(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole

Reaction

Product Name: (S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole
CAS No.: 112022-81-8
Chemical Name: (S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole
Synonyms: (S)-2-METHYL-CBS-OXAZABOROLIDINE;(S)-1-METHYL-3,3-DIPHENYLHEXAHYDROPYRROLO[1,2-C][1,3,2]OXAZABOROLE;(S)-ME CBS;(S)-Me-CBS Catalyst;(S)-2-METHYL-CBS-OXAZABOROL;(S)-(-)-2-METHYL-CBS-OXAZABOROLIDINE;(s)-(-)-2-methyl-cbs-oxazaborolidine solution;(S)-5,5-DIPHENYL-2-METHYL-3,4-PROPANO-1,3,2-OXAZABOROLIDINE;(S)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole, 0.9-1.1M in toluene [(S)-Methyloxazaborolidine;(s)-methyl
CBNumber: CB3106062
Molecular Formula: C18H20BNO
Formula Weight: 277.17
MOL File: 112022-81-8.mol

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(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole Property

Melting point:: 115-117°C
Boiling point:: 111 °C
Density: 0.93 g/mL at 20 °C(lit.)
refractive index: -68 ° (C=1, MeOH)
Flash point:: 40 °F
storage temp.: room temp
form: Liquid
pka: 1.02±0.40(Predicted)
color: Colorless to amber
Water Solubility: Hydrolyzes in water.
Sensitive: Air & Moisture Sensitive
BRN: 8492123
Exposure limits: ACGIH: TWA 20 ppm
OSHA: Ceiling 300 ppm; TWA 200 ppm
NIOSH: IDLH 500 ppm; TWA 100 ppm(375 mg/m3); STEL 150 ppm(560 mg/m3)
InChIKey: VMKAFJQFKBASMU-KRWDZBQOSA-N
CAS DataBase Reference: 112022-81-8(CAS DataBase Reference)

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Safety

Hazard Codes: Xi,Xn,F
Risk Statements: 36/37/38-67-65-63-48/20-11-19-40
Safety Statements: 26-62-36/37-33-29-16
RIDADR: UN 1294 3/PG 2
WGK Germany: 3
F: 10-21
HazardClass: 3
PackingGroup: II
HS Code: 29349990

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H318Causes serious eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 457701
Product name: (S)-(?)-2-Methyl-CBS-oxazaborolidine solution
Purity: 1 M in toluene
Packaging: 5ml
Price: $102
Updated: 2025/07/31

Sigma-Aldrich

Product number: 457701
Product name: (S)-(?)-2-Methyl-CBS-oxazaborolidine solution
Purity: 1 M in toluene
Packaging: 25ml
Price: $356
Updated: 2025/07/31

TCI Chemical

Product number: D5912
Product name: (S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine (ca. 1mol/L in Toluene)
Packaging: 5ML
Price: $68
Updated: 2025/07/31

TCI Chemical

Product number: D5912
Product name: (S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine (ca. 1mol/L in Toluene)
Packaging: 25ML
Price: $182
Updated: 2025/07/31

TCI Chemical

Product number: D2131
Product name: (S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine
Purity: >98.0%(T)
Packaging: 1g
Price: $76
Updated: 2025/07/31

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(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole Chemical Properties,Usage,Production

Reaction

Convenient catalyst for the enantioselective borane reduction of ketones at ambient temperatures.
Asymmetric synthesis of α-chiral hydroxyalkylphosphines via a catalytic, enantioselective reduction of acylphosphines.
Nickel-catalyzed cross-couplings of benzylic pivalates with arylboroxines: Stereospecific formation of diarylalkanes and triarylmethanes.
Enantioselective reduction of prochiral ketones with NaBH4/Me2SO4/(S)-Me-CBS.

Chemical Properties

Colorless to yellow liquid

Uses

(S)-2-Methyl-CBS-oxazaborolidine is used as an oxazaborolidine catalyst. It is also employed 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. It is an anhydrous catalyst for 'CBS' reduction reaction.

