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106-39-8 Usage

Chemical Properties

white to almost white crystalline powder

Uses

1-Bromo-4-chlorobenzene is used as a pharmaceutical intermediate.

Synthesis Reference(s)

Journal of the American Chemical Society, 86, p. 964, 1964 DOI: 10.1021/ja01059a073The Journal of Organic Chemistry, 55, p. 3415, 1990 DOI: 10.1021/jo00297a087

Check Digit Verification of cas no

The CAS Registry Mumber 106-39-8 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 6 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 106-39:
(5*1)+(4*0)+(3*6)+(2*3)+(1*9)=38
38 % 10 = 8
So 106-39-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H4BrCl/c7-5-1-3-6(8)4-2-5/h1-4H

106-39-8 Well-known Company Product Price

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  • TCI America

  • (B0571)  1-Bromo-4-chlorobenzene  >99.0%(GC)

  • 106-39-8

  • 25g

  • 165.00CNY

  • Detail
  • TCI America

  • (B0571)  1-Bromo-4-chlorobenzene  >99.0%(GC)

  • 106-39-8

  • 100g

  • 375.00CNY

  • Detail
  • TCI America

  • (B0571)  1-Bromo-4-chlorobenzene  >99.0%(GC)

  • 106-39-8

  • 500g

  • 875.00CNY

  • Detail
  • Alfa Aesar

  • (A12160)  1-Bromo-4-chlorobenzene, 98+%   

  • 106-39-8

  • 100g

  • 214.0CNY

  • Detail
  • Alfa Aesar

  • (A12160)  1-Bromo-4-chlorobenzene, 98+%   

  • 106-39-8

  • 250g

  • 290.0CNY

  • Detail
  • Alfa Aesar

  • (A12160)  1-Bromo-4-chlorobenzene, 98+%   

  • 106-39-8

  • 1000g

  • 1146.0CNY

  • Detail

106-39-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Bromochlorobenzene

1.2 Other means of identification

Product number -
Other names 1-Bromo-4-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:106-39-8 SDS

106-39-8Synthetic route

p-chlorobenzenediazonium tetrafluoroborate
673-41-6

p-chlorobenzenediazonium tetrafluoroborate

bromochlorobenzene
106-39-8

bromochlorobenzene

Conditions
ConditionsYield
With dibenzo-18-crown-6; potassium bromide; copper(ll) bromide; 1,10-Phenanthroline; copper(I) bromide In acetonitrile at 20℃; for 0.333333h; Sandmeyer bromination;99%
With N-Bromosuccinimide; tetrabutylammonium perchlorate In methanol; N,N-dimethyl-formamide at 20℃; for 3h; Sandmeyer Reaction; Electrochemical reaction;52%
chlorobenzene
108-90-7

chlorobenzene

bromochlorobenzene
106-39-8

bromochlorobenzene

Conditions
ConditionsYield
With sulfuric acid; tetramethylammonium bromide at 120℃; for 3h; Product distribution; Further Variations:; Reagents;98%
With sulfuric acid; potassium bromide at 60℃; for 2h;95%
With Oxone; sodium bromide In water at 20℃; for 3h; regioselective reaction;90%
p-Toluolsulfonylnitrit
66021-66-7

p-Toluolsulfonylnitrit

A

bromochlorobenzene
106-39-8

bromochlorobenzene

B

N,N'-bis(p-toluenesulfonyl)hydroxylamine
56410-24-3

N,N'-bis(p-toluenesulfonyl)hydroxylamine

Conditions
ConditionsYield
With 4-bromo-aniline; copper dichloride In acetonitrile at 25℃; for 1h;A 93%
B 83%
4-bromo-aniline
106-40-1

4-bromo-aniline

A

bromochlorobenzene
106-39-8

bromochlorobenzene

B

N,N'-bis(p-toluenesulfonyl)hydroxylamine
56410-24-3

N,N'-bis(p-toluenesulfonyl)hydroxylamine

Conditions
ConditionsYield
With p-toluenesulfonyl nitrite; copper dichloride In acetonitrile for 0.75h;A 93%
B n/a
4-Chlorophenylboronic acid
1679-18-1

4-Chlorophenylboronic acid

bromochlorobenzene
106-39-8

bromochlorobenzene

Conditions
ConditionsYield
With sodium nitrite In acetonitrile at 80℃; for 1h; Sealed tube;93%
With N-Bromosuccinimide In acetonitrile at 81℃; for 8h;65%
4-bromo-benzenediazonium; tetrachloro cuprate(II)

4-bromo-benzenediazonium; tetrachloro cuprate(II)

bromochlorobenzene
106-39-8

bromochlorobenzene

Conditions
ConditionsYield
In dimethyl sulfoxide Ambient temperature;92%
4-bromo-2,4,6-trimethyldiphenyliodonium trifluoromethanesulfonate
1203709-75-4

