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4-Chlorotoluene
Cas No: 106-43-4
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4-Chlorotoluene
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Good quality 4-Chlorotoluene CAS 106-43-4 with factory price
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P-Chlorotoluene
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4-Chlorotoluene
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4-Chlorotoluene
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Factory supply 4-Chlorotoluene
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106-43-4 Usage

Uses

Solvent; dyestuff intermediate; in organic syntheses.

Hazard

Avoid inhalation; strong irritant.

Uses

4-Chlorotoluene is used in a variety of organic synthesis, such as acting as coupling precursors for palladium-catalyzed acylation of acetanilides.

Chemical Properties

colourless liquid

Safety Profile

Moderately toxic by ingestion. Mdly toxic by inhalation. Flammable when exposed to heat or flame. When heated to decomposition it emits toxic fumes of Cl-. See also TOLYL CHLORIDE and CHLORINATED HYDROCARBONS, AROMATIC.

Purification Methods

Dry it with BaO, fractionally distil it, then fractionally crystallise it by partial freezing. [Beilstein 5 IV 806.]
InChI:InChI=1/C7H7Cl/c1-6-4-2-3-5-7(6)8/h2-5H,1H3

106-43-4 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (L04672)  4-Chlorotoluene, 98%    106-43-4 100g 165.0CNY Detail
Alfa Aesar (L04672)  4-Chlorotoluene, 98%    106-43-4 500g 494.0CNY Detail
Alfa Aesar (L04672)  4-Chlorotoluene, 98%    106-43-4 1000g 939.0CNY Detail
Sigma-Aldrich (36697)  4-Chlorotoluene  PESTANAL®, analytical standard 106-43-4 36697-1G 255.06CNY Detail

106-43-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Chlorotoluene

1.2 Other means of identification

Product number -
Other names 4-methyl-chlorobenzene

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:106-43-4 SDS

106-43-4Synthetic route

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

para-chlorotoluene
106-43-4

para-chlorotoluene

Conditions
ConditionsYield
With hydrazine hydrate; C23H40MnNO2P2; potassium tert-butylate In tert-butyl alcohol at 115℃; for 48h; Wolff-Kishner Reduction; Green chemistry;99%
With carbon monoxide; hydrogen; benzene at 190℃; under 176522 Torr; Reagens 4: Octacarbonyldikobalt, Reagens 5: Kobaltcarbonat;
With 2,4,6-trimethyl-pyridine; 4,4'-dimethoxyphenyl disulfide; iridium(lll) bis[2-(2,4-difluorophenyl)-5-methylpyridine-N,C20]-4,40-di-tert-butyl-2,20-bipyridine hexafluorophosphate; triphenylphosphine In toluene for 24h; Irradiation;74 %Chromat.
4-tolyl iodide
624-31-7

4-tolyl iodide

para-chlorotoluene
106-43-4

para-chlorotoluene

Conditions
ConditionsYield
With nickel dichloride In N,N-dimethyl-formamide at 170℃; for 0.0833333h; microwave irradiation;99%
With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; tetrabutyl-ammonium chloride; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 20℃; for 30h; Inert atmosphere; Glovebox; Sealed tube; Irradiation;7 %Chromat.
para-bromotoluene
106-38-7

para-bromotoluene

para-chlorotoluene
106-43-4

para-chlorotoluene

Conditions
ConditionsYield
With nickel dichloride In N,N-dimethyl-formamide at 170℃; for 0.0833333h; microwave irradiation;95%
With trans-bis(glycinato)copper(II) monohydrate; tetramethlyammonium chloride In ethanol at 100℃; for 10h; Reagent/catalyst; Finkelstein Reaction; Schlenk technique; Inert atmosphere;93%
With CuCl-alumina In various solvent(s) at 150℃; for 12h;67%
With copper(I) oxide; tetramethlyammonium chloride; L-proline In ethanol at 110℃; for 20h; Inert atmosphere;98 %Chromat.
With iron(III) chloride; sodium chloride In acetonitrile for 2h; Kinetics; Irradiation; Green chemistry; regioselective reaction;
bromochlorobenzene
106-39-8

bromochlorobenzene

methylzinc chloride
5158-46-3

methylzinc chloride

para-chlorotoluene
106-43-4

para-chlorotoluene

Conditions
ConditionsYield
With palladium; triphenylphosphine In tetrahydrofuran at 70℃; for 12h; Catalytic behavior; Negishi Coupling; Inert atmosphere; Green chemistry;95%
p-toluidine
106-49-0

p-toluidine

para-chlorotoluene
106-43-4

para-chlorotoluene

Conditions
ConditionsYield
With potassium nitrite; potassium chloride; sodium chloride; iron(II) bromide In water at 20 - 80℃; for 6.16667h; Temperature;91%
Stage #1: p-toluidine With para-dodecylbenzenesulfonic acid; sodium nitrite In tetrachloromethane at 20℃;
Stage #2: With triethylamine In tetrachloromethane at 70℃;
45%
With tert.-butylnitrite; copper dichloride In acetonitrile
4-chlorobenzyl bromide
622-95-7

