(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

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

CAS NO.：76189-56-5
Empirical Formula: C44H32P2
Molecular Weight: 622.69
MDL number: MFCD00010805
EINECS: 616-305-2
SAFETY DATA SHEET (SDS)
Update Date: 2024-10-29 11:48:30

(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Structural

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

Chemical properties

white to light yellow crystal powde

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

Chiral ligand for metal mediated asymmetric catalysis.

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

Reactant involved in:

Enantioselective and diastereoselective unpoled carbonyl allylation
Syntehsis of organophophine oxides as anittumor agents
SN2 halogenation of hydroxy groups
Synthesis of BINAP complexes
Studies of conformational flexibility of BINAP chelates

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

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.
Ligand used in a palladium-catalyzed, asymmetric, tandem Heck reaction-carbanion capture process leading to a synthesis of a tricyclic sesquiterpene. Also used in a ruthenium-catalyzed asymmetric hydrogenation of α,β-unsaturated acids.

Properties of (S)-(-)-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	Crystals or Crystalline Powder
color	White to light yellow
optical activity	[α]20/D -222, c = 0.5 in benzene
Sensitive	Air Sensitive
Merck	14,1223
BRN	5321444
CAS DataBase Reference	76189-56-5(CAS DataBase Reference)

Safety information for (S)-(-)-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.