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98327-87-8 - (±)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 98% - (+/-)-BINAP - (+/-)-(1,1'-Binaphthalene-2,2'-diyl)bis(diphenylphosphine) - H26226 - Alfa Aesar

H26226 (±)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 98%

CAS Number
98327-87-8
Synonyms
(+/-)-BINAP
(+/-)-(1,1'-Binaphthalene-2,2'-diyl)bis(diphenylphosphine)

Size Price ($) Quantity Availability
5g 103.50
25g 294.30
100g 638.10
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(±)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 98%

MDL
MFCD00010805
EINECS
None

Chemical Properties

Formula
C44H32P2
Formula Weight
622.69
Melting point
281-285°
Sensitivity
Air Sensitive
Solubility
Soluble in tetrahydrofuran, benzene and dichloromethane. Slightly soluble in ether, methanol and ethanol. Insoluble in water.

Applications

(^+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl plays an essential role in the organic synthesis of enantioselective transformations catalyzed by the complexes of ruthenium, rhodium and palladium. It is also employed in palladium-catalyzed arylamine coupling in the preparation of demethylthiocholchines. It is used with Cu(II) to catalyze the addition of arylsulfonamides to styrenes and olefins.

Notes

Air sensitive. Keep container tightly closed in a dry and well-ventilated place.

Literature References

Hatano, B.; Hashimoto, K.; Katagiri, H.; Kijima, T.; Murakami, S.; Matsuba, S.; Kusakari, M. Enantioresolution of 2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Oxide Using Inclusion Complex with Chiral 2,2'-Dihydroxy-1,1'-binaphtyl. J. Org. Chem. 2012, 77 (7), 3595-3597.

Deng, C.; Ou, G.; She, J.; Yuan, Y. Biphasic asymmetric hydroformylation and hydrogenation by water-soluble rhodium and ruthenium complexes of sulfonated (R)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl in ionic liquids. J. Mol. Catal. A: Chem. 2007, 270 (1-2), 76-82.

Atesin, A. C.; Zhang, J.; Vaidya, T.; Brennessel, W. W.; Frontier, A. J.; Eisenberg, R. Synthesis, Characterization, and Catalytic Properties of New Electrophilic Iridium(III) Complexes Containing the (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Ligand. Inorg. Chem. 2010, 49 (9), 4331-4342.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

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

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,1223
Beilstein
5321443
Harmonized Tariff Code
2931.90
TSCA
No

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