4-bromo-2,4,6-trimethyldiphenyliodonium trifluoromethanesulfonate

bromochlorobenzene
106-39-8

bromochlorobenzene

Conditions
ConditionsYield
With copper(l) chloride In acetonitrile at 80℃; for 2h;89%
(4-chlorophenyl)(mesityl)iodonium trifluoromethanesulfonate
1204518-00-2

(4-chlorophenyl)(mesityl)iodonium trifluoromethanesulfonate

bromochlorobenzene
106-39-8

bromochlorobenzene

Conditions
ConditionsYield
With copper(I) bromide In acetonitrile at 80℃; for 2h;85%
4-bromo-aniline
106-40-1

4-bromo-aniline

bromochlorobenzene
106-39-8

bromochlorobenzene

Conditions
ConditionsYield
With N-chloro-succinimide; sodium nitrite In N,N-dimethyl-formamide at 20℃; for 6h;83%
With tert.-butylnitrite; N-benzyl-N,N,N-triethylammonium chloride; copper dichloride; 10-camphorsulfonic acid In acetonitrile at 20℃; for 24h; Time; Solvent;43%
1-(p-chlorophenyl)-3,3-dimethyl-1-triazene
7203-90-9

1-(p-chlorophenyl)-3,3-dimethyl-1-triazene

bromochlorobenzene
106-39-8

bromochlorobenzene

Conditions
ConditionsYield
With methanesulfonic acid; tetrabutyl-ammonium chloride; copper In acetonitrile at 40℃; for 0.25h;82%
potassium 4-bromophenyltrifluoroborate
374564-35-9

potassium 4-bromophenyltrifluoroborate

bromochlorobenzene
106-39-8

bromochlorobenzene

Conditions
ConditionsYield
With trichloroisocyanuric acid In water; ethyl acetate at 20℃; for 1h; Open flask;81%
4-chloro-aniline
106-47-8

4-chloro-aniline

A

bromochlorobenzene
106-39-8

bromochlorobenzene

B

N,N'-bis(p-toluenesulfonyl)hydroxylamine
56410-24-3

N,N'-bis(p-toluenesulfonyl)hydroxylamine

Conditions
ConditionsYield
With p-toluenesulfonyl nitrite; copper(ll) bromide In acetonitrile at 25℃; for 0.0166667h;A 79%
B n/a
4-bromo-phenol
106-41-2

4-bromo-phenol

bromochlorobenzene
106-39-8

bromochlorobenzene

Conditions
ConditionsYield
With phenylphosphorus tetrachloride at 160℃;78%
4-(chloro)benzenediazonium benzo[d][1,3,2]dithiazol-2-ide-1,1,3,3-tetraoxide

4-(chloro)benzenediazonium benzo[d][1,3,2]dithiazol-2-ide-1,1,3,3-tetraoxide

bromochlorobenzene
106-39-8

bromochlorobenzene

Conditions
ConditionsYield
With tetrabutylammomium bromide; copper In acetonitrile at 20℃; for 0.75h; Substitution;75%
With tetrabutylammomium bromide In acetonitrile at 60℃; for 0.75h; Substitution;73%
Multi-step reaction with 2 steps
1: 90 percent / aq. NaOH / 0.5 h / 0 - 5 °C
2: 82 percent / Bu4N(+)Cl(-); MeSO3H; Cu / acetonitrile / 0.25 h / 40 °C
View Scheme
4-Bromobenzenediazonium o-benzenedisulfonimide

4-Bromobenzenediazonium o-benzenedisulfonimide

bromochlorobenzene
106-39-8

bromochlorobenzene

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; copper In acetonitrile at 20℃; Substitution;74%
4-chlorophenylhydrazine hydrochloride
1073-70-7

4-chlorophenylhydrazine hydrochloride

bromochlorobenzene
106-39-8

bromochlorobenzene

Conditions
ConditionsYield
With boron tribromide; dimethyl sulfoxide at 80℃; for 1h;72%
4-chlorophenyldiazonium salt
17333-85-6

4-chlorophenyldiazonium salt

bromochlorobenzene
106-39-8

bromochlorobenzene

Conditions
ConditionsYield
With tin(II); chloride; copper(II) nitrate In water for 0.5h; Ambient temperature;70%
With copper(I) bromide
4-chloro-aniline
106-47-8

