Product Name

  • Name

    Dimethylaminoborane

  • EINECS 200-823-7
  • CAS No. 74-94-2
  • Article Data42
  • CAS DataBase
  • Density 0.69 g/cm3
  • Solubility 125 g/L in water at 20°C
  • Melting Point 36 °C(lit.)
  • Formula C2H10BN
  • Boiling Point 59-65 °C
  • Molecular Weight 58.9191
  • Flash Point 65 °C
  • Transport Information UN 2926 4.1/PG 2
  • Appearance white crystalline powder with an amine odour
  • Safety 16-28-36/37-45-33-15
  • Risk Codes 11-24/25-36/37/38-20
  • Molecular Structure Molecular Structure of 74-94-2 (Dimethylaminoborane)
  • Hazard Symbols FlammableF,ToxicT
  • Synonyms Dimethylamine,compd. with BH3 (6CI);Dimethylamine, compd. with borane (1:1) (8CI);Methanamine, N-methyl-, compd. with borane (1:1);Borane, compd. withN-methylmethanamine (1:1);Borane, compd. with dimethylamine (1:1) (8CI);Methanamine, N-methyl-, boron complex;(Dimethylamine)trihydroboron;Dimethylamine compound with borane (1:1);Dimethylamine-borane;NSC 10218;Boron,trihydro(N-methylmethanamine)-, (T-4)-;
  • PSA 23.85000
  • LogP -0.95740

Synthetic route

sodium tetrahydroborate
16940-66-2

sodium tetrahydroborate

dimethylammonium salt

dimethylammonium salt

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 4h;93%
dimethyl amine
124-40-3

dimethyl amine

diborane
19287-45-7

diborane

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
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;
sodium tetrahydroborate
16940-66-2

sodium tetrahydroborate

dimethyl amine
124-40-3

dimethyl amine

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
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;;
N,N-dimethylammonium chloride
506-59-2

N,N-dimethylammonium chloride

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
With sodium tetrahydroborate In 1,2-dimethoxyethane at 20℃; Cooling with ice;71%
With lithium borohydride In diethyl ether at -78 - 20℃;
lithium borohydride

lithium borohydride

N,N-dimethylammonium chloride
506-59-2

N,N-dimethylammonium chloride

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
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;
potassium borohydride

potassium borohydride

N,N-dimethylammonium chloride
506-59-2

N,N-dimethylammonium chloride

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
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%
Me3N*BH2SPh

Me3N*BH2SPh

dimethyl amine
124-40-3

dimethyl amine

A

dimethylamine borane
74-94-2

dimethylamine borane

B

Me2NH*BH2SPh
1387442-05-8

Me2NH*BH2SPh

Conditions
ConditionsYield
at 20℃; for 36h;A 10%
B 46%
dimethylamine borane
1838-13-7

dimethylamine borane

lithium borohydride

lithium borohydride

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
In tetrahydrofuran; water at 20℃; for 4h; Inert atmosphere;10%
calcium borohydride

calcium borohydride

dimethyl amine
124-40-3

dimethyl amine

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
In tetrahydrofuran
boron trioxide

boron trioxide

hydrogen
1333-74-0

hydrogen

dimethyl amine
124-40-3

dimethyl amine

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
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;;
sodium dimethylamidotrihydridoborate

sodium dimethylamidotrihydridoborate

water
7732-18-5

water

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
In hydrogenchloride hydrolysis with 0.05n HCl, equilibrium;;
sodium tetrahydroborate
16940-66-2

sodium tetrahydroborate

dimethylammonium dihydrogen phosphate
23307-08-6

dimethylammonium dihydrogen phosphate

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
In neat (no solvent) heating; dissolving in (CH3)2NH2;; evapn. in vac. or recrystn. (petroleum ether);;
dimethylamine borane
1838-13-7

dimethylamine borane

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
With pyrographite In not given with C generated in an electric arc; further by-products;;
dimethylamine borane
1838-13-7

