(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

• ChemBase ID: 141220
• Molecular Formular: C18H20BNO
• Molecular Mass: 277.1685
• Monoisotopic Mass: 277.16379467
• SMILES: B1(N2CCC[C@H]2C(O1)(c1ccccc1)c1ccccc1)C
• Canonical SMILES: CB1OC([C@H]2N1CCC2)(c1ccccc1)c1ccccc1
• InChI: 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
• InChIKey: VMKAFJQFKBASMU-KRWDZBQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole
• IUPAC Traditional name: (3aS)-1-methyl-3,3-diphenyl-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole
• Synonyms: (S)-(-)-2-Methyl-CBS-oxazaborolidine; α,α-Diphenyl-L-prolinol methylboronic acid cycl-amide ester; (S)-1-Methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2c][1,3,2]oxazaborole; (S)-3,3-Diphenyl-1-methyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole; (S)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole; (S)-(-)-2-Methyl-CBS-oxazaborolidine solution; (S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole; (S)-2-Methyl-CBS-oxazaborolidine monohydrate; (S)-2-Methyl-CBS-oxazaborolidine, 1M soln. in toluene; (S)-(-)-2-甲基-CBS-噁唑硼烷; α,α-二苯基-L-脯氨醇甲基硼酸环胺酯; (S)-3,3-二苯基-1-甲基四氢-3H-吡咯并[1,2-c][1,3,2]噁唑硼烷; (S)-四氢-1-甲基-3,3-二苯基-1H,3H-吡咯并[1,2-c][1,3,2]噁唑硼烷; (S)-1-甲基-3,3-二苯基-四氢-吡咯并[1,2c][1,3,2]噁唑硼烷; (S)-(-)-2-甲基-CBS-噁唑硼烷 溶液; (S)-2-甲基-CBS-氧杂硼啶单水合物; (S)-2-甲基-CBS-氧杂硼啶, 1M 甲苯溶液

Database IDs

• CAS Number: 112022-81-8
• MDL Number: MFCD00078439
• Beilstein Number: 8492123
• PubChem SID: 162235455; 24885227; 24883643; 24869386
• PubChem CID: 2734713

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.2477818
• LogD (pH = 7.4): 4.4010496
• Log P: 4.4034
• Molar Refractivity: 81.1142 cm^3
• Polarizability: 33.783737 Å^3
• Polar Surface Area: 12.47 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 115-121°C
• Boiling Point: 111 °C
• Flash Point: -15 °C; 39.2 °F; 4 °C; 4°C(39°F); 5 °F
• Density: 0.925; 0.929 g/mL at 25 °C; 0.942 g/mL at 25 °C
• Refractive Index: n20/D 1.460
• Optical Rotation: -67 (c=1 in methanol)

Safety Information

• Storage Warning: Air & Moisture Sensitive
• European Hazard Symbols: Flammable (F); X; Irritant (Xi); Harmful (Xn)
• UN Number: 1294; 2056; UN1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-19-36/37/38; 11-20-38-48/20-63-65-67; 36/37/38; 63-11-36/37/38-48/20-65-67
• Safety Statements: 16-26; 16-26-36/37-62; 26; 36/37-46-62
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS07; GHS08
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H224-H304-H361-H373-H332-H315-H336; H225-H304-H315-H319-H335-H336-H361d-H373; H225-H315-H319-H335; H315-H319-H335
• GHS Precautionary statements: P210-P241-P301+P310-P303+P361+P353-P405-P501A; P210-P261-P281-P301 + P310-P305 + P351 + P338-P331; P210-P261-P305 + P351 + P338; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1294 3/PG 2; UN 2056 3/PG 2
• Supplemental Hazard Statements: May form explosive peroxides.
• Storage Temperature: room temp

Product Information

• Purity: ≥95.0%; 94%
• Concentration: 1 M in THF; 1 M in toluene; 1M soln. in toluene
• Empirical Formula (Hill Notation): C18H20BNO

DETAILS

Sigma Aldrich - 674648

Packaging
5, 25 mL in glass bottle
Application
CBS Catalysts for Asymmetric Reduction and Asymmetric Synthesis
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, C2-symmetrical ferrocenyl diols, and propargyl alcohols.

Sigma Aldrich - 457701

Packaging
25 mL in Sure/Seal™
5 mL in glass bottle
Application
CBS Catalysts for Asymmetric Reduction and Asymmetric Synthesis
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, C2-symmetrical ferrocenyl diols, and propargyl alcohols.

Sigma Aldrich - 649309

Packaging
1, 10 g in glass bottle
Application
CBS Catalysts for Asymmetric Reduction and Asymmetric Synthesis
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, C2-symmetrical ferrocenyl diols, and propargyl alcohols.

REFERENCES

• Anhydrous catalyst for 'CBS' reduction reaction. For examples of use in asymmetric reduction of ketones, see: Org. Synth. Coll., 9, 362, 676 (1998). For further information, see (S)-2-Methyl-CBS-oxazaborolidine monohydrate, L09219.
• Air-stable solid prepared by a modification of Corey's procedure, on which his literature results were based. For anhydrous reagent, see (S)-2-Methyl-CBS-oxazaborolidine, L14583.
• Catalyst for the CBS (Corey, Bakshi, Shibata) reduction of prochiral ketones with borane-THF, with high enantioselectivity (see (S)-(-)-ɑ,ɑ-Diphenylprolinol, L09217): J. Am . Chem. Soc., 109, 7925 (1987):
  
• For successful use of this system in a scaled up asymmetric synthesis of the antiarrythmia agent d-Sotalol, see: Org. Process Res. Dev., 1. 176 (1997). For use in enantioselective reduction of ketones containing heteroatoms, see: Tetrahedron Lett., 34, 785 (1993). For the asymmetric reduction of ɑ-ketoimines, see: Tetrahedron Lett., 35, 5551 (1994).
• For reviews of oxazaborolidines as enantioselective catalysts, see: Angew. Chem. Int. Ed., 31, 729 (1992); 37, 1986 (1998); Tetrahedron: Asymmetry, 3, 1475 (1992).
• For reviews of the asymmetric reduction of ketones, see: Synthesis, 605 (1992); Chem. Ind. (London), 552 (1994).