97-94-9

Usage

Chemical Description

Triethylborane and trimethylaluminum are organoboron and organoaluminum compounds, respectively, used as reagents.

Uses

Used in Organic Syntheses:
Triethylborane is used as a reagent in organic syntheses for its ability to act as a blocking agent and radical initiator. Its strong Lewis acid properties enable it to facilitate various chemical reactions, making it a valuable tool in the synthesis of complex organic molecules.
Used in Rocket Propulsion Systems:
In the aerospace industry, triethylborane is used in mixtures with triethylaluminum as hypergolic igniters in rocket propulsion systems. The combination of these two compounds results in a highly exothermic reaction, providing a rapid and efficient ignition source for rocket engines.
Used in the Synthesis of 8-Hydroxyquinolato Boron Compounds:
Triethylborane is also used in the synthesis of three 8-hydroxyquinolato (q) boron compounds, namely B(C2H5)3q (1), BPh2q (2), and B(2-napht)3q (3), by reacting with 8-hydroxyquinoline. These compounds have potential applications in various fields, such as materials science and pharmaceuticals, due to their unique chemical properties.
Chemical Properties:
Triethylborane is a clear colorless to light amber solution that is miscible with most organic solvents, making it suitable for use in a wide range of chemical reactions. However, it is immiscible with water, which is an important consideration when handling and storing the compound. Its strong Lewis acid properties and reducing capabilities contribute to its versatility as a reagent in various chemical processes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 427, 1986 DOI: 10.1021/jo00354a002

Hazard

Flammable, dangerous fire risk, ignites spontaneously in air. Reacts violently with water and oxidizing materials. Toxic by inhalation, strong irritant.

Health Hazard

Triethylboron is a toxic substance. The toxicsymptoms from chronic exposure to thiscompound are not reported. Skin contact canburn tissues.

Fire Hazard

Triethylborane is a pyrophoric substance, igniting spontaneously on exposure to air, chlorine, or bromine. Explosion may result when mixed with oxygen. Contact with ozone, peroxides and other oxidants can cause explosion. Its concentrated solutions can be pyrophoric. Flash point of 1 M solution in hexane is －23°C ( －9°F), while that in tetrahydrofuran is －17°C (1°F) (Aldrich 1996). It decomposes explosively when mixed with water.

Safety Profile

Poison by ingestion and intraperitoneal routes. Mildly toxic by inhalation. Animal experiments show that the vapor is a poison which causes pulmonary irritation and convulsions. A very dangerous fire hazard by spontaneous chemical reaction with oxichzers. Spontaneously flammable in air. Explodes in oxygen atmospheres. Hypergolic reaction with triethylaluminum. Ignites on contact with chlorine, bromine, or other halogens. Will react with water or steam to produce toxic and flammable vapors. To fight fire, do NOT use halogenated extinguishing agents. When heated to decomposition or upon contact with air it emits toxic acrid smoke and irritating fumes. See also BORANES and BORON COMPOUNDS.

Purification Methods

It distils at 56-57o/220mm. It can also be purified via its ammonia addition complex which is distilled in a high vacuum, decomposed with dry HCl, and the Et3B is distilled out. It is commercially available as a 15% solution in hexane or as 1M solution in hexane. [Brown J Am Chem Soc 67 376 1945, Bamford et al. J Chem Soc 471 1946, Lin et al. J Organomet Chem 312 277 1986, Beilstein 4 III 1957, 4 IV 4359.]

InChI:InChI=1/C6H15B/c1-4-7(5-2)6-3/h4-6H2,1-3H3

Synthetic route

ethyl bromide (74-96-4) + trifluoroborane diethyl ether (109-63-7) → triethyl borane (97-94-9)

Conditions	Yield
With magnesium In diethyl ether byproducts: MgFBr, EtMgBr; react. of EtBr, Mg turnings, and BF3*Et2O (in 3.5:3.5:1 molar ratio) in Et2O for 2 h; not isolated; detected by NMR;	100%

tetraethyldiborane + (phenylamino)diethylborane (22093-18-1) → 1-phenyl-2,5-diethyl-1,2,5-azadiborolane (96080-50-1) + triethyl borane (97-94-9)

