Conditions | Yield |
---|---|
With acetic acid; zinc In water at 20℃; | 92% |
With hydrogen bromide; cadmium(II) chloride In methanol; dichloromethane at 35℃; for 5h; | 89% |
In methanol; dichloromethane at 35℃; for 5h; Product distribution; electrolysis in presence of CdCl2 and HBr at 1 A (83 mA/cm2), 13.5-11.5 V; other conditions and other bromothiophenes investigated; | 89% |
Conditions | Yield |
---|---|
Stage #1: Tetrabromothiophene With n-butyllithium In diethyl ether; hexane at 0℃; for 1.66667 - 1.83333h; Argon atmosphere; Stage #2: C4Br2Li2S With water at 0℃; | 77% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide divided cell electrolysis at constant potential (-1.70 V); 0.1 M tetraethylammonium bromide, mercury electrode; | A 74% B 3% |
Conditions | Yield |
---|---|
With sodium amide; ferric nitrate In ammonia | A 72% B n/a |
2-bromothiophene
A
3,4-dibromothiophene
B
2,3,5-tribromothiophene
C
2,3,4-tribromothiophene
D
Tetrabromothiophene
Conditions | Yield |
---|---|
With potassium tert-butylate; sodium amide In ammonia for 3h; Further byproducts given; | A 65% B n/a C n/a D n/a |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide divided cell electrolysis at constant potential (-1.20 V); 0.1 M tetraethylammonium bromide, mercury electrode; | 60% |
With methyl bromide; diethyl ether; magnesium Erhitzen des Reaktionsprodukts mit Wasserdampf; |
Conditions | Yield |
---|---|
Stage #1: thiophene With bromine In chloroform for 4h; Heating; Stage #2: With acetic acid; zinc In water Heating; | A 23% B 51% |
3,4-dibromo-2,5-dimethylthiophene
A
3,4-dibromothiophene
B
3,4-dibromo-2,5-dimethylthiophene-1,1-dioxide
C
C6H2Br2O3S
D
3,4-Dibromo-2,5-dimethylthiophene S-monoxide
Conditions | Yield |
---|---|
With aluminum oxide; ferric hydroxide; ethylenediaminetetraacetic acid; dihydrogen peroxide In methanol; water at 50 - 55℃; for 5h; Mechanism; | A 36% B 10% C 16% D 30% |
In methanol; water at 50 - 55℃; for 5h; Mechanism; | A 8% B 10% C 16% D 30% |
Conditions | Yield |
---|---|
With methyl bromide; diethyl ether; magnesium Behandeln des Reaktionsprodukts mit Wasser; |
2,5-dibromothiophen
A
thiophene
B
2-bromothiophene
C
3-Bromothiophene
D
3,4-dibromothiophene
Conditions | Yield |
---|---|
With tetramethylammonium perchlorate In N,N-dimethyl-formamide Product distribution; Mechanism; controlled-potential electrolysis at reticulated vitreous carbon; further reagents; |
thiophene
3,4-dibromothiophene
Conditions | Yield |
---|---|
With bromine; acetic acid; zinc Yield given. Multistep reaction; |
Tetrabromothiophene
acetic acid
A
3-Bromothiophene
B
3,4-dibromothiophene
formic acid
3,4-dibromo-thiophene-2-carboxylic acid-(3,4-dibromo-[2]thienylmethyl ester)
A
3,4-dibromothiophene
B
(3,4-dibromo-thiophen-2-yl)-methanol
C
3,4-dibromo-2-thiophenecarboxylic acid
3,4-dibromo-2,5-thiophenedicarboxaldehyde
A
3,4-dibromothiophene
B
(3,4-dibromo-thiophen-2-yl)-methanol
C
formic acid
D
3,4-dibromo-2-thiophenecarboxylic acid
Conditions | Yield |
---|---|
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether Reflux; | 100% |
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether Cooling with ice; Reflux; | 89% |
With [1,3-bis(diphenylphosphino)propane]nickel(II) dichloride In tetrahydrofuran for 4h; Heating; | 64% |
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran; diethyl ether at 0 - 20℃; |
3,4-dibromothiophene
tetradecanoyl chloride
(3,4-dibromothien-2-yl)-tridecyl-ketone
Conditions | Yield |
---|---|
aluminum (III) chloride In dichloromethane at 0℃; Friedel Crafts Acylation; Inert atmosphere; | 100% |
