Conditions | Yield |
---|---|
With aluminium; aluminium trichloride In neat (no solvent) in presence of activated Al-powder, H2-pressure 2000 psi, 180°C, 1h;; separation by distn. in vac.;; | 99% |
Conditions | Yield |
---|---|
In diethyl ether at 0°C;; | 98% |
In diethyl ether byproducts: (CH3)2NOCH3; at 0°C;; | 98% |
tetramethylammonium borohydride
trimethylamine-borane
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: CH4; 220-225°C, 10E-3Torr;; | 96% |
(CH3)3NGeH3Br
diborane
A
bromogermanate
B
trimethylamine-borane
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: germanes; under N2 or in vac., excess B2H6, -78°C, 1.0 h; | A 92.5% B n/a |
With hydrogen bromide In neat (no solvent) byproducts: germanes; under N2 or in vac., allowed to warm to -63°C for 1.0 h, treated at -78°C with B2H6 followed by HBr; traces of germanes; | A 79.5% B n/a |
With hydrogen bromide In neat (no solvent) byproducts: germanes; under N2 or in vac., allowed to warm to -23°C for 0.5 h, treated at -78°C with B2H6 followed by HBr; traces of germanes; | A 58% B n/a |
With hydrogen bromide In neat (no solvent) byproducts: germanes; under N2 or in vac., allowed to warm to 23°C for 4.0 h, treated at -78°C with B2H6 followed by HBr; traces of germanes; | A 0% B n/a |
Conditions | Yield |
---|---|
With water; sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 4h; Reagent/catalyst; Solvent; | 92% |
sodium tetrahydroborate
trimethylamine hydrochloride
trimethylamine
trimethylamine-borane
Conditions | Yield |
---|---|
In water byproducts: H2; slow addn. of H2O to a mixture of NaBH4 and ((CH3)3NH)Cl in N(CH3)3 at -10°C while stirring (3h), addn. of H2O and petroleum ether, evapn. of petroleum ether phase;; | 90% |
In water byproducts: H2; slow addn. of H2O to a mixture of NaBH4 and ((CH3)3NH)Cl in N(CH3)3 at -10°C while stirring (3h), addn. of H2O and petroleum ether, evapn. of petroleum ether phase;; | 90% |
Conditions | Yield |
---|---|
In diethyl ether byproducts: H2; stirring at room temp. until end of H2-evolution, boiling for 1h, filtration, evapn.;; | 86% |
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 50°C for sublimation; | 78% |
In diethyl ether | |
In tetrahydrofuran | |
In diethyl ether byproducts: H2, LiCl; addn. of LiBH4 in ether to a small excess ammonium salt in ether while stirring and cooling, stirring at room temp. for 3h, filtration, evapn.;; recrystn. (C6H6/petroleum ether);; |
Conditions | Yield |
---|---|
In diethyl ether at 0°C;; | 86% |
at 0°C;; | 80% |
hydrogen
boron trichloride
trimethylamine
trimethylamine-borane
Conditions | Yield |
---|---|
With aluminium In neat (no solvent) byproducts: HCl; mixing N(CH3)3 and BCl3 with powdered Al at 140°C, heating to 220°C under 5000 psi while stirring;; | 85% |
With aluminium In neat (no solvent) byproducts: HCl; mixing N(CH3)3 and BCl3 with powdered Al at 140°C, heating to 220°C under 5000 psi while stirring;; | 85% |
In neat (no solvent) byproducts: HCl; excess amine, 2000 atm H2-pressure, 200°C, 60h;; | 25% |
Conditions | Yield |
---|---|
In toluene 16 h, 150°C in sealed tube; | A 79% B 84% |
Conditions | Yield |
---|---|
In toluene 150°C, 16h, closed tube;; | 84% |
Conditions | Yield |
---|---|
With carbon dioxide In water byproducts: H2; in presence of moisture;; | 80% |
In water; benzene introduction of CO2 or addn. of solns. of HCl, H3PO4, H3BO3 HCO2H, CH3CO2H or Ch3C6H4SO3H at 0-5°C (7-8h), evapn. of organic phase;; distn. in vac.;; | 79.5% |
In water; Petroleum ether introduction of CO2 or addn. of solns. of HCl, H3PO4, H3BO3 HCO2H, CH3CO2H or Ch3C6H4SO3H at 0-5°C (7-8h), evapn. of organic phase;; distn. in vac.;; | 79.5% |
