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589-87-7

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589-87-7 Usage

Synthesis methods

Industrial parabromoaniline is as raw material, by diazotization, iodo-synthesis of bromo iodobenzene. Preferred synthesis conditions: firstly 0.02mol parabromoaniline is dissolved in a mass fraction of 20% sulfuric acid medium, then reacts with 0.021molNaNO2 to generate bromophenyl diazonium sulfate at-10℃, and then chloroform and 0.021molKI is added into solution to process iodination reaction, after simple treatment bromo-iodobenzene crude product (which the bromo-iodobenzene HPLC purity 98.4%) is obtained, total yield after purification is 80%, increases by 15% than before improved. The product processes structural characterization by IR and 1HNMR. The improved method can greatly improve the purity of the crude product, this avoids the trouble of going through the column, this method is safe and easy to operate, easy to control the process, cost is lower, it is more suitable for the preparation of 1-Bromo-4-iodobenzene. Unit: Heilongjiang University of Chemistry and Materials Science Author: Guo Jing Bai Xuefeng Lvhong Fei

Uses

Different sources of media describe the Uses of 589-87-7 differently. You can refer to the following data:
1. 1. 1-Bromo-4-iodobenzene is used for organic synthesis. 2. Used as substrate for copper-free Sonogashira coupling reaction in aqueous acetone. 3. For the synthesis of β,β-dibromostyrene.
2. suzuki reaction
3. 1-Bromo-4-iodobenzene has been employed:as reagent for in situ desilylation and coupling of silylated alkynesas starting reagent in the total syntheses of ent-conduramine A and ent-7-deoxypancratistatin (alkaloids)as substrate in copper-free Sonogashira coupling in aqueous acetone in synthesis of β,β,dibromostyrenes

Chemical Properties

white to brown cryst. powder, crystals or needles

General Description

Vapour pressure as a function of temperature for 1-bromo-4-iodobenzene has been studied using a diaphragm manometer and torsion mass-loss effusion.

Check Digit Verification of cas no

The CAS Registry Mumber 589-87-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,8 and 9 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 589-87:
(5*5)+(4*8)+(3*9)+(2*8)+(1*7)=107
107 % 10 = 7
So 589-87-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H4BrI/c7-5-1-3-6(8)4-2-5/h1-4H

589-87-7 Well-known Company Product Price

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  • Alfa Aesar

  • (A13859)  1-Bromo-4-iodobenzene, 98%   

  • 589-87-7

  • 10g

  • 378.0CNY

  • Detail
  • Alfa Aesar

  • (A13859)  1-Bromo-4-iodobenzene, 98%   

  • 589-87-7

  • 50g

  • 1509.0CNY

  • Detail
  • Alfa Aesar

  • (A13859)  1-Bromo-4-iodobenzene, 98%   

  • 589-87-7

  • 250g

  • 6037.0CNY

  • Detail

589-87-7SDS

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 1-Bromo-4-iodobenzene

1.2 Other means of identification

Product number -
Other names 4-bromo-1-iodobenzene

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:589-87-7 SDS

589-87-7Synthetic route

4-bromo-aniline
106-40-1

4-bromo-aniline

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
Stage #1: 4-bromo-aniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h; Inert atmosphere;
Stage #2: With potassium iodide In ethyl acetate for 0.5h;
100%
With sulfuric acid; potassium iodide; sodium nitrite In water at -5 - 60℃; Inert atmosphere;92%
Stage #1: 4-bromo-aniline With sulfuric acid; silica gel; sodium nitrite at 20℃; grinding; Neat (no solvent);
Stage #2: With water at 20℃; grinding; Neat (no solvent);
Stage #3: With potassium iodide at 20℃; for 0.166667h; Sandmeyer reaction; grinding; Neat (no solvent);
87%
4-bromophenyldiazonium nitrate

