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591-18-4

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591-18-4 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 591-18-4 differently. You can refer to the following data:
1. Clear colourless to light yellow liquid
2. Light sensitive. Incompatible with strong oxidizing agents, strong bases and strong acids. Store in a cool place.

Uses

1-Bromo-3-iodobenzene is used in the preparation of 3'-bromo-2,3,4,5,6-pentaethyl-biphenyl by reacting with hex-3-yne. It is also used to prepare 1-(3'-bromophenyl)-3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodec-1-ene and 1-(3'-bromophenyl)-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene. Further, it is involved in the preparation of oxygen-tethered 1,6-enynes.

Check Digit Verification of cas no

The CAS Registry Mumber 591-18-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 1 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 591-18:
(5*5)+(4*9)+(3*1)+(2*1)+(1*8)=74
74 % 10 = 4
So 591-18-4 is a valid CAS Registry Number.
InChI:InChI=1/C6H4BrI/c7-5-2-1-3-6(8)4-5/h1-4H

591-18-4 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (A19596)  1-Bromo-3-iodobenzene, 98%   

  • 591-18-4

  • 25g

  • 505.0CNY

  • Detail
  • Alfa Aesar

  • (A19596)  1-Bromo-3-iodobenzene, 98%   

  • 591-18-4

  • 100g

  • 1799.0CNY

  • Detail

591-18-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Bromo-3-iodobenzene

1.2 Other means of identification

Product number -
Other names m-Bromoiodobenzene

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:591-18-4 SDS

591-18-4Synthetic route

m-bromobenzoic acid
585-76-2

m-bromobenzoic acid

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

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;80%
With 1-iodo-3,5,5-trimethylhydantoin In tetrachloromethane for 15h; Concentration; Reagent/catalyst; Solvent; Time; Reflux; Irradiation;61%
(3-bromophenyl)boronic acid
89598-96-9

(3-bromophenyl)boronic acid

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

Conditions
ConditionsYield
With N-iodo-succinimide In acetonitrile at 81℃; for 6h;77%
carbon monoxide
201230-82-2

carbon monoxide

3-bromo-1-iodylbenzene
150177-91-6

3-bromo-1-iodylbenzene

A

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

B

isophthalic acid
121-91-5

isophthalic acid

C

m-bromobenzoic acid
585-76-2

m-bromobenzoic acid

Conditions
ConditionsYield
With sodium tetrachloropalladate; sodium carbonate In water at 40℃; for 5.5h; Yields of byproduct given;A n/a
B 14%
C 76%
3-bromobenzoyl chloride
1711-09-7

3-bromobenzoyl chloride

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 100℃; for 12h;72%
bromobenzene
108-86-1

bromobenzene

phenol
108-95-2

phenol

A

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

B

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

1-Bromo-2-iodobenzene

C

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
With tert.-butylhydroperoxide; iodine at 289.9℃; for 0.0272222h; Product distribution;A 47.6%
B 28.9%
C 23.5%
3-Iodoaniline
626-01-7

3-Iodoaniline

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

Conditions
ConditionsYield
Ueberfuehrung in das Diazoperbromid und Zersetzung;
3-bromoaniline
591-19-5

3-bromoaniline

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

Conditions
ConditionsYield
With iodine
1-Iod-3-(trimethylsilyl)benzol
63520-49-0

1-Iod-3-(trimethylsilyl)benzol

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

Conditions
ConditionsYield
With bromine
3-iodobenzoyl chloride
1711-10-0

3-iodobenzoyl chloride

A

2-<(trichloromethyl)thio>pyridine
66832-24-4

2-<(trichloromethyl)thio>pyridine

B

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); Bromotrichloromethane; 2-mercaptopyridine-1-oxide sodium salt at 100℃; for 0.0833333h; Heating; Yield given. Yields of byproduct given;
sodium phenoxide
139-02-6

