280-64-8

Basic information

• Product Name: 9-Borabicyclo[3.3.1]nonane
• Synonyms: 9-BBN,9-BORABICYCLO[3.3.1]NONANE;9-BORABICYCLO[3.3.1]NONANE (9BBN);9-BBN(0.5M in toluene);9-Borabicyclo[3.3.1]nonane0.5M solution in THFAcroSeal§3;1,5-(Boranediyl)cyclooctane;9-Borabicyclo[3.3.1]nonane, 0.5M solution inHexane;9-Borabicyclo[3.3.1]nonane, crystalline,98%;9-Borabicyclo[3.3.1]nonane solution, 0.5 M in tetrahydrofuran
• CAS NO: 280-64-8
• Molecular Formula: C₈H₁₅B
• Molecular Weight: 122.02
• EINECS: 206-000-9
• Mol File: 280-64-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 140-142 °C
• Boiling Point: 68-70 °C
• Flash Point: 1 °F
• Appearance: white crystalline powder
• Density: 0.894 g/mL at 25 °C
• Storage Temp.: Flammables area
• Solubility: Miscible with ether, hexane, benzene, toluene, carbon tetrachlor
• Water Solubility: reacts
• Sensitive: Air & Moisture Sensitive
• BRN: 605509
• CAS DataBase Reference: 9-Borabicyclo[3.3.1]nonane(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Borabicyclo[3.3.1]nonane(280-64-8)
• EPA Substance Registry System: 9-Borabicyclo[3.3.1]nonane(280-64-8)

Safety Data

• Hazard Codes: F,Xn,Xi,N
• Statements: 14-20/21/22-36/37/38-36/37-19-14/15-11-67-65-62-51/53-48/20-38-40
• Safety Statements: 16-26-36/37/39-45-43-33-62-61-36/37-29-7/8-37/39
• RIDADR: UN 3399 4.3/PG 1
• WGK Germany: 3
• F: 1-10-34
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 280-64-8(Hazardous Substances Data)

Usage

Chemical Properties

WHITE CRYSTALLINE POWDER

Uses

Different sources of media describe the Uses of 280-64-8 differently. You can refer to the following data:
1. 9-BBN monomer acts as a selective hydroboration reagent in synthetic organic chemistry. It is employed in Suzuki reactions as well as in the preparation of terminal alcohols by the region selective addition of alkenes followed by oxidative cleavage using hydrogen peroxide. It is also used in copper-catalyzed cross-coupling reactions of organoboron compounds with primary alkyl halides and pseudohalides. It acts as a protecting group for alkenes. Further, it is used as a reactant for Hetero-Diels-Alder reaction for the synthesis of spirocyclic alkaloids. In addition to this, it is used in intramolecular insertion of alkenes into palladium-nitrogen bonds.
2. Protecting group for alkenes?Reactant for: Linear SPPS synthesis of ubiquitin derivativesCopper-catalyzed cross-coupling reactions of organoboron compounds with primary alkyl halides and pseudohalidesIntramolecular insertion of alkenes into palladium-nitrogen bondsPreparation of (phosphonoacetyl)ornithine to study effect on arginine biosynthetic genes in yeastHetero-Diels-Alder reaction for synthesis of spirocyclic alkaloids

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.

Purification Methods

It is available as the solid dimer or in tetrahydrofuran solution. The solid is relatively stable and can be purified by distillation in a vacuum (as dimer) and by recrystallisation from tetrahydrofuran (solubility at room temperature is 9.5%, 0.78M), filter off the solid under N2, wash it with dry pentane and dry it in vacuo at ca 100o. The solid is a dimer (IR 1567cm-1), stable in air (for ca 2 months), and can be heated for 24hours at 200o in an inert atmosphere without loss of hydride activity. It is a dimer in tetrahydrofuran solution also (IR 1567cm-1). It is sensitive to H2O and air (O2) in solution. Its concentration in solution can be determined by reaction with MeOH and measuring the volume of H2 liberated, or it can be oxidised to cis-cyclooctane-1,5-diol (m 73.5-74.5o). [IR: Knights & Brown J Am Chem Soc 90 5280 1968, Brown et al. J Am Chem Soc 96 7765 1974, Brown et al. J Org Chem 41 1778 1976, Brown & Chen J Org Chem 46 3978 1981, Fieser & Fieser Reagents for Org Synth 2 31, 3 24, 10 48, 15 43, 17, 49.] Borane pyridine complex [110 -51 -0] M 92.9, m 8-10o, 10-11o, b 86o/7mm, 100-1 0 1o/12mm, d 4 0.785. Dissolve it in Et2O and wash it with H2O in which it is insoluble. Evaporate the Et2O and distil the residual oil to gives better than 99.8% purity. Its vapour pressure is less than 0.1mm at room temperature. [Taylor et al. J Am Chem Soc 77 1506 1955, Beilstein 20 IV 2235.]