4-bromophenyldiazonium nitrate

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
With potassium iodide for 24h;100%
4-bromobenzenediazonium tetrafluoroborate
673-40-5

4-bromobenzenediazonium tetrafluoroborate

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
With potassium iodide In water at 25℃; for 0.0833333h; Solvent; Sandmeyer Reaction;99%
With diiodomethane; tetrabutylammonium perchlorate In methanol; N,N-dimethyl-formamide at 20℃; for 3h; Sandmeyer Reaction; Electrochemical reaction;61%
With iodine; potassium iodide In dimethyl sulfoxide at 15℃;
triethyl(4-iodophenyl)germane

triethyl(4-iodophenyl)germane

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 4h;96%
(4-bromophenyl)triethylgermane
23268-74-8

(4-bromophenyl)triethylgermane

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
With N-iodo-succinimide In N,N-dimethyl-formamide at 50℃; for 4h;96%
4-iodobenzenediazonium tetrafluoroborate
1514-50-7

4-iodobenzenediazonium tetrafluoroborate

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
With potassium bromide In acetonitrile at 20℃; for 1h; Sandmeyer Reaction; Inert atmosphere;95%
With N-Bromosuccinimide; tetrabutylammonium perchlorate In methanol; N,N-dimethyl-formamide at 20℃; for 3h; Sandmeyer Reaction; Electrochemical reaction;68%
With (triphenylphosphine)gold(I) chloride; sodium bromide In acetonitrile at 50℃; for 5h; Sandmeyer Reaction;73 %Chromat.
1-(4-Bromophenyl)-3,3-diethyltriazene
52010-62-5

1-(4-Bromophenyl)-3,3-diethyltriazene

methyl iodide
74-88-4

methyl iodide

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
at 110 - 120℃; for 6h;94%
4-Bromophenylboronic acid
5467-74-3

4-Bromophenylboronic acid

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
With sodium nitrite In acetonitrile at 80℃; for 1.5h; Sealed tube;94%
With N-iodo-succinimide In acetonitrile at 81℃; for 6h;88%
With potassium fluoride; iodine In 1,4-dioxane at 80℃; for 1h;86%
potassium 4-bromophenyltrifluoroborate
374564-35-9

potassium 4-bromophenyltrifluoroborate

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
With caesium tribromide In water; N,N-dimethyl-formamide at 80℃; for 5h; chemoselective reaction;94%
With chloroamine-T; sodium iodide In tetrahydrofuran; water at 20℃; for 0.25h;87%
Cyclohexanone oxime
100-64-1

Cyclohexanone oxime

(4-bromophenyl)-λ3-iodanediyl diacetate
41018-52-4

(4-bromophenyl)-λ3-iodanediyl diacetate

A

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

B

acetoxy-1 nitroso-1 cyclohexane
10259-08-2

acetoxy-1 nitroso-1 cyclohexane

Conditions
ConditionsYield
In acetic acid at -15℃; for 0.25h;A n/a
B 94%
4-dibenzofurylboronic acid
100124-06-9

4-dibenzofurylboronic acid

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
94%
bromobenzene
108-86-1

bromobenzene

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; [bis(pyridine)iodine]+ tetrafluoroborate In dichloromethane for 2h; Ambient temperature;90%
With sodium periodate; sulfuric acid; iodine In acetic anhydride; acetic acid at 20℃; for 5h; Iodination;87%
With cerium(III) chloride heptahydrate; dihydrogen peroxide; sodium iodide In water for 12h; Reflux; regioselective reaction;86%
bromobenzene
108-86-1

bromobenzene

A

1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

B

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
With iodine; fluorine In chloroform; trichlorofluoromethane at -20℃; for 0.5h;A 5%
B 90%
With dipotassium peroxodisulfate; iodine In dichloromethane; trifluoroacetic acid at 36 - 38℃; for 44h;A n/a
B 74%
With sulfuric acid; iodine; nitric acid In acetic acid at 80 - 100℃; Product distribution;
p-aminoiodobenzene
540-37-4