4-chlorobenzyl bromide

para-chlorotoluene
106-43-4

para-chlorotoluene

Conditions
ConditionsYield
With sodium tetrahydroborate; cetyltributylphosphonium bromide In water; toluene at 18℃; for 0h; Product distribution;91%
With sodium tetrahydroborate; water In methanol at 20℃; for 0.25h; regioselective reaction;81%
With phosphonic Acid; iodine In 1,2-dichloro-ethane at 120℃; for 36h; Inert atmosphere;98 %Chromat.
With dithionite(2-) In aq. phosphate buffer; acetonitrile at 4℃; pH=7; Kinetics; Inert atmosphere;
4-methyl-benzenediazonium; tetrachloro cuprate(II)

4-methyl-benzenediazonium; tetrachloro cuprate(II)

para-chlorotoluene
106-43-4

para-chlorotoluene

Conditions
ConditionsYield
In dimethyl sulfoxide Ambient temperature;89%
1-Chloro-4-(chloromethyl)benzene
104-83-6

1-Chloro-4-(chloromethyl)benzene

para-chlorotoluene
106-43-4

para-chlorotoluene

Conditions
ConditionsYield
With methanol; magnesium Ambient temperature;87%
With sodium tetrahydroborate In various solvent(s) at 70℃; for 2h;76%
With Perbenzoic acid; tri-n-butyl-tin hydride In benzene at 90℃; for 12h; Mechanism; in the presence of α-chlorotoluene (competitor), relative reactivity;
(4-chlorophenyl)methanethiol
6258-66-8

(4-chlorophenyl)methanethiol

para-chlorotoluene
106-43-4

para-chlorotoluene

Conditions
ConditionsYield
With di-tert-butyl peroxide; triethyl phosphite In toluene87%
With di-tert-butyl peroxide; triethyl phosphite In acetonitrile at 25℃; for 6h; Irradiation;87%
With hexacarbonyl molybdenum In tetrahydrofuran Heating;61%
dicobalt octacarbonyl In water; benzene at 185 - 190℃; under 46543.3 Torr;44%
4-methylbenzene diazonium
57573-52-1

4-methylbenzene diazonium

para-chlorotoluene
106-43-4

para-chlorotoluene

Conditions
ConditionsYield
With tin(II); chloride; copper(II) nitrate In water Ambient temperature;80%
C20H18ClN3

C20H18ClN3

methyl iodide
74-88-4

methyl iodide

A

para-chlorotoluene
106-43-4

para-chlorotoluene

B

(E)-N-benzylidene-α-methylbenzylamine
98393-39-6

(E)-N-benzylidene-α-methylbenzylamine

C

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
Stage #1: C20H18ClN3 With lithium diisopropyl amide In tetrahydrofuran at 0℃;
Stage #2: methyl iodide In tetrahydrofuran
A n/a
B 80%
C n/a
1-Chloro-4-iodobenzene
637-87-6

1-Chloro-4-iodobenzene

methylmercury(II) iodide
143-36-2

methylmercury(II) iodide

para-chlorotoluene
106-43-4

para-chlorotoluene

Conditions
ConditionsYield
With bis(benzonitrile)palladium(II) dichloride; sodium iodide In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere;78%
2-(4-chlorophenyl)-1,3-dithiolane
23229-32-5

2-(4-chlorophenyl)-1,3-dithiolane

para-chlorotoluene
106-43-4

para-chlorotoluene

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In tetrahydrofuran; methanol at 20℃; for 0.5h;78%
methyl (E)-2-(4-chlorobenzylidene)hydrazine-1-carboxylate

methyl (E)-2-(4-chlorobenzylidene)hydrazine-1-carboxylate

para-chlorotoluene
106-43-4

para-chlorotoluene

Conditions
ConditionsYield
With potassium hydroxide In 2,2'-[1,2-ethanediylbis(oxy)]bisethanol at 140℃; for 4h; Wolff-Kishner Reduction;76%
4-methylbenzenediazonium tetrafluoroborate
459-44-9

4-methylbenzenediazonium tetrafluoroborate

A

p-fluorotoluene
352-32-9

p-fluorotoluene

B

para-chlorotoluene
106-43-4

para-chlorotoluene

Conditions
ConditionsYield
With 1,2-dichloro-ethane Heating;A 74%
B 26 % Chromat.
5-chloro-2-methylbenzoic acid
7499-06-1