Stage #1: 3,4-dibromothiophene; tetradecanoyl chloride With aluminum (III) chloride In dichloromethane at 0℃; Inert atmosphere; Stage #2: With hydrogenchloride In dichloromethane; water |
2-(ethoxycarbonyl)phenylboronic acid
3,4-dibromothiophene
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 100℃; for 16h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube; | 100% |
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 100℃; Suzuki-Miyaura Coupling; |
3,4-dibromothiophene
chloro-trimethyl-silane
3,4-dibromothiophene-2,5-diyl-bis(trimethylsilane)
Conditions | Yield |
---|---|
Stage #1: 3,4-dibromothiophene With lithium diisopropyl amide In diethyl ether; hexane at 0℃; for 2h; Stage #2: chloro-trimethyl-silane In diethyl ether; hexane at -78 - 20℃; | 99.6% |
Stage #1: 3,4-dibromothiophene With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 0.5h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 0.5h; Inert atmosphere; | 72% |
With lithium diisopropyl amide Inert atmosphere; |
3,4-dibromothiophene
4-d1-3-bromothiophene
Conditions | Yield |
---|---|
Stage #1: 3,4-dibromothiophene With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 1.5h; Stage #2: With 2D(1+)*SO4(2-)=D2SO4; water-d2 In tetrahydrofuran | 99% |
Stage #1: 3,4-dibromothiophene With n-butyllithium In diethyl ether; hexane at -78℃; for 0.416667h; Stage #2: With d(4)-methanol In diethyl ether; hexane at -78 - 20℃; for 0.583333h; | 58% |
With n-butyllithium; water-d2 In diethyl ether; hexane at -70℃; for 0.333333h; |
3,4-dibromothiophene
Conditions | Yield |
---|---|
bis-triphenylphosphine-palladium(II) chloride In benzene at 80℃; for 24h; | 99% |
3,4-dibromothiophene
acetyl chloride
1-(3,4-dibromothiophen-2-yl)ethanone
Conditions | Yield |
---|---|
Stage #1: 3,4-dibromothiophene With aluminum (III) chloride In dichloromethane at 0℃; Friedel Crafts acylation; Stage #2: acetyl chloride at 0℃; Friedel Crafts acylation; | 98% |
Stage #1: 3,4-dibromothiophene; acetyl chloride With aluminum (III) chloride In dichloromethane at 0℃; Inert atmosphere; Stage #2: With hydrogenchloride; water In dichloromethane | 95% |
With aluminium trichloride; Petroleum ether | |
With aluminium trichloride In dichloromethane Friedel-Crafts acylation; cooling; | |
Stage #1: 3,4-dibromothiophene; acetyl chloride With aluminum (III) chloride In dichloromethane at 0℃; Inert atmosphere; Stage #2: With hydrogenchloride In dichloromethane; water |
3,4-dibromothiophene
n-hexylmagnesium bromide
3,4-di-n-hexylthiophene
Conditions | Yield |
---|---|
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether | 98% |
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether at 0℃; for 20h; Inert atmosphere; Reflux; | 93% |
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether for 12h; Kumada Cross-Coupling; Cooling with ice; | 93% |
3,4-dibromothiophene
5,5-dimethyl-5H-dibenzo[b,d]stannole
phenanthro[9,10-c]thiophene
Conditions | Yield |
---|---|
With bis(tri-t-butylphosphine)palladium(0) In tetrahydrofuran at 60℃; for 12h; | 98% |
3,4-dibromothiophene
chloroformic acid ethyl ester
4.-brorno-thiophene-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: 3,4-dibromothiophene With isopropylmagnesium chloride In tetrahydrofuran at 0 - 5℃; for 5h; Stage #2: chloroformic acid ethyl ester In tetrahydrofuran at 10 - 20℃; for 16h; Stage #3: With water In tetrahydrofuran at 20℃; for 0.166667h; | 98% |
Stage #1: 3,4-dibromothiophene With isopropylmagnesium bromide In tetrahydrofuran at 0℃; for 5h; Stage #2: chloroformic acid ethyl ester at 0 - 20℃; for 14h; | 82% |
With isopropylmagnesium chloride In tetrahydrofuran at 0 - 25℃; |
Conditions | Yield |
---|---|
97% | |
