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A12931 1,3-Bis(diphenylphosphino)propane, 97%

CAS Number
6737-42-4
Synonyms
Dppp

Stock No. Size Price ($) Quantity Availability
A12931-06 5g 58.00
A12931-14 25g 193.00
A12931-22 100g 635.00
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1,3-Bis(diphenylphosphino)propane, 97%

MDL
MFCD00003050
EINECS
229-791-2

Chemical Properties

Formula
C27H26P2
Formula Weight
412.46
Melting point
58-63°
Storage & Sensitivity
Air Sensitive. Store under Argon. Ambient temperatures.
Solubility
Insoluble in water.

Applications

1,3-Bis(diphenylphosphino)propane is used as a bidentate ligand in coordination chemistry and form complex dichloro(1,3-bis(diphenylphosphino)propane)nickel by reacting with nickel(II) chloride. This complex is used as a catalyst for Kumada coupling reaction. It also acts as a ligand for palladium(II) catalysts which is useful for the co-polymerization of carbon monoxide and ethylene to get polyketones. Further, it is employed in palladium-catalyzed arylation under Heck reaction and Suzuki reaction. In addition to this, it serves as a catalyst for Negishi coupling and Sonogashira coupling reactions.

Notes

Air sensitive. Incompatible with strong oxidizing agents.

Literature References

Chelating phosphorus ligand which forms a 1:1 complex with NiCl2, which is an efficient catalyst for the coupling of Grignard reagents with aryl, vinylic or heterocyclic halides: Bull. Chem. Soc. Jpn., 49, 1958 (1976); Tetrahedron, 38, 3347 (1982); Synthesis, 386 (1988).

Successful Suzuki coupling of arylboronic acids with aryl chlorides bearing electron-withdrawing groups was achieved in the presence of Palladium(II)­ acetate, 10516, and dppp: Tetrahedron Lett., 38, 5575 (1997).

Qi, X.; Jiang, L. B.; Li, H. P.; Wu, X. F. A A Convenient Palladium-Catalyzed Carbonylative Suzuki Coupling of Aryl Halides with Formic Acid as the Carbon Monoxide Source. Chem. Eur. J. 2015, 21 (49), 17650-17656.

Tsubomura, T.; Kimura, K.; Nishikawa, M.; Tsukuda, T. Structures and photophysical properties of copper(I) complexes bearing diphenylphenanthroline and bis(diphenylphosphino)alkane: the effect of phenyl groups on the phenanthroline ligand. Dalton Trans. 2015, 44 (16), 7554-7562.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
2821785
Harmonized Tariff Code
2931.39
TSCA
Yes

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