5-chloro-2-methylbenzoic acid

para-chlorotoluene
106-43-4

para-chlorotoluene

Conditions
ConditionsYield
With [Au(1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)(O2CAd)] In toluene at 140℃; for 20h;74%
chlorine
7782-50-5

chlorine

toluene
108-88-3

toluene

A

para-chlorotoluene
106-43-4

para-chlorotoluene

B

2-methylchlorobenzene
95-49-8

2-methylchlorobenzene

Conditions
ConditionsYield
With iron(III) chloride In ethanol at 50 - 80℃; for 14h; Temperature; Inert atmosphere;A 26.8%
B 72.3%
toluene
108-88-3

toluene

A

para-chlorotoluene
106-43-4

para-chlorotoluene

B

2-methylchlorobenzene
95-49-8

2-methylchlorobenzene

Conditions
ConditionsYield
With chlorine; natural kaolinitic clay In tetrachloromethane for 2h; Heating;A 72%
B 23%
With aluminum (III) chloride; chlorine at 50℃; for 6h; Temperature; Inert atmosphere;A 71.3%
B 27.8%
With hydrogenchloride; 1-(n-butyl)-3-methylimidazolium triflate at 100℃; for 96h;A 38%
B 60%
1-Chloro-4-(chloromethyl)benzene
104-83-6

1-Chloro-4-(chloromethyl)benzene

A

para-chlorotoluene
106-43-4

para-chlorotoluene

B

1,2-bis(4-chlorophenyl)ethane
5216-35-3

1,2-bis(4-chlorophenyl)ethane

Conditions
ConditionsYield
With nickel In 1,2-dimethoxyethane at 70℃; for 0.5h;A 20%
B 72%
With magnesium at 600℃;A 6%
B 37%
bromochlorobenzene
106-39-8

bromochlorobenzene

(3-dimethylaminopropyl)dimethylgallium

(3-dimethylaminopropyl)dimethylgallium

A

(4,4'-dimethyl-1,1'-biphenyl)
613-33-2

(4,4'-dimethyl-1,1'-biphenyl)

B

para-chlorotoluene
106-43-4

para-chlorotoluene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine)palladium dichloride In benzene at 85℃; for 3h;A 5%
B 70%
4-toluenediazonium o-benzenedisulfonimide

4-toluenediazonium o-benzenedisulfonimide

para-chlorotoluene
106-43-4

para-chlorotoluene

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; copper In acetonitrile at 20℃; for 0.75h; Substitution;68%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

para-chlorotoluene
106-43-4

para-chlorotoluene

Conditions
ConditionsYield
With 2-pentanol; ReOCl3(SMe2)(OPPh3) for 17h; Green chemistry; chemoselective reaction;66%
With polymethylhydrosiloxane; iron(III) chloride hexahydrate In 1,2-dichloro-ethane at 120℃; for 1h; Microwave irradiation;62%
With hydrazine hydrate; diethylene glycol Erhitzen des mit Kaliumhydroxid versetzten Reaktionsgemisches;
With acid; copper cathode bei der elektrolytischen Reduktion;
Multi-step reaction with 2 steps
1: acetic acid / ethanol / Reflux
2: potassium hydroxide / 2,2'-[1,2-ethanediylbis(oxy)]bisethanol / 4 h / 140 °C
View Scheme
1,1-Bis-(4-chlorobenzyl)-1,4-dihydronaphthalene
146450-75-1

1,1-Bis-(4-chlorobenzyl)-1,4-dihydronaphthalene

A

para-chlorotoluene
106-43-4

para-chlorotoluene

B

1-(4-chlorobenzyl)naphthalene
1591-43-1

1-(4-chlorobenzyl)naphthalene

Conditions
ConditionsYield
at 150℃; for 17h;A 50%
B 66%
at 150℃; for 17h; Mechanism; other dihydroaromatic compounds as substrates;A 50%
B 66%
O-4-chlorobenzyl 1H-benzo[d][1,2,3]triazole-1-carbothioate

O-4-chlorobenzyl 1H-benzo[d][1,2,3]triazole-1-carbothioate

para-chlorotoluene
106-43-4

para-chlorotoluene

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In toluene at 110℃; for 0.5h; Temperature; Inert atmosphere; Microwave irradiation; regioselective reaction;66%
perfluoroheptanoic acid
375-85-9

perfluoroheptanoic acid

toluene
108-88-3

toluene

A

para-chlorotoluene
106-43-4

para-chlorotoluene

B

2,2,3,3,4,4,5,5,6,6,7,7,7-Tridecafluoro-heptanoic acid p-tolyl ester
102607-12-5

2,2,3,3,4,4,5,5,6,6,7,7,7-Tridecafluoro-heptanoic acid p-tolyl ester

Conditions
ConditionsYield
With lead(IV) acetate; lithium chlorideA 65%
B 21%
toluene
108-88-3