4-chloro-aniline

bromochlorobenzene
106-39-8

bromochlorobenzene

Conditions
ConditionsYield
With N-Bromosuccinimide; sodium nitrite In N,N-dimethyl-formamide at 20℃; for 6h;68%
With tert.-butylnitrite; tetrabutylammomium bromide; copper(I) bromide; 10-camphorsulfonic acid In acetonitrile at 20℃; for 24h; Reagent/catalyst; Time; Solvent;61%
With tert.-butylnitrite; tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(ll) bromide In acetonitrile at 20℃; for 23h;58%
2-methylenesuccinic acid
97-65-4

2-methylenesuccinic acid

(4-bromophenyl)diazonium chloride
2028-85-5

(4-bromophenyl)diazonium chloride

A

bromochlorobenzene
106-39-8

bromochlorobenzene

B

C11H10BrClO4
1427331-03-0

C11H10BrClO4

Conditions
ConditionsYield
With copper(II) choride dihydrate In [(2)H6]acetone; water at 25℃; for 2.5h; Meerwein Arylation;A n/a
B 62%
chlorobenzene
108-90-7

chlorobenzene

A

bromochlorobenzene
106-39-8

bromochlorobenzene

B

2-bromo-1-chlorobenzene
694-80-4

2-bromo-1-chlorobenzene

Conditions
ConditionsYield
With N-Bromosuccinimide; iron(III) chloride In acetonitrile for 2h;A 57%
B 38%
With potassium bromate In sulfuric acid; acetic acid for 1h; Heating; Yields of byproduct given;A 52%
B n/a
With potassium bromate In sulfuric acid; acetic acid for 1h; Heating; Yield given;A 52%
B n/a
bromobenzene
108-86-1

bromobenzene

bromochlorobenzene
106-39-8

bromochlorobenzene

Conditions
ConditionsYield
With lead(IV) acetate; tin(IV) chloride In dichloromethane for 20h;56%
With thallium chloride at 100℃; durch Chlorierung;
With iron(III) chloride
1-(4-chlorophenyl)silatrane
29025-67-0

1-(4-chlorophenyl)silatrane

bromochlorobenzene
106-39-8

bromochlorobenzene

Conditions
ConditionsYield
With N-Bromosuccinimide In dichloromethane for 8h; Ambient temperature;52%
Trichloroethylene
79-01-6

Trichloroethylene

(4-bromophenyl)diazonium chloride
2028-85-5

(4-bromophenyl)diazonium chloride

A

bromochlorobenzene
106-39-8

bromochlorobenzene

B

1-Brom-4-<1,2,2,2-tetrachlor-ethyl>-benzol
4714-31-2

1-Brom-4-<1,2,2,2-tetrachlor-ethyl>-benzol

Conditions
ConditionsYield
With potassium chloride; copper dichloride In water; acetoneA n/a
B 52%
(4-bromophenyl)diazonium chloride
2028-85-5

(4-bromophenyl)diazonium chloride

A

bromochlorobenzene
106-39-8

bromochlorobenzene

B

1-Brom-4-<1,2,2,2-tetrachlor-ethyl>-benzol
4714-31-2

1-Brom-4-<1,2,2,2-tetrachlor-ethyl>-benzol

Conditions
ConditionsYield
With Trichloroethylene; potassium chloride; copper dichloride In water; acetoneA n/a
B 52%
C7H6ClN7
93680-29-6

C7H6ClN7

bromochlorobenzene
106-39-8

bromochlorobenzene

Conditions
ConditionsYield
With tetrabutylammomium bromide; trifluoroacetic acid In acetonitrile at 70 - 80℃;40%
p-chlorobenzenediazonium tetrafluoroborate
673-41-6

p-chlorobenzenediazonium tetrafluoroborate

A

bromochlorobenzene
106-39-8

bromochlorobenzene

B

1-Chloro-4-fluorobenzene
352-33-0

1-Chloro-4-fluorobenzene

C

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
With trimethylsilyl bromide; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; copper(I) bromide at 70℃; Schiemann reaction;A 4%
B 61 % Chromat.
C 35%
2-nitro-aniline
88-74-4

2-nitro-aniline

bromochlorobenzene
106-39-8

bromochlorobenzene

Conditions
ConditionsYield
With tert-Butyl thionitrate; Bromoform for 0.5h; Heating;25%
chlorobenzene
108-90-7

chlorobenzene

A

bromochlorobenzene
106-39-8

bromochlorobenzene

B

1-bromo-3-chlorobenzene
108-37-2

1-bromo-3-chlorobenzene

Conditions
ConditionsYield
With bromine trifluoride; bromine at 0 - 10℃;A 25%
B 5%
para-chlorobenzoic acid
74-11-3

para-chlorobenzoic acid

bromochlorobenzene
106-39-8

bromochlorobenzene

Conditions
ConditionsYield
With bromine; mercury(II) oxide In nitrobenzene at 180 - 185℃; for 2h;22%
bromochlorobenzene
106-39-8