Conditions	Yield
byproducts: hydrogene; High Pressure; 180°C 16 h and 200°C 9 h in autoclave shaking at 50 atm then 210-225°C 2 h; distn.;	A 97.6% B n/a
byproducts: hydrogene; High Pressure; 180°C 16 h and 200°C 9 h in autoclave shaking at 50 atm then 210-225°C 2 h; distn.;	A 97.6% B n/a

tetraethyldiboroxane (158817-73-3) → bis(diethylboryl)sulfate (158817-74-4) + triethyl borane (97-94-9)

Conditions	Yield
With SO3 In (2)H8-toluene under Ar, addn. of SO3 in (d8)-toluene to B-compd. in (d8)-toluene at 0°C, warmed to room temp.; detn. by (17)O-NMR;	A 95% B 5%

ethyl bromide (74-96-4) + triethyl borate (150-46-9) + aluminium (7429-90-5) → triethyl borane (97-94-9)

Conditions	Yield
In neat (no solvent) Sonication; N2; molar ratio EtBr:B(OEt)3:Al = 4.5:1:3.3, ultrasound treatment of EtBr and Al (-20°C), addn. of B(OEt)3 (room temp., during 10 min); distn.;	91.4%
With iodine In neat (no solvent) Sonication; N2; molar ratio EtBr:B(OEt)3:Al:I2 = 0.65:0.166:0.476:0.0025, ultrasound treatment of EtBr, Al and I2 (-20°C), addn. of B(OEt)3 (room temp., during 10 min); distn.;	90%
With iodine In neat (no solvent) Sonication; N2; molar ratio EtBr:B(OEt)3:Al:I2 = 0.65:0.166:0.476:0.005, ultrasoundtreatment of EtBr, Al and I2 (-20°C), addn. of B(OEt)3 (room temp., during 10 min); distn.;	90.3%

sulfur (10544-50-0) + sodium triethylborohydride → sodium sulfide + triethyl borane (97-94-9)

Conditions	Yield
In toluene byproducts: H2; Ar atmosphere, stirring (80-90°C, 8 h); washing (pentane), drying (0.1 Torr);	A 91% B n/a

ethene (74-85-1) + diborane (19287-45-7) → triethyl borane (97-94-9) + boron hydride (13766-26-2)

Conditions	Yield
In neat (no solvent) byproducts: H2; Irradiation (UV/VIS); react. of B2H6 with C2H4 (1:12) at 320 Torr and irradiation with cw CO2laser for 2 s;	A 91% B n/a
In neat (no solvent) byproducts: H2; Irradiation (UV/VIS); react. B2H6 with C2H4 (1:9) at 320 Torr and irradiation with cw CO2 laser for 2 s;	A 56% B n/a
In neat (no solvent) byproducts: H2; Irradiation (UV/VIS); react. B2H6 with C2H4 (1:6) at 160 Torr and irradiation with cw CO2 laser for 2 s;	A 34.5% B n/a

triethyl borate (150-46-9) + triethyl-alane; compound with diethyl ether (13824-25-4, 14002-28-9) → triethyl borane (97-94-9)

Conditions	Yield
In neat (no solvent) Sonication; (N2), Et3Al*Et2O introduced into a flask connected to a condenser containing alcohol at -20°C, stirred and heated to 120°C in an oil bath, added alkyl borate dropwise during 10 min, stirred for further20 min; distd.; gas chromy.;	90%

N,N′-di-tertbutyl(phenylamidinato)chlorosilylene + [(1,2-bis(dimethylphosphine)ethane)2(PMe3)Fe] (1430654-19-5) → triethyl borane (97-94-9) + C27H56FeN2P4Si (1430654-22-0)

Conditions	Yield
Stage #1: N,N′-di-tertbutyl(phenylamidinato)chlorosilylene; [(1,2-bis(dimethylphosphine)ethane)2(PMe3)Fe] In diethyl ether at -30 - 20℃; for 2h; Schlenk technique; Stage #2: With lithium triethylborohydride at 0 - 20℃; for 3.33333h; Schlenk technique;	A n/a B 89%

tetraethyldiborane(6) (12081-54-8) + indole (120-72-9) → (indolyl)diethylborane (28916-09-8) + triethyl borane (97-94-9)