dimethylamine borane

methylamine
74-89-5

methylamine

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
In tetrahydrofuran byproducts: HB{N(CH3)2}(NHCH3);
In cyclohexane byproducts: HB{N(CH3)2}(NHCH3);
dimethylamine borane
1838-13-7

dimethylamine borane

N,N',N''-triethylborazane
26200-45-3, 7270-53-3, 26200-44-2

N,N',N''-triethylborazane

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
In neat (no solvent) byproducts: (HBNC2H5)3; on heating;;
dimethylamine borane
1838-13-7

dimethylamine borane

N,N',N''-tripropylborazane
26200-46-4, 26200-47-5

N,N',N''-tripropylborazane

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
In neat (no solvent) byproducts: (HB-N-n-C3H7)3; on heating;;
dimethylamine borane
1838-13-7

dimethylamine borane

N,N',N''-triisopropylborazane
272443-95-5

N,N',N''-triisopropylborazane

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
In neat (no solvent) byproducts: (HB-N-i-C3H7)3; on heating;;
dimethyl amine
124-40-3

dimethyl amine

diborane
19287-45-7

diborane

A

[H2B((CH3)2NH)2](1+)*[BH4](1-)=[H2B((CH3)2NH)2][BH4]

[H2B((CH3)2NH)2](1+)*[BH4](1-)=[H2B((CH3)2NH)2][BH4]

B

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
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;
lithium borohydride

lithium borohydride

N,N-dimethylaminodichlorophosphane
683-85-2

N,N-dimethylaminodichlorophosphane

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
In neat (no solvent) at 80°C in mixture with other products;;
phosphine-borane
19121-56-3

phosphine-borane

dimethyl amine
124-40-3

dimethyl amine

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
In neat (no solvent) byproducts: {(CH3)2NH2}{H2P{BH3)2}; < -45°C, at higher temp. formation of ionic by-product; discussion of mechanism;;
lithium borohydride

lithium borohydride

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

dimethylamine borane
74-94-2

dimethylamine borane

B

trimethylamine-borane
75-22-9

trimethylamine-borane

Conditions
ConditionsYield
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;
trimethylamine-borane
75-22-9

trimethylamine-borane

dimethyl amine
124-40-3

dimethyl amine

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
In neat (no solvent) excess amine, room temp.;;
P(BH3)F3
14931-39-6

P(BH3)F3

dimethyl amine
124-40-3

dimethyl amine

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
In diethyl ether byproducts: PF3; excess amine;;
triethylamine-borane
1722-26-5

triethylamine-borane

dimethyl amine
124-40-3

dimethyl amine

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
In neat (no solvent) excess amine, room temp.;;
N,N',N''-triisopropylborazane
272443-95-5

N,N',N''-triisopropylborazane

H2BN(CH3)2*2H2B-NH-(i-C3H7)

H2BN(CH3)2*2H2B-NH-(i-C3H7)

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
In neat (no solvent) byproducts: (HB-N-i-C3H7)3; on heating;;
H3BCO*2NH(CH3)2

H3BCO*2NH(CH3)2

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
byproducts: (CH3)2NH, CO; at room temp.;;
byproducts: (CH3)2NH, CO; at room temp.;;
{(CH3)2N}F2PBH3

{(CH3)2N}F2PBH3

dimethyl amine
124-40-3

dimethyl amine

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
In diethyl ether byproducts: (CH3)2NPF2; very slow react.;;
bis(dimethylamino)phosphine borane

bis(dimethylamino)phosphine borane

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
byproducts: H2, HB{N(CH3)2}2; at 65°C;;
{Cd(NH3)6}(2+)*2{BH4}(1-)={Cd(NH3)6}{BH4}2

{Cd(NH3)6}(2+)*2{BH4}(1-)={Cd(NH3)6}{BH4}2

dimethyl amine
124-40-3

dimethyl amine

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
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
106587-23-9

