p-((p-Methoxyphenyl)azo)aniline

Base Information

• Chemical Name: p-((p-Methoxyphenyl)azo)aniline
• CAS No.: 2592-28-1
• Molecular Formula: C13H13 N3 O
• Molecular Weight: 227.266
• Hs Code.: 2927000090
• DSSTox Substance ID: DTXSID801038808
• Nikkaji Number: J1.365.716E
• Mol file: 2592-28-1.mol

Synonyms:p-((p-Methoxyphenyl)azo)aniline;2592-28-1;4-[(4-methoxyphenyl)diazenyl]aniline;BRN 0747702;ANILINE, p-((p-METHOXYPHENYL)AZO)-;Benzenamine, 4-[2-(4-methoxyphenyl)diazenyl]-;4-((4-Methoxyphenyl)diazenyl)aniline;3-16-00-00363 (Beilstein Handbook Reference);starbld0048808;monomethoxy-4-aminoazobenzene;4-amino-4'-methoxyazobenzene;4'-Methoxyazobenzene-4-amine;SCHEMBL7067347;SCHEMBL11153232;SCHEMBL14845759;DTXSID801038808;LS-19866

Chemical Property of p-((p-Methoxyphenyl)azo)aniline

Chemical Property:

• Vapor Pressure: 9.75E-07mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 404°Cat760mmHg
• Flash Point: 198.1°C
• PSA: 59.97000
• Density: 1.15g/cm³
• LogP: 4.27400
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 227.105862047
• Heavy Atom Count: 17
• Complexity: 241

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)N=NC2=CC=C(C=C2)N

Technology Process of p-((p-Methoxyphenyl)azo)aniline

There total 9 articles about p-((p-Methoxyphenyl)azo)aniline 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: 60.0%

(E)-1-(4-methoxy-phenyl)-2-(4-nitrophenyl)diazene (20488-62-4) → 4-amino-4'-methoxy-azobenzene (2592-28-1)

Guidance literature:

With hydrazine hydrate; palladium 10% on activated carbon; In methanol; at 40 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jacs.9b06998

Reference yield: 36.9%

4-methoxy-aniline (104-94-9) + aniline (62-53-3) → 4-[(4-methoxyphenyl)azo]aniline (2592-28-1)

Guidance literature:

4-methoxy-aniline; With hydrogenchloride; sodium nitrite; In water; acetonitrile; for 1h; Cooling with ice;

aniline; In methanol; for 1h; Cooling with ice;

Reference yield:

aniline (62-53-3) → 4-[(4-methoxyphenyl)azo]aniline (2592-28-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydrogensulfite / water / 1 h / 65 °C

1.2: 2.25 h / 65 °C

2.1: hydrogenchloride; sodium nitrite

2.3: Reflux

With hydrogenchloride; sodium hydrogensulfite; sodium nitrite; In water;

DOI:10.3109/14756366.2015.1103234

upstream raw materials:

p-methoxybenzenediazonium

anilino-methanesulfonic acid

N-(4-methoxy-phenyl)-N'-phenyl-triazene

aniline hydrochloride

Downstream raw materials:

1,4-Diamino-2-chloro-3-[4-(4-methoxy-phenylazo)-phenylamino]-anthraquinone

1,4-Diamino-2-[4-(4-methoxy-phenylazo)-phenylamino]-anthraquinone

N,N'-bis-[4-(4-methoxy-phenylazo)-phenyl]-thiourea

acetic acid-[4-(4-methoxy-phenylazo)-anilide]

Refernces

• 1、 -. "A novel photochromic azobenzene compound and its synthetic method". Paragraph 0044; 0046; 0047. . Retrieved 2017/08/24.
• 2、 -. "Azo dichroic dye (by machine translation)". Paragraph 0136-0138. . Retrieved 2018/09/02.