13987-61-6

Usage

Uses

Used in Pharmaceutical Synthesis:
TERT-BUTYLAZOMETHINE is used as a key intermediate in the synthesis of GSK369796 (N-tert-Butyl Isoquine), a novel 4-Aminoquinoline antimalarial drug. Its unique chemical properties enable the creation of complex molecular structures, contributing to the development of effective treatments for malaria.
Used in Synthetic Chemistry:
In the field of synthetic chemistry, TERT-BUTYLAZOMETHINE serves as a versatile building block for the creation of a wide range of organic compounds. Its reactivity and structural characteristics make it a valuable asset in the development of new materials and chemical processes.

InChI:InChI=1/C5H11N/c1-5(2,3)6-4/h4H2,1-3H3

Upstream product

• 50-00-0 formaldehyd 
• 75-64-9 tert-butylamine 
• 16479-80-4 2-tert-butyl-oxaziridine 
• 75-18-3 dimethylsulfide 
• 555-16-8 4-nitrobenzaldehdye 
• 67-56-1 methanol 
• 52594-52-2 dimethyl(2,2'-bipyridine)platinum(II) 
• 811-98-3 d⁽⁴⁾-methanol 
• 113776-98-0 1-adamantylidene-1-bromo-2-(tert-butylamino)ethane 
• 113776-99-1 2-adamantylidene-N-tert-butylaziridine 

Downstream Products

• 7153-52-8 4-tert-Butyl-2-(tert-butylamino-methyl)-phenol 
• 18626-93-2 C-tert.Butylamino-N-(3,5-di-tert.butylphenyl)-nitron 
• 14610-37-8 N-methyl-tert-butylamine 
• 53198-38-2 N-Acetoxymethyl-N-nitroso-tert-butylamin 
• 90226-77-0 3-tert.-Butyl-5-methyl-oxazolidin 
• 140367-31-3 5-tert-Butyl-1-phenyl-3-pyridin-4-yl-[1,3,5]triazinan-2-one 
• 141564-68-3 3-{[tert-Butyl-(3,3-dimethyl-ureidomethyl)-amino]-methyl}-1,1-dimethyl-urea 
• 141564-69-4 3-{[tert-Butyl-(3,3-diethyl-ureidomethyl)-amino]-methyl}-1,1-diethyl-urea 
• 141564-70-7 3-{[tert-Butyl-(3,3-dipropyl-ureidomethyl)-amino]-methyl}-1,1-dipropyl-urea 
• 85517-81-3 N-Benzyl-N(tert.-butylamino-methyl)-formamid 
• 140628-15-5 1,5-Di-tert-butyl-3-phenyl-[1,3,5]triazinane-2-thione 
• 140628-24-6 5-tert-Butyl-1-(4-fluoro-phenyl)-[1,3,5]triazinane-2-thione 
• 140628-22-4 5-tert-Butyl-1-(4-nitro-phenyl)-[1,3,5]triazinane-2-thione 
• 53198-37-1 N-(1-Methoxymethyl)-N-nitroso-tert-butylamin 

Relevant academic research and scientific papers

A 3-Azacyclopropanespiro-1,2-dioxetane via Singlet Oxygenation of a Methyleneaziridine

The first three-membered ring substituted spiro-1,2-dioxetane (2) has been synthesized and characterized through the singlet oxygenation of methyleneaziridine 1.Thermodynamic properties of the decomposition of 2 are as follows: K20 deg C = 11.5 s-1; Ea = 18.3 kcal/mol; ΔH(excit.) = 17.9 kcal/mol; ΔS(excit.) = 7.5 eu.The chemical properties of this novel dioxetane are compared to those of dioxetanes 11 and 12, dioxetanimine 9, and dioxetanone 10.

Oxidation of a dimethylplatinum(II) complex with oxaziridines: A hemiaminal intermediate but no oxo complex

The complex [PtMe2(bipy)] (1; bipy = 2,2′-bipyridine) fails to react with the oxaziridine derivatives RCHON-t-Bu (R = H, Ph, 2-pyridyl) in acetone at room temperature, but an easy reaction occurs in methanol solution to give the platinum(IV) complex [Pt(OH)(OMe)Me 2(bipy)] and the corresponding imine RCH=N-t-Bu. In the case with R = Ph, the hemiaminal intermediate [Pt(OMe)(OCHPhNH-t-Bu)Me2(bipy)] was formed and then reacted only slowly to form [Pt(OH)(OMe)Me2(bipy)] and PhCH=N-t-Bu. Computational studies indicate that the reaction of 1 with oxaziridines occurs to give a charge transfer complex but that further reaction requires assistance from hydrogen bonding and coordination with specific methanol molecules. The work provides strong support for the theory that oxygen atom transfer to 1 from either dioxiranes or oxaziridines must be coupled to proton transfer and does not involve oxoplatinum(IV) intermediates.

