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(R)-2-methyl-CBS-oxazaborolidine CAS 112022-83-0

(R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole CAS 112022-83-0

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

 Name:    (R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole
Synonyms:    (R)-2-METHYL-CBS-OXAZABOROLIDINE;(R)-2-METHYL-CBS-OXAZABOROLIDINE MONOHYDRATE;(R)-1-METHYL,3,3-DIPHENYL-TETRAHYDRO-PYRROLO(1,2-C)(1,3,2)OXAZABOROLE;(R)-3,3-DIPHENYL-1-METHYLTETRAHYDRO-1H,3H-PYRROLO[1,2-C][1,3,2]OXAZABOROLE;(R)-3,3-DIPHENYL-1-METHYLTETRAHYDRO-3H-PYRROLO-[1,2-C][1,3,2]OXAZABOROLE;(R)-5,5-DIPHENYL-2-METHYL-3,4-PROPANO-1,3,2-OXAZABOROLIDINE;(R)-TETRAHYDRO-1-METHYL-3,3-DIPHENYL-1H,3H-PYRROLO[1,2-C][1,3,2] OXAZABOROLE;(R)-TETRAHYDRO-1-METHYL-3,3-DIPHENYL-1H,3H-PYRROLO[1,2-C][1,3,2]OXAZOBOROLE
CAS:    112022-83-0
MF:    C18H20BNO
MW:    277.17
EINECS:    -0
Product Categories:    organic or inorganic borate;Asymmetric Synthesis;B (Classes of Boron Compounds);B-Bromocatecholborane, etc.;Synthetic Organic Chemistry;Asymmetric Synthesis;Chiral Catalysts, Ligands, and Reagents;Reduction
Mol File:    112022-83-0.mol
(R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole Structure

(R)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine; 1H,3H-Pyrrolo[1,2-c][1,3,2]oxazaborole,tetrahydro-1-methyl-3,3-diphenyl-, (3aR)-; (R)-3,3-Diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole; (R)-1-methyl-3,3-diphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaborole; (R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole;

(R)-2-Methyl-CBS-oxazaborolidine is an organoboron catalyst that is used in organic synthesis. This catalyst, developed by Itsuno and Elias James Corey, is generated by heating (R)-(+)-2-(diphenylhydroxymethyl) pyrrolidine along with trimethylboroxine or methylboronic acid. It is an excellent tool for the synthesis of alcohols in high enantiomeric ratio. Generally, 2-10 mol% of this catalyst is used along with borane-tetrahydrofuran (THF), borane-dimethylsulfide, borane-N,N-diethylaniline, or diborane as the borane source. Enantioselective reduction using chiral oxazaborolidine catalysts has been used in the synthesis of commercial drugs such as ezetimibe and aprepitant.

Appearance & Physical State     white to light yellow crystal powder
Density     0.925
Boiling Point     377.5ºC at 760 mmHg
Melting Point     85-95ºC
Flash Point     182.1ºC
Storage Condition     2-8ºC
Vapor Pressure     0mmHg at 25°C
Safety Info
Safety Statements     S16-S25-S29-S33
HS Code     2934999090
Packing Group     II
RIDADR     UN 1294 3

(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)
Fp     40 °F
storage temp.     2-8°C
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
InChIKey    VMKAFJQFKBASMU-QGZVFWFLSA-N
CAS DataBase Reference    112022-83-0(CAS DataBase Reference)
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
F     10
HazardClass     3
PackingGroup     II
HS Code     29319090
MSDS Information

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

Chemical Properties    white to light yellow crystal powde
Uses    suzuki reaction
(R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole Preparation Products And Raw materials
Preparation Products    4H-AMINO-6-BROMO-2,3-DIHYDROTHIOCHROMEN-1,1-DIOXIDE-->4-Hydroxy-6-bromo-2,3-dihydrothiochromen-1,1-dioxide

(3aR)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole;1H,3H-Pyrrolo[1,2-c][1,3,2]oxazaborole,tetrahydro-1-methyl-3,3-diphenyl-, (R)-;(R)-Me-CBS;(R)-Me-Corey-Bakshi-Shibatareagent;(R)-Methyl-CBS;(R)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole;(R-Methyl-Corey-Bakshi-Shibata catalyst;