Acetanilide

Base Information

• Chemical Name: Acetanilide
• CAS No.: 103-84-4
• Molecular Formula: C8H9NO
• Molecular Weight: 135.166
• Hs Code.: 29242995
• European Community (EC) Number: 203-150-7,695-031-5,693-255-8
• NSC Number: 757879,7636
• UNII: SP86R356CC
• DSSTox Substance ID: DTXSID2022543
• Nikkaji Number: J4.023A
• Wikipedia: Acetanilide
• Wikidata: Q421761
• NCI Thesaurus Code: C76696
• RXCUI: 162
• Pharos Ligand ID: HPLJCG7X21YV
• Metabolomics Workbench ID: 37682
• ChEMBL ID: CHEMBL269644
• Mol file: 103-84-4.mol

Synonyms:acetanilid;acetanilide

Chemical Property of Acetanilide

Chemical Property:

• Appearance/Colour: odourless solid chemical of leaf or flake-like appearance
• Vapor Pressure: 1 mm Hg ( 114 °C)
• Melting Point: 113-115 °C(lit.)
• Refractive Index: 1.552
• Boiling Point: 304.5 °C at 760 mmHg
• PKA: 0.5(at 25℃)
• Flash Point: 173.9 °C
• PSA: 29.10000
• Density: 1.103 g/cm³
• LogP: 1.71800
• Storage Temp.: Store below +30°C.
• Solubility.: 5g/l
• Water Solubility.: 5 g/L (25 ºC)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 135.068413911
• Heavy Atom Count: 10
• Complexity: 116

Purity/Quality:

99% ^*data from raw suppliers

Acetanilide(Acetylaniline) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 22-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: CC(=O)NC1=CC=CC=C1
• Physical properties: White glossy flake crystal or white crystalline powder. Slightly soluble in cold water, soluble in hot water, methanol, ethanol, ether, chloroform, acetone, glycerol and benzene.
• Uses: Acetanilide is used as an intermediate in the synthesis of rubber accelerator, dyes and camphor. It is also used in the synthesis of penicillin and other pharmaceutical products. It is involved in the preparation of 4-acetamidobenzenesulfonyl chloride, which is an intermediate during the synthesis of sulfa drugs. Further, it is employed as a experimental photographic developer. In addition to this, it is used to stabilize cellulose ester varnishes.

Technology Process of Acetanilide

There total 968 articles about Acetanilide 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: 90.0%

peracetic acid (79-21-0) + aniline (62-53-3) → Acetanilid (103-84-4) + azoxybenzene (495-48-7,55599-32-1)

Guidance literature:

In acetonitrile; at 50 ℃; for 0.333333h;

DOI:10.1021/acs.joc.5b00582

Reference yield: 80.0%

Diphenylmethane (101-81-5) + acetyl chloride (75-36-5) → benzonitrile (100-47-0) + Acetanilid (103-84-4)

Guidance literature:

Diphenylmethane; With sodium azide; oxygen; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; at 40 ℃; for 4h; Sealed tube;

acetyl chloride;

DOI:10.1038/s41557-018-0156-y

Reference yield: 57.91%

1,1'-Diacetyl-1,1',4,4'-tetrahydro-4,4'-bipyridine (3451-88-5) + Nitrosobenzene (586-96-9) → N,O-diacetylphenylhydroxylamine (32954-65-7) + N-Phenylacetohydroxamic acid (1795-83-1) + 2-Hydroxyazoxybenzene (91100-74-2) + Acetanilid (103-84-4) + Azobenzene (1227476-15-4) + azoxybenzene (495-48-7,55599-32-1)

Guidance literature:

In chloroform; for 18h; Mechanism; Ambient temperature;

upstream raw materials:

diazomethane

methanol

diethyl ether

N-acetyl-N-phenylacetamide

Downstream raw materials:

4-bromoacetanilide

p-aminobenzophenone

N-acetylsulfanilic acid

N-acetyl-N-phenylacetamide

Refernces

• 1、 Buslov, Ivan,Hu, Xile. "Transition metal-free intermolecular a-C-H amination of ethers at room temperature". . p. 3325 - 3330. Retrieved 2014.
• 2、 Bokosi, Fostino R. B.,Beteck, Richard M.,Laming, Dustin,Hoppe, Heinrich C.,Tshiwawa, Tendamudzimu,Khanye, Setshaba D.. "Synthesis of 2-(N-cyclicamino)quinoline combined with methyl (E)-3-(2/3/4-aminophenyl)acrylates as potential antiparasitic agents". . . Retrieved 2021.
• 3、 Basu, Jayanta Kumar,Maji, Nitai Chandra,Sengupta, Sonali,Supriya. "Synthesis of multilayer polymer-immobilised nanosilver for catalytic study in condensation reaction of aniline and acetylacetone". . . Retrieved 2020.
• 4、 Tschamber, Theophile,Streith, Jacques. "METHYLKETENE, A MINOR BUT HIGHLY REACTIVE BYPRODUCT IN THE PYROLYSIS GAS OF ACETONE". . p. 4503 - 4506. Retrieved 1980.
• 5、 Matsugi, Masato,Suganuma, Misaki,Yoshida, Shoko,Hasebe, Shohei,Kunda, Yoko,Hagihara, Kotaro,Oka, Sayaka. "An alternative and facile purification procedure of amidation and esterification reactions using a medium fluorous Mukaiyama reagent". . p. 6573 - 6574. Retrieved 2008.
• 6、 Seddighi, Mohadeseh,Shirini, Farhad,Goli-Jolodar, Omid. "Preparation, characterization and application of RHA/TiO2 nanocomposites in the acetylation of alcohols, phenols and amines". . p. 1003 - 1010. Retrieved 2016.
• 7、 Mojtahedi, Mohammad M.,Saeed Abaee,Heravi, Majid M.,Behbahani, Farahnaz K.. "Additive-free chemoselective acylation of amines and thiols". . p. 95 - 99. Retrieved 2007.
• 8、 Mahajan, Sheena,Slathia, Nancy,Kapoor, Kamal K.. "Beckmann rearrangement: Thiamine hydrochloride as a remarkable catalyst for one-pot synthesis of amides from ketones". . . Retrieved 2020.
• 9、 Tamhankar,Desai,Mane,Wadgaonkar,Bedekar. "A simple and practical halogenation of activated arenes using potassium halide and oxone in water-acetonitrile medium". . p. 2021 - 2027. Retrieved 2001.
• 10、 Duan, Pan,Guo, Yu,Kang, Huan,Li, Yi-Na,Wen, Xianghao,Xiao, Fang,Zeng, Yao-Fu,Zhang, Na-Na. "Synthesis of acetamides from aryl amines and acetonitrile by diazotization under metal-free conditions". . p. 2169 - 2172. Retrieved 2019.