N-(4-Nitrophenyl)acetamide

Base Information

• Chemical Name: N-(4-Nitrophenyl)acetamide
• CAS No.: 104-04-1
• Molecular Formula: C8H8N2O3
• Molecular Weight: 180.163
• Hs Code.: 29242990
• European Community (EC) Number: 203-169-0
• NSC Number: 1315
• UNII: PH3B066365
• DSSTox Substance ID: DTXSID5059290
• Nikkaji Number: J29.440C
• Wikidata: Q7041448
• ChEMBL ID: CHEMBL131469
• Mol file: 104-04-1.mol

Synonyms:4-nitroacetanilide

Chemical Property of N-(4-Nitrophenyl)acetamide

Chemical Property:

• Appearance/Colour: solid
• Melting Point: 213-215 °C(lit.)
• Refractive Index: 1.6180 (estimate)
• Boiling Point: 408.89 °C at 760 mmHg
• PKA: 13.91±0.70(Predicted)
• Flash Point: 201.09 °C
• PSA: 74.92000
• Density: 1.341 g/cm³
• LogP: 2.14940
• Storage Temp.: 2-8°C
• Solubility.: 2.2g/l
• Water Solubility.: 2.2g/L(room temperature)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 180.05349212
• Heavy Atom Count: 13
• Complexity: 204

Purity/Quality:

99% ^*data from raw suppliers

4'-Nitroacetanilide >99.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)NC1=CC=C(C=C1)[N+](=O)[O-]
• Uses: Manufacture of nitraniline. 4-Nitroacetanilide was used as a test substrate and its hydrolysis was determined by UV spectroscopic measurements. It was also used to prepare 4-aminoacetanilide.

Technology Process of N-(4-Nitrophenyl)acetamide

There total 118 articles about N-(4-Nitrophenyl)acetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

Acetanilid (103-84-4) → o-nitroacetanilide (552-32-9) + N-(4-Nitrophenyl)acetamide (104-04-1)

Guidance literature:

With nickel ammonium sulfate; nitric acid; In chloroform; water; at 20 ℃; for 4h;

DOI:10.1081/SCC-100103545

Reference yield: 67.0%

4-nitrophenyl azide (1516-60-5) + dimethylglyoxal (431-03-8) → N-(4-Nitrophenyl)acetamide (104-04-1) + 4-nitro-aniline (100-01-6,104810-17-5)

Guidance literature:

With Me₄NPF₄; In N,N-dimethyl-formamide; Product distribution; Mechanism; electrolytic reduction at a Pt gauze electrode at a potential of -0.30 V; other supporting electrolytes;

DOI:10.1021/jo00301a018

Reference yield: 46.0%

2-acetyl-3-(4-nitrophenyl)isoxazol-5(2H)-one (267877-41-8) → 2-methyl-4-(4-nitro-phenyl)-oxazole (79965-75-6) + N-(4-Nitrophenyl)acetamide (104-04-1) + 4-Nitrophenylacetonitrile (555-21-5,34512-13-5,174848-08-9) + 4-nitrobenzonitrile (619-72-7)

Guidance literature:

at 500 ℃; Further Variations:; Temperatures; Product distribution;

DOI:10.1071/CH99075

upstream raw materials:

thioacetic acid

4-nitrobenzenediazonium chloride

N-acetyl-N-phenylacetamide

N-<4-(trimethylsilyl)phenyl>acetamide

Downstream raw materials:

para-dinitrobenzene

2-nitro-N-(4-nitrophenyl)benzenamine

N-nitrosamide of N-(4-nitrophenyl)acetamide

N-ethyl-N-(4-nitrophenyl)acetamide

Refernces

• 1、 Chainikova, Ekaterina,Khursan, Sergey,Yusupova, Alfia,Lobov, Alexander,Abdullin, Marat,Safiullin, Rustam. "On the mechanism for the photooxidation of aromatic azides containing a secondary N–H bond: A sequence of intramolecular transformations with the formation of heterocyclic oximes". . p. 3267 - 3271. Retrieved 2018.
• 2、 Kim, Jin Hyung,Kim, Yong Hae. "NOVEL DESULFURIZATION OF THIOCARBONYL COMPOUNDS INTO THEIR CARBONYL COMPOUNDS WITH TERTIARY BUTYL THIONITRATE". . p. 1669 - 1670. Retrieved 1987.
• 3、 Rabiger,Joullie. "-". . p. 1649. Retrieved 1961.
• 4、 Nasr-Esfahani, Masoud,Montazerozohori, Morteza,Moghadam, Majid,Mohammadpoor-Baltork, Iraj,Moradi, Sareh. "Transformation of thioamide compounds to corresponding amides using 12-Tungstosilicic acid". . p. 261 - 266. Retrieved 2010.
• 5、 Nasr-Esfahani, Masoud,Moghadam, Majid,Mohammadpoor-Baltork, Iraj,Boostanifar, Mohammad Hasan. "A mild and convenient method for conversion of thioamides to their corresponding amides using acidified wet silica-supported permanganate under solvent-free conditions". . p. 141 - 146. Retrieved 2009.
• 6、 Kanta De, Surya. "Ruthenium(III) chloride catalyzed acylation of alcohols, phenols, thiols, and amines". . p. 2919 - 2922. Retrieved 2004.
• 7、 Suzuki, Hitomi,Ishibashi, Taro,Murashima, Takashi,Tsukamoto, Kenkichi. "Ortho-Selective Nitration of Acetanilides with Nitrogen Dioxide in the Presence of Ozone". . p. 6591 - 6594. Retrieved 1991.
• 8、 Behera, Satyaranjan,Patra, Braja N.. "An efficient, economical and eco-friendly acylation of alcohols and amines by alum doped nanopolyaniline under solvent free condition". . . Retrieved 2021/08/06.