Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 201037-95-8 | MDL No. : | MFCD30471718 |
Formula : | C12H28O4Si | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JDGGOIGZHUWNHX-UHFFFAOYSA-N |
M.W : | 264.43 | Pubchem ID : | 24179562 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
100% | Stage #1: 2,2'-[1,2-ethanediylbis(oxy)]bisethanol With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.666667h; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; mineral oil at 20℃; for 23h; | 64 Production of triethylene glycol mono-tert-butyldimethylsilyl ether Triethylene glycol (2.2 mL, 16.5 mmol) was added to a solution of 60% sodium hydride (713 mg, 17.8 mmol)in tetrahydrofuran (88 mL) at 0°C and stilled at room temperature for 40 minutes. To this solution, tert-butyldimethylchlorosilane(2.74g, 18.2 mmol) was added, stirred at room temperature for 23 hours, then water was added, andextraction was carried out with dichloromethane. The organic layer was dried with anhydrous sodium sulfate, then thesolvent was distilled away under a reduced pressure to obtain the title compound (4.19 g, quant.) as a pale yellow oilymatter.1H NMR (400 MHz, CDCl3) δ 3.79-3.72 (4H, m), 3.67-3.54 (8H, m), 0.90 (9H, s), 0.07 (6H, s). |
84% | With pyridine; dmap at 20℃; | 4.4. General procedure for the synthesis of TBDMS-protected and mesylated ethylene glycol linkers General procedure: To a solution of ethylene glycol (19, 20, 21 or 22) (8-10 equiv) and DMAP (cat.) in dry pyridine (5 mL) was added TBDMS-Cl (1 equiv). The reaction mixture was stirred at room temperature overnight and then diluted with CH2Cl2 before the organic phase was washed twice with 1 M HCl, once with H2O and then satd NaHCO3. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure. The TBDMS-protected ethylene glycols (23, 24, 25 or 26) were used without further purification. |
80.2% | With dmap In dichloromethane at 0 - 20℃; for 4h; | 28 Example 28: N-methyl-2-((3-((E)-2-(2-pyridyl)vinyl)-1-(2-(2-(2-hydroxyethoxy)ethoxy (Yl)ethoxycarbonyl)-1H-indazol-6-yl)thio)benzamide hydrochloride (compound 50) To the reaction flask was sequentially added triethylene glycol (5.0g, 33.0mmol, 5.0eq.), DCM (10mL), DMAP (0.16g, 1.3mmol, 0.2eq.), TEA (0.67g, 6.6mmol, 1.0eq.) ) And DCM (10 mL), the reaction system was cooled to 0° C., and then a solution of TBSCl (1.0 g, 6.6 mmol, 1.0 eq.) in DCM (2.5 mL) was added dropwise. Subsequently, the reaction system was warmed to room temperature, and the reaction was continued at room temperature for 4 hours. Then, the reaction mixture was washed once with saturated ammonium chloride solution and saturated brine (30 mL each). The organic layer was separated and concentrated to obtain the product 3,6,9-trioxa-10-sila-10,10,11,11-tetramethyldodecan-1-ol (1.4g, 80.2%) . |
80.2% | With dmap; triethylamine In dichloromethane at 0 - 20℃; for 4h; | 29 [00161] Example 29: Synthesis of N-methyl-2-((1-(2-(2-(2- hydrosxyethoxy)ethoxy)ethoxcarbonyl) -3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6- yl)thio)benzamide hydrochloride (compound 50). [00162] In a flask were added triethylene glycol (5.0 g, 33.0 mmol, 5.0 eq.), DCM (10 mL), DMAP (0.16 g, 1.3 mmol, 0.2 eq.), TEA (0.67 g, 6.6 mmol, 1.0 eq.), and DCM (10 mL). The mixture was cooled to 0 °C, followed by dropwise addition of a solution of TBSC1 (1.0 g, 6.6 mmol, 1.0 eq.) in DCM (2.5 mL). The reaction temperature was raised to rt; and the mixture was stirred at rt for 4 h. The mixture was then washed with saturated ammonium chloride solution (30 mL) and with brine (30 mL), subsequently. The organic layer was concentrated to dryness, providing 10,10,11,11-tetramethyl-3, 6,9- trioxa-10-siladodecan-1-ol (1.4 g, 80.2%). |
73% | With pyridine In dichloromethane at 20℃; | |
64% | With dmap; triethylamine In dichloromethane at 20℃; for 3h; Inert atmosphere; | |
55% | With sodium hydride In tetrahydrofuran at 20℃; for 1h; | |
