Cas no 680591-58-6 (6-(Dimethylamino)pyridine-3-sulfonyl Chloride)
6-(Dimethylamino)pyridine-3-sulfonyl Chloride Chemical and Physical Properties
Names and Identifiers
-
- 3-Pyridinesulfonyl chloride, 6-(dimethylamino)-
- 6-dimethylamino-pyridine-3-sulfonyl chloride
- SCHEMBL1038539
- EN300-176247
- 680591-58-6
- 6-(dimethylamino)pyridine-3-sulfonyl chloride
- AKOS006333398
- GS2996
- 2-dimethylamino-pyridine-5-sulfonyl chloride
- 6-(dimethylamino)pyridine-3-sulfonylchloride
- DB-333516
- GMCDYLKBLYZSFW-UHFFFAOYSA-N
- 6-(Dimethylamino)pyridine-3-sulfonyl Chloride
-
- Inchi: 1S/C7H9ClN2O2S/c1-10(2)7-4-3-6(5-9-7)13(8,11)12/h3-5H,1-2H3
- InChI Key: GMCDYLKBLYZSFW-UHFFFAOYSA-N
- SMILES: ClS(C1=CN=C(C=C1)N(C)C)(=O)=O
Computed Properties
- Exact Mass: 220.00747
- Monoisotopic Mass: 220.0073264g/mol
- Isotope Atom Count: 0
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 4
- Heavy Atom Count: 13
- Rotatable Bond Count: 2
- Complexity: 260
- Covalently-Bonded Unit Count: 1
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count : 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- XLogP3: 1.3
- Topological Polar Surface Area: 58.6?2
Experimental Properties
- PSA: 50.27
6-(Dimethylamino)pyridine-3-sulfonyl Chloride Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| TRC | B402735-5mg |
6-(Dimethylamino)pyridine-3-sulfonyl Chloride |
680591-58-6 | 5mg |
$ 70.00 | 2022-06-07 | ||
| TRC | B402735-10mg |
6-(Dimethylamino)pyridine-3-sulfonyl Chloride |
680591-58-6 | 10mg |
$ 95.00 | 2022-06-07 | ||
| TRC | B402735-50mg |
6-(Dimethylamino)pyridine-3-sulfonyl Chloride |
680591-58-6 | 50mg |
$ 340.00 | 2022-06-07 | ||
| Enamine | EN300-176247-0.05g |
6-(dimethylamino)pyridine-3-sulfonyl chloride |
680591-58-6 | 90% | 0.05g |
$268.0 | 2023-09-20 | |
| Enamine | EN300-176247-0.1g |
6-(dimethylamino)pyridine-3-sulfonyl chloride |
680591-58-6 | 90% | 0.1g |
$400.0 | 2023-09-20 | |
| Enamine | EN300-176247-0.25g |
6-(dimethylamino)pyridine-3-sulfonyl chloride |
680591-58-6 | 90% | 0.25g |
$572.0 | 2023-09-20 | |
| Enamine | EN300-176247-0.5g |
6-(dimethylamino)pyridine-3-sulfonyl chloride |
680591-58-6 | 90% | 0.5g |
$902.0 | 2023-09-20 | |
| Enamine | EN300-176247-1.0g |
6-(dimethylamino)pyridine-3-sulfonyl chloride |
680591-58-6 | 90% | 1g |
$1157.0 | 2023-05-26 | |
| Enamine | EN300-176247-2.5g |
6-(dimethylamino)pyridine-3-sulfonyl chloride |
680591-58-6 | 90% | 2.5g |
$2268.0 | 2023-09-20 | |
| Enamine | EN300-176247-5.0g |
6-(dimethylamino)pyridine-3-sulfonyl chloride |
680591-58-6 | 90% | 5g |
$3355.0 | 2023-05-26 |
6-(Dimethylamino)pyridine-3-sulfonyl Chloride Related Literature
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Saeideh Mirfakhraei,Malak Hekmati,Fereshteh Hosseini Eshbala,Hojat Veisi New J. Chem., 2018,42, 1757-1761
-
Xingqun Zheng,Lele Song,Xin Feng,Li Li,Zidong Wei J. Mater. Chem. A, 2020,8, 14145-14151
Additional information on 6-(Dimethylamino)pyridine-3-sulfonyl Chloride
Comprehensive Guide to 6-(Dimethylamino)pyridine-3-sulfonyl Chloride (CAS No. 680591-58-6): Properties, Applications, and Industry Insights
6-(Dimethylamino)pyridine-3-sulfonyl Chloride (CAS 680591-58-6) is a specialized sulfonylation reagent widely utilized in organic synthesis and pharmaceutical intermediates. This compound, often abbreviated as DMAP-SO?Cl, has gained significant attention due to its high reactivity in amide bond formation and peptide coupling reactions. With the growing demand for high-efficiency catalysts in drug discovery, this chemical has become a focal point for researchers exploring green chemistry alternatives to traditional coupling agents.
