4-Aminobiphenyl

Base Information

• Chemical Name: 4-Aminobiphenyl
• CAS No.: 92-67-1
• Molecular Formula: C12H11N
• Molecular Weight: 169.226
• Hs Code.: 29214990
• European Community (EC) Number: 202-177-1
• ICSC Number: 0759
• NSC Number: 7660
• UN Number: 3077
• UNII: 16054949HJ
• DSSTox Substance ID: DTXSID5020071
• Nikkaji Number: J3.931D
• Wikipedia: 4-Aminobiphenyl
• Wikidata: Q229922
• NCI Thesaurus Code: C44430
• Metabolomics Workbench ID: 42240
• ChEMBL ID: CHEMBL44201
• Mol file: 92-67-1.mol

Synonyms:4-aminobiphenyl;4-biphenylamine;4-biphenylamine hydrochloride;4-biphenylnitrenium ion

Chemical Property of 4-Aminobiphenyl

Chemical Property:

• Appearance/Colour: brownish yellow solid
• Vapor Pressure: 0.00102mmHg at 25°C
• Melting Point: 52-54 °C(lit.)
• Refractive Index: 1.619
• Boiling Point: 302 °C at 760 mmHg
• PKA: 4.35(at 18℃)
• Flash Point: 152.2 °C
• PSA: 26.02000
• Density: 1.077 g/cm³
• LogP: 3.51700
• Storage Temp.: -20°C Freezer
• Solubility.: Soluble in Dichloromethane, DMSO and Methanol
• Water Solubility.: 842 mg/L at 20–30 °C (quoted, Mercer et al., 1990)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 169.089149355
• Heavy Atom Count: 13
• Complexity: 141
• Transport DOT Label: Class 9

Purity/Quality:

4-Aminobiphenyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xn
• Hazard Codes: T,Xn
• Statements: 45-22-36/37/38-20/21/22
• Safety Statements: 53-45-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Polyaromatic
• Canonical SMILES: C1=CC=C(C=C1)C2=CC=C(C=C2)N
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
• Effects of Long Term Exposure: The substance may have effects on the bladder. This may result in inflammation and tissue lesions. This substance is carcinogenic to humans.
• Description: 4-Aminobiphenyl is an aromatic amine (arylamine) that exists at room temperature as a colorless crystalline solid with a floral odor. It is slightly soluble in cold water, but readily soluble in hot water. It is soluble in ethanol, ether, acetone, chloroform, and lipids. It oxidizes in air and emits toxic fumes when heated to decomposition (Akron 2009).
• Physical properties: Colorless to yellow-brown crystalline solid with a floral-like odor. Becomes purple on exposure to air.
• Uses: Previously used as a rubber antioxidant; no longer produced on a commercial scale In the United States, 4-aminobiphenyl now is used only in laboratory research. It formerly was used commercially as a rubber antioxidant, as a dye intermediate, and in the detection of sulfates (HSDB 2009). In the detection of sulfates. Formerly as rubber antioxidant. As carcinogen in cancer research, induces chromosomal instability in human cancer cells.

Technology Process of 4-Aminobiphenyl

There total 216 articles about 4-Aminobiphenyl 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: 86.0%

tetraphenyltin(IV) (595-90-4) + 4-bromo-aniline (106-40-1) → biphenyl (92-52-4,1594-86-1) + 4-phenylalanine (92-67-1)

Guidance literature:

With dmap; palladium dichloride; for 0.333333h; Microwave irradiation;

DOI:10.3184/174751915X14357494708710

Reference yield: 70.0%

bromobenzene (108-86-1,52753-63-6) + 4-bromo-aniline (106-40-1) → 4-bromodiphenylamine (54446-36-5) + 4-phenylalanine (92-67-1)

Guidance literature:

With tetrabutylammomium bromide; palladium diacetate; potassium carbonate; 2,6-bis(diphenylphosphino)pyridine; In N,N-dimethyl acetamide; at 135 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2014.06.020

Reference yield: 68.0%

4-chloro-aniline (106-47-8) + phenylboronic acid (98-80-6) → biphenyl (92-52-4,1594-86-1) + 4-phenylalanine (92-67-1)

Guidance literature:

With PdCl(2-HO-C₆H₄-CH(Ph)-NH-(CH₂)3-SeC₆H₅); potassium carbonate; In water; N,N-dimethyl-formamide; for 38h; Heating;

DOI:10.1039/c0cc01075h

upstream raw materials:

Diphenyl-4,4'-bis-diazonium

1-phenyl-4-nitrobenzene

2,4'-diaminobiphenyl

4-hydroxylaminobiphenyl

Downstream raw materials:

N-biphenyl-4-yl-maleamic acid

3-methyl-thiophene-2-carboxylic acid biphenyl-4-ylamide

2-([1,1'-biphenyl]-4-yl)isoindoline-1,3-dione

2-(4-aminophenyl)anthracene-9,10-dione

Refernces

Synthesis of new conjugated polymers as hole injection layer and performance of OLED devices

10.1080/15421406.2011.600145

The study focuses on the synthesis of new conjugated polymers based on fluorene and their application as a hole injection layer (HIL) in organic light-emitting diode (OLED) devices. The researchers synthesized a series of crosslinkable conjugated copolymers using a Pd-catalyzed polycondensation reaction, specifically the Buchwald-Hartwig reaction. Key chemicals used in the study include 9,9-dioctyl-2,7-dibromofluorene (DODBF), 4-aminobiphenyl, 2-(4-aminophenyl-styryl)pyridine (2-APSP), sodium-tert-butoxide (NaO-Bu), and tris(dibenzylideneacetone) dipalladium (Pd2(dba)3). These chemicals served to create the backbone and functional groups of the conjugated polymers. Additionally, distyrylpyridyl alkyl monomer (DSM) was used as a crosslinking agent to pattern the polymers, which improved their solvent resistance and facilitated the subsequent spin coating of the emitting layer polymer solution. The purpose of these chemicals was to develop novel polymers that could be used as HIL in OLEDs, enhancing device performance and offering advantages such as improved processability and stability.