52% | With 1H-imidazole In dichloromethane at 20℃; for 17h; | j00710j 2,2,3,3-Tetramethyl-4,7,1 0-trioxa-3-siladodecan-12-ol (2): 1007111 A solution of 2,2’-(ethane-1,2-diylbis(oxy))bis(ethan-1-ol) (15 g, 99.5 mmol) inDCM (150 mL) at 0 °C was charged with imidazole (4.7 g, 69.6 mmol), TBDMS chloride (10.5 g, 69.6 mmol) and stirred at 0°C for 1 h. The resulting solution was warmed to room temperature and stirred for 16 h. The reaction mixture was partition between with H20 (100 mL) and DCM (100 mL) and the separated organic layer was washed with 10% aqueous HC1 solution, saturated sodium bicarbonate and brine. The combined organic layers were dried overanhydrous Na2SO4, filtered and concentrated in vacuo resulting in a crude compound which was purified by chromatography on silica gel, eluting with 2-4% methanol in DCMto gvie 13.8 g, 52% yield of the title compound as a light yellow oil. ‘H NMR (400 MHz, DMSO-d6): ö = 5.22 (s, 1H), 4.51 (t, J= 5.51 Hz, 2H), 3.64 (d, J= 4.41 Hz, 4H), 3.43 -3.53 (m, 6H), 0.82 (s, 9H), 0.08 (s, 6H). |
51% | With dmap; triethylamine In dichloromethane at 0 - 25℃; Inert atmosphere; | |
50% | With triethylamine In dichloromethane | |
48% | With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 16h; | |
28% | With 1H-imidazole In dichloromethane at 0 - 20℃; for 10h; | 23.A1 2,2,3,3-tetramethyl-4,7,10-trioxa-3-siladodecan-12-ol (23-2B 1): To a stirred solution of 23-1 (20 g, 133.33 mmol) in dichlorome thane (100 mL) was added imidazole (5.4 g, 79.99 mmol) and TBDMSC1 (10.0 g g, 66.66 mmol) at 0 °C and stirred to RT for 10 hr. The reaction mixture was diluted with DCM (200 mL) and washed with water (2 X 100 mL) and brine (50 mL). The organic layer was concentrated under reduced pressure and the crude residue was purified by flash column chromatography (100-200 silica) using 20% ethyl acetate/pet. ether gave 23-2B1 (10 g, 37.87 mmol, 28% yield) as a colorless liquid. |
17% | With triethylamine In hexane; acetonitrile at 20℃; for 24h; Inert atmosphere; | Typical procedure for the monosilylation of symmetric diols General procedure: In a flame-dried100 mL round-bottom flask equipped with a teflon magnetic stir bar,diol(5.0 mmol) was added to acetonitrile (12.5 mL) and hexanes (37.5 mL).Triethylamine (Et3N, 0.84 mL, 6.00 mmol, 1.2 equiv) and tertbutyldimethylsilylchloride (TBSCl, 0.53 g, 5.0 mmol, 1.0 equiv) were addedto the solution and the resulting biphasic mixture was stirred vigorously atroom temperature for 24 h under a N2 atmosphere. The reaction was quenchedwith saturated aqueous ammonium chloride (NH4Cl, 50 mL), and extractedwith ethyl acetate (EtOAc, 3 50 mL). The combined organic phase waswashed with brine (3 50 mL) and dried over anhydrous sodium sulfate(Na2SO4). The crude product was purified by silica gel column chromatography(10-15% EtOAc/hexanes). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With sodium hydride In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With triethylamine In diethyl ether at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / triphenylphosphine; diethyl azodicarboxylate / toluene; tetrahydrofuran / 0.33 h / 20 °C 2: 69 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 85 percent / triphenylphosphine; diethyl azodicarboxylate / toluene; tetrahydrofuran / 0.33 h / 20 °C 2: 69 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3: triethylamine / CH2Cl2 / 0.17 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 85 percent / triphenylphosphine; diethyl azodicarboxylate / toluene; tetrahydrofuran / 0.33 h / 20 °C 2: 69 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3: triethylamine / CH2Cl2 / 0.17 h / 20 °C 4: 3.15 g / sodium azide; tetra-n-butylammonium iodide / dimethylformamide / 1 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 85 percent / triphenylphosphine; diethyl azodicarboxylate / toluene; tetrahydrofuran / 0.33 h / 20 °C 2.1: 69 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3.1: triethylamine / CH2Cl2 / 0.17 h / 20 °C 4.1: 3.15 g / sodium azide; tetra-n-butylammonium iodide / dimethylformamide / 1 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; H2O / 1 h / 20 °C 5.2: 53 percent / sodium carbonate / tetrahydrofuran; H2O / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 85 percent / triphenylphosphine; diethyl azodicarboxylate / toluene; tetrahydrofuran / 0.33 h / 20 °C 2.1: 69 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3.1: triethylamine / CH2Cl2 / 0.17 h / 20 °C 4.1: 3.15 g / sodium azide; tetra-n-butylammonium iodide / dimethylformamide / 1 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; H2O / 1 h / 20 °C 5.2: 53 percent / sodium carbonate / tetrahydrofuran; H2O / 1 h / 20 °C 6.1: 980 mg / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran; toluene / 0.17 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: 85 percent / triphenylphosphine; diethyl azodicarboxylate / toluene; tetrahydrofuran / 0.33 h / 20 °C 2.1: 69 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3.1: triethylamine / CH2Cl2 / 0.17 h / 20 °C 4.1: 3.15 g / sodium azide; tetra-n-butylammonium iodide / dimethylformamide / 1 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; H2O / 1 h / 20 °C 5.2: 53 percent / sodium carbonate / tetrahydrofuran; H2O / 1 h / 20 °C 6.1: 980 mg / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran; toluene / 0.17 h / 20 °C 7.1: trifluoroacetic acid / CH2Cl2 / 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: 85 percent / triphenylphosphine; diethyl azodicarboxylate / toluene; tetrahydrofuran / 0.33 h / 20 °C 2.1: 69 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3.1: triethylamine / CH2Cl2 / 0.17 h / 20 °C 4.1: 3.15 g / sodium azide; tetra-n-butylammonium iodide / dimethylformamide / 1 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; H2O / 1 h / 20 °C 5.2: 53 percent / sodium carbonate / tetrahydrofuran; H2O / 1 h / 20 °C 6.1: 980 mg / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran; toluene / 0.17 h / 20 °C 7.1: trifluoroacetic acid / CH2Cl2 / 1 h / 0 °C 8.1: 1.09 g / triethylamine / dimethylformamide / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: 85 percent / triphenylphosphine; diethyl azodicarboxylate / toluene; tetrahydrofuran / 0.33 h / 20 °C 2.1: 69 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3.1: triethylamine / CH2Cl2 / 0.17 h / 20 °C 4.1: 3.15 g / sodium azide; tetra-n-butylammonium iodide / dimethylformamide / 1 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; H2O / 1 h / 20 °C 5.2: 53 percent / sodium carbonate / tetrahydrofuran; H2O / 1 h / 20 °C 6.1: 980 mg / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran; toluene / 0.17 h / 20 °C 7.1: trifluoroacetic acid / CH2Cl2 / 1 h / 0 °C 8.1: 1.09 g / triethylamine / dimethylformamide / 2 h / 20 °C 9.1: 52 percent / cesium carbonate; benzenethiol / acetonitrile / 0.5 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1.1: 85 percent / triphenylphosphine; diethyl azodicarboxylate / toluene; tetrahydrofuran / 0.33 h / 20 °C 2.1: 69 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3.1: triethylamine / CH2Cl2 / 0.17 h / 20 °C 4.1: 3.15 g / sodium azide; tetra-n-butylammonium iodide / dimethylformamide / 1 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; H2O / 1 h / 20 °C 5.2: 53 percent / sodium carbonate / tetrahydrofuran; H2O / 1 h / 20 °C 6.1: 980 mg / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran; toluene / 0.17 h / 20 °C 7.1: trifluoroacetic acid / CH2Cl2 / 1 h / 0 °C 8.1: 1.09 g / triethylamine / dimethylformamide / 2 h / 20 °C 9.1: 52 percent / cesium carbonate; benzenethiol / acetonitrile / 0.5 h / 50 °C 10.1: diisopropylethylamine; 4-dimethylaminopyridine; resin / dimethylformamide / 72 h / 20 °C 10.2: triethylamine; benzenethiol / tin(II) chloride / tetrahydrofuran / 5 h / 20 °C 10.3: CH2Cl2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1.1: 85 percent / triphenylphosphine; diethyl azodicarboxylate / toluene; tetrahydrofuran / 0.33 h / 20 °C 2.1: 69 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3.1: triethylamine / CH2Cl2 / 0.17 h / 20 °C 4.1: 3.15 g / sodium azide; tetra-n-butylammonium iodide / dimethylformamide / 1 h / 80 °C 5.1: triphenylphosphine / tetrahydrofuran; H2O / 1 h / 20 °C 5.2: 53 percent / sodium carbonate / tetrahydrofuran; H2O / 1 h / 20 °C 6.1: 980 mg / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran; toluene / 0.17 h / 20 °C 7.1: trifluoroacetic acid / CH2Cl2 / 1 h / 0 °C 8.1: 1.09 g / triethylamine / dimethylformamide / 2 h / 20 °C 9.1: 52 percent / cesium carbonate; benzenethiol / acetonitrile / 0.5 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 70 percent / NaH / tetrahydrofuran 2: 79 percent / TBAF / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 70 percent / NaH / tetrahydrofuran 2.1: 79 percent / TBAF / tetrahydrofuran 3.1: Bu3SnH; AIBN / benzene 3.2: I2 / CH2Cl2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 70 percent / NaH / tetrahydrofuran 2.1: 79 percent / TBAF / tetrahydrofuran 3.1: Bu3SnH; AIBN / benzene 3.2: I2 / CH2Cl2 4.1: 80 percent / DCC; DMAP / CH2Cl2 / sonication |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 70 percent / NaH / tetrahydrofuran 2.1: 79 percent / TBAF / tetrahydrofuran 3.1: Bu3SnH; AIBN / benzene 3.2: I2 / CH2Cl2 4.1: 80 percent / DCC; DMAP / CH2Cl2 / sonication 5.1: 38 percent / Et3N; PdCl2(PPh3)2; CuI / tetrahydrofuran / 3.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With triethylamine In dichloromethane at 0 - 20℃; for 22h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With N-Trimethylamine hydrochloride; triethylamine In acetonitrile at 0℃; for 12h; Inert atmosphere; | |
66% | With triethylamine In dichloromethane at 20℃; for 15h; | 21 Compound 30c (1 g, 3.78 mmol), p-toluenesulfonyl chloride (865.6 mg, 4.54 mmol), triethylamine (459.4 mg, 4.54 mmol) were dissolved in dichloromethane (15 mL), and the reaction system was stirred at room temperature for 15 hours , 30 mL of water was added to quench the reaction, extracted with dichloromethane, the organic phase was collected, dried, concentrated, and subjected to column chromatography (petroleum ether: ethyl acetate = 10: 1 to 5: 1) to obtain the product (colorless oil, product rate: 66.8%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With triethylamine In diethyl ether at 0 - 20℃; for 1h; | 4.4. General procedure for the synthesis of TBDMS-protected and mesylated ethylene glycol linkers General procedure: To a cooled solution (0 °C) of TBDMS-protected ethylene glycol (23, 24, 25 or 26) (1 equiv) in dry Et2O (5-7 mL) was added dry Et3N (2 equiv) followed by dropwise addition of MsCl (1.5 equiv). The reaction mixture was stirred at 0 °C to room temperature for 1 h and then diluted with CH2Cl2. The organic phase was washed with mildly acidic H2O, H2O and satd NaCO3, and dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography. |
85% | With triethylamine In dichloromethane at 0 - 20℃; for 2h; | 23.A2 2,2,3,3-tetramethyl-4,7,1O-trioxa-3-siladodecan-12-ylmethanesulfonate (23-2B2). Methane sulfonyl chloride (1.5 mL, 18.93 mmol) and triethylamine (3.2 mL, 22.72 mmol) were added to a solution of 23-2B1 (5 g, 18.93 mmol) in DCM (100 mL) at 0 °C and stirred at RT for 2 hr. Reaction mixture diluted with water (25 mL), extracted with DCM (3 X 25 mL). The combined organic layers were washed with saturated NaHC03 solution (10 mL), brine (25 mL), dried over sodium Na2S04 and concentrated. This crude compound was purified flash column chromatography (100-200 silica) using 15% EtOAc/hexanes to afford 23-2B2 (1.1 g, 3.21 mmol, 85% yield) as a colorless liquid. |
47% | With triethylamine In dichloromethane at 20℃; for 2h; | 1007081 2,2,3,3-Tetramethyl-4,7,1 0-trioxa-3-siladodecan-12-yl methanesulfonate (3): j007091 A solution of 2,2,3 ,3-tetramethyl-4,7, 1 0-trioxa-3 -siladodecan- 1 2-ol (13.8 g, 52.2 mmol) in DCM (100 mL) at 0 °C was charged with triethyl amine (21.7 mL, 156.4 mmol) andmethane sulphonyl chloride (4.4 mL, 57.4 mmol) and stirred at room temperature for 2 h. The reaction mixture was diluted with H20 (30 mL) and extracted with ethyl acetate (3 X 30 mL) and separated. