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Dimethylaminoborane Basic information Product Name: Dimethylaminoborane Synonyms: Borane-dimethylamine complex, 98+%;dimethylamine,compd.withborane(1:1);DimethylamineBorane(DMAB);Dimethylaminoboran;borane, compd. with dimethylamine;dimethylami
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inquirysodium tetrahydroborate
dimethylamine borane
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 4h; | 93% |
Conditions | Yield |
---|---|
In neat (no solvent) excess amine, 30-40°C, concn. of soln.;; distn. in vac. (60°C/2Torr) or recrystn. (petroleum ether);; | 91% |
In neat (no solvent) excess amine, 30-40°C, concn. of soln.;; distn. in vac. (60°C/2Torr) or recrystn. (petroleum ether);; | 91% |
In diethyl ether product in liquid form, crystn. on standing;; distn. in vac.;; | 961 % |
In gas determination of react.-enthalpy;; | |
for 2h; Inert atmosphere; Gas phase; Cooling with ice; |
Conditions | Yield |
---|---|
With iodine In 1,2-dimethoxyethane byproducts: NaI, H2; dropwise addn. of NaBH4 and I2 in DME to amine in DME, removal of solvent, addn. of C6H6, filtration, evapn. of filtrate in a N2 stream, drying in vac.;; recrystn. from CH2Cl2/hexane mixture;; | 84.4% |
With potassium dihydrogenphosphate In water at -20 - 5℃; for 10h; Solvent; Reagent/catalyst; Autoclave; Large scale; | 84.5% |
With boron trifluoride diethyl etherate In tetrahydrofuran refluxing, filtartion, evapn. of solvent;; |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In 1,2-dimethoxyethane at 20℃; Cooling with ice; | 71% |
With lithium borohydride In diethyl ether at -78 - 20℃; |
Conditions | Yield |
---|---|
In neat (no solvent) in vac., 3h;; distn. in vac. at 75-76°C/0.5Torr;; | 70% |
In diethyl ether byproducts: H2, LiCl; room temp., 3h, filtration, evapn.;; recrystn. from C6H6/petroleum ether;; | |
In diethyl ether amine hydrochloride was added at -78°C to soln. LiBH4 in Et2O andstirred for 30 min, allowed to warm to room temp. and stirred for 5 h; react. mixt. was cooled to -45°C, slvent was removed in vacuo, residue was heated in vacuo at 65°C for sublimation; |
Conditions | Yield |
---|---|
With sodium hydroxide In 1,2-dimethoxyethane; water at -5 - 15℃; for 6 - 10h; Conversion of starting material; | 55.1% |
With sodium hydroxide In tetrahydrofuran; water at -10 - 15℃; for 10 - 14h; Conversion of starting material; | 54% |
Conditions | Yield |
---|---|
at 20℃; for 36h; | A 10% B 46% |
Conditions | Yield |
---|---|
In tetrahydrofuran; water at 20℃; for 4h; Inert atmosphere; | 10% |
Conditions | Yield |
---|---|
In tetrahydrofuran |
Conditions | Yield |
---|---|
With aluminium trichloride; aluminium In neat (no solvent) High Pressure; heating the mixture under a H2-pressure of 800-900kg/cm**2 to 273°C for 10h; in mixture with other products;; |
Conditions | Yield |
---|---|
In hydrogenchloride hydrolysis with 0.05n HCl, equilibrium;; |
sodium tetrahydroborate
dimethylammonium dihydrogen phosphate
dimethylamine borane
Conditions | Yield |
---|---|
In neat (no solvent) heating; dissolving in (CH3)2NH2;; evapn. in vac. or recrystn. (petroleum ether);; |
Conditions | Yield |
---|---|
With pyrographite In not given with C generated in an electric arc; further by-products;; |
Conditions | Yield |
