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CAS RN: 181934-30-5 | Product Number: T3039

1-[(Triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one


Purity: >98.0%(HPLC)
Synonyms:
  • TIPS-EBX
Documents:
200MG
₹4,700.00
1   14  
1G
₹16,100.00
4   ≥40 

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Product Number T3039
Purity / Analysis Method >98.0%(HPLC)
Molecular Formula / Molecular Weight C__1__8H__2__5IO__2Si = 428.39 
Physical State (20 deg.C) Solid
Store Under Inert Gas Store under inert gas
Condition to Avoid Light Sensitive,Hygroscopic
Packaging and Container 1G-Glass Bottle with Plastic Insert (View image)
CAS RN 181934-30-5
Reaxys Registry Number 7712699
PubChem Substance ID 253660203
MDL Number

MFCD18632570

Specifications
Appearance White to Almost white powder to crystal
Purity(HPLC) min. 98.0 area%
Properties (reference)
Melting Point 170 °C(dec.)
GHS
Pictogram Pictogram
Signal Word Warning
Hazard Statements H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
H413 : May cause long lasting harmful effects to aquatic life.
Precautionary Statements P501 : Dispose of contents/ container to an approved waste disposal plant.
P273 : Avoid release to the environment.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ eye protection/ face protection.
P302 + P352 : IF ON SKIN: Wash with plenty of water.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P362 + P364 : Take off contaminated clothing and wash it before reuse.
P332 + P313 : If skin irritation occurs: Get medical advice/ attention.
Related Laws:
Transport Information:
Application
C2-Selective Ethynylation of Indoles

T3039 & M0561

In a 10 mL round bottom-flask, 1-methyl-1H-indole (0.500 mmol, 65.6 mg) and 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX) (1.50 mmol, 643 mg) are dissolved in DCM (5 mL) under air, then water is added (0.10 mL). Lastly Pd(MeCN)4(BF4)2 (2 mol%, 4.4 mg) is added with strong stirring. The flask is closed and the reaction mixture is stirred overnight (the reaction is generally completed after 4-6 h), when it became brownish. The solvent is evaporated under reduced pressure. EtOAc (25 mL) is added to the crude product, and the solution is washed with NaOH aq (0.1 M, 25 mL), conc. NaHCO3 (2 x 25 mL) and brine (25 mL). The organic layer is dried over MgSO4, filtered and the solvent is evaporated under reduced pressure. Purification by column chromatography gives the pure 1-methyl-2-[(triisopropylsilyl)ethynyl]-1H-indole as a pale yellow oil (66%, 102 mg).

References


Application
C3-Selective Ethynylation of Indoles

Experimental procedure: TIPS-EBX (1.0 g, 2.4 mmol, 1.2 eq.) is added to a stirring solution of AuCl (4.6 mg, 0.020 mmol, 0.01 eq.) and indole (0.24 g, 2.0 mmol, 1.0 eq.) in Et2O (40 mL) under air. The reaction is sealed and stirred at room temperature for 12-15 h. Et2O (50 mL) is added, the organic layer is washed twice with NaOH aq (0.1 mol/L, 50 mL). The aqueous layers are combined and extracted with Et2O (50 mL). The organic layers are combined, washed with saturated NaHCO3 (50 mL), brine (50 mL), dried with MgSO4 and concentrated under reduced pressure. Purification by flash chromatography (PET:Et2O = 8:2) affords 1 (498 mg, 1.68 mmol, 84%) as brown solid.

References


PubMed Literature


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