2-Bromothiophene supplier | CasNO.1003-09-4

Name
2-Bromothiophene
EINECS 213-699-4
CAS No. 1003-09-4
Article Data78
CAS DataBase
Density 1.714 g/cm³
Solubility Immiscible in water
Melting Point -10 °C
Formula C₄H₃BrS
Boiling Point 149.999 °C at 760 mmHg
Molecular Weight 163.038
Flash Point 47.052 °C
Transport Information UN 2929 6.1/PG 2
Appearance colorless to light yellow transparent liquid
Safety 26-36/37/39-45-61-16-36
Risk Codes 10-25-41-51/53-36/37/38-23/24-22-20/21/22
Molecular Structure
Hazard Symbols T,N,Xn
Synonyms 2-Thienyl bromide;Thiophene, 2-bromo-;2-Bromo Thiophene;2-Bromothiophene 96%;2-Bromothiophen;
PSA 28.24000
LogP 2.51060

Synthetic route

: 188290-36-0
thiophene

: 1003-09-4
2-bromothiophene

Conditions

Conditions	Yield
With hydrogen bromide; dihydrogen peroxide In diethyl ether at 15 - 20℃; for 0.25h;	94%
With tetraethylammonium bromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at 20℃; for 3h; chemoselective reaction;	92%
With phenyltrimethylammonium tribromide In dichloromethane at -10 - 0℃; for 4h;	92.6%

: 110-00-9
furan

: 188290-36-0
thiophene

: 1003-09-4
2-bromothiophene

Conditions

Conditions	Yield
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one for 0.0222222h; microwave irradiation;	85%

: 188290-36-0
thiophene

: 506-68-3
bromocyane

A: 1003-09-4
2-bromothiophene

B: 3141-27-3
2,5-dibromothiophen

Conditions

Conditions	Yield
at 45 - 50℃;
With bromine at 45 - 50℃;
at 45 - 50℃;

...Expand

: 188290-36-0
thiophene

: 79-15-2
N-bromoacetamide

: 1003-09-4
2-bromothiophene

: 188290-36-0
thiophene

A: 1003-09-4
2-bromothiophene

B: 3141-27-3
2,5-dibromothiophen

Conditions

Conditions	Yield
With bromine Behandeln des Produkts mit Wasser; anschliessend mit Natronlauge und mit alkoh. Kali;
With tetrachloromethane; bromine
With bromine; benzene
Behandlung des Reaktionsproduktes mit alkoh. Kali;
With dihydrogen peroxide; ammonium bromide; acetic acid In water for 20h; Reagent/catalyst; Time; Green chemistry; regioselective reaction;	A 80 %Chromat. B 8 %Chromat.

: 3141-27-3
2,5-dibromothiophen

: 1003-09-4
2-bromothiophene

Conditions

Conditions	Yield
With magnesium Behandeln der Magnesiumverbindung mit Salzsaeure;
With quinoline; copper
With indium; 1-n-butyl-3-methylimidazolim bromide at 95℃; for 14h; Green chemistry;	90 %Chromat.
With C33H30F3N2NiO2P; tert-butylmagnesium chloride In tetrahydrofuran; diethyl ether at 70℃; for 24h; Schlenk technique; Inert atmosphere; chemoselective reaction;	81 %Chromat.

: 60-29-7
diethyl ether

: 506-68-3
bromocyane

: [2]thienyl magnesium (1+); bromide

A: 1003-09-4
2-bromothiophene

B: 1003-31-2
thiophene-2-carbonitrile

...Expand

: 60-29-7
diethyl ether

: 506-78-5
cyanogen iodide

: [2]thienyl magnesium (1+); bromide

A: 1003-09-4
2-bromothiophene

B: 3437-95-4
2-Iodothiophene

...Expand

: 60-29-7
diethyl ether

: [2]thienyl magnesium (1+); bromide

: 506-77-4
cyanogen chloride

A: 1003-09-4
2-bromothiophene

B: 1003-31-2
thiophene-2-carbonitrile

...Expand

: 188290-36-0
thiophene

: 128-08-5
N-Bromosuccinimide

: 1003-09-4
2-bromothiophene

Conditions

Conditions	Yield
In acetic acid at 20℃; Rate constant; Thermodynamic data; activation energy;

