Binap, (A+-)-
RAC-BINAP · (R)-BINAP · (R)-(+)-BINAP · (+)-BINAP · RAC-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL · RACEMIC-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL · (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene · (+/-)-BINAP
Identifiers & Physical Properties
| CAS No. | 76189-55-4 |
|---|---|
| Molecular formula | C44H32P2 |
| Average molar mass | 622.7 g/mol |
| Monoisotopic mass | 622.19792428 g/mol |
| SMILES | c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1 |
| InChIKey | MUALRAIOVNYAIW-UHFFFAOYSA-N |
| PubChem CID | 634876 |
| ChEMBL | CHEMBL1275990 |
| EC No. | 616-304-7 |
| DTXSID | DTXSID40913327 |
Chemical & Physical Properties
| XLogP | 11.4 |
|---|---|
| Topological polar surface area | 0 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 0 |
| Rotatable bonds | 7 |
| Heavy atoms | 46 |
| Formal charge | 0 |
| Complexity | 797 |
| Melting point | 283-286 °C(lit.) |
| alpha | 240 º (c=0.3, toluene) |
| Boiling point | 724.3±55.0 °C(Predicted) |
| Refractive index | 235 ° (C=0.3, Toluene) |
| Storage conditions | Inert atmosphere,Room Temperature |
| Solubility | Benzene (Slightly), Chloroform (Slightly)insoluble |
| Physical state | Powder |
| Color | White to cream-white |
| optical activity | [α]20/D +222°, c = 0.5% in benzene |
| Sensitivity | Air Sensitive |
| Merck | 14,1223 |
| BRN | 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 | 76189-55-4(CAS DataBase Reference) |
| FDA UNII | 4F1X2F8NA3 |
| UNSPSC Code | 12352005 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Hazard symbols | Xi,Xn |
| Risk statements (R) | 36/37/38-20/21/22 |
| Safety statements (S) | 22-24/25-37/39-26-36 |
| Water hazard class (WGK) | 3 |
| F | 8-10-23 |
| TSCA inventory status | No |
| Customs code | 29319090 |
| Storage class | 11 - Combustible Solids |
Safety & Regulations
| GHS classification | WarningH315 (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. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (77.8%)Skin Irrit. 2 (96%) |
| F | 8-10-23 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | No |
| Customs code | 29319090 |
| Risk statements (R) | 36/37/38-20/21/22 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi,Xn |
| Safety statements (S) | 22-24/25-37/39-26-36 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a |
Applications & Uses
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.
Uses
Chiral 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.