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178713

Sigma-Aldrich

9-Borabicyclo[3.3.1]nonane dimer

Synonym(s):

9-BBN

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About This Item

Empirical Formula (Hill Notation):
C16H30B2
CAS Number:
21205-91-4
Molecular Weight:
244.03
Beilstein/REAXYS Number:
605509
MDL number:
MFCD00168069
UNSPSC Code:
12352005
PubChem Substance ID:
24850763
NACRES:
NA.22

form

solid

Quality Level

100

reaction suitability

reagent type: reductant

mp

150-152 °C (lit.)

SMILES string

C1C[C@H]2CCC[C@@H](C1)B2B3[C@H]4CCC[C@@H]3CCC4

InChI

1S/C16H28B2/c1-5-13-7-2-8-14(6-1)17(13)18-15-9-3-10-16(18)12-4-11-15/h13-16H,1-12H2/t13-,14+,15-,16+

InChI key

IYDIZBOKVLHCQZ-GEEKYZPCSA-N

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Application

Air-stable, crystalline reagent used to reductively cleave cyclic acetals and ketals to monobenzylated 1,2-diols.
Employed in the hydroboration of alkynes, nitriles, and ketones.
Reagent found to reduce peroxo esters to alcohols without concomitant reduction of the peroxo linkage.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Flam. Sol. 1 - Skin Irrit. 2 - STOT SE 3 - Water-react 2

supp_hazards

EUH014

Storage Class

4.3 - Hazardous materials which set free flammable gases upon contact with water

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
SHBK2894
SHBJ4957
SHBJ1292
SHBJ0586
SHBH7096

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Hong-Xia Jin et al.
The Journal of organic chemistry, 70(11), 4240-4247 (2005-05-21)
Reduction of organic molecules that contain a peroxy bond is broadly considered as a "risky" and uncertain operation when cleavage of the peroxy linkage is not desired. For this reason, such reduction steps are normally avoided at the planning stage
Tetrahedron Letters, 32, 6239-6239 (1991)
Chemische Berichte, 126, 285-285 (1993)
Synlett, 349-349 (1991)
Organic Process Research & Development, 10, 1076-1076 (2006)

Articles

Reagents for C–C Bond Formation

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