(CH3)2AsN(CH3)2BH3

dimethylarsine
593-57-7

dimethylarsine

A

tetramethyldiarsine
471-35-2

tetramethyldiarsine

B

dimethylamine borane
74-94-2

dimethylamine borane

Conditions
ConditionsYield
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;
dimethylamine borane
74-94-2

dimethylamine borane

hydrogen
1333-74-0

hydrogen

Conditions
ConditionsYield
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
74-94-2

dimethylamine borane

cyclic(dimethylamino borane) dimer
23884-11-9

cyclic(dimethylamino borane) dimer

Conditions
ConditionsYield
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%
dimethylamine borane
74-94-2

dimethylamine borane

benzoic acid
65-85-0

benzoic acid

N,N-dimethylbenzamide
611-74-5

N,N-dimethylbenzamide

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene for 12h; Reflux;99%
dimethylamine borane
74-94-2

dimethylamine borane

hexanoic acid
142-62-1

hexanoic acid

N,N-dimethylhexanamide
5830-30-8

N,N-dimethylhexanamide

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene for 12h; Reflux;98%
dimethylamine borane
74-94-2

dimethylamine borane

Trimethylacetic acid
75-98-9

Trimethylacetic acid

Tripivaloyloxyboran-dimethylamin-Addukt

Tripivaloyloxyboran-dimethylamin-Addukt

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 4h;98%
1,4-dioxane
123-91-1

1,4-dioxane

n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

dimethylamine borane
74-94-2

dimethylamine borane

lithium (dimethylamino)hydroborate, adduct with 1,4-dioxane

lithium (dimethylamino)hydroborate, adduct with 1,4-dioxane

Conditions
ConditionsYield
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%
dimethylamine borane
74-94-2

dimethylamine borane

dimethylamine borane
1838-13-7

dimethylamine borane

Conditions
ConditionsYield
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
109-72-8, 29786-93-4

n-butyllithium

dimethylamine borane
74-94-2

dimethylamine borane

A

lithium (dimethylamino)hydroborate

lithium (dimethylamino)hydroborate

B

tris(dimethylamino)borane
4375-83-1

tris(dimethylamino)borane

C

Dimethylamino-di-n-butyl-boran
7289-86-3

Dimethylamino-di-n-butyl-boran

D

Li{B(n-C4H9)4}
15243-31-9

Li{B(n-C4H9)4}

Conditions
ConditionsYield
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
dimethylamine borane
74-94-2

dimethylamine borane

C19H42BFeN3P2

C19H42BFeN3P2

sodium tetraphenyl borate
143-66-8

sodium tetraphenyl borate

C21H46BFeN4P2(1+)*C24H20B(1-)

C21H46BFeN4P2(1+)*C24H20B(1-)

Conditions
ConditionsYield
With N,N-dimethylammonium chloride In tetrahydrofuran at 50℃; for 18h; Inert atmosphere;96%
1-indoline
496-15-1

1-indoline

dimethylamine borane
74-94-2

dimethylamine borane

1-borylindoline
1355176-05-4

1-borylindoline

Conditions
ConditionsYield
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
74-94-2

dimethylamine borane

[(2,6-(t-Bu2PO)2C5H3N)Rh(H2)][tetrakis(3,5-bis(trifluoromethyl)phenyl)borate]
1361399-35-0

[(2,6-(t-Bu2PO)2C5H3N)Rh(H2)][tetrakis(3,5-bis(trifluoromethyl)phenyl)borate]

C23H49BN2O2P2Rh(1+)*C32H12BF24(1-)

C23H49BN2O2P2Rh(1+)*C32H12BF24(1-)

