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Key Documents

COO/COA

676675

(+)-9-(1S, 2S-Pseudoephedrinyl)-(10R)-(trimethylsilyl)-9-borabicyclo[3.3.2]decane

Name: (+)-9-(1S, 2S-Pseudoephedrinyl)-(10R)-(trimethylsilyl)-9-borabicyclo[3.3.2]decane
Brand: ALDRICH

Synonym(s):

N,α-Dimethyl-β-[[(10R)-10-(trimethylsilyl)-9-borabicyclo[3.3.2]dec-9-yl]oxy]-(αS,βS)-benzeneethanamine

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About This Item

Empirical Formula (Hill Notation):

C₂₂H₃₈BNOSi

CAS Number:

848618-13-3

Molecular Weight:

371.44

MDL number:

MFCD09265094

UNSPSC Code:

12352000

PubChem Substance ID:

24885323

form

solid

optical activity

[α]22/D +60°, c = 4.5 in chloroform-d

mp

130-134 °C

SMILES string

CN[C@@H](C)[C@@H](OB1C2CCCC(CCC2)[C@@H]1[Si](C)(C)C)c3ccccc3

InChI

1S/C22H38BNOSi/c1-17(24-2)21(18-11-7-6-8-12-18)25-23-20-15-9-13-19(14-10-16-20)22(23)26(3,4)5/h6-8,11-12,17,19-22,24H,9-10,13-16H2,1-5H3/t17-,19-,20+,21+,22-/m0/s1

InChI key

ZOZYQBFBLCMBTA-RXZUFOQRSA-N

Application

Soderquist Reagents: For allylboration, allenylboration, propargylboration

Air-stable, crystalline pseudoephedrine borinic acid complex which when treated with an appropriate Grignard reagent provides access to homoallylic or homopropargylic alcohols and α-allenyl carbinols.

Pictograms

GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P261 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number

08127JE

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Nonracemic alpha-allenyl carbinols from asymmetric propargylation with the 10-trimethylsilyl-9-borabicyclo[3.3.2]decanes.

Eliud Hernandez et al.

Organic letters, 7(24), 5397-5400 (2005-11-18)

[reaction: see text] The asymmetric propargylboration of aldehydes at -78 degrees C in <3 h with 1 provides silylated alpha-allenyl carbinols 6 (60-87%) in high ee (94% to >98% ee). The reagents 1 are easily prepared in both enantiomeric forms

Nonracemic homopropargylic alcohols via asymmetric allenylboration with the robust and versatile 10-TMS-9-borabicyclo[3.3.2]decanes.

Chunqiu Lai et al.

Organic letters, 7(5), 799-802 (2005-02-25)

The asymmetric allenylboration of representative aldehydes with the stable, storable 1 is reported. Easily and efficiently prepared in either enantiomeric form from the air-stable crystalline 4 through simple Grignard procedures, 1 gives 6 cleanly. The latter is easily isolated in

Asymmetric allyl- and crotylboration with the robust, versatile, and recyclable 10-TMS-9-borabicyclo[3.3.2]decanes.

Carlos H Burgos et al.

Journal of the American Chemical Society, 127(22), 8044-8049 (2005-06-02)

The remarkable versatility and selectivity of the 10-(trimethylsilyl)-9-borabicyclo[3.3.2]decanes (10-TMS-9-BBDs) in the allyl- and crotylboration of representative aldehydes are reported. The new reagents are prepared through air-stable crystalline pseudoephedrine borinic ester complexes of the 10-TMS-9-BBDs (4), which are available in 63%

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