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Alpine borane information


Alpine borane[1]
Skeletal formula of alpine borane
Ball-and-stick model of the alpine borane molecule
Names
IUPAC name
9-(2,6,6-Trimethylbicyclo[3.1.1]hept-3-yl)-9-bora-bicyclo[3.3.1]nonane
Other names
Alpine-Borane; B-Isopinocampheyl-9-borabicyclo[3.3.1]nonane; B-3-Pinanyl-9-borabicyclo[3.3.1]nonane
Identifiers
CAS Number
  • 73624-47-2 (R isomer) checkY
  • 42371-63-1 (S isomer) checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 17206399 checkY
ECHA InfoCard 100.157.575 Edit this at Wikidata
PubChem CID
  • 9921373 R
  • 10890567 S
CompTox Dashboard (EPA)
  • DTXSID50432857 Edit this at Wikidata
InChI
  • InChI=1S/C18H31B/c1-12-16-10-13(18(16,2)3)11-17(12)19-14-6-4-7-15(19)9-5-8-14/h12-17H,4-11H2,1-3H3/t12-,13-,14?,15?,16+,17-/m1/s1 checkY
    Key: VCDGSBJCRYTLNU-AZWGFFAPSA-N checkY
  • InChI=1/C18H31B/c1-12-16-10-13(18(16,2)3)11-17(12)19-14-6-4-7-15(19)9-5-8-14/h12-17H,4-11H2,1-3H3/t12-,13-,14?,15?,16+,17-/m1/s1
    Key: VCDGSBJCRYTLNU-AZWGFFAPBY
SMILES
  • CC4(C)[C@@H]1C[C@H]4[C@@H](C)[C@@H](C1)B3C2CCCC3CCC2
Properties
Chemical formula
 C18H31B
Molar mass 258.26 g·mol−1
Appearance Colorless liquid
Density 0.947 g/mL
Boiling point > 55 °C (131 °F; 328 K)
Hazards
GHS labelling:
Pictograms
 GHS02: Flammable
Signal word
 Danger
Hazard statements
 H250
Precautionary statements
 P210, P222, P280, P302+P334, P370+P378, P422
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Alpine borane is the commercial name for an organoboron compound that is used in organic synthesis. It is a colorless liquid, although it is usually encountered as a solution. A range of alkyl-substituted borane are specialty reagents in organic synthesis. Two such reagents that are closely related to Alpine borane are 9-BBN and diisopinocampheylborane.

  1. ^ R-Alpine-Borane and S-Alpine-Borane at Sigma-Aldrich

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Alpine borane

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Alpine borane is the commercial name for an organoboron compound that is used in organic synthesis. It is a colorless liquid, although it is usually encountered...

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Borylation

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the name Alpine Borane and the asymmetric reduction of carbonyl groups with either enantiomer of Alpine-Borane is known as Midland Alpine-Borane reduction...

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Pinene

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With borane-dimethylsulfide, two equivalents of α-pinene react to give (diisopinocampheyl)borane. Reaction with 9-BBN gives the reagent called alpine borane...

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Diisopinocampheylborane

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and the other the S, the enantioselectivity is typically very high. Alpine-borane is produced by hydroborating α-pinene with 9-borabicyclononane. Both...

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List of organic reactions

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Michael system Michael condensation Michaelis–Arbuzov reaction Midland Alpine borane reduction Mignonac reaction Milas hydroxylation of olefins Minisci reaction...

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Enantioselective reduction of ketones

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synthesize enantiopure alcohols by ketone reduction is the Midland Alpine borane reduction, named after its inventor Professor M. Mark Midland. The strategy...

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Galantamine total synthesis

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stereocenter and obtained by chiral synthesis of the ketone with R-Alpine borane) in a Mitsunobu reaction to aryl ether 4. The trimethylsilyl protective...

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