457701

(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
• 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

Properties

• concentration: 1 M in toluene
• bp: 111 °C
• density: 0.929 g/mL at 25 °C
• functional group: phenyl
• 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

Description

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.[1]
It may also be used in the preparation of:

• (1S)-2-azido-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol[2]
• (R)-α-deuteriobenzyl alcohol[3]
• (R)-2-(1-hydroxyethyl)benzo[b]thiophene[4]

Catalyst employed in an enantioselective synthesis of (S)-2-amino-1-phenylethanol.[5]

Excellent catalyst for asymmetric reductions.[6][7]

The CBS (Corey-Bakshi-Shibata) oxazaborolidine catalyst has been used in the asymmetric reduction of prochiral ketones.[8][9][10] Other applications include the enantioselective synthesis of α-hydroxy acids,[11][12] α-amino acids,[13][14] C₂-symmetrical ferrocenyl diols,[15] and propargyl alcohols.[16][17]

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.

Safety Information

• pictograms: GHS02,GHS08,GHS05,GHS07
• signalword: Danger
• hcodes: H225,H302,H304,H315,H318,H336,H361d,H373,H412
• pcodes: P201 - P210 - P273 - P280 - P301 + P310 + P331 - P305 + P351 + P338 + P310
• 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: 3 - Flammable liquids
• wgk_germany: WGK 3
• flash_point_f: 39.2 °F - closed cup
• flash_point_c: 4 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter