Tris dimethylamino borane

Tris(dimethylamino)borane has been prepared by dimethyl-aminolysis of boron trichloride, with or without solvent,1-5 and by the reaction of boron trifluoride with dimethylamine in the presence of a suitable Grignard reagent.6 The procedure described here is a modification of the reaction of dimethylamine with boron trichloride in pentane as the solvent. 

three-necked flask is equipped with a stirrer, a 500-ml. dropping funnel protected by a calcium chloride drying tube, and a reflux condenser topped with a potassium hydroxide drying tube. The reaction vessel is cooled in an ice-salt bath and is charged with 500 ml. of dry pentane and 293 g. (6.5 mols) of anhydrous dimethylamine. A solution of 117.2 g. (1 mol) of boron trichloride in 400 ml. of pentane, prepared by passing the gaseous chloride into chilled pentane, is added slowly with 

X Fisher Scientific Co., pentane (from petroleum), practical grade dried over sodium wire and freshly distilled. 

The synthesis was checked at one-fourth the above scale. The product was distilled through a vacuum-jacketed Yigreaux column to give 20 g. (0.14 mol) (56% yield based on the boron trichloride) of tris(dimethylamino)borane, b.p. 30°/5 to 6 mm. 

Tris(dimethylamino)borane is a colorless liquid having a typical amine odor, b.p. 147°, nd° 1.4461. It is readily and quantitatively hydrolyzed. It is miscible without decomposition with most common nonprotonic anhydrous organic solvents. 

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FLATffiRETARDANTS - PHOSPHORUS FLATffi RETARDANTS] (Vol 10) Tris(dimethylamino)borane [4375-83-1]... 

Tris(dimethylamino)borane similarly fails to 3deld a trivalent boron heterocycle, but gives the spiro-compound (CLXV). A monocyclic system of type (CLXVI) does arise from diethylaminodiphenylborane, and of type (CLXVII) from phenylboronic acid and its analogues 436). 

A. Tris(dimethylamino)borane (Note 1). A 2-L, three-necked flask equipped with a mechanical stirrer, dropping funnel, and a dry ice-cooled reflux condenser connected to a nitrogen source and a bubbler is flushed with nitrogen (Note 2). The flask is charged with 600 mL of pentane (Note 3) and 218 g (4.84 mol) of dimethylamine (Note 4), and cooled to ca. -30°C with a dry ice-methanol bath. A... 

Tris(dimethylamino)borane is available from Aldrich Chemical Company, Inc. It may also be synthesized from boron trichloride.2... 

The checkers obtained a 63% yield of tris(dimethylamino)borane. The checkers obtained bp 57°C (11 mm). 

Dimethylamine (8) Methanamine, N-methyl- (9) (124-40-3) Tris(dimethylamino)borane Borane, tris(dimethylamino)- (8) Boranetriamine, hexamethyl- (9) (4375-83-1)... 

Synthesis. One of the more common routes for the synthesis of aminoboranes involves the aminolysis of the appropriate boron halide. Trisaminoboranes are most conveniendy prepared by adding BC13 to an excess of amine in an inert solvent at low temperatures (42). For example for tris(dimethylamino)borane [4375-83-1]. ... 

Also, several polycyclic 1,3,2-diazaboracycloalkane derivatives have been reported. The first of these was the 1,8,10,9-triazaboradecalin, 7 ls>21>, which is readily obtained from a transamination reaction between tris(dimethylamino)borane and 3,3 -diaminodipropylamme as depicted in Eq. (8). 

The reaction of diborane(6) with bis or tris(dimethylamino)borane has recently been shown to be synthetically useful in the stepwise buildup of a boron-nitrogen chain leading to bis( -dimethylamino)triborane(9).7... 

Tris(acetonitrile)tricarbonylchromium and tris(acetonitrile)tricarbonyl-tungsten react with tris(dimethylamino)borane to give yellow, readily sublimable crystalline products of the type [(CH3)2N]3BM(CO)3. On the basis of their 11B nmr spectrum, -coordination of the aminoborane with a relatively strong, metal-boron interaction is suggested.8,9... 

Bicyclic enamines were prepared using the bicyclic ketone, tris(dimethylamino)borane, dimethylamine and potassium carbonate in an autoclave heated to 95-105 °C494. 

Yamamoto and Maruoka [90] found that the complexation of triamino ester with tris(dimethylamino)borane is a highly efficient lactam closure method. Celacirmine (759) and other similar spermidine alkaloids were synthesized in this manner. As shown in Scheme 52, the cyclization of the linear precursor 155 was effected with tris(dimethylamino)borane in xylene xmder reflux to furnish the lactam 158 via the intermediates 156 and 157 in 90% yield. 

C6H15NO N-hydroxy-N-propyl-1 -propan amine 7446-43-7 427.65 36.978 1,2 9344 C6H18BN3 tris(dimethylamino)borane 4375-83-1 420.65 36.315 1,2... 

Tris(dimethylamino)borane is moisture sensitive. NMR CDCI3) 8 2.52 (s,18H). 

A chiral tris(methimazolyl)borate ligand has been prepared by Bailey et ah60 by the activation of tris(dimethylamino)borane toward reaction with a chiral methimazole (l-(5)-a-methylbenzyl-2-mercaptoimidazolyl) by A-methylimidazole (Fig. 5.12). Its coordination to [RuCl2(p-cymene)]2 provides a single diastereomer complex in which the chirality of the methimazolyl substituents... 

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