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CAS No. : | 3141-26-2 |
Formula : | C4H2Br2S |
M.W : | 241.93 |
SMILES Code : | C1=C(Br)C(=CS1)Br |
MDL No. : | MFCD00005465 |
InChI Key : | VGKLVWTVCUDISO-UHFFFAOYSA-N |
Pubchem ID : | 18452 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: With n-butyllithium In diethyl ether at -78℃; for 1 h; Inert atmosphere Stage #2: With iodine In diethyl ether at -78 - 25℃; for 1 h; |
1) Prepared according to the flow chart in Figure 1 1)3,4-dibromothiophene (24.2 g, 100 mmol) was dissolved in anhydrous diethyl ether,N2 protection,Cooling to -78 ,N-BuLi (66 ml, 105 mmol, 1.6 M) was slowly added dropwise,After reaction for 1 h at -78 & lt; 0 & gt; C, I2 (26.67 g, 105 mmol)Continue stirring for 1 h and warm to room temperature (25 ° C).The reaction solution was quenched with NaHSO3, extracted with ether, dried over Mg2SO4, dried and distilled under reduced pressure to give 3-bromo-4-iodothiophene (22.55 g, 78percent)Color liquid 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With n-butyllithium; In tetrahydrofuran; | General procedure: DNT-1221 derivatives 32-36 were synthesized using the route shown in Scheme 3. Formylation with n-butyllithium and DMF was used to convert 3,4-dibromothiophene to 3-bromothiophene-4-carbaldehyde 23 in 77% yield.[38,39] Suzuki-Miyaura coupling was then used to add the first styryl group to one side of the thiophene ring to give 3-formyl-4-styrylthiophenes 24-26 in 10-77% yield (Table 5), from which asymmetric distyrylthiophenes could easily be synthesized. The trifluoromethyl-substituted styrylboronic acid gave the highest yields. A Horner-Wadsworth-Emmons reaction was used to add the second substituted styryl group to the other side of the thiophene ring (Table 6), creating 3,4-distyrylthiophenes 27-31 in yields from 16-95%. The CF3-substituted benzylphosphonic esters used in the creation of 29 and 30 gave higher yields compared to those with other substituents. The Suzuki-Miyaura coupling was performed before the Horner-Wadsworth-Emmons reaction in this route because the 1,4-diphenyl-1,3-butadiene byproducts formed from the Suzuki-Miyaura reaction were easier to separate from the more polar 3-formyl-4-styrylthiophenes than from 3,4-distyrylthiophenes. An oxidative photocyclization was then used in the same manner as the previous routes to fuse the rings together to give DNT-1221 derivatives 32-36 in yields of 6-20% (Table 7). |
69% | A stirred and cooled solution of thiophene (185 mL, 2.3 mol) at 0 C in chloroform was treated dropwise with bromine (500 ML, 1560 g, 9.75 mol) for 5 h. During the last hour bromine was added without cooling the reaction mixture. Then the mixture was stirred and heated at reflux for 5 h, cooled to room temperature, quenched with 3 M aqueous NAOH, and stirred vigerously to consume excess bromine. The aqueous layer was separated, the organic phase was washed with water, and then with acetone (150 mL) to remove remaining water. The organic residue was dried and then dissolved at reflux in chloroform (1 L). When cooling, the target tetrabromo- thiophene was precipitated as colorless crystals (693 g, 75%). A solution of this tetrabromo- thiophene (47 g, 0.12 mol) in dry diethyl ether (300 ML) was cooled to 0 C and treated dropwise with butyllithium in hexane (150 ML, 0.24 mol, 1.6 M) for 80-90 min under argon. Then the mixture was stirred for an additional 20 min, and ice water (250 mL) was added carefully with stirring. The organic phase was separated, the aqueous phase extracted twice with ether, and the organic extracts all combined, dried over anhydrous calcium chloride, and concentrated in vacuo. The residue was distilled at 15 MMHG to give 22 g (77%) of 