Conditions	Yield
byproducts: H2; 90°C;	A 87% B n/a

diethylboron bromide (19162-10-8) + P-methyl-N,N'-bis(tert-butyl)diamidothiophosphonate (97536-05-5) → triethyl borane (97-94-9) + 1,3-di-tert-butyl-4-ethyl-2-methyl-1,3,2,4-diazaphosphaboretidine-2-sulfide (62948-90-7)

Conditions	Yield
With n-butyllithium In hexane N2 atmosphere; lithiation of amine with n-BuLi/hexane; refluxed for 20 h; addn. of a soln. of B compd. in hexane at -40°; slow warming to room temp.; filtration; fractional distn.; heating at 140°C for3 h in N2 stream with condensation;; fractional distn.; elem. anal.;;	A 85% B 82%

bis[tert-butyl(diethylboryl)amino]methylphosphanoxide (97536-02-2) → 1,3-di-tert-butyl-4-ethyl-2-methyl-1,3,2,4-diazaphosphaboretidine-2-oxide (97536-01-1) + triethyl borane (97-94-9)

Conditions	Yield
In neat (no solvent) heating at 170-190°C for 5 h in a stream of N2; condensation of volatiles in a cool trap;; distn.; elem. anal.;;	A 55% B 85%

diethylboron bromide (19162-10-8) + 1,2-bis(trimethylstannyl)benzene (14275-62-8) → triethyl borane (97-94-9) + 1,2-bis(diethylboryl)benzene (208246-80-4)

Conditions	Yield
In pentane byproducts: (CH3)3SnBr; inert atmosphere, addn. of soln. of stannyl compound to refluxing soln. of Et2BBr, reflux ( 1 h); removement of volatiles (vacuum), addn. (pentane), pptn. (-78°C),filtration of (CH3)3SnBr (-78°C), removement of solvent (vacuum) , distillation;	A n/a B 84%

boric acid tributyl ester (688-74-4) + triethylaluminum (97-93-8) → triethyl borane (97-94-9)

Conditions	Yield
In neat (no solvent) Sonication; (N2), Et3Al introduced into a flask connected to a condenser containingalcohol at -20°C, stirred and heated to 120°C in an oil bath, added alkyl borate dropwise during 10 min, stirred for further 20 min; distd.; gas chromy.;	82.3%

tri-n-propyl borate (688-71-1) + triethyl-alane; compound with diethyl ether (13824-25-4, 14002-28-9) → triethyl borane (97-94-9)

Conditions	Yield
In neat (no solvent) Sonication; (N2), Et3Al*Et2O introduced into a flask connected to a condenser containing alcohol at -20°C, stirred and heated to 120°C in an oil bath, added alkyl borate dropwise during 10 min, stirred for further20 min; distd.; gas chromy.;	82.1%

tri-n-propyl borate (688-71-1) + triethylaluminum (97-93-8) → triethyl borane (97-94-9)

Conditions	Yield
In neat (no solvent) Sonication; (N2), Et3Al introduced into a flask connected to a condenser containingalcohol at -20°C, stirred and heated to 120°C in an oil bath, added alkyl borate dropwise during 10 min, stirred for further 20 min; distd.; gas chromy.;	80.1%

ethylmagnesium bromide (925-90-6) + trifluoroborane diethyl ether (109-63-7) → triethyl borane (97-94-9)

Conditions	Yield
In diethyl ether at 50-60°C;	80%
In diethyl ether at 50-60°C;	80%

tetramethoxydiborane (7318-94-7) + triethylaluminum (97-93-8) → triethyl borane (97-94-9) + tetraethyldiborane (21649-17-2)

Conditions	Yield
In pentane byproducts: (C2H5)2AlOCH3; Al(C2H5)3 added to B2(OMe)4, stirred at -35°C, standing for 2 h at -30°C; solvent evapd. at -10°C bath temp., elem.anal.;	A 20% B 80%

triethyl borate (150-46-9) + triethylaluminum (97-93-8) → triethyl borane (97-94-9)