Uses

suzuki reaction

Synthesis

13061-96-6

22348-32-9

112022-81-8

Under nitrogen protection, (R)-(+)-α,α-diphenylprolinol (2.53 kg, 10 mol) and methylboronic acid (779 g, 13 mol) as well as 7.1 L of n-heptane were added to a reactor fitted with a reflux manifold. The mixture was stirred slowly and the solution gradually clarified as the water continued to separate. The stirring speed was then adjusted to conventional. When the water was completely separated, stirring was stopped and the reaction mixture was cooled to 40 °C and left to stand overnight. The reaction mixture was filtered through diatomaceous earth, and the filtrate was further cooled to -10°C and stirred for 1.5 hours to promote precipitation. The precipitate was collected by filtration and the product was vacuum dried in a double cone vacuum dryer at 40 °C for 8 h to give 2.30 kg (S)-2-methyl-CBS-oxazaborolidine in 83% yield. The product was a white solid with a GC purity of 98.2% and a water content of 0.31%.

References

[1] Patent: CN106478703, 2017, A. Location in patent: Paragraph 0015; 0016

(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole Preparation Products And Raw materials

Raw materials

Trimethylboroxine Phenylmagnesium bromide L-Proline Tetrahydrofuran Dichloromethane Thionyl chloride

Preparation Products

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View Lastest Price from (S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole manufacturers

ZHENGZHOU JIUYI TIME NEW MATERIALS CO,.LTD

Product: (S)-(?)-2-Methyl-CBS-oxazaborolidine 112022-81-8
Price: US $1.10-9.90/kg
Min. Order: 1kg
Purity: 99%min
Supply Ability: 100kg
Release date: 2025-08-18

Henan Aochuang Chemical Co.,Ltd.

Product: (S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole 112022-81-8
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 1Ton
Release date: 2022-09-26

Zhuozhou Wenxi import and Export Co., Ltd

Product: (S)-()-2-Methyl-CBS-oxazaborolidine solution 112022-81-8
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-06-27

112022-81-8, (S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaboroleRelated Search:

(4S)-(+)-4-Benzyl-3-propionyl-2-oxazolidinone Phosphorus trichloride 4-Methoxybenzoic acid Lithium hydride Tetrahydrofuran CATECHOLBORANE (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol L-(+)-Prolinol Methylboronic acid (R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole (R)-Tetrahydro-1,3,3-triphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxaborole, 99% (R)-Phenyl oxazaborolidine (S)-O-TOLYL-CBS-OXAZABOROLIDINE, 0.5M I& (S)-Tetrahydro-1,3,3-triphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxaborole, 99% (S)-Phenyl oxazaborolidine (S)-CBS-BORANE COMPLEX (S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole (R)-O-TOLYL-CBS-OXAZABOROLIDINE, 0.5M I&

(S)-1-METHYL-3,3-DIPHENYL-TETRAHYDRO-PYRROLO[1,2C][1,3,2]OXAZABOROLE

α,α-diphenyl-l-prolinol methylboronic acid cycl-amide-ester

(S)-(+)-Methyl-CBS-oxazaborolidine

(S)-1-METHYL-3,3-DIPHENYLHEXAHYDROPYRROLO[1,2-C][1,3,2]OXAZABOROLE

(S)-5,5-DIPHENYL-2-METHYL-3,4-PROPANO-1,3,2-OXAZABOROLIDINE 98+%

(S)-METHYL-CBS-OXAZABOROLIDINE,1M SOLN.IN TOLUENE

(S)-Me-CBS Catalyst

(S)-Methyl oxazaborolidine, in toluene, 1M solution

(S)-3,3-DIPHENYL-1-METHYLTETRAHYDRO-3H-P YRROLO-OXAZABOROLE

(S)-2-METHYL-CBS-OXAZABOROLIDINE, 1M SOL UTION IN TOLUENE

(S)-2-METHYL-CBS-OXAZABOROLIDINE, 1M IN&

(S)-Methyloxazaborolidine,1-1.5Mintoluene[(S)-MeCBS]CoreyCatalyst

(s)-(-)-2-methyl-cbs-oxazaborolidine solution

(s)-2-methyl-cbs-oxazaborolidine, 1m soln. in toluene

(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, α,α-Diphenyl-L-prolinol methylboronic acid cycl-amide ester

