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Merck
모든 사진(2)

문서

151076

Sigma-Aldrich

9-Borabicyclo[3.3.1]nonane solution

0.5 M in THF

동의어(들):

9-BBN

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About This Item

실험식(Hill 표기법):
C8H15B
CAS Number:
Molecular Weight:
122.02
Beilstein:
605509
MDL number:
UNSPSC 코드:
12352005
PubChem Substance ID:
NACRES:
NA.22

형태

liquid

Quality Level

반응 적합성

reagent type: reductant

농도

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

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일반 설명

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.

애플리케이션

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
Differentiation of symmetrical diols by reduction of the corresponding cyclic acetals with 9-BBN.
Selective hydroboration reduction reagent.

포장

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

법적 정보

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

픽토그램

FlameHealth hazardExclamation mark

신호어

Danger

유해 및 위험 성명서

Hazard Classifications

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

표적 기관

Central nervous system, Respiratory system

보충제 위험성

Storage Class Code

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

WGK

WGK 3

Flash Point (°F)

1.0 °F - closed cup

Flash Point (°C)

-17.2 °C - closed cup


시험 성적서(COA)

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문서 라이브러리에서 최근에 구매한 제품에 대한 문서를 찾아보세요.

문서 라이브러리 방문

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)
9-Borabicyclo [3.3. 1] nonane as a convenient selective hydroborating agent
Knights EF and Brown HC
Journal of the American Chemical Society, 90(19), 5281-5283 (1968)
Organic Process Research & Development, 10, 1076-1076 (2006)

문서

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

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