40655-37-6

Basic information

• Product Name: N-[4-(1,1-dimethylethyl)-2-nitrophenyl]acetamide
• Synonyms: N-[4-(1,1-dimethylethyl)-2-nitrophenyl]acetamide;N-(2-Nitro-4-tert-butylphenyl)acetamide
• CAS NO: 40655-37-6
• Molecular Formula: C₁₂H₁₆N₂O₃
• Molecular Weight: 236.26704
• EINECS: 255-023-0
• Mol File: 40655-37-6.mol

Chemical Properties

• Boiling Point: 385.2 °C at 760 mmHg
• Flash Point: 186.8 °C
• Appearance: /
• Density: 1.175 g/cm³
• Vapor Pressure: 3.87E-06mmHg at 25°C
• Refractive Index: 1.564
• CAS DataBase Reference: N-[4-(1,1-dimethylethyl)-2-nitrophenyl]acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[4-(1,1-dimethylethyl)-2-nitrophenyl]acetamide(40655-37-6)
• EPA Substance Registry System: N-[4-(1,1-dimethylethyl)-2-nitrophenyl]acetamide(40655-37-6)

Safety Data

• Hazardous Substances Data: 40655-37-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
N-[4-(1,1-dimethylethyl)-2-nitrophenyl]acetamide is used as a research tool for investigating the role of PDE9 in neurological disorders. Its application is centered around understanding the potential therapeutic benefits of PDE9 inhibition in conditions like Alzheimer's disease.
Used in Cognitive Enhancement Studies:
In the field of cognitive enhancement, N-[4-(1,1-dimethylethyl)-2-nitrophenyl]acetamide is used as a compound to explore the effects of increased cGMP levels on cognitive functions. The research in this area aims to assess whether the compound can improve memory and cognitive abilities in individuals suffering from cognitive decline.

InChI:InChI=1/C12H16N2O3/c1-8(15)13-10-6-5-9(12(2,3)4)7-11(10)14(16)17/h5-7H,1-4H3,(H,13,15)

Upstream product

• 20330-45-4 4-tert-butylacetanilide 
• 3282-56-2 4-tert-butylnitrobenzene 
• 769-92-6 4-tert-Butylaniline 
• 108-24-7 acetic anhydride 
• 103-84-4 Acetanilid 
• 253185-03-4 tert-butylbenzene 

Downstream Products

• 22503-15-7 N-(4-(tert-butyl)-2,6-dinitrophenyl)acetamide 
• 342045-14-1 2-amino-4-tert-butylacetanilide 
• 6310-19-6 4-tert-butyl-2-nitroaniline 
• 110969-41-0 Acetyl-(4-tert-butyl-2-nitro-phenyl)-carbamic acid tert-butyl ester 
• 85020-95-7 4-t-butyl-N-methyl-2-nitroacetanilide 
• 68176-57-8 4-(tert-butyl)-1,2-diaminobenzene 
• 110969-46-5 (4-tert-Butyl-2-nitro-phenyl)-carbamic acid tert-butyl ester 
• 85020-93-5 4-(tert-butyl)-N-methyl-2-nitroaniline 
• 22503-16-8 4-tert-butyl-2,6-dinitro-aniline 
• 5805-62-9 2-Methyl-5(6)-tert.-butylbenzimidazol 
• 23132-52-7 1-tert-butyl-3-nitrobenzene 
• 159724-47-7 N-(3-bromophenyl)-4-tert-butyl-2-nitroaniline 
• 1287739-91-6 5'-(4-tert-butyl-2-nitrophenylamino)-2',6-difluorobiphenyl-2-carbonitrile 
• 1287738-95-7 5'-(5-tert-butyl-1H-benzo[d]imidazol-1-yl)-2',6-difluorobiphenyl-2-carbonitrile 

Relevant articles and documents

Transition-metal-free mono- or dinitration of protected anilines

An amide-assisted arene nitration is presented, and both mono- and dinitration of protected anilines could be effected by using NaNO2 and NaNO3 as the mono- and bisnitrating agents, respectively. This divergent synthesis is transition-metal- and acid-free, and features a broad substrate scope, low cost, and ortho–para selectivity.

Regioselective nitration of anilines with Fe(NO3)3·9H2O as a promoter and a nitro source

An efficient Fe(NO3)3·9H2O promoted ortho-nitration reaction of aniline derivatives has been developed. This reaction may go through a nitrogen dioxide radical (NO2) intermediate, which is generated by the thermal decomposition of iron(iii) nitrate. The practicality of the present method using nontoxic and inexpensive iron reagents has been shown by the broad substrate scope and applications.

BENZIIMIDAZOLE AND IMIDAZOPYRIDINE DERIVATIVES AS SODIUM CHANNEL MODULATORS

The invention relates to benzimidazole and imidazopyridine derivatives, to their use in medicine, to compositions containing them, to processes for their preparation and to intermediates used in such processes. More particularly the invention relates to new Nav1.8 modulators of formula (I) or pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, R5, R6, R7. X and Y are as defined in the description. Nav1.8 modulators are potentially useful in the treatment of a wide range of disorders, particularly pain.