Conditions	Yield
In neat (no solvent) Sonication; (N2), Et3Al introduced into a flask connected to a condenser containingalcohol at -20°C, stirred and heated to 120°C in an oil bath, added alkyl borate dropwise during 10 min, stirred for further 20 min; distd.; gas chromy.;	78.8%

Triisopropyl borate (5419-55-6) + triethylaluminum (97-93-8) → triethyl borane (97-94-9)

Conditions	Yield
In neat (no solvent) Sonication; (N2), Et3Al introduced into a flask connected to a condenser containingalcohol at -20°C, stirred and heated to 120°C in an oil bath, added alkyl borate dropwise during 10 min, stirred for further 20 min; distd.; gas chromy.;	75.1%

triisobutyl borate (13195-76-1) + triethylaluminum (97-93-8) → triethyl borane (97-94-9)

Conditions	Yield
In neat (no solvent) Sonication; (N2), Et3Al introduced into a flask connected to a condenser containingalcohol at -20°C, stirred and heated to 120°C in an oil bath, added alkyl borate dropwise during 10 min, stirred for further 20 min; distd.; gas chromy.;	75.1%

diethylchloroborane (5314-83-0) + sodium triethyl-1-propinylborate (14949-99-6) → (C2H5)2(CH3)2C4B2(C2H5)2 + triethyl borane (97-94-9) + tetra-B-ethyl-B,B'-((Z)-1-ethyl-2-methyl-ethene-1,2-diyl)-bis-borane (138517-68-7)

Conditions	Yield
In diethyl ether byproducts: NaCl; dropping soln. of 38 mmol ClB(C2H5)2 in 20 ml diethyl ether to soln. of 37 mmol Na-salt in 40 ml diethyl ether within 20 min under Ar, rise in temp., reflux; refluxing for 4 h;; filtration; complete removal of solvent in vac. at <=40°C; distn. in vac.; product mixt. obtained; (11)B NMR spectroscopy; b. p.;;	A 11-18 B 7-14 C 75%
In diethyl ether byproducts: NaCl; dropping soln. of 0.5 mol ClB(C2H5)2 in 100 ml diethyl ether to soln. of 0.49 mol Na-salt in 500 ml diethyl ether within 2 h under Ar, rise in temp., boiling; refluxing for 3 h;; filtration; distn. of solvent at atmospheric pressure at <=80°C; removal of remaining ether and B(C2H5)3 in vac. at <=50°C; distn. of residue in vac.; product mixt. obtained; (11)B NMR spectroscopy; b. p.;;	A 31-58 B 22-26 C 20-43

Trimethyl borate (121-43-7) + triethylaluminum (97-93-8) → triethyl borane (97-94-9)

Conditions	Yield
In neat (no solvent) Sonication; (N2), Et3Al introduced into a flask connected to a condenser containingalcohol at -20°C, stirred and heated to 120°C in an oil bath, added alkyl borate dropwise during 10 min, stirred for further 20 min; distd.; gas chromy.;	74.2%

boric acid tributyl ester (688-74-4) + triethyl-alane; compound with diethyl ether (13824-25-4, 14002-28-9) → triethyl borane (97-94-9)

Conditions	Yield
In neat (no solvent) Sonication; (N2), Et3Al*Et2O introduced into a flask connected to a condenser containing alcohol at -20°C, stirred and heated to 120°C in an oil bath, added alkyl borate dropwise during 10 min, stirred for further20 min; distd.; gas chromy.;	69%

triisobutyl borate (13195-76-1) + triethyl-alane; compound with diethyl ether (13824-25-4, 14002-28-9) → triethyl borane (97-94-9)

Conditions	Yield
In neat (no solvent) Sonication; (N2), Et3Al*Et2O introduced into a flask connected to a condenser containing alcohol at -20°C, stirred and heated to 120°C in an oil bath, added alkyl borate dropwise during 10 min, stirred for further20 min; distd.; gas chromy.;	67%

ethyl bromide (74-96-4) + Trimethyl borate (121-43-7) + aluminium (7429-90-5) → triethyl borane (97-94-9)

