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Merck

T84409

Triphenylphosphine

99%, ReagentPlus®

Triphenylphosphine

Synonym(s):

Phosphorustriphenyl

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CZK 635.80

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CZK 5,210.00

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CZK 6,980.00

CZK 635.80

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About This Item

Linear Formula:
(C6H5)3P
CAS Number:
Molecular Weight:
262.29
NACRES:
NA.21
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
210-036-0
MDL number:
Beilstein/REAXYS Number:
610776

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Product Name

Triphenylphosphine, ReagentPlus®, 99%

InChI

1S/C18H15P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H

InChI key

RIOQSEWOXXDEQQ-UHFFFAOYSA-N

SMILES string

c1ccc(cc1)P(c2ccccc2)c3ccccc3

vapor density

9 (vs air)

vapor pressure

5 mmHg ( 20 °C)

product line

ReagentPlus®

assay

99%

feature

achiral

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand
reaction type: Cross Couplings

parameter

air stable

bp

377 °C (lit.)

mp

79-81 °C (lit.)

functional group

phosphine

Quality Level

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1 of 4

This Item
930928.082708.00551
reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Hiyama Coupling, reaction type: Sonogashira Coupling, reaction type: Suzuki-Miyaura Coupling, reaction type: Heck Reaction, reaction type: Stille Coupling, reaction type: Negishi Coupling, reagent type: ligand
reaction type: Cross Couplings

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: ligand

reaction suitability

-

reaction suitability

-

assay

99%

assay

≥95.0% (GC)

assay

≥99.0% (GC)

assay

≥97.0% (GC)

functional group

phosphine

functional group

phosphine

functional group

-

functional group

-

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

bp

377 °C (lit.)

bp

377 °C (lit.)

bp

377 °C/1013 hPa

bp

360 °C/1013 hPa (decomposes)

mp

79-81 °C (lit.)

mp

77-84 °C, 79-81 °C (lit.)

mp

78.5-81.5 °C

mp

-

Application

Triphenylphosphine was used in the synthesis of mono-6-amino-deoxy-6-cyclodextrin.[1] It was also employed as catalyst during the synthesis of C-aryl furanosides.[2]

General description

Rhodium and triphenylphosphine catalyst system has been used for the hydroformylation of soybean, safflower and linseed oils and their methyl esters.[3] Polymer supported triphenylphosphine has been reported to efficiently catalyze the γ-addition of pronucleophiles to alkynoate.[4] Triphenylphosphine reacts with hydrated ruthenium trichloride in methanol to afford [RuCl2(PPh3)4], [RuCl2(PPh3)3] and [RuCl3(PPh3)2CH3OH].[2] It participates in the Heck reaction of 4-bromoanisole and ethyl acrylate in ionic liquids.[5]

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Sens. 1B - STOT RE 1 Inhalation

target_organs

Central nervous system,Peripheral nervous system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 2

flash_point_f

356.0 °F - closed cup

flash_point_c

180 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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Triphenylphosphine: a catalyst for the synthesis of C-aryl furanosides from furanosyl halides.
Nicolas L, et al.
Tetrahedron Letters, 55(4), 849-852 (2014)
Facile synthesis of mono-6-amino-6-deoxy-a-, ?-, ?-cyclodextrin hydrochlorides for molecular recognition, chiral separation and drug delivery.
Tang W and Ng S-C.
Nature Protocols, 3(4), 691-697 (2008)
Xi Kang et al.
Chemical science, 10(37), 8685-8693 (2019-12-06)
Structural transformations between isomers of nanoclusters provide a platform to tune their properties and understand the fundamental science due to their intimate structure-property correlation. Herein, we demonstrate a reversible transformation between the face-centered cubic (FCC) and icosahedral isomers of Pt1Ag28
Shuxin Wang et al.
Nature communications, 8(1), 848-848 (2017-10-12)
It has long been a challenge to dope metal nanoparticles with a specific number of heterometal atoms at specific positions. This becomes even more challenging if the heterometal belongs to the same group as the host metal because of the
Selective hydroformylation of polyunsaturated fats with a rhodium-triphenylphosphine catalyst.
Frankel EN and Thomas FL.
Journal of the American Oil Chemists' Society, 49(1), 10-14 (1972)

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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Reviews

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  1. 02139
    • Review 1
    • Votes 3
    5 out of 5 stars.

    High quality

    My reactions worked, high quality. Removing triphenylphosphine oxide was hard.

    Helpful?

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