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457701

Sigma-Aldrich

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

1 M in toluene

Synonyme(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

Formule empirique (notation de Hill):
C18H20BNO
Numéro CAS:
112022-81-8
Poids moléculaire :
277.17
Numéro MDL:
MFCD00078439
Code UNSPSC :
12352005
ID de substance PubChem :
24869386
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Concentration

1 M in toluene

Point d'ébullition

111 °C

Densité

0.929 g/mL at 25 °C

Groupe fonctionnel

phenyl

Température de stockage

room temp

Chaîne SMILES 

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

Clé InChI

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.

Autres remarques

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.

Mention d'avertissement

Danger

Classification des risques

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

Organes cibles

Central nervous system

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

39.2 °F - closed cup

Point d'éclair (°C)

4 °C - closed cup

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificats d'analyse (COA)

Lot/Batch Number
SHBR4393
SHBH5749
SHBH6193
BGBC3278V
BGBC2333V

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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.

Asymmetric Catalysis with Chiral Oxazaborolidinium Ions (COBIs)

Learn about the applications of chiral oxazaborolidinium ions (COBIs) as Lewis acid catalysts in different asymmetric reactions such as cyclopropanation, epoxidation, and radical reactions along with details of their catalytic action.

Asymmetric Catalysis with Chiral Oxazaborolidinium Ions (COBIs)

Learn about the applications of chiral oxazaborolidinium ions (COBIs) as Lewis acid catalysts in different asymmetric reactions such as cyclopropanation, epoxidation, and radical reactions along with details of their catalytic action.

Asymmetric Catalysis with Chiral Oxazaborolidinium Ions (COBIs)

Learn about the applications of chiral oxazaborolidinium ions (COBIs) as Lewis acid catalysts in different asymmetric reactions such as cyclopropanation, epoxidation, and radical reactions along with details of their catalytic action.

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