2086-26-2 Usage
Chemical Properties
LIGHT YELLOW POWDER
Uses
Different sources of media describe the Uses of 2086-26-2 differently. You can refer to the following data:
1. As a strong UV chromophore, O-(4-Nitrobenzyl)hydroxylamine hydrochloride can be used in derivatization of reducing sugars for ultraviolet absorption detection in HPLC analyses.
2. A strong UV chromophore used in derivatization of reducing sugars for ultraviolet absorption detection in HPLC analyses.
Preparation
To a solution of 25 gm (0.183 mole) of benzohydroxamic acid in 28 ml of ethanol and 10.2 gm (0.184 mole) of potassium hydroxide in 40 ml of water is added a hot solution of 39.4 gm (0.184 mole) of p-nitrobenzyl bromide in ethanol. The mixture is then heated under a reflux condenser for 45 min and cooled. The precipitated crystals are separated and crystallized from ethanol. (No yield reported.) A solution of 15 gm (0.055 mole) of the above o-p-nitrobenzylbenzohy-droxamic acid (p-nitrobenzyl benzohydroxamate) in 125 ml of hot ethanol is heated to reflux for 25 min with 150 ml of cone, hydrochloric acid. To prevent the precipitation of the final product during the work-up, the following steps are carried out rapidly. The clear solution is diluted with 150 ml of water and while still warm benzoic acid and other by-products are separated by extraction with 200 ml of chloroform. The aqueous layer is evaporated to dryness under reduced pressure to afford a crude yield of 10.75 gm (96%). The residue is recrys-tallized from hot 2 Ν hydrochloric acid and washed in turn with ethanol and with ether to afford a solid, m.p. 217°C.
The free base may be produced by neutralizing the salt with sodium carbonate solution; O-p-nitrobenzylhydroxylamine, m.p. 56°C (recrystal-lized from petroleum ether). By a similar technique, O-allylhydroxylamine hydrochloride, m.p. 172°C (dec.) was also prepared.
An examination of the product of butylating benzohydroxamic acid showed that a nonacidic fraction and an equal weight of an acidic fraction were readily isolated. The nonacidic fraction contained mainly Ο, Ο '-dibutyl benzohydroxi-mate (b.p. 175-180°C/13 mm Hg) and some aniline (probably formed during the reaction by a Lossen rearrangement). On hydrolysis with eth-anolic hydrochloric acid, the hydroximate produced ethyl benzoate and O-butylhydroxylamine hydrobromide (m.p. 159-161°C; hydrochloride, m.p. 156-157°C).
The acidic fraction contained mainly O-butylbenzohydroxamic acid (butyl benzohydroxamate) which on hydrolysis formed O-butylhydrox-ylamine hydrochloride and benzoic acid. It has been contended that in this particular work, the presence of an Ν,Ο-dibutylbenzohy-droxamic acid had been overlooked. The major source of O-butylhy-droxylamine hydrochloride is from the acidic fraction, although the yield is not particularly high. The initial preparation of the butylated benzohydroxamic acid deriva-tives has been repeated recently. The analysis of the reaction products by vapor-phase chromatography showed it to contain 43% of O-butyl-benzohydroxamic acid (butyl benzohydroxamate), 17% of iV,0-dibutyl-benzohydroxamic acid, and 8% of n-butyl(Z)-0-n-butylbenzohydroximate:
The nature of the remaining 32% of the crude reaction product was not determined. The use of benzohydroxamic acid has been extended to the preparation of a variety of O-substituted hydroxylamines. For example, halocarboxylic acids have been used as alkylating agents to produce α-aminooxy acids of the type, NH20(CH2)?C02H.
A variety of O-benzylhydroxylamines, O-aralkylhydroxylamines, as well as simpler O-substituted hydroxylamines have also been prepared. In some of these prepara-tions, the hydrolysis of the O-substituted benzohydroxamic acid was car-ried out with hot alcoholic hydrogen chloride. This treatment evidently prevented the O-N cleavage which had been observed during the aqueous hydrolysis of the substituted benzohydroxamic acids.
Check Digit Verification of cas no
The CAS Registry Mumber 2086-26-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,0,8 and 6 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 2086-26:
(6*2)+(5*0)+(4*8)+(3*6)+(2*2)+(1*6)=72
72 % 10 = 2
So 2086-26-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H8N2O3/c8-12-5-6-1-3-7(4-2-6)9(10)11/h1-4H,5,8H2
2086-26-2Relevant articles and documents
Palladium-catalyzed regio- And stereoselective access to allyl ureas/carbamates: Facile synthesis of imidazolidinones and oxazepinones
Banerjee, Prabal,Saha, Debarshi,Taily, Irshad Maajid
supporting information, p. 6564 - 6570 (2020/11/10)
Typically, transition metal catalysis enforces the stereodefined outcome of a reaction. Here we disclose the palladium-catalyzed regio- and stereoselective access to allylic ureas/carbamates and their further exploitation to diverse cyclic structures under operationally simple reaction conditions. This protocol features palladium-catalyzed decarboxylative amidation of highly modular VECs with good to excellent yield, minimal waste production, wide substrate scope, and low catalyst loading. In follow-up chemistry, we demonstrated the debenzylation of vinylic imidazolidinones to N-hydroxycyclic ureas and regioselective derivatization towards the facile synthesis of halohydrins and oxiranes under mild reaction conditions in good to excellent yields. This journal is
Design, synthesis and evaluation of oxime-functionalized nitrofuranylamides as novel antitubercular agents
Fan, Yi-Lei,Wu, Jian-Bing,Ke, Xing,Huang, Zhong-Ping
supporting information, p. 3064 - 3066 (2018/08/21)
A series of oxime-functionalized nitrofuranylamides were designed, synthesized and evaluated for their in vitro anti-mycobacterial activities against MTB H37Rv and drug-resistant clinical isolates. Among them, two compounds 7a and 7b exhibited excellent activity against the three tested strains. Both of them were comparable to the first-line anti-TB agents INH and RIF against MTB H37Rv, and were far more potent than INH and RIF against MDR-TB 16833 and 16995 strains. Thus, both of them could act as leads for further optimization.
NOVEL VASCULAR LEAKAGEAGE INHIBITOR
-
, (2015/01/07)
The present disclosure relates to a novel vascular leakage inhibitor. The novel vascular leakage inhibitor of the present invention inhibits the apoptosis of vascular endothelial cells, inhibits the formation of actin stress fibers induced by VEGF, and enhances the cortical actin ring structure, thereby inhibiting vascular leakage. Accordingly, the vascular leakage inhibitor of the present invention can prevent or treat various diseases caused by vascular leakage. Since the vascular leakage inhibitor of the present invention is synthesized from commercially available or easily synthesizable pregnenolones, it has remarkably superior feasibility of commercial synthesis.