toluene

A

para-chlorotoluene
106-43-4

para-chlorotoluene

B

2,2,3,3,4,4,5,5,6,6,7,7,7-Tridecafluoro-heptanoic acid p-tolyl ester
102607-12-5

2,2,3,3,4,4,5,5,6,6,7,7,7-Tridecafluoro-heptanoic acid p-tolyl ester

Conditions
ConditionsYield
With lead(IV) acetate; C6F13COOH; lithium chlorideA 65%
B 21%
toluene
108-88-3

toluene

A

para-chlorotoluene
106-43-4

para-chlorotoluene

B

2-methylchlorobenzene
95-49-8

2-methylchlorobenzene

C

2,4-dichlorotoluene
95-73-8

2,4-dichlorotoluene

Conditions
ConditionsYield
With hydrogenchloride; sodium hypochlorite In water at 20℃; Product distribution; Further Variations:; Temperatures; molar quantity of reagents; Chlorination; oxidative chlorination;A 29%
B 63%
C 3.5%
With oxone; potassium chloride In acetonitrile at 20℃; for 24h; Product distribution; Further Variations:; Reagents ratio;
With sulfuric acid; [BMIM]Cl; chlorine at 70℃; for 8h;
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

n-heptan1ol
111-70-6

n-heptan1ol

4-Chlorostyrene oxide
2788-86-5

4-Chlorostyrene oxide

A

para-chlorotoluene
106-43-4

para-chlorotoluene

B

n-heptyl 4-methoxybenzoate
5452-08-4

n-heptyl 4-methoxybenzoate

C

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With 5%-palladium/activated carbon; sodium fluoride In 1,4-dioxane at 150℃; for 6h;A 20 %Chromat.
B 60%
C 9 %Chromat.
2-methylenesuccinic acid
97-65-4

2-methylenesuccinic acid

p-methylbenzenediazonium chloride
2028-84-4

p-methylbenzenediazonium chloride

A

para-chlorotoluene
106-43-4

para-chlorotoluene

B

C12H13ClO4
1427331-01-8

C12H13ClO4

Conditions
ConditionsYield
With copper(II) choride dihydrate In [(2)H6]acetone; water at 25℃; for 2.5h; Meerwein Arylation;A n/a
B 56%
Trichloroethylene
79-01-6

Trichloroethylene

p-methylbenzenediazonium chloride
2028-84-4

p-methylbenzenediazonium chloride

A

para-chlorotoluene
106-43-4

para-chlorotoluene

B

1,1,1,2-Tetrachlor-2-(p-tolyl)ethan
4714-29-8

1,1,1,2-Tetrachlor-2-(p-tolyl)ethan

Conditions
ConditionsYield
With potassium chloride; copper dichloride In water; acetoneA n/a
B 53%
para-chlorotoluene
106-43-4

para-chlorotoluene

toluene
108-88-3

toluene

Conditions
ConditionsYield
With water; sodium iodide; nickel dichloride; zinc; sonication In N,N,N,N,N,N-hexamethylphosphoric triamide at 60℃; for 3h;100%
With water; sodium iodide; nickel dichloride; zinc; sonication In N,N,N,N,N,N-hexamethylphosphoric triamide at 60℃; for 3h; Product distribution;100%
With palladium on ceria; sodium hydroxide In isopropyl alcohol at 40℃; for 24h; Temperature; Solvent; Irradiation; Inert atmosphere; Sealed tube;97%
para-chlorotoluene
106-43-4

para-chlorotoluene

phenylboronic acid
98-80-6

phenylboronic acid

4-Methylbiphenyl
644-08-6

4-Methylbiphenyl

Conditions
ConditionsYield
With Cs2O3; PCy3 adduct of cyclopalladated ferrocenylimine In 1,4-dioxane at 100℃; for 15h; Suzuki cross-coupling reaction;100%
With [PdI(2-(2-thiophenyl)-4,4-dimethyloxazoline)(1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene)]; potassium carbonate In tetrahydrofuran; water at 90℃; for 18h; Catalytic behavior; Reagent/catalyst; Suzuki-Miyaura Coupling;100%
With caesium carbonate; palladium diacetate; 1,3-di-([N-(2,4,6-Me3Ph)imidazolium-3-yl]Me)-2,4,6-Me3Ph*2Cl- In 1,4-dioxane at 80℃; for 1.5h; Suzuki reaction;99%
para-chlorotoluene
106-43-4

para-chlorotoluene

N-methylaniline
100-61-8

N-methylaniline

N,4-dimethyl-N-phenylaniline
38158-65-5

N,4-dimethyl-N-phenylaniline

Conditions
ConditionsYield
With johnphos; sodium t-butanolate; palladium diacetate In toluene at 20℃; for 19h; Arylation;100%
With potassium tert-butylate; Pd(0) N-heterocyclic carbene-phosphine In 1,4-dioxane at 100℃;99%
With potassium hydroxide; bis(tri-tert-butylphosphine)palladium(0); cetyltrimethylammonim bromide In water; toluene at 90℃; for 19h;99%
para-chlorotoluene
106-43-4

para-chlorotoluene

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4-(4-tolyl)anisole
53040-92-9

