sodium 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% |
Reported in EPA TSCA Inventory.
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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