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CAS No. : | 18791-79-2 | MDL No. : | MFCD09042555 |
Formula : | C5H3BrOS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZKLBPUYMTHPNOQ-UHFFFAOYSA-N |
M.W : | 191.05 | Pubchem ID : | 12284894 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 37.41 |
TPSA : | 45.31 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.98 cm/s |
Log Po/w (iLOGP) : | 1.63 |
Log Po/w (XLOGP3) : | 2.09 |
Log Po/w (WLOGP) : | 2.32 |
Log Po/w (MLOGP) : | 1.19 |
Log Po/w (SILICOS-IT) : | 3.38 |
Consensus Log Po/w : | 2.12 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.74 |
Solubility : | 0.35 mg/ml ; 0.00183 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.67 |
Solubility : | 0.407 mg/ml ; 0.00213 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.47 |
Solubility : | 0.647 mg/ml ; 0.00339 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.33 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H317-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
88% | With aluminum (III) chloride; bromine In dichloromethane for 12.17 h; | Thiophene-3-carbaldehyde (6.5 g, 0.06 mol) was dissolved in 200 mL of dichloromethane (dry), and 14 g of aluminum chloride was added. The dark solution was stirred for 10 min and solution of bromine (10 g, 0.066 mol) in 10 mL of dichloromethane was added dropwise over 10 min period. The mixture was stirred for 12 h and poured onto crush-ice. The organic layer was separated and extracted with 2 N HCl, washed by water. The organic phase was dried over anhydrous MgSO4 and reduced solvent. The white liquid product was purified by vacuum distillation, with yield of 88percent (10 g). |
88% | Stage #1: With aluminum (III) chloride In dichloromethane at 0℃; for 2 h; Stage #2: With bromine In dichloromethane at 0 - 40℃; |
Anhydrous aluminum chloride (5.9 g, 44.5 mmol) was added in small portions over a period of 2 h to a solution of thiophene-3-carbaldehyde (2.0 g, 17.8 mmol) in CH2Cl2 (100 mL) maintaining the temperature at 0 °C. Bromine (2.56 g, 16.0 mmol) in CH2Cl2 (50 mL) was then added dropwise to the reaction mixture at 0 °C. The reaction mixture was refluxed at 40 °C for 1 h, quenched with water, and extracted with CH2Cl2. The combined extracts were dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluant 10percent EtOAc in petroleum ether) to give 5-bromothiophene-3-carbaldehyde (3.0 g, yield 88percent). |
64% | With aluminum (III) chloride; bromine In dichloromethane at 20℃; for 6 h; Heating / reflux | AlCl3 (15g, 0.112 mol) was added in portions over 2 h to a solution of thiophene- 3-carboxaldehyde (5g, 0.044 mol) in CH2Cl2 (150 mL) at rt. Br2 (2.13 mL, 0.041 mol) in CH2Cl2 (20 mL) was added drop wise. The mixture was heated at reflux for 6 h, cooled, poured into H2O (250 mL) and extracted with CH2Cl2. The combined extracts were washed with brine, dried (MgSO4), concentrated and distilled to yield the sub-title compound 5.4 g (64percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
413 mg (1.12 mmol) of (17), 270 mg (1.41 mmol) of (16), 216 g (2.57 mmol) Of NaHCO3, 235 mg (0.894 mmol) of PPh3 and 116 mg (0.1 eq.)of Pd2(dba)3 were dissolved in 20 ml of DME and 20 ml of water. The reaction mixture was stirred at 80C for 3 h. The DME was removed and the aqueous layer was acified with 1 M HCl. The aqueous layer was acified with IM HCl and extracted with ethyl acetate. The organic layer was washed with brine and dried over Na2SO4. The product was purified by HPLC to give 99 mg of (18).ESI m/z obs.: 436.1 [M+H] (theor. 