927-62-8

Basic information

• Product Name: N,N-Dimethylaminobutane
• Synonyms: 1-Butanamine,N,N-dimethyl-;ar84996;Butylamine, N,N-dimethyl-;Butyldimethylamine;butyl-dimethyl-amine;n,n-dimethyl-1-butanamin;N,N-Dimethyl-1-butanamine;n,n-dimethyl-butylamin
• CAS NO: 927-62-8
• Molecular Formula: C₆H₁₅N
• Molecular Weight: 101.19
• EINECS: 213-156-1
• Mol File: 927-62-8.mol
• Article Data: 32

Chemical Properties

• Melting Point: -60 °C
• Boiling Point: 93.3 °C750 mm Hg(lit.)
• Flash Point: 25 °F
• Appearance: colourless liquid
• Density: 0.721 g/mL at 25 °C(lit.)
• Vapor Pressure: 44.6mmHg at 25°C
• Refractive Index: n20/D 1.398(lit.)
• PKA: 9.83±0.28(Predicted)
• Water Solubility: 3.4 g/100 mL (20 ºC)
• Stability: Stable. Incompatible with strong oxidizing agents, strong acids. Highly flammable - note low flashpoint.
• CAS DataBase Reference: N,N-Dimethylaminobutane(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Dimethylaminobutane(927-62-8)
• EPA Substance Registry System: N,N-Dimethylaminobutane(927-62-8)

Safety Data

• Hazard Codes: F,C
• Statements: 11-20/22-34
• Safety Statements: 26-36/37/39-45-16
• RIDADR: UN 2733 3/PG 2
• WGK Germany: 1
• RTECS: EJ4039250
• F: 9-34
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 927-62-8(Hazardous Substances Data)

Usage

Description

N,N-Dimethylaminobutane, also known as Dimethylbutylamine, is a tertiary amine with a dimethylamino substituent at the 1-position of n-butane. It is a colorless liquid with an ammonia-like odor and has a flash point of 20°F, a boiling point of 201°F, and a density of 0.72 g/cm3. Ingestion, inhalation, and contact with skin or eyes can cause irritation, burns, or other adverse effects.

Uses

Used as a Chemical Intermediate:
N,N-Dimethylaminobutane is used as a chemical intermediate for the synthesis of various compounds and materials.
Used in High-Density Rigid Flame-Retardant Polyimide Foam Material Preparation:
N,N-Dimethylaminobutane is used in the preparation of high-density rigid flame-retardant polyimide foam material, contributing to its flame-retardant properties.
Used in Fabrication of Polystyrene-Based Nano-LC Monolithic Columns:
N,N-Dimethylaminobutane is suitable for use in the fabrication of polystyrene-based nano-liquid chromatography (nano-LC) monolithic columns for the separation of protein molecules.
Used as an Ion-Pairing Reagent in Oligonucleotide LC/MS:
N,N-Dimethylaminobutane may be used as an ion-pairing reagent in a study involving the comparison of performance of six ion-pairing reagents as mobile phase modifiers for oligonucleotide liquid chromatography/mass spectrometry (LC/MS).

Synthesis Reference(s)

Journal of the American Chemical Society, 106, p. 7122, 1984 DOI: 10.1021/ja00335a042

Air & Water Reactions

Highly flammable. Partially soluble in water.

