76716-21-7

Usage

Type of compound

Hydrochloride salt of 1-methyl-butylamine

Structure

Primary amine with a methyl group attached to the nitrogen atom

Uses

Synthesis of pharmaceuticals, agrochemicals, and other organic compounds; precursor to industrial chemicals; reagent in organic chemistry reactions; key intermediate in production of surfactants and corrosion inhibitors

Physical properties

Colorless to pale yellow liquid; strong ammonia-like odor; soluble in water

Upstream product

• 85231-72-7 (1-Methyl-butyl)-phosphoramidic acid diethyl ester 
• 109-67-1 1-penten 
• 627-19-0 1-Pentyne 
• 109-66-0 pentane 
• 107-87-9 2-Pentanone 
• 625-30-9 2-pentylamine 
• 107-81-3 2-bromopentane 
• 73746-39-1 2-pentylazide 
• 4551-09-1 pentan-2-yl methanesulfonate 
• 6032-29-7 (+/-)-2-pentanol 
• 102095-59-0 C₁₄H₃₀NO₅P 
• 76716-19-3 C₁₇H₂₂NOP 
• 146039-15-8 1-Methyl-butyl-phosphorimidic acid triethyl ester 

Downstream Products

• 512847-56-2 [4-(2,4-dichloro-phenyl)-3-nitro-pyridin-2-yl]-(1-methyl-butyl)-amine 
• 101689-14-9 C₁₅H₂₀F₃NO₂ 

Relevant academic research and scientific papers

Cerium-Catalyzed C-H Functionalizations of Alkanes Utilizing Alcohols as Hydrogen Atom Transfer Agents

Modern photoredox catalysis has traditionally relied upon metal-to-ligand charge-transfer (MLCT) excitation of metal polypyridyl complexes for the utilization of light energy for the activation of organic substrates. Here, we demonstrate the catalytic application of ligand-to-metal charge-transfer (LMCT) excitation of cerium alkoxide complexes for the facile activation of alkanes utilizing abundant and inexpensive cerium trichloride as the catalyst. As demonstrated by cerium-catalyzed C-H amination and the alkylation of hydrocarbons, this reaction manifold has enabled the facile use of abundant alcohols as practical and selective hydrogen atom transfer (HAT) agents via the direct access of energetically challenging alkoxy radicals. Furthermore, the LMCT excitation event has been investigated through a series of spectroscopic experiments, revealing a rapid bond homolysis process and an effective production of alkoxy radicals, collectively ruling out the LMCT/homolysis event as the rate-determining step of this C-H functionalization.

Synthesis method of primary amine hydrochloride

The invention discloses a synthesis method of primary amine hydrochloride. According to the synthesis method, in the presence of a gold complex, water and alkyne carry out catalytic hydrolysis to generate ketones, and then ketones and ammonium formate are catalyzed by a rhodium complex to generate primary amine. Compared with a conventional primary amine synthesis method, the synthesis method hasthe advantages that no alkali is added during the reaction process, no side product is generated, the atomic economy is good, the reaction conditions are mild, and the synthesis method has a wide prospect.

Development of an in situ-Product Crystallization (ISPC)-Concept to Shift the Reaction Equilibria of Selected Amine Transaminase-Catalyzed Reactions

The synthesis of enantiopure amines via amine transaminases involves several challenges including unfavorable reaction equilibria and product inhibition. Described here is a non-catalytic approach to overcome such problems by using an in situ-product crystallization (ISPC) to selectively remove a targeted product amine from an amine transaminase-catalyzed reaction. The continuous removal of the product amine from its reaction solution as a barely soluble salt effectively yields a displacement of the reaction equilibrium towards the products and facilitates a simple downstream processing approach via filtration. The targeted product amine is eventually obtained from the salt, while the counterion compound can be easily recycled.

Synthesis of primary sec-alkylamines via nucleophilic ring-opening of N-phosphorylated aziridines

The novel ring-opening reaction of various 2-alkyl- and 2,2-dimethyl-N-(diethoxyphosphoryl)aziridines (1) and (10) with copper-modified Grignard reagents proceeds regiospecifically at the less hindered carbon. The diethyl N-sec-alkylphosphoramidates (2) thus obtained may efficiently be converted to primary sec-alkylamine hydrochlorides (3) by refluxing with 20% hydrochloric acid. 2,3-Disubstituted N-phosphorylated aziridines except N-phosphorylated cyclohexenimine (4) do not react under the described conditions. Copper-mediated reaction of 2-phenyl-N-(diethoxyphosphoryl)aziridine (7) with Grignard reagents affords a mixture of regioisomers (8) and (9) but still with the preference of ring-opening at the carbon of lesser substitution.

TRIETHYL PHOSPHITE IN ORGANIC SYNTHESIS. A FACILE, ONE-POT CONVERSION OF ALCOHOLS INTO AMINES

General protocols for converting primary, secondary, and tertiary alcohols into the corresponding primary amines are presented.

Optimized procedures for one-pot conversion of alkyl bromides into amines via the Staudinger reaction

New optimized procedures for transforming primary and secondary alkyl bromides into the corresponding primary amine salts have been elaborated. Essential modifications of azidation and deprotection of intermediate triethoxyphosphine alkylimides resulted in substantial improvement of the overall yields. Conversion of ammonium tosylates and hydrochlorides into free amines in a nonaqueous medium is described.

Conversion of Alcohols into Primary Amines, a New Mitsunobu Version of Gabriel-type Synthesis

Primaere und sekundaere Alkohole liefern die entsprechenden Amin-hydrochloride 3 mit guten Ausbeuten (60-85percent), wenn sie unter milden Bedingungen mit N-(Diethoxyphosphoryl)-carbamidsaeure-tert-butylester (1) in Gegenwart von Azodicarbonsaeure-diethylester/Triphenylphosphan umgesetzt und danach die entstandenen N-Alkyl-N-(diethoxyphosphoryl)carbamidsaeureester 2 mit gasfoermigem HCl gespalten werden.Die Stereochemie dieser Reaktion wird untersucht.