rac-BINAP

[2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl]

Other Names:

(±)-BINAP

2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene

(±)-2,2'-Bis(diphenylphosphino)-1,1'-

binaphthalene

General Information:

Structure:

CAS Number: 98327-87-8

Molecular Weight: 622.69 g/mol

Appearance: Colorless solid

Melting Point: 283-286 C

rac-BINAP is a racemic mixture of (R)-BINAP and (S)-BINAP. rac-BINAP is commonly used as a bidentate phosphine ligand in palladium catalyzed cross-coupling reactions.

Common Uses:

Ligand in Buchwald reactions

Procedure excerpt:

. . . the chloride (25 g, 168 mmol), the amine (40 g, 168 mmol), Pd(OAc)2 (1.5 g, 6.72 mmol), (+-) BINAP (4.18 g, 6.72 mmol), and Cs2CO3 (76.7 g, 235.2 mmol) in toluene (800 mL) . . .

[full procedure]

References:

1) Patent Reference: WO2010016005, page 91, (11.3 MB)

2) Wikipedia: BINAP (link)

3) www.sigmaaldrich.com: rac-BINAP (link)

4) www.alfa.com: H26226 (±)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 98% (link)