: 188290-36-0
thiophene

A: 1003-09-4
2-bromothiophene

B: 94800-55-2
2-(phenylselenenyl)thiophene

C: 130789-03-6
2-bromo-5-phenylselenothiophene

Conditions

Conditions	Yield
With aluminum tri-bromide; benzeneseleninyl chloride In dichloromethane for 3.5h; Ambient temperature;	A 76 % Chromat. B n/a C n/a

...Expand

: 3141-27-3
2,5-dibromothiophen

A: 188290-36-0
thiophene

B: 1003-09-4
2-bromothiophene

Conditions

Conditions	Yield
With sodium tetrahydroborate; hydrogen; calcium oxide; palladium In ethanol at 50℃; under 760 Torr; Rate constant;

: 18246-28-1
2-bromo-5-trimethylsilylthiophene

: 1003-09-4
2-bromothiophene

Conditions

Conditions	Yield
In methanol; perchloric acid at 50℃;
In methanol; perchloric acid at 50℃; Rate constant; 1.) other solvents, 2.) k (excit.);
With sodium methylate In methanol at 50℃; Rate constant; deuterium isotope effect;

: 3141-27-3
2,5-dibromothiophen

A: 188290-36-0
thiophene

B: 1003-09-4
2-bromothiophene

C: 872-31-1
3-Bromothiophene

D: 3141-26-2
3,4-dibromothiophene

Conditions

Conditions	Yield
With tetramethylammonium perchlorate In N,N-dimethyl-formamide Product distribution; Mechanism; controlled-potential electrolysis at reticulated vitreous carbon; further reagents;

...Expand

: 188290-36-0
thiophene

: 7726-95-6
bromine

: 1003-09-4
2-bromothiophene

Conditions

Conditions	Yield
at 300 - 500℃;

: 527-72-0
2-thiophenylcarboxylic acid

: 623-11-0
1-methyl-4-nitrosobenzene

: 7726-95-6
bromine

: 1003-09-4
2-bromothiophene

...Expand

: 188290-36-0
thiophene

acetic acid bromoamide (0.5 mol): acetic acid bromoamide (0.5 mol)

: 1003-09-4
2-bromothiophene

: 188290-36-0
thiophene

: 7726-95-6
bromine

A: 1003-09-4
2-bromothiophene

B: 3141-27-3
2,5-dibromothiophen

...Expand

: 188290-36-0
thiophene

A: 1003-09-4
2-bromothiophene

B 2,5-bromo-thiophene: 2,5-bromo-thiophene

Conditions

Conditions	Yield
With tetrachloromethane; bromine

: 3141-27-3
2,5-dibromothiophen

: 7664-41-7
ammonia

: 1066-26-8
sodium acetylide

A: 1003-09-4
2-bromothiophene

B: 3958-03-0
Tetrabromothiophene

...Expand

: 3141-27-3
2,5-dibromothiophen

: 7664-41-7
ammonia

: sodium amide

A: 1003-09-4
2-bromothiophene

B: 3141-24-0
2,3,5-tribromothiophene

C: 3958-03-0
Tetrabromothiophene

...Expand

: 188290-36-0
thiophene

: 7726-95-6
bromine

A: 1003-09-4
2-bromothiophene

B: 3141-27-3
2,5-dibromothiophen

C: 3141-24-0
2,3,5-tribromothiophene

D: 3958-03-0
Tetrabromothiophene

...Expand

: 24287-92-1
2-Bromo-3-iodothiophene

A: 1003-09-4
2-bromothiophene

B: 52770-39-5
2-d1-3-bromothiophene

C: C4H2(2)HBrS

D: 2-deuterio-3-iodothiophene

Conditions

Conditions	Yield
Stage #1: 2-Bromo-3-iodothiophene With ethylmagnesium chloride In tetrahydrofuran at 20℃; Stage #2: With water-d2 In tetrahydrofuran	A 10 % Spectr. B 7 % Spectr. C 75 % Spectr. D 6 % Spectr.