InChI:InChI=1/C8H14B/c1-3-7-5-2-6-8(4-1)9-7/h7-8H,1-6H2

Synthetic route

1,5-cis,cis-cyclooctadiene (1552-12-1, 111-78-4) → 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
With borane N-ethyl-N-isopropylaniline complex In 1,4-dioxane hydroboration; Heating;	87%
With dimethylsulfide borane complex In tetrahydrofuran at -5 - 67℃; for 1.75h;

borane-THF (14044-65-6) + 9-(di-tert-butylphosphanyl)-9-bora{3.3.1}bicyclononane (149468-33-7) → μ-(di-tert-butylphosphanyl)-diborane (149075-30-9) + 1,1,3,3-tetra-tert-butyl-1,3,2,4-diphosphadiboracyclobutane (149075-28-5) + μ-(di-tert-butylphosphanyl)-di-9-bora{3.3.1}bicyclononane (149075-29-6) + 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
In tetrahydrofuran dropping soln. of BH3*THF in THF to soln. of borane in THF at -78°C, under N2 or Ar; refluxing for 1 h; mechansim discussed;; removal of solvent in vac.; recrystn. from ether; 1. and 2. fraction product mixts., 3. fraction pure 9-borabicyclo(3.3.1)nonane, 4. fraction small amt. of pure (BH2P(tert-butyl)2)2; detn. by NMR;;	A n/a B n/a C n/a D 75%

((CH3)2CH)2NCH2CH(CH3)2*BH3 + 1,5-dicyclooctadiene (5259-72-3, 10060-40-9, 111-78-4) → 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
In 1,4-dioxane N2-atmosphere; dropwise cyclooctadiene addn. (20°C, stirring), stirring (room temp, 3 h, refluxing , 2 h); crystn. (room temp.), decanting, washing (n-pentane), drying (reduced pressure), recrystn. (THF);	70%

1,5-cis,cis-cyclooctadiene (1552-12-1, 111-78-4) → 9-BBN (38895-05-5) + 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
With borane N-ethyl-N-isopropylaniline complex In 1,4-dioxane at 20℃; for 1h; hydroboration; Title compound not separated from byproducts;

9-chloro-9-borabicyclo{3.3.1}nonane (22086-34-6) + 1-lithio-2,4,6-trimethylborazine → 9-N3B3H2(CH3)3-9-borabicyclo [2.2.1]nonane + 9-methyl-9-borabicyclo[3.3.1]nonane (23418-81-7) + 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
In diethyl ether; toluene Title compound not separated from byproducts.;

9-borabicyclo[3.3.1]nonane dimer (21205-91-4) → 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
With acetophenone In tetrahydrofuran Kinetics; 25°C; detected by IR;
With pivalaldehyde In tetrahydrofuran Kinetics; 25°C; detected by IR;
With 2,4-dimethylpentan-3-one In tetrahydrofuran Kinetics; 25°C; detected by IR;