Conditions
ConditionsYield
Inert atmosphere;95%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

dimethylamine borane
74-94-2

dimethylamine borane

lithium (dimethylamino)hydroborate

lithium (dimethylamino)hydroborate

Conditions
ConditionsYield
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%
dimethylchloroamine
1585-74-6

dimethylchloroamine

dimethylamine borane
74-94-2

dimethylamine borane

(bisdimethylamine)dihydroboronium(+) chloride

(bisdimethylamine)dihydroboronium(+) chloride

Conditions
ConditionsYield
In tetrachloromethane dropwise addn. of (CH3)2NCl in CCl4, pptn.;;92%
dimethylamine borane
74-94-2

dimethylamine borane

Cyclohexanecarboxylic acid
98-89-5

Cyclohexanecarboxylic acid

N,N-dimethylcyclohexanecarboxamide
17566-51-7

N,N-dimethylcyclohexanecarboxamide

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene for 12h; Reflux;92%
dimethylamine borane
74-94-2

dimethylamine borane

A

bis(dimethylamino)borane
2386-98-3

bis(dimethylamino)borane

B

cyclic(dimethylamino borane) dimer
23884-11-9

cyclic(dimethylamino borane) dimer

Conditions
ConditionsYield
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
74-94-2

dimethylamine borane

tributylstannyl trifluoromethanesulfonate
68725-14-4

tributylstannyl trifluoromethanesulfonate

A

(μ-dimethylamino)diborane
23273-02-1

(μ-dimethylamino)diborane

B

tri-n-butyl-tin hydride
688-73-3

tri-n-butyl-tin hydride

C

cyclic(dimethylamino borane) dimer
23884-11-9

cyclic(dimethylamino borane) dimer

Conditions
ConditionsYield
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%
1,3,5-Trioxan
110-88-3

1,3,5-Trioxan

n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

dimethylamine borane
74-94-2

dimethylamine borane

lithium (dimethylamino)hydroborate, adduct with 1,3,5-trioxane

lithium (dimethylamino)hydroborate, adduct with 1,3,5-trioxane

Conditions
ConditionsYield
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
109-72-8, 29786-93-4

n-butyllithium

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

dimethylamine borane
74-94-2

dimethylamine borane

lithium (dimethylamino)hydroborate, adduct with N,N,N',N'-tetramethylethylenediamine

lithium (dimethylamino)hydroborate, adduct with N,N,N',N'-tetramethylethylenediamine

Conditions
ConditionsYield
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
109-72-8, 29786-93-4

n-butyllithium

(1,4,7,10-tetraoxacyclododecane)
294-93-9

(1,4,7,10-tetraoxacyclododecane)

dimethylamine borane
74-94-2

dimethylamine borane

lithium (dimethylamino)hydroborate, adduct with 12-crown-4

lithium (dimethylamino)hydroborate, adduct with 12-crown-4

Conditions
ConditionsYield
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
74-94-2

dimethylamine borane

A

(μ-dimethylamino)diborane
23273-02-1

(μ-dimethylamino)diborane

B

cyclic(dimethylamino borane) dimer
23884-11-9

cyclic(dimethylamino borane) dimer

Conditions
ConditionsYield
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%
tris(pentafluorophenyl)alane toluene

tris(pentafluorophenyl)alane toluene

dimethylamine borane
74-94-2

dimethylamine borane

C20H10AlBF15N

C20H10AlBF15N

Conditions
ConditionsYield
In toluene for 0.0833333h; Inert atmosphere; Schlenk technique;87%
hydrogenchloride
7647-01-0

hydrogenchloride

dimethylamine borane
74-94-2

dimethylamine borane

N-Dimethyl-B-monochlor-borazan

N-Dimethyl-B-monochlor-borazan

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether Inert atmosphere; Schlenk technique; Glovebox;86%
with stoichiometric amounts;;
with stoichiometric amounts;;
dimethylamine borane
74-94-2

dimethylamine borane

C33H51CaN3O

C33H51CaN3O

C35H61BCaN4O

C35H61BCaN4O

Conditions
ConditionsYield
In toluene at 20℃; for 0.5h; Inert atmosphere;86%
dimethylamine borane
74-94-2

dimethylamine borane

oxalic acid
144-62-7

oxalic acid

C2H7N*C4BO8(1-)*H(1+)

