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674656

Sigma-Aldrich

(R)-(+)-2-Methyl-CBS-oxazaborolidine solution

1 M in THF

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Synonym(s):
α,α-Diphenyl-D-prolinolmethylboronic acid cyclamide ester, (R)-1-Methyl,3,3-diphenyl-tetrahydro-pyrrolo(1,2-c)(1,3,2)oxazaborole, (R)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole
Empirical Formula (Hill Notation):
C18H20BNO
CAS Number:
112022-83-0
Molecular Weight:
277.17
MDL number:
MFCD00078440
UNSPSC Code:
12352005
PubChem Substance ID:
24885228
NACRES:
NA.22

optical activity

[α]22/D +76.8°, c = 1 in toluene

Quality Level

100

concentration

1 M in THF

refractive index

n20/D 1.4602

density

0.942 g/mL at 25 °C

SMILES string

[H][C@]12CCCN1B(C)OC2(c3ccccc3)c4ccccc4

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-/m1/s1

InChI key

VMKAFJQFKBASMU-QGZVFWFLSA-N

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Related Categories

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.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - STOT SE 3

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

EUH019

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Stemmler, R.T.
Synlett, 997-997 (2007)
Current Science, 78, 1314-1317 (2000)
Singh, V. K.
Synthesis, 605-605 (1992)
Corey, E. J. et al.
Journal of the American Chemical Society, 109, 5551-5551 (1987)
Angewandte Chemie (International Edition in English), 37, 1986-1986 (1998)
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