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2-Chloro-4-nitro-benzenesulfonyl chloride, also known as NBS-Cl, is a chemical compound with the formula C6H3ClN2O4S. It is a white to pale yellow crystalline solid that is soluble in organic solvents such as dichloromethane and chloroform. NBS-Cl is recognized for its strong electrophilic and leaving group abilities, which make it a versatile reagent in organic synthesis.

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  • 20201-03-0 Structure
  • Basic information

    1. Product Name: 2-CHLORO-4-NITRO-BENZENESULFONYL CHLORIDE
    2. Synonyms: 2-Chloro-4-nitrobenzenesulfonylchloride; NSC 140589
    3. CAS NO:20201-03-0
    4. Molecular Formula: C6H3Cl2NO4S
    5. Molecular Weight: 256.07
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 20201-03-0.mol
  • Chemical Properties

    1. Melting Point: 66-67 °C(Solv: ligroine (8032-32-4))
    2. Boiling Point: 370.3°Cat760mmHg
    3. Flash Point: 177.7°C
    4. Appearance: /
    5. Density: 1.708g/cm3
    6. Vapor Pressure: 2.39E-05mmHg at 25°C
    7. Refractive Index: 1.599
    8. Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
    9. Solubility: N/A
    10. CAS DataBase Reference: 2-CHLORO-4-NITRO-BENZENESULFONYL CHLORIDE(CAS DataBase Reference)
    11. NIST Chemistry Reference: 2-CHLORO-4-NITRO-BENZENESULFONYL CHLORIDE(20201-03-0)
    12. EPA Substance Registry System: 2-CHLORO-4-NITRO-BENZENESULFONYL CHLORIDE(20201-03-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 20201-03-0(Hazardous Substances Data)

20201-03-0 Usage

Uses

Used in Organic Synthesis:
2-CHLORO-4-NITRO-BENZENESULFONYL CHLORIDE is used as a reagent for the preparation of sulfonyl chlorides, sulfonamides, sulfonate esters, and other sulfur-containing compounds. Its strong electrophilic and leaving group properties facilitate reactions involving nucleophilic substitution and electrophilic aromatic substitution.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 2-CHLORO-4-NITRO-BENZENESULFONYL CHLORIDE is used as an intermediate in the synthesis of various drugs. Its reactivity and ability to form sulfonyl chlorides make it a valuable component in the development of new pharmaceutical compounds.
Used in Dye Production:
2-CHLORO-4-NITRO-BENZENESULFONYL CHLORIDE is used as a chemical intermediate in the production of dyes. Its reactivity allows for the creation of a variety of dye structures with different properties.
Used in Agrochemical Production:
In the agrochemical industry, 2-CHLORO-4-NITRO-BENZENESULFONYL CHLORIDE is used as a precursor in the synthesis of various agrochemicals, contributing to the development of new pesticides and other agricultural chemicals.
Safety Precautions:
It is important to handle 2-CHLORO-4-NITRO-BENZENESULFONYL CHLORIDE with caution as it is a hazardous substance. It can cause skin and eye irritation, as well as respiratory and digestive complications if inhaled or ingested. Proper safety measures, including the use of personal protective equipment and handling in a well-ventilated area, should be taken to minimize exposure risks.

Check Digit Verification of cas no

The CAS Registry Mumber 20201-03-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,0,2,0 and 1 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 20201-03:
(7*2)+(6*0)+(5*2)+(4*0)+(3*1)+(2*0)+(1*3)=30
30 % 10 = 0
So 20201-03-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H3Cl2NO4S/c7-5-3-4(9(10)11)1-2-6(5)14(8,12)13/h1-3H

20201-03-0Upstream product

20201-03-0Relevant articles and documents

Metal Free Bi(hetero)aryl Synthesis: A Benzyne Truce-Smiles Rearrangement

Holden, Catherine M.,Sohel, Shariar M. A.,Greaney, Michael F.

supporting information, p. 2450 - 2453 (2016/02/18)

A new benzyne transformation is described that affords versatile biaryl structures without recourse to transition-metal catalysis or stoichiometric amounts of organometallic building blocks. Aryl sulfonamides add to benzyne upon fluoride activation, and then undergo an aryl Truce-Smiles rearrangement to afford biaryls with sulfur dioxide extrusion. The reaction proceeds under simple reaction conditions and has excellent scope for the synthesis of sterically hindered atropisomeric biaryl amines. All smiles: Metal-free biaryl synthesis is achieved by adding benzyne to arylsulfonamides. A Smiles rearrangement enables C-C bond formation, thus accessing a variety of functionalized biaryls under mild reaction conditions.

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