C8H14BBrS(CH3)2 (70160-59-7) → 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
With Li(t-BuO)3AlH In tetrahydrofuran byproducts: B-alkoxy-9-borabicyclo-[3.3.1]nonane; 0°C, 0.25 h; detected by 11B NMR;
With LiAlH4 In tetrahydrofuran byproducts: AlBr3, LiBr; 0.25 equivalent LiAlH4, 0°C, 0.25 h; detected by 11B NMR;

lithium borohydride + C8H14BBrS(CH3)2 (70160-59-7) → dimethylsulfide borane complex (13292-87-0) + 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
In tetrahydrofuran byproducts: LiBr; 0°C, 0.25 h; detected by 11B NMR;

potassium tri(isopropoxy)borohydride + C8H14BBrS(CH3)2 (70160-59-7) → Triisopropyl borate (5419-55-6) + 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
In tetrahydrofuran byproducts: B-alkoxy-9-borabicyclo[3.3.1]nonane, KBr; 1 equivalent K(i-PrO)3BH, 25°C, 8.0 h; detected by 11B NMR;
In tetrahydrofuran byproducts: B-alkoxy-9-borabicyclo[3.3.1]nonane, KBr; 1 equivalent K(i-PrO)3BH, 0°C, 0.25 h; detected by 11B NMR;

lithium-9-borabicyclo[3.3.1]nonane hydride + C8H14BBrS(CH3)2 (70160-59-7) → 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
In tetrahydrofuran 0°C, 0.25 h; detected by 11B NMR;

C8H14BClS(CH3)2 (70160-58-6) → 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
With Li(CH3O)3AlH In tetrahydrofuran byproducts: B-alkoxy-9-borabicyclo[3.3.1]nonane; 0°C, 0.25 h; detected by 11B NMR;
With LiAlH4 In tetrahydrofuran byproducts: AlCl3, LiCl; 0.25 equivalent LiAlH4, 0°C, 0.25 h; detected by 11B NMR;

C8H14BClS(CH3)2 (70160-58-6) + lithium triethylborohydride (22560-16-3) → lithium-9-borabicyclo[3.3.1]nonane hydride + 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
In tetrahydrofuran byproducts: B-alkoxy-9-borabicyclo[3.3.1]nonane, (C2H5)3B; 0°C, 0.25 h; detected by 11B NMR;

lithium borohydride + C8H14BClS(CH3)2 (70160-58-6) → 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
In tetrahydrofuran byproducts: LiCl, BH3S(CH3)2; 0°C, 0.25 h; detected by 11B NMR;

sodium tetrahydroborate (16940-66-2) + C8H14BClS(CH3)2 (70160-58-6) → 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
In diethylene glycol dimethyl ether byproducts: NaCl, BH3S(CH3)2; 25°C, 0.25 h; detected by 11B NMR;

potassium tri(isopropoxy)borohydride + C8H14BClS(CH3)2 (70160-58-6) → Triisopropyl borate (5419-55-6) + 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
In tetrahydrofuran byproducts: B-alkoxy-9-borabicyclo-[3.3.1]nonane, KCl; 1 equivalent K(i-PrO)3BH, 0°C, 0.25 h; detected by 11B NMR;

lithium-9-borabicyclo[3.3.1]nonane hydride + C8H14BClS(CH3)2 (70160-58-6) → 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
In tetrahydrofuran 0°C, 0.25 h; detected by 11B NMR;

tetrakis(dimethylamido)zirconium (IV) (19756-04-8) + [C8BH14]2C10H6(NH)2 (187403-06-1) → C8BH14C10H6(NH)2Zr[N(CH3)2]3 + 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
In not given byproducts: (CH3)2N;

tetrakis(dimethylamido)titanium(IV) + [C8BH14]2C10H6(NH)2 (187403-06-1) → C8BH14C10H6(NH)2Ti[N(CH3)2]3 + 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
In not given byproducts: (CH3)2N;

dimethylsulfide borane complex (13292-87-0) + 1,5-dicyclooctadiene (5259-72-3, 10060-40-9, 111-78-4) → 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
In 1,2-dimethoxyethane at 20 - 60℃;

C26H47BNiO2P2 (1378876-25-5) → (iPrPOCOP)NiH (1108747-39-2) + 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
In (2)H8-toluene at 22℃; Equilibrium constant;

9-borabicyclo[3.3.1]nonane dimer (21205-91-4) + fluorocyclohexane (372-46-3) → B-cyclohexyl-9-borabicyclo<3.3.1>nonane (53535-83-4) + 9-fluoro-9-boracyclo{3.3.1}nonane (22086-35-7) + 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
In dichloromethane-d2 for 24h; Inert atmosphere; Glovebox; Sealed tube;

