soc 80 2117 1958, pK: Henderson & Streuli J Am Chem Soc 82 5791 1960, Kosolapoff, Organophosphorus Compounds, Wiley 1950]. [Beilstein 16 IV 951.] § Available commercially on a polystyrene or polyethyleneglycol support.

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