---|---|
In tetrahydrofuran byproducts: HB{N(CH3)2}(NHCH3); | |
In cyclohexane byproducts: HB{N(CH3)2}(NHCH3); |
dimethylamine borane
N,N',N''-triethylborazane
dimethylamine borane
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: (HBNC2H5)3; on heating;; |
dimethylamine borane
N,N',N''-tripropylborazane
dimethylamine borane
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: (HB-N-n-C3H7)3; on heating;; |
dimethylamine borane
N,N',N''-triisopropylborazane
dimethylamine borane
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: (HB-N-i-C3H7)3; on heating;; |
Conditions | Yield |
---|---|
In neat (no solvent) prepared by condensing diborane in small portions to the amine until anexcess of diborane is present as indicated by the vapour pressure; detected by (13)C-NMR; |
Conditions | Yield |
---|---|
In neat (no solvent) at 80°C in mixture with other products;; |
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: {(CH3)2NH2}{H2P{BH3)2}; < -45°C, at higher temp. formation of ionic by-product; discussion of mechanism;; |
N,N-dimethyl-formamide
A
dimethylamine borane
B
trimethylamine-borane
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide soln. of LiBH4 in DMF under dry, oxygen free N2 (after 7 ds at ambient temp.); not isolated; (11)B-NMR; |
Conditions | Yield |
---|---|
In neat (no solvent) excess amine, room temp.;; |
Conditions | Yield |
---|---|
In diethyl ether byproducts: PF3; excess amine;; |
Conditions | Yield |
---|---|
In neat (no solvent) excess amine, room temp.;; |
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: (HB-N-i-C3H7)3; on heating;; |
dimethylamine borane
Conditions | Yield |
---|---|
byproducts: (CH3)2NH, CO; at room temp.;; | |
byproducts: (CH3)2NH, CO; at room temp.;; |
Conditions | Yield |
---|---|
In diethyl ether byproducts: (CH3)2NPF2; very slow react.;; |
dimethylamine borane
Conditions | Yield |
---|---|
byproducts: H2, HB{N(CH3)2}2; at 65°C;; |
Conditions | Yield |
---|---|
With hydrogen sulfide In neat (no solvent) treatment with H2S; filtration, removal of excess amine;; distn. or treatment with activated coal in ether;; | >99 |
With hydrogen sulfide In neat (no solvent) treatment with H2S; filtration, removal of excess amine;; distn. or treatment with activated coal in ether;; | >99 |
(CH3)2AsN(CH3)2BH3
dimethylarsine
A
tetramethyldiarsine
B
dimethylamine borane
Conditions | Yield |
---|---|
In (2)H8-toluene Me2AsH is condensed onto the frozen soln. of B-compd. (-196°C) in a NMR-tube, sealing of the tube, agitating at -95°C, reaction is studied from -80 to -10°C; monitored by NMR-spectroscopy; |
Conditions | Yield |
---|---|
With [IrH2{(P(phenyl)2(o-C6H4CO))2H}] In tetrahydrofuran; water for 0.133333h; Catalytic behavior; Kinetics; Thermodynamic data; Reagent/catalyst; | 100% |
With ethanol; ReBr2(NO)(CH3CN)(PTA)2 In ethanol Kinetics; byproducts: B(OC2H5)3, (CH3)2NH; ethanolysis of amine-borane with 1 mol.-% ReBr2(NO)(MeCN)(1,3,5-triaza-7-phosphaadamantane)2 at room temp. or at 50°C; | |
With ethanol In ethanol byproducts: B(OC2H5)3, (CH3)2NH; ethanolysis of amine-borane at 50°C; |
dimethylamine borane
cyclic(dimethylamino borane) dimer
Conditions | Yield |
---|---|
With N-benzylidene tert-butylamine; C28H24BF12P In benzene at 25℃; for 6h; Temperature; | 99% |