...Expand

: 6165-69-1
Thien-3-ylboronic acid

: 14221-01-3
tetrakis(triphenylphosphine) palladium(0)

: 2-bromophenylbenzyl ether

: 95-56-7
2-hydroxybromobenzene

: 1003-09-4
2-bromothiophene

Conditions

Conditions	Yield
With N-Bromosuccinimide; ammonium chloride; sodium carbonate In tetrahydrofuran; thiophene; 1,2-dimethoxyethane; diethyl ether; water; ethyl acetate
With N-Bromosuccinimide; ammonium chloride; sodium carbonate In tetrahydrofuran; thiophene; 1,2-dimethoxyethane; diethyl ether; water; ethyl acetate

...Expand

: 110-91-8
morpholine

: 4701-17-1
5-bromo-2-thiophencarboxaldehyde

: 1313-13-9
manganese dioxide

aqueous NH4 Cl: aqueous NH4 Cl

: 1826-67-1
vinyl magnesium bromide

: 1003-09-4
2-bromothiophene

Conditions

Conditions	Yield
In tetrahydrofuran; dichloromethane

...Expand

: 626-55-1
3-Bromopyridine

: 139585-50-5
4-chloro-2-trimethylsilylpyridine

A: 1003-09-4
2-bromothiophene

B: 581-46-4
3,3'-bipyridine

C: 1762-41-0
4,4'-dichloro-2,2'-bipyridine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); silver fluoride; silver(l) oxide In N,N-dimethyl-formamide at 90℃; Inert atmosphere;	A 48 %Chromat. B n/a C 26 %Chromat.

...Expand

: 162607-17-2
(5-bromothiophene-2-yl)boronic acid

: 1003-09-4
2-bromothiophene

Conditions

Conditions	Yield
With basolite C300; dihydrogen peroxide In acetone at 20℃; for 2h; chemoselective reaction;

: 61464-23-1
(5-bromothiophen-2-yl)(phenyl)methanol

A: 1003-09-4
2-bromothiophene

B: 65-85-0
benzoic acid

Conditions

Conditions	Yield
With potassium tert-butylate; oxygen In toluene at 80℃; for 14h;	A 17.8 mg B 21.2 mg

: 1003-09-4
2-bromothiophene

: 75-77-4
chloro-trimethyl-silane

: 18246-28-1
2-bromo-5-trimethylsilylthiophene

Conditions

Conditions	Yield
Stage #1: 2-bromothiophene With lithium diisopropyl amide In tetrahydrofuran Stage #2: chloro-trimethyl-silane In tetrahydrofuran	100%
Stage #1: 2-bromothiophene With n-butyllithium; diisopropylamine In tetrahydrofuran at -78 - 0℃; for 0.0833333h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran at -78 - 20℃; for 0.5h;	91%
With lithium diisopropyl amide Yield given. Multistep reaction;

: 1003-09-4
2-bromothiophene

: 98-80-6
phenylboronic acid

: 825-55-8
2-phenylthiophene

Conditions

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; potassium hydroxide In tetrahydrofuran; water at 24℃; for 0.0833333h; Suzuki-Miyaura Coupling; Flow reactor;	100%
With [Pd{κ2(C,C)-C6H4PPh2C(H)CO(C6H4-NO2-4)}Br(Ph-NCS)]; sodium carbonate In methanol at 85℃; for 2h; Reagent/catalyst; Suzuki-Miyaura Coupling;	100%
With palladium diacetate; potassium fluoride; johnphos In tetrahydrofuran at 20℃; for 3h; Suzuki coupling;	99%

: 1003-09-4
2-bromothiophene

: 112-16-3
n-dodecanoyl chloride

: 477334-99-9
1-(5-bromothien-2-yl)-dodecan-1-one

Conditions

Conditions	Yield
With aluminium trichloride In benzene for 0.5h; Heating;	100%

: 1003-09-4
2-bromothiophene

: 882-33-7
diphenyldisulfane

: 16718-12-0
2-(Phenylthio)thiophene

Conditions

Conditions	Yield
Stage #1: 2-bromothiophene With n-butyllithium In diethyl ether; pentane at -78℃; for 0.5h; Inert atmosphere; Stage #2: diphenyldisulfane In diethyl ether; pentane at -78 - 25℃; for 3.5h; Inert atmosphere;	100%
With magnesium; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran for 24h; Heating;	78%

: 1003-09-4
2-bromothiophene

: 2587-76-0
trioctyltin chloride

: tri-n-octyl(thiophen-2-yl)stannane

Conditions

Conditions	Yield
With iodine; magnesium In tetrahydrofuran for 4h; Sonication; Inert atmosphere;	100%
With magnesium In tetrahydrofuran at 30 - 50℃; for 4h; Inert atmosphere; Sonication;	100%

