9-borabicyclo (3.3.1) nonane

Structural formula
Crystal system	monoclinic (dimer)
Space group	C 2 / m (No. 12) (dimer)
Lattice parameters	a = 1454 pm ; b = 1549 pm ; c = 688 pm ; β = 92.7 ° (dimer)
General
Surname	9-borabicyclo [3.3.1] nonane
other names	9-BBN (monomer); (9-BBN) 2 (dimer); Bis-9-borabicyclo [3.3.1] nonane (dimer);
Molecular formula	C 8 H 15 B (monomer); C 16 H 30 B 2 (dimer);
External identifiers / databases
EC number	206-000-9
ECHA InfoCard	100.005.456
PubChem	78966
ChemSpider	71299
Wikidata	Q275023
properties
Molar mass	122.02 g mol −1 (monomer); 244.04 g mol −1 (dimer);
Physical state	firmly
Melting point	150-152 ° C
safety instructions
H and P phrases	H: 225-260-319-335
	P: 210-223-231 + 232-261-370 + 378-422
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

9-Borabicyclo [3.3.1] nonane , often abbreviated as 9-BBN , is an organoborane . The colorless solid is used in organic chemistry as a reagent for hydroboration .

presentation

9-BBN is produced by reacting 1,5-cyclooctadiene with borane complexes in ethereal solution (e.g. with tetrahydrofuran or dimethyl sulfide ).

properties

The compound is a dimer linked via the hydrogen atoms , which is easily cleaved in the presence of a reducible substrate. Like other organoboron compounds, 9-BBN is pyrophoric and is therefore mostly used as a solution in tetrahydrofuran .

As a solid, 9-BBN occurs exclusively as a dimer, also in certain organic solvents; however, there can also be an equilibrium between the dimeric and the (complexed with the solvent) monomeric form in solution.

Dimeric 9-borabicyclononane

use

In addition to hydroboration, 9-BBN can also be used in Suzuki reactions . Due to its high steric hindrance from the cyclooctyl substituent, 9-BBN leads almost exclusively to the anti-Markovnikov product in the hydroboration reaction compared to boranes .

Web links

Commons : 9-BBN - collection of pictures, videos and audio files

Individual evidence

↑ ^a ^b ^c D. J. Brauer, C. Krüger: The Crystal and Molecular Structure of Bis-9-borabicyclo [3,3,1] nonane: a Study of the Boron-Carbon Bond . In: Acta Cryst. (1973), B29, pp. 1684-1690; doi : 10.1107 / S0567740873005261 .
↑ Data sheet 9-BBN (PDF) from Fisher Scientific , accessed February 13, 2014.
↑ ^a ^b Data sheet 9-Borabicyclo [3.3.1] nonane solution 0.5 M in THF from Sigma-Aldrich , accessed on March 18, 2011 ( PDF ).
↑ John A. Soderquist, Herbert C. Brown : Simple, remarkably efficient route to high purity, crystalline 9-borabicyclo [3.3.1] nonane (9-BBN) dimer , J. Org. Chem. , 1981, 46, 22, Pp. 4599-4600, doi : 10.1021 / jo00335a067 .
↑ John A. Soderquist, Alvin Negron: 9-Borabicyclo [3.3.1] nonane, dimer Template: link text check / apostrophe In: Organic Syntheses . 70, 1992, p. 169, doi : 10.15227 / orgsyn.070.0169 ; Coll. Vol. 9, 1998, p. 95 ( PDF ).
^ HC Brown: Organic Syntheses via Boranes. John Wiley & Sons, Inc. New York 1975, ISBN 0-471-11280-1 .
↑ External identifiers or database links to 9-BBN (dimer) : CAS number: 21205-91-4, EC number: 629-228-4, ECHA InfoCard: 100.157.428 , PubChem : 16211404 , Wikidata : Q55961000 .
↑ Herbert C. Brown, Kung K. Wang, Charles G. Scouten: Hydroboration kinetics: Unusual kinetics for the reaction of 9-borabicyclo [3.3.1] nonane with representative alkenes ; Proc Natl Acad Sci USA, February 1980, 77 (2), pp. 698-702; Abstract .
↑ Tatsuo Ishiyama, Norio Miyaura, Akira Suzuki: Palladium (0) -catalyzed reaction of 9-alkyl-9-borabicyclo [3.3.1] nonane with 1-bromo-1-phenylthioethene: 4- (3-cyclohexenyl) -2- phenylthio-1-butene Template: link text check / apostrophe In: Organic Syntheses . 71, 1993, p. 89, doi : 10.15227 / orgsyn.071.0089 ; Coll. Vol. 9, 1998, p. 107 ( PDF ).

[BrauerKruger1973-1] D. J. Brauer, C. Krüger: The Crystal and Molecular Structure of Bis-9-borabicyclo [3,3,1] nonane: a Study of the Boron-Carbon Bond . In: Acta Cryst. (1973), B29, pp. 1684-1690; doi : 10.1107 / S0567740873005261 .

[2] Data sheet 9-BBN (PDF) from Fisher Scientific , accessed February 13, 2014.

[Sigma-3] Data sheet 9-Borabicyclo [3.3.1] nonane solution 0.5 M in THF from Sigma-Aldrich , accessed on March 18, 2011 ( PDF ).

[4] John A. Soderquist, Herbert C. Brown : Simple, remarkably efficient route to high purity, crystalline 9-borabicyclo [3.3.1] nonane (9-BBN) dimer , J. Org. Chem. , 1981, 46, 22, Pp. 4599-4600, doi : 10.1021 / jo00335a067 .

[5] John A. Soderquist, Alvin Negron: 9-Borabicyclo [3.3.1] nonane, dimer Template: link text check / apostrophe In: Organic Syntheses . 70, 1992, p. 169, doi : 10.15227 / orgsyn.070.0169 ; Coll. Vol. 9, 1998, p. 95 ( PDF ).

[6] HC Brown: Organic Syntheses via Boranes. John Wiley & Sons, Inc. New York 1975, ISBN 0-471-11280-1 .

[7] External identifiers or database links to 9-BBN (dimer) : CAS number: 21205-91-4, EC number: 629-228-4, ECHA InfoCard: 100.157.428 , PubChem : 16211404 , Wikidata : Q55961000 .

[Brown1980-8] Herbert C. Brown, Kung K. Wang, Charles G. Scouten: Hydroboration kinetics: Unusual kinetics for the reaction of 9-borabicyclo [3.3.1] nonane with representative alkenes ; Proc Natl Acad Sci USA, February 1980, 77 (2), pp. 698-702; Abstract .

[9] Tatsuo Ishiyama, Norio Miyaura, Akira Suzuki: Palladium (0) -catalyzed reaction of 9-alkyl-9-borabicyclo [3.3.1] nonane with 1-bromo-1-phenylthioethene: 4- (3-cyclohexenyl) -2- phenylthio-1-butene Template: link text check / apostrophe In: Organic Syntheses . 71, 1993, p. 89, doi : 10.15227 / orgsyn.071.0089 ; Coll. Vol. 9, 1998, p. 107 ( PDF ).