3-Chlorodiphenylamine

Base Information

• Chemical Name: 3-Chlorodiphenylamine
• CAS No.: 101-17-7
• Molecular Formula: C12H10ClN
• Molecular Weight: 203.671
• Hs Code.: 2921440000
• European Community (EC) Number: 202-922-0
• UNII: NPC5U6JP9A
• DSSTox Substance ID: DTXSID70143615
• Nikkaji Number: J37.747C
• Wikidata: Q83007577
• Mol file: 101-17-7.mol

Synonyms:3-Chlorodiphenylamine;101-17-7;3-chloro-n-phenylaniline;Benzenamine, 3-chloro-N-phenyl-;3-Chloro-N-phenyl-benzenamine;N-(3-Chlorophenyl)aniline;N-phenyl-3-chloroaniline;3-Cl-DPA;NPC5U6JP9A;EINECS 202-922-0;3-Chloro-N-phenylaniline;m-Chlorodiphenylamine;N-(3-Chlorophenyl)-N-phenylamine;3-chlordiphenylamin;N-phenyl-3-chloraniline;UNII-NPC5U6JP9A;3 Cl-DPA;Diphenylamine, 3-chloro-;3-chloro-N-phenyl-aniline;3-Chloro-N-phenylbenzenamine;Oprea1_486499;Oprea1_488154;SCHEMBL3951892;OHHIBZKYXJDQEU-UHFFFAOYSA-;DTXSID70143615;MFCD00000590;N-(3-Chlorophenyl)-N-phenylamine #;AKOS015915503;SB78319;AS-16099;HY-131948;CS-0144538;FT-0615484;C77692;A800345;W-108923

Chemical Property of 3-Chlorodiphenylamine

Chemical Property:

• Vapor Pressure: 0.000102mmHg at 25°C
• Melting Point: 112 °C(Solv: methanol (67-56-1))
• Refractive Index: 1.642
• Boiling Point: 337.822 °C at 760 mmHg
• PKA: -0.20±0.30(Predicted)
• Flash Point: 147.422 °C
• PSA: 12.03000
• Density: 1.216 g/cm³
• LogP: 4.15660
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 203.0501770
• Heavy Atom Count: 14
• Complexity: 166

Purity/Quality:

99% ^*data from raw suppliers

3-Chlorodiphenylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
• Hazard Codes: R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
• Statements: 20/21/22
• Safety Statements: 28-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)NC2=CC(=CC=C2)Cl
• Uses: 3-Chlorodiphenylamine (cas# 101-17-7) is a compound useful in organic synthesis.

Technology Process of 3-Chlorodiphenylamine

There total 23 articles about 3-Chlorodiphenylamine 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: 100.0%

bromobenzene (108-86-1,52753-63-6) + 3-chloro-aniline (108-42-9) → 3-chlorodiphenylamine (101-17-7)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 90 - 110 ℃; for 11h;

DOI:10.1021/ol053162e

Reference yield: 96.0%

3-iodochlorobenzene (625-99-0) + 3-trifluoromethylaniline (98-16-8) → 3-chlorodiphenylamine (101-17-7)

Guidance literature:

With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl]palladium(ll); sodium t-butanolate; In toluene; at 80 ℃; Inert atmosphere;

Reference yield: 95.0%

3-chlorophenyl fluorosulfonate (1535-32-6) + aniline (62-53-3) → 3-chlorodiphenylamine (101-17-7)

Guidance literature:

With η⁵‐cyclopentadienyl‐η³‐1‐phenylallylpalladium; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 80 ℃; for 12h; Reagent/catalyst; Temperature; Solvent;

DOI:10.1021/acscatal.6b00865

upstream raw materials:

bromobenzene

3-Chloroacetanilide

N-(3-chlorophenyl)anthranilic acid

N-(3-chloro-phenyl)-N-phenyl-benzamide

Downstream raw materials:

N-(3-chloro-phenyl)-N-phenyl-β-alanine nitrile

(3-chloro-phenyl)-[2-(1-methyl-[2]piperidyl)-ethyl]-phenyl-amine

N,N-diphenyl-m-toluidine

1-(m-chlorophenyl)-1-phenylurea

Refernces

• 1、 Yoo, Woo-Jin,Tsukamoto, Tatsuhiro,Kobayashi, Shu. "Visible-Light-Mediated Chan-Lam Coupling Reactions of Aryl Boronic Acids and Aniline Derivatives". . p. 6587 - 6590. Retrieved 2015.
• 2、 Gong, Shuwen,Gu, Yuxiao,Huang, Xianqiang,Li, Jikun,Li, Qiang,Qi, Yuquan,Shen, Guodong. "Imidazole-directed fabrication of three polyoxovanadate-based copper frameworks as efficient catalysts for constructing C-N bonds". . p. 10970 - 10976. Retrieved 2020.
• 3、 Wexler, Ryan P.,Nuhant, Philippe,Senter, Timothy J.,Gale-Day, Zachary J.. "Electrochemically Enabled Chan-Lam Couplings of Aryl Boronic Acids and Anilines". . p. 4540 - 4543. Retrieved 2019.
• 4、 Lee,Jung,Hahn. "N-arylation of amines with o-silylaryl triflate". . p. 6690 - 6692. Retrieved 2013.
• 5、 Manna, Kartic,Ganguly, Tanusree,Baitalik, Sujoy,Jana, Ranjan. "Visible-Light- And PPh3-Mediated Direct C-N Coupling of Nitroarenes and Boronic Acids at Ambient Temperature". supporting information. p. 8634 - 8639. Retrieved 2021/11/01.
• 6、 Akatyev, Nikolay,Il'in, Mikhail,Il'in, Mikhail,Peregudova, Svetlana,Peregudov, Alexander,Buyanovskaya, Anastasiya,Kudryavtsev, Kirill,Dubovik, Alexander,Grinberg, Valerij,Orlov, Victor,Pavlov, Alexander,Novikov, Valentin,Volkov, Ilya,Belokon, Yuri. "Chan-Evans-Lam C?N Coupling Promoted by a Dinuclear Positively Charged Cu(II) Complex. Catalytic Performance and Some Evidence for the Mechanism of CEL Reaction Obviating Cu(III)/Cu(I) Catalytic Cycle". . p. 3010 - 3021. Retrieved 2020/04/29.