4-(4-tolyl)anisole

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 3-butyl-1-methyl-5-[9-(3-methyl-1H-imidazol-3-ium-1-yl)nonyl]-3H-1,2,3-triazol-1-ium diiodide; caesium carbonate In 1,4-dioxane Suzuki-Miyaura reaction; Inert atmosphere; Heating;100%
With tris(dibenzylideneacetone)dipalladium (0); C3H3N2(C9H11)2*HCl; caesium carbonate In 1,4-dioxane at 80℃; for 1.5h;99%
Stage #1: 4-methoxyphenylboronic acid With allyl(1,3-bis(2,6-diisopropyl-4-(3-((3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)oxy)propyl)phenyl)-imidazol-2-ylidene)palladium(II) chloride; potassium tert-butylate In ethanol at 30℃; for 0.5h; Inert atmosphere;
Stage #2: para-chlorotoluene In ethanol at 30℃; for 4h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Suzuki Coupling; Inert atmosphere;
99%
para-chlorotoluene
106-43-4

para-chlorotoluene

1-phenyl-propan-1-one
93-55-0

1-phenyl-propan-1-one

1-phenyl-2-p-tolylpropan-1-one
107271-15-8

1-phenyl-2-p-tolylpropan-1-one

Conditions
ConditionsYield
With sodium t-butanolate; Pd(dba)2*n-butylbis(1-adamantyl)phosphine In toluene at 80℃; for 20h;100%
With [Ipent.H][Pd(η3-cin)Cl2]; sodium t-butanolate at 60 - 80℃; for 2h; Buchwald-Hartwig Coupling; Sealed tube;99%
With sodium t-butanolate; [(N,N'-bis(2,6-di-iPr-phenyl)imidazol-2-ylidene)Pd(acac)Cl] In toluene at 100℃; for 0.5h;98%
para-chlorotoluene
106-43-4

para-chlorotoluene

methyl [3,4-13C2]2-deoxyriboside
267411-72-3

methyl [3,4-13C2]2-deoxyriboside

methyl [3,4-13C2]3,5-toluyl-2-deoxyriboside

methyl [3,4-13C2]3,5-toluyl-2-deoxyriboside

Conditions
ConditionsYield
With pyridine at 40℃; for 2h; Arylation;100%
para-chlorotoluene
106-43-4

para-chlorotoluene

9-phenyl-9H-xanthen-9-ol
596-38-3

9-phenyl-9H-xanthen-9-ol

A

xanth-9-one
90-47-1

xanth-9-one

B

4-Methylbiphenyl
644-08-6

4-Methylbiphenyl

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; tricyclohexylphosphine In o-xylene for 4h; Heating;A n/a
B 100%
para-chlorotoluene
106-43-4

para-chlorotoluene

(meta-(trifluoromethyl)phenyl)boronic acid
1423-26-3

(meta-(trifluoromethyl)phenyl)boronic acid

4’-methyl-3-(trifluoromethyl)-1,1’-biphenyl
97067-19-1

4’-methyl-3-(trifluoromethyl)-1,1’-biphenyl

Conditions
ConditionsYield
With potassium phosphate; N,N-diisopropyl 2-dicyclohexylphosphino-4-phenylbenzamide; tris(dibenzylideneacetone)dipalladium (0) In toluene at 110℃; for 5h; Suzuki cross-coupling reaction;100%
2-phenylpyridine
1008-89-5

2-phenylpyridine

para-chlorotoluene
106-43-4

para-chlorotoluene

2-(4’-methyl-[1,1’-biphenyl]-2-yl)pyridine

2-(4’-methyl-[1,1’-biphenyl]-2-yl)pyridine

Conditions
ConditionsYield
With dichloro[1-(3-methylbenzyl)-3-(n-butyl)benzimidazol-2-ylidene]ruthenium(II); potassium acetate In water at 100℃; for 5h; Reagent/catalyst;100%
With C36H35Cl2PRu; potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 24h; regioselective reaction;86%
para-chlorotoluene
106-43-4