3,4-dibromothiophene. A solution of this 3,4-dibromothiophene (72 g, 33 mL, 0.3 mol) in dry ether (120 mL) was cooled TO-78 C, added to a solution of nBuLi (206 mL, 0.33 mol, 1.6 M) AT-78 C, and stirred for 5 min. A cold - 78 C solution OF DMF (35 mL, 33 g, 0.45 mol) in dry ether (120 mL) was slowly added to the reaction mixture AT-78 C. After 10 min, the cold bath was removed and an aqueous HCI (150 mL, 6N) solution was added carefully, the mixture warmed to 23 C and the aqueous phase separated and washed further with ether. The organic extracts were then combined, washed with saturated aqueous sodium bicarbonate, and the organic partition evaporated. The residue was distilled twice under vacuum to provide pure title compound (40 g, 69%). | |
With n-butyllithium; In diethyl ether; hexane; at -78℃; for 3.25h; | Step 1: Into a 100 mL round bottom flask containing a solution of 3,4-dibromothiophene (4.0 g, 17 mmol) in diethyl ether (50 mL) was added n-butyl lithium in hexane (1 M solution inhexanes, 17 mL, 17 mmol) at -78 C over 15 mm. To this mixture was addedN,Ndimethylformammde and the reaction was stirred for 3 h. The reaction mixture was treated with saturated ammonium chloride solution and extracted with diethyl ether (2 x 50 mL). The combined organics were washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to furnish 4-bromothiophene-3-carbaldehyde as a liquid which was directly taken to the next step without further purification. ?H NMR (CDC13,400 MHz): 9.99 (s, 1H), 8.17 (s, 1H), 7.76 (s, 1H). |
Step 1: Into a 100 mL round bottom flask containing a solution of 3,4-dibromothiophene (4.0 g,17 mmol) in diethyl ether (50 mL) was added n-butyl lithium in hexane (1 M solution in hexanes, 17 mL, 17 mmol) at -78 C over 15 mm. To this mixture was addedN,Ndimethylformamide and the reaction was stirred for 3 h. The reaction mixture was treated with saturated ammonium chloride solution and extracted with diethyl ether (2 x 50 mL). Thecombined organics were washed with water and brine, dried over anhydrous sodium sulfate,filtered and concentrated under reduced pressure to furnish 4-bromothiophene-3-carbaldehyde asa liquid which was directly taken to the next step without further purification. ?H NMR (CDC13,400 MHz): 9.99 (s, 1H), 8.17 (s, 1H), 7.76 (s, 1H). | ||
Step 1: Into a 100 mL round bottom flask containing a solution of 3,4-dibromothiophene (4.0 g, 17 mmol) in diethyl ether (50 mL) was added w-butyl lithium in hexane (1 M solution in hexanes, 17 mL, 17 mmol) at -78 C over 15 min. To this mixture was added NN- dimethylformamide and the reaction was stirred for 3 h. The reaction mixture was treated with saturated ammonium chloride solution and extracted with diethyl ether (2 x 50 mL). The combined organics were washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to furnish 4-bromothiophene-3-carbaldehyde as a liquid which was directly taken to the next step without further purification. 1H NMR (CDCI3, 400 MHz): delta 9.99 (s, 1H), 8.17 (s, 1H), 7.76 (s, 1H). | ||
Step 1: Into a 100 mL round bottom flask containing a solution of 3,4-dibromothiophene (4.0 g, 17 mmol) in diethyl ether (50 mL) was added n-butyl lithium in hexane (1 M solution in hexanes, 17 mL, 17 mmol) at -78 oC over 15 min. To this mixture was added N,N- dimethylformamide and the reaction was stirred for 3 h. The reaction mixture was treated with saturated ammonium chloride solution and extracted with diethyl ether (2 x 50 mL). The combined organics were washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to furnish 4-bromothiophene-3-carbaldehyde as a liquid which was directly taken to the next step without further purification. 