4-Hydroxydiphenylamine

Base Information

• Chemical Name: 4-Hydroxydiphenylamine
• CAS No.: 122-37-2
• Deprecated CAS: 2388535-72-4
• Molecular Formula: C12H11NO
• Molecular Weight: 185.225
• Hs Code.: 29222990
• European Community (EC) Number: 204-538-9
• NSC Number: 1543
• UNII: AYK489T98N
• DSSTox Substance ID: DTXSID5037739
• Nikkaji Number: J5.354F
• Wikidata: Q27274191
• Metabolomics Workbench ID: 45638
• ChEMBL ID: CHEMBL1885160
• Mol file: 122-37-2.mol

Synonyms:4-Hydroxydiphenylamine;4-(phenylamino)phenol;122-37-2;4-Anilinophenol;p-Anilinophenol;Phenol, 4-(phenylamino)-;p-Hydroxydiphenylamine;p-Oxydiphenylamine;N-Phenyl-p-aminophenol;Phenyl-p-aminophenol;4-Phenylaminophenol;p-Hydroxydifenylamin;Phenol, p-anilino-;VTI 1;Diphenylamine, 4-hydroxy-;p-(Phenylamino)phenol;para-Hydroxydifenylamin;p-Hydroxydifenylamin [Czech];N-(4-hydroxyphenyl)aniline;NSC 1543;para-Hydroxydifenylamin [Czech];P-ANILINO-PHENOL;EINECS 204-538-9;BRN 0511942;UNII-AYK489T98N;AI3-16911;AYK489T98N;AMINE,DIPHENYL,4-HYDROXY;DTXSID5037739;NSC1543;NSC-1543;MFCD00020142;4-Hydroxy diphenylamine;4-(phenylamino)-phenol;4-Anilinophnol;p-hydroxyldiphenylamine;4-hydrox-phenylaniline;4-hydroxy-diphenylamine;WLN: QR DMR;4-Hydroxy-N-phenylaniline;Fenol, 4-(fenilamino)-;4-hydroxy-N-phenyl-aniline;Oprea1_025350;SCHEMBL92754;4-(Phenylamino)phenol, 9CI;IFLab1_000035;CHEMBL1885160;DTXCID3017739;HYDROXYDIPHENYLAMINE, 4-;HMS1412B13;Tox21_301986;BBL034673;STL417223;AKOS000119655;KG-0220;IDI1_008254;NCGC00164228-01;NCGC00255497-01;AC-11457;CAS-122-37-2;LS-103969;A0470;CS-0130524;FT-0618711;EN300-19905;I10247;A804883;W-108432;Q27274191;Z104476020

Chemical Property of 4-Hydroxydiphenylamine

Chemical Property:

• Appearance/Colour: The common product is reddish brown casting body and the refined products is orange
• Vapor Pressure: 8.52E-05mmHg at 25°C
• Melting Point: 69 - 72 °C
• Refractive Index: 1.67
• Boiling Point: 330.7 °C at 760 mmHg
• PKA: 10.46±0.13(Predicted)
• Flash Point: 146.2 °C
• PSA: 32.26000
• Density: 1.203 g/cm³
• LogP: 3.20880
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 185.084063974
• Heavy Atom Count: 14
• Complexity: 158

Purity/Quality:

99%, ^*data from raw suppliers

4-Hydroxydiphenylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 37/38-41-22-21
• Safety Statements: 26-36/37/39-36/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)NC2=CC=C(C=C2)O
• Uses: 4-Hydroxydiphenylamine is used as a reactant in the preparation of iron methylisopropylglyoxime dimethylpyridine/dimethylaminopyridine/phenylaminophenol/imidazolidone complexes.

Technology Process of 4-Hydroxydiphenylamine

There total 72 articles about 4-Hydroxydiphenylamine 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: 98.0%

1,1'-sulfinylbisbenzene (945-51-7) + 4-amino-phenol (123-30-8) → 4-anilinophenol (122-37-2)

Guidance literature:

With SingaCycle-A₁; sodium t-butanolate; In tetrahydrofuran; at 60 ℃; for 6h; regioselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.8b00060

Reference yield: 92.0%

4-(phenylamino)phenyl acetate (13515-47-4) → 4-anilinophenol (122-37-2)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 4h;

DOI:10.1021/jm0201518

Reference yield: 91.0%

triphenyl phosphite (101-02-0) → 4-anilinophenol (122-37-2)

Guidance literature:

With aniline; hydroquinone; In water;

upstream raw materials:

N,N-diphenylhydroxylamine

N-phenyl-p-benzoquinone imine N-oxide

(4-anilino-phenyl)-amidosulfuric acid

bromobenzene

Downstream raw materials:

1-acetoxy-4-(N-acetyl-anilino)-benzene

N-acetyl-4-hydroxydiphenylamine

N,N'-bis(4-methylphenyl)-1,4-benzenediamine

4-benzyloxy-N-phenylphenylamine

Refernces

• 1、 Bandrowski,E.. "". . p. 475. Retrieved 1888.
• 2、 Varlamov,Krisyuk. "N-H bond dissociation energies in N,N′-diphenyl-1,4-phenylenediamine and its aminyl radical". . p. 1609 - 1614. Retrieved 2004.
• 3、 -. "Substituted anilino-benzothiazole-2-thioketone compound as well as preparation method and application thereof". Paragraph 0071-0072. . Retrieved 2020/06/05.
• 4、 Hu, Huaiyuan,Gilliam, Ashley M.,Qu, Fengrui,Shaughnessy, Kevin H.. "Enolizable Ketones as Activators of Palladium(II) Precatalysts in Amine Arylation Reactions". . p. 4127 - 4135. Retrieved 2020/05/05.