p-aminoiodobenzene

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
With tert.-butylnitrite; tetrabutylammomium bromide; copper(I) bromide; 10-camphorsulfonic acid In acetonitrile at 20℃; for 24h; Reagent/catalyst; Time; Solvent;90%
With tert.-butylnitrite; tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(ll) bromide In acetonitrile at 20℃; for 1h;78%
With tert.-butylnitrite; tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(ll) bromide64%
bis-[(trifluoroacetoxy)iodo]benzene
2712-78-9

bis-[(trifluoroacetoxy)iodo]benzene

A

1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

B

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
With bromine In chloroform Ambient temperature;A 10%
B 89%
(4-bromophenyl)-λ3-iodanediyl diacetate
41018-52-4

(4-bromophenyl)-λ3-iodanediyl diacetate

acetone oxime
127-06-0

acetone oxime

A

2-acetoxy-2-nitrosopropane
6931-04-0

2-acetoxy-2-nitrosopropane

B

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
In acetic acid at -15℃; for 0.25h;A 88%
B n/a
1-(4-Bromophenyl)-3,3-diethyltriazene
52010-62-5

1-(4-Bromophenyl)-3,3-diethyltriazene

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
With sulfonic acid resin (H+ form, Bio-Rad AG 50W-12); sodium iodide In acetonitrile at 75℃; for 0.133333h;85%
4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
With N-iodo-succinimide; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; iodine; caesium carbonate In 1,2-dichloro-ethane at 50℃; for 24h; Inert atmosphere; Irradiation; Sealed tube;85%
With 3-iodo-4,4-dimethyloxazolidin-2-one In 1,2-dichloro-ethane for 24h; Concentration; Time; Solvent; Reagent/catalyst; Reflux; Irradiation;51%
Cyclopentanone oxime
1192-28-5

Cyclopentanone oxime

(4-bromophenyl)-λ3-iodanediyl diacetate
41018-52-4

(4-bromophenyl)-λ3-iodanediyl diacetate

A

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

B

1-acetoxy-1-nitrosocyclopentane
10259-07-1

1-acetoxy-1-nitrosocyclopentane

Conditions
ConditionsYield
In acetic acid at -15℃; for 0.25h;A n/a
B 83%
iodobenzene
591-50-4

iodobenzene

A

1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

B

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
With potassium bromide; sodium nitrite In water; trifluoroacetic acid at 20℃; for 2h; Product distribution; under argon, other time, other reagent;A 18%
B 82%
With oxygen; potassium bromide; potassium nitrate In water; trifluoroacetic acid at 20℃; for 8h; Product distribution;A 18%
B 82%
With lead(II,IV) oxide; trifluoroacetic acid; potassium bromide at 20℃; Product distribution;
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
Stage #1: 1.4-dibromobenzene With tert.-butyl lithium In diethyl ether at -78℃; for 0.5h;
Stage #2: With iodine In tetrahydrofuran; diethyl ether at -78 - 20℃; for 4.75h;
82%
Stage #1: 1.4-dibromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Inert atmosphere;
Stage #2: With iodine In tetrahydrofuran; hexane at -78 - 25℃; for 1.5h; Inert atmosphere;
75%
With caesium carbonate; potassium iodide; copper(l) iodide In toluene at 110℃; for 12h;
1-(4-bromophenyl)-2-(pyrrolidin-1-yl)diazene
147227-33-6