bromochlorobenzene

4,4'-dichlorobiphenyl
2050-68-2

4,4'-dichlorobiphenyl

Conditions
ConditionsYield
With [Pd{C6H4(CH2N(CH2Ph)2)}(μ-Br)]2; potassium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 3h; Microwave irradiation; chemoselective reaction;100%
Stage #1: bromochlorobenzene With tert.-butyl lithium In diethyl ether at -78℃;
Stage #2: In diethyl ether
Stage #3: With Duroquinone In diethyl ether
96%
With potassium carbonate In N,N-dimethyl-formamide for 0.666667h;96%
bromochlorobenzene
106-39-8

bromochlorobenzene

benzene
71-43-2

benzene

Conditions
ConditionsYield
With potassium hydroxide; hydrogen; palladium on activated charcoal; Aliquat 336 In water at 50℃; for 0.833333h;100%
With di-tert-butyl peroxide; caesium carbonate; isopropyl alcohol at 120℃; for 3h; Inert atmosphere;93 %Chromat.
With ammonium formate In methanol at 20℃; for 16h;
bromochlorobenzene
106-39-8

bromochlorobenzene

phenylboronic acid
98-80-6

phenylboronic acid

4'-biphenyl chloride
2051-62-9

4'-biphenyl chloride

Conditions
ConditionsYield
With potassium carbonate In ethanol at 80℃; for 36h; Suzuki-Miyaura Coupling; Inert atmosphere;100%
With C28H38Cl2N2O6PdS2(2-)*2Na(1+); tetrabutylammomium bromide; potassium carbonate In water at 75℃; Suzuki coupling; Inert atmosphere;99%
With Br(1-)*C28H29BrN5O2Pd(1+); potassium carbonate In methanol; water at 100℃; for 3h; Suzuki-Miyaura coupling;99%
bromochlorobenzene
106-39-8

bromochlorobenzene

diphenylamine
122-39-4

diphenylamine

(p-chlorophenyl)diphenylamine
4316-56-7

(p-chlorophenyl)diphenylamine

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium 10% on activated carbon; sodium t-butanolate In 1,3,5-trimethyl-benzene for 24h; Inert atmosphere; Reflux;100%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 80℃;90.7%
With tris-(dibenzylideneacetone)dipalladium(0); johnphos; sodium t-butanolate In toluene at 100℃; for 24h; Buchwald-Hartwig Coupling; Sealed tube; Inert atmosphere;79%
bromochlorobenzene
106-39-8

bromochlorobenzene

tert-butyl 1,4-diazepine-1-carboxylate
112275-50-0

tert-butyl 1,4-diazepine-1-carboxylate

tert-butyl 4-(4-chlorophenyl)-1,4-diazepane-1-carboxylate
868063-67-6

tert-butyl 4-(4-chlorophenyl)-1,4-diazepane-1-carboxylate

Conditions
ConditionsYield
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene for 23h; Heating / reflux;100%
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene for 23h; Heating / reflux;100%
bromochlorobenzene
106-39-8

bromochlorobenzene

potassium 3-aminothiophene-2-carboxylate
1210469-45-6

potassium 3-aminothiophene-2-carboxylate

3-amino-2-(4-chlorophenyl)thiophene
183676-87-1

3-amino-2-(4-chlorophenyl)thiophene

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; tetrabutylammomium bromide; palladium dichloride In 1-methyl-pyrrolidin-2-one at 100℃; Inert atmosphere;100%
With 1,1'-bis-(diphenylphosphino)ferrocene; tetrabutylammomium bromide; palladium dichloride In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere;77%
4-tributylstannanyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester
208465-07-0

4-tributylstannanyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

bromochlorobenzene
106-39-8

bromochlorobenzene

4-(4-Chloro-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester
138647-50-4

4-(4-Chloro-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In toluene at 120℃; for 17h;100%
bromochlorobenzene
106-39-8

bromochlorobenzene

tert-butyl (3aR,6aS)-5-methylene-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate
139228-12-9

tert-butyl (3aR,6aS)-5-methylene-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate

(3aR,6aS)-tert-butyl 5-(4-chlorobenzyl)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

(3aR,6aS)-tert-butyl 5-(4-chlorobenzyl)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