With aluminium trichloride In carbon disulfide for 1h; Heating; | |
With aluminum (III) chloride In carbon disulfide Friedel Crafts acylation; |
3,4-dibromothiophene
triisopropylsilyl chloride
Conditions | Yield |
---|---|
Stage #1: 3,4-dibromothiophene With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: triisopropylsilyl chloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | 97% |
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | 97% |
3,4-dibromothiophene
2-Bromoacetyl bromide
2-bromo-1-(3,4-dibromothiophen-2-yl)ethanone
Conditions | Yield |
---|---|
With aluminum (III) chloride In carbon disulfide at 20℃; Friedel Crafts acylation; Reflux; | 96% |
Conditions | Yield |
---|---|
Stage #1: phenylboronic acid With tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate; triphenylphosphine In toluene at 20℃; Suzuki coupling; Inert atmosphere; Stage #2: 3,4-dibromothiophene In toluene Suzuki coupling; Inert atmosphere; Stage #3: With sodium carbonate In toluene at 20℃; Inert atmosphere; Reflux; | 96% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; benzene Suzuki coupling; Inert atmosphere; Reflux; | 68% |
3,4-dibromothiophene
methanol
A
2,3-dimethoxythiophene
B
3-bromo-4-methoxythiophene
Conditions | Yield |
---|---|
With sodium; potassium iodide; copper(II) oxide at 97℃; for 72h; Inert atmosphere; | A 96% B n/a |
Conditions | Yield |
---|---|
With n-butyllithium In diethyl ether | 96% |
Conditions | Yield |
---|---|
Stage #1: 1-Bromotetradecane With iodine; magnesium In diethyl ether at 0℃; for 1h; Stage #2: 3,4-dibromothiophene With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether at 0 - 20℃; for 12h; | 96% |
3,4-dibromothiophene
dibromo-3,4 nitro-2 thiophene
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid In chloroform at 50℃; for 24h; | 95% |
With nitric acid; acetic anhydride | |
With nitric acid; acetic anhydride; acetic acid |
Conditions | Yield |
---|---|
1,3-bis[(diphenylphosphino)propane]dichloronickel(II) | 95% |
dichloro[propane-1,3-diylbis(diphenylphosphane)]nickel(II) In diethyl ether for 20h; Heating; | 95 % Chromat. |
Conditions | Yield |
---|---|
With potassium carbonate; allylpalladium(II) chloride dimer; Tedicyp In N,N-dimethyl-formamide at 140℃; for 24h; Heck reaction; | 95% |
Conditions | Yield |
---|---|
With [1,1'-bis(diphenylphosphino)-ferrocene]palladium(II) chloride-dichlormethane complex In N,N-dimethyl acetamide at 80℃; for 12h; | 95% |
3,4-dibromothiophene
n-butyl magnesium bromide
formaldehyd
3,4-dibutyl-5-(hydroxymethyl)thiophene
Conditions | Yield |
---|---|
Stage #1: 3,4-dibromothiophene; n-butyl magnesium bromide With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) Kumada Cross-Coupling; Inert atmosphere; Schlenk technique; Stage #2: With n-butyllithium In tetrahydrofuran at 0℃; for 0.75h; Inert atmosphere; Schlenk technique; Stage #3: formaldehyd In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Schlenk technique; | 95% |
3,4-dibromothiophene
P-toluenesulfonyl cyanide
4-bromothiophene-3-carbonitrile
Conditions | Yield |
---|---|
Stage #1: 3,4-dibromothiophene With isopropylmagnesium chloride In tetrahydrofuran at 0 - 5℃; Stage #2: P-toluenesulfonyl cyanide In tetrahydrofuran at 0 - 5℃; Stage #3: With water In tetrahydrofuran for 0.166667h; | 94.3% |
Conditions | Yield |
---|---|
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran; diethyl ether at 0 - 20℃; | 94% |
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether at 25℃; for 16h; Kumada Cross-Coupling; | 76% |
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether at 20℃; for 48h; | 43% |
3,4-dibromothiophene
thiophene-3,4-diamine
Conditions | Yield |
---|---|
