2-(Dicyclohexylphosphino)biphenyl
Cy-John-Phos · CYCLOHEXYL JOHNPHOS · (2-biphenyl)dicyclohexylphosphine · dicyclohexyl-(2-phenylphenyl)phosphane · biphenyl-2-yldicyclohexylphosphine · 2-(Dicyclo · 98% CyJohnPhos · CyJohnPhos 97%
Identifiers & Physical Properties
| CAS No. | 247940-06-3 |
|---|---|
| Molecular formula | C24H31P |
| Average molar mass | 350.5 g/mol |
| Monoisotopic mass | 350.21633799 g/mol |
| SMILES | c1ccc(-c2ccccc2P(C2CCCCC2)C2CCCCC2)cc1 |
| InChIKey | LCSNDSFWVKMJCT-UHFFFAOYSA-N |
| PubChem CID | 2734216 |
| EC No. | 480-030-2 |
| DTXSID | DTXSID60370170 |
Chemical & Physical Properties
| XLogP | 6.7 |
|---|---|
| Topological polar surface area | 0 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 0 |
| Rotatable bonds | 4 |
| Heavy atoms | 25 |
| Formal charge | 0 |
| Complexity | 356 |
| Melting point | 102-106 °C(lit.) |
| Boiling point | 499.5±24.0 °C(Predicted) |
| Storage conditions | under inert gas (nitrogen or Argon) at 2-8°C |
| Solubility | soluble in Toluene |
| Physical state | crystal |
| Color | white |
| Sensitivity | Air Sensitive |
| BRN | 8440533 |
| InChI | InChI=1S/C24H31P/c1-4-12-20(13-5-1)23-18-10-11-19-24(23)25(21-14-6-2-7-15-21)22-16-8-3-9-17-22/h1,4-5,10-13,18-19,21-22H,2-3,6-9,14-17H2 |
| InChIKey | LCSNDSFWVKMJCT-UHFFFAOYSA-N |
| SMILES | P(C1=CC=CC=C1C1=CC=CC=C1)(C1CCCCC1)C1CCCCC1 |
| CAS DataBase Reference | 247940-06-3(CAS DataBase Reference) |
| UNSPSC Code | 12352002 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H413 |
| GHS precautionary statements | P261-P280-P305+P351+P338-P304+P340-P405-P501A |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Hazard symbols | Xn |
| Risk statements (R) | 36/37/38-22 |
| Safety statements (S) | 36/37/39-26 |
| Water hazard class (WGK) | 3 |
| F | 10-13-23 |
| TSCA inventory status | No |
| Hazard class | AIR SENSITIVEAquatic Chronic 4 |
| Customs code | 29310099 |
| Storage class | 11 - Combustible Solids |
| REACH registrations | Inactive |
Safety & Regulations
| GHS classification | WarningH315 (13.3%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (13.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (13.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]H413 (88.9%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]P261, P264, P264+P265, P271, P273, 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 45 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatory information | Status: Active Update: 07-03-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/2550 |
| Hazard Classes and Categories | Skin Irrit. 2 (13.3%)Eye Irrit. 2 (13.3%)STOT SE 3 (13.3%)Aquatic Chronic 4 (88.9%)Skin Irrit. 2 (100%)Eye Irrit. 2A (100%)STOT SE 3 (100%)Aquatic Chronic 4 (100%) |
| F | 10-13-23 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | No |
| Customs code | 29310099 |
| Risk statements (R) | 36/37/38-22 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xn |
| Safety statements (S) | 36/37/39-26 |
| Hazard class | AIR SENSITIVEAquatic Chronic 4 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H413 |
| REACH registrations | Inactive |
| GHS precautionary statements | P261-P280-P305+P351+P338-P304+P340-P405-P501A |
Applications & Uses
Description
2-(Dicyclohexylphosphino)biphenyl is a ligand for the amination of triflates and aryl halides. Optimal ligand for a novel amination reaction (Buchwald reaction)(2) 2-(Dicyclohexylphosphino)biphenyl, a synthetic chemical compound, has found diverse applications in scientific research. Being a cyclic phosphonate derivative of cyclohexanol, this colourless, odourless, and tasteless solid holds a distinct appeal for laboratory use. In scientific research, 2-(Dicyclohexylphosphino)biphenyl has proven invaluable. It serves as an excellent model compound for delving into protein-ligand interactions, thus aiding in studying small molecule effects on protein folding. Moreover, researchers have utilized 2-(Dicyclohexylphosphino)biphenyl to gain insights into protein structures and unravel the mechanism of action behind various drugs. Additionally, the compound has been a vital tool in assessing how environmental factors influence protein structure and function. The interaction between 2-(Dicyclohexylphosphino)biphenyl and proteins primarily occurs through hydrogen bonding and hydrophobic interactions, resulting in high-affinity and specific protein binding.
Uses
Ligand employed in an extremely general method for the Pd-catalyzed synthesis of aromaticamines using aryl chlorides, bromides and triflates.
Uses
suzuki reaction
Uses
2-(Dicyclohexylphosphino)biphenyl is used as a catalyst for Suzuki coupling reactions.
General Description
CyJohnPhos [(2-Biphenyl)dicyclohexylphosphine] is an air-stable, bulky and electron-rich monodentate biarylphosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.