Conditions
ConditionsYield
Stage #1: tert-butyl (3aR,6aS)-5-methylene-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 65℃; for 1h;
Stage #2: bromochlorobenzene With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In tetrahydrofuran; 1,4-dioxane; water at 65℃; for 48h;
100%
bromochlorobenzene
106-39-8

bromochlorobenzene

A

4,4'-dichlorobiphenyl
2050-68-2

4,4'-dichlorobiphenyl

B

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride In 2-pentanol at 100℃; for 57h; Inert atmosphere;A 0.8%
B 99.2%
In 1,2-dimethoxyethane at 85℃; Product distribution; var. solvents; var. times; Ni from NiI2 or NiBr2;
With nickel In 1,2-dimethoxyethane at 85℃; for 20h;A 61 % Chromat.
B 32 % Chromat.
bromochlorobenzene
106-39-8

bromochlorobenzene

allyl bromide
106-95-6

allyl bromide

1-allyl-4-chlorobenzene
1745-18-2

1-allyl-4-chlorobenzene

Conditions
ConditionsYield
Stage #1: bromochlorobenzene With iodine; magnesium In diethyl ether Inert atmosphere; Reflux;
Stage #2: allyl bromide In diethyl ether at 0 - 20℃; for 2.08333h; Inert atmosphere;
99%
(i) Mg, Et2O, (ii) /BRN= 605308/; Multistep reaction;
Stage #1: bromochlorobenzene With iodine; magnesium In diethyl ether for 2h; Reflux; Inert atmosphere;
Stage #2: allyl bromide In diethyl ether at 20℃; Cooling with ice; Inert atmosphere;
bromochlorobenzene
106-39-8

bromochlorobenzene

triethyl phosphite
122-52-1

triethyl phosphite

diethyl (4-chlorophenyl)phosphonate
2373-43-5

diethyl (4-chlorophenyl)phosphonate

Conditions
ConditionsYield
With tri-n-propylamine; tetrabutylammomium bromide; palladium dichloride In water at 100℃; for 4h; Green chemistry; chemoselective reaction;99%
With triethylamine In water at 100℃; for 5h; Green chemistry;92%
With triethylamine In water at 100℃; for 5h; Arbuzov Reaction; Green chemistry;91%
bromochlorobenzene
106-39-8

bromochlorobenzene

acrylic acid n-butyl ester
141-32-2

acrylic acid n-butyl ester

butyl p-chlorocinnamate
123248-22-6, 42175-12-2

butyl p-chlorocinnamate

Conditions
ConditionsYield
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; tetrabutylammomium bromide; triethylamine In N,N-dimethyl-formamide at 140℃; for 20h; Reagent/catalyst; Heck Reaction; Sealed tube; Inert atmosphere; Schlenk technique;99%
With potassium carbonate at 120℃; for 2.25h; Catalytic behavior; Heck Reaction;98%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 3h; Catalytic behavior; Heck Reaction;97%
bromochlorobenzene
106-39-8

bromochlorobenzene

2-(6-bromo-pyridin-2-yl)-4-methylpyrimidine
122918-19-8

2-(6-bromo-pyridin-2-yl)-4-methylpyrimidine

2-[6-(4-chloro-phenyl)-pyridin-2-yl]-4-methyl-pyrimidine

2-[6-(4-chloro-phenyl)-pyridin-2-yl]-4-methyl-pyrimidine

Conditions
ConditionsYield
Stage #1: bromochlorobenzene With n-butyllithium In tetrahydrofuran Dehalogenation;
Stage #2: With zinc(II) chloride In diethyl ether at 20℃; Metallation;
Stage #3: 2-(6-bromo-pyridin-2-yl)-4-methylpyrimidine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; diethyl ether for 2h; Substitution; Heating;
99%
styrene
292638-84-7

styrene

bromochlorobenzene
106-39-8

bromochlorobenzene

A

(E)-1-(4-chlorophenyl)-2-phenylethene
1657-50-7

(E)-1-(4-chlorophenyl)-2-phenylethene

B

1-(4-chlorophenyl)-1-phenylethene
18218-20-7

1-(4-chlorophenyl)-1-phenylethene

Conditions
ConditionsYield
With sodium carbonate; Pd-montmorillonite In 1-methyl-pyrrolidin-2-one at 150℃; for 2h; Heck reaction;A 99%
B n/a
With 1-methyl-pyrrolidin-2-one; sodium acetate; palladium diacetate at 135℃; for 15h; Heck reaction;
With sodium acetate; PdCl2[2-[(1-MeS-S)-3-[(Ph2P-P)oxy]propyl]-N,N-Me2-aniline] In N,N-dimethyl-formamide at 130℃; for 24h; Heck reaction; Title compound not separated from byproducts;
With tetrabutyl-ammonium chloride; sodium carbonate; Pd-MCM-41 In 1-methyl-pyrrolidin-2-one at 150℃; for 6h; Heck coupling; Title compound not separated from byproducts;
bromochlorobenzene
106-39-8

bromochlorobenzene

sodium tetraphenyl borate
143-66-8

sodium tetraphenyl borate

4'-biphenyl chloride
2051-62-9

4'-biphenyl chloride

Conditions
ConditionsYield
With potassium carbonate In water at 50℃; for 0.333333h; Suzuki Coupling;99%
With sodium carbonate at 80℃; for 0.333333h; Green chemistry;98%
With potassium carbonate at 100℃; for 1h; Catalytic behavior;97%
1H-imidazole
288-32-4

