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178713

Sigma-Aldrich

9-Borabicyclo[3.3.1]nonane dimer

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Synonym(s):
9-BBN
Empirical Formula (Hill Notation):
C16H30B2
CAS Number:
Molecular Weight:
244.03
Beilstein/REAXYS Number:
605509
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

solid

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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1 of 4

This Item
74486713658133471
vibrant-m

178713

9-Borabicyclo[3.3.1]nonane dimer

vibrant-m

136581

1,5-Diazabicyclo[4.3.0]non-5-ene

vibrant-m

33471

1,5-Diazabicyclo[4.3.0]non-5-ene

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

form

solid

form

powder

form

liquid

form

liquid

mp

150-152 °C (lit.)

mp

-

mp

-

mp

-

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

signalword

Danger

Hazard Classifications

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

supp_hazards

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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Synlett, 349-349 (1991)
Chemische Berichte, 126, 285-285 (1993)
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)
Organic Process Research & Development, 10, 1076-1076 (2006)

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