Method of preparing electron deficient olefins

This invention relates to a process for producing electron deficient olefins, such as 2-cyanoacrylates, using an iminium salt.

Method of preparing electron deficient olefins

This invention relates to processes for producing electron deficient olefins, such as 2-cyanoacrylates, using an iminium salt, and if desired contacting the reaction byproduct with alkali to generate an amine and separating that amine therefrom.

IMINIUM SALTS AND METHODS OF PREPARING ELECTRON DEFICIENT OLEFINS USING SUCH NOVEL IMINIUM SALTS

This invention relates to novel iminium salts, which may be in the form of ionic liquids, and a process for producing electron deficient olefins, such as 2-cyanoacrylates, using such an iminium salt, for instance in the form of an ionic liquid.

trans-(±)-2-tert-butyl-3-phenyloxaziridine: A unique reagent for the oxidation of thiolates into sulfenates

(Chemical Equation Presented) Aliphatic thiolates were efficiently converted into the corresponding sulfenates by smooth oxidation with trans-(±)-2-tert-butyl-3-phenyloxaziridine at room temperature (five examples). Subsequent electrophilic quench with benzyl bromide led to sulfoxides (S-alkylation) in good to moderate yields. Application of the protocol to an aromatic substrate was also successful. This work represents the first valuable example of the use of this poorly active oxidizing agent in synthetic organic chemistry without the need for activating conditions.

EPR spectroscopic studies of N-alkyl-N-trialkylsilylmethylaminyl radicals in solution

Photochemically generated trialkylsilyl radicals R3Si (R = Me, Et, Pri) add rapidly to N-methylene-tert-butylamine (H2C=NBut) to give silylmethylaminyl radicals R3SiCH2NBut which have been studied by EPR spectroscopy.These aminyl radicals prefer conformations in which the β-C-Si bond eclipses the N-2p? orbital, formally occupied by the unpaired electron, and lineshape effect resulting from hindered rotation about the R3SiCH2-N bond are evident in the EPR spectra.The aminyl radicals Me3SiCH2NBut and Me3SiCH2NMe have been generated by displacement from aminophosphanes of the type (EtO)2PN(R)CH2SiMe3 using photochemically-generated alkoxyl radicals.The proposal in the literature that Me3SiCH2NR radical (R = Me or But) rearranges to give CH2N(R)SiMe3 radical has been confirmed and this process has been monitored by EPR spectroscopy.Since no free silyl radicals could be trapped by But2C=CH2, the rearrangement probably proceeds by an intramolecular 1,2-shift of the Me3Si group from carbon to nitrogen.The rearranged radicals CH2N(R)SiMe3 have been generated independently by hydrogen-atom abstraction from the corresponding aminosilanes Me3SiN(R)CH3.

Synthesis of alkyl- and aryl-substituted pyridines from (α,β-unsaturated) imines or oximes and carbonyl compounds

Reaction of a variety of (α,β-unsaturated) imines or oximes with aliphatic aldehydes or cyclic ketones in the presence of a secondary amine afforded alkyl-, and/or aryl-, and/or cycloalkyl-substituted pyridines. To explain their formation, a hetero Diels-Alder reaction has been postulated, in which an 1-aza-1,3-butadiene reacts with an in situ generated enamine.

AMINOMETHYLATION OF 1- AND 2-ALKYL-5-AMINOTETRAZOLES BY N-METHYLENE-tert-BUTYLAMINE

The reaction of 1- and 2-alkyl-5-aminotetrazoles with N-methylene-tert-butylamine takes place selectively. 2-Alkyl-5-aminotetrazoles enter into the reaction with the exclusive formation of 1-(2-R-tetrazol-5-yl)-3,5-di-tert-butylhexahydro-1,3,5-triazines with quantitative yields. 1-Alkyl-5-aminotetrazoles do not react with N-methylene-tert-butylamine as a result of steric hindrances created by the N-tert-butyl group of the aldimine.

AMINOMETHYLATION OF N,N'- AND N,N,N'-SUBSTITUTED UREAS BY N-METHYLENE-tert-BUTYLAMINE

The reaction of 1,3-substituted ureas with N-methylene-tert-butylamine in the absence of a solvent proceeds via mechanism of the Mannich type to give 1-R1-3-R2-5-tert-butyl-3,4,5,6-tetrahydro-1,3,5-triazin-2-ones and tert-butylamine. 1,1,3-Substituted ureas do not react with N-methylene-tert-butylamine as a consequence of the steric hindrance created by the tert-butyl grouping to obtaining the key iminium salt.