sodium phenoxide

m-bromodiphenyliodonium iodide
81447-71-4

m-bromodiphenyliodonium iodide

A

bromobenzene
108-86-1

bromobenzene

B

diphenylether
101-84-8

diphenylether

C

iodobenzene
591-50-4

iodobenzene

D

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

E

3-bromodiphenyl ether
6876-00-2

3-bromodiphenyl ether

F

benzene
71-43-2

benzene

Conditions
ConditionsYield
In water at 60℃; Product distribution; Mechanism; relative rates of decomposition of the 9-I-2 intermediate;
bis-(3-bromo-benzoyl)-peroxide
1829-88-5

bis-(3-bromo-benzoyl)-peroxide

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

Conditions
ConditionsYield
With iodobenzene In benzene
1,3-dibromobenzene
108-36-1

1,3-dibromobenzene

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

Conditions
ConditionsYield
With Iodine monochloride; N-ethyl-N,N-diisopropylamine; Wang resin 1.) DMF, 40-50 deg C, 2.) CH2Cl2; Yield given. Multistep reaction;
iodine
7553-56-2

iodine

3-bromo-benzenediazonium; bromide
63467-81-2

3-bromo-benzenediazonium; bromide

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

iodine
7553-56-2

iodine

3-bromo-benzenediazonium; dichloride iodide

3-bromo-benzenediazonium; dichloride iodide

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

iodine
7553-56-2

iodine

m-bromobenzene diazonium nitrate

m-bromobenzene diazonium nitrate

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

iodine
7553-56-2

iodine

3-bromo-benzenediazonium; hexachloroplatinate (IV)

3-bromo-benzenediazonium; hexachloroplatinate (IV)

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

iodine
7553-56-2

iodine

3-bromophenyldiazonium chloride
20893-74-7

3-bromophenyldiazonium chloride

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

3-bromo-benzenediazonium; tribromoide

3-bromo-benzenediazonium; tribromoide

iodine

iodine

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

3-bromo-benzenediazonium; sulfate

3-bromo-benzenediazonium; sulfate

iodine

iodine

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

diethyl ether
60-29-7

diethyl ether

3-bromo-phenyl magnesium (1+); bromide

3-bromo-phenyl magnesium (1+); bromide

iodine

iodine

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

m-bis(trimethylsilyl)benzene
2060-89-1

m-bis(trimethylsilyl)benzene

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: IBr
2: Br2
View Scheme
4-Methyl-1-pentene
691-37-2

4-Methyl-1-pentene

bis(3-bromophenyl)iodonium triflate
1426083-16-0

bis(3-bromophenyl)iodonium triflate

A

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

B

6-bromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene
176088-47-4

6-bromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene

Conditions
ConditionsYield
With copper(I) trifluoromethanesolfonate toluene complex In dichloromethane at 70℃; for 24h; Molecular sieve; Inert atmosphere; Sealed tube;A n/a
B 82 %Spectr.
3-bromobenzoyl chloride
1711-09-7

3-bromobenzoyl chloride

1-iodo-4-n-propylbenzene
126261-84-5

1-iodo-4-n-propylbenzene

A

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

B

4-propylbenzoyl chloride
52710-27-7

4-propylbenzoyl chloride

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 100℃; for 12h; Time;
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

2-(3-bromophenyl)ethynyltrimethylsilane
3989-13-7

2-(3-bromophenyl)ethynyltrimethylsilane

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; trimethylamine for 0.5h; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique; Reflux;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In acetonitrile at 20℃; for 1h; Inert atmosphere;99%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;93%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

