(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

Synonym(s):(R)-(+)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine);(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene;(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl;(R)-(+)-BINAP

CAS NO.：76189-55-4
Empirical Formula: C44H32P2
Molecular Weight: 622.69
MDL number: MFCD00010805
EINECS: 616-304-7
SAFETY DATA SHEET (SDS)
Update Date: 2024-07-26 07:33:58

(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Structural

What is (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl?

Chemical properties

White to light yellow crystal powde, insoluble in water.

The Uses of (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

Chiral ligand for metal mediated asymmetric catalysis.

The Uses of (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

Useful ligand for transition metal catalyzed asymmetric reactions, including hydrogenation and disilylation. 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl and its rhodium and ruthenium derivatives are highly selective homogeneous catalysts used for the reduction of aryl ketones, β-keto esters, and α-amino ketones. They have also been used for asymmetric hydrogenation and hydroformylation of olefins, asymmetric Heck reactions, and asymmetric isomerizations of allyls.
Complex with Ag(I) used to catalyze an asymmetric aldol reaction between alkenyl trichloroacetates and aldehydes. Also used with Ag(I) to catalyze an enantioselective hetero-Diels-Alder reaction of azo compounds.

General Description

(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene is an axially dissymmetric bis(triaryl)phosphine ligand for asymmetric reactions.

Properties of (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

Melting point:	283-286 °C(lit.)
Boiling point:	724.3±55.0 °C(Predicted)
alpha	240 º (c=0.3, toluene)
refractive index	235 ° (C=0.3, Toluene)
storage temp.	Inert atmosphere,Room Temperature
solubility	Benzene (Slightly), Chloroform (Slightly)
form	Powder
color	White to cream-white
optical activity	[α]20/D +222°, c = 0.5% in benzene
Water Solubility	insoluble
Sensitive	Air Sensitive
Merck	14,1223
BRN	4914063
CAS DataBase Reference	76189-55-4(CAS DataBase Reference)

Safety information for (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up.