(3aR)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

• ChemBase ID: 125073
• Molecular Formular: C18H20BNO
• Molecular Mass: 277.1685
• Monoisotopic Mass: 277.16379467
• SMILES: O1B(N2CCC[C@@H]2C1(c1ccccc1)c1ccccc1)C
• Canonical SMILES: CB1OC([C@@H]2N1CCC2)(c1ccccc1)c1ccccc1
• InChI: 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
• InChIKey: VMKAFJQFKBASMU-QGZVFWFLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole
• IUPAC Traditional name: (3aR)-1-methyl-3,3-diphenyl-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole
• Synonyms: (R)-(+)-2-Methyl-CBS-oxazaborolidine; α,α-Diphenyl-D-prolinol methylboronic acid cycl-amide-ester; (R)-3,3-Diphenyl-1-methyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole; (R)-Methyl oxazaborolidine; (R)-(+)-2-methyl-CBS-oxazaborolidine; (R)-2-Methyl-CBS-oxazaborolidine; 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; (R)-(+)-2-Methyl-CBS-oxazaborolidine solution; (R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole; (R)-2-Methyl-CBS-oxazaborolidine monohydrate; (R)-2-Methyl-CBS-oxazaborolidine, 1M soln. in toluene; (R)-(+)-2-甲基-CBS-噁唑硼烷; α,α-二苯基-D-脯氨醇甲基硼酸环酰胺酯; (R)-2-甲基-CBS-噁唑硼烷; (R)-四氢-1-甲基-3,3-二苯基-1H,3H-吡咯并[1,2-c][1,3,2]噁唑硼烷; (R)-1-甲基,3,3-二苯基-四氢-吡咯并(1,2-c)(1,3,2)噁唑硼烷; (R)-3-甲基-CBS-氧杂硼啶; (R)-(+)-2-甲基-CBS-噁唑硼烷 溶液; (R)-2-甲基-CBS-氧杂硼啶单水合物; (R)-2-甲基-CBS-氧杂硼啶, 1M 甲苯溶液

Database IDs

• CAS Number: 112022-83-0
• MDL Number: MFCD00078440
• Beilstein Number: 9059874
• PubChem SID: 162219423; 24869385; 24883644; 24867003; 24885228
• PubChem CID: 9838490
• Chemspider ID: 8014210
• Wikipedia Title: (R)-2-Methyl-CBS-oxazaborolidine

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.2477818
• LogD (pH = 7.4): 4.4010496
• Log P: 4.4034
• Molar Refractivity: 81.1142 cm^3
• Polarizability: 33.783737 Å^3
• Polar Surface Area: 12.47 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Colorless to pale yellow liquid (in toluene)
• Melting Point: 77-82 °C; 85-95 °C; 85-95 °C(lit.)
• Boiling Point: 111 °C
• Flash Point: 1.4 °F; -17 °C; 39.2 °F; 4 °C; 4°C(39°F)
• Density: 0.925; 0.942 g/mL at 25 °C; 0.95 g/mL; 0.95 g/mL at 25 °C
• Refractive Index: n20/D 1.4602
• Optical Rotation: [α]20/546 +43±3°, c = 1% in methanol; [α]22/D +76.8°, c = 1 in toluene; +74 (c=1 in methanol)

Safety Information

• Storage Warning: Air & Moisture Sensitive
• European Hazard Symbols: Flammable (F); X; Irritant (Xi); Harmful (Xn)
• UN Number: 1294; 2056; UN1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-19-36/37; 11-20-38-48/20-63-65-67; 63-11-38-48/20-65-67; R17
• Safety Statements: 16-26; 16-36/37-62; 36/37-46-62
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H224-H304-H361-H373-H332-H315-H336; H225-H304-H315-H336-H361d-H373; H225-H319-H335
• GHS Precautionary statements: P210-P241-P301+P310-P303+P361+P353-P405-P501A; P210-P261-P281-P301 + P310-P331; P210-P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• RID/ADR: UN 1294 3/PG 2; UN 2056 3/PG 2
• Supplemental Hazard Statements: May form explosive peroxides.
• Storage Temperature: 2-8°C; room temp

Product Information

• Purity: ≥95%; ≥95.0% (HPLC); 94%
• Concentration: 1 M in THF; 1 M in toluene; 1M soln. in toluene
• Empirical Formula (Hill Notation): C18H20BNO

DETAILS

Sigma Aldrich - 649317

Packaging
1, 10 g in glass bottle
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.

Sigma Aldrich - 674656

Packaging
5, 25 mL in glass bottle
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.

Sigma Aldrich - 457698

Packaging
25 mL in Sure/Seal™
5 mL in glass bottle
Physical form
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.
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.Used in a desymmetrizing reduction leading to (S)-4-hydroxycyclohexenone.

REFERENCES

• Anhydrous catalyst for CBS reduction reaction. For further information, see (S)-2-Methyl-CBS-oxazaborolidine monohydrate, L09219.
• Air-stable solid prepared by a modification of Corey's procedure, on which his literature results were based. For anhydrous reagent, see (R)-2-Methyl-CBS-oxazaborolidine, L14582.
• Chiral auxiliary for the highly enantioselective reduction of prochiral ketones, see (S)-2-Methyl-CBS-oxazaborolidine monohydrate, L09219.