C2H7N*C4BO8(1-)*H(1+)

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 64h; Inert atmosphere;85%
dimethylamine borane
74-94-2

dimethylamine borane

potassium hydride

potassium hydride

potassium dimethylaminoborohydride

potassium dimethylaminoborohydride

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 3 - 5h; Inert atmosphere;83%
dimethylamine borane
74-94-2

dimethylamine borane

{(CH3)2NBH2}2

{(CH3)2NBH2}2

Conditions
ConditionsYield
With C52H46BFeO2P4(1+)*Br(1-); potassium tert-butylate In toluene at 23℃; for 16h; Catalytic behavior;83%
dimethylamine borane
74-94-2

dimethylamine borane

water-d2
7789-20-0

water-d2

BH3*NDMe2
65761-09-3

BH3*NDMe2

Conditions
ConditionsYield
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%

Dimethylaminoborane Consensus Reports

Reported in EPA TSCA Inventory.

Dimethylaminoborane Specification

The Dimethylaminoborane, with the CAS registry number 74-94-2, is also known as Dimethylamine compound with borane (1:1). It belongs to the product categories of Organometallics; B (Classes of Boron Compounds); Boranes; Reduction; Synthetic Organic Chemistry; Organoboron and borato-metal complexes. Its EINECS number is 200-823-7. This chemical's molecular formula is C2H10BN and molecular weight is 58.92. What's more, its systematic name is Trihydrido(N-methylmethanamine)boron. Its classification codes are: (1)Drug / Therapeutic Agent; (2)Mutation data; (3)Skin / Eye Irritant. It should be sealed and stored in a cool and ventilated place. Moreover, it should be protected from oxides, heat and fire. It is sensitive to water and air. This chemical is used in reductivealkylation of protein.

Physical properties of Dimethylaminoborane are: (1)#H bond acceptors: 1; (2)#H bond donors: 0; (3)#Freely Rotating Bonds: 1; (4)Polar Surface Area: 4.44 Å2.

When you are using this chemical, please be cautious about it as the following:
This chemical is highly flammable, so you should keep it away from sources of ignition - No smoking. It is toxic in contact with skin and if swallowed and is harmful by inhalation. After contact with skin, you must wash immediately with plenty of ... (to be specified by the manufacturer). This substance is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing and gloves. In case of accident or if you feel unwell, you should seek medical advice immediately (show the label where possible). You need take precautionary measures against static discharges and keep this chemical away from heat.

You can still convert the following datas into molecular structure:
(1)SMILES: [BH3-][NH+](C)C
(2)Std. InChI: InChI=1S/C2H10BN/c1-4(2)3/h4H,1-3H3
(3)Std. InChIKey: RUOMFVPJBOADHA-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intraperitoneal 55900ug/kg (55.9mg/kg)   "Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964Vol. -, Pg. 693, 1964.
guinea pig LDLo oral 50mg/kg (50mg/kg)   National Technical Information Service. Vol. OTS0535833.
mouse LD50 intraperitoneal 200mg/kg (200mg/kg)   Journal of Pharmaceutical Sciences. Vol. 69, Pg. 1025, 1980.
mouse LD50 intravenous 56mg/kg (56mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#05150.
mouse LDLo oral 50mg/kg (50mg/kg)   National Technical Information Service. Vol. OTS0535833.
rabbit LD50 intraperitoneal 35100ug/kg (35.1mg/kg)   "Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964Vol. -, Pg. 693, 1964.
rabbit LD50 skin 210mg/kg (210mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES National Technical Information Service. Vol. OTS0535833.
rat LD50 intraperitoneal 39mg/kg (39mg/kg)   "Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964Vol. -, Pg. 693, 1964.
rat LD50 oral 59mg/kg (59mg/kg)   American Industrial Hygiene Association Quarterly. Vol. 16, Pg. 280, 1955.

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