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo resulting in a crude compound which was purified by chromatography on silica gel, eluting with 2-4% methanol in DCM to give 8 g, 47% yield of the title compoundas yellow oil. ‘H NMR (400 MHz, DMSO-d6): ö = 4.26 (dd, J= 3.47, 5.32 Hz, 2H), 3.61 -3.66 (m, 4H), 3.51 (s, 4H), 3.41 (t, J= 5.09 Hz, 2H), 3.13 (s, 3H), 0.82 (s, 9H), 0.00 (s, 6H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / diethyl ether / 1 h / 0 - 20 °C 2: sodium hydride / N,N-dimethyl-formamide / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triethylamine / diethyl ether / 1 h / 0 - 20 °C 2: sodium hydride / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3: triethylamine tris(hydrogen fluoride) / dichloromethane / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-(2-(2-(tert-butyl-dimethyl-silanyloxy)-ethoxy)-ethoxy)-ethanol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 1.5h; Inert atmosphere; Stage #2: With triethylamine In dichloromethane at -78 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 2.1: sodium hydroxide; benzyltrimethylammonium chloride / methanol; dichloromethane / -20 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 2.1: sodium hydroxide; benzyltrimethylammonium chloride / methanol; dichloromethane / -20 - 20 °C 3.1: ammonium fluoride / methanol / 8 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 2.1: sodium hydroxide; benzyltrimethylammonium chloride / methanol; dichloromethane / -20 - 20 °C 3.1: ammonium fluoride / methanol / 8 h / Reflux 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 12 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 2.1: sodium hydroxide; benzyltrimethylammonium chloride / methanol; dichloromethane / -20 - 20 °C 3.1: ammonium fluoride / methanol / 8 h / Reflux 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 12 h / 0 - 20 °C 5.1: palladium complex of polymer bound phosphine ligand / tetrahydrofuran / 15 h / 50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: triethylamine / dichloromethane / 2 h / 20 °C 2.1: sodium hydride; t-butyl bromide / tetrahydrofuran / 16 h / 20 °C / Molecular sieve 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 4.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C 5.1: sodium azide / ethanol / 12 h / 20 °C 6.1: triphenylphosphine / tetrahydrofuran; water / 16 h / 20 °C 7.1: HATU; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 0.17 h / 20 °C 7.2: 2 h / 20 °C 8.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: triethylamine / dichloromethane / 2 h / 20 °C 2.1: sodium hydride; t-butyl bromide / tetrahydrofuran / 16 h / 20 °C / Molecular sieve 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 4.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C 5.1: sodium azide / ethanol / 12 h / 20 °C 6.1: triphenylphosphine / tetrahydrofuran; water / 16 h / 20 °C 7.1: HATU; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 0.17 h / 20 °C 7.2: 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: triethylamine / dichloromethane / 2 h / 20 °C 2: sodium hydride; t-butyl bromide / tetrahydrofuran / 16 h / 20 °C / Molecular sieve 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 4: triethylamine / dichloromethane / 16 h / 0 - 20 °C 5: sodium azide / ethanol / 12 h / 20 °C 6: triphenylphosphine / tetrahydrofuran; water / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: triethylamine / dichloromethane / 2 h / 20 °C 2: sodium hydride; t-butyl bromide / tetrahydrofuran / 16 h / 20 °C / Molecular sieve 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 4: triethylamine / dichloromethane / 16 h / 0 - 20 °C 5: sodium azide / ethanol / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 2 h / 20 °C 2: sodium hydride; t-butyl bromide / tetrahydrofuran / 16 h / 20 °C / Molecular sieve 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 4: triethylamine / dichloromethane / 16 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 2 h / 20 °C 2: sodium hydride; t-butyl bromide / tetrahydrofuran / 16 h / 20 °C / Molecular sieve 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 2 h / 20 °C 2: sodium hydride; t-butyl bromide / tetrahydrofuran / 16 h / 20 °C / Molecular sieve |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 