1,5-Hexadien (592-42-7) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → 9,9'-hexane-1,6-diyl-bis-9-bora-bicyclo[3.3.1]nonane (88703-69-9)

Conditions	Yield
In tetrahydrofuran at 40℃; for 24h; Schlenk technique; Inert atmosphere;	100%
In tetrahydrofuran at 20℃; for 3h; Addition;
In tetrahydrofuran at 20℃; for 4.5h; Addition; Hydroboration;
In tetrahydrofuran at 20℃; for 3h;

9-bora-bicyclo[3.3.1]nonane (280-64-8) + 2-amino-1-benzylamine (4403-69-4) → (2-aminomethyl-phenyl)-(9-bora-bicyclo[3.3.1]non-9-yl)-amine

Conditions	Yield
In tetrahydrofuran at 20℃;	100%
In tetrahydrofuran; hexane Yield given;

9-bora-bicyclo[3.3.1]nonane (280-64-8) → C8H15B*H(1-)*K(1+)

Conditions	Yield
With KH activated aith LiAlH4 In tetrahydrofuran at 25℃; for 0.5h;	100%

2-Aminobenzyl alcohol (5344-90-1) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → C15H21BNO(1-)*H(1+)

Conditions	Yield
In tetrahydrofuran; hexane at 20℃;	100%

2-Hydroxybenzylamine (932-30-9) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → C15H21BNO(1-)*H(1+)

Conditions	Yield
In tetrahydrofuran; hexane at 20℃;	100%

9-bora-bicyclo[3.3.1]nonane (280-64-8) + propan-1-ol-3-amine (156-87-6) → C11H21BNO(1-)*H(1+)

Conditions	Yield
In tetrahydrofuran; hexane at 20℃;	100%

1-hexene (592-41-6) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → 9-hexyl-9-borabicyclo[3.3.1]nonane (42371-64-2)

Conditions	Yield
In tetrahydrofuran at 60℃; for 12h; Schlenk technique; Inert atmosphere;	100%
In tetrahydrofuran at 25℃; for 24h; Schlenk technique; Inert atmosphere;	100%
In tetrahydrofuran at 20℃; for 2h;	87%

2,5-diallylpyrrole (42159-33-1) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → 2,5-bis-[3'-(9''-borabicyclo[3.3.1]nonyl)propyl]pyrrole (206867-77-8)

Conditions	Yield
In tetrahydrofuran N2-atmosphere; dropwise addn. of 2 equiv. of B-compd. to pyrrole derivative, stirring (room temp., 15 h); solvent removal (vac.), distn.;	100%

7a-aza-7,7-dimethyl-6,7-dihydro-7-stanna-7aH-indene (191797-28-1) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → N-borabicyclo[3.3.1]nonyl-2(prop-(Z)-1-enyl-3'-dimethylstannyl)pyrrole (191797-33-8)

Conditions	Yield
In tetrahydrofuran N2-atmosphere; stirring equimolar amts. (room temp., 15 h); solvent removal;	100%

ethynyl[dimethyl(vinyl)silylethynyl]dimethylsilane (1236226-20-2) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → 4-(9-borabicyclo[3.3.1]non-9-yl)-1,1,6,6-tetramethyl-1H,2H,3H,6H-1,6-disilapentalene (1236226-31-5)

Conditions	Yield
at 90 - 110℃; Inert atmosphere; regioselective reaction;	100%
In toluene (Ar), soln. of silane in toluene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.);
In benzene (Ar), soln. of silane in benzene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.);

1-(3-dimethylamino)propynyl[dimethyl(vinyl)silylethynyl]dimethylsilane (1236226-22-4) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → 4-(9-borabicyclo[3.3.1]non-9-yl)-5-[(dimethylamino)methyl]-1,1,6,6-tetramethyl-1H,2H,3H,6H-1,6-disilapentalene (1236226-33-7)