In water; Petroleum ether introduction of CO2 or addn. of solns. of HCl, H3PO4, H3BO3 HCO2H, CH3CO2H or Ch3C6H4SO3H at 0-5°C (7-8h), evapn. of organic phase;; distn. in vac.;; | 79.5% |
In water; benzene introduction of CO2 or addn. of solns. of HCl, H3PO4, H3BO3 HCO2H, CH3CO2H or Ch3C6H4SO3H at 0-5°C (7-8h), evapn. of organic phase;; distn. in vac.;; | 79.5% |
sodium tetrahydroborate
trimethylamine hydrochloride
trimethylamine-borane
Conditions | Yield |
---|---|
With 18-crown-6 ether In diethyl ether refluxing under Ar for 5 h; cooling, evapn. of solvent, sublimating residue under vac.; | 80% |
In tetrahydrofuran byproducts: H2, NaCl; stirring for 2h at room temp., boiling for 12h, removal of excess NaBH4 and NaCl, evapn. of filtrate in vac.;; sublimation (60-70°C, 40-60Torr);; | 67% |
In diethyl ether | |
In tetrahydrofuran |
Conditions | Yield |
---|---|
byproducts: (CH3)2NOH; | 80% |
Conditions | Yield |
---|---|
In water byproducts: H2; react. in presence of CO2 on addn. of H2O, filtration, evapn., extractn. with H2O;; | 80% |
In water byproducts: H2; react. in presence of CO2 on addn. of H2O, filtration, evapn., extractn. with H2O;; | 80% |
In water byproducts: H2; react. in presence of H3BO3 on addn. of H2O, filtration, evapn., extractn. with H2O;; | 77% |
In water byproducts: H2; react. in presence of H3BO3 on addn. of H2O, filtration, evapn., extractn. with H2O;; | 77% |
With phosphonic Acid for 2h; Cooling with ice; Inert atmosphere; |
Conditions | Yield |
---|---|
With lithium borohydride In diethyl ether at -78 - 20℃; | 78% |
trimethylamine-borane
Conditions | Yield |
---|---|
byproducts: H2B-N(CH3)2; 24°C, 20min;; | 76% |
byproducts: H2B-N(CH3)2; 24°C, 20min;; | 76% |
byproducts: H2B-N(CH3)2; at 85.deegree.C;; | >99 |
byproducts: H2B-N(CH3)2; at 85.deegree.C;; | >99 |
Conditions | Yield |
---|---|
small excess N(CH3)3;; | 69% |
trimethylamine-borane
Conditions | Yield |
---|---|
byproducts: H2B-N(C2H5)2; on heating;; | 65% |
byproducts: H2B-N(C2H5)2; slow react. at room temp.;; |
trimethylamine-monoiodoborane (1/1)
trimethylamine-borane
Conditions | Yield |
---|---|
With sodium-potassium alloy; sodium In 1,2-dimethoxyethane reduction with Na/K-alloy (25:75 wt.-%); 2.5-3h, 0°C;; | 55% |
With sodium-potassium alloy; sodium In diethylene glycol reduction with Na/K-alloy (25:75 wt.-%); 2.5-3h, 0°C;; | 55% |
With sodium-potassium alloy; sodium In further solvent(s) reduction with Na/K-alloy (25:75 wt.-%); in N(CH3)3, 3h, 0°C;; | 44% |
Conditions | Yield |
---|---|
In diethyl ether at 0°C;; | 22% |
Conditions | Yield |
---|---|
A 22% B n/a |
Conditions | Yield |
---|---|
In neat (no solvent) 90°C;; | 17% |
Conditions | Yield |
---|---|
With sodium-potassium alloy; sodium In further solvent(s) reduction with Na/K-alloy (25:75 wt.-%); in N(CH3)3, 0°C, 15h;; | 17% |
(CH3)3NBH2(SCH3)
trimethylamine-borane
Conditions | Yield |
---|---|
byproducts: (CH3)3N, B(SCH3)3; heating 15 min to 45°C; equilibrium;; | 10% |
byproducts: (CH3)3N, B(SCH3)3; heating 15 min to 45°C; equilibrium;; | 10% |
(CH3)3SiCNBH3
trimethylamine
A
trimethylsilyl cyanide
B
trimethylamine-borane
Conditions | Yield |
---|---|
In neat (no solvent) room temp., 12d;; |
{1-(trimethylamine)-1,2-bis(trimethylphosphine)trihydrodiboron}octahydrotriborate
trimethylamine-borane
Conditions | Yield |
---|---|
slow decompn. at -30°C; |
Conditions | Yield |
---|---|
In diethyl ether | |
In tetrahydrofuran |
Conditions | Yield |
---|---|
In diethyl ether | |
In tetrahydrofuran |
