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Merck
CN

795569

Garg 4,5-indolyne precursor

95%

Synonym(s):

4-(Trimethylsilyl)-1H-indol-5-yl trifluoromethanesulfonate

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About This Item

Empirical Formula (Hill Notation):
C12H14F3NO3SSi
CAS Number:
1259448-37-7
Molecular Weight:
337.39
NACRES:
NA.22
PubChem Substance ID:
329768491
UNSPSC Code:
12352100
MDL number:
MFCD25976536
Assay:
95%
Form:
solid

Key Documents

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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

SMILES string

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

InChI key

LLCJFYYASDIOJN-UHFFFAOYSA-N

assay

95%

form

solid

mp

43-48 °C

functional group

fluoro, triflate

storage temp.

2-8°C

Quality Level

100

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCJ8502
MKBT3221V

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Articles

Heterocyclic Aryne Precursors: New Opportunities for the Synthesis of Highly Substituted Indoles and Pyridines

New and efficient methods for the synthesis of functionalized heterocycles are highly sought after.

Related Content

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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