4747-21-1

Basic information

• Product Name: N-Isopropylmethylamine
• Synonyms: 2-(Methylamino)propane;2-Methylaminopropane;2-Propanamine,N-methyl-;Ethylamine, N,1-dimethyl-;Ethylamine,N,1-dimethyl-;Isopropylmethylamine;isopropyl-methyl-amine;N,1-Dimethylethylamine
• CAS NO: 4747-21-1
• Molecular Formula: C₄H₁₁N
• Molecular Weight: 73.14
• EINECS: 225-266-7
• Product Categories: Polyamines;Aliphatics;Amines;Miscellaneous Reagents;Building Blocks;C2 to C5;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 4747-21-1.mol
• Article Data: 19

Chemical Properties

• Melting Point: -55.1°C (estimate)
• Boiling Point: 50-53 °C(lit.)
• Flash Point: −25 °F
• Appearance: Colorless/Liquid
• Density: 0.702 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.15 psi ( 20 °C)
• Refractive Index: n20/D 1.384(lit.)
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: Soluble in chloroform, DMSO, methanol.
• PKA: 10.76±0.10(Predicted)
• Sensitive: Air Sensitive
• BRN: 1730877
• CAS DataBase Reference: N-Isopropylmethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Isopropylmethylamine(4747-21-1)
• EPA Substance Registry System: N-Isopropylmethylamine(4747-21-1)

Safety Data

• Hazard Codes: F,C
• Statements: 11-34
• Safety Statements: 16-26-36/37/39-45
• RIDADR: UN 2734 8/PG 1
• WGK Germany: 3
• F: 9-23
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 4747-21-1(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

Uses

N-Isopropylmethylamine is used in the generation of in situ micelles having distinct sizes, by sequential self-assembly of a series of stimuli-responsive amphiphilic block copolymers, prepared by reversible addition-fragmentation chain transfer (RAFT) polymerization. It is suitable for use in the synthesis of novel 5-ethoxy-N,N-dialkyl-[α,α,β,β-H4]-tryptamines and their [α,α,β,β,β-D4]-counterparts following the Speeter and Anthony procedure.

General Description

N-Isopropylmethylamine is an unsymmetrical amine. Pd/C-catalyzed oxidative cross double carbonylation of N-isopropylmethylamine with alcohols has been reported.

Flammability and Explosibility

Highlyflammable

InChI:InChI=1/C4H11N/c1-4(2)5-3/h4-5H,1-3H3

Upstream product

• 110-86-1 pyridine 
• 996-35-0 N,N-dimethylisopropyl amine 
• 94-36-0 dibenzoyl peroxide 
• 67-64-1 acetone 
• 74-89-5 methylamine 
• 6852-56-8 N-benzylideneisopropylamine 
• 77-78-1 dimethyl sulfate 
• 10556-98-6 1,3,5-Triisopropyl-1,3,5-triazacyclohexane 
• 91076-68-5 mono-trimethylsilylphosphite 
• 2594-20-9 ethyl N-isopropylcarbamate 
• 519-73-3 triphenylmethane 
• 82881-55-8 lithium isopropyl(methyl)amide 
• 593-51-1 methylamine hydrochloride 
• 72552-73-9 N-2-propylidenemethanamide N-oxide 

Downstream Products

• 2893-49-4 N-methyl-N-isopropylaminoethyl alcohol 
• 25244-11-5 2-(isopropyl-methyl-amino)-1-phenyl-ethanol 
• 860572-38-9 N-isopropyl-N-methyl-β-alanine ethyl ester 
• 6712-59-0 5-(4-chloro-phenyl)-1-isopropyl-1-methyl-biguanide 
• 30533-08-5 N-methyl-N-nitroso-2-propanamine 
• 23580-89-4 methyl-(3-phenyl-propyl)-amine 
• 87462-11-1 N-isopropyl-3-phenylpropan-1-amine 

Relevant articles and documents

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Reviving electrocatalytic reductive amination: A sustainable route from biogenic levulinic acid to 1,5-dimethyl-2-pyrrolidone

The electrocatalytic reductive amination offers a green pathway to N-containing platform and fine chemicals by using water as a hydrogen source and benign reaction conditions. However, systematic studies about suitable reaction conditions and application to biogenic substrates are rare. Here, we present the electrochemical transformation of levulinic acid to 1,5-dimethyl-2-pyrrolidone. Data from Smirnov et al. for the amination of conventional ketones were validated and extended by systematically investigating the impact of electrode material, substrate concentration, current density, solvent, electrolyte, and pH value. High substrate concentrations in an aqueous electrolyte with a high pH value enable imine formation and copper is identified as the most selective cathode material at current densities lower than 40 mA cm-2. The application of optimized reaction conditions to levulinic acid, followed by a short heating procedure for dehydrative ring closure, led to 1,5-dimethyl-2-pyrrolidone in 78% yield. The systematic approach of this work presents the first example of an electrochemical levulinic acid amination and provides a methodology for the benign synthesis of other N-containing species. This journal is

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.