1-(4-bromophenyl)-2-(pyrrolidin-1-yl)diazene

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
With iodine In 1,2-dichloro-ethane at 80℃; for 4h;80%
bis(trifluoromethanesulfonyl)amide
82113-65-3

bis(trifluoromethanesulfonyl)amide

4-bromo-aniline
106-40-1

4-bromo-aniline

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
Stage #1: bis(trifluoromethanesulfonyl)amide With tert.-butylnitrite; acetic acid In ethanol Cooling with ice;
Stage #2: 4-bromo-aniline With tetraethylammonium iodide In water at 20℃;
80%
ethyl acetohydroximate
10576-12-2

ethyl acetohydroximate

bis(4-bromophenyl)iodonium triflate
139139-81-4

bis(4-bromophenyl)iodonium triflate

A

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

B

ethyl N-4-bromophenoxyacetimidate
1644570-70-6

ethyl N-4-bromophenoxyacetimidate

Conditions
ConditionsYield
Stage #1: ethyl acetohydroximate With sodium t-butanolate In acetonitrile at 0 - 20℃; for 0.25h;
Stage #2: bis(4-bromophenyl)iodonium triflate In acetonitrile at 20℃; for 0.5h; chemoselective reaction;
A 144 mg
B 78%
ethyl acetohydroximate
10576-12-2

ethyl acetohydroximate

bis(4-bromophenyl)iodonium triflate
139139-81-4

bis(4-bromophenyl)iodonium triflate

acetophenone
98-86-2

acetophenone

A

5-bromo-2-phenylbenzo[b]furan
13141-26-9

5-bromo-2-phenylbenzo[b]furan

B

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
Stage #1: ethyl acetohydroximate With sodium t-butanolate In acetonitrile at 0 - 20℃; for 0.25h;
Stage #2: bis(4-bromophenyl)iodonium triflate In acetonitrile at 20℃; for 0.5h;
Stage #3: acetophenone With hydrogenchloride In water; acetonitrile at 20 - 70℃; for 3.25h; Inert atmosphere; chemoselective reaction;
A 73%
B 147 mg
chloroform
67-66-3

chloroform

4,4'-dibromodiphenyliodonium chloride
53601-22-2

4,4'-dibromodiphenyliodonium chloride

A

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

B

4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; potassium hydroxide at 50℃; for 1h; Carbonylation;A n/a
B 72%
(4-bromophenyl)zinc iodide
148651-39-2

(4-bromophenyl)zinc iodide

A

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

B

4-(4-bromophenyl)bromobenzene
92-86-4

4-(4-bromophenyl)bromobenzene

Conditions
ConditionsYield
Stage #1: (4-bromophenyl)zinc iodide With N-chloro-succinimide; tetrakis(triphenylphosphine) palladium(0) In various solvent(s) at 20℃; for 4h;
Stage #2: With iodine In various solvent(s)
A 36%
B 63%
carbon monoxide
201230-82-2

carbon monoxide

1-bromo-4-iodoxybenzene
79054-62-9

1-bromo-4-iodoxybenzene

A

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

B

4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

C

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
With sodium tetrachloropalladate; sodium carbonate In water at 40℃; for 5h; Yields of byproduct given;A n/a
B 61%
C 15%
C7H6BrN7
93680-30-9

C7H6BrN7

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
With tertamethylammonium iodide; trifluoroacetic acid In acetonitrile at 70 - 80℃;61%
potassium (4-iodophenyl)trifluoroborate

potassium (4-iodophenyl)trifluoroborate

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
With acetic acid; lithium bromide In dimethyl sulfoxide at 100℃; for 8h; Schlenk technique;51%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

methyl 2-(tributylstannanyl)-2-propenoate
124582-37-2

methyl 2-(tributylstannanyl)-2-propenoate

methyl 2-(4-bromophenyl)acrylate

methyl 2-(4-bromophenyl)acrylate

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 20℃; Inert atmosphere;100%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide for 24h; Ambient temperature;92%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

