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A11419 1,2-Bis(diphenylphosphino)ethane, 97+%

CAS Number
1663-45-2
Synonyms
Diphos
Dppe

Stock No. Size Price ($) Quantity Availability
A11419-06 5g 37.80
A11419-14 25g 110.00
A11419-22 100g 402.00
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1,2-Bis(diphenylphosphino)ethane, 97+%

MDL
MFCD00003047
EINECS
216-769-2

Chemical Properties

Formula
C26H24P2
Formula Weight
398.42
Melting point
138-143°
Storage & Sensitivity
Air Sensitive. Store under Argon. Ambient temperatures.
Solubility
Soluble in acetone, methanol and alcoholic hydrochloric acid.

Applications

1,2-Bis(diphenylphosphino)ethane is a bidendate ligand used in coordination chemistry to prepare metal complexes. It is involved in the metal-catalyzed allylic alkylation and decarboxylation of allylic esters. It is also used in 1,3-diene synthesis. Further, it is used in cycloaddition reactions and carbonylation reactions. In addition to this, it is used to prepare bis(dicyclohexylphosphino)ethane by hydrogenation.

Notes

Air sensitive. Incompatible with strong oxidizing agents.

Literature References

Chelating phosphorus ligand.

The complex with NiCl2 catalyzes the coupling of haloaromatic compounds with Grignard reagents: J. Org. Chem., 49, 478 (1984).

The catalyst prepared in situ with Sodium tetrachloropalladate(II)­ hydrate, 11886, catalyzes the carbonylation of allylic halides at atmospheric pressure: Chem. Lett., 1873 (1989):

Useful replacement for Triphenyl­phosphine, L02502, in the Staudinger and Mitsunobu reactions, with the advantage of easier separation of the by-product bis(phosphine oxide) due to its higher polarity compared with triphenylphosphine oxide: Tetrahedron Lett., 39, 7787 (1998). Has also been used as an alternative to PPh3 for the halodehydroxylation of alcohols, e.g. in combination with Hexachloroethane, L14297, alkyl chlorides are formed; the phosphine oxide by-product can readily be separated by filtration: Tetrahedron Lett., 42, 2459 (2001).

Afonin, M. Y.; Smolentsev, A. I.; Konchenko, S. N.; Petrov, P. A. Cyanato- and thiocyanato-substituted triangular clusters of molybdenum, [Mo3S4(dppe)3X3]+ (X = NCO-, NCS-; dppe = 1,2-bis(diphenylphosphino)ethane). J. Coord. Chem. 2015, 68 (3), 422-431.

Bloomfield, A. J.; Sheehan, S. W.; Collom, S. L.; Crabtree, R. H.; Anastas, P. T. A heterogeneous water oxidation catalyst from dicobalt octacarbonyl and 1,2-bis(diphenylphosphino)ethane. New J. Chem. 2014, 38 (4), 1540-1545.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335-H500

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. May form combustible dust concentrations in air

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
761261
Harmonized Tariff Code
2931.39
TSCA
Yes

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