3'-Nitroacetanilide

Base Information

• Chemical Name: 3'-Nitroacetanilide
• CAS No.: 122-28-1
• Molecular Formula: C8H8N2O3
• Molecular Weight: 180.163
• Hs Code.: 29242990
• European Community (EC) Number: 204-532-6
• NSC Number: 99339,1314
• UNII: QGH8S22NBP
• DSSTox Substance ID: DTXSID5059539
• Nikkaji Number: J96.165E
• Wikidata: Q27287255
• ChEMBL ID: CHEMBL1568017
• Mol file: 122-28-1.mol

Synonyms:3-nitroacetanilide

Chemical Property of 3'-Nitroacetanilide

Chemical Property:

• Appearance/Colour: Beige crystalline to brown powder
• Vapor Pressure: 6.04E-06mmHg at 25°C
• Melting Point: 154-158 °C(lit.)
• Refractive Index: 1.617
• Boiling Point: 379.004 °C at 760 mmHg
• PKA: 14.20±0.70(Predicted)
• Flash Point: 183.015 °C
• PSA: 74.92000
• Density: 1.341 g/cm³
• LogP: 2.14940
• Storage Temp.: Store below +30°C.
• Solubility.: almost transparency in hot Methanol
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 180.05349212
• Heavy Atom Count: 13
• Complexity: 212

Purity/Quality:

99% ^*data from raw suppliers

m-Nitroacetanilide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1=CC(=CC=C1)[N+](=O)[O-]
• Uses: m-Nitroacetanilide is a useful building block used in a variety of synthetic applications, such as the preparation of chalcones and N-?chloroamines.

Technology Process of 3'-Nitroacetanilide

There total 44 articles about 3'-Nitroacetanilide 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: 94.0%

acetyl chloride (75-36-5) + 3-nitro-aniline (99-09-2) → N-(3-nitrophenyl)acetanilide (122-28-1)

Guidance literature:

bismuth(III) oxychloride; In acetonitrile; at 20 ℃; for 0.0833333h;

DOI:10.1016/j.tetlet.2004.07.044

Reference yield: 94.0%

ethyl acetate (141-78-6) + 3-nitro-aniline (99-09-2) → N-(3-nitrophenyl)acetanilide (122-28-1)

Guidance literature:

With zinc borohydride pyridine complex; In tetrahydrofuran; for 4h; Heating;

Reference yield: 90.0%

acetic acid (64-19-7,77671-22-8) + 3-nitro-aniline (99-09-2) → N-(3-nitrophenyl)acetanilide (122-28-1)

Guidance literature:

With magnesia; In neat (no solvent); at 70 ℃; for 0.5h; chemoselective reaction; Green chemistry;

DOI:10.1016/j.apcata.2013.02.016

upstream raw materials:

N-acetyl-N-phenylacetamide

isocyanic acid (3-nitro-phenyl) ester

acetic anhydride

3-nitrobenzoyl azide

Downstream raw materials:

3-nitro-N-phenylaniline

2,3,4,6-tetranitroaniline

5-(N-acetylamino)-2-bromonitrobenzene

2,5-dinitroacetanilide

Refernces

• 1、 Kumar, Vishal,Dhawan, Sanjeev,Girase, Pankaj Sanjay,Singh, Parvesh,Karpoormath, Rajshekhar. "An Environmentally Benign, Catalyst-Free N?C Bond Cleavage/Formation of Primary, Secondary, and Tertiary Unactivated Amides". . p. 5627 - 5639. Retrieved 2021/11/11.
• 2、 Bayliss, Richard,Boxall, Kathy,Carbain, Benoit,Coxon, Christopher R.,Fry, Andrew M.,Golding, Bernard T.,Griffin, Roger J.,Hardcastle, Ian R.,Harnor, Suzannah J.,Mas-Droux, Corine,Matheson, Christopher J.,Newell, David R.,Richards, Mark W.,Sivaprakasam, Mangaleswaran,Turner, David,Cano, Céline. "2-Arylamino-6-ethynylpurines are cysteine-targeting irreversible inhibitors of Nek2 kinase". supporting information. p. 707 - 731. Retrieved 2020/08/24.