1H-imidazole

bromochlorobenzene
106-39-8

bromochlorobenzene

1-(4-chlorophenyl)imidazole
51581-54-5

1-(4-chlorophenyl)imidazole

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; heptakis(6-amino-6-deoxy)-β-cyclodextrin In dimethyl sulfoxide at 110℃; for 24h; Sealed tube;99%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 8h; chemoselective reaction;98%
With copper(I) oxide; potassium phosphate; N1,N2-bis(furan-2-ylmethyl)oxalamide In dimethyl sulfoxide at 120℃; for 24h;97%
bromochlorobenzene
106-39-8

bromochlorobenzene

ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

4'-chloro-2-nitrobiphenyl
6271-80-3

4'-chloro-2-nitrobiphenyl

Conditions
ConditionsYield
Stage #1: ortho-nitrobenzoic acid With potassium carbonate In various solvent(s) at 120℃; for 0.5h;
Stage #2: bromochlorobenzene With 1,10-Phenanthroline; copper(l) iodide In various solvent(s) at 160℃; for 24h; Further stages.;
99%
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N,N-dimethyl-aniline; silver carbonate; palladium dichloride at 150℃; for 2h;35%
Stage #1: ortho-nitrobenzoic acid; copper(II) carbonate In 1-methyl-pyrrolidin-2-one
Stage #2: bromochlorobenzene; bis(acetylacetonato)palladium(II); triphenylphosphine In 1-methyl-pyrrolidin-2-one at 120℃; for 24h; Product distribution / selectivity;
9 %Chromat.
bromochlorobenzene
106-39-8

bromochlorobenzene

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

4-chloro-4'-methylbiphenyl
19482-11-2

4-chloro-4'-methylbiphenyl

Conditions
ConditionsYield
With 2C60H80NaO12*Cl6Pd2; potassium carbonate In methanol; water at 20℃; for 0.166667h; Suzuki coupling;99%
With sodium hydroxide In ethanol; water at 25℃; for 4.5h; Suzuki Coupling;98%
With sodium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 10h; Suzuki-Miyaura Coupling; Inert atmosphere;98%
bromochlorobenzene
106-39-8

bromochlorobenzene

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

A

methyl 3-(4-chlorophenyl)propenoate
20754-21-6

methyl 3-(4-chlorophenyl)propenoate

B

methyl 2-(4-chlorophenyl)acrylate
50415-59-3

methyl 2-(4-chlorophenyl)acrylate

Conditions
ConditionsYield
With sodium carbonate; Pd-montmorillonite In 1-methyl-pyrrolidin-2-one at 150℃; for 2h; Heck reaction;A 99%
B n/a
bromochlorobenzene
106-39-8

bromochlorobenzene

potassium 4-tolyltriolborate

potassium 4-tolyltriolborate

4-chloro-4'-methylbiphenyl
19482-11-2

4-chloro-4'-methylbiphenyl

Conditions
ConditionsYield
palladium diacetate In water; N,N-dimethyl-formamide at 20℃; for 5h;99%
With C24H25Cl3FeN3PPd*C3H6O In ethanol; water at 80℃; for 3h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere; Sealed tube;89%
bromochlorobenzene
106-39-8

bromochlorobenzene

phenol
108-95-2

phenol

4-chlorodiphenyl ether
7005-72-3

4-chlorodiphenyl ether

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 12h;99%
With potassium carbonate In N,N-dimethyl-formamide at 110℃;97%
With copper(l) iodide; iron(III)-acetylacetonate; potassium carbonate In N,N-dimethyl-formamide at 135℃; for 12h; Inert atmosphere;93%
bromochlorobenzene
106-39-8

bromochlorobenzene

C17H20N2O4S
1207202-14-9

C17H20N2O4S

1-[1-(4-chlorophenyl)-2-methoxyvinyl]-4-methoxybenzene
1207201-99-7

1-[1-(4-chlorophenyl)-2-methoxyvinyl]-4-methoxybenzene

Conditions
ConditionsYield
Stage #1: C17H20N2O4S With tris(dibenzylideneacetone)dipalladium (0); lithium tert-butoxide; XPhos In 1,4-dioxane for 0.0166667h; Inert atmosphere;
Stage #2: bromochlorobenzene In 1,4-dioxane at 90℃; for 14h; Inert atmosphere;
99%
bromochlorobenzene
106-39-8

