591-18-4

Basic information

• Product Name: 1-Bromo-3-iodobenzene
• Synonyms: Benzene, 1-bromo-3-iodo-;m-Bromoiodobenzene;1-BROMO-3-IODOBENZENE;3-BROMOIODOBENZENE;3-Bromoiodobenzene m-Bromoiodobenzene;1-Bromo-3-iodobenzene,98%;3-bromoiodbenzene;3-BROMO-1-IODOBENZENE
• CAS NO: 591-18-4
• Molecular Formula: C6H4BrI
• Molecular Weight: 282.9
• EINECS: 209-703-9
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;API intermediates;Miscellaneous;Bromine Compounds;Iodine Compounds;Aryl;C6;Halogenated Hydrocarbons;Organohalides
• Mol File: 591-18-4.mol
• Article Data: 15

Chemical Properties

• Melting Point: −9.3-−9 °C(lit.)
• Boiling Point: 120 °C18 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colourless to light yellow liquid
• Density: 2.219 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0615mmHg at 25°C
• Refractive Index: n20/D 1.66(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• Water Solubility: insoluble
• Sensitive: Light Sensitive
• BRN: 1854384
• CAS DataBase Reference: 1-Bromo-3-iodobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Bromo-3-iodobenzene(591-18-4)
• EPA Substance Registry System: 1-Bromo-3-iodobenzene(591-18-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25
• WGK Germany: 3
• TSCA: T
• HazardClass: IRRITANT, LIGHT SENSITIVE
• Hazardous Substances Data: 591-18-4(Hazardous Substances Data)

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.

InChI:InChI=1/C6H4BrI/c7-5-2-1-3-6(8)4-5/h1-4H

Synthetic route

m-bromobenzoic acid (585-76-2) → 1-Bromo-3-iodobenzene (591-18-4)

Conditions	Yield
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) → 1-Bromo-3-iodobenzene (591-18-4)

Conditions	Yield
With N-iodo-succinimide In acetonitrile at 81℃; for 6h;	77%

carbon monoxide (201230-82-2) + 3-bromo-1-iodylbenzene (150177-91-6) → 1-Bromo-3-iodobenzene (591-18-4) + isophthalic acid (121-91-5) + m-bromobenzoic acid (585-76-2)

Conditions	Yield
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) → 1-Bromo-3-iodobenzene (591-18-4)

Conditions	Yield
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) + phenol (108-95-2) → 1-Bromo-3-iodobenzene (591-18-4) + 1-Bromo-2-iodobenzene (583-55-1) + 1,4-bromoiodobenzene (589-87-7)

Conditions	Yield
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) → 1-Bromo-3-iodobenzene (591-18-4)

Conditions	Yield
Ueberfuehrung in das Diazoperbromid und Zersetzung;

3-bromoaniline (591-19-5) → 1-Bromo-3-iodobenzene (591-18-4)

Conditions	Yield
With iodine

1-Iod-3-(trimethylsilyl)benzol (63520-49-0) → 1-Bromo-3-iodobenzene (591-18-4)

Conditions	Yield
With bromine

3-iodobenzoyl chloride (1711-10-0) → 2-<(trichloromethyl)thio>pyridine (66832-24-4) + 1-Bromo-3-iodobenzene (591-18-4)

Conditions	Yield
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) + m-bromodiphenyliodonium iodide (81447-71-4) → bromobenzene (108-86-1) + diphenylether (101-84-8) + iodobenzene (591-50-4) + 1-Bromo-3-iodobenzene (591-18-4) + 3-bromodiphenyl ether (6876-00-2) + benzene (71-43-2)

Conditions	Yield
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) → 1-Bromo-3-iodobenzene (591-18-4)

Conditions	Yield
With iodobenzene In benzene

1,3-dibromobenzene (108-36-1) → 1-Bromo-3-iodobenzene (591-18-4)

Conditions	Yield
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) + 3-bromo-benzenediazonium; bromide (63467-81-2) → 1-Bromo-3-iodobenzene (591-18-4)

iodine (7553-56-2) + 3-bromo-benzenediazonium; dichloride iodide → 1-Bromo-3-iodobenzene (591-18-4)

iodine (7553-56-2) + m-bromobenzene diazonium nitrate → 1-Bromo-3-iodobenzene (591-18-4)

iodine (7553-56-2) + 3-bromo-benzenediazonium; hexachloroplatinate (IV) → 1-Bromo-3-iodobenzene (591-18-4)

iodine (7553-56-2) + 3-bromophenyldiazonium chloride (20893-74-7) → 1-Bromo-3-iodobenzene (591-18-4)