3-(3'-bromophenyl)pyridine
4422-32-6

3-(3'-bromophenyl)pyridine

Conditions
ConditionsYield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 100℃; Inert atmosphere;100%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 18h; Reflux;90.9%
With palladium diacetate; sodium carbonate; triphenylphosphine In 1,2-dimethoxyethane; water for 18h; Inert atmosphere; Reflux;88%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

ethyl 1-(2,5-difluorophenyl)-5-({3-[(2-ethylhexyl)oxy]-3-oxopropyl}thio)-1H-pyrazole-3-carboxylate
1138037-06-5

ethyl 1-(2,5-difluorophenyl)-5-({3-[(2-ethylhexyl)oxy]-3-oxopropyl}thio)-1H-pyrazole-3-carboxylate

ethyl 5-[(3-bromophenyl)thio]-1-(2,5-difluorophenyl)-1H-pyrazole-3-carboxylate
1138037-34-9

ethyl 5-[(3-bromophenyl)thio]-1-(2,5-difluorophenyl)-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: ethyl 1-(2,5-difluorophenyl)-5-({3-[(2-ethylhexyl)oxy]-3-oxopropyl}thio)-1H-pyrazole-3-carboxylate With sodium ethanolate In ethanol at 0 - 20℃;
Stage #2: 1-Bromo-3-iodobenzene; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 80℃; for 2h;
100%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

3,3’-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)dipyridine

3,3’-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)dipyridine

3,3'-(3'-bromobiphenyl-3,5-diyl)dipyridine
1258975-28-8

3,3'-(3'-bromobiphenyl-3,5-diyl)dipyridine

Conditions
ConditionsYield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 100℃; Inert atmosphere;100%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

carbon monoxide
201230-82-2

carbon monoxide

aniline
62-53-3

aniline

3-bromo-N-phenylbenzamide
63710-33-8

3-bromo-N-phenylbenzamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 100℃; under 750.075 Torr; for 8h; Schlenk technique; Inert atmosphere;100%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

2-methyl-4-(3-bromophenyl)-3-butyn-2-ol

2-methyl-4-(3-bromophenyl)-3-butyn-2-ol

Conditions
ConditionsYield
With piperidine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Schlenk technique;100%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In N,N-dimethyl-formamide at 130℃; for 1h; Microwave irradiation;
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

[(3-cyanopropyl)diisopropylsilyl]acetylene
1057407-31-4

[(3-cyanopropyl)diisopropylsilyl]acetylene

4-{[(3-bromophenyl)ethynyl]diisopropylsilyl}butanenitrile

4-{[(3-bromophenyl)ethynyl]diisopropylsilyl}butanenitrile

Conditions
ConditionsYield
With piperidine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique;100%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

1,4-bis(3-ethynylphenyl)-8,8-dimethoxy-4,4a,5,7a-tetrahydro-1H-1,4-methanocyclopenta[d]pyridazine

1,4-bis(3-ethynylphenyl)-8,8-dimethoxy-4,4a,5,7a-tetrahydro-1H-1,4-methanocyclopenta[d]pyridazine

1,4-bis(3-((3-bromophenyl)ethynyl)phenyl)-8,8-dimethoxy-4,4a,5,7a-tetrahydro-1H-1,4-methanocyclopenta[d]pyridazine

1,4-bis(3-((3-bromophenyl)ethynyl)phenyl)-8,8-dimethoxy-4,4a,5,7a-tetrahydro-1H-1,4-methanocyclopenta[d]pyridazine

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 70℃; for 10h; Inert atmosphere;100%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

dimethyl (3-bromophenyl)phosphonate
15104-42-4

dimethyl (3-bromophenyl)phosphonate

Conditions
ConditionsYield
With palladium diacetate at 90℃; Sealed tube;99.8%
With palladium diacetate at 90℃; Sealed tube;99.8%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

phenylacetylene
536-74-3

phenylacetylene

1-phenyl-2-(m-bromo)phenylacetylene
29778-29-8

1-phenyl-2-(m-bromo)phenylacetylene

Conditions
ConditionsYield
With palladium on activated charcoal; choline chloride; triethylamine; glycerol at 60℃; for 3h; Sonogashira Cross-Coupling;99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 18h; Inert atmosphere;98%
With triethylamine In neat (no solvent) at 20℃; for 6h; Sonogashira Cross-Coupling;96%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