Conditions	Yield
With iodine In neat (no solvent) Sonication; N2; ultrasound treatment of EtBr and Al, addn. of B-compd.;	65%

Trimethyl borate (121-43-7) + triethyl-alane; compound with diethyl ether (13824-25-4, 14002-28-9) → triethyl borane (97-94-9)

Conditions	Yield
In neat (no solvent) Sonication; (N2), Et3Al*Et2O introduced into a flask connected to a condenser containing alcohol at -20°C, stirred and heated to 120°C in an oil bath, added alkyl borate dropwise during 10 min, stirred for further20 min; distd.; gas chromy.;	65%

triethylboroxine (3043-60-5) + triethylaluminum (97-93-8) → triethyl borane (97-94-9)

Conditions	Yield
In paraffin Product distribution / selectivity;	63.3%
at 70℃; Product distribution / selectivity;	44.7%

ethyl bromide (74-96-4) + boric acid tributyl ester (688-74-4) + aluminium (7429-90-5) → triethyl borane (97-94-9)

Conditions	Yield
With iodine In neat (no solvent) Sonication; N2; ultrasound treatment of EtBr and Al, addn. of B-compd.;	58.5%

Triisopropyl borate (5419-55-6) + triethyl-alane; compound with diethyl ether (13824-25-4, 14002-28-9) → triethyl borane (97-94-9)

Conditions	Yield
In neat (no solvent) Sonication; (N2), Et3Al*Et2O introduced into a flask connected to a condenser containing alcohol at -20°C, stirred and heated to 120°C in an oil bath, added alkyl borate dropwise during 10 min, stirred for further20 min; distd.; gas chromy.;	57%

ethyl bromide (74-96-4) + tri-n-propyl borate (688-71-1) + aluminium (7429-90-5) → triethyl borane (97-94-9)

Conditions	Yield
With iodine In neat (no solvent) Sonication; N2; ultrasound treatment of EtBr and Al, addn. of B-compd.;	56.5%

triethyl borane (97-94-9) + N-Cyclohexylcyclododecylidenamin (79014-37-2) → ethane (74-84-0) + (Z/E)-(N-Cyclohexyl-1-cyclododecenylamino)diethylboran (74793-30-9)

Conditions	Yield
With diethylboryl-pivalate at 150℃; for 19h;	A 100% B 96%
With diethylboryl-pivalate at 110℃; for 24h; Product distribution; reactivity of 1h with pure diethyl(pivaloyloxy)borane, different reaction times;	A 4.78 mmol B n/a

triethyl borane (97-94-9) + (E)-1-methoxy-4-(2-nitrovinyl)benzene (3179-10-0, 5576-97-6) → (E)-1-(but-1-en-1-yl)-4-methoxybenzene (18657-09-5)

Conditions	Yield
With air In tetrahydrofuran at 20℃;	100%
In tetrahydrofuran for 5h; Heating;	96%
With air In hexane; acetic acid
In tetrahydrofuran at 20℃; for 0.166667h;

triethyl borane (97-94-9) + 1,1'-(2-nitroethene-1,1-diyl)dibenzene (5670-69-9) → 1,1-diphenyl-1-butene (1726-14-3)

Conditions	Yield
With (t-BuO)2 In tetrahydrofuran for 3h; Irradiation;	100%

triethyl borane (97-94-9) + (E)-2-(4-methylphenyl)-1-nitroethene (101671-00-5) → (E)-1-(but-1-en-1-yl)-4-methylbenzene (54372-77-9, 7642-12-8, 91130-33-5)

Conditions	Yield
In tetrahydrofuran for 2h; Heating;	100%

triethyl borane (97-94-9) + (Z)-1,6-bis(trimethylsilyl)hexa-3-ene-1,5-diyne (92787-97-8) → Diethyl-((1E,3Z)-1-ethyl-2,6-bis-trimethylsilanyl-hexa-1,3-dien-5-ynyl)-borane

Conditions	Yield
at 100℃; for 48h;	100%

triethyl borane (97-94-9) + 1-[bis(diisopropylamino)boryl]imidazole (675837-54-4) → 1-[bis(diisopropylamino)boryl]imidazole(N3-B)triethylborane

