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CAS No. : | 262373-15-9 | MDL No. : | MFCD10566914 |
Formula : | C11H15F3O3SSi | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SKLVYEYSGSTOFD-UHFFFAOYSA-N |
M.W : | 312.38 | Pubchem ID : | 11449792 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P234-P260-P264-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P390-P405-P406-P501 | UN#: | 3265 |
Hazard Statements: | H290-H314 | Packing Group: | Ⅱ |
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 |
---|---|---|
With cesium fluoride In tetrahydrofuran at 90℃; for 24h; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrabutylammonium triphenyldifluorosilicate; In toluene; at 50℃; for 24h; | General procedure: A mixture of 1a (34 mg, 0.250 mmol), 2a (149 mg, 0.500 mmol) and TBAT (540 mg, 1.00 mmol) in toluene (3 mL) was stirred at 50 C for 18 h. After this time, the reaction mixture was cooled to ambient temperature and concentrated under reduced pressure. The residue obtained was purified by flash chromatography (silica, heptane to 2:3 ethyl acetate/heptane) to afford 3a (45 mg, 85%) as an off-white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,2,6,6-tetramethyl-piperidine; 1-iodo-2-phenylethyne; cesium fluoride In acetonitrile at 50℃; for 5h; Overall yield = 61 %; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium fluoride; 18-crown-6 ether; ammonium bicarbonate; In tetrahydrofuran; at 60℃; for 12h;Inert atmosphere; | General procedure: f1e To a flame-dried screw-capped tube equipped with a magnetic stirN - bar were added 18-crown-6 (0.3 17 g, 1.2 mmol), KF (0.070 g, 1.2I .- 29 mmol) and NH4HCO3 (0.040 g, 0.50, mmol).Then the screw-capped tube was evacuated and backfilled with argon. Themixture was dissolved in THF (2.0 mL) under argon atmosphere and then to thestirring solution were added the N, N-dimethylaniline 1 (0.06 1 g, 65 ML, 0.50 mmol)and 2-(trimethylsilyl) phenyltrifluoro-methanesulfonate 2 (0.179 g, 146 pL, 0.60mmol) at room temperature (27C). Then the screw-capped tube kept in a preheatedoil bath at 60 C for 12 h. The reaction mixture cooled and the residue on column chromatography afforded N-methyl-N-phenylaniline 3 as a colourless oil (0.087 g, 95%),Rj(Pet. ether/DCM 90/10): 0.66; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium diacetate; caesium carbonate; triphenylphosphine; cesium fluoride; copper dichloride; In toluene; acetonitrile; at 80℃; for 36h;Inert atmosphere; | General procedure: Under nitrogen atmosphere, CsF (1.2 mmol, 182.3 mg) and Cs2CO3 (0.6 mmol, 195.5mg) were added at room temperature to a solution of 1 (0.3 mmol), 2 (0.6 mmol),Pd(OAc)2 (0.024 mmol, 5.4 mg), PPh3 (0.048 mmol, 12.6 mg) and CuCl2 (0.63 mmol,84.7 mg) in a mixed solvent of anhydrous MeCN (0.9 mL) and anhydrous toluene (2.7mL). The reaction mixture was stirred at 80 oC for 36 h. When the reaction wascomplete (as evidenced by TLC), the reaction mixture was filtered through a layer ofsilica gel and eluted with Et2O. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (3i-k: petroleum ether/ethyl acetate = 20:1; other compounds: petroleum ether/ethyl acetate = 10:1) to afford 3. | |
With palladium diacetate; caesium carbonate; triphenylphosphine; cesium fluoride; copper dichloride; In toluene; acetonitrile; at 20 - 80℃; for 36h;Inert atmosphere; | General procedure: Under nitrogen atmosphere, CsF (1.2 mmol, 182.3 mg) and Cs2CO3 (0.6 mmol, 195.5mg) were added at room temperature to a solution of 1 (0.3 mmol), 2 (0.6 mmol),Pd(OAc)2 (0.024 mmol, 5.4 mg), PPh3 (0.048 mmol, 12.6 mg) and CuCl2 (0.63 mmol,84.7 mg) in a mixed solvent of anhydrous MeCN (0.9 mL) and anhydrous toluene (2.7mL). The reaction mixture was stirred at 80 oC for 36 h. When the reaction wascomplete (as evidenced by TLC), the reaction mixture was filtered through a layer ofsilica gel and eluted with Et2O. The filtrate was concentrated under reduced pressure,and the residue was purified by column chromatography on silica gel (3i-k: petroleumether/ethyl acetate = 20:1; other compounds: petroleum ether/ethyl acetate = 10:1) toafford 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | General procedure: A round bottomed flask was charged with the münchnone precursor 6-9 (3equiv), silyltriflate (1equiv), and MeCN under nitrogen. DIPC (3equiv) was added via syringe and the mixture stirred 5-10min. The fluoride source-all yields below use CsF-(2.5equiv) was added and the mixture stirred 12-24h until the silyltriflate was consumed. The reaction mixture was concentrated and purified directly by flash chromatography (silica gel, 0-10% ethyl acetate in pentane) to afford the isoindole. Note the CsF was oven-dried overnight (>120C) prior to use. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (triphenylphosphine)gold(I) chloride; cesium fluoride; In acetonitrile; at 20℃; for 12h;Inert atmosphere;Catalytic behavior; | General procedure: To a solution of Kobayashi's silylaryl triflate 1 (0.60 mmol) in anhydrous acetonitrile (3.0 mL), catalytic PPh3AuCl (32 mg, 0.060 mmol) and CsF (182 mg, 1.2 mmol) were added. The mixture was stirred at 60 C or room temperature for 6 h or 12 h. After removal of the solvent, the residue was then purified by flash column chromatography on silica gel (eluent = hexanes/ethyl acetate 40:1 v/v) to give the desired triphenylene 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With bis(η3-allyl-μ-chloropalladium(II)); tri-tert-butyl phosphine; tetramethylammonium bromide; lithium ethoxide; In toluene; at 120℃; for 24h;Inert atmosphere; | Under a nitrogen atmosphere, 1 mmol of 2- (trimethylsilyl) -4-methylphenyltrifluoromethanesulfonate, 1.5 mmol of diphenylacetylene, 0.025 mmol of allyl chloride Palladium dimer, 0.1 mmol of tri-t-butylphosphine, 1 mmol of lithium ethoxide, 1 mmol of tetramethylammonium bromide and 5 mL of toluene solvent.The reaction temperature was constant at 120 C for 24 hours using an oil bath.After cooling, the filtrate was concentrated and the filtrate was concentrated to give the crude product.The crude product was separated on a silica gel column and eluted with petroleum ether to give 183 mg of 1,1-dimethyl-3,4-diphenyl-6-methylbenzothiazole (purity> 98%, light yellow Solid), the isolated yield was 56%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Kobayashi silylaryl triflate 1 (0.68 mmol) and aliphatic carboxylic acid 2 (3.4 mmol) in acetonitrile(4.0 mL) was added sodium hydroxide (80 mg, 2.0 mmol) under nitrogen atmosphere. After stirringfor 10 minutes at room temperature, cesium fluoride (410 mg, 2.7 mmol) was then introduced. Themixture was stirred at 80 oC for 4 h. After removal of the solvent, the residue was then purified byflash column chromatography on silica gel (eluent = petroleum ether/ethyl acetate 10:1 v/v) to givethe desired product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With cesium fluoride; In tetrahydrofuran;Inert atmosphere; Reflux; | General procedure: CsF (45 mg, 0.3 mmol) and aryne precursor 2a(44.7 mg, 0.15 mmol) were added to a solution of 2-tirfluoroacetylphenol 1a (19 mg, 0.1 mmol) in dry THF (1.0 mL) under nitrogen. After addition, the resulting mixture was stirred in refluxing THF until full consumption of the starting 2-tirfluoroacetylphenol indicated by TLC. The solvent was removed under reduced pressure and the crude material was purified by column chromatography (PE-EtOAc, 10:1) to afford the pure desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 15-crown-5; cesium fluoride; <i>tert</i>-butyl alcohol In acetonitrile at 40℃; for 3h; Inert atmosphere; Overall yield = 57 %; Overall yield = 12.8 mg; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With 18-crown-6 ether; caesium carbonate; In tetrahydrofuran; at 25℃; for 24h;Inert atmosphere; | General procedure: To a mixture of 2-(trimethylsilyl)phenyl triflate (1a, 150 mg, 0.503 mmol) and benzyl azide (2, 333 mg,2.50 mmol) dissolved in tetrahydrofuran (2.5 mL) was added cesium carbonate (326 mg, 1.00 mmol)and 18-crown-6-ether (265 mg, 1.00 mmol) at room temperature. After stirring for 24 h at 25 C, water(10 mL) was added to the mixture. The mixture was then extracted with ethyl acetate (15 mL × 3), andthe combined organic extract was washed with brine (10 mL), dried (Na2SO4), and, after filtration, thefiltrate was concentrated under reduced pressure. The residue was purified by column chromatography(silica-gel 10 g, n-hexane/EtOAc = 5/1) to give 1-benzyl-1H-benzo[d][1,2,3]triazole (3, 90.0 mg,0.431 mmol, 85.6%) as a colorless solid. |
Tags: 262373-15-9 synthesis path| 262373-15-9 SDS| 262373-15-9 COA| 262373-15-9 purity| 262373-15-9 application| 262373-15-9 NMR| 262373-15-9 COA| 262373-15-9 structure
[ 88284-48-4 ]
2-(Trimethylsilyl)phenyl trifluoromethanesulfonate
Similarity: 0.91
[ 780820-43-1 ]
3-(Trimethylsilyl)-2-naphthyl Trifluoromethanesulfonate
Similarity: 0.89
[ 556812-41-0 ]
4-Methoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate
Similarity: 0.85
[ 866252-52-0 ]
4,5-Dimethoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate
Similarity: 0.81
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Code | Phrase |
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P222 | Do not allow contact with air. |
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P230 | Keep wetted |
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P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
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Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
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P306 | IF ON CLOTHING: |
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P322 | |
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P350 | Gently wash with plenty of soap and water. |
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P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
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P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
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P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
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P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
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Disposal | |
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Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
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H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
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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