With 2,2,6,6-tetramethyl-piperidine; trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-benzene at 20℃; for 2h; Inert atmosphere; | 89% |
With Mes2P-C{=C(H)-Ph}-AltBu2 at 45 - 90℃; Catalytic behavior; Concentration; Time; | 77% |
Conditions | Yield |
---|---|
In 5,5-dimethyl-1,3-cyclohexadiene for 12h; Reflux; | 99% |
Conditions | Yield |
---|---|
In 5,5-dimethyl-1,3-cyclohexadiene for 12h; Reflux; | 98% |
Conditions | Yield |
---|---|
In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 4h; | 98% |
Conditions | Yield |
---|---|
In hexane byproducts: butane; (anhydrous conditions); dissoln. of BH3*NHMe2 in 1,4-dioxane, after cooling in an ice-bath addn. of n-BuLi in hexane within 1 h with stirring, further stirring at room temp. for 2 h; crystn. (toluene); elem. anal.; | 97% |
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; tris(pentafluorophenyl)borate In C6D5Cl for 24h; | 97% |
With phenylmagnesium bromide In tetrahydrofuran at 20℃; for 5h; Inert atmosphere; | 6% |
With bis(cyclopentadienyl)titanium dichloride; n-butyllithium In toluene at 20℃; for 20h; Inert atmosphere; |
n-butyllithium
dimethylamine borane
B
tris(dimethylamino)borane
C
Dimethylamino-di-n-butyl-boran
D
Li{B(n-C4H9)4}
Conditions | Yield |
---|---|
In hexane byproducts: butane; (anhydrous conditions); stirring (4 h); centrifugation, washing (hexane), drying (vac.); elem. anal.; | A 96% B n/a C n/a D n/a |
Conditions | Yield |
---|---|
With N,N-dimethylammonium chloride In tetrahydrofuran at 50℃; for 18h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: H2; (inert atm., Schlenk technique); heating mixt. of 1 equiv. of indoline and 1 equiv. of borane deriv. at 100°C under Ar flow; extn. (CHCl3), filtration through celite, evapn., washing with hexanes, NMR and IR; | 95% |
With catalyst: Pd/C In neat (no solvent) byproducts: H2, (CH3)2NH; (inert atm., Schlenk technique); heating mixt. of 1 equiv. of indoline, 1 equiv. of borane deriv. and Pd/C at 100°C for 2 h under Ar flow; extn. (CHCl3), filtration through celite, evapn., washing with hexanes, NMR and IR; | 87% |
dimethylamine borane
[(2,6-(t-Bu2PO)2C5H3N)Rh(H2)][tetrakis(3,5-bis(trifluoromethyl)phenyl)borate]
Conditions | Yield |
---|---|
Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
Stage #1: n-butyllithium; dimethylamine borane In hexane at -78℃; for 1h; Inert atmosphere; Stage #2: In hexane at 20℃; for 1h; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
In tetrachloromethane dropwise addn. of (CH3)2NCl in CCl4, pptn.;; | 92% |
dimethylamine borane
Cyclohexanecarboxylic acid
N,N-dimethylcyclohexanecarboxamide
Conditions | Yield |
---|---|
In 5,5-dimethyl-1,3-cyclohexadiene for 12h; Reflux; | 92% |
dimethylamine borane
A
bis(dimethylamino)borane
B
cyclic(dimethylamino borane) dimer
Conditions | Yield |
---|---|
With 2,2,6,6-tetramethyl-piperidine; tributylstannyl trifluoromethanesulfonate In 1,2-dichloro-benzene at 20℃; for 2h; Inert atmosphere; | A 7% B 91% |
With C56H65FeN2 In toluene at 20℃; for 7h; Catalytic behavior; Inert atmosphere; Glovebox; Schlenk technique; | A 10% B 90% |
With [Mg{CH(SiMe3)2}(THF)2] In benzene-d6 at 60℃; Mechanism; Inert atmosphere; |
dimethylamine borane
tributylstannyl trifluoromethanesulfonate
A
(μ-dimethylamino)diborane
B
tri-n-butyl-tin hydride
C
