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101-17-7

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101-17-7 Usage

Chemical Properties

Pale Yellow Oil

Uses

3-Chlorodiphenylamine (cas# 101-17-7) is a compound useful in organic synthesis.

Check Digit Verification of cas no

The CAS Registry Mumber 101-17-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 1 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 101-17:
(5*1)+(4*0)+(3*1)+(2*1)+(1*7)=17
17 % 10 = 7
So 101-17-7 is a valid CAS Registry Number.
InChI:InChI=1/C12H10ClN/c13-10-5-4-8-12(9-10)14-11-6-2-1-3-7-11/h1-9,14H

101-17-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-chloro-N-phenylaniline

1.2 Other means of identification

Product number -
Other names N-(3-Chlorophenyl)aniline

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:101-17-7 SDS

101-17-7Synthetic route

bromobenzene
108-86-1

bromobenzene

3-chloro-aniline
108-42-9

3-chloro-aniline

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium (0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 90 - 110℃; for 11h; Buchwald-Hartwig reaction;100%
With pectin-stabilized copper nanoparticles In dimethyl sulfoxide at 110℃; for 2h;82%
3-iodochlorobenzene
625-99-0

3-iodochlorobenzene

3-trifluoromethylaniline
98-16-8

3-trifluoromethylaniline

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

Conditions
ConditionsYield
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;96%
2-iodocyclohex-2-en-1-one
33948-36-6

2-iodocyclohex-2-en-1-one

3-chloro-aniline
108-42-9

3-chloro-aniline

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol at 75℃; for 1h; Inert atmosphere;95%
With toluene-4-sulfonic acid In ethanol at 75℃;40%
3-chlorophenyl fluorosulfonate
1535-32-6

3-chlorophenyl fluorosulfonate

aniline
62-53-3

aniline

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

Conditions
ConditionsYield
With η5‐cyclopentadienyl‐η3‐1‐phenylallylpalladium; potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 80℃; for 12h; Reagent/catalyst; Temperature; Solvent;95%
3-chloro-aniline
108-42-9

3-chloro-aniline

phenylboronic acid
98-80-6

phenylboronic acid

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

Conditions
ConditionsYield
With copper immobilized at polyimide covalent organic framework In methanol; water at 20℃; for 8h; Chan-Lam Coupling;87%
With pyridine; copper(II) acetate monohydrate In dichloromethane at 39.84℃; for 24h;83%
With potassium tert-butylate; tetra(n-butyl)ammonium hydroxide; copper diacetate In water at 20℃; for 22h;72%
3-chlorophenylboronic acid
63503-60-6

3-chlorophenylboronic acid

nitrobenzene
98-95-3

nitrobenzene

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

Conditions
ConditionsYield
Stage #1: nitrobenzene With [2,2]bipyridinyl; [MoO2Cl2(dmf)2] In toluene for 0.0333333h;
Stage #2: 3-chlorophenylboronic acid With triphenylphosphine In toluene at 100℃; for 20h;
87%
2-(trimethylsilyl)phenyl trifluoromethanesulfonate
88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

3-chloro-aniline
108-42-9

3-chloro-aniline

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

Conditions
ConditionsYield
With cis,trans-2,5-dimethoxytetrahydrofuran; acetonedicarboxylic acid; cesium fluoride In acetonitrile at 20℃;85.7%
aniline
62-53-3

aniline

3-chlorophenyl hydrazine
14763-20-3

3-chlorophenyl hydrazine

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

Conditions
ConditionsYield
With copper phthalocyanine; copper(II) sulfate In methanol at 15℃;85%
With tetrabenzoporphyrinatocobalt(II); copper diacetate In acetonitrile at 0℃; for 13h; chemoselective reaction;55%
triphenyltin chloride
639-58-7

triphenyltin chloride

3-chloro-aniline
108-42-9

3-chloro-aniline

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

Conditions
ConditionsYield
With copper diacetate; triethylamine at 20℃; for 24h;84%
3-Chloronitrobenzene
121-73-3

