110-68-9

Usage

Uses

Used in Chemical Synthesis:
N-METHYLBUTYLAMINE is used as an intermediate for the production of various chemicals. Its versatile chemical properties allow it to be a key component in the synthesis of a wide range of compounds.
Used in Pharmaceutical Industry:
N-METHYLBUTYLAMINE is used as a building block for the development of pharmaceutical compounds. Its unique structure enables it to be incorporated into drug molecules, potentially enhancing their efficacy and targeting specific biological pathways.
Used in Agrochemical Industry:
N-METHYLBUTYLAMINE is used as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its role in these applications is to provide a stable and effective platform for the development of compounds that can protect crops and enhance agricultural productivity.
Used in Diverse Industrial Applications:
N-METHYLBUTYLAMINE is used as a versatile building block in various industrial applications, including the production of surfactants, lubricants, and additives. Its chemical properties make it suitable for a wide range of uses, contributing to the development of innovative products and technologies.

Air & Water Reactions

Highly flammable. Slightly soluble in water.

Reactivity Profile

N-METHYLBUTYLAMINE 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.

Hazard

Flammable, dangerous fire risk.

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, skin contact, and intraperitoneal routes. Mildly toxic by inhalation. A skin and severe eye irritant. Flammable liquid when exposed to heat, sparks, or flame. To fight fire, use alcohol foam. When heated to decomposition it emits toxic fumes of NOx. See also AMINES.

Potential Exposure

Alert: (n-isomer): Possible risk of forming tumors, suspected of causing genetic defects, suspected reprotoxic hazard, Primary irritant (w/o allergic reaction), (sec-isomer): Drug. n-Butylamine is used in pharmaceuticals; dyestuffs, rubber, chemicals, emulsifying agents; photography, desizing agents for textiles; pesticides, and synthetic agents. sec-Butylamine is used as a fungistate. tert-Butylamine is used as a chemical intermediate in the production of tert-Butylaminoethyl methacrylate (a lube oil additive); as an intermediate in the production of rubber and in rust preventatives and emulsion deterrents in petroleum products. It is used in the manufacture of several drugs

Shipping

UN1125 n-Butylamine, Hazard Class: 3; Labels: 3—Flammable liquid, 8—Corrosive material. UN2014 Isobutylamine, Hazard Class: 3; Labels: 3—Flammable liquid, 8—Corrosive material

Incompatibilities

May form explosive mixture with air. May accumulate static electrical charges, and may causeignition of its vapors. n-Butylamine is a weak base; reacts with strong oxidizers and acids, causing fire and explosion hazard. Incompatible with organic anhydrides; isocyanates, vinyl acetate; acrylates, substituted allyls; alkylene oxides; epichlorohydrin, ketones, aldehydes, alcohols, glycols, phenols, cresols, caprolactum solution. Attacks some metals in presence of moisture. The tert-isomer will attack some forms of plastics

Waste Disposal

Use a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner andscrubber. All federal, state, and local environmental regulations must be observed.

InChI:InChI=1/C5H13N/c1-3-4-5-6-2/h6H,3-5H2,1-2H3/p+1

Upstream product

• 110-86-1 pyridine 
• 927-62-8 N,N-dimethylbutylamine 
• 94-36-0 dibenzoyl peroxide 
• 871-71-6 N-butylformamide 
• 6898-69-7 butylidene-methyl-amine 
• 31844-65-2 N-Butyl-N-methylbenzenemethanamine 
• 123-72-8 butyraldehyde 
• 74-89-5 methylamine 
• 109-65-9 1-bromo-butane 
• 542-69-8 1-iodo-butane 
• 593-51-1 methylamine hydrochloride 
• 123-73-9 crotonaldehyde 
• 103-67-3 benzyl-methyl-amine 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 1515-72-6 N-butylphthalimide 
• 3405-45-6 N-methyldibutylamine 
• 120-94-5 1-Methylpyrrolidine 
• 35204-33-2 N-(2-aminophenyl)-2-(N-methyl-N-n-butylamino)acetamide 
• 68504-75-6 2-[Butylmethylamino)-5-[1-hydroxy-2-[(1-methyl-3-phenylpropyl)-amino]ethyl]benzenesulphonamide 
• 51337-85-0 N-Butyl-2-[4-(4-chloro-phenoxy)-phenoxy]-N-methyl-propionamide 
• 53083-42-4 Butyl-methyl-carbamic acid 3-oxo-2-(2,4,6-trimethyl-phenyl)-3H-inden-1-yl ester 
• 91907-78-7 N-butyl-N-methyl-N'-phenylurea 
• 100-61-8 N-methylaniline 
• 512190-31-7 C₆H₅BClN(CH₃)(n-C₄H₉) 
• 52317-76-7 1-Butyl-3-(2,4-dimethyl-phenyl)-1-methyl-thiourea 
• 52317-80-3 3-(4-Bromo-2-methyl-phenyl)-1-butyl-1-methyl-thiourea 
• 57181-81-4 N-Butyl-2-chloro-N-methyl-3-[4-(1-phenyl-ethoxy)-phenyl]-propionamide 
• 16784-08-0 Rifamycin-B- 