bromochlorobenzene

thiophenol
108-98-5

thiophenol

1,4-bis(phenylthio)benzene
3459-94-7

1,4-bis(phenylthio)benzene

Conditions
ConditionsYield
With 1,2,3,4-tetrahydroquinolin-8-ol; caesium carbonate; copper(I) bromide In N,N-dimethyl-formamide at 130℃; for 48h; Inert atmosphere; chemoselective reaction;99%
bromochlorobenzene
106-39-8

bromochlorobenzene

benzaldehyde
100-52-7

benzaldehyde

(S)-4-chlorobenzhydrol
101402-04-4

(S)-4-chlorobenzhydrol

Conditions
ConditionsYield
With triisopropoxytitanium(IV) chloride; phenyllithium In diethyl ether; cyclohexane at -78 - 20℃; for 0.25h; Inert atmosphere; enantioselective reaction;99%
Stage #1: bromochlorobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: With titanium(IV) isopropylate; magnesium bromide In tetrahydrofuran; diethyl ether; hexane for 0.5h; Inert atmosphere;
Stage #3: benzaldehyde With titanium(IV) isopropylate; (R)-3-(3,5-diphenylphenyl)-2,2'-dihydroxy-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl In diethyl ether; dichloromethane at 0℃; for 3h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
80%
Multi-step reaction with 2 steps
1.1: C36H31F2N2(1+)*BF4(1-); copper(l) chloride; sodium trimethylsilanolate / toluene / 0.42 h / 25 °C / Inert atmosphere; Sealed tube
1.2: 3 h / 60 °C / Inert atmosphere; Sealed tube
2.1: tetrabutyl ammonium fluoride / Inert atmosphere
View Scheme
benzoxazole
273-53-0

benzoxazole

bromochlorobenzene
106-39-8

bromochlorobenzene

2-(4-chlorophenyl)benzoxazole
1141-35-1

2-(4-chlorophenyl)benzoxazole

Conditions
ConditionsYield
With palladium diacetate; sodium t-butanolate; nixantphos In N,N-dimethyl-formamide at 24℃; for 12h; Heck Reaction; Inert atmosphere;99%
With [(N,N'-bis-(2,6-di(isopropyl)phenyl)imidazolidin-2-ylidene)Pd(allyl)]2(μ2-trans-4,4'-bipyridylethylene)(BF4)2; lithium tert-butoxide In 1,2-dimethoxyethane at 10℃; for 12h; Catalytic behavior; Reagent/catalyst; Sealed tube;94%
With palladium diacetate; copper(II) acetate monohydrate; potassium carbonate; triphenylphosphine In toluene for 3h; Reflux; under air;87%
With n-butyllithium; palladium diacetate; C45H35P2(1+)*CF3O3S(1-); caesium carbonate In dimethyl sulfoxide at 50℃; for 14h; Inert atmosphere;85%
bromochlorobenzene
106-39-8

bromochlorobenzene

ethanolamine
141-43-5

ethanolamine

2-(4-chlorophenylamino)ethanol
2933-81-5

2-(4-chlorophenylamino)ethanol

Conditions
ConditionsYield
With copper(l) chloride; potassium hydroxide at 90℃; for 8h; Neat (no solvent);99%
bromochlorobenzene
106-39-8

bromochlorobenzene

benzaldehyde
100-52-7

benzaldehyde

4-chlorobenzophenone
134-85-0

4-chlorobenzophenone

Conditions
ConditionsYield
With palladium diacetate; N-picolinoylcyclohexylamine; potassium hydrogencarbonate In tert-Amyl alcohol at 150℃; for 24h;99%
bromochlorobenzene
106-39-8

bromochlorobenzene

3-(methylsulphinyl)thiophene
133361-97-4

3-(methylsulphinyl)thiophene

2,5-bis(4-chlorophenyl)-3-(methylsulfinyl)thiophene

2,5-bis(4-chlorophenyl)-3-(methylsulfinyl)thiophene

Conditions
ConditionsYield
With di(1-adamantyl)-n-butylphosphine; cesium acetate; bis(dibenzylideneacetone)-palladium(0) at 100℃; for 12h; Inert atmosphere; regioselective reaction;99%
bromochlorobenzene
106-39-8

bromochlorobenzene

4,5-dimethyl-9-phenyl-9H-fluoren-9-ol

4,5-dimethyl-9-phenyl-9H-fluoren-9-ol

C27H21ClO

C27H21ClO

Conditions
ConditionsYield
With chloro(2’-amino-1,1’-biphenyl-2-yl)palladium(II) dimer; C60H54NO5P; sodium hydride In toluene at 80℃; for 12h; Inert atmosphere; enantioselective reaction;99%

106-39-8Relevant articles and documents

-

Derbyshire,Waters

, p. 573,576 (1950)

