Hexylamine

Manufactured by Thermo Fisher Scientific

Sourced in Japan

Hexylamine is a colorless, flammable liquid used as a chemical building block in various industrial applications. It is a primary aliphatic amine with the molecular formula C6H15N. Hexylamine serves as a precursor in the synthesis of other chemicals and plays a role in the formulation of certain products, but its specific intended uses are not provided in this factual description.

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N-hexylamine (3 citations)

5 protocols using hexylamine

Synthesis of Diverse Aromatic Amines

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Butylamine (99 +%), pentylamine (99%), and hexylamine (99%) were purchased from Acros Organics (Morris Plains, NJ, USA). 3,5-dinitrobenzoyl chloride (DNBC) (96.5%), propylamine (98%), tert-Butylamine (99.5%), 4,4′-(hexafluoroisopropylidene) diphthalic anhydride (6FDA) (99%), anhydrous N,N-dimethylacetamide (DMAc) (99.8%), triethylamine (TEA) (99.5%), hydrazine monohydrate (80%), anhydrous pyridine (99.8%), and Pd/C (10%) were purchased from Sigma-Aldrich (Milwaukee, WI, USA). All other reagents and solvents were purchased commercially as analytical grade and used without further purification.

Rodríguez-González F.E., Pérez G., Niebla V., Jessop I., Martin-Trasanco R., Coll D., Ortiz P., Aguilar-Vega M., Tagle L.H., Terraza C.A, & Tundidor-Camba A. (2020). New Poly(imide)s Bearing Alkyl Side-Chains: A Study on the Impact of Size and Shape of Lateral Groups on Thermal, Mechanical, and Gas Transport Properties. Membranes, 10(7), 141.

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Synthesis and Characterization of Berberine Derivatives

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¹H and ¹³C NMR spectra were acquired on Bruker spectrometers AV-400 at 400.13 MHz (¹H) and 100.61 MHz (¹³C). Spectra were recorded in deuterated dimethyl sulfoxide (DMSO-d6); residual DMSO-d6 was used as a standard [δ(DMSO-d6) 2.50, δ(DMSO-d6) 39.51 ppm] for measuring for measuting chemical shifts δ in parts per million (ppm), J was measured in Hertz. The structure of the product was determined by means of ¹H and ¹³C NMR spectra and confirmed by MS spectrum. For the column chromatography, silica gel (60–200 mesh, Macherey–Nagel) was used. Mass-spectra was recorded at Bruker micrOTOF_Q using electrospray ionization (ESI). Spectral and analytical measurements were carried out at the Multi-Access Chemical Service Center of Siberian Branch of Russian Academy of Sciences (SB RAS). Berberine chloride hydrate was purchased from TCI Co. (Tokyo, Japan) and used after drying, hexylamine was purchased from Acros Organics (China) and used without additional purification.

Khvostov M.V., Gladkova E.D., Borisov S.A., Zhukova N.A., Marenina M.K., Meshkova Y.V., Luzina O.A., Tolstikova T.G, & Salakhutdinov N.F. (2021). Discovery of the First in Class 9-N-Berberine Derivative as Hypoglycemic Agent with Extra-Strong Action. Pharmaceutics, 13(12), 2138.

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Structural Analysis of Alkylated Berberine Derivatives

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The structure of the product was determined using ¹H and ¹³C NMR spectra. ¹H and ¹³C NMR spectra were recorded on Bruker AV-400 spectrometers (Bruker, Billerica, MA, USA) at 400.13 MHz (¹H) and 100.61 MHz (¹³C) in DMSO-d6. Mass spectra were recorded on a Bruker micrOTOFQ using electrospray ionization (ESI). Silica gel (60–200 mesh, Macherey–Nagel, Düren, Germany) was used for column chromatography; chloroform with gradient of ethanol was used as eluent. Berberine chloride hydrate (TCI Co. (Tokyo, Japan)) was used after oven drying at 95 °C for 5 h. Pentylamine, hexylamine, heptylamine, decylamine, and dodecylamine were purchased from Acros Organics (Geel, Belgium).

Khvostov M.V., Gladkova E.D., Borisov S.A., Fedotova M.S., Zhukova N.A., Marenina M.K., Meshkova Y.V., Valutsa N., Luzina O.A., Tolstikova T.G, & Salakhutdinov N.F. (2022). 9-N-n-alkyl Berberine Derivatives: Hypoglycemic Activity Evaluation. Pharmaceutics, 15(1), 44.

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Characterization of Softwood Kraft Pulp

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Softwood kraft
pulp (mixture of spruce and pine) was provided by UPM Kymmene Oyj
(Lappeenranta, Finland). The hemicellulose content was 8.5% calculated
from peak deconvolution of the C4 resonance in the ¹³C
solid-state NMR spectrum (Table S1) according
to Jusner et al.^{64 (link)} The calculated hemicellulose
content was in good agreement with the monosaccharide quantification
by methanolysis and gas chromatography (Table S2) according to Sundherg et al.^{65 (link),66 (link)} The molecular
weight was previously determined by multidetector GPC (Figure S3): M_n =
55 kDa, M_w = 614 kDa, M_z = 1651 kDa, and D̵ = 11.1. The
softwood kraft pulp was disintegrated in deionized water using a commercial
kitchen blender before use. Avicel (microcrystalline cellulose) with
a reported particle size of 50 μm (Sigma-Aldrich), sodium periodate
(≥99.8%; Sigma-Aldrich), 2-picoline borane (95%; Sigma-Aldrich),
tyramine (≥98.0%; TCI), ethanolamine (≥99.0%; Fluka
Analytical), butylamine (99.5%; Sigma-Aldrich), hexylamine (99%; Acros
Organics), and aniline (99%; Sigma-Aldrich) were purchased and used
without further purification.

Simon J., Fliri L., Sapkota J., Ristolainen M., Miller S.A., Hummel M., Rosenau T, & Potthast A. (2022). Reductive Amination of Dialdehyde Cellulose: Access to Renewable Thermoplastics. Biomacromolecules, 24(1), 166-177.

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Silver-Amine Complex Formation Protocol

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0.085 g of silver acetate (98 %, for synthesis, Merck, abbreviation: Ag(ac)) was dispersed in 20 ml ethanol (absolute, VWR) under stirring. The amine ligands were added dropwise in a 1:5 molar ratio (or 1:10 ratio) to the silver acetate and stirred until complete dissolution occurs, and a clear colorless solution is obtained. The employed amine ligands include hexylamine (99 %, Acros Organics), ethanolamine (>99.5 %, Sigma-Aldrich), 2-amino-2-methyl-1-propanol (> 99.0 %, Fluka), ammonia (25 % solution in water, pro analysis, Merck), morpholine (>99 %, for synthesis, Merck) and pyridine (99 %, extra pure, Acros Organics). Subsequently, formic acid (98 %, pro analysis, Sigma-Aldrich) was added to the mixture in a 1:1 molar ratio with silver acetate. This addition yields a miniscule amount of precipitation, which re-dissolves upon continuous stirring. The solution was transferred into a 50 ml volumetric flask and ethanol was added to obtain a 0.01 M silver solution.

Marchal W., Vandevenne G., D'Haen J., Calmont de Andrade Almeida A., Durand Sola M.A., van den Ham E.J., Drijkoningen J., Elen K., Deferme W., Van Bael M.K, & Hardy A. (2017). Ultrasonically spray coated silver layers from designed precursor inks for flexible electronics. Nanotechnology, 28(21).

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