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CAS RN: 603-35-0 | Product Number: T0519

Triphenylphosphine

Thumbnail of Triphenylphosphine
  • Chemical Structure of Triphenylphosphine
Chemical Structure of Triphenylphosphine
× Triphenylphosphine

Purity: >95.0%(T)
Synonyms:
  • TPP
Product Documents:
SDS | Specifications | C of A & Other Certificates | Analytical Charts

General Information | Specifications & Properties | Safety & Regulations | Applications & Literature

Explanatory notes for this page

25G
₹2,500.00
 ≥60  ≥100 
100G
₹3,000.00
 ≥80  ≥100 
500G
₹9,800.00
 17   ≥100 

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Product Number T0519
Purity / Analysis Method >95.0%(T)
Molecular Formula / Molecular Weight C__1__8H__1__5P = 262.29 
Physical State (20 deg.C) Solid
Storage Temperature Room Temperature (Recommended in a cool and dark place, <15°C)
CAS RN 603-35-0
Reaxys Registry Number 610776
PubChem Substance ID 87576446
SDBS (AIST Spectral DB) 2967
Merck Index (14) 9743
MDL Number

MFCD00003043
Specifications
Appearance White powder to lump
Purity(Iodometric Titration) min. 95.0 %
Melting point 80.0 to 82.0 °C
Solubility in Toluene very faint turbidity
NMR confirm to structure
Properties (reference)
Melting Point 81 °C
Boiling Point 260 °C/25 mmHg
Solubility in water Insoluble
Degree of solubility in water 0.3 mg/l   25 °C
Solubility (soluble in) Benzene, Chloroform, Toluene
Solubility (slightly sol. in) Alcohol
GHS
Pictogram Pictogram Pictogram
Signal Word Danger
Hazard Statements H302 : Harmful if swallowed.
H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
H372 : Causes damage to organs through prolonged or repeated exposure.
H373 : May cause damage to organs through prolonged or repeated exposure.
H317 : May cause an allergic skin reaction.
H335 : May cause respiratory irritation.
H413 : May cause long lasting harmful effects to aquatic life.
Precautionary Statements P501 : Dispose of contents/ container to an approved waste disposal plant.
P273 : Avoid release to the environment.
P272 : Contaminated work clothing should not be allowed out of the workplace.
P260 : Do not breathe dust/ fume/ gas/ mist/ vapors/ spray.
P270 : Do not eat, drink or smoke when using this product.
P271 : Use only outdoors or in a well-ventilated area.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ eye protection/ face protection.
P302 + P352 : IF ON SKIN: Wash with plenty of water.
P314 : Get medical advice/ attention if you feel unwell.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P362 + P364 : Take off contaminated clothing and wash it before reuse.
P333 + P313 : If skin irritation or rash occurs: Get medical advice/ attention.
P301 + P312 + P330 : IF SWALLOWED: Call a POISON CENTER/doctor if you feel unwell. Rinse mouth.
P304 + P340 + P312 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Call a POISON CENTER/doctor if you feel unwell.
P403 + P233 : Store in a well-ventilated place. Keep container tightly closed.
P405 : Store locked up.
Related Laws:
RTECS# SZ3500000
Transport Information:
Application
t-Butyldimethylsilylation of Alcohols using TBS Reagents

T0519

References

  • 1)A New Method for Silylation of Hydroxylic Compounds: Reaction of Phenols and Alcohols with Silanols Mediated by Diethyl Azodicarboxylate and Triphenylphosphine
  • 2)Protection for the Hydroxyl Group, Including 1,2- and 1,3-Diols
    • P. G. M. Wuts, in Greene’s Protective Groups in Organic Synthesis, 5th ed., ed. by P. G. M. Wuts, John Wiley & Sons, Inc., Hoboken, New Jersey, 2014, Chap. 2, 17.


Application
Protection and deprotection of PMP groups

T0519

Reference

  • Protection for the Hydroxyl Group, Including 1,2- and 1,3-Diols
    • P. G. M. Wuts, in Greene’s Protective Groups in Organic Synthesis, 5th ed., ed. by P. G. M. Wuts, John Wiley & Sons, Inc., Hoboken, New Jersey, 2014, Chap. 2, 17.


Application
Corey-Fuchs Alkyne Synthesis

Typical Procedure:
Carbon tetrabromide (34.67 g, 104.5 mmol) and anhydrous CH2Cl2 (175 mL) are added to a 500 mL round bottom flask equipped with a magnetic stir bar and septum under N2 atmosphere. The reaction flask is cooled to 0 ℃ with an ice bath for 10 min. Triphenylphosphine (54.84 g, 209.1 mmol) is added in portions over 5 min, and the dark red solution is stirred at 0 ℃ for 30 min. 3,4-Dimethoxybenzaldehyde (17.37 g, 104.5 mmol) is added and the mixture is stirred at 0 ℃ for 1 h. A 1 : 1 mixture of H2O : brine is added and the layers are separated. The aqueous layer is extracted with a 1 : 1 mixture of hexanes : CH2Cl2, and the combined organic layers are dried, filtered, and concentrated under reduced pressure. The crude material is chromatographed on SiO2 (0-15% EtOAc/hexanes) to afford the dibromide 1 (29.37 g, Y. 88%) as a yellow oil.
Then, 1 (4.41 g, 13.79 mmol, 1.0 equiv) and THF (45 mL) are added to a 250 mL round bottom flask equipped with a magnetic stir bar and septum, and the reaction flask is cooled to -78 ℃ under N2 atmosphere. 2.5M n-BuLi solution in hexane (11.6 mL) is added slowly via syringe and the reaction solution is stirred at -78 ℃ for 45 min and then at 0 ℃ for 45 min. The flask is recooled to -78 ℃, and freshly distilled methyl chloroformate (1.1 mL, 1.3 mmol, 1.0 equiv) is added slowly via syringe. The mixture is stirred at -78 ℃ for 10 min, then 0 ℃ for 1 h. Saturated aqueous NH4Cl solution is added, and the layers are separated. The aqueous layer is extracted with Et2O, and the combined organic layers are dried, filtered and concentrated under reduced pressure. The residue is chromatographed (SiO2, 2-20% EtOAc / hexanes) to afford the desired alkyne 2 (2.83 g, Y. 93%) as a white solid.

References


Application
Corey-Nicolaou Macrolactonization1)

Typical Procedure:
To a stirred solution of the hydroxy carboxylic acid 1 (125 mg, 0.422 mmol) in dry CH2Cl2 (15 mL) is added triphenylphosphine (125 mg, 0.48 mmol) followed by 2,2’-dipyridyl disulfide (105 mg, 0.48 mmol) and the mixture is stirred until TLC (ethyl acetate : hexane = 2 : 3) shows complete loss of starting material (usually 0.5 h – 2 h). The mixture is concentrated in vacuo and dissolved in dry toluene (150 mL). To the solution is added 0.006M AgBF4 solution in toluene (1.2 mL) and the mixture is heated under reflux for 12 h. The mixture is cooled and solvents removed in vacuo. The residue is purified by flash column chromatography (acetone : CH2Cl2 = 0.5 : 99.5) to afford the desired lactone 2 (95 mg, Y. 81%).

References


PubMed Literature


Documents

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