Borane tert-butylamine

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Borane tert-butylamine
Borane tert-butylamine.svg
Names
Other names
tert-Butylamine borane; Trihydro(2-methyl-2-propanamine) boron
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 230-851-5
PubChem CID
  • NC(C)(C)C.B
Properties
C4H14BN
Molar mass 86.97 g·mol−1
AppearanceWhite solid
Melting point 96 °C (205 °F; 369 K) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Borane tert-butylamine is an amine borane complex derived from tert-butylamine and borane. It is a colorless solid.

The compound is prepared by the reaction of tert-butylammonium chloride and sodium borohydride: [2]

t-BuNH3Cl + NaBH4t-BuNH2BH3 + H2 + NaCl

In organic synthesis, borane tert-butylamine can be used for selective reduction of certain functional groups including aldehydes, ketones, oximes, and imines. [3]

In photographic processing, it is used in the E-4 process, as "chemical enlighting" step in the processing of the film.

See also

Related Research Articles

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An isocyanide is an organic compound with the functional group –N+≡C. It is the isomer of the related nitrile (–C≡N), hence the prefix is isocyano. The organic fragment is connected to the isocyanide group through the nitrogen atom, not via the carbon. They are used as building blocks for the synthesis of other compounds.

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Butyllithium may refer to one of 5 isomeric organolithium reagents of which 3 are commonly used in chemical synthesis:

Potassium <i>tert</i>-butoxide Chemical compound

Potassium tert-butoxide (or potassium t-butoxide) is a chemical compound with the formula [(CH3)3COK]n (abbr. KOtBu). This colourless solid is a strong base (pKa of conjugate acid around 17), which is useful in organic synthesis. The compound is often depicted as a salt, and it often behaves as such, but its ionization depends on the solvent.

<i>tert</i>-Butyllithium Chemical compound

tert-Butyllithium is a chemical compound with the formula (CH3)3CLi. As an organolithium compound, it has applications in organic synthesis since it is a strong base, capable of deprotonating many carbon molecules, including benzene. tert-Butyllithium is available commercially as solutions in hydrocarbons (such as pentane); it is not usually prepared in the laboratory.

<span class="mw-page-title-main">Ammonia borane</span> Chemical compound

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The carbylamine reaction is the synthesis of an isocyanide by the reaction of a primary amine, chloroform, and base. The conversion involves the intermediacy of dichlorocarbene.

<i>n</i>-Butylamine Chemical compound

n-Butylamine is an organic compound (specifically, an amine) with the formula CH3(CH2)3NH2. This colourless liquid is one of the four isomeric amines of butane, the others being sec-butylamine, tert-butylamine, and isobutylamine. It is a liquid having the fishy, ammonia-like odor common to amines. The liquid acquires a yellow color upon storage in air. It is soluble in all organic solvents. Its vapours are heavier than air and it produces toxic oxides of nitrogen during combustion.

<i>tert</i>-Butylamine Chemical compound

tert-Butylamine (also erbumine and other names) is an organic chemical compound with the formula (CH3)3CNH2. It is a colorless liquid with a typical amine-like odor. tert-Butylamine is one of the four isomeric amines of butane, the others being n-butylamine, sec-butylamine and isobutylamine.

tert-Butyl isocyanide is an organic compound with the formula Me3CNC (Me = methyl, CH3). It is an isocyanide, commonly called isonitrile or carbylamine, as defined by the functional group C≡N-R. tert-Butyl isocyanide, like most alkyl isocyanides, is a reactive colorless liquid with an extremely unpleasant odor. It forms stable complexes with transition metals and can insert into metal-carbon bonds.

<span class="mw-page-title-main">Tilisolol</span> Chemical compound

Tilisolol is a beta blocker.

Triisopropylamine is an organic chemical compound consisting of three isopropyl groups bound to a central nitrogen atom. As a hindered tertiary amine, it can be used as a non-nucleophilic base and as a stabilizer for polymers; however, its applications are limited by its relatively high cost and difficult synthesis.

<span class="mw-page-title-main">Propionaldehyde</span> Chemical compound

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<span class="mw-page-title-main">Borane–tetrahydrofuran</span> Chemical compound

Borane–tetrahydrofuran is an adduct derived from borane and tetrahydrofuran (THF). These solutions, which are colorless, are used for reductions and hydroboration, reactions that are useful in synthesis of organic compounds. The use of borane–tetrahydrofuran has been displaced by borane–dimethylsulfide, which has a longer shelf life and effects similar transformations.

<span class="mw-page-title-main">Aminomethyl propanol</span> Chemical compound

Aminomethyl propanol (AMP) is an organic compound with the formula H2NC(CH3)2CH2OH. It is colorless liquid that is classified as an alkanolamine. It is a useful buffer and a precursor to numerous other organic compounds.

<span class="mw-page-title-main">Sulfur diimide</span> Chemical compound

Sulfur diimides are chemical compounds of the formula S(NR)2. Structurally, they are the diimine of sulfur dioxide. The parent member, S(NH)2, is of only theoretical interest. Other derivatives where R is an organic group are stable and useful reagents.

<i>tert</i>-Butyl hypochlorite Chemical compound

tert-Butyl hypochlorite is the organic compound with the formula (CH3)3COCl. A yellow liquid, it is a rare example of an organic hypochlorite, i.e. a compound with an O-Cl bond. It is a reactive material that is useful for chlorinations. It can be viewed as a lipophilic version of sodium hypochlorite (bleach).

<span class="mw-page-title-main">1-Hexyne</span> Chemical compound

1-Hexyne is a hydrocarbon consisting of a straight six-carbon chain having a terminal alkyne. Its molecular formula is HC2C4H9. A colorless liquid, it is one of three isomers of hexyne. It is used as a reagent in organic synthesis.

<i>tert</i>-Butyl nitrite Chemical compound

tert-Butyl nitrite is an organic compound with the formula (CH3)3CONO. A colorless liquid, it is the tert-butyl ester of nitrous acid. It is typically employed as a solution with tert-butyl alcohol.

References

  1. Nöth, Heinrich; Beyer, Hasso; Vetter, Hans-Joanchim (1964). "Beiträge zur Chemie des Bors, XXV. Bis(amin)-dihydrido-bor(III)-halogenide, [(R3–nHnN)2BH2]X2". Chemische Berichte. 97 (1): 110–118. doi:10.1002/cber.19640970115. ISSN   0009-2940.
  2. Girolami, G. S.; Rauchfuss, T. B. and Angelici, R. J., Synthesis and Technique in Inorganic Chemistry, University Science Books: Mill Valley, CA, 1999. ISBN   0935702482
  3. "Tert-Butylamine borane". pubchem.ncbi.nlm.nih.gov. NCBI. Retrieved 3 September 2019.