108-09-8

Usage

Uses

1. Used in Chromatography Applications:
1,3-Dimethylbutylamine is used as a study agent for the application of unfunctionized polymethacrylate resin (TSKgel G3000PWXL) as a stationary phase in liquid chromatography with UV detection. This application helps in understanding the behavior and separation capabilities of the resin in various chromatographic processes.
2. Used in Chemical Synthesis:
1,3-Dimethylbutylamine can be used as a reagent or intermediate in the synthesis of various organic compounds, taking advantage of its amine functional group and unique structural properties.
3. Used in Pharmaceutical Industry:
Due to its amine nature, 1,3-Dimethylbutylamine may be utilized in the development of pharmaceutical compounds, potentially serving as a building block for the creation of new drugs or drug candidates.
4. Used in Research and Development:
The compound can be employed in research and development settings to study its properties, reactivity, and potential applications in various chemical and biological processes.
5. Used in Analytical Chemistry:
1,3-Dimethylbutylamine may be used as a reference compound or standard in analytical chemistry for the calibration of instruments and the development of new analytical methods.

Air & Water Reactions

Highly flammable. Slightly soluble in water. May be air sensitive.

Reactivity Profile

1,3-Dimethylbutylamine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Health Hazard

May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

Flammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion and skin contact. Mildly toxic by inhalation. A dangerous fire and explosion hazard when exposed to heat or flame; can react vigorously with oxidizing materials. To fight fire, use foam, CO2 dry chemical. When heated to decomposition it emits toxic fumes of NOx See also MINES.

InChI:InChI=1/C6H15N/c1-5(2)4-6(3)7/h5-6H,4,7H2,1-3H3/p+1/t6-/m1/s1

Upstream product

• 141-79-7 4-methyl-pent-3-en-2-one 
• 53867-52-0 bis-(1,3-dimethyl-butylidene)-hydrazine 
• 2158-24-9 4-methyl-pent-3-en-2-one oxime 
• 108-10-1 4-methyl-2-pentanone 
• 64-17-5 ethanol 
• 26842-43-3 2-amino-2,4-dimethylpentanonitrile 
• 1258934-39-2 N-(4-methylpentan-2-yl)pyrimidine-2-sulfonamide 
• 68-11-1 mercaptoacetic acid 
• 100-46-9 benzylamine 
• 75240-54-9 N-(4-methylpentan-2-yl)formamide 
• 7533-40-6 (S)-2-amino-4-methylpentan-1-ol 
• 7533-40-6 2-amino-4-methyl-1-pentanol 
• 67-56-1 methanol 
• 105-44-2 4-methyl-pentan-2-one oxime 

Downstream Products

• 32781-26-3 (1,3-dimethyl-butyl)-(1,3-dimethyl-butyliden)-amine 
• 42966-66-5 cyclohexyl-(1,3-dimethyl-butyl)-amine 
• 40092-95-3 C₁₅H₂₂ClN₃O 
• 20640-02-2 2-<4-Methyl-2-pentylamino>-aethanthiol 
• 95945-86-1 (1,3-dimethyl-butyl)-[1-methyl-3-(2,6,6-trimethyl-cyclohex-1-enyl)-propyl]-amine 
• 40487-41-0 (1,3-Dimethyl-butyl)-(3,4-dimethyl-2,6-dinitro-phenyl)-amine 
• 40318-81-8 4-chloro-2,6-dinitro-N-(1,3-dimethylbutyl)-m-toluidine 
• 67330-79-4 1-(2,6-Diethyl-4-methyl-phenyl)-3-(1,3-dimethyl-butyl)-thiourea 
• 38008-69-4 (1,3-Dimethyl-butyl)-carbamic acid 3-methylsulfanylcarbonylamino-phenyl ester 
• 30301-47-4 (1,3-Dimethyl-butyl)-[(E)-3-phenyl-prop-2-en-(E)-ylidene]-amine 
• 78527-91-0 (R,S)-L-tyrosyl-D-alanylglycine 1,3-dimethylbutyl amide trifluoroacetate 
• 78527-92-1 (R,S)-L-tyrosyl-D-methionylglycine 1,3-dimethylbutyl amide trifluoroacetate 
• 1187092-65-4 N-(4-methylpentan-2-yl)-3-phenylpropanamide 
• 34017-00-0 N-(4-methylpentan-2-yl)benzamide 

Related news

Identification and quantification of 1,3-Dimethylbutylamine (cas 108-09-8) (DMBA) from Camellia sinensis tea leaves and dietary supplements08/19/2019

1,3-dimethylbutylamine (DMBA), is a CNS stimulant, which has recently been identified in multiple dietary supplements and sometimes labeled as a natural constituent of Pouchung tea. DMBA is an homologue of 1,3-dimethylamylamine (DMAA) which the US Food and Drug Administration has attempted to re...detailed

Relevant academic research and scientific papers

Biochemical and Structural Characterization of an (R)-Selective Transaminase in the Asymmetric Synthesis of Chiral Hydroxy Amines