436.16) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | In DMF (N,N-dimethyl-formamide); for 3.5h;Heating / reflux; | 7.6 g (85 mmol) of copper(I) cyanide were added to a solution of 13.53 g (70.82 mmol) of 2-bromo-4-formylthiophene in 25 ml of DMF and the reaction mixture was refluxed for 3.5 hours, during which process the suspension, which originally was pale green in color, turned into a black solution. After addition of water, the reaction mixture was extracted repeatedly with ethyl acetate, and the organic phases were combined, washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated under slightly reduced pressure. Treatment of the residue (7 g) with ether resulted in 1.6 g of pure product. The mother liquor together with the crude products from other batches was purified by chromatography. (Silica. gel, methylene chloride/petroleum ether 1:1). In total, 56.5 g of 2-bromo-4-formylthiophene were reacted to give 2-cyano-4-formylthiophene, resulting in 12.6 g of pure product (yield 31%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In DMF (N,N-dimethyl-formamide); at 90℃; for 2.5h; | 0.64 g (3.35 [MMOL)] of 2-bromothiophene-4-carboxaldehyde, 0.117 g (0.1675 [MMOL)] of Pd (PPh3) [2CI2] and 0.032 g (0.1675 mmol) of Cul are introduced, under argon, into a solution of 8 [ML] of DMF and 4 ml of triethylamine and, with stirring, argon gas is passed through for a period of 45 minutes. A solution, saturated with argon, of 0.905 g (5.02 [MMOL)] of 4-fluoro-2- [METHOXY-(PROP-2-YNYLOXY)-BENZENE (EXAMPLE P1)] in DMF is then slowly added dropwise in the course of 1.5 hours at [90C] with stirring. After the addition, stirring is continued for 2 hours. After cooling to [20C,] 90 ml of saturated ammonium chloride solution are added and the resulting mixture is stirred for 15 minutes. The crude product is extracted with ethyl acetate (3 x 50 [MOI),] and the combined organic phases are washed twice with saturated ammonium chloride solution and twice in each case with water and sodium chloride solution, and dried over magnesium sulfate. After evaporation, the crude product obtained is purified by silica gel chromatography (eluant : ethyl acetate/hexane 1/4). The desired title compound is obtained in a yield of 0.230 g (24% of theory) in the form of an orange resin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 90℃; for 4h; | To a solution of 5-BROMO-3-THIOPHENECARBALDEHYDE (D36) (2 g, 10.4 mmol, 1 equiv) in DME (45 ML) and H20 (15 ml) was added tetrakis (TRIPHENYLPHOSPHINE)-PALLADIUM (0) (600 mg, 0.52 mmol, 0.05 equiv), and the suspension was stirred for 10 min. Triethenylboroxin-pyridine complex (prepared according to F. Kerins and D. F. O SHEA in J. Org. Chem, 2002,67, 4968-4971; 2.64 g, 11 mmol, 1.05 equiv) and K2CO3 (1.45 g, 10.5 mmol, 1 equiv) were added and the resulting mixture was stirred at 90C for 4 h, cooled to room temperature and diluted with AcOEt. The organic phase was washed with a saturated NAHC03 aqueous solution, dried over MGS04 and concentrated in vacuo. Purification by flash chromatography on silica gel (iso-hexane/AcOEt : 9/1) gave 5-ethenyl-3-thiophenecarbaldehyde (D37) (660 mg, 100%) of adduct as a pale yellow oil. RT = 2. 38 MIN |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30.7 g (79.5%) | With triethylamine; In tetrahydrofuran; ethyl acetate; | EXAMPLE 142 2-(1-Dodecynyl)-4-thiophenecarboxaldehyde A solution of <strong>[18791-79-2]2-bromo-4-thiophenecarboxaldehyde</strong> (45.3 g), 1-dodecyne (43.4 g), and triethylamine (99 ml), in dry tetrahydrofuran (250 ml) was chilled to 5 C. and degassed under nitrogen. bis(Triphenylphosphine)palladium(II)chloride (1.66 g) and copper(I)iodide (0.23 g) were added to the reaction mixture. The mixture was degassed and stirred overnight, under nitrogen, as it was allowed to warm to room temperature. The precipitate was filtered off, washed with ethyl acetate, and the filtrate was evaporated. Ethyl acetate was added to the residue. The solution was washed with brine, dried over magnesium sulfate, filtered, and the filtrate was concentrated. The residue was chromatographed through a silica gel pad eluding with heptane/1% ethyl acetate. The appropriate fractions were collected and evaporated. The residue and that from a similar reaction on a 0.05 mole scale were combined and distilled to give 30.7 g (79.5%), bp 181-185 C. a0.35 mm Hg. ANALYSIS: Calculated for C17 H24 OS: 73.86%C 8.75%H Found: 73.55%C 8.75%H |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With toluene-4-sulfonic acid; In ethylene glycol; toluene; | 19b. 5-Bromo-3-thiophenecarboxaldehyde ethylene glycol acetal To a solution of 8.5 g of <strong>[18791-79-2]5-bromo-3-thiophenecarboxaldehyde</strong>, from