Reaction
ChemicalBook > CAS DataBase List > (R)-H8-BINAP

(R)-H8-BINAP

Reaction
Product Name
(R)-H8-BINAP
CAS No.
139139-86-9
Chemical Name
(R)-H8-BINAP
Synonyms
(R)-H8-BINAP;(R)-H8-BINAP >=94%;(R)-2,2'-Bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl;(R)-(+)-2,2'-Bis(diphenylphospino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl;(R)-2,2'-bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthalene;(R)-(+)-2,2'-Bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl;Phosphine, [(1R)-5,5',6,6',7,7',8,8'-octahydro[1,1'-binaphthalene]-2,2'-diyl]bis[diphenyl-;(R)-(+)-2,2'-Bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl,95%,99%ee;(R)-(+)-2,2'-Bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl(R)-H8-BINAP;(R)-(+)-2,2'-Bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl (R)-(+)-H8-BINAP
CBNumber
CB1511446
Molecular Formula
C44H40P2
Formula Weight
630.74
MOL File
139139-86-9.mol
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(R)-H8-BINAP Property

Melting point:
207-208°C
Boiling point:
745.6±60.0 °C(Predicted)
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
form 
Powder
color 
off-white
optical activity
[α]20/D +74°, c = 0.5 in toluene
CAS DataBase Reference
139139-86-9
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Safety

Hazard Codes 
Xi
Risk Statements 
36/38
Safety Statements 
26
WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
692387
Product name
(R)-H8-BINAP
Purity
≥94%
Packaging
50mg
Price
$55
Updated
2023/01/07
Sigma-Aldrich
Product number
692387
Product name
(R)-H8-BINAP
Purity
≥94%
Packaging
100mg
Price
$104
Updated
2023/01/07
Strem Chemicals
Product number
15-2972
Product name
(R)-(+)-2,2'-Bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl (R)-(+)-H8-BINAP
Packaging
50mg
Price
$69
Updated
2024/03/01
Strem Chemicals
Product number
15-2972
Product name
(R)-(+)-2,2'-Bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl (R)-(+)-H8-BINAP
Packaging
250mg
Price
$276
Updated
2024/03/01
American Custom Chemicals Corporation
Product number
ING0001296
Product name
(R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-5,5',6,6',7,7',8,8'-OCTAHYDRO-1,1'-BINAPHTHYL
Purity
95.00%
Packaging
50MG
Price
$473.7
Updated
2021/12/16
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(R)-H8-BINAP Chemical Properties,Usage,Production

Reaction

  1. Biaryl bisphosphine ligand. The H8-BINAP ligand, as the ruthenium complex, catalyzes hydrogenation of unsaturated carboxylic acids to a higher ee than does BINAP.
  2. The ruthenium catalyzed hydrogenation of aryl propenoic acid to produce the drug Ibuprofen.
  3. Rhodium catalyzed asymmetric regioselective 1,4-addition of arylboronic acids to 3-substituted maleimides.
  4. Ligand for palladium-catalyzed enantioselective hydrogenation of substituted indoles.
  5. Rhodium-catalyzed enantioselective cyclization of γ-alkynylaldehydes with acyl phosphonates.
  6. Enantioselective synthesis of axially chiral 1-arylisoquinolines by Rh-catalyzed [2+2+2] cycloaddition.
  7. Enantioselective synthesis of 2,3-disubstituted indolines through Bronsted acid/Pd-complex-promoted tandem reactions.
  8. Dehydration triggered asymmetric hydrogenation of 3-(α-hydroxyalkyl)indoles
  9. Iridium-catalyzed [2+2+2] cycloaddition of α,ω-diynes with arylisocyanates
  10. Asymmetric hydrogenation of 3-(toluenesulfonamidoalkyl)-indoles
  11. Asymmetric Rh(I)-catalyzed intramolecular [3+2] cycloaddition of 1-yne-vinylcyclopropanes for bicyclo[3.3.0] compounds with a chiral quaternary carbon stereocenter.
  12. Enantioselective intermolecular [2+2+2] cycloadditions of ene-allenes with allenoates.
  13. Rh-catalyzed one-pot intermolecular [2+2+2] trimerization/asymmetric intramolecular [4+2] cycloaddition of two aryl ethynyl ethers and 5-alkynals.
  14. Rh-catalyzed regio-, diastereo-, and enantioselective [2+2+2] cycloaddition of 1,6-enynes with acrylamides.




