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457701

Sigma-Aldrich

(S)-(−)-2-Methyl-CBS-oxazaborolidine solution

1 M in toluene

Synonym(s):

α,α-Diphenyl-L-prolinol methylboronic acid cycl-amide ester, (S)-1-Methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2c][1,3,2]oxazaborole, (S)-3,3-Diphenyl-1-methyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole, (S)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole

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About This Item

Empirical Formula (Hill Notation):
C18H20BNO
CAS Number:
112022-81-8
Molecular Weight:
277.17
MDL number:
MFCD00078439
UNSPSC Code:
12352005
PubChem Substance ID:
24869386
NACRES:
NA.22

concentration

1 M in toluene

bp

111 °C

density

0.929 g/mL at 25 °C

storage temp.

room temp

SMILES string

CB1OC([C@@H]2CCCN12)(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-/m0/s1

InChI key

VMKAFJQFKBASMU-KRWDZBQOSA-N

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Application

CBS Catalysts for Asymmetric Reduction and Asymmetric Synthesis
(S)-(-)-2-Methyl-CBS-oxazaborolidine solution [1M in toluene] may be used as a catalyst in the multi-step synthesis of (-)-diospongin A.
It may also be used in the preparation of:
  • (1S)-2-azido-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol
  • (R)-α-deuteriobenzyl alcohol
  • (R)-2-(1-hydroxyethyl)benzo[b]thiophene
Catalyst employed in an enantioselective synthesis of (S)-2-amino-1-phenylethanol.
Excellent catalyst for asymmetric reductions.
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.

Other Notes

Precipitate may form in storage, but does not affect product quality. Gently heat product to 80-90 °C under an inert atmosphere to redissolve solids.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3

Target Organs

Central nervous system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

39.2 °F - closed cup

Flash Point(C)

4 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Articles

CBS Catalysts

we are pleased to offer both enatiomers of 2-methyl-CBS-oxazaborolidine as a dry reagent, in addition to our current offerings as a 1M solution in toluene.

CBS Catalysts

We are pleased to offer o-tolyl-CBS-oxazaborolidine as a 0.5 M solution in toluene for your research needs. When protonated with trifluoromethanesulfonimide, these chiral oxazaborolidines generate chiral Lewis acids, which have demonstrated great utility in the enantioselective Diels–Alder reaction.

Related Content

2-Methyl-CBS-oxazaborolidine

Our company is pleased to offer both enantiomers of 2-methyl-CBS-oxazaborolidine as a dry reagent, in addition to our current offerings as a 1 M solution in toluene.

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