3-Chloronitrobenzene

phenylboronic acid
98-80-6

phenylboronic acid

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

Conditions
ConditionsYield
Stage #1: 3-Nitrochlorobenzene With [2,2]bipyridinyl; [MoO2Cl2(dmf)2] In toluene for 0.0333333h;
Stage #2: phenylboronic acid With triphenylphosphine In toluene at 100℃; for 20h;
84%
1-bromo-3-chlorobenzene
108-37-2

1-bromo-3-chlorobenzene

aniline
62-53-3

aniline

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

Conditions
ConditionsYield
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 24h; Reflux;82%
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 24h; Reflux;82%
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 24h; Reflux;82%
With potassium hydroxide In N,N-dimethyl-formamide at 130℃; for 0.483333h; Buchwald-Hartwig Coupling;68%
3-chlorophenylboronic acid
63503-60-6

3-chlorophenylboronic acid

aniline
62-53-3

aniline

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

Conditions
ConditionsYield
With 2,6-dimethylpyridine; tetrabutylammonium perchlorate; copper diacetate; triethylamine In acetonitrile at 20℃; for 20h; Chan-Lam Coupling; Electrochemical reaction; chemoselective reaction;75%
With N-(pyrid-2-yl)benzamide; nickel(II) acetate tetrahydrate; N,N,N',N'-tetramethylguanidine In toluene at 60℃; for 24h; Chan-Lam Coupling;74%
With ammonium cerium (IV) nitrate; copper diacetate In toluene at 20℃; for 12h; Chan-Lam Coupling;73%
With 2,6-dimethylpyridine; fac-tris(2-phenylpyridinato-N,C2')iridium(III); copper diacetate; n-tetradecanoic acid In toluene; acetonitrile at 35℃; for 20h; Reagent/catalyst; Chan-Lam Coupling; Irradiation;62%
With C30H25N4O(1-)*3C2H3O2(1-)*2Cu(2+) In methanol at 20℃; for 24h;34 %Spectr.
3-[(4-methylphenyl)sulfonyl]-1-phenyltriaz-1-ene
65739-06-2

3-[(4-methylphenyl)sulfonyl]-1-phenyltriaz-1-ene

3-chlorophenylboronic acid
63503-60-6

3-chlorophenylboronic acid

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 110℃; for 24h; Molecular sieve; Inert atmosphere; Schlenk technique;65%
iodobenzene
591-50-4

iodobenzene

3-chloro-aniline
108-42-9

3-chloro-aniline

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

Conditions
ConditionsYield
With copper; potassium carbonate50%
bromobenzene
108-86-1

bromobenzene

3-Chloroacetanilide
588-07-8

3-Chloroacetanilide

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

Conditions
ConditionsYield
With copper; potassium carbonate; potassium iodide Reagens 4: Nitrobenzol; und Erwaermen des Reaktionsprodukts mit wss.-aethanol. HCl;
With copper(l) iodide; potassium carbonate In nitrobenzene for 15h; Heating;
N-(3-chlorophenyl)anthranilic acid
13278-36-9

N-(3-chlorophenyl)anthranilic acid

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

Conditions
ConditionsYield
at 250 - 260℃;
N-(3-chloro-phenyl)-N-phenyl-benzamide
73347-61-2

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

A

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

B

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With barium dihydroxide; cetyltrimethylammonim bromide In water at 65.5℃; Rate constant; Mechanism; absence of ctab, other reagent, other solvent;
chlorobenzene
108-90-7

chlorobenzene

Phenyl azide
622-37-7

Phenyl azide

A

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

B

N-(4-chlorophenyl)aniline
1205-71-6

N-(4-chlorophenyl)aniline

C

N-phenyl-2-chloroaniline
1205-40-9

N-phenyl-2-chloroaniline

Conditions
ConditionsYield
With trifluorormethanesulfonic acid at 65℃; for 2h; Yield given. Yields of byproduct given;
diazotized N-<3-amino-phenyl>-acetanilide

diazotized N-<3-amino-phenyl>-acetanilide

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

Conditions
ConditionsYield
With copper(l) chloride und nachfolgenden Hydrolyse;
3-chloro-aniline
108-42-9