Conditions	Yield
In tetrahydrofuran at -78 - 20℃;	100%

triethyl borane (97-94-9) + 2-methylphenyl aldehyde (529-20-4) → 1-(2-methylphenyl)-1-propanol (61017-92-3)

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0); tri-tert-butyl phosphine; 1-(Prop-2-enyl)-1,2,3,4,5-pentamethylcyclopenta-2,4-dien In hexane; toluene at 0℃;	100%
With tri-tert-butyl phosphine; bis(1,5-cyclooctadiene)nickel (0) In tetrahydrofuran; hexane; water at 20℃; for 20h;	81%

triethyl borane (97-94-9) + bis(dimethylsilylethynyl)dimethylsilane (123853-91-8) → 4-ethyl-2-diethylboryl-1,1-dimethyl-2,5-bis(dimethylsilyl)-1-sila-2,4-cyclopentadiene

Conditions	Yield
at 100℃; for 12h;	100%
In neat (no solvent) under Ar; Si compd. added to BEt3, mixt. heated at 100°C for 12 h; volatiles removed under vac.;	99%

triethyl borane (97-94-9) + 4-methyl-N-(2-oxoethyl)-N-(prop-2-yn-1-yl)benzenesulfonamide (317842-50-5) → 5-ethyl-1,2,3,6-tetrahydro-1-[(4-methylphenyl)sulfonyl]-pyridin-3-ol

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; methanol at 65℃; for 9h;	100%

triethyl borane (97-94-9) + (trimethyl)(3-methylbut-3-en-1-ynyl)silane (18387-60-5) → (Z)-4-(diethylboryl)-2-methyl-3-(trimethylsilyl)-1,3-hexadiene (111869-79-5)

Conditions	Yield
In neat (no solvent) trialkylborane racts with silylalkine at 140°C (24 h) in autoclav;	100%
In neat (no solvent) trialkylborane racts with silylalkine for 126 h at 100°C; volatiles are removed, distn. at 0.001 Torr; elem. anal.;	58%

triethyl borane (97-94-9) + 1-Phenyl-2-(trimethylsilyl)acetylene (2170-06-1) → (E)-2-diethylboryl-1-phenyl-1-trimethylsilyl-1-butene (125212-51-3)

Conditions	Yield
In neat (no solvent) trialkylborane racts with silylalkine at 125°C (16 h) and at 150°C (5 h) in autoclav;	100%
In neat (no solvent) trialkylborane racts with silylalkine for 60 h at 100°C; volatiles are removed, distn. at 0.001 Torr; elem. anal.;	71%

(η2-2-tert-butyl-1-phosphaacetylene)(trimethylphosphane)zirconocene (126898-91-7) + [Zr(C5H5)2(HCCHPCC(CH3)3)] + triethyl borane (97-94-9) → [(Zr(C5H5)2)2((CH3)3CCP)2(C2H2)]

Conditions	Yield
In toluene byproducts: Me3P*BEt3; equimolar mixture; warming (-78 to 20°C);	100%

(CH3)2Si(CCSn(CH3)3)(CC)C(CH3)3 (153331-55-6) + triethyl borane (97-94-9) → CB(C2H5)2C(C2H5)C(Sn(CH3)3)Si(CH3)2CC(CH3)3 (153331-60-3)

Conditions	Yield
In toluene N2; addn. of 80 mmol BEt3 to a solution of 20 mmol trimethylstannylethinylsilane; stirring for 1 h at room temperature;; removal of the volatiles at 5E-3 Torr;;	100%

Upstream product

• 150-46-9 triethyl borate 
• 557-20-0 diethylzinc 
• 97-93-8 triethylaluminum 
• 102-24-9 cyclotriboric acid trimethyl ester 
• 101-36-0 tri-n-butoxyboroxin 
• 74-85-1 ethene 
• 75-00-3 chloroethane 
• 925-90-6 ethylmagnesium bromide 
• 373-74-0 methyltrifluorosilane 
• 63599-31-5 C₆H₁₅BF^(1-) 
• 75-02-5 1-fluoroethylene 
• 688-74-4 boric acid tributyl ester 
• 3043-60-5 triethylboroxine 
• 703-86-6 2,4,6-trichloro-1,3,5-trimethylborazine 