Uses

Catalytic ligand used for:

  • Enantioselective synthesis of dihydrobenzofurans and dihydronaphthofurans via olefin isomerization/enantioselective intramolecular Alder-ene reaction of enynes catalyzed by Rh
  • Preparation of axially chiral biaryl compounds by gold-catalyzed stereoselective intramolecular hydroarylation
  • Preparation of chiral 3-alkyl-substituted indolines by tandem condensation-asymmetric hydrogenation of indoles with aldehydes, catalyzed by Bronsted acids and palladium BINAP complexes
  • Stereoselective preparation of hydrindanes and decalins containing up to four contiguous stereocenters via rhodium-catalyzed [2+2+2] cycloaddition of ene-allenes with allenes
  • Rhodium-catalyzed asymmetric formal olefination or cycloaddition of 1,3-dicarbonyl compounds with 1,6-diynes or 1,6-enynes
  • Stereoselective preparation of 2,3-substituted indolines via Pd-catalyzed hydrogenation of (α-hydroxyalkyl)indoles

General Description

The product is a diphenylphosphinobenzoic acid (DPPBA) based ligand for the palladium-catalyzed asymmetric allylic alkylation with a high degree of enantioselectivity.

(R)-H8-BINAP Preparation Products And Raw materials

Raw materials

Preparation Products

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(R)-H8-BINAP Suppliers

China 43 Japan 1 Switzerland 1 United Kingdom 1 United States 4 Global 50
Aladdin Scientific
Tel
+1-+1(833)-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
52925
Advantage
58
Riedel-de Haen AG
Tel
--
Fax
--
Country
United States
ProdList
6773
Advantage
87
Strem Chemicals, Inc.
Tel
--
Fax
--
Email
info@strem.com
Country
United States
ProdList
4910
Advantage
86
NE Scientific
Tel
--
Fax
--
Country
United States
ProdList
5030
Advantage
55
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View Lastest Price from (R)-H8-BINAP manufacturers

XINXIANG RUNYU MATERIAL CO., LTD.
Product
(R)-2,2'-Bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl；(R)-H8-Binap 139139-86-9
Price
US $0.00-0.00/g
Min. Order
1g
Purity
98%+
Supply Ability
500
Release date
2023-03-31
Zhuozhou Wenxi import and Export Co., Ltd
Product
(R)-H8-BINAP 139139-86-9
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-06-27
Career Henan Chemical Co
Product
(R)-H8-BINAP 139139-86-9
Price
US $1.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1kg,5kg,100kg
Release date
2019-08-08

139139-86-9, (R)-H8-BINAPRelated Search:

(R)-(6,6'-Dimethoxybiphenyl-2,2'-diyl)bis[bis(3,5-di-tert-butyl-4-methoxypheny (S)-(-)-2,2'-Bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (R)-SEGPHOS (R)-(+)-2,2'-Bis(di-i-propylphosphino)-6,6'-dimethoxy-1,1'-biphenyl,min.97% (S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(S)-SEGPHOS (R)-DIFLUORPHOS(TM) (S)-(+)-5,5'-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-4,4'-bi-1,3-benzodioxole,min.98%(S)-DTBM-SEGPHOS (S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL (R)-(+)-TolBINAP R(+)-2 2'-BIS-(DIPHENYLPHOSPHINO)-6 6'-& (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (S)-(-)-2,2'-BIS[BIS(3,5-DIMETHYLPHENYL)PHOSPHINO]-5,5',6,6',7,7',8,8'-OCTAHYDRO-1,1'-BINAPHTHYL Dimethylammoniumdichlorotri(mu-chloro)bis[(R)-(+)-2,2'-bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl]diruthenate(II) (R)-H8-BINAP Diacetato[(S)-(-)-2,2'-bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthy]ruthenium(II) (S)-(-)-2,2'-BIS[BIS(4-METHYLPHENYL)PHOSPHINO]-5,5',6,6',7,7',8,8'-OCTAHYDRO-1,1'-BINAPHTHYL (R)-(+)-2,2'-BIS[BIS(3,5-DITRIFLUOROMETHYLPHENYL)PHOSPHINO]-5,5',6,6',7,7',8,8'-OCTAHYDROBINAPHTHYL

  • (R)-H8-BINAP
  • (R)-(+)-2,2'-Bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl(R)-H8-BINAP
  • (R)-(+)-2,2μ-Bis(diphenylphospino)-5,5μ,6,6μ,7,7μ,8,8μ-octahydro-1,1μ-binaphthyl, [(1R)-5,5μ,6,6μ,7,7μ,8,8μ-octahydro-[1,1μ-binaphthalene]-2,2μ-diyl]bis[diphenylphosphine]
  • (R)-(+)-2,2'-Bis(diphenylphospino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl
  • (R)-(+)-2,2'-Bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl
  • (R)-H8-BINAP >=94%
  • (R)-(+)-2,2-Bis(diphenylphosphino)-5,5,6,6,7,7,8,8-octahydro-[1,1-binaphthalene]-2,2-diyl]bis[diphenylphosphine]
  • (R)-2,2'-bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthalene
  • Phosphine, [(1R)-5,5',6,6',7,7',8,8'-octahydro[1,1'-binaphthalene]-2,2'-diyl]bis[diphenyl-
  • (R)-(+)-2,2'-Bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl,95%,99%ee
  • (R)-2,2'-Bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl
  • (R)-(+)-2,2'-Bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl (R)-(+)-H8-BINAP
  • 139139-86-9
  • C44H40P2
  • BINAP Series
  • Chiral Phosphine