1,2-bis(3-bromophenyl)acetylene
153404-60-5

1,2-bis(3-bromophenyl)acetylene

Conditions
ConditionsYield
With copper(l) iodide; water; 1,8-diazabicyclo[5.4.0]undec-7-ene; bis-triphenylphosphine-palladium(II) chloride In benzene at 20℃; for 18h; Product distribution; Further Variations:; Catalysts; Reaction partners; Reagents; Solvents; temperature dependence; Sonogashira reaction;99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran; water at 20℃; for 16h; Sonogashira coupling;81%
Stage #1: 1-Bromo-3-iodobenzene; trimethylsilylacetylene With potassium carbonate In methanol; acetonitrile at 40℃; Sonogashira Cross-Coupling;
Stage #2: 1-Bromo-3-iodobenzene In methanol; acetonitrile at 40℃; Sonogashira Cross-Coupling; chemoselective reaction;
76%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; water; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 20℃; for 18h; Inert atmosphere; Schlenk technique; Darkness;
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

ethyl acrylate
140-88-5

ethyl acrylate

ethyl (2E)-3-(3-bromophenyl)prop-2-enoate
59114-88-4

ethyl (2E)-3-(3-bromophenyl)prop-2-enoate

Conditions
ConditionsYield
With sodium acetate; aluminum oxide; ruthenium In N,N-dimethyl-formamide at 115℃; for 12h; Heck-type olefination;99%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

tris-iso-propylsilyl acetylene
89343-06-6

tris-iso-propylsilyl acetylene

1-bromo-3-[(triisopropylsilyl)ethynyl]benzene

1-bromo-3-[(triisopropylsilyl)ethynyl]benzene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 40℃; for 17h;99%
With diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran at 20℃; for 24h; Sonogashira coupling;87%
With copper; palladium; triethylamine In tetrahydrofuran Sonogashira coupling;80%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

m-bromoiodobenzene dichloride
936252-06-1

m-bromoiodobenzene dichloride

Conditions
ConditionsYield
With hydrogenchloride; sodium hypochlorite at 15℃; for 0.666667h;99%
With hydrogenchloride; ammonium cerium (IV) nitrate In water; acetic acid at 20℃; for 1h;88%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

3-bromoaniline
591-19-5

3-bromoaniline

Conditions
ConditionsYield
With copper(l) iodide; ascorbic acid In ammonia at 25℃; for 18h; liquid NH3;99%
With copper(I) oxide; ammonium hydroxide; C17H14N2O3; potassium hydroxide In ethanol at 60℃; for 24h; Schlenk technique; Inert atmosphere;93%
With iron(III) oxide; sodium hydroxide; copper(l) iodide; ammonia In ethanol; water at 90℃; for 16h;89%
With acetamidine hydrochloride; caesium carbonate In N,N-dimethyl-formamide at 130℃; for 20h; Inert atmosphere; Green chemistry;72%
trifluorormethanesulfonic acid
1493-13-6

trifluorormethanesulfonic acid

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

3'-bromo-2,4,6-trimethyl(diphenyliodonium) trifluoromethanesulfonate
1203709-76-5

3'-bromo-2,4,6-trimethyl(diphenyliodonium) trifluoromethanesulfonate

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 2h;99%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 2.08333h;55%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 2h;55%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

thiophenol
108-98-5

thiophenol

1,3-bis(phenylthio)benzene
2974-10-9

1,3-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%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

2,2-dimethyl-N-(prop-2-ynyl)propionamide
178320-73-5

2,2-dimethyl-N-(prop-2-ynyl)propionamide

N-(3-(3-bromophenyl)prop-2-ynyl)pivalamide

N-(3-(3-bromophenyl)prop-2-ynyl)pivalamide

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine at 20℃; for 0.5h; Inert atmosphere;99%
N-acetylcystein
616-91-1

N-acetylcystein

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

(R)-2-acetamido-3-((3-bromophenyl)thio)propanoic acid
113276-93-0

(R)-2-acetamido-3-((3-bromophenyl)thio)propanoic acid

Conditions
ConditionsYield
Stage #1: N-acetylcystein; 1-Bromo-3-iodobenzene With C53H46NO4PPdS In tetrahydrofuran at 20℃; for 0.0166667h; Schlenk technique;
Stage #2: With triethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere; chemoselective reaction;
99%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

