2H-Naphth(1,8-cd)isothiazole 1,1-dioxide

Base Information

• Chemical Name: 2H-Naphth(1,8-cd)isothiazole 1,1-dioxide
• CAS No.: 603-72-5
• Molecular Formula: C10H7 N O2 S
• Molecular Weight: 205.237
• Hs Code.: 2934991000
• European Community (EC) Number: 210-055-4
• DSSTox Substance ID: DTXSID90209060
• Nikkaji Number: J252.491K,J95.551E
• Wikidata: Q83083216
• Mol file: 603-72-5.mol

Synonyms:603-72-5;1,8-Naphthosultam;1,8-Naphthalenesultam;2H-naphtho[1,8-cd]isothiazole 1,1-dioxide;2H-Naphth(1,8-cd)isothiazole 1,1-dioxide;C10H7NO2S;2H-naphth[1,8-cd]isothiazole 1,1-dioxide;EINECS 210-055-4;2lambda6-thia-3-azatricyclo[6.3.1.04,12]dodeca-1(11),4,6,8(12),9-pentaene 2,2-dioxide;1,8-Naphthasultam;1,8-Naphthosultam, 97%;Oprea1_484801;SCHEMBL812924;DTXSID90209060;MFCD00009746;AKOS000291436;CCG-354060;naphtho[1,8-cd]isothiazole 1,1-dioxide;DS-11398;FT-0632505;2H-naphth [1,8-cd]isothiazole 1,1-dioxide;EN300-20310;F16725;A832709;SR-01000317064;CU-00000000137-1;SR-01000317064-1;BRD-K26533345-001-01-7;Z104477710;2lambda6-thia-3-azatricyclo[6.3.1.0,4,12]dodeca-1(11),4(12),5,7,9-pentaene-2,2-dione;ethyl 2-(phenylcarbamothioylamino)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate;2H-Naphtho[1,8-cd]isothiazole 1,1-dioxide

Chemical Property of 2H-Naphth(1,8-cd)isothiazole 1,1-dioxide

Chemical Property:

• Vapor Pressure: 5.11E-08mmHg at 25°C
• Melting Point: 173-175 °C(lit.)
• Refractive Index: 1.5250 (estimate)
• Boiling Point: 442.2°C at 760 mmHg
• Flash Point: 221.2°C
• PSA: 54.55000
• Density: 1.492g/cm³
• LogP: 3.17280
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 205.01974964
• Heavy Atom Count: 14
• Complexity: 333

Purity/Quality:

97% ^*data from raw suppliers

1,8-Naphthalenesultam 97% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C3C(=C1)NS(=O)(=O)C3=CC=C2

Technology Process of 2H-Naphth(1,8-cd)isothiazole 1,1-dioxide

There total 12 articles about 2H-Naphth(1,8-cd)isothiazole 1,1-dioxide 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: 95.0%

N-[(Z)-2-(4-methylphenylsulfonyl)ethenyl]-1,8-naphthosultam → 1,8-naphthosultam (603-72-5)

Guidance literature:

With sodium hydride; 1-dodecylthiol; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jo501647w

Reference yield: 70.0%

1,8-naphthyl amine sulphonic acid potassium salt (16619-06-0) → 1,8-naphthosultam (603-72-5)

Guidance literature:

With trichlorophosphate; at 130 ℃; for 3h;

DOI:10.1016/j.bmc.2011.12.003

Reference yield: 8.0%

N-(p-tolylsulfonyl)-1,8-naphthosultam (109593-01-3) → N-(p-tolylsulfonyl)-1-naphthylamine-8-sulfonic acid (130955-98-5) + 1,8-naphthosultam (603-72-5)

Guidance literature:

With sodium hydroxide; In ethanol; for 24h; Heating;

DOI:10.1021/jo00023a012

upstream raw materials:

N-(p-tolylsulfonyl)-1,8-naphthosultam

8-anilino-1-naphthalenesulfonate

hydrogenchloride

2-acetyl-2H-naphtho[1,8-cd]isothiazole 1,1-dioxide

Downstream raw materials:

2-benzenesulfonyl-2H-naphtho[1,8-cd]isothiazole 1,1-dioxide

1,8-dihydroxynaphthalene

2-(4-chlorobutyl)-2H-naphth<1,8-cd>isothiazole 1,1-dioxide

4-phenylazo-1,8-naphthosultam

Refernces

The Chemistry of Sultams. I. Friedel-Crafts Reactions of 1,8-Naphthosultam and its Derivatives. The Rearrangement of N,N-Di-(p-toluenesulfonyl)-aniline, N-Acyl- and N-Arylsulfonyl-1,8-naphthosultam Derivatives

10.1021/ja01622a044

The study investigates the Friedel-Crafts reactions of 1,8-naphthosultam and its derivatives, as well as the rearrangement of certain related compounds under specific conditions. 1,8-Naphthosultam (IIIa) and its N-methyl derivative (IIIb) are found to condense with acyl-, aroyl-, and arylsulfonyl chlorides in the presence of aluminum chloride to yield 4-acylated products. N-Acylated 1,8-naphthosultam derivatives (IIIc, d) migrate the acyl group under aluminum chloride's influence to form 4-acyl derivatives (IVa,b). Similar migrations are observed with N,N-di-(p-toluenesulfonyl)-aniline and N-arylsulfonyl-1,8-naphthosultam derivatives (IIIe,f). N-Phenylsulfonyl-1,8-naphthosultam (IIIe) also undergoes thermal migration of the phenylsulfonyl group when refluxed with nitrobenzene or aniline. The study further explores the rearrangement of N,N-di-(p-toluenesulfonyl)-aniline and N-acyl-, N-aroyl-, and N-arylsulfonyl-1,8-naphthosultam derivatives by aluminum chloride, and the thermal rearrangement of N-phenylsulfonyl-1,8-naphthosultam. Additionally, the dehydrobromination of 3-bromo-1,2,5,6-dibenz-1,5-cyclooctadiene (VIII) and 7-bromo-1,2,5,6-dibenz-1,3,5-cyclooctatriene (X) is studied to determine the step at which molecular rearrangement occurs, with VIII undergoing dehydrobromination without rearrangement, while X rearranges to form l-methylene-2,3,6,7-dibenzcycloheptatriene (II).

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