p-Acetotoluidide

Base Information

• Chemical Name: p-Acetotoluidide
• CAS No.: 103-89-9
• Molecular Formula: C9H11NO
• Molecular Weight: 149.192
• Hs Code.: DERIVATION
• European Community (EC) Number: 203-155-4
• NSC Number: 7644
• UNII: N36D4JN82T
• DSSTox Substance ID: DTXSID6024414
• Nikkaji Number: J4.024J
• Wikidata: Q27284480
• ChEMBL ID: CHEMBL1604472
• Mol file: 103-89-9.mol

Synonyms:p-Acetotoluidide(7CI,8CI);1-Acetamido-4-methylbenzene;4-(Acetylamino)toluene;4-Acetamidotoluene;4-Acetotoluide;N-(4-Methylphenyl)acetamide;N-(p-Methylphenyl)acetamide;N-Acetyl-4-methylaniline;N-Acetyl-p-toluidine;N-p-Tolylacetamide;NSC 7644;p-Acetamidotoluene;p-Acetotoluide;p-Acetylaminotoluene;p-Methylacetanilide;

Chemical Property of p-Acetotoluidide

Chemical Property:

• Appearance/Colour: Beige to light brown crystals or cryst. powder
• Melting Point: 149-151 °C(lit.)
• Refractive Index: 1.5279 (estimate)
• Boiling Point: 307.765 °C at 760 mmHg
• PKA: 15.13±0.70(Predicted)
• Flash Point: 177.74 °C
• PSA: 29.10000
• Density: 1.075 g/cm³
• LogP: 2.02640
• Storage Temp.: Store below +30°C.
• Solubility.: 1.2g/l (experimental)
• Water Solubility.: 1 g/L (25 ºC)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 149.084063974
• Heavy Atom Count: 11
• Complexity: 137

Purity/Quality:

99% ^*data from raw suppliers

4''-Methylacetanilide ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)NC(=O)C
• Description: p-Acetotoluidide is an off-white to brown flake, odourless, solid or crystalline powder (pure form), which is soluble in hot water, alcohol, ether, chloroform, acetone, glycerol, and benzene. It is combustible and undergoes self-ignition (at 5450°C) but is otherwise stable under most conditions. p-Acetanilide on decomposition releases carbon monoxide, oxides of nitrogen, carbon dioxide, and toxic fumes. p-Acetanilide is used as an inhibitor of peroxides and stabiliser for cellulose ester varnishes. It is used as an intermediate for the synthesis of rubber accelerators, dyes and dye intermediate, and camphor. It is also used as a precursor in penicillin synthesis and other pharmaceuticals including painkillers and intermediates. Phenylacetamide structure shows analgesic and antipyretic effects. But acetanilide is not used directly for this application due to causing methemoglobinemia (the presence of excessive methemoglobin which does not function reversibly as an oxygen carrier in the blood).
• Uses: 4′-Methylacetanilide was used in the synthesis of stable crystalline phosphorus ylides.

Technology Process of p-Acetotoluidide

There total 208 articles about p-Acetotoluidide 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: 99.0%

acetamide (60-35-5) + para-chlorotoluene (106-43-4) → 4-Methylacetanilide (103-89-9)

Guidance literature:

With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tert-butyl alcohol; at 110 ℃; for 12h;

DOI:10.1021/ja0717414

Reference yield: 96.0%

p-toluidine (106-49-0,12221-03-3) + potassium thioacetate (10387-40-3) → 4-Methylacetanilide (103-89-9)

Guidance literature:

With tetrabutylammonium tetrafluoroborate; In ethyl acetate; at 20 ℃; for 24h; Electrochemical reaction;

DOI:10.1002/cssc.201900814

Reference yield: 94.0%

4-n-methylphenylacetylene (766-97-2) → 4-Methylacetanilide (103-89-9)

Guidance literature:

