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74-94-2

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74-94-2 Usage

Chemical Properties

white crystalline powder with an amine odour

Uses

Different sources of media describe the Uses of 74-94-2 differently. You can refer to the following data:
1. Borane-dimethylamine complex is used in a nickel-catalyzed reduction of electron-deficient aryl tosylates. It also serves as a reducing agent in electrolytic deposition of metals, alloys, semiconductors and insulators.
2. Reagent used in a Ni-catalyzed reduction of electron-deficient aryl tosylates. The catalyst is composed of commercially available Ni(PPh3)2Cl2(529621) and PCy3(261971).

Safety Profile

Poison by ingestion, intraperitoneal, and intravenous routes. A skin and eye irritant. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also DIMETHYLAMINE and BORANE.

Check Digit Verification of cas no

The CAS Registry Mumber 74-94-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 4 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 74-94:
(4*7)+(3*4)+(2*9)+(1*4)=62
62 % 10 = 2
So 74-94-2 is a valid CAS Registry Number.
InChI:InChI=1/C2H7N.B/c1-3-2;/h3H,1-2H3;

74-94-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (D1842)  Dimethylamine Borane  >95.0%(T)

  • 74-94-2

  • 25g

  • 180.00CNY

  • Detail
  • TCI America

  • (D1842)  Dimethylamine Borane  >95.0%(T)

  • 74-94-2

  • 100g

  • 550.00CNY

  • Detail
  • TCI America

  • (D1842)  Dimethylamine Borane  >95.0%(T)

  • 74-94-2

  • 500g

  • 1,990.00CNY

  • Detail
  • Alfa Aesar

  • (89149)  Borane-dimethylamine complex, 97%   

  • 74-94-2

  • 25g

  • 271.0CNY

  • Detail
  • Alfa Aesar

  • (89149)  Borane-dimethylamine complex, 97%   

  • 74-94-2

  • 100g

  • 830.0CNY

  • Detail
  • Aldrich

  • (180238)  Boranedimethylaminecomplex  97%

  • 74-94-2

  • 180238-5G

  • 200.07CNY

  • Detail
  • Aldrich

  • (180238)  Boranedimethylaminecomplex  97%

  • 74-94-2

  • 180238-25G

  • 485.55CNY

  • Detail
  • Aldrich

  • (180238)  Boranedimethylaminecomplex  97%

  • 74-94-2

  • 180238-100G

  • 1,488.24CNY

  • Detail

74-94-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Dimethylaminoborane

1.2 Other means of identification

Product number -
Other names BORON HYDRIDE DIMETHYLAMINE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:74-94-2 SDS

74-94-2Synthetic 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%

74-94-2Relevant articles and documents

H/D scrambling in a chromium-catalyzed dehydrocoupling reaction of a borane-dimethylamine adduct

Kawano, Yasuro,Shimoi, Mamoru

, p. 11950 - 11955 (2017)

H/D scrambling took place in a chromium-catalyzed dehydrocoupling reaction of a deuterium-labeled borane-dimethylamine adduct. In the hydrogen elimination of BH3·NDMe2 (1a-dN), H2, HD and D2 were generated in 65:30:5 ratio, and 62% of deuterium atoms were incorporated into the major product, the dimethylaminoborane dimer. Proton and deuteron nuclei were thus concentrated into the evolved dihydrogen and aminoborane dimer, respectively. The mechanism of H/D scrambling is understood based on the reaction pathway of the dehydrocoupling of 1a, which was previously proposed based on DFT calculations. The H/D distribution in the products is explained by the energy difference according to the deuterated position in an intermediate of the dehydrocoupling reaction.

Preparation and basicity of sodium dimethylamidotrihydroborate(III)

Gilje, John W.,Ronan, Richard J.

, p. 1248 - 1249 (1968)

-

Gupta, V. K.,Krannich, L. K.,Watkins, C. L.

, p. 173 - 178 (1987)

Preparation method of dimethylamine borane

-

Paragraph 0032-0089, (2021/06/12)

The invention discloses a preparation method of dimethylamine borane, which comprises the following step of in a solvent, in the presence of monopotassium phosphate or phosphoric acid, reacting dimethylamine or hydrochloride thereof with BH4 ion-containing hydroboron to obtain the dimethylamine borane. The solvent is water or a mixed solvent of water and an organic solvent. The preparation method of dimethylamine borane disclosed by the invention is mild in condition, high in yield, high in purity and clean in reaction.

Method for the production of amine borane complex (by machine translation)

-

Paragraph 0035; 0036, (2017/12/05)

The invention belongs to the technical field of material preparation, in particular relates to a method for the production of amine borane complex. This invention adopts the borane amine of the direct reaction of an inert gas stream, by regulating the ratio of the two, the need for further post-processing, to make the final product amine complex and offer. In the reaction process such impurity is introduced into the salt-free, does not use an organic solvent; the use of borohydride such as the reagent to produce the borane, for now the current system, can avoid direct operation of toxic gas borane. The method of the invention is simple in operation, the product has high purity, low cost, and can be continuous large-scale production. At the same time, the method and other way to produce the amine borane complex equipment compatible, production equipment by simple method can be used to adjust the production. (by machine translation)

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