Relevant academic research and scientific papers

Electron Transfer on the Photodehalogenation of 2-(4-chlorophenyl)benzoxazole Assisted by Amines

The photochemical reactivity of 2-(4-chlorophenyl)benzoxazole in the presence of a series of amines has been investigated.A fluorescence quenching study provides evidence for the formation of an exciplex between the singlet excited state of the benzoxazole derivative and the amine in its ground state.This exciplex gives rise to a charge-transfer complex (CTC).The quenching fluorescence date can be fitted by a Weller-Marcus system, thus leading to large reorganization energies.The measurment of dehalogenation, which is drastically increased in the presence of amines, allowed us to estimate the reactivity of the CTC.In the case of tertiary amines, 1percent of the CTC formed via the singlet state leads to the dehalogenation.For secondary amines a hydrogen transfer between the amine and the excited triplet state of the chloro compound is also postulated.

Isotopic probes for ruthenium-catalyzed olefin metathesis

Routes are described to previously unreported first- and second-generation Grubbs metathesis catalysts bearing a 13C label at the key benzylidene or methylidene site. Improved syntheses of the 2H-labelled isotopologues are also presented. Labelling at the alkylidene position is important because it provides unique, direct information about changes at the active site of the catalyst, and the fate of the [Ru]CHR ligand during catalyst deactivation. A case study demonstrates the power of 13C-labelling in tracking the methylidene moiety in amine-induced decomposition of the second-generation complex RuCl2(PCy3)(H2IMes)(13CH2). Also reported is the solubility of ethylene in C6D6 and CD2Cl2, measured at 296 ± 1.5 K and 101.0 ± 0.8 kPa. This journal is

SPECIFIC ACID CATALYSIS IN THE DECOMPOSITION OF TRIALKYLTRIAZENES.

The acid-catalyzed decomposition of 1,3-di-n-butyl-3-methyltriazene (1) in aqueous buffer was investigated. Determination of the kinetics over a pH range of 10. 4 to 12 indicated that the reaction is acid catalyzed. Variation of buffer concentration, at constant ionic strength, produced an insignificant variation in the rate constant. The determination of kinetics of the decomposition of 1 in nine different buffers, ranging in pK//a from 9. 6 to 12. 7, also gave negligible variation in the rate constants. The solvent isotope effect for the reaction, k//H/k//D, was 0. 62. These data strongly support the conclusion that the reaction is specific acid catalyzed. This implies that the reaction involves fast, reversible protonation of the triazene followed by the rate-determining heterolysis of the protonated species to n-butyldiazonium ion and n-butylmethylamine.

A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics

The kinetics of quinuclidine displacement of BH3 from a wide range of Lewis base borane adducts have been measured. Parameterization of these rates has enabled the development of a nucleofugality scale (NFB), shown to quantify and predict the leaving group ability of a range of other Lewis bases. Additivity observed across a number of series R′3-nRnX (X = P, N; R′ = aryl, alkyl) has allowed the formulation of related substituent parameters (nfPB, nfAB), providing a means of calculating NFB values for a range of Lewis bases that extends far beyond those experimentally derived. The utility of the nucleofugality parameter is explored by the correlation of the substituent parameter nfPB with the hydrolyses rates of a series of alkyl and aryl MIDA boronates under neutral conditions. This has allowed the identification of MIDA boronates with heteroatoms proximal to the reacting center, showing unusual kinetic lability or stability to hydrolysis.

