p-Phenetidine

Base Information

• Chemical Name: p-Phenetidine
• CAS No.: 156-43-4
• Molecular Formula: C8H11NO
• Molecular Weight: 137.181
• Hs Code.: 29222200
• European Community (EC) Number: 205-855-5
• ICSC Number: 1720
• NSC Number: 3116
• UN Number: 2311
• UNII: 9TSL224ZSE
• DSSTox Substance ID: DTXSID0025864
• Nikkaji Number: J2.032J
• Wikipedia: P-Phenetidine
• Wikidata: Q27158608
• ChEMBL ID: CHEMBL250969
• Mol file: 156-43-4.mol

Synonyms:Aminophenetole;Ethoxyaniline;Phenetidine

Chemical Property of p-Phenetidine

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 0.0177mmHg at 25°C
• Melting Point: 2-5 °C(lit.)
• Refractive Index: n20/D 1.559(lit.)
• Boiling Point: 254 °C at 760 mmHg
• PKA: 5.2(at 28℃)
• Flash Point: 110.3 °C
• PSA: 35.25000
• Density: 1.037 g/cm³
• LogP: 2.24870
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: 20g/l
• Water Solubility.: practically insoluble
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 137.084063974
• Heavy Atom Count: 10
• Complexity: 87.3
• Transport DOT Label: Poison

Purity/Quality:

99.5% ^*data from raw suppliers

p-Phenetidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi,Xn
• Hazard Codes: T,Xi,Xn
• Statements: 23/24/25-33-68-43-36-20/21/22
• Safety Statements: 28-36/37-45-46

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: CCOC1=CC=C(C=C1)N
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes.
• Effects of Long Term Exposure: The substance may have effects on the blood. This may result in the formation of methaemoglobin.
• Uses: A toxic metabolite of Phenacetin (P294580) which exhibits high renal toxicity. p-Phenetidine also reduced COX-1 and COX-2 expression in neutrophils.

Technology Process of p-Phenetidine

There total 120 articles about p-Phenetidine 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: 45.6%

methoxybenzene (100-66-3) → 2-methoxy-phenylamine (90-04-0) + 4-Ethoxyaniline (156-43-4)

Guidance literature:

With O-(4-nitrobenzoyl)hydroxylammonium trifluoromethanesulfonate; iron(II) bromide; silver(I) triflimide; In 2,2,2-trifluoroethanol; water; at 30 ℃; for 2h; Reagent/catalyst; Solvent;

DOI:10.1002/chem.201605476

Reference yield: 41.0%

1-methyl-6-(4'-ethoxyphenyl)-2,5-dithiobiurea (125908-30-7) → 2-(4'-ethoxyphenylamino)-Δ2-1,3,4-thiadiazoline-5-thione (68161-60-4) + 4-Ethoxyaniline (156-43-4) + methylamine (74-89-5) + 4-methyl-[1,2,4]triazolidine-3,5-dithione (13625-51-9)

Guidance literature:

With sodium hydroxide; In water; Heating;

Reference yield: 41.0%

1-ethyl-6-(4'-ethoxyphenyl)-2,5-dithiobiurea (125908-34-1) → 2-(4'-ethoxyphenylamino)-Δ2-1,3,4-thiadiazoline-5-thione (68161-60-4) + ethylamine (75-04-7,85404-22-4) + 4-Ethoxyaniline (156-43-4) + 4-ethyl-[1,2,4]triazolidine-3,5-dithione (13625-52-0)

Guidance literature:

With sodium hydroxide; In water; Heating;

upstream raw materials:

ethyl bromide

4-benzylidenamino-phenol

1-chloro-4-ethoxybenzene

(4-ethoxy-phenyl)-amidosulfuric acid

Downstream raw materials:

6-ethoxy-2-pyridin-4-yl-benzothiazole

thioisonicotinic acid p-phenetidide

4-ethoxy-N-pyridin-2-ylmethylene-aniline

N-furfurylidene-p-phenetidine

Refernces

• 1、 Nohmi,Ishidate Jr.,Hiratsuka,Watabe. "Mechanism of metabolic activation of the analgetic bucetin to bacterial mutagens by hamster liver microsomes". . p. 2877 - 2885. Retrieved 1985.
• 2、 Popov,Mokhov. "Colloid and nanosized catalysts in organic synthesis: V. Reactions of alkyl halides and alcohols with ?2-diketones in the presence of metal nanoparticles". . p. 1491 - 1495. Retrieved 2014.
• 3、 Hosseiny, Malihesadat,Khosroyar, Susan,Kiani, Zahra,Motavalizadehkakhky, Alireza,Zhiani, Rahele. "Selective reduction of nitro-compounds to primary amines by tetrapyridinoporphyrazinato zinc (II) supported on DFNS". . . Retrieved 2021/06/14.
• 4、 -. "Green synthesis method of p-aminophenetole". Paragraph 0005; 0008-0010. . Retrieved 2020/02/10.