Conditions	Yield
at 90 - 110℃; Inert atmosphere; regioselective reaction;	100%
In toluene (Ar), soln. of silane in toluene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.); elem. anal.;
In benzene (Ar), soln. of silane in benzene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.); elem. anal.;

dimethyl(vinyl)silylethynyl(phenylethynyl)dimethylsilane (1236226-21-3) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → 4-(9-borabicyclo[3.3.1]non-9-yl)-1,1,6,6-tetramethyl-5-phenyl-1H,2H,3H,6H-1,6-disilapentalene (1236226-32-6)

Conditions	Yield
at 90 - 110℃; Inert atmosphere; regioselective reaction;	100%
In toluene (Ar), soln. of silane in toluene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.);
In benzene (Ar), soln. of silane in benzene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.);

(dimethyl(vinyl)silylethynyl)(dimethysilylethynyl)dimethylsilane (1236226-23-5) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → 4-(9-borabicyclo[3.3.1]non-9-yl)-5-(dimethylsilyl)-1,1,6,6-tetramethyl-1H,2H,3H,6H-1,6-disilapentalene (1236226-34-8)

Conditions	Yield
at 90 - 110℃; Inert atmosphere; regioselective reaction;	100%
In toluene (Ar), soln. of silane in toluene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.);
In benzene (Ar), soln. of silane in benzene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.);

bromodimethylsilylethynyl[dimethyl(vinyl)silylethynyl]dimethylsilane (1236226-24-6) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → 4-(9-borabicyclo[3.3.1]non-9-yl)-5-(bromodimethylsilyl)-1,1,6,6-tetramethyl-1H,2H,3H,6H-1,6-disilapentalene (1236226-35-9)

Conditions	Yield
at 90 - 110℃; Inert atmosphere; regioselective reaction;	100%
In toluene (Ar), soln. of silane in toluene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.);
In benzene (Ar), soln. of silane in benzene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.);

trimethylsilylethynyl[methyl(phenyl)(vinyl)silylethynyl]dimethylsilane (1236226-26-8) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → 4-(9-borabicyclo[3.3.1]non-9-yl)-1,6,6-trimethyl-1-phenyl-5-(trimethylsilyl)-1H,2H,3H,6H-1,6-disilapentalene (1236226-37-1)

Conditions	Yield
at 90 - 110℃; Inert atmosphere; regioselective reaction;	100%
In toluene (Ar), soln. of silane in toluene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.);
In benzene (Ar), soln. of silane in benzene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.);

bromodimethylsilylethynyl[diphenyl(vinyl)silylethynyl]dimethylsilane (1236226-25-7) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → 4-(9-borabicyclo[3.3.1]non-9-yl)-5-(bromodimethylsilyl)-6,6-dimethyl-1,1-diphenyl-1H,2H,3H,6H-1,6-disilapentalene (1236226-36-0)

Conditions	Yield
at 90 - 110℃; Inert atmosphere; regioselective reaction;	100%
In toluene (Ar), soln. of silane in toluene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.);
In benzene (Ar), soln. of silane in benzene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.);

triphenylsilylethynyl[methyl(phenyl)(vinyl)silylethynyl]dimethylsilane (1236226-27-9) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → 4-(9-borabicyclo[3.3.1]non-9-yl)-1,6,6-trimethyl-1-phenyl-5-(triphenylsilyl)-1H,2H,3H,6H-1,6-disilapentalene (1236226-38-2)

Conditions	Yield
at 90 - 110℃; Inert atmosphere; regioselective reaction;	100%
In toluene (Ar), soln. of silane in toluene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.);
In benzene (Ar), soln. of silane in benzene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.);

dmap (1122-58-3) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → C15H25BN2 (1283232-82-5)

Conditions	Yield
In dichloromethane at 20℃; Inert atmosphere;	100%

(4R)-5-(tert-butyldiphenylsilyloxy)-4-methyl-1-pentene (144693-95-8) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → C30H45BOSi

Conditions	Yield
In tetrahydrofuran at 20℃; Inert atmosphere;	100%

C23H39BSi (1578266-74-6) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → C31H54B2Si (1578266-79-1)