Downstream Products

• 53907-92-9 triethyl borane 
• 627-44-1 diethylmercury 
• 74-85-1 ethene 
• 93130-39-3 diethyl-benzyloxy-borane 
• 7397-46-8 diethyl methoxy borane 
• 57387-81-2 E-Diethyl-(vinyloxy)-boran 
• 64847-85-4 3-ethyl cyclohexanone 
• 3696-37-5 2-ethylmalononitrile 
• 26553-46-8 ethyl (E)-3-hexenoate 
• 58881-47-3 O¹,O⁶-bis-diethylboranyl-O²,O³;O⁴,O⁵-bis-ethylboranediyl-galactitol 
• 56797-48-9 diethyl(phenyl)borane 
• 60218-11-3 Diaethyl-(benzyl)-boran 
• 15523-24-7 sodium tetraethylborate 
• 21205-42-5 2-[(Z)-(diethylboranyl-amino)-phenyl-methylene]-cyclohexanone 

Relevant academic research and scientific papers

ULTRASONIC IRRADIATION IN THE SYNTHESIS OF TRIETHYLBORANE FROM ETHYL BROMIDE VIA ETHYLALUMINIUM SESQUIBROMIDE

Ethyl bromide and aluminum powder were irradiated with ultrasound to form ethylaluminum sesquibromide, which was then treated with triethyl borate to give triethylborane in satisfactory yield and purity.In comparison to other existing methods, ultrasonic irradiation seems to be a simple and effective process for the synthesis of organoboron compounds.

Synthesis and structural characterization of the first seven-vertex nido-carborane anion: nido-3,4-Et2C2B5H6-

The reaction of closo-2,3-Et2C2B5H5 with Li-(BEt3)H in the presence of (CH3)4NCl has been found to result in the formation of the first seven-vertex nido-carborane anion nido-3,4-Et2C2B5H6-. A single-crystal X-ray study has demonstrated that the anion adopts an open-cage geometry based on a dodecahedron missing one five-connected vertex. Crystal data: space group P212121, Z = 4, a = 9.257 (1) ?, b = 9.359 (3) ?, c = 17.803 (2) ?. The structure was refined by full-matrix least squares to a final R of 0.055 and Rw of 0.064 for the 1128 unique reflections having Fo2 > 3σ(Fo2).

REACTION OF DIETHYLHYDROXYBORANE WITH TRIALKYLALUMINIUM

The reaction of diethylhydrodryborane with trialkylaluminium has been studied.Trialkylboranes and diethyltriisobutydialuminium dioxide were isolated and characterized.A two-stage mechanism is proposed for the formation.

Lewis acid catalysis: Regioselective hydroboration of alkynes and alkenes promoted by scandium triflate

The first commercially available scandium-catalysed selective hydroboration of alkynes and alkenes with HBpin (pin = OC-Me2CMe2O) in the presence of a catalytic amount of NaHBEt3 has been developed. This protocol can be applicable to a wide range of substrates including aromatic, aliphatic with cyclic and acyclic side chains, and heteroaryl systems with broad functional-group compatibility. Mechanistic studies revealed that the reaction occurs in a syn fashion via the σ-bond metathesis between the alkenyl scandium species and HBpin.

Aluminum Hydride Catalyzed Hydroboration of Alkynes

An aluminum-catalyzed hydroboration of alkynes using either the commercially available aluminum hydride DIBAL-H or bench-stable Et3Al?DABCO as the catalyst and H-Bpin as both the boron reagent and stoichiometric hydride source has been developed. Mechanistic studies revealed a unique mode of reactivity in which the reaction is proposed to proceed through hydroalumination and σ-bond metathesis between the resultant alkenyl aluminum species and HBpin, which acts to drive turnover of the catalytic cycle.

