2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene (BINAP)

Product Information

Molecular Formula:
C44H32P2
Molecular Weight:
622.67
Description
Ligand employed in a palladium-catalyzed arylamine coupling in the preparation of demethylthiocholchines. Used with Cu (II) to catalyze addition of arylsulfonamides to styrenes and olefins. Amination of terpyridines with Pd catalysis.
Synonyms
[1-(2-diphenylphosphino-1-naphthalenyl)-2-naphthalenyl]-diphenylphosphine; [1-(2-diphenylphosphanylnaphthalen-1-yl)naphthalen-2-yl]-diphenylphosphane
IUPAC Name
[1-(2-diphenylphosphanylnaphthalen-1-yl)naphthalen-2-yl]-diphenylphosphane
Canonical SMILES
C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8
InChI
InChI=1S/C44H32P2/c1-5-19-35(20-6-1)45(36-21-7-2-8-22-36)41-31-29-33-17-13-15-27-39(33)43(41)44-40-28-16-14-18-34(40)30-32-42(44)46(37-23-9-3-10-24-37)38-25-11-4-12-26-38/h1-32H
InChI Key
MUALRAIOVNYAIW-UHFFFAOYSA-N
Boiling Point
724.3 °C at 760 mmHg
Melting Point
283-286 °C (lit.)
Flash Point
Not applicable
Purity
97 %
Storage
Keep in dark place, Inert atmosphere, Room temperature
LogP
10.92580

Safety Information

Precautionary Statement
P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501
Signal Word
Warning

Computed Properties

XLogP3
11.4
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
0
Rotatable Bond Count
7
Exact Mass
622.19792502 g/mol
Monoisotopic Mass
622.19792502 g/mol
Topological Polar Surface Area
0Ų
Heavy Atom Count
46
Formal Charge
0
Complexity
797
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes

Patents

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CN-114085213-A Preparation method of ARV-471 2022-01-20
CN-114029092-A Synthesis method of metal catalyst 2021-12-29
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CN-114014850-A Prudelamine intermediate, synthesis method thereof and method for synthesizing prasulamine from intermediate 2021-12-17
CN-114149447-A Preparation method of 5-isosorbide mononitrate 2021-12-15
JP-2022031355-A Pest control method 2021-12-15
CN-114149438-A Quinoxaline and diazole derivatives based on 9, 10-dimethyl-9, 10-ethylene anthracene and preparation method thereof 2021-12-03

Literatures

PMID Publication Date Title Journal
22807859 2012-07-01 rac-2,2'-Bis(diphenyl-phosphan-yl)-1,1'-binaphth-yl: a racemic diphosphine ligand Acta crystallographica. Section E, Structure reports online
22402867 2012-04-21 A new cascade reaction: concurrent construction of six and five membered rings leading to novel fused quinazolinones Organic & biomolecular chemistry
22589832 2012-04-01 Di-μ-iodido-bis-{[(R)-(+)-2,2'-bis-(di-phenyl-phosphan-yl)-1,1'-binaphthyl-κ(2)P,P']copper(I)} 0.67-hydrate Acta crystallographica. Section E, Structure reports online
22412414 2012-03-01 (+)-Chlorido[(1,2,3,4-η;κP)-2'-diphenyl-phosphanyl-2-diphenyl-phosphoryl-1,1'-binaphth-yl]rhodium(I) methanol monosolvate Acta crystallographica. Section E, Structure reports online
21639096 2011-07-13 A general copper-BINAP-catalyzed asymmetric propargylation of ketones with propargyl boronates Journal of the American Chemical Society
21314107 2011-03-18 Synthesis of α-carbolines via Pd-catalyzed amidation and Vilsmeier-Haack reaction of 3-acetyl-2-chloroindoles Organic letters
21344669 2011-03-01 Rhodium-catalyzed 1,4-addition of lithium 2-furyltriolborates to unsaturated ketones and esters for enantioselective synthesis of γ-oxo-carboxylic acids by oxidation of the furyl ring with ozone Chemistry, an Asian journal
21080707 2010-12-17 Highly enantioselective alkynylation of trifluoropyruvate with alkynylsilanes catalyzed by the BINAP-Pd complex: access to α-trifluoromethyl-substituted tertiary alcohols Organic letters
21038042 2010-12-14 Highly enantioselective Cu(I)-Tol-BINAP-catalyzed asymmetric conjugate addition of Grignard reagents to α,β-unsaturated esters Chemical communications (Cambridge, England)
20832917 2010-11-01 The preparation of bi-functional organophosphine oxides as potential antitumor agents European journal of medicinal chemistry
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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