: 1003-09-4
2-bromothiophene

: 96-10-6
diethylaluminium chloride

: diethyl(thiophene)aluminium

Conditions

Conditions	Yield
With n-butyllithium In diethyl ether; hexane at -40 - 0℃; for 3h; Inert atmosphere;	100%

: 1003-09-4
2-bromothiophene

: 64-19-7
acetic acid

: 5370-25-2
2-Acetyl-5-bromothiophene

Conditions

Conditions	Yield
Stage #1: 2-bromothiophene; acetic acid With trifluoroacetic anhydride In dichloromethane at 20℃; for 0.25h; Stage #2: With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 1.5h;	100%
Stage #1: 2-bromothiophene; acetic acid With trifluoroacetic anhydride In dichloromethane at 20℃; for 0.25h; Stage #2: With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 1h;

: 1003-09-4
2-bromothiophene

: 17950-97-9
tri(thien-2-yl)silane

Conditions

Conditions	Yield
Stage #1: 2-bromothiophene With magnesium In tetrahydrofuran for 1.5h; Inert atmosphere; Reflux; Stage #2: With dichloro(N,N,N’,N‘-tetramethylethylenediamine)zinc; trichlorosilane In tetrahydrofuran at 0 - 20℃; for 12.25h; Inert atmosphere;	100%

: 1003-09-4
2-bromothiophene

: 536-74-3
phenylacetylene

: 4805-17-8
2-(phenylethynyl)thiophene

Conditions

Conditions	Yield
With copper(l) iodide; diisopropylamine; triphenylphosphine; silica gel; palladium at 85℃; for 18h; Sonogashira coupling;	99.5%
With C25H23BrN7Pd(1+)*Br(1-); potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h; Sonogashira Cross-Coupling; Schlenk technique;	99%
With 2F6P(1-)*C36H26N8Pd2(2+); tetra-(n-butyl)ammonium iodide; potassium carbonate In ethanol at 120℃; for 24h; Sonogashira Cross-Coupling;	99%

: 1003-09-4
2-bromothiophene

: 5370-19-4
5-iodothiophene-2-carbaldehyde

: 110046-60-1
5'-bromo-2,2'-bithiophene-5-carboxaldehyde

Conditions

Conditions	Yield
In acetonitrile for 3h; Irradiation;	99%
In acetonitrile for 3h; Irradiation;	83.4%

: 1003-09-4
2-bromothiophene

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

: 133844-84-5
2-methyl-4-(thien-2-yl)but-3-yn-2-ol

Conditions

Conditions	Yield
With copper(l) iodide; triethylamine; triphenylphosphine at 90℃; for 48h; Sonogashira coupling; Inert atmosphere;	99%
With pyrrolidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In water at 70℃; for 4h;	89%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine for 2h;	80%

: 1003-09-4
2-bromothiophene

: 1066-54-2
trimethylsilylacetylene

: 40231-03-6
2-(trimethylsilylethynyl)thiophene

Conditions

Conditions	Yield
With 1,2-bis(thiophen-2-ylethynyl)benzene; bis-triphenylphosphine-palladium(II) chloride; triethylamine In acetonitrile for 17h; Sonogashira coupling; Inert atmosphere; Reflux;	99%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane In N,N-dimethyl-formamide at 120℃; for 0.5h; microwave-assisted Sonogashira reaction; Microwave irradiation;	96%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran	95%

: 1003-09-4
2-bromothiophene

: 616-45-5
2-pyrrolidinon

: 1-(thiophen-2-yl)pyrrolidin-2-one

Conditions

Conditions	Yield
With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine at 90 - 110℃;	99%
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In 1,4-dioxane at 110℃; for 24h;	99%
With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 110℃; for 24h; Inert atmosphere;	99%
With potassium phosphate; copper(l) iodide; (S,S)-1,2-diaminocyclohexane In 1,4-dioxane at 110℃; for 15h;	96%
With potassium phosphate; copper(l) iodide; (S,S)-1,2-diaminocyclohexane In 1,4-dioxane at 110℃; for 15h;	96%