3-chloro-aniline

halobenzene

halobenzene

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

Conditions
ConditionsYield
for 0.25h; Microwave irradiation;
C15H14ClNO2
349579-42-6

C15H14ClNO2

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

Conditions
ConditionsYield
With potassium hydroxide at 130℃; for 2h;138 mg
aniline
62-53-3

aniline

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium nitrite; hydrogenchloride; sodium acetate / water / 1 h / 0 °C
1.2: 0 - 20 °C
2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 24 h / 110 °C / Molecular sieve; Inert atmosphere; Schlenk technique
View Scheme
3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

chloroacetyl chloride
79-04-9

chloroacetyl chloride

N-chloroacetyl-N-phenyl-m-chloroaniline
83254-79-9

N-chloroacetyl-N-phenyl-m-chloroaniline

Conditions
ConditionsYield
In toluene Heating;95%
In N,N-dimethyl-formamide at 20℃; for 4h;89.6%
In benzene Heating;
In toluene
3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

N,N-diethylcarbamyl chloride
88-10-8

N,N-diethylcarbamyl chloride

N,N-diethyl-N'-(3-chlorophenyl)-N'-phenylurea
883726-46-3

N,N-diethyl-N'-(3-chlorophenyl)-N'-phenylurea

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at 0 - 20℃;89%
iodobenzene
591-50-4

iodobenzene

3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

(m-chlorophenyl)diphenylamine
106336-13-4

(m-chlorophenyl)diphenylamine

Conditions
ConditionsYield
potassium hydroxide; copper In various solvent(s) at 160℃; for 27h;88%
3-chlorodiphenylamine
101-17-7

3-chlorodiphenylamine

sodium isocyanate
917-61-3

sodium isocyanate

1-(m-chlorophenyl)-1-phenylurea
86576-00-3

1-(m-chlorophenyl)-1-phenylurea

Conditions
ConditionsYield
With trifluoroacetic acid In benzene for 5h; Ambient temperature;84%

101-17-7Relevant articles and documents

Practical copper-catalyzed N-arylation of amines with 20% aqueous solution of n-Bu4NOH

Molaei, Hamidreza,Ghanbari, Mohammad Mehdi

, p. 301 - 304 (2012)

N-Arylation of a wide variety of amines with phenylboronic acid catalyzed by copper acetate under 20% aqueous solution of n-Bu4NOH was accomplished in good to excellent yields (up to 92%) and substrate conversions (up to 96%).

Synthesis and characterization of new square planar heteroleptic cationic complexes [Ni(ii) β-oxodithioester-dppe]+; Their use as a catalyst for Chan-Lam coupling

Kumari, Kavita,Kumar, Saurabh,Singh, Krishna Nand,Drew, Michael G. B.,Singh, Nanhai

, p. 12143 - 12153 (2020)

Novel heteroleptic [Ni(ii) β-oxodithioester-dppe]+PF6- complexes (β-oxodithioester = methyl-3-hydroxy-3-benzyl-2-propenedithioate L1 1, methyl-3-hydroxy-3-(p-methoxyphenyl)-2-propenedithioate L2 2, methyl-3-hydroxy-3-(naphthyl)-2-propenedithioate L3 3, methyl-3-hydroxy-3-(p-chlorophenyl)-2-propenedithioate L4 4, methyl-3-hydroxy-3-(p-bromophenyl)-2-propenedithioate L5 5 and methyl-3-hydroxy-3-(p-cyanophenyl)-2-propenedithioate L6 6) have been synthesized and characterized by elemental (C, H, N) analysis, ESI-MS, IR, UV-visible, 1H, 13C{1H}, 31P{1H} and 19F{1H} NMR spectroscopy. The distorted square planar structures of the isomorphous cationic complexes 2, 3, 4 and 5 have been determined by X-ray crystallography. The catalytic activities of 1-6 were investigated for the Chan-Lam coupling reaction involving arylboronic acids and amines to afford N-arylated products in good to excellent yields under mild conditions with 1 mol% catalyst loading. This catalytic protocol offers significant functional group tolerance, and is endowed with a broad substrate scope. This journal is

