(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
- 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)-1-METHYL-3,3-DIPHENYLHEXAHYDROPYRROLO[1,2-C][1,3,2]OXAZABOROLE
- (S)-5,5-DIPHENYL-2-METHYL-3,4-PROPANO-1,3,2-OXAZABOROLIDINE 98+%
- (S)-METHYL-CBS-OXAZABOROLIDINE,1M SOLN.IN TOLUENE
- (S)-Me-CBS Catalyst
- (S)-Methyl oxazaborolidine, in toluene, 1M solution
- 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 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)
- Flash point:
- 40 °F
- storage temp.
- room temp
- form
- Liquid
- pka
- 1.02±0.40(Predicted)
- color
- Colorless to amber
- Water Solubility
- Hydrolyzes in water.
- Sensitive
- Air & Moisture Sensitive
- BRN
- 8492123
- Exposure limits
- ACGIH: 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) - InChIKey
- VMKAFJQFKBASMU-KRWDZBQOSA-N
- CAS DataBase Reference
- 112022-81-8(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
- Language:English Provider:(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole
- Language:English Provider:SigmaAldrich
- Language:English Provider:ALFA
(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole Usage And Synthesis
Reaction
- Convenient catalyst for the enantioselective borane reduction of ketones at ambient temperatures.
- Asymmetric synthesis of α-chiral hydroxyalkylphosphines via a catalytic, enantioselective reduction of acylphosphines.
- Nickel-catalyzed cross-couplings of benzylic pivalates with arylboroxines: Stereospecific formation of diarylalkanes and triarylmethanes.
- Enantioselective reduction of prochiral ketones with NaBH4/Me2SO4/(S)-Me-CBS.
Chemical Properties
Colorless 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.
Uses
suzuki reaction
Synthesis
13061-96-6
22348-32-9
112022-81-8
Under nitrogen protection, (R)-(+)-α,α-diphenylprolinol (2.53 kg, 10 mol) and methylboronic acid (779 g, 13 mol) as well as 7.1 L of n-heptane were added to a reactor fitted with a reflux manifold. The mixture was stirred slowly and the solution gradually clarified as the water continued to separate. The stirring speed was then adjusted to conventional. When the water was completely separated, stirring was stopped and the reaction mixture was cooled to 40 °C and left to stand overnight. The reaction mixture was filtered through diatomaceous earth, and the filtrate was further cooled to -10°C and stirred for 1.5 hours to promote precipitation. The precipitate was collected by filtration and the product was vacuum dried in a double cone vacuum dryer at 40 °C for 8 h to give 2.30 kg (S)-2-methyl-CBS-oxazaborolidine in 83% yield. The product was a white solid with a GC purity of 98.2% and a water content of 0.31%.
References
[1] Patent: CN106478703, 2017, A. Location in patent: Paragraph 0015; 0016
(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole Preparation Products And Raw materials
Raw materials
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(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole(112022-81-8)Related Product Information
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- (R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole
- (R)-Tetrahydro-1,3,3-triphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxaborole, 99% (R)-Phenyl oxazaborolidine
- (S)-O-TOLYL-CBS-OXAZABOROLIDINE, 0.5M I&
- (S)-Tetrahydro-1,3,3-triphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxaborole, 99% (S)-Phenyl oxazaborolidine
- (S)-CBS-BORANE COMPLEX
- (S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole
- (R)-O-TOLYL-CBS-OXAZABOROLIDINE, 0.5M I&