3-(benzofuran-2-yl)-1,1,1,3,5,5,5-heptamethyltrisiloxane
1583285-91-9

3-(benzofuran-2-yl)-1,1,1,3,5,5,5-heptamethyltrisiloxane

2-(3’-bromophenyl)benzofuran

2-(3’-bromophenyl)benzofuran

Conditions
ConditionsYield
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; potassium hydroxide In para-xylene at 20 - 50℃; for 13h; Inert atmosphere; Schlenk technique; Glovebox;99%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

Dichlorophenylphosphine
644-97-3

Dichlorophenylphosphine

bis(3-bromophenyl)(phenyl)phosphine oxide

bis(3-bromophenyl)(phenyl)phosphine oxide

Conditions
ConditionsYield
Stage #1: 1-Bromo-3-iodobenzene With isopropylmagnesium chloride In tetrahydrofuran at -40 - -20℃; for 2h;
Stage #2: Dichlorophenylphosphine In tetrahydrofuran at 20℃; for 2h;
Stage #3: With dihydrogen peroxide at 20℃; for 0.5h;
99%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

phenylboronic acid
98-80-6

phenylboronic acid

1,3-diphenylbenzene
92-06-8

1,3-diphenylbenzene

Conditions
ConditionsYield
With sodium carbonate; palladium diacetate In water; N,N-dimethyl-formamide at 60℃; for 12h; Suzuki;98%
With potassium carbonate In water; acetone at 60℃; for 24h; Suzuki coupling;98%
With sodium carbonate In water; N,N-dimethyl-formamide at 90℃; for 2h; Suzuki cross-coupling reaction;84%
With palladium; potassium carbonate In methanol; acetonitrile at 20℃; for 3.5h; Suzuki Coupling;81%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

phenylboronic acid
98-80-6

phenylboronic acid

3-bromobiphenyl
2113-57-7

3-bromobiphenyl

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; triphenylphosphine In water; toluene at 100℃; for 24h;98%
With barium dihydroxide; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water for 6h; Suzuki coupling; Heating;92%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water for 8h; Inert atmosphere; Reflux;80%
4-dibenzofurylboronic acid
100124-06-9

4-dibenzofurylboronic acid

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

1-bromo-3-(4-dibenzofuranyl)benzene
887944-90-3

1-bromo-3-(4-dibenzofuranyl)benzene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 4h; Reflux; Inert atmosphere;98%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In toluene at 90℃; for 2 - 3h;87%
Stage #1: 4-dibenzofurylboronic acid; 1-Bromo-3-iodobenzene With potassium carbonate In ethanol; water; toluene at 20℃; for 0.5h; Inert atmosphere;
Stage #2: With palladium diacetate; tris-(o-tolyl)phosphine In ethanol; water; toluene for 2h; Reflux; Inert atmosphere;
78.8%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

9H-carbazole
86-74-8

9H-carbazole

9-(3-bromophenyl)carbazole
185112-61-2

9-(3-bromophenyl)carbazole

Conditions
ConditionsYield
With copper; potassium carbonate In N,N-dimethyl-formamide at 130℃;98%
With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine In toluene for 4h;96%
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 110℃;90%
iodobenzene
591-50-4

iodobenzene

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

3-bromobenzophenone
1016-77-9

3-bromobenzophenone

Conditions
ConditionsYield
Stage #1: iodobenzene With gallium; aluminium at 120℃; for 20h; Inert atmosphere;
Stage #2: 1-Bromo-3-iodobenzene In toluene at 20℃; for 3h;
98%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

