3-Nitrobenzenesulfonyl chloride

Base Information

• Chemical Name: 3-Nitrobenzenesulfonyl chloride
• CAS No.: 121-51-7
• Molecular Formula: C6H4ClNO4S
• Molecular Weight: 221.621
• Hs Code.: 29049090
• European Community (EC) Number: 204-476-2
• NSC Number: 9806
• UNII: KN1Z8WPL9U
• DSSTox Substance ID: DTXSID6059526
• Nikkaji Number: J28.764D
• Wikidata: Q27282337
• Mol file: 121-51-7.mol

Synonyms:3-Nitrobenzenesulfonyl chloride;121-51-7;3-nitrobenzene-1-sulfonyl chloride;Benzenesulfonyl chloride, 3-nitro-;3-Nitro-benzenesulfonyl chloride;3-Nitrophenylsulfonyl chloride;3-Nitrobenzenesulphonyl chloride;M-NITROBENZENESULFONYL CHLORIDE;m-Nitrophenylsulfonyl chloride;Benzenesulfonyl chloride, m-nitro-;UNII-KN1Z8WPL9U;KN1Z8WPL9U;m-nitrobenzene sulfonyl chloride;NSC 9806;NSC-9806;EINECS 204-476-2;MFCD00007435;3-Nitro-benzenesulfonylchloride;M-NOSYL CHLORIDE;m-Nitrosulphonyl chloride;3-chlorosulfonylnitrobenzene;m-nitrobenzensulfonylchloride;SCHEMBL58443;3-Nitrobenzenesulfonylchloride;3-nitrobenzensulfonyl chloride;3-nitrobezenesulfonyl chloride;3-nitrophenylsulphonyl chloride;3-nitrophenyl-sulfonyl chloride;SCHEMBL2625180;3-Nitro benzenesulfonyl chloride;3-nitrobenzene sulfonyl chloride;DTXSID6059526;3-nitro-benzenesulphonyl chloride;3-nitrobenzene sulphonyl chloride;meta-nitrobenzenesulfonyl chloride;MWWNNNAOGWPTQY-UHFFFAOYSA-;NSC9806;3-nitro benzene sulphonyl chloride;3-nitro-1-benzenesulphonyl chloride;(3-nitro)-phenyl-sulphonyl chloride;3-Nitrobenzenesulfonic acid chloride;m-nitrobenzene sulfonic acid chloride;STL199176;3-(CHLOROSULFONYL)NITROBENZENE;3-Nitrobenzenesulfonyl chloride, 97%;AKOS000119891;GS-3087;NITROBENZENESULFONYL CHLORIDE, M-;A2561;AM20020296;FT-0616237;N0143;EN300-17285;W-108455;Q27282337;F0808-2029

Chemical Property of 3-Nitrobenzenesulfonyl chloride

Chemical Property:

• Appearance/Colour: light beige to yellow crystalline powder
• Vapor Pressure: 0.000164mmHg at 25°C
• Melting Point: 61-62 °C(lit.)
• Refractive Index: 1.588
• Boiling Point: 341 °C at 760 mmHg
• Flash Point: 160 °C
• PSA: 88.34000
• Density: 1.606 g/cm³
• LogP: 3.12630
• Storage Temp.: Store below +30°C.
• Sensitive.: Moisture Sensitive
• Water Solubility.: Decomposes
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 220.9549565
• Heavy Atom Count: 13
• Complexity: 291

Purity/Quality:

99% ^*data from raw suppliers

3-NitrobenzenesulfonylChlrodie ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-29-14
• Safety Statements: 26-36/37/39-45-8

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)S(=O)(=O)Cl)[N+](=O)[O-]
• General Description: 3-Nitrobenzenesulfonyl chloride (3-NBSC) is a reactive sulfonylating agent used in the arenesulfonylation of amino acids such as DL-serine, L-proline, DL-threonine, and DL-methionine. The compound reacts preferentially with the anionic form of these amino acids in mixed solvent systems (1,4-dioxane—water or propan-2-ol—water), with the reaction kinetics influenced by the basicity of the amino acids. Its reactivity has been compared to other acylating agents like benzoyl chloride and benzoic acid 4-nitrophenyl ester, highlighting its utility in synthesizing sulfamides, which serve as enzyme inhibitors and protective groups in organic synthesis. The reaction progress can be monitored spectrophotometrically at 242 nm, confirming its role as an efficient sulfonylation reagent under controlled pH conditions.

Technology Process of 3-Nitrobenzenesulfonyl chloride

There total 15 articles about 3-Nitrobenzenesulfonyl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

3-nitrophenylsulfonohydrazide (6655-77-2) → 3-nitrobenzenesulphonyl chloride (121-51-7)

Guidance literature:

With N-chloro-succinimide; In acetonitrile; at 20 ℃; for 2h;

DOI:10.3390/molecules26185551

Reference yield: 96.3%

→ 3-nitrobenzenesulphonyl chloride (121-51-7)

Guidance literature:

Reference yield: 95.0%

sodium 3-nitrobenzenesulfonate (127-68-4) → 3-nitrobenzenesulphonyl chloride (121-51-7)

Guidance literature:

With trichlorophosphate; In sulfolane; acetonitrile; at 68 - 72 ℃; for 0.666667h;

DOI:10.1055/s-1982-29823

upstream raw materials:

3-nitrophenylsulfonamide

3-nitrophenyldiazonium chloride

sodium 3-nitrobenzenesulfonate

nitrobenzene

Downstream raw materials:

1,4-bis(3-nitrophenylsulfonyl)piperazine

3-nitro-N-(pyridin-2-yl)benzenesulfonamide

3-nitro-N-pyrimidin-2-ylbenzenesulfonamide

3-nitro-benzenesulfonic acid-[1,3,4]thiadiazol-2-ylamide

Refernces

Arenesulfonylation of dl-serine, l-proline, l-threonine, and dl-methionine in systems 1,4-dioxane-water and propan-2-ol-water

10.1007/s11172-010-0186-0

The research focuses on the kinetics of the arenesulfonylation reaction involving DL-serine, L-proline, DL-threonine, and DL-methionine with 3-nitrobenzenesulfonyl chloride (3-NBSC) in mixed solvent systems of 1,4-dioxane—water and propan-2-ol—water. The study was conducted spectrophotometrically at 298 K to determine the reaction rate constants and understand the reactive forms of the amino acids. The main reactive form was found to be anionic, and the basicity of the α-amino acids was identified as a crucial factor in determining the reaction rate. The rate constants for arenesulfonylation were compared with those of N-acylation with benzoyl chloride and reactions with benzoic acid 4-nitrophenyl ester. The experiments involved monitoring the reaction's progress by tracking changes in 3-NBBSC concentration at 242 nm using a spectrophotometer. The reaction conditions, including pH, were controlled using an acetate buffer, and the pH was measured with an ionomer. The research aimed to optimize synthetic conditions for sulfamides, which are important due to their role in enzyme inhibition and as protective groups in organic synthesis.