2-(Dicyclohexylphosphino)biphenyl

HCID 2734216CAS 247940-06-3

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

2-(Dicyclohexylphosphino)biphenyl247940-06-3DTXSID603701702-[dicyclohexylphosphino]biphenylRefChem:84662DTXCID40321206480-030-2607-439-2CyJohnPhosCyclohexyl JohnPhosDicyclohexyl-(2-phenylphenyl)phosphane[1,1'-BIPHENYL]-2-YLDICYCLOHEXYLPHOSPHINE
Show more names
Cy-John-Phos2-(Dicyclo98% CyJohnPhosCyJohnPhos 97%CyJohnPhos CASCAS:247940-06-3
PHOSPHINE, [1,1'-BIPHENYL]-2-YLDICYCLOHEXYL-biphenyl-2-yldicyclohexylphosphine(2-Biphenylyl)dicyclohexylphosphineMFCD01862441(2-Biphenyl)dicyclohexylphosphineC24H31Po-(dicyclohexylphosphino)biphenyl{[1,1'-biphenyl]-2-yl}dicyclohexylphosphane

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

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

Safety & regulation

GHS classification

GHS Classification · 6 items

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

Regulatory InformationStatus: Active Update: 07-03-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/2550
Hazard Classes and Categories · 2 items

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

Regulatory InformationStatus: Active Update: 07-03-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/2550

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

Chemistry & industry

Applications · 5 items

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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

Related reactions

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