diphenyl diselenide
1666-13-3

diphenyl diselenide

3-bromophenyl phenyl selenide
856074-00-5

3-bromophenyl phenyl selenide

Conditions
ConditionsYield
With copper(II) sulfide; iron; potassium carbonate In dimethyl sulfoxide at 110℃; for 3h; Inert atmosphere; chemoselective reaction;98%
With tetrabutylammomium bromide; potassium hydroxide In water at 100℃; for 9h; chemoselective reaction;88%
With magnesium In N,N-dimethyl-formamide at 110℃; for 30h; Inert atmosphere; Schlenk technique; Green chemistry;78%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

ethyl iodide
75-03-6

ethyl iodide

1-bromo-2-ethyl-3-iodobenzene
1344998-09-9

1-bromo-2-ethyl-3-iodobenzene

Conditions
ConditionsYield
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 3h; Inert atmosphere;98%
With lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - -50℃; for 4h; Inert atmosphere;
With lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - -50℃; for 4h; Inert atmosphere;
2-aminobutanol
96-20-8, 13054-87-0

2-aminobutanol

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

2-(3-bromophenylamino)-1-butanol
1184497-56-0

2-(3-bromophenylamino)-1-butanol

Conditions
ConditionsYield
With copper(l) chloride; potassium hydroxide at 20℃; for 8h; Neat (no solvent);98%
With copper(l) iodide; potassium hydroxide In water at 100℃; for 12h; Sealed tube;92%
trimethyl(prop-1-ynyl)silane
6224-91-5

trimethyl(prop-1-ynyl)silane

1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

1-bromo-3-(prop-1-yn-1-yl)benzene
66952-36-1

1-bromo-3-(prop-1-yn-1-yl)benzene

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrabutyl ammonium fluoride; triethylamine In tetrahydrofuran; toluene at 20℃; for 17h; Schlenk technique; Inert atmosphere;98%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrafluoroammonium fluoride; triethylamine In tetrahydrofuran; toluene at 20℃; for 17h; Inert atmosphere;86%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrafluoroammonium fluoride; triethylamine In tetrahydrofuran; toluene at 20℃; for 17h; Inert atmosphere;86%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrafluoroammonium fluoride; triethylamine In tetrahydrofuran; toluene at 20℃; for 17h; Inert atmosphere;86%
With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrabutyl ammonium fluoride In tetrahydrofuran; toluene at 20℃; Inert atmosphere;80%

591-18-4Relevant articles and documents

Metathesis-active ligands enable a catalytic functional group metathesis between aroyl chlorides and aryl iodides

Lee, Yong Ho,Morandi, Bill

, p. 1016 - 1022 (2018/09/06)

Current methods for functional group interconversion have, for the most part, relied on relatively strong driving forces which often require highly reactive reagents to generate irreversibly a desired product in high yield and selectivity. These approaches generally prevent the use of the same catalytic strategy to perform the reverse reaction. Here we describe a catalytic functional group metathesis approach to interconvert, under CO-free conditions, two synthetically important classes of electrophiles that are often employed in the preparation of pharmaceuticals and agrochemicals—aroyl chlorides (ArCOCl) and aryl iodides (ArI). Our reaction design relies on the implementation of a key reversible ligand C–P bond cleavage event, which enables a non-innocent, metathesis-active phosphine ligand to mediate a rapid aryl group transfer between the two different electrophiles. Beyond enabling a practical and safer approach to the interconversion of ArCOCl and ArI, this type of ligand non-innocence provides a blueprint for the development of a broad range of functional group metathesis reactions employing synthetically relevant aryl electrophiles.

PROCESS FOR THE PREPARATION OF N-IODOAMIDES

-

Paragraph 00215-00216, (2015/05/26)

The present invention provides new stable crystalline N-iodoamides - 1-iodo- 3,5,5-trimethylhydantoin (1-ITMH) and 3-iodo-4,4-dimethyl-2-oxazolidinone (IDMO). The present invention further provides a process for the preparation of organic iodides using N-iodoamides of this invention and recovery of the amide co-products from waste water.

PROCESS FOR THE PREPARATION OF IODIDES

-

Page/Page column 34, (2012/01/05)

This invention is directed to a process for the preparation of high yield alkyl or aryl iodide from its corresponding carboxylic acid using N-iodo amides.

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