Lot numbers can be found on the outside label of a product:
Methyl 3-iodoisonicotinate
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CAS No. 188677-49-8
- Cat. No. CS-W022833
- Purity≥95%
- MDL No.MFCD03411715
*For research and further manufacturing use only, not for direct human use.
Structure of 188677-49-8
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General Information
- CAS No. 188677-49-8
- Cat. No. CS-W022833
- Purity ≥95%
- MDL No. MFCD03411715
- Storage 4°C, protect from light
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₇H₆INO₂
- Molecular Weight 263.03
- Synonym(s) Methyl 3-iodopyridine-4-carboxylate
- SMILES COC(=O)C1=C(C=NC=C1)I
Description
Methyl 3-iodoisonicotinate is a bench-stable, moisture-tolerant iodinated heterocycle featuring a strategically positioned ester group. This compound integrates readily into cross-coupling protocols, serving as a key building block for synthesizing functionalized pyridine derivatives under standard conditions.
Application
Methyl 3-iodoisonicotinate serves as a versatile building block for the synthesis of functionalized heterocycles and bioactive molecules. The iodine substituent enables reliable cross-coupling reactions, including Suzuki-Miyaura and Stille couplings, while the ester group offers compatibility with standard reductions and nucleophilic transformations. Its bench-stable nature and predictable reactivity facilitate efficient incorporation into complex molecular architectures.
Synthesis
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Route1
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In-stock
57842-10-1 -
74-88-4 - ~58%
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In-stock
188677-49-8
References
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Uehling, David E.; Shearer, Barry G.; Donaldson, Kelly H.; Chao, Esther Y.; Deaton, David N.; Adkison, Kim K.; Brown, Kathleen K.; Cariello, Neal F.; Faison, Walter L.; Lancaster, Mary E.; Lin, Jasmine; Hart, Robert; Milliken, Tula O.; Paulik, Mark A.; Sherman, Bryan W.; Sugg, Elizabeth E.; Cowan, Conrad Journal of Medicinal Chemistry, 2006 , vol. 49, # 9 p. 2758 - 2771
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Route2
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In-stock
55279-30-6 - ~70%
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In-stock
188677-49-8
References
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Gwaltney II, Stephen L.; O'Connor, Stephen J.; Nelson, Lissa T. J.; Sullivan, Gerard M.; Imade, Hovis; Wang, Weibo; Hasvold, Lisa; Li, Qun; Cohen, Jerome; Gu, Wen-Zhen; Tahir, Stephen K.; Bauch, Joy; Marsh, Kennan; Ng, Shi-Chung; Frost, David J.; Zhang, Haiying; Muchmore, Steve; Jakob, Clarissa G.; Stoll, Vincent; Hutchins, Charles; Rosenberg, Saul H.; Sham, Hing L. Bioorganic and Medicinal Chemistry Letters, 2003 , vol. 13, # 7 p. 1359 - 1362
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Route3
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67-56-1
- ~%
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In-stock
188677-49-8
References
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WO2006/4195 A1, ; Page/Page column 74; 132 ; WO 2006/004195 A2
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H302-H315-H319-H335
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Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 39.19
- LogP 1.4728
- H_Acceptors 3
- H_Donors 0
- Rotatable_Bonds 1
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Key Words
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