Conditions	Yield
In benzene-d6 at 80 - 100℃; for 0.666667h; Inert atmosphere;	100%

carbon dioxide (124-38-9) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → 9-methoxy-9-BBN (38050-71-4)

Conditions	Yield
With 1,3-di-tert-butylimidazol-2-ylidene In tetrahydrofuran at 70℃; under 750.075 - 2250.23 Torr; for 0.2h; Solvent; Temperature; Reagent/catalyst; Inert atmosphere; Glovebox; Sealed tube;	100%
With 1-dimesitylboryl-1’-diphenylphosphino-ferrocene In tetrahydrofuran-d8 at 70℃; under 750.075 Torr; for 20h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Inert atmosphere; Schlenk technique; Sealed tube;
With C9H18ClN3Si In tetrahydrofuran at 20℃; under 760.051 Torr; for 23h; Catalytic behavior; Mechanism; Reagent/catalyst; Time; Solvent;	100 %Spectr.

trimethylamine-N-oxide (1184-78-7) + 4-methyl-N-(2-propenyl)benzenesulfonamide (50487-71-3) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → N-(3-((1s,5s)-9-oxa-10-borabicyclo[3.3.2]decan-10-yl)propyl)-4-methylbenzenesulfonamide

Conditions	Yield
Stage #1: 4-methyl-N-(2-propenyl)benzenesulfonamide; 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 0 - 20℃; Stage #2: trimethylamine-N-oxide In tetrahydrofuran; dichloromethane	100%

trimethylamine-N-oxide (1184-78-7) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) + cyclohexene (110-83-8) → (1s,5s)-10-cyclohexyl-9-oxa-10-borabicyclo[3.3.2]decane

Conditions	Yield
Stage #1: 9-bora-bicyclo[3.3.1]nonane; cyclohexene In tetrahydrofuran at 0 - 20℃; Stage #2: trimethylamine-N-oxide In tetrahydrofuran; dichloromethane	100%

trimethylamine-N-oxide (1184-78-7) + 4-(allyloxy)-1-benzylpiperidine + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → 4-(3-((1s,5s)-9-oxa-10-borabicyclo[3.3.2]decan-10-yl)propoxy)-1-benzylpiperidine

Conditions	Yield
Stage #1: 4-(allyloxy)-1-benzylpiperidine; 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 0 - 20℃; Stage #2: trimethylamine-N-oxide In tetrahydrofuran; dichloromethane	100%

trimethylamine-N-oxide (1184-78-7) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) + 1-allyl-1H-pyrrolo[2,3-b]pyridine → 1-(3-((1s,5s)-9-oxa-10-borabicyclo[3.3.2]decan-10-yl)propyl)-1H-pyrrolo[2,3-b]pyridine

Conditions	Yield
Stage #1: 9-bora-bicyclo[3.3.1]nonane; 1-allyl-1H-pyrrolo[2,3-b]pyridine In tetrahydrofuran at 0 - 20℃; Stage #2: trimethylamine-N-oxide In tetrahydrofuran; dichloromethane	100%

C17H19N5(2+)*2C24H20B(1-) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → C33H49B2N5(2+)*2C24H20B(1-)

Conditions	Yield
In dichloromethane at 45℃; for 24h; Schlenk technique; Inert atmosphere;	100%

C19H17FeN5O2 + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → C35H47B2FeN5O2

Conditions	Yield
In tetrahydrofuran for 16h;	100%

N-allyl-N,N-dimethyl-N-butylammonium chloride + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → C17H35BN(1+)*Cl(1-)

Conditions	Yield
In tetrahydrofuran at 60℃; for 12h; Schlenk technique; Inert atmosphere;	100%
In tetrahydrofuran at 20℃; for 6h; Glovebox;	95%

N,N,N-triethylpent-4-en-1-aminium iodide + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → C19H39BN(1+)*I(1-)

Conditions	Yield
In tetrahydrofuran at 60℃; for 12h; Schlenk technique; Inert atmosphere;	100%

N,N,N-triethylhex-5-en-1-aminium bromide + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → C20H41BN(1+)*Br(1-)

Conditions	Yield
In tetrahydrofuran at 60℃; for 12h; Schlenk technique; Inert atmosphere;	100%