cyclic(dimethylamino borane) dimer
Conditions | Yield |
---|---|
With 2,2,6,6-tetramethylpiperidine In further solvent(s) byproducts: H2; N2 or Ar; 1,2-dichlorobenzene soln. of nBuSnOTf (0.39 mmol) and 2,2,6,6-tetramethylpiperidine (0.4 mmol) added to soln. of B compd. (0.42 mmol), mixt. stirred at 20°c for 2 h; NMR; | A 2% B n/a C 91% |
Conditions | Yield |
---|---|
In hexane; toluene byproducts: butane; (anhydrous conditions); dissoln. of BH3*NHMe2 and 1,3,5-trioxane in toluene, addn. of n-BuLi in hexane within 10 min with stirring, reflux (1 h); filtration while hot, crystn. on cooling, recrystn. (hot toluene); elem.anal.; | 90% |
n-butyllithium
N,N,N,N,-tetramethylethylenediamine
dimethylamine borane
Conditions | Yield |
---|---|
In hexane byproducts: butane; (anhydrous conditions); dissoln. of BH3*NHMe2 in TMEDA, after cooling inan ice-bath addn. of n-BuLi in hexane within 1 h with stirring, further stirring at room temp. for 2 h; addn. of hexane, filtration, crystn. within 12 h and additionally by cooling of the supernatant to -18°C; elem. anal.; | 90% |
n-butyllithium
(1,4,7,10-tetraoxacyclododecane)
dimethylamine borane
Conditions | Yield |
---|---|
In hexane; toluene byproducts: butane; (anhydrous conditions); dissoln. of BH3*NHMe2 and 12-crown-4 in toluene,addn. of n-BuLi in hexane within 10 min with stirring, reflux (1 h); filtration while hot, crystn. on cooling; elem. anal.; | 90% |
dimethylamine borane
A
(μ-dimethylamino)diborane
B
cyclic(dimethylamino borane) dimer
Conditions | Yield |
---|---|
With 2,2,6,6-tetramethylpiperidine; Me3SiOTf In further solvent(s) byproducts: H2; N2 or Ar; 1,2-dichlorobenzene soln. of Me3SiOTf (0.39 mmol) and 2,2,6,6-tetramethylpiperidine (0.4 mmol) added to soln. of B compd. (0.42 mmol), mixt. stirred at 20°c for 2 h; NMR; | A 3% B 89% |
With 2,2,6,6-tetramethylpiperidine; Et3SiOTf In further solvent(s) byproducts: H2; N2 or Ar; 1,2-dichlorobenzene soln. of Et3SiOTf (0.39 mmol) and 2,2,6,6-tetramethylpiperidine (0.4 mmol) added to soln. of B compd. (0.42 mmol), mixt. stirred at 20°c for 2 h; NMR; | A 1% B 87% |
With 2,6-di-tert-burtylpyridine; Me3SiOTf In further solvent(s) byproducts: H2; N2 or Ar; 1,2-dichlorobenzene soln. of Me3SiOTf (0.39 mmol) and 2,6-di-tert-butylpyridine (0.4 mmol) added to soln. of B compd. (0.42 mmol), mixt. stirred at 20°c for 2 h; NMR; | A 18% B 31% |
Conditions | Yield |
---|---|
In toluene for 0.0833333h; Inert atmosphere; Schlenk technique; | 87% |
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether Inert atmosphere; Schlenk technique; Glovebox; | 86% |
with stoichiometric amounts;; | |
with stoichiometric amounts;; |
Conditions | Yield |
---|---|
In toluene at 20℃; for 0.5h; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 64h; Inert atmosphere; | 85% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 3 - 5h; Inert atmosphere; | 83% |
dimethylamine borane
Conditions | Yield |
---|---|
With C52H46BFeO2P4(1+)*Br(1-); potassium tert-butylate In toluene at 23℃; for 16h; Catalytic behavior; | 83% |
Conditions | Yield |
---|---|
In D2O (Ar); a soln. of B compd. stirred at 40°C for 24 h; extd. (CH2Cl2), the org. layer dried (MgSO4), filtered, evapd., sublimedtwice under dynamic vac. at 20°C; | 82% |
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