-

Eco-compatible zeolite-catalysed continuous halogenation of aromatics

Losch,Kolb,Astafan,Daou,Pinard,Pale,Louis

, p. 4714 - 4724 (2016)

A completely eco-compatible halogenation reaction of arenes has been developed allowing high conversions (>95%) of iodobenzene with nearly 100 kg iodobenzene converted per kgcat in one day. Several solid acids, zeolites being the most promising, have been successfully tested in the chlorination reaction of iodobenzene by using trichloroisocyanuric acid (TCCA), a green chlorination agent. H-?BEA zeolites were found to be the most active catalysts for this model halogenation reaction. A strong structure-activity relationship could be established by thorough characterisation (SEM, BET, XRD, FTIR) of various synthetic zeolites. Indeed, nano-sized ?BEA zeolites and more specifically nanosponge-like ?BEA crystals exhibited the highest catalytic performance with a conversion up to 100% and a selectivity toward monochlorinated products up to 98%. Finally, the gained knowledge was applied to set-up an eco-compatible continuous flow halogenation process of different aromatics catalysed by H-?BEA zeolites.

Highly para-Selective Mono-Chlorination of Aromatic Compounds Under Mild Conditions by t-Butyl Hypochlorite in the Presence of Zeolites

Smith, Keith,Butters, Michael,Nay, Barry

, p. 1157 - 1158 (1985)

t-Butyl hypochlorite supported on H(1+), Na(1+) faujasite X (zeolite X) produces para-selective monochlorination of alkyl-, phenyl-, and halobenzenes under mild conditions; for example, chlorobenzene in acetonitrile (at 40 deg C) is chlorinated in high yield of isolated product (92percent) to give dichlorobenzene with an isomer ratio 97percent para/3percent ortho.

-

Gokel et al.

, p. 1633 (1977)

-

Decarboxylative Ipso Halogenation of Mercury(II) Pyridinecarboxylates. Facile Formation of 3-Iodo- and 3-Bromopyridines

Uemura, Sakae,Tanaka, Sakuya,Okano, Masaya,Hamana, Masatomo

, p. 3297 - 3301 (1983)

Treatment of mercury(II) nicotinate with iodine and bromine in nitrobenzene at 180-185 deg C for 2 h afforded 3-iodo- and 3-bromopyridines in 44percent and 27percent yields, respectively, without any regioisomers and dihalopyridines.From mercury(II) picolinate only 2-3percent of 2-bromopyridine was obtained under similar reaction conditions, while the reaction using mercury(II) isonicotinate did not give any products.When a mixture of nicotinic acid and HgO was used in place of mercury(II) nicotinate, the halodecarboxylation occurred with similar ease.An ionic pathway involving the initial attack of electrophilic Hg(II) species on the ring-C bearing carboxyl group to afford a 3-pyridylmercury(II) compound and the subsequent replacement of the Hg(II) moiety by electrophilic iodine and bromine was proposed for this reaction.

The graphite-catalyzed: ipso -functionalization of arylboronic acids in an aqueous medium: metal-free access to phenols, anilines, nitroarenes, and haloarenes

Badgoti, Ranveer Singh,Dandia, Anshu,Parewa, Vijay,Rathore, Kuldeep S.,Saini, Pratibha,Sharma, Ruchi

, p. 18040 - 18049 (2021/05/29)

An efficient, metal-free, and sustainable strategy has been described for the ipso-functionalization of phenylboronic acids using air as an oxidant in an aqueous medium. A range of carbon materials has been tested as carbocatalysts. To our surprise, graphite was found to be the best catalyst in terms of the turnover frequency. A broad range of valuable substituted aromatic compounds, i.e., phenols, anilines, nitroarenes, and haloarenes, has been prepared via the functionalization of the C-B bond into C-N, C-O, and many other C-X bonds. The vital role of the aromatic π-conjugation system of graphite in this protocol has been established and was observed via numerous analytic techniques. The heterogeneous nature of graphite facilitates the high recyclability of the carbocatalyst. This effective and easy system provides a multipurpose approach for the production of valuable substituted aromatic compounds without using any metals, ligands, bases, or harsh oxidants.

Metal- and base-free synthesis of aryl bromides from arylhydrazines

Phuc Tran, Dat,Nomoto, Akihiro,Mita, Soichiro,Dong, Chun-ping,Kodama, Shintaro,Mizuno, Takumi,Ogawa, Akiya

supporting information, (2020/05/08)

An efficient method was developed to synthesize brominated aromatic compounds from arylhydrazine hydrochlorides by using BBr3 in DMSO/CPME (cyclopentyl methyl ether) under air at 80 °C for 1 h without the use of bases or metal catalysts. In particular, this method could be carried out satisfactorily using electron-withdrawing groups to afford aryl bromides in a moderate to excellent yields.

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