473-34-7

Basic information

• Product Name: DICHLORAMINE T
• Synonyms: N,N-dichloro-4-methylbenzenesulfonamide;N,N-dichloro-4-methyl-benzenesulfonamide;Dichloroamine-T;Benzyl p-sulfondichloramide;N,N-Dichloro-4-toluenesulfonamide;N,N-Dichloro-p-methylbenzenesulfonamide;N,N-Dichloro-p-tolylsulfonamide;N,N-Dichloro-p-toluenesulfonamide p-Toluenesulfondichloramide
• CAS NO: 473-34-7
• Molecular Formula: C₇H₇Cl₂NO₂S
• Molecular Weight: 240.11
• EINECS: 207-462-4
• Product Categories: Oxidation;Synthetic Organic Chemistry;Chlorination;Halogenation
• Mol File: 473-34-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 79°C
• Boiling Point: 330℃
• Flash Point: 153℃
• Appearance: /
• Density: 1.491
• Vapor Pressure: 0.000171mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: ?20°C
• PKA: -27.61±0.70(Predicted)
• Water Solubility: Insoluble in water
• Merck: 14,3047
• CAS DataBase Reference: DICHLORAMINE T(CAS DataBase Reference)
• NIST Chemistry Reference: DICHLORAMINE T(473-34-7)
• EPA Substance Registry System: DICHLORAMINE T(473-34-7)

Safety Data

• Hazard Codes: O,Xi
• Statements: 8-36/37/38
• Safety Statements: 17-26-36/37/39
• RIDADR: 1479
• WGK Germany: 3
• HazardClass: 5.1
• PackingGroup: I
• Hazardous Substances Data: 473-34-7(Hazardous Substances Data)

Usage

Uses

N,N-Dichloro-p-toluenesulfonamide (TsNCl2) can be used as:???????? A nitrogen source for the preparation of aziridines from electron-deficient α,β-unsaturated alkenes in the presence of palladium catalyst.?????? A reagent in the synthesis of dichlorohaloamines by aminohalogenation of functionalized olefins using copper(I) chloride or 4-dimethylaminopyridine (DMAP) catalyst.??????? A chlorinating agent in the regioselective synthesis of α-mono chlorosulfoxides from dialkyl sulfoxides or alkyl aryl sulfoxides.

Purification Methods

Crystallise it from pet ether (b 60-80o) or CHCl3/pet ether. Dry it in air <55o and store in the dark. It is soluble in CHCl3 (~1:1), *C6H6 (~1:1) and CCl4 (~1:2.5). It is a germicide and antibacterial as it readily liberates chlorine, and it should not smell strongly of chlorine; otherwise it should be purified. Alternatively dissolve ~15g of reagent in 75mL of hot acetic acid and precipitate it by addition of 37mL of N/10 bleaching powder solution (NaOCl), filter off, wash it with a dilute solution of the latter, dry as above (m 78-84o) and recrystallise it. “Sharp drying” will decompose it. [Orton & Bradfield J Chem Soc 993 1927, Krauss & Crede J Am Chem Soc 39 2720 1917, Soper J Chem Soc 1899 1924.] [see also chloramine-T (monochloramine T Na salt) in “Metal-organic Compounds”, Chapter 5]. [Beilstein 11 H I07, 11 I 27, 11 II 63, 11 III 301.]

InChI:InChI=1/C7H7Cl2NO2S/c1-6-2-4-7(5-3-6)13(11,12)10(8)9/h2-5H,1H3

Upstream product

• 127-65-1 chloroamine-T 
• 87905-16-6 N-(p-toluenesulfonyl)-2-pyridinesulfenamide 
• 70-55-3 toluene-4-sulfonamide 

Downstream Products

• 2866-82-2 N-(4-chlorophenyl)benzamide 
• 1020-39-9 N-(2-chlorophenyI)benzamide 
• 539-03-7 N-(4-chlorophenyl)acetamide 
• 614-61-9 (2-chlorophenoxy)acetic acid 
• 122-88-3 4-Chlorophenoxyacetic acid 
• 126383-31-1 C₁₅H₂₂Cl₂N₂O₅SSi 
• 126383-35-5 N,N-Bis-[2-chloro-2-(2,8,9-trioxa-5-aza-1-sila-bicyclo[3.3.3]undec-1-yl)-ethyl]-4-methyl-benzenesulfonamide 
• 51608-61-8 (E)-N-(2,2,2-trichloroethylidene)-4-methylbenzenesulfonamide 
• 623-12-1 4-chloromethoxybenzene 
• 766-51-8 2-Chloroanisole 
• 622-50-4 4-Acetamido-1-iodobenzene 
• 2596-93-2 2-chloro-N-phenylformamide 
• 2617-79-0 N-(4-chlorophenyl)formamide 
• 70-55-3 toluene-4-sulfonamide 

Relevant articles and documents

Conversion of nucleophilic halides to electrophilic halides: Efficient and selective halogenation of azinones, amides, and carbonyl compounds using metal halide/lead tetraacetate

AlCl3/Pb(OAc)4 and ZnBr2/Pb(OAc) 4 are efficient electrophilic N- and α-C-halogenating agents. A variety of azinones, amides and carbonyl compounds were chemoselectively and regioselectively N-, or α-C-halogenated in good to excellent yield using AlCl3/Pb(OAc)4 and ZnBr2/Pb(OAc)4 in acetonitrile. Georg Thieme Verlag Stuttgart.

Kinetic and Mechanistic Studies of Indigocarmine Oxidation by Chloramine-T and Chlorine in Acidic Buffer Media

Oxidations of indigocarmine (IC) by chloramine-T (CAT) and aqueous chlorine (HOCl) in acidic buffer media, pH 2-6, have been kinetically studied at 30 deg C using spectrophotometry.The CAT reaction rate shows a first-order dependence on 0 and an inverse fractional order on .The effect of on the rate is strongly pH dependent with a variable order of 1-2 on 0 in the pH range 6-2.The chlorine reaction rate follows first-order in 0 and 0 each in the pH range 6-2.Addition of halide ions and variation of ionic strength of the medium have no influence on the reaction rate.There is a negative effect of dielectric constant of the solvent.The kinetics of the IC oxidation with CAT at pH 6 and of that with HOCl at pHs 2-6 are similar suggesting similarity in their rate determining steps.A two-pathway mechanism for the CAT reaction and a one-pathway mechanism for the HOCl reaction, consistent with the kinetic data, have been proposed.Activation parameters have been calculated using the Arrhenius and Erying plots.

Kinetics and Mechanism of Oxidation of Hyponitrous Acid by Chloramine-T in Aqueous Perchloric Acid

The redox reaction between hyponitrous acid and chloramine-T (CAT) occurs as follows: 4RNHCl + H2N2O2 + 4H2O --> 4RNH2 + 2HNO3 + 4HCl.The rate has second order dependence in and complex dependence in and .It has inverse dependence on p-toluenesulphonamide (PTS), one of the products.The mechanism and the rate law are found to be slightly different in the two acid ranges, viz. from 0.007-0.1 mol dm-3 and 0.75-2.0 mol dm-3 HClO4.Dichloramine-T (DCT) is the reactive intermediate of CAT.Perhaps DCT exists in two forms, one of which is very reactive.