The molecular structure of 6-(Dimethylamino)pyridine-3-sulfonyl Chloride features a pyridine core with a dimethylamino group at the 6-position and a sulfonyl chloride moiety at the 3-position. This unique arrangement enables dual functionality: the DMAP group acts as an acyl transfer catalyst, while the sulfonyl chloride serves as an activating agent. Recent studies highlight its superiority over conventional reagents like EDCI or HOBt in terms of reaction yield and byproduct minimization.
In pharmaceutical applications, CAS 680591-58-6 demonstrates exceptional performance in API synthesis, particularly for protease inhibitor class drugs. Its ability to facilitate stereoselective reactions makes it valuable for constructing complex chiral molecules. The compound's water solubility (when converted to sulfonate) addresses a key challenge in bioconjugation chemistry, aligning with current trends toward biocompatible reagents.
From a sustainability perspective, 6-(Dimethylamino)pyridine-3-sulfonyl Chloride supports atom economy principles by reducing solvent consumption in multistep syntheses. Laboratories focusing on flow chemistry systems report improved process efficiency when incorporating this reagent. These advantages respond to the pharmaceutical industry's push for cost-effective manufacturing and waste reduction strategies.
Quality control of 680591-58-6 requires strict monitoring of purity parameters, typically verified through HPLC analysis and spectroscopic characterization. Storage recommendations emphasize protection from moisture at 2-8°C to maintain stability. These protocols reflect the compound's sensitivity while ensuring batch-to-batch consistency – a critical factor for GMP-compliant production.
Emerging research explores the reagent's potential in material science, particularly for modifying polymer surfaces and creating functionalized nanomaterials. Its dual-reactive sites enable novel approaches to covalent organic frameworks (COFs), positioning it at the forefront of smart material development. Such applications align with global interest in advanced functional materials for energy storage and sensor technologies.
The commercial availability of 6-(Dimethylamino)pyridine-3-sulfonyl Chloride has expanded significantly, with suppliers offering custom purity grades ranging from 95% to 99.9%. Procurement specialists should evaluate certificates of analysis and consider scale-up feasibility when selecting vendors. Market analysis indicates growing demand from contract research organizations and academic institutions engaged in medicinal chemistry programs.
Safety protocols for handling CAS 680591-58-6 emphasize standard laboratory precautions including glove box use for moisture-sensitive operations. The compound's MSDS specifications detail appropriate neutralization procedures for spill scenarios. These guidelines reflect evolving laboratory safety standards while maintaining operational practicality for synthetic chemists.
Future developments may focus on derivatization strategies to enhance the reagent's selectivity profile or create immobilized versions for heterogeneous catalysis. Such innovations would address industry needs for recyclable reagents and continuous processing methodologies. The compound's versatility ensures its continued relevance across chemical biology, drug discovery, and materials engineering applications.
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