Cas no 1595870-36-2 ((4-bromo-2-nitrophenyl)methanesulfonyl chloride)

(4-Bromo-2-nitrophenyl)methanesulfonyl chloride is a specialized sulfonylating reagent used in organic synthesis, particularly for introducing the methanesulfonyl (mesyl) group into aromatic systems. Its key advantages include high reactivity due to the electron-withdrawing nitro and bromo substituents, which enhance its electrophilic character. This compound is valuable in the preparation of sulfonamides, sulfonate esters, and other derivatives, serving as a versatile intermediate in pharmaceutical and agrochemical research. The bromo substituent offers further functionalization potential via cross-coupling reactions. It is typically handled under anhydrous conditions to prevent hydrolysis. Suitable for controlled reactions, it provides precise selectivity in complex synthetic pathways.
(4-bromo-2-nitrophenyl)methanesulfonyl chloride structure
1595870-36-2 structure
Product Name:(4-bromo-2-nitrophenyl)methanesulfonyl chloride
CAS No:1595870-36-2
MF:C7H5BrClNO4S
MW:314.540899038315
MDL:MFCD31420904
CID:5245452
PubChem ID:114380893
Update Time:2026-03-08

(4-bromo-2-nitrophenyl)methanesulfonyl chloride Chemical and Physical Properties

Names and Identifiers

    • Benzenemethanesulfonyl chloride, 4-bromo-2-nitro-
    • (4-bromo-2-nitrophenyl)methanesulfonyl chloride
    • MDL: MFCD31420904
    • Inchi: 1S/C7H5BrClNO4S/c8-6-2-1-5(4-15(9,13)14)7(3-6)10(11)12/h1-3H,4H2
    • InChI Key: GUXYENHEWIKUAF-UHFFFAOYSA-N
    • SMILES: C1(CS(Cl)(=O)=O)=CC=C(Br)C=C1[N+]([O-])=O

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Additional information on (4-bromo-2-nitrophenyl)methanesulfonyl chloride

Comprehensive Overview of (4-bromo-2-nitrophenyl)methanesulfonyl chloride (CAS No. 1595870-36-2)

(4-bromo-2-nitrophenyl)methanesulfonyl chloride (CAS No. 1595870-36-2) is a specialized sulfonyl chloride derivative widely utilized in organic synthesis and pharmaceutical intermediates. This compound features a bromonitrophenyl backbone coupled with a reactive methanesulfonyl chloride group, making it a valuable building block for cross-coupling reactions and heterocyclic compound development. Its unique structure enables applications in drug discovery, material science, and agrochemical research.

The growing demand for high-purity intermediates like (4-bromo-2-nitrophenyl)methanesulfonyl chloride reflects trends in green chemistry and sustainable synthesis. Researchers frequently search for "CAS 1595870-36-2 solubility" or "nitrophenyl sulfonyl chloride applications," highlighting its relevance in catalysis and peptide modification. Recent studies emphasize its role in click chemistry and bioconjugation, aligning with the rise of targeted drug delivery systems.

From a synthetic chemistry perspective, this compound’s electron-withdrawing nitro and bromo groups enhance its reactivity in nucleophilic substitution reactions. Laboratories often inquire about "1595870-36-2 handling precautions" or "methanesulfonyl chloride stability," underscoring the need for proper storage conditions (e.g., anhydrous environments). Its melting point and NMR spectra data are critical for quality control in batch production.

Innovations in flow chemistry have further amplified interest in (4-bromo-2-nitrophenyl)methanesulfonyl chloride, as it enables continuous manufacturing of complex molecules. The compound’s compatibility with microwave-assisted synthesis and photocatalysis positions it as a candidate for high-throughput screening. Searches for "bromo-nitrophenyl derivatives suppliers" or "sulfonylation reagent alternatives" indicate its commercial importance.

In medicinal chemistry, this intermediate contributes to the development of kinase inhibitors and antibody-drug conjugates (ADCs). Its CAS No. 1595870-36-2 is frequently cited in patents related to anticancer agents and anti-inflammatory drugs. The compound’s regioselectivity in reactions with amino acids or heteroaromatics makes it indispensable for structure-activity relationship (SAR) studies.

Environmental considerations drive research into biodegradable sulfonylating agents, though (4-bromo-2-nitrophenyl)methanesulfonyl chloride remains preferred for its high yield and scalability. Analytical techniques like HPLC-MS and FT-IR are essential for verifying its purity, addressing queries such as "how to characterize sulfonyl chlorides." Future applications may expand into polymeric materials and electronic chemicals.

For suppliers and manufacturers, optimizing synthesis routes of CAS 1595870-36-2 to reduce byproduct formation is a priority. The compound’s cost-effectiveness compared to similar aryl sulfonyl chlorides sustains its market demand. Regulatory compliance with REACH and GMP standards ensures its safe use in API production.

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