ChemicalBook Product Catalog Chemical Reagents Organic reagents Borane (S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole

(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole

(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole Basic information
Reaction
Product Name:(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole
Synonyms:(S)-1-METHYL-3,3-DIPHENYL-TETRAHYDRO-PYRROLO[1,2C][1,3,2]OXAZABOROLE;α,α-diphenyl-l-prolinol methylboronic acid cycl-amide-ester;(S)-(+)-Methyl-CBS-oxazaborolidine;(S)-5,5-DIPHENYL-2-METHYL-3,4-PROPANO-1,3,2-OXAZABOROLIDINE 98+%;(S)-METHYL-CBS-OXAZABOROLIDINE,1M SOLN.IN TOLUENE;(S)-Methyl oxazaborolidine, in toluene, 1M solution;(S)-3,3-DIPHENYL-1-METHYLTETRAHYDRO-3H-P YRROLO-OXAZABOROLE;(S)-2-METHYL-CBS-OXAZABOROLIDINE, 1M SOL UTION IN TOLUENE
CAS:112022-81-8
MF:C18H20BNO
MW:277.17
EINECS:601-150-5
Product Categories:organic or inorganic borate;API intermediates;Asymmetric Synthesis;B (Classes of Boron Compounds);B-Bromocatecholborane, etc.;Synthetic Organic Chemistry;Asymmetric Synthesis;Chiral Catalysts, Ligands, and Reagents;Reduction
Mol File:112022-81-8.mol
(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole Structure
(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole Chemical Properties
Melting point 115-117°C
Boiling point 111 °C
density 0.93 g/mL at 20 °C(lit.)
refractive index -68 ° (C=1, MeOH)
Fp 40 °F
storage temp. room temp
pka1.02±0.40(Predicted)
form Liquid
color Colorless to amber
Water Solubility Hydrolyzes in water.
Sensitive Air & Moisture Sensitive
BRN 8492123
Exposure limitsACGIH: TWA 20 ppm
OSHA: Ceiling 300 ppm; TWA 200 ppm
NIOSH: IDLH 500 ppm; TWA 100 ppm(375 mg/m3); STEL 150 ppm(560 mg/m3)
InChIKeyVMKAFJQFKBASMU-KRWDZBQOSA-N
CAS DataBase Reference112022-81-8(CAS DataBase Reference)
Safety Information
Hazard Codes Xi,Xn,F
Risk Statements 36/37/38-67-65-63-48/20-11-19-40
Safety Statements 26-62-36/37-33-29-16
RIDADR UN 1294 3/PG 2
WGK Germany 3
F 10-21
HazardClass 3
PackingGroup II
HS Code 29349990
MSDS Information
(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole Usage And Synthesis
Reaction
  1. Convenient catalyst for the enantioselective borane reduction of ketones at ambient temperatures.
  2. Asymmetric synthesis of α-chiral hydroxyalkylphosphines via a catalytic, enantioselective reduction of acylphosphines.
  3. Nickel-catalyzed cross-couplings of benzylic pivalates with arylboroxines: Stereospecific formation of diarylalkanes and triarylmethanes.
  4. Enantioselective reduction of prochiral ketones with NaBH4/Me2SO4/(S)-Me-CBS.
Reactions of 112022-81-8
Chemical PropertiesColorless to yellow liquid
Uses(S)-2-Methyl-CBS-oxazaborolidine is used as an oxazaborolidine catalyst. It is also employed 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. It is an anhydrous catalyst for 'CBS' reduction reaction.
Usessuzuki reaction
(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole Preparation Products And Raw materials
Raw materialsTetrahydrofuran-->Dichloromethane-->Thionyl chloride-->L-Proline-->PHENYLMAGNESIUM BROMIDE-->Trimethylboroxine
CATECHOLBORANE (4S)-(+)-4-Benzyl-3-propionyl-2-oxazolidinone Phosphorus trichloride p-Anisic acid Tetrahydrofuran Lithium hydride (R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole (S)-O-TOLYL-CBS-OXAZABOROLIDINE, 0.5M I& (S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole Methylboronic acid (S)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol (R)-Tetrahydro-1,3,3-triphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxaborole, 99% (R)-Phenyl oxazaborolidine (R)-O-TOLYL-CBS-OXAZABOROLIDINE, 0.5M I& L-(+)-Prolinol (S)-CBS-BORANE COMPLEX (S)-Tetrahydro-1,3,3-triphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxaborole, 99% (S)-Phenyl oxazaborolidine
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