para-chlorotoluene

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

1-(4-methoxyphenyl)-2-(4-methylphenyl)ethanone
57297-25-3

1-(4-methoxyphenyl)-2-(4-methylphenyl)ethanone

Conditions
ConditionsYield
With C40H48ClN3Pd; sodium t-butanolate In 1,4-dioxane at 100℃; for 4h; Reagent/catalyst;100%
With [Ni(1,3-bis[2,6-bis(diphenylmethyl)-4-methylphenyl]imidazole-2-ylidene)(cin)Cl]; sodium t-butanolate In toluene at 80℃; for 16h;86%
With (C5H5)Fe(C5H3C(CH3)NC6H4CH3)PdCl(CN2(C6H3(CH(CH3)2)2)2C2H2); potassium tert-butylate In toluene for 5h; Inert atmosphere; Reflux;80%
With [Pd(IHept)(acac)Cl]; sodium t-butanolate In toluene at 100℃; for 16h; Glovebox;70%
para-chlorotoluene
106-43-4

para-chlorotoluene

C7H6ClK

C7H6ClK

Conditions
ConditionsYield
Stage #1: para-chlorotoluene With potassium tert-butylate for 0.333333h; Cooling;
Stage #2: With n-butyllithium In hexane at -35 - 20℃; for 5h;
100%
para-chlorotoluene
106-43-4

para-chlorotoluene

thiourea
17356-08-0

thiourea

S-(4-methylphenyl)isothiouronium chloride

S-(4-methylphenyl)isothiouronium chloride

Conditions
ConditionsYield
In ethanol for 1h; Reflux;100%
8-(4-oxocyclohexyl)-1,4-dioxaspiro[4.5]decane
56309-94-5

8-(4-oxocyclohexyl)-1,4-dioxaspiro[4.5]decane

para-chlorotoluene
106-43-4

para-chlorotoluene

C21H30O3

C21H30O3

Conditions
ConditionsYield
Stage #1: para-chlorotoluene With iodine; magnesium In tetrahydrofuran at 57 - 80℃; for 5h; Inert atmosphere;
Stage #2: 8-(4-oxocyclohexyl)-1,4-dioxaspiro[4.5]decane In tetrahydrofuran; toluene at 55 - 60℃; for 1h; Temperature; Solvent; Inert atmosphere;
100%
para-chlorotoluene
106-43-4

para-chlorotoluene

para-chlorobenzoic acid
74-11-3

para-chlorobenzoic acid

Conditions
ConditionsYield
With Oxone; potassium bromide In dichloromethane; water at 20℃; for 24h; visible light irradiation;99%
With ruthenium trichloride; sodium hypochlorite; tetrabutylammomium bromide In 1,2-dichloro-ethane at 25℃; for 2h;98%
With ruthenium trichloride; sodium hypochlorite; tetrabutylammomium bromide In 1,2-dichloro-ethane at 25℃; for 2h; Rate constant; Mechanism; pH 9: other methylbenzenes; var. concentration of aq. NaOCl, ruthenium and tetrabutylammonium bromide;98%
para-chlorotoluene
106-43-4

para-chlorotoluene

(4,4'-dimethyl-1,1'-biphenyl)
613-33-2

(4,4'-dimethyl-1,1'-biphenyl)

Conditions
ConditionsYield
With styrene; [2,2]bipyridinyl; sodium hydride; bis(acetylacetonate)nickel(II); aluminium(III) acetylacetonate In tetrahydrofuran for 3h; Ullmann coupling; Heating;99%
With potassium tert-butylate; palladium diacetate; bis(pinacol)diborane; XPhos for 12h; Heating;99%
With samarium; triphenylphosphine; nickel dichloride In N,N-dimethyl-formamide at 40℃; for 1.5h;98%
para-chlorotoluene
106-43-4

para-chlorotoluene

p-toluidine
106-49-0

p-toluidine

di-p-tolylamine
620-93-9

di-p-tolylamine

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)); potassium tert-butylate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In 1,4-dioxane at 100℃; for 1.5h; Inert atmosphere;99%
With dihydrogen dichloro-bis(di-tert-butylphosphinito-κP)palladium(2-); sodium t-butanolate In 1,4-dioxane at 110℃; for 4h;97%
With potassium hydroxide; tert-butyl alcohol; cyclopalladated ferrocenylimine monophosphinobiaryl complex In water at 95℃; for 24h; Buchwald-Hartwig amination;97%
piperidine
110-89-4

piperidine

para-chlorotoluene
106-43-4

para-chlorotoluene

N-(4-methylphenyl)piperidine
31053-03-9

N-(4-methylphenyl)piperidine

Conditions
ConditionsYield
With (N,N'-diarylimidazol-2-ylidene)-based palladacycle; sodium t-butanolate In 1,4-dioxane at 70℃; for 0.5h;99%
With tris(dibenzylideneacetone)dipalladium (0); potassium tert-butylate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 1,4-dioxane at 100℃;98%
With tris-(dibenzylideneacetone)dipalladium(0); keYPhos; potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Glovebox; Inert atmosphere;98%
para-chlorotoluene
106-43-4

