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151076

9-Borabicyclo[3.3.1]nonane solution

0.5 M in THF

Synonym(s):

9-BBN

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100 mL

Available to ship TODAYfromMILWAUKEE

$102.00
4 x 25 mL

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$103.00
800 mL

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$491.00
8 L

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$2,450.00
18 L

Estimated to ship onJune 29, 2026fromMILWAUKEE

$4,000.00

About This Item

Empirical Formula (Hill Notation):
C8H15B
CAS Number:
Molecular Weight:
122.02
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
605509

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form

liquid

Quality Level

reaction suitability

reagent type: reductant

concentration

0.5 M in THF

density

0.894 g/mL at 25 °C

SMILES string

B1C2CCCC1CCC2

InChI

1S/C8H15B/c1-3-7-5-2-6-8(4-1)9-7/h7-9H,1-6H2/t7-,8+

InChI key

FEJUGLKDZJDVFY-OCAPTIKFSA-N

General description

9-Borabicyclo[3.3.1]nonane is an organic compound, which is generally used as a hydroborating agent. It is thermally stable, less sensitive to oxygen and water when compared to other dialkyl boranes. It is commonly used to prepare aldehydes from alkynes.

Application

Differentiation of symmetrical diols by reduction of the corresponding cyclic acetals with 9-BBN.
Protecting group for alkenes†

Reactant for:
  • Linear SPPS synthesis of ubiquitin derivatives
  • Copper-catalyzed cross-coupling reactions of organoboron compounds with primary alkyl halides and pseudohalides
  • Intramolecular insertion of alkenes into palladium-nitrogen bonds
  • Preparation of (phosphonoacetyl)ornithine to study effect on arginine biosynthetic genes in yeast
  • Hetero-Diels-Alder reaction for synthesis of spirocyclic alkaloids
Selective hydroboration reduction reagent.[1]

Packaging

The 25 mL Sure/Seal bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

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This Item
459496176192178713
reaction suitability

reagent type: reductant

reaction suitability

reagent type: reductant

reaction suitability

reagent type: reductant

reaction suitability

reagent type: reductant

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

100

concentration

0.5 M in THF

concentration

0.4 M in hexanes

concentration

1.0 M in THF

concentration

-

density

0.894 g/mL at 25 °C

density

0.691 g/mL at 25 °C

density

0.898 g/mL at 25 °C

density

-

form

liquid

form

-

form

-

form

solid


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signalword

Danger

target_organs

Central nervous system, Respiratory system

supp_hazards

Storage Class

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

flash_point_f

1.0 °F - closed cup

flash_point_c

-17.2 °C - closed cup

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - STOT SE 3 - Water-react. 1



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Articles

Tandem hydroboration Suzuki Coupling both intermolecular and intramolecular gave diverse alkyl substituted products dppf


Preparation and properties
Hydroboration and Organic Synthesis: 9-Borabicyclo [3.3.1] nonane (9-BBN) (2007)
Zhishan Bo et al.
Organic letters, 6(5), 667-669 (2004-02-28)
Several useful aryl/alkyl building blocks for dendrimer and hyperbranched polymer synthesis were prepared by Suzuki-Miyaura cross-coupling reactions and iododesilylation reactions. The iododesilylations were carried out with iodine monochloride (ICl) in methylene chloride and diethyl ether (10:1). This solvent combination lowered
Chemistry Letters (Jpn), 33, 396-397 (2004)



Global Trade Item Number

SKUGTIN
151076-18L-KL04061838125095
151076-100ML04061838739001
151076-4X25ML04061838739018
151076-8L04061838125101
151076-800ML04061838739025

Questions

1–3 of 3 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. Can you please share the method on how you determine the hydrogen evolution to check the molarity of 9-BBN in THF.

    1 answer
    1. This product is only MQ100 quality level, which means details on the QC methods cannot be shared. For more information on our M-Clarity program, please see: https://www.sigmaaldrich.com//life-science/quality-and-regulatory-management/m-clarity-program

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