: 1003-09-4
2-bromothiophene

: 100-61-8
N-methylaniline

: 2-(N-methyl-N-phenylamino)thiophene

Conditions

Conditions	Yield
With palladium diacetate; sodium t-butanolate; ruphos In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Green chemistry;	99%
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 20℃; for 16h;	82%
With 1,2,3-trimethoxybenzene; bis(tri-t-butylphosphine)palladium(0); Et3CONa In benzene-d6 at 75℃; Kinetics; Further Variations:; Reagent concentrations;

: 1003-09-4
2-bromothiophene

: 28686-98-8
3-bromo-2-(thiophen-3-yl)thiophene

: 113201-28-8
2,3':2',3"-terthiophene

Conditions

Conditions	Yield
Stage #1: 2-bromothiophene With magnesium In diethyl ether for 0.5h; Heating; Stage #2: 3-bromo-2-(thiophen-3-yl)thiophene; Ni(dppp)2Cl2 In diethyl ether Heating;	99%

: 1003-09-4
2-bromothiophene

: 1692-25-7
3-pyridylboronic acid

: 21298-53-3
3-thiophen-2-yl-pyridine

Conditions

Conditions	Yield
With potassium phosphate; palladium dichloride; S-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine In butan-1-ol at 100℃; for 20h; Suzuki coupling; Inert atmosphere;	99%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane at 90℃; for 1h; Suzuki coupling;	62%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 80℃; for 24h; Suzuki-Miyaura coupling; Reflux;	62%
With bis(η3-allyl-μ-chloropalladium(II)); N,N,N′,N′-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine; potassium carbonate In N,N-dimethyl acetamide; butan-1-ol at 120℃; for 12h; Reagent/catalyst; Time; Suzuki Coupling; Inert atmosphere;

: 1003-09-4
2-bromothiophene

: 2996-92-1
phenyl trimethylsiloxane

: 825-55-8
2-phenylthiophene

Conditions

Conditions	Yield
With sodium hydroxide; 4,4'-dichlorobenzophenone oxime-derived palladacycle at 120℃; under 7500.6 Torr; for 0.166667h; Hiyama coupling; microwave irradiation;	99%
With potassium fluoride; propylene glycol; chloro-[2-(9-phenyl-1,10-phenanthrolin-2-yl)phenyl]palladium In dichloromethane at 100℃; for 12h; Hiyama Coupling; Inert atmosphere;	91%
With sodium hydroxide In ethanol; water at 110℃; for 0.133333h; Hiyama coupling; Microwave irradiation;	90%

: 1003-09-4
2-bromothiophene

: 365564-11-0
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole

: 3-(thiophen-2-yl)-1-(triisopropyl-silanyl)-1H-pyrrole

Conditions

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 100℃; for 2h; Suzuki-Miyaura cross-coupling;	99%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 100℃; for 2h; Suzuki-Miyaura reaction;	99%

: 1003-09-4
2-bromothiophene

: 1461-22-9
tributyltin chloride

: 143724-36-1
(5-bromothiophen-2-yl)tributylstannane

Conditions

Conditions	Yield
With n-BuLi; i-Pr2NH In tetrahydrofuran; hexane (N2); Schlenk technique; n-BuLi (1.1 equiv.) added to soln. of i-Pr2NH (1.1 equiv.) in THF at -78°C; mixt. stirred at -78°C for 15min; transferred via cannula to soln. of BrC4H3S (1 equiv.) in THF at - 78°C; soln. stirred for 1 h; Bu3SnCl (1.1 equiv.) added; soln. stirred at -78°C for 1 h and atroom temp. for 1 h; Et2O and satd. Na2CO3 added; extd. (satd. Na2CO3, H 2O); org. phase dried (MgSO4); filtered on Celite; evapd. (vac.);	99%

Yield

With n-BuLi; i-Pr2NH In tetrahydrofuran; hexane (N2); Schlenk technique; n-BuLi (1.1 equiv.) added to soln. of i-Pr2NH (1.1 equiv.) in THF at -78°C; mixt. stirred at -78°C for 15min; transferred via cannula to soln. of BrC4H3S (1 equiv.) in THF at - 78°C; soln. stirred for 1 h; Bu3SnCl (1.1 equiv.) added; soln. stirred at -78°C for 1 h and atroom temp. for 1 h; Et2O and satd. Na2CO3 added; extd. (satd. Na2CO3, H 2O); org. phase dried (MgSO4); filtered on Celite; evapd. (vac.);