An (R)-selective transaminase RbTA with excellent stereoselectivity (>99% ee) in the asymmetric amination of hydroxy ketones was identified. Biochemical characterization showed that RbTA exhibited the highest activity toward 4-hydroxy-2-butanone among reported enzymes, and that it has broad substrate specificity, including for aliphatic, aromatic, and alicyclic ketones. Crystallization of RbTA were performed, as were molecular docking and mutagenesis studies. Residue Tyr125 plays a key role in substrate recognition by forming a hydrogen bond with hydroxy ketone. The applicability of the enzyme was determined in preparative-scale synthesis of (R)-3-amino-1-butanol, demonstrating the potential of RbTA as a green biocatalyst for production of value-added chiral hydroxy amines. This study provides an efficient tool for enzymatic synthesis of chiral hydroxy amines, as well as structural insight into substrate recognition by transaminases in the asymmetric amination of hydroxy ketones. (Figure presented.).

Ambient-Temperature Synthesis of Primary Amines via Reductive Amination of Carbonyl Compounds

Efficient synthesis of primary amines via low-temperature reductive amination of carbonyl compounds using NH3 and H2 as the nitrogen and hydrogen resources is highly desired and challenging in the chemistry community. Herein, we employed naturally occurring phytic acid as a renewable precursor to fabricate titanium phosphate (TiP)-supported Ru nanocatalysts with different reduction degrees of RuO2 (Ru/TiP-x, x represents the reduction temperature) by combining ball milling and molten-salt processes. Very interestingly, the obtained Ru/TiP-100 had good catalytic performance for the reductive amination of carbonyl compounds at ambient temperature, resulting from the synergistic cooperation of the support (TiP) and the Ru/RuO2 with a suitable proportion of Ru0 (52%). Various carbonyl compounds could be efficiently converted into the corresponding primary amines with high yields. More importantly, the conversion of other substrates with reducible groups could also be achieved at ambient temperature. Detailed investigations indicated that the partially reduced Ru and the support (TiP) were indispensable. The high activity and selectivity of Ru/TiP-100 catalyst originates from the relatively high acidity and the suitable electron density of metallic Ru0.

Rapid and Quantitative Profiling of Substrate Specificity of ω-Transaminases for Ketones

ω-Transaminases (ω-TAs) have gained growing attention owing to their capability for asymmetric synthesis of chiral amines from ketones. Reliable high-throughput activity assay of ω-TAs is essential in carrying out extensive substrate profiling and establishing a robust screening platform. Here we report spectrophotometric and colorimetric methods enabling rapid quantitation of ω-TA activities toward ketones in a 96-well microplate format. The assay methods employ benzylamine, a reactive amino donor for ω-TAs, as a cosubstrate and exploit aldehyde dehydrogenase (ALDH) as a reporter enzyme, leading to formation of benzaldehyde detectable by ALDH owing to concomitant NADH generation. Spectrophotometric substrate profiling of two wild-type ω-TAs of opposite stereoselectivity was carried out at 340 nm with 22 ketones, revealing subtle differences in substrate specificities that were consistent with docking simulation results obtained with cognate amines. Colorimetric readout for naked eye detection of the ω-TA activity was also demonstrated by supplementing the assay mixture with color-developing reagents whose color reaction could be quantified at 580 nm. The colorimetric assay was applied to substrate profiling of an engineered ω-TA for 24 ketones, leading to rapid identification of reactive ketones. The ALDH-based assay is expected to be promising for high-throughput screening of enzyme collections and mutant libraries to fish out the best ω-TA candidate as well as to tailor enzyme properties for efficient amination of a target ketone.

Rapid synthesis method of biomass-based amide

The invention discloses a rapid synthesis method of biomass-based amide, which comprises the steps: formamide is used as an amine source, formic acid is used as a hydrogen source, biomass aldehyde andketone is used as a raw material, the direct addition of formamide and aldehyde and ketone components and the reduction of formic acid is promoted to prepare the corresponding formamide derivative byrapidly heating under microwave-assisted heating and in the absence of a solvent and a catalyst; the formamide derivative is selectively converted to the corresponding primary amide by alcoholysis under the action of a base. The microwave assisted heating reaction system of the invention has higher catalytic efficiency than the corresponding oil bath system, greatly shortens the reaction time, remarkably improves the selectivity. The conversion rate of the biomass aldehyde or ketone compound is at least 99%, and the yield of the formamide derivative can reach 85 to 99%; the formamide can be synthesized by alcoholysis to obtain a primary amide with a yield of 92 to 99%.