3-bromo-benzenediazonium; tribromoide + iodine → 1-Bromo-3-iodobenzene (591-18-4)

3-bromo-benzenediazonium; sulfate + iodine → 1-Bromo-3-iodobenzene (591-18-4)

diethyl ether (60-29-7) + 3-bromo-phenyl magnesium (1+); bromide + iodine → 1-Bromo-3-iodobenzene (591-18-4)

m-bis(trimethylsilyl)benzene (2060-89-1) → 1-Bromo-3-iodobenzene (591-18-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: IBr 2: Br2 View Scheme

4-Methyl-1-pentene (691-37-2) + bis(3-bromophenyl)iodonium triflate (1426083-16-0) → 1-Bromo-3-iodobenzene (591-18-4) + 6-bromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene (176088-47-4)

Conditions	Yield
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) + 1-iodo-4-n-propylbenzene (126261-84-5) → 1-Bromo-3-iodobenzene (591-18-4) + 4-propylbenzoyl chloride (52710-27-7)

Conditions	Yield
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) + trimethylsilylacetylene (1066-54-2) → 2-(3-bromophenyl)ethynyltrimethylsilane (3989-13-7)

Conditions	Yield
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) + 3-pyridylboronic acid (1692-25-7) → 3-(3'-bromophenyl)pyridine (4422-32-6)

Conditions	Yield
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) + ethyl 1-(2,5-difluorophenyl)-5-({3-[(2-ethylhexyl)oxy]-3-oxopropyl}thio)-1H-pyrazole-3-carboxylate (1138037-06-5) → ethyl 5-[(3-bromophenyl)thio]-1-(2,5-difluorophenyl)-1H-pyrazole-3-carboxylate (1138037-34-9)

Conditions	Yield
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) + 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)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 100℃; Inert atmosphere;	100%

1-Bromo-3-iodobenzene (591-18-4) + carbon monoxide (201230-82-2) + aniline (62-53-3) → 3-bromo-N-phenylbenzamide (63710-33-8)

Conditions	Yield
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) + 2-methyl-but-3-yn-2-ol (115-19-5) → 2-methyl-4-(3-bromophenyl)-3-butyn-2-ol

Conditions	Yield
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) + [(3-cyanopropyl)diisopropylsilyl]acetylene (1057407-31-4) → 4-{[(3-bromophenyl)ethynyl]diisopropylsilyl}butanenitrile

Conditions	Yield
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) + 1,4-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

Conditions	Yield
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) + phosphorous acid trimethyl ester (121-45-9) → dimethyl (3-bromophenyl)phosphonate (15104-42-4)

Conditions	Yield
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) + phenylacetylene (536-74-3) → 1-phenyl-2-(m-bromo)phenylacetylene (29778-29-8)

Conditions	Yield
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) + trimethylsilylacetylene (1066-54-2) → 1,2-bis(3-bromophenyl)acetylene (153404-60-5)

Conditions	Yield
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) + ethyl acrylate (140-88-5) → ethyl (2E)-3-(3-bromophenyl)prop-2-enoate (59114-88-4)

Conditions	Yield
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) + tris-iso-propylsilyl acetylene (89343-06-6) → 1-bromo-3-[(triisopropylsilyl)ethynyl]benzene

Conditions	Yield
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) → m-bromoiodobenzene dichloride (936252-06-1)

Conditions	Yield
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) → 3-bromoaniline (591-19-5)

Conditions	Yield
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) + 1-Bromo-3-iodobenzene (591-18-4) + 1,3,5-trimethyl-benzene (108-67-8) → 3'-bromo-2,4,6-trimethyl(diphenyliodonium) trifluoromethanesulfonate (1203709-76-5)

Conditions	Yield
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) + thiophenol (108-98-5) → 1,3-bis(phenylthio)benzene (2974-10-9)

Conditions	Yield
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) + 2,2-dimethyl-N-(prop-2-ynyl)propionamide (178320-73-5) → N-(3-(3-bromophenyl)prop-2-ynyl)pivalamide

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine at 20℃; for 0.5h; Inert atmosphere;	99%

N-acetylcystein (616-91-1) + 1-Bromo-3-iodobenzene (591-18-4) → (R)-2-acetamido-3-((3-bromophenyl)thio)propanoic acid (113276-93-0)

Conditions	Yield
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) + 3-(benzofuran-2-yl)-1,1,1,3,5,5,5-heptamethyltrisiloxane (1583285-91-9) → 2-(3’-bromophenyl)benzofuran