Triflic Acid Catalyzed Phenylamination of Aromatics with Phenyl Azide

Olah, George A.,Ramaiah, Pichika,Wang, Qi,Prakash, G. K. Surya

, p. 6900 - 6901 (1993)

-

Design, preparation and characterization of aerogel NiO-CuO-CoO/SiO2 nanocomposite as a reusable catalyst for C-N cross-coupling reaction

Ghasemi, Amir Hossein,Naeimi, Hossein

, p. 5056 - 5063 (2020)

Aerogels are porous, non-crystalline solid materials with high specific surface space, plentiful three-dimensional (3D) porous construction, ultra-low density and significant porosity. The aerogel nanocomposite is produced using sol-gel and supercritical drying processes. CO2 supercritical drying (SCD) is the most powerful process, ensuring optimal product properties such as high porosity, low density, and high thermal conductivity. On this account, we used the CO2 supercritical drying method to produce NiO-CuO-CoO/SiO2 nanocomposite aerogels and applied it as a reusable catalyst for the C-N cross-coupling reaction (Buchwald-Hartwig amination). Powerful catalytic activity for the C-N cross-coupling reaction was obtained for the new nanocomposite aerogel, that is, NiO-CuO-CoO/SiO2. The catalyst was characterized by X-ray Powder Diffraction (XRD), field emission scanning electron microscopy (FE-SEM), energy-dispersive X-ray spectroscopy (EDS), elemental mapping and Brunauer-Emmett-Teller (BET). Also, organic compounds were identified by melting point, Fourier-transform infrared spectroscopy (FT-IR) and hydrogen-1 nuclear magnetic resonance (1H NMR) analyses.

Metal-free synthesis of secondary amines by the reaction of tosyl triazene and aryl boronic acid

Sarma, Manas Jyoti,Phukan, Prodeep

, p. 656 - 662 (2018)

A metal free noncatalytic amination process has been developed for the synthesis of N-substituted aniline using a new amine source. The amine source p-toluene sulfonyl triazene (PhN?NNHTs) has been prepared by treating aryldiazonium salt with p-tosylamide. Various unsymmetrical amines could be synthesized by treating this reagent and boronic acid in toluene at 110 °C in the presence of DBU and 4 ? molecular sieve. A large variety of N-substituted aniline could be synthesized with moderate yield.

Visible-Light- And PPh3-Mediated Direct C-N Coupling of Nitroarenes and Boronic Acids at Ambient Temperature

Manna, Kartic,Ganguly, Tanusree,Baitalik, Sujoy,Jana, Ranjan

supporting information, p. 8634 - 8639 (2021/11/01)

We present here a metal-free, visible-light- and triphenylphosphine-mediated intermolecular, reductive amination between nitroarenes and boronic acids at ambient temperature without any photocatalyst. Mechanistically, a slow reduction of nitroarenes to a nitroso and, finally, a nitrene intermediate occurs that leads to the amination product with concomitant 1,2-aryl/-alkyl migration from a boronate complex. A wide range of nitroarenes underwent C-N coupling with aryl-/alkylboronic acids providing high yields.

POLYCYCLIC AROMATIC COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICES USING THE SAME

-

Paragraph 0076-0078, (2020/06/29)

Disclosed are polycyclic aromatic compounds that can be employed in various organic layers of organic electroluminescent devices. Also disclosed are organic electroluminescent devices including the polycyclic aromatic compounds. The organic electroluminescent devices are highly efficient and long lasting and have greatly improved luminous efficiency.

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