(4-bromophenyl)(trimethylsilyl)acetylene
16116-78-2

(4-bromophenyl)(trimethylsilyl)acetylene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 100℃; for 0.5h; Inert atmosphere;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran Sonogashira Cross-Coupling; Inert atmosphere;100%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine at 0℃; Schlenk technique; Inert atmosphere;99%
carbon monoxide
201230-82-2

carbon monoxide

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

Conditions
ConditionsYield
With amphiphilic resin-supported phosphine-palladium; water; potassium carbonate at 25℃; under 760 Torr; for 12h; hydroxycarbonylation;100%
With water; potassium carbonate In acetonitrile at 100℃; under 3750.38 Torr; for 0.0161111h;93%
With water; palladium diacetate; potassium carbonate at 20℃; under 760.051 Torr; for 6h;91%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

tris-iso-propylsilyl acetylene
89343-06-6

tris-iso-propylsilyl acetylene

(2-(4-bromophenyl)ethynyl)triisopropylsilane
271242-20-7

(2-(4-bromophenyl)ethynyl)triisopropylsilane

Conditions
ConditionsYield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 20℃; for 16h;100%
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran at 20℃; for 16h; Sonogashira Coupling;100%
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran at 20℃; for 16h; Sonogashira Coupling;100%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

1-butyn-4-ol
927-74-2

1-butyn-4-ol

4-(4-bromophenyl)-3-butyn-1-ol
59099-79-5

4-(4-bromophenyl)-3-butyn-1-ol

Conditions
ConditionsYield
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) In dichloromethane at 50℃; Sonogashira reaction;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran for 4h; Inert atmosphere; Reflux;85%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide Schlenk technique;82%
acenaphthene-5-boronic acid
183158-33-0

acenaphthene-5-boronic acid

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

5-(4-bromophenyl)acenaphthene
871320-08-0

5-(4-bromophenyl)acenaphthene

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene for 6h; Heating / reflux;100%
4-bromo-1-ethynylbenzene
766-96-1

4-bromo-1-ethynylbenzene

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

1,2-bis(4-bromophenyl)acetylene
2789-89-1

1,2-bis(4-bromophenyl)acetylene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran Sonogashira Cross-Coupling; Inert atmosphere;100%
With C18H18N2O8PdS2(2-)*2Na(1+)*3H2O; triethylamine In water at 80℃; for 8h; Sonogashira Cross-Coupling;97%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide91%
5,15-bis[3,5-di(tert-butyl)phenyl]-10,20-bis(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)porphyrinato-N(21),N(22),N(23),N(24)zinc(II)
1039027-73-0

5,15-bis[3,5-di(tert-butyl)phenyl]-10,20-bis(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)porphyrinato-N(21),N(22),N(23),N(24)zinc(II)

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

5,15-bis[3,5-di(tert-butyl)phenyl]-10,20-bis(4-bromophenyl)porphyrinato-N(21),N(22),N(23),N(24)zinc(II)
1202170-65-7

5,15-bis[3,5-di(tert-butyl)phenyl]-10,20-bis(4-bromophenyl)porphyrinato-N(21),N(22),N(23),N(24)zinc(II)

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); water; caesium carbonate In toluene Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux;100%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

5,10-bis[3,5-di(tert-butyl)phenyl]-15,20-bis(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)porphyrinato-N(21),N(22),N(23),N(24)zinc(II)
1187734-92-4

5,10-bis[3,5-di(tert-butyl)phenyl]-15,20-bis(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)porphyrinato-N(21),N(22),N(23),N(24)zinc(II)

5,10-bis[3,5-di(tert-butyl)phenyl]-15,20-bis(4-bromophenyl)porphyrinato-N(21),N(22),N(23),N(24)zinc(II)
1202170-64-6

5,10-bis[3,5-di(tert-butyl)phenyl]-15,20-bis(4-bromophenyl)porphyrinato-N(21),N(22),N(23),N(24)zinc(II)

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); water; caesium carbonate In toluene Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux;100%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