para-chlorotoluene

N-butylamine
109-73-9

N-butylamine

N-butyl-4-methylaniline
10387-24-3

N-butyl-4-methylaniline

Conditions
ConditionsYield
With potassium phosphate In dimethyl sulfoxide at 80℃; UV-irradiation;99%
With tris-(dibenzylideneacetone)dipalladium(0); 4-dicyclohexylphosphino-12-(2',6'-dimethoxy)phenyl-[2.2]paracyclophane; sodium t-butanolate In 1,4-dioxane at 100℃; for 6h; Buchwald-Hartwig amination; Inert atmosphere;93%
With palladium diacetate; (R)-1-[(SP)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; sodium t-butanolate In toluene at 85℃; for 2h;89%
para-chlorotoluene
106-43-4

para-chlorotoluene

aniline
62-53-3

aniline

4-methyldiphenylamine
620-84-8

4-methyldiphenylamine

Conditions
ConditionsYield
With (R)-1-[(SP)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 110℃; for 16h; Mechanism; Product distribution; other amines; other aryl halides and tosylates; var. chelating alkylphosphines, var. time, var. temp., further solvent;99%
With (R)-1-[(SP)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 110℃; for 16h;99%
With potassium tert-butylate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 100℃; for 5h;99%
para-chlorotoluene
106-43-4

para-chlorotoluene

benzylamine
100-46-9

benzylamine

N-benzyl-N-(4-methylphenyl)amine
5405-15-2

N-benzyl-N-(4-methylphenyl)amine

Conditions
ConditionsYield
With C40H42NP; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In 1,4-dioxane; water at 20℃; for 1.16667h; Reagent/catalyst; Inert atmosphere; Sealed tube; Reflux;99%
With potassium tert-butylate; C46H69ClP2Pd In tetrahydrofuran at 20℃; for 6h; Reagent/catalyst; Schlenk technique; Inert atmosphere;96%
With palladium diacetate; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; sodium t-butanolate In toluene at 100℃; for 24h;95%
para-chlorotoluene
106-43-4

para-chlorotoluene

2-Methylphenylboronic acid
16419-60-6

2-Methylphenylboronic acid

2,4'-dimethylbiphenyl
611-61-0

2,4'-dimethylbiphenyl

Conditions
ConditionsYield
With caesium carbonate; palladium diacetate; 1,3-di-([N-(2,4,6-Me3Ph)imidazolium-3-yl]Me)-2,4,6-Me3Ph*2Cl- In 1,4-dioxane at 80℃; for 4h; Suzuki reaction;99%
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); 3-(dicyclohexylphosphino)-2-(2,6-dimethoxyphenyl)-1-methyl-1H-indole In 1,4-dioxane at 100℃; for 24h; Suzuki-Miyaura Coupling; Schlenk technique; Sealed tube; Inert atmosphere;97%
With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; tricyclohexylphosphine In tetrahydrofuran at 20℃; for 30h; Suzuki coupling;92%
morpholine
110-91-8

morpholine

para-chlorotoluene
106-43-4

para-chlorotoluene

4-(4-methylphenyl)morpholine
3077-16-5

4-(4-methylphenyl)morpholine

Conditions
ConditionsYield
With potassium tert-butylate; Pd(0) N-heterocyclic carbene-phosphine In 1,4-dioxane at 100℃;99%
With palladium diacetate; sodium t-butanolate; ruphos In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Green chemistry;99%
With dichloro(3-chloropyridinyl)(1,3-(diisopropylphenyl)-4,5-bis(dimethylamino)imidazol-2-ylidene)palladium(II); potassium tert-butylate In 1,4-dioxane at 80℃; for 18h; Catalytic behavior; Solvent; Temperature; Reagent/catalyst; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique; Sealed tube;99%
para-chlorotoluene
106-43-4

para-chlorotoluene

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

(4,4'-dimethyl-1,1'-biphenyl)
613-33-2

(4,4'-dimethyl-1,1'-biphenyl)

