Basic information
- Standard SMILES
c1ccc(-c2ccccc2P(C2CCCCC2)C2CCCCC2)cc1- InChIKey
LCSNDSFWVKMJCT-UHFFFAOYSA-N- Molecular formula
- C24H31P
- Average molar mass
- 350.5 g/mol
- Monoisotopic mass
- 350.21633799
Names & identifiers
- Preferred name
- 2-(Dicyclohexylphosphino)biphenyl
- IUPAC
- dicyclohexyl-(2-phenylphenyl)phosphane
- English name
- 2-(Dicyclohexylphosphino)biphenyl
- Molecular formula
- C24H31P
- Molecular weight
- 350.48
Names & synonyms
Show more names
Database identifiers
- CAS
247940-06-3- PubChem CID
- 2734216
- DTXSID
DTXSID60370170- EC Number
- 480-030-2、607-439-2
- Nikkaji
- J1.200.103G、J3.476.307K
Properties
Computed structural properties
- XLogP
- 6.7
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 4
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 356
Physicochemical properties
- Melting point
- 102 · 102-106 °C(lit.)
- Boiling point
- 499.5 · 499.5±24.0 °C(Predicted)
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2-8°C
- solubility
- soluble in Toluene
- form
- crystal
- color
- white
- Sensitive
- Air Sensitive
- BRN
- 8440533 · 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 · 247940-06-3(CAS DataBase Reference)
- UNSPSC Code
- 12352002 · 12352002
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 413 · H413
- Precautionary statements
- 261 · P261-P280-P305+P351+P338-P304+P340-P405-P501A
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xn
- Risk Statements
- 36 · 36/37/38-22
- Safety Statements
- 36 · 36/37/39-26
- WGK Germany
- 3 · 3
- F
- 10 · 10-13-23
- TSCA
- No
- HazardClass
- AIR SENSITIVE
- HS Code
- 29310099 · 29310099
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 · Aquatic Chronic 4
- REACH Registrations
- Inactive
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (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 exposure; Respiratory 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.
Hazard information
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%)
Regulatory information
Safety data
- F
- 10-13-23
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- No
- hs_code
- 29310099
- risk_code
- 36/37/38-22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 36/37/39-26
- hazard_class
- AIR SENSITIVE
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H413
- REACH Registrations
- Inactive
- Hazard Classifications
- Aquatic Chronic 4
- Precautionary statements
- P261-P280-P305+P351+P338-P304+P340-P405-P501A
Chemistry & industry
Applications
Description2-(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.
UsesLigand employed in an extremely general method for the Pd-catalyzed synthesis of aromaticamines using aryl chlorides, bromides and triflates.
Usessuzuki reaction
Uses2-(Dicyclohexylphosphino)biphenyl is used as a catalyst for Suzuki coupling reactions.
General DescriptionCyJohnPhos [(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.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Related reactions
Linked notes
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