20 °C 2.1: hydrazine hydrate / ethanol / Reflux 2.2: 2 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 20 °C 2.1: hydrazine hydrate / ethanol / Reflux 2.2: 2 h / Reflux 3.1: tetrahydrofuran / 3 h / 20 °C 3.2: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; | 65 Production of 2-(2,2,3,3-tetramethyl-4,7,10-trioxa-3-siladodecan-12-yl)isoindoline-1,3-dione Triethyleneglycol mono-tert-butyldimethylsilyl ether (1.3 g, 4.92 mmol) and diethylazodicarboxylate (2.2 mol/L,toluene solution) (2.4 mL, 5.3 mmol) were added to a solution of phthalimide (1.15 g, 7.82 mmol) and triphenylphosphine(2.06 g, 7.85 mmol) in tetrahydrofuran (50 mL) at room temperature, and stirred overnight. Further ethanol (20 mL) wasadded, stirred at room temperature for 30 minutes, and then the solvent was distilled away under a reduced pressure.To the residue, ethyl acetate (12.5 mL) and hexane (12.5 mL) were added, and insolubles were filtered off. The filtratewas concentrated under a reduced pressure, and then the residue was purified by silica gel column chromatography(hexane/ethyl acetate (v/v) = 5/95 → 0/100) to obtain the title compound (822 mg, 42%) as a colorless oily matter.1H NMR (400 MHz, CDCl3) δ 7.84 (2H, dd, J = 5.2, 3.2 Hz), 7.71 (2H, dd, J = 5.2, 3.2 Hz), 3.90 (2H, t, J = 6.0 Hz), 3.74(2H, t, J = 6. Hz), 3.70 (2H, t, J = 5.6 Hz), 3.65-3.59 (4H, m), 3.50 (2H, t, J = 5.6 Hz), 0.87 (s, 9H), 0.04 (s, 6H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70.3% | With triethylamine In dichloromethane at 0 - 20℃; for 3h; | 28 Add 3,6,9-trioxa-10-sila-10,10,11,11-tetramethyldodecane-1-ol (1.4g, 5.3mmol, 1.0eq.) into the reaction flask, DCM (15mL) and TEA (0.64g, 6.4mmol, 1.2eq.), the reaction system was cooled to 0°C, and then 4-nitrophenyl chloroformate (1.2g, 5.8mmol, 1.1eq.) was added dropwise DCM (6mL) solution. The reaction temperature was raised to room temperature, and the reaction was allowed to continue at room temperature for 3 hours. Then the reaction mixture was directly stirred into silica gel, and then separated and purified with a silica gel column (petroleum ether: ethyl acetate = 100:0 to 100:20) to obtain (4-nitrophenyl) (3,6,9-trioxane) Hetero-10-sila-10,10,11,11-tetramethyldodecane-1-yl) carbonate (1.6 g, 70.3%). |
70.3% | With triethylamine In dichloromethane at 0 - 20℃; for 3h; | 29 [00163] 10,10,11,1 l-Tetramethyl-3, 6, 9-trioxa-10-siladodecan-l-ol (1.4 g, 5.3 mmol, 1.0 eq.), DCM (15 mL), and TEA (0.64 g, 6.4 mmol, 1.2 eq.) were mixed in a flask and cooled to 0 °C, followed by addition of p-nitrophenyl chloroformate (1.2 g, 5.8 mmol, 1.1 eq.; dissolved in DCM, 6 mL) dropwise. The reaction temperature was raised to rt; and the mixture was stirred at rt for 3 h. The mixture was absorbed on silica-gel, loaded onto a silica-gel column, and purified with eluent of a mixture pet-ether and ethyl acetate (from 100:0 to 100:20), giving p-nitrophenyl 10,10,11,11-tetramethyl-3, 6, 9-trioxa-10- siladodec-1-yl carbonate (1.6 g, 70.3%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C 2.1: triethylamine / N,N-dimethyl-formamide / 20 °C 2.2: 2 h / 20 °C | ||
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 3 h / 0 - 20 °C 2: triethylamine / N,N-dimethyl-formamide 3: triethylamine / ethanol / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 3 h / 0 - 20 °C 2: triethylamine / N,N-dimethyl-formamide |
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
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. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
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. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
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: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
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 |
H280 | Contains gas under pressure; may explode if heated |
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 |
Sorry,this product has been discontinued.
Home
* Country/Region
* Quantity Required :
* Cat. No.:
* CAS No :
* Product Name :
* Additional Information :