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

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

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(R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole Basic information

Product Name:
(R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole
Synonyms:
  • ALPHA,ALPHA-DIPHENYL-D-PROLINOL METHYLBORONIC ACID CYCL-AMIDE-ESTER
  • (R)-(+)-2-METHYL-CBS-OXAZABOROLIDINE
  • (R)-Methyloxazaborolidine,1-1.5Mintoluene[(R)-MeCBS]CoreyCatalyst
  • (r)-(+)-2-methyl-cbs-oxazaborolidine solution
  • (r)-2-methyl-cbs-oxazaborolidine, 1m soln. in toluene
  • α,α-diphenyl-d-prolinol methylboronic acid cycl-amide-ester
  • α,α-diphenyl-d-prolinolmethylboronic acid cyclamide ester
  • (R)-(+)-Methyl-CBS-oxazaborolidine
CAS:
112022-83-0
MF:
C18H20BNO
MW:
277.17
EINECS:
000-000-0
Product Categories:
  • Asymmetric Synthesis
  • Chiral Catalysts, Ligands, and Reagents
  • Asymmetric Synthesis
  • B (Classes of Boron Compounds)
  • B-Bromocatecholborane, etc.
  • Reduction
  • Synthetic Organic Chemistry
  • organic or inorganic borate
Mol File:
112022-83-0.mol
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(R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole Chemical Properties

Melting point:
85-95 °C(lit.)
Boiling point:
111 °C
Density 
0.95 g/mL at 25 °C
refractive index 
68 ° (C=1, MeOH)
Flash point:
40 °F
storage temp. 
room temp
solubility 
soluble in Chloroform, Methanol
pka
1.02±0.40(Predicted)
form 
Liquid
color 
Colorless to amber
optical activity
[α]22/D +76.8°, c = 1 in toluene
Water Solubility 
Not miscible or difficult to mix in water.
Sensitive 
Air & Moisture Sensitive
BRN 
9059874
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-QGZVFWFLSA-N
CAS DataBase Reference
112022-83-0(CAS DataBase Reference)
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Safety Information

Hazard Codes 
F,Xn,Xi
Risk Statements 
11-38-48/20-63-65-67-36/37-19-40
Safety Statements 
36/37-62-33-29-16-2-26
RIDADR 
UN 1294 3/PG 2
WGK Germany 
3
10
HazardClass 
3
PackingGroup 
II
HS Code 
29319090

MSDS

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(R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole Usage And Synthesis

Reactions

  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. 

Chemical Properties

white to light yellow crystal powde

Uses

suzuki reaction

Uses

(R)-2-Methyl-CBS-oxazaborolidine is 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. It is also used in a desymmetrizing reduction leading to (S)-4-hydroxycyclohexenone. It is useful in the production of stereospecific motifs such as α-hydroxy acids, α-amino acids, symmetrical ferrocenyl diols and propargyl alcohols.

Uses

CBS Catalysts for Asymmetric Reduction and Asymmetric Synthesis

(R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole Preparation Products And Raw materials

Preparation Products

(R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaboroleSupplier

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