Photometric Characterization of the Reductive Amination Scope of the Imine Reductases from Streptomyces tsukubaensis and Streptomyces ipomoeae

Imine reductases (IREDs) have emerged as promising enzymes for the asymmetric synthesis of secondary and tertiary amines starting from carbonyl substrates. Screening the substrate specificity of the reductive amination reaction is usually performed by time-consuming GC analytics. We found two highly active IREDs in our enzyme collection, IR-20 from Streptomyces tsukubaensis and IR-Sip from Streptomyces ipomoeae, that allowed a comprehensive substrate screening with a photometric NADPH assay. We screened 39 carbonyl substrates combined with 17 amines as nucleophiles. Activity data from 663 combinations provided a clear picture about substrate specificity and capabilities in the reductive amination of these enzymes. Besides aliphatic aldehydes, the IREDs accepted various cyclic (C4–C8) and acyclic ketones, preferentially with methylamine. IR-Sip also accepted a range of primary and secondary amines as nucleophiles. In biocatalytic reactions, IR-Sip converted (R)-3-methylcyclohexanone with dimethylamine or pyrrolidine with high diastereoselectivity (>94–96 % de). The nucleophile acceptor spectrum depended on the carbonyl substrate employed. The conversion of well-accepted substrates could also be detected if crude lysates were employed as the enzyme source.

Copper(II)-Catalyzed Selective Reductive Methylation of Amines with Formic Acid: An Option for Indirect Utilization of CO2

A copper-catalyzed protocol for reductive methylation of amines and imine with formic acid as a C1 source and phenylsilane as a reductant is reported for the first time, affording the corresponding methylamines in good to excellent yields under mild conditions. This protocol offers an alternative method for indirect utilization of CO2, as formic acid can be readily obtained from hydrogenation of CO2.

N-Methylation of amines with methanol in a hydrogen free system on a combined Al2O3-mordenite catalyst

N-Methyl amines play a major role in the production of medicines, pesticides, surfactants and dyes. N-Methylation of primary or second amines with methanol is considered to be a green path for the synthesis of N-methyl amines and the catalyst is key. In this article, the combined Al2O3-mordenite catalyst (mass fraction of alumina is 40%) with good activity, selectivity, lifetime and stability was prepared for N-methylation of various amines with methanol in a hydrogen free system in a fixed bed reactor, and characterized by XRD, N2 adsorption and NH3-TPD. Furthermore, the methanol adsorption was investigated by in situ FTIR, and the result indicated that methoxyl species may be the active species for the N-methylation of amines.

Selective N-methylation of aliphatic amines with CO2 and hydrosilanes using nickel-phosphine catalysts

A method using CO2 and PhSiH3 for the methylation of primary and secondary aliphatic amines catalyzed by Ni (0) complexes was developed, selectively producing the monomethylated products in moderate to good yields. For that purpose, two catalysts were used: [(dippe)Ni(μ-H)]2 and the commercially available Ni(COD)2/dcype, both of which were rather efficient in this process. With a slight experimental modification, the reaction allowed the production of monomethylated ureas in good yields by using low amounts of PhSiH3. On the basis of the experimental results, we propose a possible reaction mechanism for the formation of the new C-N bond.

Catalytic hydrogenation of amides to amines under mild conditions

Under (not so much) pressure: A general method for the hydrogenation of tertiary and secondary amides to amines with excellent selectivity using a bimetallic Pd-Re catalyst has been developed. The reaction proceeds under low pressure and comparatively low temperature. This method provides organic chemists with a simple and reliable tool for the synthesis of amines. Copyright

Reactivity of the insecticide fenitrothion toward O and N nucleophiles

The reactivity of Fenitrothion (1) toward several O- and N-based nucleophiles, including ambident and α-nucleophiles, was investigated in basic media at 25 °C in water containing 2% 1,4-dioxane. In the reactions with HO- and HOO- quantitative formation of 3-methyl-4-nitrophenoxide (2) was observed indicating a SN2(P) pathway. In the reactions with NH2OH, NH2O-, and BuNH2, demethylfenitrothion (4) was formed along with 2, indicating competition between the SN2(P) and SN2(C) pathways; no evidence of a SNAr pathway was observed in any case. The observed rate constants were dissected into the values corresponding to the SN2(P) and SN2(C) pathways. The yield of 4 depends on the nucleophile and on the pH of the reaction, being the main product in the case of BuNH2. With HOO-, NH2OH, and NH 2O- a significant α-effect was observed, confirming the participation of the nucleophile in the rate-limiting step of the reaction.