Generation of organolithium compounds bearing super silyl ester and their application to Matteson rearrangement

It's super-silyl-fragilithyl-ester-aryl-docious: The super silyl group is a strong protecting group for carboxylic acids and provides a method for direct lithiation that is compatible with the ester moiety. Organolithium compounds bearing a super silyl ester react with a variety of electrophiles in high yields (see scheme). The reaction of lithiated super silyl chloroacetate with a boron compound gives α-functionalization of the ester moiety by Matteson rearrangement. Copyright

Scope and post-transformations for the borane-isocyanide multicomponent reactions: Concise access to structurally diverse heterocyclic compounds

A recently described family of multicomponent reactions (MCRs) involving isocyanides, aldehydes, dipolarophiles and alkylboranes that yield highly substituted aziridines, oxazolidines and pyrrolidines has been studied in detail. In this work the scope of these processes is significantly increased by preparing the borane input through hydroboration of alkenes or organometallic processes, in tandem with the MCR. The aldehyde range is also expanded, and indole-3-carbaldehydes yield reactive imines and bis-indolyloxazolidines, depending on the electron density of the heterocycle. Finally, the obtained adducts constitute an ideal platform to generate structurally diverse compounds using simple post-condensation modifications. In this way, indole imines undergo stereoselective hydrocyanation and oxazolidines are reductively opened to give amino alcohols. Additionally, palladium-, ruthenium- and gold-catalyzed processes lead to a variety of complex heterocycles. The methodology is simple, efficient and highly divergent, leading to an array of interesting scaffolds for medicinal chemistry. Copyright

Electron-rich N-heterocyclic silylene (NHSi)-iron complexes: Synthesis, structures, and catalytic ability of an isolable hydridosilylene-iron complex

The first electron-rich N-heterocyclic silylene (NHSi)-iron(0) complexes are reported. The synthesis of the starting complex is accomplished by reaction of the electron-rich Fe0 precursor [(dmpe)2Fe(PMe 3)] 1 (dmpe =1,2-bis(dimethylphosphino)ethane) with the N-heterocyclic chlorosilylene LSiCl (L = PhC(NtBu)2) 2 to give, via Me3P elimination, the corresponding iron complex [(dmpe)2Fe(←:Si(Cl)L)] 3. Reaction of in situ generated 3 with MeLi afforded [(dmpe)2Fe(←:Si(Me)L)] 4 under salt metathesis reaction, while its reaction with Li[BHEt3] yielded [(dmpe) 2Fe(←:Si(H)L)] 5, a rare example of an isolable SiII hydride complex and the first such example for iron. All complexes were fully characterized by spectroscopic means and by single-crystal X-ray diffraction analyses. DFT calculations further characterizing the bonding situation between the SiII and Fe0 centers were also carried out, whereby multiple bonding character is detected in all cases (Wiberg Bond Index >1). For the first time, the catalytic activity of a SiII hydride complex was investigated. Complex 5 was used as a precatalyst for the hydrosilylation of a variety of ketones in the presence of (EtO)3SiH as a hydridosilane source. In most cases excellent conversions to the corresponding alcohols were obtained after workup. The reaction pathway presumably involves a ketone-assisted 1,2-hydride transfer from the SiII to Fe0 center, as a key elementary step, resulting in a betaine-like silyliumylidene intermediate. The appearance of the latter intermediate is supported by DFT calculations, and a mechanistic proposal for the catalytic process is presented.

METHOD FOR PRODUCING TRIHYDROCARBYLBORANE

The present invention provides a method for industrial production of trihydrocarbylborane which method is excellent both in quality and in cost. The present invention is concerned with production of trihydrocarbylborane, comprising a reaction synthesizing the trihydrocarbylborane and aluminum oxide from trihydrocarbylboroxine and trihydrocarbylaluminum, characterized in that the reaction is allowed to proceed so that the trihydrocarbylaluminum is present at the end of the reaction in an amount of 0.5 moles or more per mole of the aluminum oxide produced in the reaction.

METHOD FOR PRODUCING HEXAALKYLBORAZINE

The invention relates to a method for producing hexaalkylborazine represented by formula 2 from a borazine represented by the formula 1, an alkene and a ligand transition-metal complex catalyst. For both formulas 1 and 2, R1 represents an alkyl group and may be the same or different. R2 represents a hydrogen atom or an alkyl group, and may be the same or different, and at least one of the R2 is a hydrogen atom, and R3 represents a an alkyl group, and may be the same or different.