99%

: 1003-09-4
2-bromothiophene

: 111-88-6
Octanethiol

: 55191-03-2
2-octyl 2-thiophenyl sulfide

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine In toluene for 3h; Inert atmosphere; Reflux;	99%
With (R)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; palladium diacetate; caesium carbonate In 1,2-dimethoxyethane at 110℃; Inert atmosphere;	98%

: 1003-09-4
2-bromothiophene

: 1972-28-7
diethylazodicarboxylate

: 1187530-03-5
diethyl 1-(thiophen-2-yl)hydrazine-1,2-dicarboxylate

Conditions

Conditions	Yield
With magnesium; ethylene dibromide In tetrahydrofuran at 20℃; for 1.5h; Barbier reaction; Sonication;	99%

: 1003-09-4
2-bromothiophene

: 201802-67-7
4-(diphenylamino)phenyl boronic acid

: N,N-diphenyl-4-(thiophen-2-yl)aniline

Conditions

Conditions	Yield
With potassium phosphate tribasic heptahydrate; palladium diacetate In water; isopropyl alcohol at 80℃; for 1h; Suzuki reaction;	99%
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; for 0.5h; Suzuki Coupling;	98%
With potassium carbonate In water; toluene at 90℃; for 0.5h; Suzuki-Miyaura Coupling;	97%

: 1003-09-4
2-bromothiophene

: 1864-94-4
phenyl formate

: 881-89-0
phenyl thiophene-2-carboxylate

Conditions

Conditions	Yield
With palladium diacetate; triethylamine; tri tert-butylphosphoniumtetrafluoroborate In acetonitrile at 80℃; Inert atmosphere;	99%
With bis(benzonitrile)palladium(II) dichloride; triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 60℃; for 20h; Inert atmosphere;	92%
With {(Pd{Fe(η5-C5H5)(η5-C5H3C(CH3)=NC6H4CH3-4)}(μ-Cl))2}; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 120℃; for 23h; Inert atmosphere;	75%

: 1003-09-4
2-bromothiophene

: 1-ethyl-2,3-bis(4-methoxyphenyl)-1-(2-methylallyl)guanidine hydrochloride

: 1-ethyl-N,3-bis(4-methoxyphenyl)-4-methyl-4-(thiophen-2-ylmethyl)imidazolidin-2-iminehydrochloride

Conditions

Conditions	Yield
Stage #1: 1-ethyl-2,3-bis(4-methoxyphenyl)-1-(2-methylallyl)guanidine hydrochloride With tris-(dibenzylideneacetone)dipalladium(0); nixantphos In toluene at 20℃; for 0.0333333h; Inert atmosphere; Stage #2: 2-bromothiophene In toluene at 20 - 107℃; for 16h;	99%

: 1003-09-4
2-bromothiophene

: 1356823-20-5
C11H13BN2O5

: 2-methoxy-3-(2-thienyl)pyridine

Conditions

Conditions	Yield
With potassium phosphate; [Pd(η(5)-C5H5)Fe(η(5)-C5H3-C(CH3)=N-C6H4-4-CH3)Cl(P(C6H5)3)] In ethanol; water at 100℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Green chemistry;	99%

: 1003-09-4
2-bromothiophene

: 2-(benzo[c][1,2,5]oxadiazoboronic acid)

: 1579939-75-5
5-(thiophene-2-yl)benzo[c][1,2,5]oxadiazole

Conditions

Conditions	Yield
With potassium phosphate; [Pd(η(5)-C5H5)Fe(η(5)-C5H3-C(CH3)=N-C6H4-4-CH3)Cl(P(C6H5)3)]; tetrabutylammomium bromide In water at 100℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Green chemistry;	99%

: 1003-09-4
2-bromothiophene

: 6999-03-7
1-bromo-4-(trimethylsilyl)benzene

: [4-(2-thienyl)phenyl](trimethyl)silane

Conditions

Conditions	Yield
Stage #1: 2-bromothiophene With magnesium In tetrahydrofuran for 1h; Reflux; Inert atmosphere; Stage #2: 1-bromo-4-(trimethylsilyl)benzene With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran at 0 - 20℃; Kumada Cross-Coupling; Inert atmosphere;	99%

: 1003-09-4
2-bromothiophene

: 1429621-76-0
2-(3,4,5-trimethoxybenzoyl)-4-phenyl-1H-imidazole

: 1429621-98-6
C23H20N2O4S

Conditions

Conditions	Yield
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 20 - 110℃; for 48h; Inert atmosphere; Schlenk technique;	98.2%

