2-Chloro-5-methylthiophene

Name: 2-Chloro-5-methylthiophene
Brand: ChemScene
Availability: InStock
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CAS No. 17249-82-0
Cat. No. CS-0194560
Purity≥98%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Structure of 17249-82-0

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General Information

CAS No. 17249-82-0
Cat. No. CS-0194560
Purity ≥98%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₅ClS
Molecular Weight 132.61
Synonym(s) None
SMILES CC1=CC=C(Cl)S1

Description

2-Chloro-5-methylthiophene serves as a key heterocyclic building block in synthetic organic chemistry, featuring a chlorinated thiophene core with a methyl group at the 5-position. This substitution pattern imparts enhanced reactivity in palladium-catalyzed cross-coupling reactions, enabling efficient access to functionalized thienyl architectures under standard conditions. The molecule exhibits good stability and handles well in air and moisture during routine bench operations.

Application

2-Chloro-5-methylthiophene serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions with broad functional group tolerance. Its electrophilic chlorine site facilitates Suzuki, Stille, and Negishi couplings under standard conditions, while the methylthio group provides orthogonal reactivity for selective transformations. The compound exhibits good bench stability and is readily purified by distillation or column chromatography, making it well-suited for iterative synthetic sequences in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  554-14-3
- ~83%
- In-stock
  
  17249-82-0
References
- Lucas, Linda N.; De Jong, Jaap J. D.; Van Esch, Jan H.; Kellogg, Richard M.; Feringa, Ben L. European Journal of Organic Chemistry, 2003 , # 1 p. 155 - 166
Route2
- In-stock
  
  7283-96-7
- ~%
- In-stock
  
  17249-82-0
References
- Journal of Organic Chemistry, , vol. 14, p. 638,639

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS02
Signal Word : Danger	UN#: 1993
Class : 3	Packing Group : Ⅲ
Hazard Statements : H225-H315-H319
Precautionary Statements : P210-P233-P240-P241-P242-P243-P264-P280-P302+P352-P501

Quality Control

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Computational Chemistry Data

TPSA 0
LogP 2.70992
H_Acceptors 1
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Thiophene compounds

Key Words

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2-Chloro-5-methylthiophene

CAS No. 17249-82-0

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