An insight into hexamethylenetetramine: a versatile reagent in organic synthesis

Kaur, Navjeet; Kishore, Dharma

doi:10.1007/s13738-013-0260-2

Cited by 30 publications

(8 citation statements)

References 77 publications

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“…Acidic hydrolysis (ethanolic HCl) converted the quaternary ammonium salt to the primary amine, bk‐2C‐B ( 6 ), in good yield (Figure ). This latter synthesis route employs the Delépine reaction to convert an alkyl halide to a primary amine, it has the advantages of cheap and easily available reagents, simple reaction conditions and apparatus and short reaction times …”

Section: Resultsmentioning

confidence: 99%

“…This latter synthesis route employs the Delépine reaction to convert an alkyl halide to a primary amine, it has the advantages of cheap and easily available reagents, simple reaction conditions and apparatus and short reaction times. [17,18] Interestingly, under the same conditions as used for bromination of 1-(4-bromo-2,5-dimethoxyphenyl)ethanone, the bromination of 1-(2,5-dimethoxyphenyl)ethanone yielded 2,2-dibromo-1-(2,5dimethoxyphenyl)ethanone. Bromination was confined to the side chain and not the aromatic ring, presumably, because the rate of aromatic bromination was slower than bromination at the α-position and there were two molar equivalents of bromine.…”

Section: Chemical Features and Analytical Characterizationmentioning

confidence: 99%

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Test purchase, identification and synthesis of 2‐amino‐1‐(4‐bromo‐2, 5‐dimethoxyphenyl)ethan‐1‐one (bk‐2C‐B)

Power

Kavanagh

O’Brien

et al. 2014

Drug Testing and Analysis

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2-Amino-1-(4-bromo-2,5-dimethoxyphenyl)ethan-1-one (bk-2C-B) has been recently offered for purchase by a variety of Internet retailers. This substance may be considered a cathinone analogue of the phenethylamine 2-(4-bromo-2,5-dimethoxyphenyl)ethan-1-amine (2C-B) which suggests that it may have psychoactive effects in humans. A test purchase of bk-2C-B was carried out and its identity was confirmed by a range of analytical techniques including nuclear magnetic resonance spectroscopy, gas and liquid chromatography, and high-resolution mass spectrometry. Confirmation was also obtained from the synthesis of bk-2C-B based on the implementation of the Delépine reaction in which the α-brominated intermediate was reacted with hexamethylenetetramine to afford the primary amine. Analysis of underivatized bk-2C-B by gas chromatography-mass spectrometry (GC-MS) showed that there was potential for artificial formation of 1-(4-bromo-2,5-dimethoxyphenyl)ethanone and a pyrazine dimer, these substances were not detected when employing liquid chromatographic analysis. Ion chromatography and X-ray crystallography analysis confirmed that the purchased bk-2C-B consisted of a hydrochloride and hydrobromide salt mixture, which indicated that it might have been prepared by the hexamethylenetetramine route followed by hydrochloric acid hydrolysis of the quaternary ammonium salt. X-ray crystallography also revealed that the purchased (mixed HCl/HBr salt) and synthesized bk-2C-B (HCl salt) exists as polymorphs.

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Section: Resultsmentioning

confidence: 99%

Section: Chemical Features and Analytical Characterizationmentioning

confidence: 99%

Test purchase, identification and synthesis of 2‐amino‐1‐(4‐bromo‐2, 5‐dimethoxyphenyl)ethan‐1‐one (bk‐2C‐B)

Power

Kavanagh

O’Brien

et al. 2014

Drug Testing and Analysis

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“…(i) The CFs were rstly extracted by Soxhlet with acetone in order to remove the polymer sizing and pollutants on the surface of CFs (denoted as untreated CF); 24 second, the CFs were oxidized in AgNO 3 /K 2 S 2 O 8 solution at 343 K for 1 h to introduce polar groups (such as hydroxyl groups, carboxyl groups); 25 subsequently, the CF-COOH was reacted with SOCl 2 for 48 h to yield acyl chloride functionalized CFs (CF-COCl); [26][27][28][29] CF-COCl was reacted with 3-bromo-1-propanol in anhydrous pyridine solution in the ice water bath, and then at room temperature for 3 h to yield CF-Br; [30][31][32][33] then 0.2 g CF-Br was reacted with 0.2 g hexamethylenetetramine (HMTA) in 30 mL trichloromethane at 333 K for 8 h to produce quaternary ammonium salt reaction and obtained functionalized CF containing the "rst generation" amine groups (CF-N + Br À , CF-G 1 -HMTA). 34,35 All reactions were extracted and washed by appropriate solvent. And every reaction step has been worked successfully by XPS.…”

Section: Surface Treatment Of Carbon Bermentioning

confidence: 99%

Interfacial properties and impact toughness of dendritic hexamethylenetetramine functionalized carbon fiber with varying chain lengths

Lian

Wang

et al. 2014

RSC Adv.

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“…Ammonium chloride (NH 4 Cl) affects the pH of the reaction of the reaction system in two ways. First NH 4 Cl reacts with formaldehyde to produce hexamethylenetetramine (CH 2 ) 6 N 4 , hydrochloric (HCl) acid and water [ 30 ] as presented in Eq. (6) .…”

Section: Introductionmentioning

confidence: 99%

Crop residues used as lignocellulose materials for particleboards formulation

Kariuki

Wachira

Kawira

et al. 2020

Heliyon

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Efforts to reduce pressure on use of wood in particleboard formulation have included the use of non-wood materials such as crop residues. Physical and mechanical properties are determined by the number of the hydroxyl (-OH) groups. Hydroxyl (-OH) groups attracts water molecules through hydrogen bonding affecting water absorption (WA) and thickness swelling (TS). WA and TS affect curing process of adhesive. Curing process of adhesives affects the mechanical characteristics of formulated particleboards. These challenges have been acted upon continuously through research. This review paper presents crop residues used as alternative lignocellulose material source in particleboard formulation and the various advances that have been made to improve on the properties of the resultant particleboards. Improvement over time of the non-wood material in composite materials focusses on increasing water resistance and compatibility between lignocellulose and binder. Crop residues-based are used in making medium and low density particleboards. These boards have shown good mechanical characteristics which include modulus of rupture (MOR), modulus of elasticity (MOE) and internal bonding (IB). MOR, MOE and IB have over time been improved by enhancing chemical compatibility of lignocellulose material and the binders. Water absorption and thickness swelling remain challenge. This review paper further explored various methods of improving water absorption and thickness swelling of crop-residue based particleboards.

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An insight into hexamethylenetetramine: a versatile reagent in organic synthesis

Cited by 30 publications

References 77 publications

Test purchase, identification and synthesis of 2‐amino‐1‐(4‐bromo‐2, 5‐dimethoxyphenyl)ethan‐1‐one (bk‐2C‐B)

Test purchase, identification and synthesis of 2‐amino‐1‐(4‐bromo‐2, 5‐dimethoxyphenyl)ethan‐1‐one (bk‐2C‐B)

Interfacial properties and impact toughness of dendritic hexamethylenetetramine functionalized carbon fiber with varying chain lengths

Crop residues used as lignocellulose materials for particleboards formulation

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