1H NMR (CDCl3, 400 MHz): delta 9.99 (s, 1H), 8.17 (s, 1H), 7.76 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.5% | With copper(I) bromide; In methanol; at 70 - 97℃;Inert atmosphere; | 21 g of sodium methoxide and 72 g of methanol were added to a 100 ml four-necked flask (the concentration of sodium methoxide relative to the methanol solvent was 22.6percent by weight based on the total amount of sodium methoxide before the reaction) and dissolved at 70 under an argon atmosphere.After addition of 0.83 g of cuprous bromide, 15 g of 3,4-dibromothiophene was added dropwise, and the reaction solution became colorless transparent to black. After completion of the dropwise addition, 50 g of methanol was distilled off (sodium methoxide to methanol solvent The concentration was 48.8 wtpercent based on the total amount of sodium methoxide before the reaction)The reaction was heated to reflux at 97 .When the reaction was traced by gas chromatography, 3,4-dibromothiophene and 3-bromo-4-methoxythiophene were found to be below the detection limit at the reflux starting time of 5 hours.After water was added to the reaction mixture and the mixture was filtered, the crude product was extracted from toluene, and the toluene layer was washed with water, and then the toluene layer was dried with magnesium sulfate.After the magnesium sulfate was removed by filtration, the toluene layer was concentrated by a rotary evaporator and then subjected to vacuum distillation to obtain 7.28 g (yield: 81.5percent) of 3,4-dimethoxythiophene. The purity of its 3,4-dimethoxythiophene was 98.01percent by gas chromatography.The purity (concentration) by gas chromatography in the present invention was indicated by the area ratio of the peak area obtained by the detection device by FID using Agilent 6890N network GC manufactured by Aglient Technologies. |
60% | With copper(l) iodide; In methanol; at 80℃; for 72h; | Step 3: 3,4-dibromothiophene (10 g, 41.2 mmol) is added to 30 g of a methanol-sodium methoxide solution with a mass percent of 30percent and stirred. Then CuI (1.96 g, 10.3 mmol) is added quickly, and refluxed at 80° C. for 72 hrs. The mixture is cooled to room temperature, to which a saturated NaCl solution is added. The mixture is extracted with ethyl acetate several times, and dried over anhydrous sodium sulfate to remove solvents. The crude is passed through a separation column, to give a oily liquid, 3,4-dimethoxythiophene (compound 3), yield 60percent, purity 95percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | EXAMPLE 1: Synthesis of Chloromethyl-3,4-ethylenedioxythiophene for conversion to EDOT-MEOH:; 1) 3,4-dimethoxythiophene synthesis from 3,4-dibromothiophene for the improved EDOT-MeOH synthesis:; [0084] Sodium methoxide was prepared by slow addition of small cubes of sodium metal (25 g, 1.05 mol) to ice bath cooled anhydrous methanol (600 mL) in a 1 L 3-necked flask equipped with a reflux condenser under a nitrogen blanket. Between additions of the sodium it was covered in kerosene to exclude moisture. After complete dissolution of the sodium, 50 g (0.207 mol) of 3,4- dibromothiophene, 16.5 g (0.207 mol) copper (II) oxide, and 1.37 g (0.00827 mol) potassium iodide was added to the reaction mixture. The reaction was refluxed for three days. The reaction was then cooled to room temperature and filtered through a sintered glass fritted funnel. The resulting solid was rinsed with ether and the filtrate was poured into 500 mL water. The solution was then extracted with ether. The organic fractions were combined and dried with magnesium sulfate. Solvent removal gave a light yellow oil. Vacuum distillation gave 26.2 g of a clear, colorless oil whose structure and purity were confirmed by ^H and ^C NMR and GC-MS. Yield was 88percent of theoretical. