Lot numbers can be found on the outside label of a product:
Methyl 4-amino-5-chlorothiophene-2-carboxylate
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CAS No. 89499-44-5
- Cat. No. CS-0042864
- Purity≥97%
- MDL No.MFCD00508459
*For research and further manufacturing use only, not for direct human use.
Structure of 89499-44-5
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General Information
- CAS No. 89499-44-5
- Cat. No. CS-0042864
- Purity ≥97%
- MDL No. MFCD00508459
- Storage 4°C, protect from light
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₆H₆ClNO₂S
- Molecular Weight 191.64
- Synonym(s) 4-AMINO-5-CHLOROTHIOPHENE-2-CARBOXYLIC ACID METHYL ESTER
- SMILES NC1=C(SC(=C1)C(=O)OC)Cl
Description
Methyl 4-amino-5-chlorothiophene-2-carboxylate features a thiophene core with complementary electron-donating and electron-withdrawing substituents, enabling facile functionalization in cross-coupling and cyclization reactions. The amino group enhances reactivity in nucleophilic transformations, while the chloro moiety provides a handle for palladium-catalyzed substitutions. This scaffold offers high stability under standard conditions and integrates efficiently into complex molecular architectures.
Application
Methyl 4-amino-5-chlorothiophene-2-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to substituted thiophene scaffolds via Pd-catalyzed cross-coupling and electrophilic substitution. The ortho-positioned amino and chloro groups provide complementary reactivity for sequential functionalization, while the ester group supports derivatization or hydrolysis to the corresponding acid. Bench-stable and readily purified by recrystallization, it functions effectively in medicinal chemistry campaigns requiring robust, multi-step synthetic pathways.
Synthesis
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Route1
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In-stock
89166-85-8 - ~%
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In-stock
89499-44-5
References
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Chemistry of Heterocyclic Compounds (New York, NY, United States), , vol. 19, # 12 p. 1283 - 1286 Khimiya Geterotsiklicheskikh Soedinenii, , vol. 19, # 12 p. 1626 - 1629
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Route2
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In-stock
57800-76-7 - ~%
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In-stock
89499-44-5
References
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Chemistry of Heterocyclic Compounds (New York, NY, United States), , vol. 19, # 12 p. 1283 - 1286 Khimiya Geterotsiklicheskikh Soedinenii, , vol. 19, # 12 p. 1626 - 1629
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Route3
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89499-28-5 - ~%
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In-stock
89499-44-5
References
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Chemistry of Heterocyclic Compounds (New York, NY, United States), , vol. 19, # 12 p. 1283 - 1286 Khimiya Geterotsiklicheskikh Soedinenii, , vol. 19, # 12 p. 1626 - 1629
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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 52.32
- LogP 1.7703
- H_Acceptors 4
- H_Donors 1
- Rotatable_Bonds 1
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Key Words
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