(S)-Tetrahydro-1-methyl-3,3-triphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole, 1-1.5M in toluene [(S)-Methyl oxazaborolidine] Corey Catalyst

(3aS)-1-Methyl-3,3-diphenyl-3aβ,4,5,6-tetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole

(3aS)-1-Methyl-3,3-diphenyl-tetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole

(3aS)-3,3aβ,4,5-Tetrahydro-1-methyl-3,3-diphenyl-6H-1-bora-2-oxa-6a-azapentalene

(3aS)-3,3-Diphenyl-1-methyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole

(3aS)-3aβ,4,5,6-Tetrahydro-1-methyl-3,3-diphenyl-3H-pyrrolo[1,2-c][1,3,2]oxazaborole

(S)-()-2-Methyl-CBS-oxazaborolidine solution 1 M in THF

(S)-2-Methyl-CBS-oxazaborolidine (S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole

(S)-(-)-2-Methyl-CBS-oxazaborolidine >=95.0%

(S)-(-)-2-Methyl-CBS-oxazaborolindine

(S)-2-methyl-CBS-oxazaborolidine(1mol/L)

(S)-2-methyl-CBS-oxazaborolidine(solid)

(S)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole, 0.9-1.1M in toluene [(S)-Methyloxazaborolidine

(S)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole, 0.9-1.1M in toluene [(S)-Methyloxazaborolidine] (S)-CBS Catalyst

(3aS)-1-methyl-3,3-diphenyl-3a,4,5,6-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole

(S)-(-)-2-Methyl-CBS-oxazaborolidine, 1.0 M solution in toluene, J&KSeal

(S)-2-METHYL-CBS-OXAZABOROL

(S)-(-)-2-MethyL

(S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine - 1.0M in toluene

(3aβ)-1-Methyl-3,3-diphenyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole

1-(S)-methyl CBS oxazaborolidine

(S)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole,0.9-1.1Mintoluene[(S)-Methyloxazaborolidine]CoreyCatalyst

(S)-(-)-2-METHYL-CBS-[1,3,2]OXAZABOROLIDINE IN,TOLUENE

(S)-2-Methyl-CBS-oxazaborolidine ,98%

ALPHA,ALPHA-DIPHENYL-L-PROLINOL METHYLBORONIC ACID CYCL-AMIDE ESTER

(S)-(-)-2-Methyl-CBS-oxazaborolidine, 1M solution in toluene, AcroSeal

1-Methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

(S)-5,5-DIPHENYL-2-METHYL-3,4-PROPANO-1,3,2-OXAZABOROLIDINE

(S)-(-)-2-METHYL-CBS-OXAZABOROLIDINE

(S)-2-METHYL-CBS-OXAZABOROLIDINE

(S)-2-METHYL-CBS-OXAZABOROLIDINE MONOHYDRATE

(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole

(S)-3,3-DIPHENYL-1-METHYLTETRAHYDRO-1H,3H-PYRROLO[1,2-C][1,3,2]OXAZABOROLE

(S)-3,3-DIPHENYL-1-METHYLTETRAHYDRO-3H-PYRROLO-[1,2-C][1,3,2]OXAZABOROLE

(S)-ME CBS

(S)-METHYL OXAZABOROLIDINE

(S)-TETRAHYDRO-1-METHYL-3,3-DIPHENYL-1H,3H PYRROLO[1,2-C][1,3,2] OXAZABOROLE

(s)-methyl

(s)-methyloxazaborolidine,(s)-mecbs,in

(s)-methyloxazaborolidine,(s)-mecbs,intoluene

(S)-Methyloxazaborolidine,1-1.5Mintoluene[(S)-MeCBS]

(S)-Tetrahydro-1-Methyl-3

0.9-1.1Mintoluene[(S)-Methyloxazaborolidine]CoreyCatalyst