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(R)-(-)-1,1'-Binaphthol-2,2'-bis(trifluoromethanesulfonate) is a white powder chemical compound known for its significant role in the field of asymmetric catalysis. It is characterized by its unique binaphthyl structure and trifluoromethanesulfonate groups, which contribute to its reactivity and utility in various chemical reactions.

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  • 126613-06-7 Structure
  • Basic information

    1. Product Name: (R)-(-)-1,1'-Binaphthol-2,2'-bis(trifluoromethanesulfonate)
    2. Synonyms: TRIFLUOROMETHANESULFONIC ACID 2'-TRIFLUOROMETHANESULFONYLOXY-[1,1']BINAPHTHALENYL-2-YL ESTER;(R)-(-)-1,1'-BINAPHTHYL-2,2'-DIYL BIS(TRIFLUOROMETHANESULFONATE);(R)-1,1'-BINAPHTHYL-2,2'-DIYL BIS(TRIFLUOROMETHANE)SULPHONATE;(R)-(-)-1,1'-BINAPHTHOL-2,2'-BIS(TRIFLUOROMETHANESULFONATE);(R)-(-)-1,1'-BIS(2-NAPHTHOL) DITRIFLATE;(R)-1,1'-BINAPHTHALENE-2,2'-DIYL BIS(TRIFLUOROMETHANESULFONATE);(R)-(-)-1,1'-BI-2-NAPHTHYL BIS-TRIFLUOROMETHANESULFONATE;(R)-(-)-1,1'-BI-2-NAPHTHOL BIS(TRIFLUOROMETHANESULFONATE)
    3. CAS NO:126613-06-7
    4. Molecular Formula: C22H12F6O6S2
    5. Molecular Weight: 550.45
    6. EINECS: N/A
    7. Product Categories: API intermediates;Asymmetric Synthesis;Synthetic Organic Chemistry;BINOL Series;Chiral Oxygen
    8. Mol File: 126613-06-7.mol
  • Chemical Properties

    1. Melting Point: 83-85 °C(lit.)
    2. Boiling Point: 578.8 °C at 760 mmHg
    3. Flash Point: 303.9 °C
    4. Appearance: White/Powder
    5. Density: 1.5402 (estimate)
    6. Refractive Index: N/A
    7. Storage Temp.: Sealed in dry,Room Temperature
    8. Solubility: N/A
    9. Water Solubility: Insoluble
    10. Sensitive: moisture sensitive
    11. BRN: 4282753
    12. CAS DataBase Reference: (R)-(-)-1,1'-Binaphthol-2,2'-bis(trifluoromethanesulfonate)(CAS DataBase Reference)
    13. NIST Chemistry Reference: (R)-(-)-1,1'-Binaphthol-2,2'-bis(trifluoromethanesulfonate)(126613-06-7)
    14. EPA Substance Registry System: (R)-(-)-1,1'-Binaphthol-2,2'-bis(trifluoromethanesulfonate)(126613-06-7)
  • Safety Data

    1. Hazard Codes: C,Xi
    2. Statements: 34
    3. Safety Statements: 26-36/37/39-45-27
    4. RIDADR: UN 3261 8/PG 2
    5. WGK Germany: 3
    6. RTECS:
    7. F: 10-21
    8. HazardClass: 8
    9. PackingGroup: II
    10. Hazardous Substances Data: 126613-06-7(Hazardous Substances Data)

126613-06-7 Usage

Uses

Used in Chemical Synthesis:
(R)-(-)-1,1'-Binaphthol-2,2'-bis(trifluoromethanesulfonate) is used as a key intermediate for the synthesis of heterobidentate ligands, which are crucial in asymmetric catalysis. These ligands are essential for enhancing the selectivity and efficiency of various chemical reactions, particularly in the pharmaceutical and fine chemicals industries.
Used in the Preparation of Chiral Ligands:
(R)-(-)-1,1'-Binaphthol-2,2'-bis(trifluoromethanesulfonate) is used as a starting material to prepare 2-(diphenylphosphino)-2'-alkoxy-1,1'-binaphthyls by reacting with bis(aryl) phosphonic acids. These chiral ligands are vital in the development of enantioselective catalysts, which are widely used in the synthesis of chiral compounds with high optical purity.
Used in Catalyst Development:
(R)-(-)-1,1'-Binaphthol-2,2'-bis(trifluoromethanesulfonate) serves as a starting material for the synthesis of binaphthyl-based rhodium catalysts. These catalysts are employed in the hydrogenation of styrene and other related reactions, leading to the production of valuable chemicals and materials with high enantioselectivity and efficiency.