Molecular spur gears comprising triptycene rotators and bibenzimidazole-based stators

Dynamic gearing of molecular spur gears, the most common type of mechanical gear, is elucidated. Molecular design and conformational analysis show that derivatives of 4,4-bis(triptycen-9-ylethynyl)bibenzimidazole represent suitable constructs to investigate gearing behavior of collateral triptycene (Tp) groups. To test this design, DFT calculations (B97-D/Def2-TZVP) were employed and the results suggest that these molecules undergo geared rotation preferentially to gear slippage. Synthesis of derivatives was carried out, providing a series of molecular spur gears, including the first desymmetrized spur gear molecules, which were subsequently subjected to stereochemical analysis.

SUBSITITUTED BENZIMIDAZOLES

This invention relates to novel substituted benzimidazoles and pharmaceutically acceptable salts thereof. This invention also provides compositions comprising a compound of this invention and the use of such compositions in methods of treating diseases and conditions that are beneficially treated by administering a compound that modulates theGABAA receptor. This invention also provides novel intermediates for the preparation of the compounds of the invention, and salts thereof.

Synthesis and property studies of cyclotrisazobenzenes

Azobenzenophanes are fascinating macrocycles, which are of special interest due to their unique photochromic behavior. Cyclotrisazobenzenes 2 (R = H, Br, tBu) were prepared to probe how much strain the photoisomerization of the azobenzene motive can tolerate. The macrocycles were synthesized in an overall yield of 10-20% from oriho-phenylenediamine (6). Solid-state structures of cyclotrisazobenzenes 2a and 2b were obtained. Irradiation under various conditions did not induce any isomerization.

Structure-activity relationship of omeprazole and analogues as Helicobacter pylori urease inhibitors

Helicobacter pylori urease belongs to a family of highly conserved urea- hydrolyzing enzymes. A common feature of these enzymes is the presence of two Lewis acid nickel ions and a reactive cysteine residue in the active site. The H+/K+-ATPase inhibitor omeprazole is a prodrug of a sulfenamide which covalently modifies cysteine residues on the luminal side of the H+/K+- ATPase of gastric parietal cells. Omeprazole and eight analogues were selected based on their chemical, electronic, and kinetic properties, and each was incubated with viable H. pylori in phosphate-buffered saline at pH 7.4 for 30 min, after which 100 mM urea was added and the amount of ammonia formed analyzed after a further 10 min. Inhibition between 0% and 100% at a 0.1 mM concentration was observed for the different analogues and could be expressed as a function of the pK(a)-value of the pyridine, the pK(a)-value of the benzimidazole, the overall lipophilicity, and, most importantly, the rate of sulfenamide formation, in a quantitative structure-activity relationship. The inhibition was potentiated by a lower pH (favoring the formation of the sulfenamide) but abolished in the presence of β- mercaptoethanol (a scavenger of the sulfenamide). Structural analogues incapable of yielding the sulfenamide did not inhibit ammonia production. Treatment of Helicobacter felis-infected mice with 230 μmol/kg flurofamide b.i.d. for 4 weeks, known to potently inhibit urease activity in vivo, as a means of eradicating the infection, was tested and compared with the effect of 125 μmol/kg omeprazole b.i.d. for 4 weeks. Neither treatment proved efficacious.

Intramolecular Hydrogen Bonding in Some ortho-Substituted N-Methyl-, N-Benzyl- and N-Aryl-4-nitroanilines: a Proton Magnetic Resonance Study

1H n.m.r. spectra of a wide variety of N-methyl, N-benzyl and N-aryl 2-substituted 4-nitroanilines where the 2-substituent is an electron-withdrawing group, namely acetyl, cyano, formyl or methoxycarbonyl, reveal that long-range coupling (5J 0.65-0.70 Hz) occurs between the NH proton and the 5-proton of the nitroaryl ring in (D)chloroform solution; coupling is absent when the 2-substituent is trifluoromethyl.However, for some compounds (the nature of the 2-substituent is critical), NH,H5 coupling is absent in (D6)dimethyl sulfoxide solution.An examination of these phenomena leads to the conclusion (a) that intramolecular hydrogen bonding occurs between the NH group and the 2-substituent and (b) that, for these N,2-substituted 4-nitroanilines, the intramolecular hydrogen bond strength decreases in the following order: NH...COOCH3 > NH...NO2 ca.NH...COCH3 > NH...CHO > NH...CN A parallel study involving some N-methyl 4-substituted 2-nitroanilines where the 4-substituent is an electron-donating group, namely t-butyl, methyl and methoxy, revealed long-range NH,H5 coupling in both (D)chloroform and (D6)dimethyl sulfoxide solution; when the substituent is dimethylamino, NH,H5 coupling could not be detected in either solvent.