Lot numbers can be found on the outside label of a product:
Methyl 2-bromothiophene-3-carboxylate
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CAS No. 76360-43-5
- Cat. No. CS-W018777
- Purity≥96%
- MDL No.MFCD16657906
*For research and further manufacturing use only, not for direct human use.
Structure of 76360-43-5
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General Information
- CAS No. 76360-43-5
- Cat. No. CS-W018777
- Purity ≥96%
- MDL No. MFCD16657906
- Storage 4°C, protect from light
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₆H₅BrO₂S
- Molecular Weight 221.07
- Synonym(s) 2-BroMo-thiophene-3-carboxylic acid Methyl ester
- SMILES O=C(C1=C(Br)SC=C1)OC
Description
Methyl 2-bromothiophene-3-carboxylate features a brominated thiophene core that enables direct functionalization in cross-coupling reactions. The ester group provides a handle for further derivatization, while the electron-deficient ring enhances reactivity in palladium-catalyzed transformations. This bench-stable compound serves as a key intermediate in heterocyclic synthesis.
Application
Methyl 2-bromothiophene-3-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its well-established bromo functionality. The methyl ester group offers orthogonal reactivity for selective transformations, while the thiophene core provides structural rigidity and electronic properties relevant to pharmaceutical and agrochemical scaffolds. Bench-stable and compatible with standard synthetic workflows, it facilitates efficient access to substituted thiophenes under mild conditions.
Synthesis
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Route1
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67-56-1 -
In-stock
24287-95-4 - ~95%
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In-stock
76360-43-5
References
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CHUA, Peter C.; Haddach, Mustapha; Nagasawa, Johnny Y.; Pierre, Fabrice; Whitten, Jeffrey P. Patent: US2009/239859 A1, 2009 ; Location in patent: Page/Page column 90 ; US 20090239859 A1
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Route2
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186581-53-3
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In-stock
24287-95-4
- ~99%
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In-stock
76360-43-5
References
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Pomerantz, Martin; Amarasekara, Ananda S.; Rasika Dias Journal of Organic Chemistry, 2002 , vol. 67, # 20 p. 6931 - 6937
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Route3
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In-stock
24287-95-4
- ~%
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In-stock
76360-43-5
References
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Pierre, Fabrice; Chua, Peter C.; Obrien, Sean E.; Siddiqui-Jain, Adam; Bourbon, Pauline; Haddach, Mustapha; Michaux, Jerome; Nagasawa, Johnny; Schwaebe, Michael K.; Stefan, Eric; Vialettes, Anne; Whitten, Jeffrey P.; Chen, Ta Kung; Darjania, Levan; Stansfield, Ryan; Anderes, Kenna; Bliesath, Josh; Drygin, Denis; Ho, Caroline; Omori, May; Proffitt, Chris; Streiner, Nicole; Trent, Katy; Rice, William G.; Ryckman, David M. Journal of Medicinal Chemistry, 2011 , vol. 54, # 2 p. 635 - 654
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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 26.3
- LogP 2.2972
- H_Acceptors 3
- H_Donors 0
- Rotatable_Bonds 1
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Key Words
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