Check Digit Verification of cas no

The CAS Registry Mumber 126613-06-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,6,6,1 and 3 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 126613-06:
(8*1)+(7*2)+(6*6)+(5*6)+(4*1)+(3*3)+(2*0)+(1*6)=107
107 % 10 = 7
So 126613-06-7 is a valid CAS Registry Number.

126613-06-7 Well-known Company Product Price

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  • TCI America

  • (B2230)  (R)-(-)-1,1'-Binaphthyl-2,2'-diyl Bis(trifluoromethanesulfonate)  >96.0%(HPLC)

  • 126613-06-7

  • 1g

  • 650.00CNY

  • Detail
  • Alfa Aesar

  • (H60401)  (R)-(-)-1,1'-Bi(2-naphthol) bis(trifluoromethanesulfonate), 97%   

  • 126613-06-7

  • 1g

  • 1084.0CNY

  • Detail
  • Aldrich

  • (440590)  (R)-(−)-1,1′-Bi-2-naphtholbis(trifluoromethanesulfonate)  97%

  • 126613-06-7

  • 440590-1G

  • 732.42CNY

  • Detail

126613-06-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name (R)-(-)-1,1'-Binaphthol-2,2'-bis(trifluoromethanesulfonate)

1.2 Other means of identification

Product number -
Other names R-(-)-1,1'-Bi-2-naphthol Bis(trifluoromethanesulfonate)

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:126613-06-7 SDS

126613-06-7Relevant articles and documents

Synthesis and properties of macrocyclic diazene switch with binaphthalene unit attached via acrylamide linkers

Kickova, Anna,Kerner, Lukas,Putala, Martin,Horvath, Branislav

, p. 101 - 109,9 (2013)

2,2′-Diiodo-1,1′-binaphthalene undergoes a tandem Heck reaction with methyl acrylate to afford methyl 2-(7H-dibenzo[c,g]fluoren-7-ylidene) acetate. As a consequence, the target macrocyclic diazene with binaphthalene unit attached via acrylamide linker was prepared by the stepwise building of acrylamide at a binaphthalene moiety, including the Doebner modification of the Knoevenagel condensation, and completed by oxidative macrocyclisation of aniline end-groups. Despite being an equimolar mixture of monomer and dimer, it exhibited remarkable changes in CD spectra due to reversible (E/Z) isomerisation of N=N diazene bonds upon irradiation at 365/465 nm. Although the dimer isomerises from (E) to (Z) isomer 7.4 times faster than the monomer, the latter's contribution to the change in ellipticity at 307 nm in the photostationary state is 2.4 times greater.

Large Scale Synthesis of Chiral (3 Z,5 Z)-2,7-Dihydro-1H-azepine-Derived Hamari Ligand for General Asymmetric Synthesis of Tailor-Made Amino Acids

Takahashi, Motohiro,Moriwaki, Hiroki,Miwa, Toshio,Hoang, Brittanie,Wang, Peng,Soloshonok, Vadim A.

, p. 619 - 628 (2019)

An advanced process for large scale (500 g) preparation of a (3Z,5Z)-2,7-dihydro-1H-azepine-derived chiral tridentate ligand (Hamari ligand), widely used for asymmetric synthesis of tailor-made α-amino acids via the corresponding glycine Schiff base Ni(II

Matching and mismatching effects of hybrid chiral biaxial bisphosphine ligands in enantioselective hydrogenation of ketoesters

Sun, Xianfeng,Li, Wei,Zhou, Le,Zhang, Xumu

, p. 7302 - 7305 (2009)

A study was conducted to demonstrate matching and mismatching of hybrid chiral biaxial bisphosphine ligands in enantioselective hydrogenation of ketoesters. A novel class of conformationally rigid Cn-TunePhos was developed by introducing a bridge with variable length to link the chiral atropisometic biaryl groups. The conformationally rigid Cn-TunePhos was introduce to investigate the synthesis and use of new chiral biophosphine ligands in asymmetric catalysis. A strategy was introduced for the synthesis of a pair of diastereoisomeric forms of ligands 1, 2, and an analogous ligand 3 to assess the effects of stereochemical matching and mismatching interactions upon the structural and catalytic properties of the corresponding ruthenium complexes. Their applications in highly efficient Ru-catalyzed asymmetric hydrogenation for the enantioselective synthesis of α- and β-hydroxy acid derivatives were also explored.

