3-Amino-4-methylbiphenyl

Base Information

• Chemical Name: 3-Amino-4-methylbiphenyl
• CAS No.: 80938-67-6
• Molecular Formula: C13H13N
• Molecular Weight: 183.253
• Hs Code.: 2921499090
• European Community (EC) Number: 673-684-7
• DSSTox Substance ID: DTXSID7036828
• Nikkaji Number: J36.161E
• Wikidata: Q81984064
• Mol file: 80938-67-6.mol

Synonyms:5-Phenyl-o-toluidine;80938-67-6;3-Amino-4-methylbiphenyl;2-methyl-5-phenylaniline;4-Methyl-[1,1'-biphenyl]-3-amine;4-Methyl-(1,1'-biphenyl)-3-amine;(1,1'-Biphenyl)-3-amine, 4-methyl-;4-methylbiphenyl-3-amine;2-methyl-5-phenyl-aniline;SCHEMBL171357;DTXSID7036828;AMY33045;MFCD00270126;AKOS010254083;s11024;AS-61181;LS-191205;CS-0187031;FT-0682124;EN300-92993;A840008

Chemical Property of 3-Amino-4-methylbiphenyl

Chemical Property:

• Vapor Pressure: 5.47E-05mmHg at 25°C
• Melting Point: 58 °C
• Refractive Index: 1.607
• Boiling Point: 347.2 °C at 760 mmHg
• Flash Point: 177.7 °C
• PSA: 26.02000
• Density: 1.057 g/cm³
• LogP: 3.82540
• Storage Temp.: Sealed in dry,Room Temperature
• Sensitive.: Air Sensitive
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 183.104799419
• Heavy Atom Count: 14
• Complexity: 172

Purity/Quality:

99% ^*data from raw suppliers

5-Phenyl-o-toluidine ^*data from reagent suppliers

Safty Information:

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=C(C=C1)C2=CC=CC=C2)N

Technology Process of 3-Amino-4-methylbiphenyl

There total 6 articles about 3-Amino-4-methylbiphenyl 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: 96.0%

N-(4-methyl-[1,1'-biphenyl]-3-yl)pivalamide (1146127-24-3) → 4-methyl-[1,1'-biphenyl]-3-amine (80938-67-6)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 130 ℃; Solvent; Flow reactor;

DOI:10.1002/anie.201703369

Reference yield: 82.0%

5-bromo-2-methylaniline (39478-78-9) + phenylboronic acid (98-80-6) → 4-methyl-[1,1'-biphenyl]-3-amine (80938-67-6)

Guidance literature:

With potassium carbonate; In water; at 70 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.tet.2016.11.027

Reference yield:

Diphenyliodonium triflate (66003-76-7) → 4-methyl-[1,1'-biphenyl]-3-amine (80938-67-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,2-dichloro-ethane / 70 °C / Inert atmosphere; Flow reactor

2: hydrogenchloride / 1,4-dioxane / 130 °C / Flow reactor

With hydrogenchloride; In 1,4-dioxane; 1,2-dichloro-ethane;

DOI:10.1002/anie.201703369

upstream raw materials:

1-methyl-2-nitro-4-phenylbenzene

4-Methyl-3-nitroanilin

5-bromo-2-methylaniline

phenylboronic acid

Refernces

• 1、 Ma, Xiaojun,Lv, Guanghui,Cheng, Xu,Li, Weijian,Sang, Rui,Zhang, Yong,Wang, Qiantao,Hai, Li,Wu, Yong. "Novel cyclodextrin-modified h-BN@Pd(II) nanomaterial: An efficient and recoverable catalyst for ligand-free C-C cross-coupling reactions in water". . . Retrieved 2017/10/05.
• 2、 Gemoets, Hannes P. L.,Laudadio, Gabriele,Verstraete, Kirsten,Hessel, Volker,No?l, Timothy. "A Modular Flow Design for the meta-Selective C?H Arylation of Anilines". supporting information. p. 7161 - 7165. Retrieved 2017/06/13.