4,4'-dibromodiphenyl sulfide
3393-78-0

4,4'-dibromodiphenyl sulfide

Conditions
ConditionsYield
With potassium thioacyanate; cetyltrimethylammonim bromide; potassium hydroxide In water at 135℃; for 7h; Green chemistry;100%
With copper(l) iodide; sodiumsulfide nonahydrate; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 18h; Inert atmosphere; chemoselective reaction;94%
With copper(l) iodide; sodiumsulfide nonahydrate; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 18h; Inert atmosphere; Darkness;94%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

C12H13BrO

C12H13BrO

C18H16Br2O

C18H16Br2O

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran for 16h; Sonogashira Cross-Coupling; Inert atmosphere;100%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

N-(3,3-dimethoxypropyl)hex-5-ynamide

N-(3,3-dimethoxypropyl)hex-5-ynamide

N-(3,3-dimethoxypropyl)-6-(4-bromophenyl)hex-5-ynamide

N-(3,3-dimethoxypropyl)-6-(4-bromophenyl)hex-5-ynamide

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 50℃; for 4h; Sonogashira Cross-Coupling; Inert atmosphere;100%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

(R)-(+)-4-methylpyrrolidin-2-one
260061-31-2

(R)-(+)-4-methylpyrrolidin-2-one

(R)-1-(4-bromophenyl)-4-methylpyrrolidin-2-one

(R)-1-(4-bromophenyl)-4-methylpyrrolidin-2-one

Conditions
ConditionsYield
With copper(l) iodide; cesium fluoride; N,N`-dimethylethylenediamine In ethyl acetate at 50℃; for 16h; Inert atmosphere;100%
4,4-dimethylpyrrolidin-2-one
66899-02-3

4,4-dimethylpyrrolidin-2-one

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

1-(4-bromophenyl)-4,4-dimethylpyrrolidin-2-one

1-(4-bromophenyl)-4,4-dimethylpyrrolidin-2-one

Conditions
ConditionsYield
With copper(l) iodide; cesium fluoride; N,N`-dimethylethylenediamine In ethyl acetate at 50℃; for 16h; Inert atmosphere;100%
(S)-(-)-4-methylpyrrolidin-2-one
31551-66-3

(S)-(-)-4-methylpyrrolidin-2-one

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

(S)-1-(4-bromophenyl)-4-methylpyrrolidin-2-one

(S)-1-(4-bromophenyl)-4-methylpyrrolidin-2-one

Conditions
ConditionsYield
With copper(l) iodide; cesium fluoride; N,N`-dimethylethylenediamine In ethyl acetate at 50℃; for 16h; Inert atmosphere;100%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

5-azaspiro[2.4]heptan-6-one

5-azaspiro[2.4]heptan-6-one

5-(4-bromophenyl)-5-azaspiro[2.4]heptan-6-one

5-(4-bromophenyl)-5-azaspiro[2.4]heptan-6-one

Conditions
ConditionsYield
With copper(l) iodide; cesium fluoride; N,N`-dimethylethylenediamine In ethyl acetate at 50℃; for 16h; Inert atmosphere;100%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

2-(5-(4-(tert-butyl)phenyl)-4-(4-chlorophenyl)-2-(4-fluorophenyl)furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-(5-(4-(tert-butyl)phenyl)-4-(4-chlorophenyl)-2-(4-fluorophenyl)furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

3-(4-bromophenyl)-5-(4-(tert-butyl)phenyl)-4-(4-chlorophenyl)-2-(4-fluorophenyl)furan

3-(4-bromophenyl)-5-(4-(tert-butyl)phenyl)-4-(4-chlorophenyl)-2-(4-fluorophenyl)furan

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium hydroxide In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Schlenk technique;100%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

N-(cyclopropylmethyl)-1,1,1-trifluoromethanesulfonamide
357383-42-7

N-(cyclopropylmethyl)-1,1,1-trifluoromethanesulfonamide

N-((2-(4-bromophenyl)cyclopropyl)methyl)-1,1,1-trifluoromethanesulfonamide

N-((2-(4-bromophenyl)cyclopropyl)methyl)-1,1,1-trifluoromethanesulfonamide

Conditions
ConditionsYield
With t-Boc-L-valine; sodium 2,2,2-trifluoroacetate; palladium diacetate; silver carbonate In tert-butyl alcohol at 80℃; for 18h; Sealed tube; enantioselective reaction;99.9%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