With sodium azide; C₁₆H₁₇AuBrN₃O; water; trifluoroacetic acid; In 1,2-dichloro-ethane; at 25 ℃; for 2h; regioselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1016/j.jorganchem.2019.02.011

upstream raw materials:

N-acetylacetamide

p-toluidine hydrochloride

N-nitroso-p-methyl-acetanilide

4-methylacetophenone hydrazone

Downstream raw materials:

1--1H-benzotriazole

2H-2-(4-methylphenyl)benzo[d]-1,2,3-triazole 1-oxide

N-(2-benzoyl-4-methylphenyl)acetamide

N-((E)-Octa-2,7-dienyl)-N-p-tolyl-acetamide

Refernces

• 1、 Majumdar, Swapan,Chakraborty, Ankita,Bhattacharjee, Subrata,Debnath, Sudipto,Maiti, Dilip K.. "Silica–ferric chloride (SiO2–FeCl3) catalyzed selective synthesis of 2-substituted benzimidazole through Csp2Csp3bond cleavage of β-ketoester/amide". . p. 4595 - 4598. Retrieved 2016.
• 2、 Rizvi, Syed Umar Farooq,Siddiqui, Hamid Latif,Parvez, Masood,Ahmad, Matloob,Siddiqui, Waseeq Ahmad,Yasinzai, Muhammad Masoom. "Antimicrobial and antileishmanial studies of novel (2E)-3-(2-chloro-6- methyl/methoxyquinolin-3-yl)-1-(aryl)prop-2-en-1-ones". . p. 301 - 306. Retrieved 2010.
• 3、 Rizvi, Syed Umar Farooq,Ahmad, Matloob,Bukhari, Mujahid Hussain,Montero, Catherine,Chatterjee, Payel,Detorio, Mervi,Schinazi, Raymond F.. "Anti-HIV-1 screening of (2E)-3-(2-chloro-6-methyl/methoxyquinolin-3-yl)-1- (aryl)prop-2-en-1-ones". . p. 402 - 407. Retrieved 2014.
• 4、 Govender, Hogantharanni,Mocktar, Chunderika,Koorbanally, Neil A.. "Synthesis and Bioactivity of Quinoline-3-carboxamide Derivatives". . p. 1002 - 1009. Retrieved 2018.
• 5、 de Kiewiet,Stephen. "-". . p. 82. Retrieved 1931.
• 6、 Zaheer, Zahid,Khan, Firoz A. Kalam,Sangshetti, Jaiprakash N.,Patil, Rajendra H.,Lohar. "Novel amalgamation of phthalazine–quinolines as biofilm inhibitors: One-pot synthesis, biological evaluation and in silico ADME prediction with favorable metabolic fate". . p. 1696 - 1703. Retrieved 2016.
• 7、 Sangani, Chetan B.,Makawana, Jigar A.,Duan, Yong-Tao,Yin, Yong,Teraiya, Shashikant B.,Thumar, Nilesh J.,Zhu, Hai-Liang. "Design, synthesis and molecular modeling of biquinoline-pyridine hybrids as a new class of potential EGFR and HER-2 kinase inhibitors". . p. 4472 - 4476. Retrieved 2014.
• 8、 Thungatha, Lamla,Alapour, Saba,Koorbanally, Neil A.. "Synthesis, structural elucidation, intramolecular hydrogen bonding and DFT studies of quinoline-chalcone-chromene hybrids". . p. 74 - 89. Retrieved 2020.
• 9、 Wang, Pan,Yang, Zhenlin,Wang, Ziwei,Xu, Chenyang,Huang, Lei,Wang, Shengchun,Zhang, Heng,Lei, Aiwen. "Electrochemical Arylation of Electron-Deficient Arenes through Reductive Activation". . p. 15747 - 15751. Retrieved 2019.
• 10、 Cheng, Baoxiang,Xu, Jiaxi. "Mechanistic insight into the thermal 1,3-chlorine migrations of N-chloroacetanilides under neutral conditions". . p. 518 - 525. Retrieved 2017.