Production of Primary Amines by Reductive Amination of Biomass-Derived Aldehydes/Ketones

Transformation of biomass into valuable nitrogen-containing compounds is highly desired, yet limited success has been achieved. Here we report an efficient catalyst system, partially reduced Ru/ZrO2, which could catalyze the reductive amination of a variety of biomass-derived aldehydes/ketones in aqueous ammonia. With this approach, a spectrum of renewable primary amines was produced in good to excellent yields. Moreover, we have demonstrated a two-step approach for production of ethanolamine, a large-market nitrogen-containing chemical, from lignocellulose in an overall yield of 10 %. Extensive characterizations showed that Ru/ZrO2-containing multivalence Ru association species worked as a bifunctional catalyst, with RuO2 as acidic promoter to facilitate the activation of carbonyl groups and Ru as active sites for the subsequent imine hydrogenation.

En Route to a Practical Primary Alcohol Deoxygenation

A long-standing scientific challenge in the field of alcohol deoxygenation has been direct catalytic sp3 C-O defunctionalization with high selectivity and efficiency, in the presence of other functionalities, such as free hydroxyl groups and amines widely present in biological molecules. Previously, the selectivity issue had been only addressed by classic multistep deoxygenation strategies with stoichiometric reagents. Herein, we propose a catalytic late-transition-metal-catalyzed redox design, on the basis of dehydrogenation/Wolff-Kishner (WK) reduction, to simultaneously tackle the challenges regarding step economy and selectivity. The early development of our hypothesis focuses on an iridium-catalyzed process efficient mainly with activated alcohols, which dictates harsh reaction conditions and thus limits its synthetic utility. Later, a significant advancement has been made on aliphatic primary alcohol deoxygenation by employing a ruthenium complex, with good functional group tolerance and exclusive selectivity under practical reaction conditions. Its synthetic utility is further illustrated by excellent efficiency as well as complete chemo- and regio-selectivity in both simple and complex molecular settings. Mechanistic discussion is also included with experimental supports. Overall, our current method successfully addresses the aforementioned challenges in the pertinent field, providing a practical redox-based approach to the direct sp3 C-O defunctionalization of aliphatic primary alcohols.

Selective synthesis of primary amines by reductive amination of ketones with ammonia over supported Pt catalysts

Supported platinum catalysts are studied for the reductive amination of ketones under ammonia and hydrogen. For a model reaction with 2-adamantanone, Pt-loaded MoOx/TiO2 (Pt-MoOx/TiO2) shows the highest yield of primary amine. The catalyst is effective for the selective transformation of various aliphatic and aromatic ketones to the corresponding primary amines, which demonstrates the first example of the selective synthesis of primary amines by this reaction. The yield of the amine increases with increase in the negative shift of the C￡O stretching band in the infrared spectra of adsorbed acetone on the catalysts, suggesting that Lewis acid sites on the support material play an important role in this catalytic system.

Asymmetric Amination of Secondary Alcohols by using a Redox-Neutral Two-Enzyme Cascade

Multienzyme cascade approaches for the synthesis of optically pure molecules from simple achiral compounds are desired. Herein, a cofactor self-sufficient cascade protocol for the asymmetric amination of racemic secondary alcohols to the corresponding chiral amines was successfully constructed by employing an alcohol dehydrogenase and a newly developed amine dehydrogenase. The compatibility and the identical cofactor dependence of the two enzymes led to an ingenious in situ cofactor recycling system in the one-pot synthesis. The artificial redox-neutral cascade process allowed the transformation of racemic secondary alcohols into enantiopure amines with considerable conversions (up to 94 %) and >99 % enantiomeric excess at the expense of only ammonia; this method thus represents a concise and efficient route for the asymmetric synthesis of chiral amines. If you know what amine: A redox-neutral two-enzyme cascade encompassing an alcohol dehydrogenase (ADH) and an amine dehydrogenase (AmDH) is constructed for the synthesis of chiral amines from the corresponding racemic alcohols in one pot to afford considerable conversions (up to 94 %) and high enantiomeric excess values (>99 %) at the expense of only ammonia.

Ring opening of pymisyl-protected aziridines with organocuprates

The pyrimidine-2-sulfonyl (pymisyl) group is introduced as a new protecting group that can be used to activate aziridines towards ring opening. It is readily introduced and removed under mild conditions. Regioselective ring opening of pymisyl-protected 2-methyl-aziridine with organocuprates gives the corresponding sulfonamides in high yields, and the pymisyl group can subsequently be removed upon treatment with a thiolate. The versatility of this new nitrogen protecting group is illustrated with a new synthesis of Selegiline, a monoamine oxidase-B inhibitor marketed for the treatment of Parkinson's disease. Easy on'easy off: The pymisyl group is introduced as a new protecting group for the activation of aziridines towards ring opening with organocuprates (see scheme). It is readily removed under very mild conditions with thiolates. The versatility of the approach is illustrated in a new synthesis of Selegiline, a drug marketed for the treatment of Parkinson's disease.

2-aminobenzoxazole derivatives and combinatorial libraries thereof

The present invention relates to novel 2-aminobenzoxazole derivative compounds of the following formula: wherein R1 to R4 and Z have the meanings provided herein. The invention further relates to combinatorial libraries containing two or more such compounds, as well as methods of preparing 2-aminobenzoxazole derivative compounds.