: 1003-09-4
2-bromothiophene

: 3141-27-3
2,5-dibromothiophen

Conditions

Conditions	Yield
With N-Bromosuccinimide; perchloric acid In tetrachloromethane for 24h; Ambient temperature;	98%
With hexabromocyclopenta-1,3-diene In acetonitrile Heating;	44%
With bromine In tetrachloromethane Ambient temperature;	44.3%

: 1003-09-4
2-bromothiophene

: 17933-03-8
m-tolylboronic acid

: 85553-43-1
2-(3-methylphenyl)thiophene

Conditions

Conditions	Yield
Stage #1: 2-bromothiophene; m-tolylboronic acid With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tri-t-butylphosphonium tetraphenylborate complex In tetrahydrofuran for 0.0833333h; Inert atmosphere; Stage #2: With sodium hydroxide In tetrahydrofuran; water at 65℃; for 24h; Inert atmosphere;	98%
	86%
Stage #1: 2-bromothiophene; m-tolylboronic acid With potassium phosphate In ethanol at 20℃; for 0.166667h; Suzuki Coupling; Stage #2: With tetrabutylammomium bromide; palladium diacetate In ethanol at 20℃; for 10h; Suzuki Coupling;	70%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene for 2h; Suzuki coupling; Heating;

2-Bromothiophene Specification

The 2-Bromothiophene is an organic compound with the formula C₄H₃BrS. The IUPAC name of this chemical is 2-bromothiophene. With the CAS registry number 1003-09-4, it is also named as Bromothiophene. The product's categories are Thiophenes; Halides; Thiophenes & Benzothiophenes; Thiophene & Benzothiophene; Thiophenes & Benzothiophenes. Besides, it is a colorless to light yellow transparent liquid, which should be stored in a closed dark and cool place. It can be used for organic synthesis and pharmaceutical intermediates.

Physical properties about 2-Bromothiophene are: (1)ACD/LogP: 2.94; (2)ACD/LogD (pH 5.5): 2.944; (3)ACD/LogD (pH 7.4): 2.944; (4)ACD/BCF (pH 5.5): 101.742; (5)ACD/BCF (pH 7.4): 101.742; (6)ACD/KOC (pH 5.5): 951.875; (7)ACD/KOC (pH 7.4): 951.875; (8)Polar Surface Area: 28.24 Å²; (9)Index of Refraction: 1.595; (10)Molar Refractivity: 32.327 cm³; (11)Molar Volume: 95.098 cm³; (12)Polarizability: 12.816×10^-24cm³; (13)Surface Tension: 41.199 dyne/cm; (14)Density: 1.714 g/cm³; (15)Flash Point: 47.052 °C; (16)Enthalpy of Vaporization: 37.095 kJ/mol; (17)Boiling Point: 149.999 °C at 760 mmHg; (18)Vapour Pressure: 4.993 mmHg at 25°C.

Preparation: this chemical can be prepared by thiophene. This reaction will need reagent PyHBrCl₂ and solvent aq. methanol. The reaction time is 5 min with reaction temperature of 20 °C. The yield is about 74%.

Uses of 2-Bromothiophene: it can be used to produce 4-(5-bromo-thiophen-2-yl)-4-oxo-butyric acid at temperature of -5 - 20 °C. This reaction is a kind of Friedel-Crafts acylation. It will need reagent AlCl₃ and solvent nitrobenzene. The yield is about 95%.

When you are using this chemical, please be cautious about it as the following:
It is flammable and harmful by inhalation, in contact with skin and if swallowed. Please keep away from sources of ignition - No smoking.It is toxic by inhalation, in contact with skin and if swallowed and very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin and risk of serious damage to eyes. When you are using it, wear suitable gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc(sc1)Br
(2)InChI: InChI=1/C4H3BrS/c5-4-2-1-3-6-4/h1-3H
(3)InChIKey: TUCRZHGAIRVWTI-UHFFFAOYAQ
(4)Std. InChI: InChI=1S/C4H3BrS/c5-4-2-1-3-6-4/h1-3H
(5)Std. InChIKey: TUCRZHGAIRVWTI-UHFFFAOYSA-N

Product Name

2-Bromothiophene

Synthetic route

2-Bromothiophene Specification

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