(S)-(−)-2-Methyl-CBS-oxazaborolidine solution - 1 M in toluene , CAS No.112022-81-8

CAS: 112022-81-8 Cat. No.: S431489 Molecular Weight: 277.17 EC Number: 601-150-5

GRADE & PURITY 1 M in toluene

Synonyms

1-Methyl-3,3-diphenyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole # | (S)-2-METHYL-CBS-OXAZABOROLIDINE MONOHYDRATE | (S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2] oxazaborol | (3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]o

Storage

Room temperature

Shipped In

Normal

Overview

Application

Excellent catalyst for asymmetric reductions. CBS Catalysts for Asymmetric Reduction and Asymmetric Synthesis ( S )-(-)-2-Methyl-CBS-oxazaborolidine solution [1M in toluene] may be used as a catalyst in the multi-step synthesis of (-)-diospongin A. It may also be used in the preparation of: (1 S )-2-azido-1-(2,2-dimethyl-4 H -1,3-benzodioxin-6-yl)ethanol ( R )-α-deuteriobenzyl alcohol ( R )-2-(1-hydroxyethyl)benzo[ b ]thiophene Catalyst employed in an enantioselective synthesis of ( S )-2-amino-1-phenylethanol. The CBS (Corey-Bakshi-Shibata) oxazaborolidine catalyst has been used in the asymmetric reduction of prochiral ketones. Other applications include the enantioselective synthesis of α-hydroxy acids, α-amino acids, C 2 -symmetrical ferrocenyl diols, and propargyl alcohols.

Other Notes

Precipitate may form in storage, but does not affect product quality. Gently heat product to 80-90 °C under an inert atmosphere to redissolve solids.

Specifications

Synonyms

1-Methyl-3, 3-diphenyltetrahydro-3H-pyrrolo[1, 2-c][1, 3, 2]oxazaborole # | (S)-2-METHYL-CBS-OXAZABOROLIDINE MONOHYDRATE | (S)-3, 3-diphenyl-1-methyltetrahydro-1H, 3H-pyrrolo[1, 2-c][1, 3, 2] oxazaborol | (3aS)-1-methyl-3, 3-diphenyl-hexahydropyrrolo[1, 2-c][1, 3, 2]o

Specifications & Purity

1 M in toluene

Storage

Room temperature

Shipped In

Normal

Names and Identifiers

• Canonical Smiles: B1(N2CCCC2C(O1)(C3=CC=CC=C3)C4=CC=CC=C4)C
• IUPAC Name: (3aS)-1-methyl-3,3-diphenyl-3a,4,5,6-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole
• InChIKey: VMKAFJQFKBASMU-KRWDZBQOSA-N
• INCHI: 1S/C18H20BNO/c1-19-20-14-8-13-17(20)18(21-19,15-9-4-2-5-10-15)16-11-6-3-7-12-16/h2-7,9-12,17H,8,13-14H2,1H3/t17-/m0/s1
• Isomeric SMILES: B1(N2CCC[C@H]2C(O1)(C3=CC=CC=C3)C4=CC=CC=C4)C
• WGK Germany: 3
• UN Number: UN 2056
• Packing Group: II
• Molecular Weight: 277.17
• Reaxy-Rn: 13756891
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=13756891&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Diphenylmethanes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Diphenylmethanes
• Intermediate Tree Nodes: Not available
• Direct Parent: Diphenylmethanes
• Alternative Parents: Pyrrolidines Boronic acid esters Oxacyclic compounds Organic metalloid salts Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Monoalkylboranes Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Diphenylmethane - Boronic acid ester - Pyrrolidine - Boronic acid derivative - Organoheterocyclic compound - Organic metalloid salt - Oxacycle - Azacycle - Organic nitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Organic salt - Alkylborane - Organooxygen compound - Organonitrogen compound - Organoboron compound - Monoalkylborane - Organic oxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Specific Rotation[α]: -68° (C=1,MeOH)
• Flash Point(°C): 4°
• Molecular Weight: 277.200 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 277.164 Da
• Monoisotopic Mass: 277.164 Da
• Topological Polar Surface Area: 12.500 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 344.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

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