9H-carbazole
86-74-8

9H-carbazole

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In 1,2-dimethoxyethane; water at 95℃; for 20h; Catalytic behavior; Solvent; Schlenk technique; Inert atmosphere; Sealed tube;99%
With copper; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 42h; Inert atmosphere;96%
With copper(I) oxide; 2,2,6,6-tetramethylheptane-3,5-dione; potassium hydroxide In N,N-dimethyl-formamide at 110℃; for 24h; Inert atmosphere; Schlenk technique;95%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

propargyl alcohol
107-19-7

propargyl alcohol

3-(4-bromophenyl)prop-2-yn-1-ol
37614-58-7

3-(4-bromophenyl)prop-2-yn-1-ol

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃;99%
Stage #1: 1,4-bromoiodobenzene With piperidine; copper(l) iodide; dichlorobis(tri-O-tolylphosphine)palladium In toluene at 20℃; for 0.0333333h; Inert atmosphere;
Stage #2: propargyl alcohol In toluene at 35℃; Sonogashira coupling; Inert atmosphere;
98%
With piperidine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In toluene at 60℃; for 2h; Inert atmosphere;95%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

phenylacetylene
536-74-3

phenylacetylene

1-bromo-4-phenylethynylbenzene
13667-12-4

1-bromo-4-phenylethynylbenzene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In acetonitrile at 20℃; for 17h; Inert atmosphere;99%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; triethylamine In acetonitrile at 20℃; Sonogashira Cross-Coupling; Inert atmosphere;99%
With triethylamine In neat (no solvent) at 20℃; for 6h; Sonogashira Cross-Coupling;97%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

C15H25BrOSiZn

C15H25BrOSiZn

(4'-Bromo-biphenyl-4-yloxy)-triisopropyl-silane

(4'-Bromo-biphenyl-4-yloxy)-triisopropyl-silane

Conditions
ConditionsYield
(4-F(13)C6-C6H4)3P; bis(dibenzylideneacetone)-palladium(0) In toluene at 60℃;99%
acrylic acid n-butyl ester
141-32-2

acrylic acid n-butyl ester

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

butyl (E)-4-bromocinnamate
91911-22-7, 131061-14-8

butyl (E)-4-bromocinnamate

Conditions
ConditionsYield
With dichloro bis(acetonitrile) palladium(II); potassium phosphate; N,N'-(1,2-ethanediylidene)bishexahydro-1H-azepin-1-amine In N,N-dimethyl-formamide at 80℃; for 6h; Mizoroki-Heck reaction;99%
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 1h; Heck Reaction;98%
With tributyl-amine In water at 90℃; for 7h; Heck Reaction;95%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

phenylboronic acid
98-80-6

phenylboronic acid

4-bromo-1,1'-biphenyl
92-66-0

4-bromo-1,1'-biphenyl

Conditions
ConditionsYield
With sodium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 6h; Suzuki-Miyaura Coupling; Inert atmosphere;99%
With potassium carbonate In water at 90℃; for 1h; Suzuki-Miyaura coupling; chemoselective reaction;98%
With potassium carbonate In ethanol; water at 80℃; for 0.583333h; Catalytic behavior; Suzuki-Miyaura Coupling;96%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

thiophenol
108-98-5

thiophenol

phenyl(4-bromophenyl)sulfide
65662-88-6

phenyl(4-bromophenyl)sulfide

Conditions
ConditionsYield
With (tris(3,5-dimethyl-1-pyrazolyl)methane)CuI; lithium tert-butoxide In 1,4-dioxane at 110℃; for 24h; Ullmann condensation; Inert atmosphere; chemoselective reaction;99%
With copper(l) iodide; potassium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 16h;96%
With copper(l) iodide; 8-Hydroxyquinoline-N-oxide; caesium carbonate In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere; chemoselective reaction;96%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