Synthesis of new chiral monodentate phosphines and their use in asymmetric hydrogenation

Junge, Kathrin,Oehme, Günther,Monsees, Axel,Riermeier, Thomas,Dingerdissen, Uwe,Beller, Matthias

, p. 4977 - 4980 (2002)

A general synthesis of chiral 4,5-dihydro-3H-dinaphthophosphepines 1a-g is described. The resulting ligands represent a new class of monodentate chiral phosphines. First applications of 1a-g in the rhodium-catalyzed asymmetric hydrogenation of unsaturated

Synthesis of a novel chiral binaphthyl phospholane and its application in the highly enantioselective hydrogenation of enamides.

Xiao,Zhang,Zhang

, p. 1679 - 1681 (1999)

[formula: see text] A new chiral phosphine, (R,R)-1,2-bis[(R)-4,5-dihydro-3H-dinaphtho[2,1- c:1',2'-e]phosphepino]benzene [abbreviated as (R,R)-binaphane] was prepared on the basis of a practical route from a readily accessible enantiomerically pure binap

Chiral silanediols in anion-binding catalysis

Schafer, Andrew G.,Wieting, Joshua M.,Fisher, Thomas J.,Mattson, Anita E.

, p. 11321 - 11324 (2013)

A perfect pair: Silanediols are effective catalysts for the addition of silyl ketene acetals to N-acylisoquinolinium ions. Importantly, this is the first example of a silanediol plausibly participating in anion-binding catalysis, a relatively new direction in the field of hydrogen-bond-donor catalysis. The chiral, enantiopure C2-symmetric silanediol 1 catalyzes enantioselective transformations. Copyright

Catalytic, asymmetric aza-Baylis-Hillman reaction of N-sulfonated imines with 2-cyclohexen-1-one and 2-cyclopenten-1-one in the presence of a chiral phosphine Lewis base

Shi, Min,Li, Chao-Qun

, p. 1385 - 1391 (2005)

In the aza-Baylis-Hillman reaction of N-sulfonated imines with 2-cyclohexen-1-one or 2-cyclopenten-1-one, we found that by using (R)-2′-dimethylphosphanyl-[1,1′]binaphthalenyl-2-ol LB1 as a chiral phosphine Lewis base, the corresponding Baylis-Hillman adducts 2 or 3 can be obtained in good yields and moderate enantiomeric excess. The structure of this chiral phosphine Lewis base on chiral induction in this reaction has also been discussed.

A scalable synthesis of (R)-3,5-dihydro-4H-dinaphth[2,1-c:1′2′ -e]azepine

Ikunaka, Masaya,Maruoka, Keiji,Okuda, Yoshiaki,Ooi, Takashi

, p. 644 - 648 (2003)

Environmentally benign scalable procedures are developed to supply enantiomerically pure (R)-3,5-dihydro-4H-dinaphth[2,1-c:1′2′ -e]azepine 1 as its hydrogen oxalate salt in a five-step overall yield of 41%, which consist of the following: (1) his O-triflation of (R)-1,1′ -bi-2-naphthol 8 [(CF3SO2)2O, pyridine, PhMe; quantitative yield]; (2) Kumada's cross-coupling [MeMgI, NiCl2(dppp), tert-BuOMe; 96% yield]; (3) radical bromination [N-bromosuccinimide, 2,2′-azobisisobutyronitrile, cyclohexane; 54% yield]; (4) cyclization [allylamine, Et3N, THF, 86%]; (5) N-deallylation [1,3-dimethylbarbituric acid, Pd(OAc)2, Ph3P, PhMe] followed by crystalline salt formation with oxalic acid (overall 92% yield).

Development of a new class of C1-symmetric bisphosphine ligands for rhodium-catalyzed asymmetric hydrogenation

Dai, Qian,Li, Wei,Zhang, Xumu

, p. 6943 - 6948 (2008)

A new class of C1-symmetric bisphosphine ligands with three hindered quadrants have been obtained through facile synthesis from chiral BINOL derivatives. Their rhodium complexes have exhibited high enantioselectivities (up to 98% ee) in the asy

Supramolecular Polymerization of [5]Helicenes. Consequences of Self-Assembly on Configurational Stability

Valera, Jorge S.,Gómez, Rafael,Sánchez, Luis

, p. 2020 - 2023 (2018)

The supramolecular polymerization of [5]helicenes 1 and 2 is investigated. The self-assembly of these helicenes proceeds by the operation of H-bonding interactions with a negligible participation of π-stacking. The enantiopurity of the sample has a dramatic effect on the supramolecular polymerization mechanism since it reverts the isodesmic mechanism for the racemic mixture to a cooperative one for the enantioenriched sample. Noticeably, the formation of supramolecular polymers efficiently increases the configurational stability of 1,14-unsubstituted [5]helicenes.

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