1-Methyl-1H-pyrazole-4-sulfonyl chloride

Name: 1-Methyl-1H-pyrazole-4-sulfonyl chloride
Brand: ChemScene
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CAS No. 288148-34-5
Cat. No. CS-W007568
Purity≥95%
MDL No.None

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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1-Methyl-1H-pyrazole-4-sulfonyl chloride|CS-W007568

Structure of 288148-34-5

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General Information

CAS No. 288148-34-5
Cat. No. CS-W007568
Purity ≥95%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₄H₅ClN₂O₂S
Molecular Weight 180.61
Synonym(s) 4-(Chlorosulphonyl)-1-methyl-1H-pyrazole
SMILES O=S(C1=CN(C)N=C1)(Cl)=O

Description

1-Methyl-1H-pyrazole-4-sulfonyl chloride features a reactive sulfonyl chloride group appended to a nitrogen-rich pyrazole scaffold, enabling direct coupling with amines and alcohols under mild conditions. The methyl substitution enhances solubility and electronic modulation, while the aromatic core ensures stability during functionalization. This reagent streamlines access to sulfonamide and sulfonate derivatives in medicinal chemistry and materials synthesis.

Application

1-Methyl-1H-pyrazole-4-sulfonyl chloride serves as a versatile sulfonylating agent for the efficient introduction of the 1-methyl-1H-pyrazol-4-ylsulfonyl group into diverse substrates. It facilitates the synthesis of sulfonamide derivatives with enhanced metabolic stability and improved solubility, commonly encountered in medicinal chemistry campaigns. The reagent exhibits good bench stability, reacts selectively with amines under mild conditions, and enables straightforward purification via crystallization or column chromatography.

Synthesis

Route1
- 930-36-9
- ~33%
- In-stock
  
  288148-34-5
References
- ELI LILLY AND COMPANY Patent: WO2009/29439 A1, 2009 ; Location in patent: Page/Page column 24 ; WO 2009/029439 A1
Route2
- In-stock
  
  39806-90-1
- ~99%
- In-stock
  
  288148-34-5
References
- Naganawa, Atsushi; Matsui, Toshiaki; Saito, Tetsuji; Ima, Masaki; Tatsumi, Tadashi; Yamamoto, Shingo; Murota, Masayuki; Yamamoto, Hiroshi; Maruyama, Takayuki; Ohuchida, Shuichi; Nakai, Hisao; Kondo, Kigen; Toda, Masaaki Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 19 p. 6628 - 6639

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS05
Signal Word : Danger	UN#: 3261
Class : 8	Packing Group : Ⅲ
Hazard Statements : H314
Precautionary Statements : P260-P280-P301+P330+P331-P304+P340

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Computational Chemistry Data

TPSA 51.96
LogP 0.3476
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Pyrazole compounds

Key Words

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1-Methyl-1H-pyrazole-4-sulfonyl chloride

CAS No. 288148-34-5

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