Conditions
ConditionsYield
With caesium carbonate; palladium diacetate; 1,3-di-([N-(2,4,6-Me3Ph)imidazolium-3-yl]Me)-2,4,6-Me3Ph*2Cl- In 1,4-dioxane at 80℃; for 4h; Suzuki reaction;99%
With potassium phosphate; poly{[1,1'-bis-(1,4-phenylene-C(PPh2))ferrocene]-derivative}; bis(1,5-cyclooctadiene)nickel (0) In tetrahydrofuran for 24h; Suzuki cross-coupling; Heating;99%
With potassium phosphate; ferrocenylmethylphosphine; bis(1,5-cyclooctadiene)nickel (0) In tetrahydrofuran at 20℃; for 48h; Suzuki-Miyaura cross-coupling;98%
para-chlorotoluene
106-43-4

para-chlorotoluene

phenylmagnesium bromide

phenylmagnesium bromide

4-Methylbiphenyl
644-08-6

4-Methylbiphenyl

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium (0); N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride In tetrahydrofuran; 1,4-dioxane at 80℃; for 3h; Phenylation;99%
With [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene; Ni(1,5-bis-cyclooctadiene)2 In various solvent(s) Kumada-Corriu cross-coupling reaction;88%
With N-heterocyclic carbene-based nickel(II) complex In tetrahydrofuran at 20℃; for 12h; Kumada reaction;83%
With 1-[2-(diphenylphosphino)phenyl]ethanol; bis(acetylacetonate)nickel(II) In diethyl ether at 20℃; for 0.333333h;97 % Chromat.
para-chlorotoluene
106-43-4

para-chlorotoluene

diphenylamine
122-39-4

diphenylamine

diphenyl(p-tolyl)amine
4316-53-4

diphenyl(p-tolyl)amine

Conditions
ConditionsYield
With PdCl(π-allyl)(cyclohexyl-(1-methyl-2,2-diphenylcyclopropylphophine)); sodium t-butanolate In tetrahydrofuran; toluene at 100℃; for 0.25h; Reagent/catalyst; Buchwald-Hartwig Coupling; Inert atmosphere;99%
With palladium diacetate; sodium t-butanolate; ruphos In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Green chemistry;99%
With sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0); P(i-BuNCH2CH2)3N In toluene at 100℃; for 20h; Buchwald-Hartwig amination;98%
Benzophenone imine
1013-88-3

Benzophenone imine

para-chlorotoluene
106-43-4

para-chlorotoluene

N-(diphenylmethylene)-p-toluidine
24215-01-8

N-(diphenylmethylene)-p-toluidine

Conditions
ConditionsYield
With potassium tert-butylate; bis(dibenzylideneacetone)-palladium(0); 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 1,4-dioxane at 100℃; for 4h;99%
With 1,8-bis(diisopropylphosphino)triptycene; potassium phosphate; palladium diacetate In toluene Buchwald-Hartwig amination;99%
With potassium tert-butylate; Pd(0) N-heterocyclic carbene-phosphine In 1,4-dioxane at 100℃;98%
With (±)-[2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]bis(triphenylphosphite)nickel(0) toluene solvate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃; Inert atmosphere;97%
With bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene In Dimethyl ether at 55℃; for 18h; Amination;94%
styrene
292638-84-7

styrene

para-chlorotoluene
106-43-4

para-chlorotoluene

Conditions
ConditionsYield
With tetrabutylammonium acetate; palladium diacetate; DavePhos In 1,4-dioxane at 80℃; for 24h; Heck reaction; Inert atmosphere; Sealed tube;99%
With tetrakis[μ-1-[(3-methoxyphenyl)methyl]-2-phenyl-3-[2-oxo-2-[(2-phenolato-kO)aminokN]ethyl]-1H-imidazoliumato-kC4]tetrapalladium; tetrabutylammomium bromide; sodium acetate at 140℃; for 12h; Heck Reaction;99%
With potassium phosphate; catacxium A; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 120℃; for 24h; Substitution; Heck reaction;98%
para-chlorotoluene
106-43-4

para-chlorotoluene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

p-tolylboronic pinacol ester
195062-57-8

p-tolylboronic pinacol ester

Conditions
ConditionsYield
With sodium acetate; bis(dibenzylideneacetone)-palladium(0); XPhos for 12h; Miyaura Borylation Reaction; Heating;99%
With potassium phosphate tribasic heptahydrate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); XPhos In ethanol at 20℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Solvent;98%
With potassium acetate In isopropyl alcohol at 82℃; for 2h; Suzuki-Miyaura Coupling;94%
para-chlorotoluene
106-43-4

para-chlorotoluene

benzamide
55-21-0

benzamide

N-(4-methylphenyl)benzamide
582-78-5

N-(4-methylphenyl)benzamide

Conditions
ConditionsYield
With 4-diphenylphosphino-13-dicyclohexylphosphino-[2.2]paracyclophane; water; palladium diacetate; caesium carbonate In 1,4-dioxane at 150℃; for 5h; Buchwald-Hartwig coupling; Microwave irradiation;99%
With copper(l) iodide; potassium carbonate; trans-N,N'-dimethylcyclohexane-1,2-diamine at 110℃; for 23h;96%
With copper(l) iodide; potassium carbonate; trans-N,N'-dimethylcyclohexane-1,2-diamine at 110℃; for 23h;96%

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