hex-1-yne
693-02-7

hex-1-yne

1-bromo-4-(hex-1-yn-1-yl)benzene
190649-11-7

1-bromo-4-(hex-1-yn-1-yl)benzene

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In N,N-dimethyl-formamide at 40℃;99%
With CuI(xantphos); caesium carbonate In N,N-dimethyl-formamide at 135℃; for 0.166667h; Sonogashira type reaction; Inert atmosphere; Microwave irradiation;78%
With copper(I) oxide; caesium carbonate In N,N-dimethyl-formamide at 135℃; for 24h; Sonogashira Cross-Coupling; Inert atmosphere;67%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

phenylboronic acid
98-80-6

phenylboronic acid

[1,1';4',1'']terphenyl
92-94-4

[1,1';4',1'']terphenyl

Conditions
ConditionsYield
With potassium carbonate In water at 50℃; for 1.5h; Suzuki Coupling;99%
With magnesium hydroxide; potassium hydroxide; barium(II) hydroxide; calcium hydroxide In water at 20℃; for 1.5h; Suzuki Coupling;99%
With sodium carbonate; palladium diacetate In water; N,N-dimethyl-formamide at 60℃; for 12h; Suzuki;98%

589-87-7Relevant articles and documents

Acidic ionic liquid supported on silica-coated magnetite nanoparticles as a green catalyst for one-pot diazotization-halogenation of the aromatic amines

Isaad, Jalal

, p. 49333 - 49341 (2014)

Acidic ionic liquid was immobilized on silica-coated magnetite nanoparticles (Fe3O4@SILnP) and used as an efficient heterogeneous catalyst for the diazotization-iodination reaction of different aromatic amines under solvent-free conditions at room temperature. The diazonium salts that are formed by this catalyst are stable at room temperature and react rapidly with sodium iodide to produce aryl iodides in good to excellent yields. This method has some advantages such as low pollution, rapid access to products, simple work-up and easy separation of catalyst from the reaction mixture.

Hydrogen-Bond-Donor Solvents Enable Catalyst-Free (Radio)-Halogenation and Deuteration of Organoborons

Yang, Yi,Gao, Xinyan,Zeng, Xiaojun,Han, Junbin,Xu, Bo

supporting information, p. 1297 - 1300 (2020/12/23)

A hydrogen bond donor solvent assisted (radio)halogenation and deuteration of organoborons has been developed. The reactions exhibited high functional group tolerance and needed only an ambient atmosphere. Most importantly, compared to literature methods, our conditions are more consistent with the principals of green chemistry (e.g., metal-free, strong oxidant-free, more straightforward conditions).

Arene diazonium saccharin intermediates: A greener and cost-effective alternative method for the preparation of aryl iodide

Ghaffari Khaligh, Nader,Rafie Johan, Mohd,Shahnavaz, Zohreh,Zaharani, Lia

, p. 535 - 542 (2020/06/01)

In the current protocol, the arene diazonium saccharin derivatives were initially produced from various substituted aromatic amines; subsequently, these intermediates were treated with a greener organic iodide for the preparation of the aryl iodide. We tried to choose low-cost, commercially available, biodegradable, recoverable, ecofriendly, and safe reagents and solvents. The arene diazonium saccharin intermediates could be stored in the liquid phase into a refrigerator for a long time with no significant loss activity. The outstanding merits of the current protocol (a) included the partial recovering of saccharin and tetraethylammonium salt, (b) reduce the use of solvents and the reaction steps due to eliminating separation and purification of intermediates, (c) good yield of the sterically hindered substrates, and (d) avoid the generation of heavy metal or corrosive waste.

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