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
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
| Publication Number | Title | Priority Date |
|---|---|---|
| CN-114085213-A | Preparation method of ARV-471 | 2022-01-20 |
| CN-114029092-A | Synthesis method of metal catalyst | 2021-12-29 |
| CN-114163465-A | Synthesis method of alkenyl borate compound | 2021-12-24 |
| CN-113979999-A | Compound for targeted ubiquitination degradation of BCR-ABL kinase and preparation method, composition and application thereof | 2021-12-23 |
| CN-114014864-A | Preparation process of traasiril compound | 2021-12-21 |
| CN-114181077-A | Method for synthesizing tranexamic acid | 2021-12-20 |
| 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 |