With [Cu2(2,7-bis(pyridin-2-yl)-l,8-naphthyridine)(OH)(CF3COO)3]; tetrabutylammomium bromide; ammonia; caesium carbonate In ethylene glycol at 140℃; for 16h; Sealed tube; chemoselective reaction; | 94% |
3,4-dibromothiophene
3,4-dichlorothiophene
Conditions | Yield |
---|---|
With copper(l) chloride In N,N-dimethyl-formamide for 24h; Reflux; Inert atmosphere; | 94% |
3,4-dibromothiophene
Dimethyldisulphide
3-bromo-4-(methylthio)thiophene
Conditions | Yield |
---|---|
Stage #1: 3,4-dibromothiophene With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h; Stage #2: Dimethyldisulphide In diethyl ether; hexane at -78 - 20℃; for 12h; | 93% |
With n-butyllithium In diethyl ether; hexane 1.) - 80 deg C, 1 h, 2.) -70 deg C, 3 h; | 50% |
With n-butyllithium In diethyl ether; water | |
Stage #1: 3,4-dibromothiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.133333h; Stage #2: Dimethyldisulphide In tetrahydrofuran; hexane at -78℃; for 0.05h; |
3,4-dibromothiophene
4-butylphenylboronic acid
Conditions | Yield |
---|---|
With potassium fluoride; tetrakis(triphenylphosphine) palladium(0) In water; toluene for 19h; Inert atmosphere; Reflux; | 93% |
With potassium fluoride; tetrakis(triphenylphosphine) palladium(0) In water; toluene Heating; | 60% |
Conditions | Yield |
---|---|
With potassium iodide; copper(II) oxide In ethanol at 120℃; under 3000.3 Torr; for 6h; Temperature; Inert atmosphere; Autoclave; | 92.1% |
Conditions | Yield |
---|---|
With aluminum (III) chloride at 0 - 20℃; | 92% |
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 16h; Friedel-Crafts Acylation; | 92% |
With aluminium trichloride; Petroleum ether |
The 3,4-Dibromothiophene is an organic compound with the formula C4H2Br2S. The IUPAC name of this chemical is 3,4-dibromothiophene. With the CAS registry number 3141-26-2, it is also named as Thiophene, 3,4-dibromo-. The product's categories are Thiophenes; Blocks; Thiazoles; Halides; Heterocycles; Thiophene & Benzothiophene; Miscellaneous; Halogenated; Organohalides; Thiophene; Thiophens; Halogenated Heterocycles; Heterocyclic Building Blocks; Thiophenes Building Blocks. Besides, it is a clear colorless to yellow liquid, which should be stored in a cool and dry place.
Physical properties about 3,4-Dibromothiophene are: (1)ACD/LogP: 3.21; (2)ACD/LogD (pH 5.5): 3.21; (3)ACD/LogD (pH 7.4): 3.21; (4)ACD/BCF (pH 5.5): 162.16; (5)ACD/BCF (pH 7.4): 162.16; (6)ACD/KOC (pH 5.5): 1328.88; (7)ACD/KOC (pH 7.4): 1328.88; (8)Polar Surface Area: 28.24 Å2; (9)Index of Refraction: 1.638; (10)Molar Refractivity: 40.01 cm3; (11)Molar Volume: 111.2 cm3; (12)Polarizability: 15.86×10-24cm3; (13)Surface Tension: 47 dyne/cm; (14)Density: 2.174 g/cm3; (15)Flash Point: 90.4 °C; (16)Enthalpy of Vaporization: 43.93 kJ/mol; (17)Boiling Point: 221.5 °C at 760 mmHg; (18)Vapour Pressure: 0.159 mmHg at 25°C.
Preparation: this chemical can be prepared by tetrabromo-thiophene. This reaction will need reagent Zn and AcOH.
Uses of 3,4-Dibromothiophene: it can be used to produce 4-bromo-thiophene-3-carbaldehyde. It will need reagent n-BuLi.
When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation, in contact with skin and if swallowed. 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. When you are using it, wear suitable gloves and eye/face protection.
You can still convert the following datas into molecular structure:
(1)SMILES: Brc1cscc1Br
(2)InChI: InChI=1/C4H2Br2S/c5-3-1-7-2-4(3)6/h1-2H
(3)InChIKey: VGKLVWTVCUDISO-UHFFFAOYAN
(4)Std. InChI: InChI=1S/C4H2Br2S/c5-3-1-7-2-4(3)6/h1-2H
(5)Std. InChIKey: VGKLVWTVCUDISO-UHFFFAOYSA-N
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