Reactivity Profile

N,N-DIMETHYL-N-BUTYLAMINE 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

Moderately toxic by ingestion. Low toxic- ity by inhalation and skin contact. A moderate eye irritant.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C6H15N/c1-4-5-6-7(2)3/h4-6H2,1-3H3/p+1

Upstream product

• 7685-30-5 N,N,N-trimethylbutylamine ion 
• 760-79-2 N,N-dimethylbutyramide 
• 63951-24-6 n-butyltrimethylammonium hydroxyde 
• 7722-19-2 trimethylbutylammonium iodide 
• 141-43-5 ethanolamine 
• 542-69-8 1-iodo-butane 
• 124-40-3 dimethyl amine 
• 187737-37-7 propene 
• 109-69-3 n-Butyl chloride 
• 55831-89-5 4-(dimethylamino)-1-butene 
• 67-56-1 methanol 
• 110-68-9 N-n-butyl-N-methylamine 
• 109-73-9 N-butylamine 
• 762-04-9 phosphonic acid diethyl ester 

Downstream Products

• 132493-67-5 butyl-[2-(4-chloro-phenoxy)-ethyl]-dimethyl-ammonium; bromide 
• 132493-60-8 butyl-[2-(2-chloro-phenoxy)-ethyl]-dimethyl-ammonium; bromide 
• 109963-50-0 butyl-[2-(4-hydroxy-phenoxy)-ethyl]-dimethyl-ammonium; bromide 
• 109411-67-8 butyl-dimethyl-(2-phenoxy-ethyl)-ammonium; bromide 
• 75-50-3 trimethylamine 
• 4359-97-1 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxy-benzylidene)-cyclohexa-2,5-dienone 
• 106-98-9 1-butylene 
• 3405-45-6 N-methyldibutylamine 
• 123-72-8 butyraldehyde 
• 124-40-3 dimethyl amine 
• 72617-58-4 tris(N,N-dimethylbutyl)benzylammonium chloride 
• 38697-54-0 (2-Benzhydryloxy-ethyl)-butyl-dimethyl-ammonium; bromide 
• 38697-61-9 Butyl-(3-carbamoyl-3,3-diphenyl-propyl)-dimethyl-ammonium; bromide 
• 1117-72-2 N-methyl-N-n-butylformamide 

Relevant articles and documents

Palladium-Assisted Amination of Olefins. A Mechanistic Study

The mechanism of the palladium-assisted amination of olefins has been studied by low-temperature NMR and ultraviolat spectroscopy, conductivity measurements, and stoichiometry and exchange studies.The specific sequence of steps followed strongly depends on the temperature of amine.With dimethylamine, the sequence consists of cleavage of the chloride bridge by the amine to give a single olefin-palladium-amine complex (2).This undergoes amination of the olefin and concomitant cyclization to form the β-aminoalkylpalladium complex (3) directly and dimethylammonium hydrochloride.In contrast, with diethylamine, the initially formed olefin-palladium-amine complex undergoes amination to form a discrete zwitterionic complex (6).This reacts slowly with additional added amine to give the chelating β-aminoalkylpalladium complex (7).

Zirconium-hydride-catalyzed site-selective hydroboration of amides for the synthesis of amines: Mechanism, scope, and application

Developing mild and efficient catalytic methods for the selective synthesis of amines is a longstanding research objective. In this respect, catalytic deoxygenative amide reduction has proven to be promising but challenging, as this approach necessitates selective C–O bond cleavage. Herein, we report the selective hydroboration of primary, secondary, and tertiary amides at room temperature catalyzed by an earth-abundant-metal catalyst, Zr-H, for accessing diverse amines. Various readily reducible functional groups, such as esters, alkynes, and alkenes, were well tolerated. Furthermore, the methodology was extended to the synthesis of bio- and drug-derived amines. Detailed mechanistic studies revealed a reaction pathway entailing aldehyde and amido complex formation via an unusual C–N bond cleavage-reformation process, followed by C–O bond cleavage.

Ionic liquid/H2O-mediated synthesis of mesoporous organic polymers and their application in methylation of amines

Mesoporous Tr?ger's base-functionalized polymers (Meso-TBPs) were prepared using a sulfonic acid group functionalized ionic liquid/H2O system, with surface areas up to 431 m2 g-1 and pore sizes of 3-15 nm. Ir(ii) coordinated Meso-TBPs exhibited extraordinary catalytic performance in the N-methylation of amines using methanol.