Conditions | Yield |
---|---|
In diethyl ether | |
In tetrahydrofuran |
pyridine
trimethylamine-borane
iodine
((C5H5N)2BH2)(1+)*I(1-)=((C5H5N)2BH2)I
Conditions | Yield |
---|---|
In pyridine | 99% |
In pyridine byproducts: {(CH3)3NH}I; 70°C, 1h;; | |
In pyridine byproducts: {(CH3)3NH}I; 70°C, 1h;; |
Conditions | Yield |
---|---|
99% | |
99% |
trimethylamine-borane
Conditions | Yield |
---|---|
With copper(l) chloride In 1,2-dichloro-ethane at 60℃; for 0.166667h; Inert atmosphere; Schlenk technique; | 99% |
trimethylamine-borane
Conditions | Yield |
---|---|
With dirhodium(II) tetrakis[(S)-(+)-[(1S)-1-(4-bromophenyl)-2,2-diphenylcyclopropanecarboxylate]] In monoethylene glycol diethyl ether at -20℃; for 5h; Inert atmosphere; Schlenk technique; | 99% |
trimethylamine-borane
Conditions | Yield |
---|---|
With copper(l) chloride In 1,2-dichloro-ethane at 60℃; for 0.166667h; Inert atmosphere; Schlenk technique; | 99% |
trimethylamine-borane
Conditions | Yield |
---|---|
With copper(l) chloride In 1,2-dichloro-ethane at 60℃; for 0.166667h; Inert atmosphere; Schlenk technique; | 99% |
trimethylamine-borane
Conditions | Yield |
---|---|
With dirhodium(II) tetrakis[(S)-(+)-[(1S)-1-(4-bromophenyl)-2,2-diphenylcyclopropanecarboxylate]] In monoethylene glycol diethyl ether at -20℃; for 5h; Inert atmosphere; Schlenk technique; | 99% |
trimethylamine-borane
3-(4,4-dimethylpent-2-yn-1-ylidene)pentane-2,4-dione
Conditions | Yield |
---|---|
With copper(l) chloride In 1,2-dichloro-ethane at 60℃; for 0.166667h; Inert atmosphere; Schlenk technique; | 99% |
trimethylamine-borane
3-(3-(trimethylsilyl)prop-2-yn-1-ylidene)pentane-2,4-dione
Conditions | Yield |
---|---|
With copper(l) chloride In 1,2-dichloro-ethane at 60℃; for 0.166667h; Inert atmosphere; Schlenk technique; | 99% |
4-(3-phenylprop-2-yn-1-ylidene)heptane-3,5-dione
trimethylamine-borane
Conditions | Yield |
---|---|
With copper(l) chloride In 1,2-dichloro-ethane at 60℃; for 0.166667h; Inert atmosphere; Schlenk technique; | 99% |
trimethylamine-borane
Conditions | Yield |
---|---|
With copper(l) chloride In 1,2-dichloro-ethane at 60℃; for 1h; Inert atmosphere; Schlenk technique; | 99% |
trimethylamine-borane
Conditions | Yield |
---|---|
With copper(l) chloride In 1,2-dichloro-ethane at 60℃; for 0.166667h; Inert atmosphere; Schlenk technique; | 99% |
trimethylamine-borane
Conditions | Yield |
---|---|
With dirhodium(II) tetrakis[(S)-(+)-[(1S)-1-(4-bromophenyl)-2,2-diphenylcyclopropanecarboxylate]] In monoethylene glycol diethyl ether at -20℃; for 5h; Inert atmosphere; Schlenk technique; | 99% |
trimethylamine-borane
Conditions | Yield |
---|---|
With copper(l) chloride In 1,2-dichloro-ethane at 60℃; for 0.166667h; Inert atmosphere; Schlenk technique; | 99% |
trimethylamine-borane
Conditions | Yield |
---|---|
With dirhodium(II) tetrakis[(S)-(+)-[(1S)-1-(4-bromophenyl)-2,2-diphenylcyclopropanecarboxylate]] In monoethylene glycol diethyl ether at -20℃; for 5h; Inert atmosphere; Schlenk technique; | 99% |
trimethylamine-borane
Conditions | Yield |
---|---|
With dirhodium(II) tetrakis[(S)-(+)-[(1S)-1-(4-bromophenyl)-2,2-diphenylcyclopropanecarboxylate]] In monoethylene glycol diethyl ether at -20℃; for 5h; Inert atmosphere; Schlenk technique; | 99% |
Conditions | Yield |
---|---|
hydrogen chloride In water-d2 with excess acidic D2O; 20min at 25°C; extractn. with ether;; | 98% |
sulfuric acid-d2 In dichloromethane 0.5n D2SO4;; | |
sulfuric acid-d2 In diethyl ether 0.5n D2SO4;; |
trimethylamine-borane
3-(3-phenylpropyl-2-yn-1-ylidene)-2,4-pentanedione
Conditions | Yield |
