Acetanilide - CAS 103-84-4
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
Acetanilide
Catalog Number:
103-84-4
Synonyms:
Antifebrin
CAS Number:
103-84-4
Description:
Acetanilide is an aniline derivative and has possess analgesic.
Molecular Weight:
135.16
Molecular Formula:
C8H9NO
COA:
Inquire
MSDS:
Inquire
Chemical Structure
CAS 103-84-4 Acetanilide

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Reference Reading


1. Study of the Beckmann rearrangement of acetophenone oxime over porous solids by means of solid state NMR spectroscopy
Ana Belen Fernandez, Ines Lezcano-Gonzalez, Mercedes Boronat, Teresa Blasco*, and Avelino Corma. Phys. Chem. Chem. Phys., 2009, 11, 5134–5141
The reaction product of the Beckmann rearrangement of acetophenone oxime is acetanilide, which results from the migration of the phenyl group in the anti position with respect to the hydroxyl group. Although this reaction is highly stereospecific, we have also considered the N-methyl benzamide (NMB) isomer, as it has been reported to appear as a by-product of the rearrangement of acetophenone oxime. Accordingly, we have optimized the adsorption complexes of the two amides, acetanilide and NMB, on silanol (Acetanilide/Silanol and NMB/Silanol) and bridging Si–OH–Al (Acetanilide/Brønsted and NMB/Brønsted) zeolite groups, and obtained the models depicted in Scheme 1. The 15N and 13C (the 13C-carbonyl group) NMR chemical shifts and adsorption energies, calculated using density functional methods, are summarized in Table 1. The distances between the amides and zeolite hydroxyl groups, depicted in the models of Scheme 1, are consistent with the formation of hydrogen bonds, which are shorter with Brønsted acid sites, resulting in more stable complexes (models Acetanilide/Brønsted and NMB/Brønsted in Scheme 1).
2. From C(sp2)–H to C(sp3)–H: systematic studies on transition metal-catalyzed oxidative C–C formation
Bi-Jie Li and Zhang-Jie Shi*. Chem. Soc. Rev., 2012, 41, 5588–5598
Pd-catalyzed ortho-arylation of acetanilides with organoboronic acids. Having established a facile process for the highly selective C–H halogenation of acetanilide, we sought to develop novel transformations based on its delivered mechanistic information. In the Pd(II)-catalyzed regioselective halogenation of acetanilides, the palladacycle 3 was proposed as a key intermediate, identical to that generated from the oxidative addition of aryl halide to Pd(0) in the traditional cross coupling. This intermediate 3, if formed, could undergo transmetalation with organometallic reagents and reductive elimination to form a C–C bond (Scheme 3). Thus, we hypothesized that a Pd(II)-catalyzed coupling of C–H substrate such as acetanilide with arylboronic acids might proceed under proper conditions to form useful biaryls. This process is essentially unknown at that moment although Pd-catalyzed alkylation of aryl C–H bond with stannane and boron reagents were developed by Yu and co-workers. Earlier at the time, Sanford and co-workers reported a Pd-catalyzed directed arylation of arenes, which likely proceeds through a high-valent palladium intermediate.
3. Ruthenium-catalyzed oxidative ortho-benzoxylation of acetanilides with aromatic acids
Kishor Padala and Masilamani Jeganmohan*. Chem. Commun., 2013, 49, 9651—9653
The scope of ortho-benzoxylation of various substituted acetanilides 1 with 4-chlorobenzoic acid (2a) under the optimized reaction conditions was examined (Table 1). The reaction of 4-methoxy 1b and 4-n-butoxy 1c acetanilides with 2a provided coupling products 3b and 3c in 72% and 75% yields, respectively (entries 1 and 2). Similarly, other electron-donating group substituted acetanilides such as 4-methyl 1d and 4-n-butyl 1e acetanilides yielded the corresponding coupling products 3d and 3e in 66% and 72% yields, respectively (entries 3 and 4). These results clearly revealed that more electron releasing substituents such as O-nBu and n-Bu gave slightly better yields than less electron releasing substituents such as OMe and Me. Halogen group substituted acetanilides were also compatible for the reaction. Thus, the reaction of 4-bromo 1f, -chloro 1g nd 4-fluoro 1h acetanilides with 2a gave the corresponding ortho- enzoxylated acetanilides 3f–h in 74%, 73% and 71% yields, respectively (entries 5–7). The catalytic reaction also worked effectively with electron-withdrawing group substituted acetanilide 1i. he reaction of 4-methyl ester acetanilide (1i)with 2a yielded roduct 3i in 69% yield (entry 8). It is important to note that an ster is also a good directing group for the C–H bond activation eaction. However, in the reaction, the C–H bond activation takes lace only ortho to the NHCOMe of the aromatic moiety. ortho-Methoxy acetanilide 1j was also efficiently involved in the reaction ith 2a, providing coupling product 3j in 67% yield (entry 9).
4. Nanoparticles of ZrPO4 green catalytic applications
Peta Sreenivasulu, Chandrasekhar Pendemb and Nagabhatla Viswanadham*. Nanoscale,2014, 6, 14898–14902
The APNP and ZPNP materials synthesized in the present study have been explored for the fixation of CO2 into aniline molecules for the production of acetanilide. The influence of the temperature, CO2 pressure and reaction time was studied. By varying the reaction temperature from 75 °C to 150 °C, a gradual improvement in conversion of aniline (3.1 to 6.0%) and selectivity of acetanilide (51 to 67%) is observed for the APNP sample (Table 1, entries 1 to 3). The ZPNP sample also exhibited a similar trend of increasing the conversion of aniline (9.2 to 13.0%) and selectivity of acetanilide (69 to 85%) at a constant CO2 pressure of 150 Psi (Table 1, entries 8 to 10). However, further increase in the reaction temperature (175 °C) did not have any accountable effect on the conversion and selectivity values on both the catalysts (Table 1, entries 4 for APNP and 11 for ZPNP). The CO2 pressure also had a significant influence on the conversion of aniline and the selectivity of acetanilide for both samples.