Conditions	Yield
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) + Dichlorophenylphosphine (644-97-3) → bis(3-bromophenyl)(phenyl)phosphine oxide

Conditions	Yield
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) + phenylboronic acid (98-80-6) → 1,3-diphenylbenzene (92-06-8)

Conditions	Yield
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) + phenylboronic acid (98-80-6) → 3-bromobiphenyl (2113-57-7)

Conditions	Yield
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) + 1-Bromo-3-iodobenzene (591-18-4) → 1-bromo-3-(4-dibenzofuranyl)benzene (887944-90-3)

Conditions	Yield
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) + 9H-carbazole (86-74-8) → 9-(3-bromophenyl)carbazole (185112-61-2)

Conditions	Yield
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) + 1-Bromo-3-iodobenzene (591-18-4) → 3-bromobenzophenone (1016-77-9)

Conditions	Yield
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) + diphenyl diselenide (1666-13-3) → 3-bromophenyl phenyl selenide (856074-00-5)

Conditions	Yield
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) + ethyl iodide (75-03-6) → 1-bromo-2-ethyl-3-iodobenzene (1344998-09-9)

Conditions	Yield
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) + 1-Bromo-3-iodobenzene (591-18-4) → 2-(3-bromophenylamino)-1-butanol (1184497-56-0)

Conditions	Yield
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) + 1-Bromo-3-iodobenzene (591-18-4) → 1-bromo-3-(prop-1-yn-1-yl)benzene (66952-36-1)

Conditions	Yield
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%

Upstream product

• 59118-28-4 5,7-dihydro-5,5,7,7-tetramethyl-3-(3-nitrophenyl)furo[3,4-e]-1,2,4-triazine 
• 59118-21-7 5,5,7,7-tetramethyl-3-(4-nitrophenyl)-5,7-dihydrofuro[3,4-e][1,2,4]triazine 4-oxide 
• 5911-81-9 (1β,5β)-8-Methyl-8-azabicyclo[3.2.1]octane-3α-carbonitrile 
• 59118-15-9 5,7-dihydro-5,5,7,7-tetramethyl-3-(3-nitrophenyl)furo(3,4-e)-as-triazine 4-oxide 
• 59118-02-4 2,5,8-trichloro-3-[(E)-(6,7-dichloro-1,3-dimethylquinoxalin-2(1H)-ylidene)methyl]anthracene-1,4-dione 
• 59117-78-1 2,2-DICHLOROOCTADECANAL 
• 59117-77-0 2-Chlorododecanoic acid chloride 
• 59117-55-4 N,N-Diethyl-3,7-dimethyl-2,6-octadiene-1-amine 
• 59117-31-6 5-propyloctan-1-ol 
• 591-17-3 3-Bromotoluene 
• 59117-27-0 3-propylhex-2-enoic acid 
• 59117-18-9 4-Hexadecyloxybenzaldehyde 
• 59117-17-8 4-Tetradecyloxybenzaldehyde 
• 5911-70-6 1,6,7,11B-TETRAHYDRO-2H-PYRIDO[2,1-A]ISOQUINOLINE-2,4(3H)-DIONE 

Downstream Products

• 59118-50-2 1H-Benzimidazole-2-carboxylicacid,1-hydroxy-(9CI) 
• 59118-51-3 1H-Benzimidazole,1-hydroxy-(9CI) 
• 59118-76-2 (methylstannylidyne)tris(thioethylene) tristearate 
• 59118-77-3 2,2',2''-[(methylstannylidyne)tris(thio)]triethyl triacetate 
• 59118-78-4 2-mercaptoethyl oleate 
• 59118-79-5 (methylstannylidyne)tris(thioethylene) trioleate 
• 59118-80-8 (butylstannylidyne)tris(thioethylene) trioctanoate 
• 59118-81-9 (dioctylstannylene)bis(thioethylene) dioctanoate 
• 5911-88-6 3-(2,3-dihydroxy-3-methylbutyl)-4,6-dimethoxy-1-methylquinolin-2(1H)-one 
• 59118-93-3 (methylstannylidyne)tris(thioethane-1,2-diyl) trinonan-1-oate 
• 59119-18-5 1-Benzyl-4-hydroxy-4-piperidinecarboxylic acid 
• 59119-49-2 1,3-dimethyl-5-nitro-6-(phenylamino)pyrimidine-2,4(1H,3H)-dione 
• 591-19-5 3-Bromoaniline 
• 59119-51-6 2-[(3-methylphenyl)hydrazono]-3-oxobutanenitrile 

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