Upstream product

• 5259-72-3 cyclo-octa-1,5-diene 
• 14044-65-6 borane-THF 
• 149468-33-7 9-(di-tert-butylphosphanyl)-9-bora{3.3.1}bicyclononane 
• 19756-04-8 tetrakis(dimethylamido)zirconium (IV) 
• 187403-06-1 [C₈BH₁₄]2C₁₀H₆(NH)2 
• 38050-71-4 9-methoxy-9-borabicyclo[3.3.1]nonane 
• 21205-91-4 9-borabicyclo[3.3.1]nonane dimer 
• 372-46-3 fluorocyclohexane 
• 13292-87-0 dimethylsulfide borane complex 
• 70160-58-6 C₈H₁₄BClS(CH₃)2 
• 16940-66-2 sodium tetrahydroborate 
• 22560-16-3 lithium triethylborohydride 
• 70160-59-7 C₈H₁₄BBrS(CH₃)2 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 

Downstream Products

• 38050-71-4 9-methoxy-9-borabicyclo[3.3.1]nonane 
• 61967-15-5 9-cyclohex-2-enyl-9-bora-bicyclo[3.3.1]nonane 
• 23418-91-9 9-phenyl-9-borabicyclo[3.3.1]nonane 
• 23418-90-8 9-p-tolyl-9-bora-bicyclo[3.3.1]nonane 
• 23418-90-8 B-p-tolyl-9-borabicyclo[3.3.1]nonane 
• 22086-45-9 9-bromo-9-bora-bicyclo[3.3.1]nonane 
• 70145-42-5 B-iodo-9-BBN 
• 873297-68-8 9-(3-benzyloxy-propyl)-9-bora-bicyclo[3.3.1]nonane 
• 7559-34-4 2,4-dimethyl-6-propyl-s-triazine 
• 30362-06-2 2,4-dimethyl-6-(2-methylpropyl)-s-triazine 
• 442200-16-0 (4R,5S,6S)-4-Benzyloxymethyl-6-[(S)-2-(9-bora-bicyclo[3.3.1]non-9-yl)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxane 

Relevant articles and documents

A novel diaminoborate ligand system derived from 1,8-diaminonaphthalene and 9-BBN: Preparation of titanium and zirconium complexes and crystal structure of the titanium complex

1,8-Diaminonaphthalene reacts selectively with 1 equiv. of 9-BBN to form a bridging amine-aminoborane, and with 2 equiv. of 9-BBN to form a non-bridging bis(aminoborane); these aminoboranes give rise to a novel diaminoborate (4e,1-) ligand system by reactions with dimethylamides of titanium and zirconium.

Interactions of C?F Bonds with Hydridoboranes: Reduction, Borylation and Friedel–Crafts Alkylation

The stoichiometric reactions of the alkylfluorides 1-fluoroadamantane (Ad-F), fluorocyclohexane (Cy-F), 1-fluoropentane (Pent-F) and benzyl fluorides with secondary boranes pinacolborane (HBpin), catecholborane (HBcat), 9-borabicyclo(3.3.1)nonane (9-BBN)

SALTS OF 2-FLUORO-N-METHYL-4-[7-(QUINOLIN-6-YL-METHYL)-IMIDAZO[1,2-b][1,2,4]TRIAZIN-2-YL]BENZAMIDE AND PROCESSES RELATED TO PREPARING THE SAME

The present invention is directed to dihydrochloric acid and dibenzenesulfonic acid salts of the c-Met kinase inhibitor 2-fluoro-N-methyl-4-[7-(quinolin-6-ylmethyl)-imidazo[1,2-b][1,2,4]triazin-2-yl]benzamide, and pharmaceutical compositions thereof, useful in the treatment of cancer and other diseases related to the dysregulation of kinase pathways. The present invention further relates to processes and intermediates for preparing 2-fluoro-N-methyl-4-[7-(quinolin-6-ylmethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzamide, and salts thereof.

A New Efficient Synthesis of (R,R)-2,2'-Bipyrrolidine: An Interesting Chiral 1,2-Diamine with C2 Symmetry

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