---|---|
With copper(l) chloride In 1,2-dichloro-ethane at 60℃; for 0.166667h; Kinetics; Mechanism; Thermodynamic data; Inert atmosphere; Schlenk technique; | 98% |
trimethylamine-borane
Conditions | Yield |
---|---|
With copper(l) chloride In 1,2-dichloro-ethane at 60℃; for 0.166667h; Inert atmosphere; Schlenk technique; | 98% |
trimethylamine-borane
Conditions | Yield |
---|---|
With copper(l) chloride In 1,2-dichloro-ethane at 60℃; for 0.166667h; Inert atmosphere; Schlenk technique; | 98% |
trimethylamine-borane
Conditions | Yield |
---|---|
With copper(l) chloride In 1,2-dichloro-ethane at 60℃; for 0.166667h; Inert atmosphere; Schlenk technique; | 98% |
trimethylamine-borane
Conditions | Yield |
---|---|
With copper(l) chloride In 1,2-dichloro-ethane at 60℃; for 0.166667h; Inert atmosphere; Schlenk technique; | 98% |
trimethylamine-borane
Conditions | Yield |
---|---|
With dirhodium(II) tetrakis[(S)-(+)-[(1S)-1-(4-bromophenyl)-2,2-diphenylcyclopropanecarboxylate]] In monoethylene glycol diethyl ether at -20℃; for 5h; Inert atmosphere; Schlenk technique; | 98% |
trimethylamine-borane
Conditions | Yield |
---|---|
With copper(l) chloride In 1,2-dichloro-ethane at 60℃; for 0.166667h; Inert atmosphere; Schlenk technique; | 98% |
trimethylamine-borane
Conditions | Yield |
---|---|
With copper(l) chloride In 1,2-dichloro-ethane at 60℃; for 0.166667h; Inert atmosphere; Schlenk technique; | 98% |
Conditions | Yield |
---|---|
In dichloromethane for 2h; Inert atmosphere; Combinatorial reaction / High throughput screening (HTS); Glovebox; | 98% |
Conditions | Yield |
---|---|
In dichloromethane at 50℃; for 1h; Sealed tube; Inert atmosphere; Glovebox; | 97% |
In hexane; toluene Inert atmosphere; Schlenk technique; | 54% |
4-(3-phenylprop-2-yn-1-ylidene)heptane-3,5-dione
trimethylamine-borane
Conditions | Yield |
---|---|
With dirhodium(II) tetrakis[(S)-(+)-[(1S)-1-(4-bromophenyl)-2,2-diphenylcyclopropanecarboxylate]] In monoethylene glycol diethyl ether at -20℃; for 5h; Inert atmosphere; Schlenk technique; | 97% |
Reported in EPA TSCA Inventory.
The Borane-trimethylamine complex, with the CAS registry number 75-22-9, is also known as Borane-trimethylamine (1:1). It belongs to the product categories of B (Classes of Boron Compounds); Boranes; Reduction; Synthetic Organic Chemistry. Its EINECS number is 200-850-4. This chemical's molecular formula is C3H12BN and molecular weight is 72.95. What's more, its systematic name is (N,N-Dimethylmethanamine)(trihydrido)boron. Its classification codes are: (1)Drug / Therapeutic Agent; (2)Mutation data. The product should be sealed and stored in containers with dry inert gas which are placed in cool and dry places. It is used in the reduction reaction of ketone and Schiff (Schiff bases) and hydroboration of olefin.
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. 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, gloves and eye/face protection. You need take precautionary measures against static discharges and keep it away from ... (incompatible materials to be indicated by the manufacturer).
You can still convert the following datas into molecular structure:
(1)SMILES: [BH3-][N+](C)(C)C
(2)Std. InChI: InChI=1S/C3H12BN/c1-5(2,3)4/h1-4H3
(3)Std. InChIKey: KQVSXUGMDCAISO-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 140mg/kg (140mg/kg) | Journal of Pharmaceutical Sciences. Vol. 74, Pg. 755, 1985. | |
rat | LD50 | intraperitoneal | 175mg/kg (175mg/kg) | Journal of Occupational Medicine. Vol. 1, Pg. 46, 1959. |
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