step 19a above, in 150 mL of toluene was added 5 mL of ethylene glycol and 85 mg of p-toluenesulfonic acid. The solution was heated at reflux for 4 hours, and the water of reaction was captured in a Dean-Stark trap. The reaction was cooled to room temperature, diluted with water, made basic with satd NaHCO3 solution, and the mixture was extracted with ether. The ether extract was washed with water and brine, and dried over MgSO4. The solvent was removed to afford 10.12 g (96% yield) of the title product as an oil. NMR (CDCl3) delta;3.98-4.1 (m, 4H), 5.81 (s, 1H), 7,11 (d, 1 H, J=1 Hz), 7.30 (d, 1 H, J=1 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate;tetrakis(triphenylphosphine)palladium (0); In 1,4-dioxane; methanol; water; ethyl acetate; | To a solution of <strong>[18791-79-2]5-bromo-3-thiophenecarbaldehyde</strong> (250 mg, 1.29 mmol) in dioxane (4.5 mL) and H2O (1.5 mL) was added 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxamide (200 mg, 0.43 mmol), potassium carbonate (250 mg, 2.58 mmol) and tetrakis(triphenylphosphine)palladium (0) (56 mg, 0.049 mmol). The reaction was run in the microwave at 150 C. for 20 min. It was then treated with EtOAc and H2O to obtain the crude product. This was then treated with MeOH (10 mL) and the solid was filtered and collected to give 310 mg of the desired title compound. LC/MS: m/z 446.4 (M+H), r.t: 1.94 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With cesium fluoride; In 1,2-dichloro-ethane; at 20℃; for 4h; | This compound was synthesized from <strong>[18791-79-2]5-bromothiophene-3-carbaldehyde</strong> as described in example 88 step 1 (3.0 g, yield 73%) as a yellow liquid. 1H NMR (300 MHz, CDCl3) delta 7.36 (s, 1H), 7.15 (s, 1 H), 5.05 - 5.03 (m, 1H), 3.28 (br s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | A Grignard reagent of 1-(magnesiumbromide) decane, prepared by the reaction of 1-bromodecane (17.3 g, 0.78 mol) with magnesium (5 g, 0.21 mol) in 50 mL of tetrahydrofuran (THF) was added drop wise into solution of <strong>[18791-79-2]5-bromothiophene-3-carbaldehyde</strong> (9.1 g, 0.048 mol) in 150 mL of THF at 0 C. After stirring at room temperature for 10 min, the reaction mixture was treatment with water and 2 N HCl, stirred for 2 h. After evaporation of solvent, the mixture was extracted by dichloromethane. The organic phase was washed with water, dried over anhydrous MgSO4 and removed solvent. The pure product was obtained by a silica gel using a mixed solvent hexane and ethyl acetate (1:20, v/v) as eluent, with yield of 63 % (10 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In tetrahydrofuran; at 0℃; for 0.5h; | General procedure: Thetitled compound was prepared in the same manner as describedfor 11 using 10 instead of 8 in 75% yield as slightlyyellow oil. 1H-NMR (500 MHz, DMSO-d6) delta: 7.29 (s, 1H), 7.26(d, J=8.0 Hz, 2H), 7.15 (d, J=8.0 Hz, 2H), 7.01 (s, 1H), 5.86 (d,J=4.5 Hz, 1H), 5.63 (d, J=4.3 Hz, 1H), 2.57 (q, J=7.7 Hz, 2H),1.16 (t, J=7.5 Hz, 3H). MS (APCI, m/z) 279/281 (M+ H-H2O). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.01 g | To a suspension of lithium chloride (174 mg) andacetonitrile (15 mL) were added 5-bromothiophene-3- carbaldehyde (770 mg) and ethyl diethylphosphonoacetate (0.840 mL) at 0C, and the mixture was stirred at 0C for 10 min. To the reaction mixture was added 1, 8-diazabicyclo [5.4.0] undec-7- ene (0.638 mL) , and the mixture was stirred at roomtemperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel columnchromatography (hexane/ethyl acetate) to give the titlecompound (1.01 g) . NMR (300 MHz, DMSO-de) delta 1.19-1.29 (3H, m) , 4.11-4.23 (2H, m) , 6.48 (1H, d, J = 15.90 Hz), 7.53 (1H, d, J = 15.0 Hz), 7.74 (1H, d, J = 1.51 Hz), 7.98 (1H, d, J = 1.51 Hz). |
Tags: 18791-79-2 synthesis path| 18791-79-2 SDS| 18791-79-2 COA| 18791-79-2 purity| 18791-79-2 application| 18791-79-2 NMR| 18791-79-2 COA| 18791-79-2 structure
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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 |
Sorry,this product has been discontinued.
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