2-Aminobiphenyl

Base Information

• Chemical Name: 2-Aminobiphenyl
• CAS No.: 90-41-5
• Molecular Formula: C12H11N
• Molecular Weight: 169.226
• Hs Code.: Oral rat LD50: 2340 mg/kg
• European Community (EC) Number: 201-990-9
• NSC Number: 7661
• UNII: 8LQM58EBRY
• DSSTox Substance ID: DTXSID3030189
• Nikkaji Number: J3.915B
• Wikipedia: 2-Aminobiphenyl
• Wikidata: Q209308
• ChEMBL ID: CHEMBL296021
• Mol file: 90-41-5.mol

Synonyms:2-aminobiphenyl;2-aminodiphenyl;o-aminobiphenyl;ortho-aminodiphenyl

Chemical Property of 2-Aminobiphenyl

Chemical Property:

• Appearance/Colour: colourless to purple crystalline solid
• Vapor Pressure: 2 mm Hg ( 140 °C)
• Melting Point: 47-50 °C(lit.)
• Refractive Index: 1.613-1.615
• Boiling Point: 299 °C at 760 mmHg
• PKA: 3.82(at 22℃)
• Flash Point: 149.9 °C
• PSA: 26.02000
• Density: 1.077 g/cm³
• LogP: 3.51700
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility.: <0.01 g/100 mL at 21℃
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 169.089149355
• Heavy Atom Count: 13
• Complexity: 149

Purity/Quality:

99% ^*data from raw suppliers

2-Aminobiphenyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-40-52/53-21/22/36/37/38/40-20
• Safety Statements: 36/37-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Polyaromatic
• Canonical SMILES: C1=CC=C(C=C1)C2=CC=CC=C2N
• Description: 2-Aminobiphenyl (2-APB) is an organic compound with the formula C6H5C6H4NH2. It is an amine derivative of biphenyl. It is a colorless solid, although aged samples can appear colored even black. Palladacycles obtained from 2-aminobiphenyl are popular catalysts for cross-coupling.
• Uses: 2-Aminobiphenyl has a mutagenic potency. It is a substrate for UGTs (UDP-glucuronosyltransferases), including UGT1A4, UGT2B13 and UGT2B16.

Technology Process of 2-Aminobiphenyl

There total 174 articles about 2-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: 82.0%

N-chloro-N-methyl-4-toluene sulphonamide (2350-10-9) + C13H13N3 (82084-29-5) → 2-phenylaniline (90-41-5) + 1,2-di([1,1'-biphenyl]-2-yl)diazene (13710-27-5,30926-00-2) + N-methyl-p-toluenesulfonylamide (640-61-9)

Guidance literature:

In benzene; at 40 ℃;

DOI:10.1016/S0040-4039(00)86812-4

Reference yield: 78.0%

2'-phenylbenzenesulphenanilide (103930-04-7) → 2-phenylaniline (90-41-5) + 2-phenyl-N2-(biphenyl-2-yl)-N1-phenylthio-p-benzoquinone di-imine (103930-05-8) + diphenyldisulfane (882-33-7)

Guidance literature:

With trifluoroacetic acid; for 1h; Mechanism; Product distribution; 1.5 equiv. TFA;

Reference yield: 71.0%

2-phenylnitrosobenzene (21711-71-7) + pentacarbonyl(1-methoxybenzylidene)chromium(0) (27436-93-7) → benzoic acid methyl ester (93-58-3,5705-52-2,80226-58-0) + benzo[c]cinnoline (230-17-1) + 9H-carbazole (86-74-8,105184-46-1,97960-57-1) + 2-phenylaniline (90-41-5)

Guidance literature:

In tetrahydrofuran; A soln. of 2-nitrosobiphenyl in THF under N2 is stirred at 25°C until it is light green (5 min), to soln. is added carbene complex in THF, the soln. is then heated under reflux for a period of 5 h.; cooling of resulting olive green soln. to 25°C, solvent removal, residue is dissolved in soln. of 19/1 hexane/ethyl acetate, purifn. by chromy.;

DOI:10.1016/0022-328X(89)80121-4

upstream raw materials:

2-nitrobiphenyl

2-phenylbenzamide

aniline

Phenyl azide

Downstream raw materials:

2-phenanthridin-6-yl-benzoic acid

2-(biphenyl-2-yl)-1H-isoindole-1,3(2H)-dione

2-chloro-benzoic acid biphenyl-2-ylamide

2,8-diphenyl-quinoline-4-carboxylic acid

Refernces

• 1、 Borah, Raju Kumar,Saikia, Hirak Jyoti,Mahanta, Abhijit,Das, Vijay Kumar,Bora, Utpal,Thakur, Ashim Jyoti. "Biosynthesis of poly(ethylene glycol)-supported palladium nanoparticles using Colocasia esculenta leaf extract and their catalytic activity for Suzuki-Miyaura cross-coupling reactions". . p. 72453 - 72457. Retrieved 2015.
• 2、 Ru, Yu,Huang, Yanli,Wang, Yuanyuan,Dai, Liyi. "Pd-Cu alloy nanoparticle supported on amine-terminated ionic liquid functional 3D graphene and its application on Suzuki cross-coupling reaction". . . Retrieved 2019.
• 3、 Leonard, David K.,Ryabchuk, Pavel,Anwar, Muhammad,Dastgir, Sarim,Junge, Kathrin,Beller, Matthias. "A Convenient and Stable Heterogeneous Nickel Catalyst for Hydrodehalogenation of Aryl Halides Using Molecular Hydrogen". . . Retrieved 2022/02/03.
• 4、 -. "Preparation method of 2-aminobiphenyl derivative and 2-hydroxybiphenyl derivative". Paragraph 0024-0027; 0034-0037. . Retrieved 2021/06/12.