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With n-butyllithium; In diethyl ether; water; ethyl acetate; N,N-dimethyl-formamide; | Production Example 102 4-Bromothiophene-3-carboxaldehyde After dissolving 25.2 g of 3,4-dibromothiophene in 300 ml of diethyl ether, the solution was cooled to -78 C. Next, 44.1 ml of n-butyllithium (2.6 M, n-hexane solution) was added dropwise while stirring at below -60 C. After 1 hour, 9.66 ml of N,N-dimethylformamide was added dropwqise at below -60 C. After an additional 45 minutes, water was added to the reaction solution, the temperature was returned to room temperature, and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine in that order and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (14.78 g, 74% yield). 1H-NMR (400 MHz, CDCl3); delta (ppm) 7.36 (1H, d, J=3.6 Hz), 8.15 (1H, d J=3.6 Hz), 9.34 (1H, s). |
2.31 g (29%) | With n-butyllithium; In tetrahydrofuran; N,N-dimethyl-formamide; | EXAMPLE 74 Preparation of N-hydroxy-N-[(4-bromo-thien-3-yl)methyl]urea To a -78 C. stirred solution of 3,4-dibromothiophene (10 g, 41.33 mmole) in THF (25 mL) was added n-BuLi (45.5 mmole, 2.5M in hexanes). The reaction was stirred 5 min. and cannulated into a cold (-78 C.) stirred solution of DMF (4.35 g, 62 mmole) in THF (20 mL). The reaction was allowed to stir overnight at room temperature, poured into dilute HCl and extracted with ethyl acetate. The combined organic layers were washed with water, dried (MgSO4) and concentrated to give a brown oil. Distillation yielded 2.31 g (29%) of 4-bromothien-3-yl carboxaldehyde as a liquid (bp: 65, 0.5 mm Hg). |
With n-butyllithium; In N-methyl-acetamide; hexane; | PREPARATION 12 4-Bromo-3-thenaldehyde 3,4-Dibromothiophene [15 g., 0,062 mole, J. Org. Chem. 36, 2690 (1971)] in 20 ml. of ether was cooled to -70 C. and butyl lithium in hexane (34.8 ml. of 2.1 M, 0.073 mole) added dropwise over 5 minutes. After stirring for 5 minutes at -70 C., the solution was transferred, via nylon tubing under nitrogen pressure, to a solution of dimethylformamide (6.8 g., 0.093 mole) in 35 ml. of ether. The resulting mixture was heated to reflux for 2 hours, cooled to room temperature, washed in sequence with two portions of 1 N hydrochloric acid, one of saturated sodium bicarbonate and one of brine, dried over anhydrous magnesium sulfate, filtered and concentrated to an oil. The oil was twice distilled to yield 4-bromo-3-thenaldehyde (5.7 g., b.p. 81-84 C./0.8 mm., m/e 192/190). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11%; 23.2% | With potassium iodide; copper(II) oxide; In methanol; for 72h;Reflux; | A mixture of 21.78 g 1 (0.09 mol), 150 cm3 methanol, 15 g sodium methylate, 3.6 g KI, and 3.6 g CuO was refluxed for 72 h. After removing methanol via vacuum distillation, the residue was dissolved in ethyl acetate. The mixture was filtered and the filtrate was washed by 100 cm3 x 3 saturated brine and dried over anhydrous sodium sulfate. Ethyl acetate was then removed and the residue was purified on silica column chromatography and 4.02 g (23.2 percent) 3-bromo-4-methoxythiophene (3) and 1.44 g (11 percent) 3,4-dimethoxythiophene (2) was obtained. 3-bromo-4-methoxythiophene: 1H NMR (CDCl3, 400 MHz) ppm: d = 7.18 (d, J = 3.5 Hz, 1H), 6.23 (d, J = 3.5 Hz, 1H), 3.86 (s, CH3O); MS (70 eV): m/z = 192.0 (M+). 3,4-dimethoxythiophene: 1H NMR (CDCl3, 400 MHz) ppm: d = 6.20 (s, 2H), 3.86 (s, 2CH3O); MS (70 eV): m/z = 144.0 (M+). |
Tags: 3,4-Dibromothiophene | Thiophenes | Bromides | Organic Building Blocks | Heterocyclic Building Blocks | 3141-26-2
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H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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