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5-(Thiophen-2-yl)pentanoic acid
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CAS No. 21010-06-0
- Cat. No. CS-0324015
- Purity≥98%
- MDL No.MFCD00151849
*For research and further manufacturing use only, not for direct human use.
Structure of 21010-06-0
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General Information
- CAS No. 21010-06-0
- Cat. No. CS-0324015
- Purity ≥98%
- MDL No. MFCD00151849
- Storage 4°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₉H₁₂O₂S
- Molecular Weight 184.26
- Synonym(s) 5-(2-Thienyl)Pentanoic Acid
- SMILES C(CCC(=O)O)CC1=CC=CS1
Description
5-(Thiophen-2-yl)pentanoic acid features a thiophene ring tethered via a five-carbon aliphatic chain to a carboxylic acid group, enabling integration into bioactive molecules requiring aromatic-hydrophobic balance. The pendant thiophene imparts electron-rich character and planarity, enhancing π-stacking interactions in target binding. This structure supports applications in medicinal chemistry and materials science where controlled solubility and electronic properties are critical.
Application
5-(Thiophen-2-yl)pentanoic acid serves as a versatile building block for the synthesis of bioactive molecules, particularly in medicinal chemistry and agrochemical research. Its thiophene-containing alkyl chain provides enhanced metabolic stability and favorable lipophilicity, enabling efficient incorporation into diverse scaffolds. The carboxylic acid functionality facilitates straightforward derivatization via amide, ester, or acyl chloride formation, supporting broad synthetic utility in peptide conjugation and macrocyclization strategies.
Synthesis
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Route1
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22971-62-6 - ~82%
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In-stock
21010-06-0
References
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Pau, Amedeo; Murineddu, Gabriele; Asproni, Battistina; Murruzzu, Caterina; Grella, Giuseppe E.; Pinna, Gerard A.; Curzu, Maria M.; Marchesi, Irene; Bagella, Luigi Molecules, 2009 , vol. 14, # 9 p. 3494 - 3508
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Route2
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108-55-4 - ~%
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In-stock
21010-06-0
References
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Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, , vol. 222, p. 1301 Journal of Biological Chemistry, , vol. 146, p. 483
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Route3
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26359-28-4
- ~%
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In-stock
21010-06-0
References
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Journal of Organic Chemistry, , vol. 59, # 23 p. 7072 - 7084
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS05,GHS07
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Signal Word : Danger
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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 : H315-H318-H335
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Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P362-P403+P233-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 37.3
- LogP 2.5455
- H_Acceptors 2
- H_Donors 1
- Rotatable_Bonds 5
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Key Words
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