Basic information
- Standard SMILES
c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1- InChIKey
MUALRAIOVNYAIW-UHFFFAOYSA-N- Molecular formula
- C44H32P2
- Average molar mass
- 622.7 g/mol
- Monoisotopic mass
- 622.19792428
Overview
See other relationships...
Names & identifiers
- Preferred name
- Binap, (A+-)-
- IUPAC
- [1-(2-diphenylphosphanylnaphthalen-1-yl)naphthalen-2-yl]-diphenylphosphane
- English name
- (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
- Molecular formula
- C44H32P2
- Molecular weight
- 622.69
Names & synonyms
Show more names
Database identifiers
- CAS
76189-55-4、76189-56-5、98327-87-8- PubChem CID
- 634876
- DTXSID
DTXSID40913327- ChEMBL
CHEMBL1275990- UNII
- 4F1X2F8NA3、970O8508MB、OX12238KWH
- EC Number
- 616-304-7、619-338-0、918-620-3
- Nikkaji
- J1.058.033A、J1.058.045E、J181.354D、J181.355B、J461.407K
Properties
Computed structural properties
- XLogP
- 11.4
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 7
- Heavy atoms
- 46
- Formal charge
- 0
- Complexity
- 797
Physicochemical properties
- Melting point
- 283 · 283-286 °C(lit.)
- alpha
- 240 · 240 º (c=0.3, toluene)
- Boiling point
- 724.3 · 724.3±55.0 °C(Predicted)
- refractive index
- 235 ° · 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
- 20 · [α]20/D +222°, c = 0.5% in benzene
- Water Solubility
- insoluble
- Sensitive
- Air Sensitive
- Merck
- 14 · 14,1223
- BRN
- 4914063 · 4914063
- InChIKey
- MUALRAIOVNYAIW-UHFFFAOYSA-N
- SMILES
- P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC2=CC=CC=C2C=1C1C2=CC=CC=C2C=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1
- CAS DataBase Reference
- 76189 · 76189-55-4(CAS DataBase Reference)
- FDA UNII
- 4 F1X2F8NA3 · 4F1X2F8NA3
- UNSPSC Code
- 12352005 · 12352005
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xi,Xn
- Risk Statements
- 36 · 36/37/38-20/21/22
- Safety Statements
- 22 · 22-24/25-37/39-26-36
- WGK Germany
- 3 · 3
- F
- 8 · 8-10-23
- TSCA
- No
- HS Code
- 29319090 · 29319090
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (96%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 25 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
This chemical does not meet GHS hazard criteria for 11.1% (1 of 9) of reports.
Warning
Hazard information
Hazard Classes and Categories
Skin Irrit. 2 (77.8%)
Skin Irrit. 2 (96%)
Safety data
- F
- 8-10-23
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- No
- hs_code
- 29319090
- risk_code
- 36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn
- safety_code
- 22-24/25-37/39-26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Applications
Uses(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl is a useful ligand for transition metal catalyzed asymmetric reactions, including hydrogenation and disilylation. (R)-(+)-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.
UsesChiral ligand for metal mediated asymmetric catalysis.
General Description(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene is an axially dissymmetric bis(triaryl)phosphine ligand for asymmetric reactions.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Related reactions
Linked notes
Loading…