Binap, (A+-)-

HCID 634876CAS 76189-55-4

Basic information

Standard SMILES
c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1
InChIKey
MUALRAIOVNYAIW-UHFFFAOYSA-N
Molecular formula
C44H32P2
Average molar mass
622.7 g/mol
Monoisotopic mass
622.19792428

Overview

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Names & identifiers

Preferred name
Binap, (A+-)-
IUPAC
[1-(2-diphenylphosphanylnaphthalen-1-yl)naphthalen-2-yl]-diphenylphosphane
English name
(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
Molecular formula
C44H32P2
Molecular weight
622.69

Names & synonyms

2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYLrac-BINAP(1,1'-Binaphthalene)-2,2'-diylbis(diphenylphosphine)RAC-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL970O8508MBPhosphine, 1,1'-(1,1'-binaphthalene)-2,2'-diylbis(1,1-diphenyl-DTXSID40913327RefChem:1079872Binap, (A+-)-DTXCID70102004898327-87-876189-55-4
Show more names
(+)-BINAPRACEMIC-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene(+/-)-BINAP98% (R)-BINAPRACEMIC-BINAP
76189-56-5(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthylBINAP(S)-BINAP2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl(R)-BINAP(R)-(+)-BINAP

Database identifiers

CAS
76189-55-4、76189-56-5、98327-87-8
PubChem CID
634876
DTXSID
DTXSID40913327
ChEMBL
CHEMBL1275990
UNII
4F1X2F8NA3、970O8508MB、OX12238KWH
EC Number
616-304-7、619-338-0、918-620-3
Nikkaji
J1.058.033A、J1.058.045E、J181.354D、J181.355B、J461.407K

Properties

Computed structural properties

XLogP
11.4
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
7
Heavy atoms
46

Physicochemical properties

Melting point
283 · 283-286 °C(lit.)
alpha
240 · 240 º (c=0.3, toluene)
Boiling point
724.3 · 724.3±55.0 °C(Predicted)
refractive index
235 ° · 235 ° (C=0.3, Toluene)
storage temp.
Inert atmosphere,Room Temperature
solubility
Benzene (Slightly), Chloroform (Slightly)

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H315 (96%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, 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 25 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

This chemical does not meet GHS hazard criteria for 11.1% (1 of 9) of reports.

Warning

Hazard information

Hazard Classes and Categories · 2 items

Skin Irrit. 2 (77.8%)

Skin Irrit. 2 (96%)

Safety data

F
8-10-23
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
No
hs_code
29319090
risk_code
36/37/38-20/21/22

Chemistry & industry

Applications · 3 items

Uses(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl is a useful ligand for transition metal catalyzed asymmetric reactions, including hydrogenation and disilylation. (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl and its rhodium and ruthenium derivatives are highly selective homogeneous catalysts used for the reduction of aryl ketones, β-keto esters, and α-amino ketones. They have also been used for asymmetric hydrogenation and hydroformylation of olefins, asymmetric Heck reactions, and asymmetric isomerizations of allyls.Complex with Ag(I) used to catalyze an asymmetric aldol reaction between alkenyl trichloroacetates and aldehydes. Also used with Ag(I) to catalyze an enantioselective hetero-Diels-Alder reaction of azo compounds.

UsesChiral ligand for metal mediated asymmetric catalysis.

General Description(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene is an axially dissymmetric bis(triaryl)phosphine ligand for asymmetric reactions.

Suppliers50 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [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]
T&W GROUP021-61551611 13296011611 · [email protected]

Related reactions

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Linked notes

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