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Garg 4,5-indolyne precursor

95%

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Synonym(s):
4-(Trimethylsilyl)-1H-indol-5-yl trifluoromethanesulfonate
Empirical Formula (Hill Notation):
C12H14F3NO3SSi
CAS Number:
1259448-37-7
Molecular Weight:
337.39
MDL number:
MFCD25976536
UNSPSC Code:
12352100
PubChem Substance ID:
329768491
NACRES:
NA.22

Quality Level

100

Assay

95%

form

solid

mp

43-48 °C

storage temp.

2-8°C

SMILES string

O=S(OC1=C([Si](C)(C)C)C2=C(NC=C2)C=C1)(C(F)(F)F)=O

InChI

1S/C12H14F3NO3SSi/c1-21(2,3)11-8-6-7-16-9(8)4-5-10(11)19-20(17,18)12(13,14)15/h4-7,16H,1-3H3

InChI key

LLCJFYYASDIOJN-UHFFFAOYSA-N

Related Categories

General description

Garg 4,5-indolyne precursor is an indolyne precursor developed by Professor Neil Garg and coworkers. It is widely used for the synthesis of various N-heterocyclic based compounds. It is also useful for the preparation of substituted indoles (Diels–Alder and azide cycloaddition products).

Application

Indolyne precursor can be activated under mild fluoride conditions, which are highly reactive with dienes and other dipolariphiles (e.g. azides) to provide cycloaddition products containing an indole motif.

Other Notes

Indolyne Experimental and Computational Studies: Synthetic Applications and Origins of Selectivities of Nucleophilic Additions
Regioselective reactions of 3; 4-pyridynes enabled by the aryne distortion model

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Description
Pricing

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Garg Group – Professor Product Portal

The Garg group develops methods for the synthesis of natural products and pharmaceuticals. One key method pertains to heterocyclic arynes, such as indolynes and pyridynes, which are generated in situ from silyltriflate precursors under mild fluoride based reaction conditions.

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