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2-Naphthalenesulfonyl Chloride

  • Name 2-Naphthalenesulfonyl Chloride
  • EINECS202-219-9
  • CAS No. 93-11-8
  • Density1.414 g/cm3
  • PSA42.52000
  • LogP3.84810
  • Solubilityinsoluble in water
  • Melting Point74-76 °C(lit.)
  • FormulaC10H7ClO2S
  • Boiling Point371.3 °C at 760 mmHg
  • Molecular Weight226.683
  • Flash Point178.4 °C
  • Transport InformationUN 3261 8/PG 2
  • Appearancelight yellow to beige powder
  • Safety26-36/37/39-45-27
  • Risk Codes34
  • Molecular Structure
    Molecular Structure of 93-11-8 (2-Naphthalenesulfonyl chloride)
  • Hazard SymbolsCorrosiveC
  • SynonymsCorrosiveC
  • Article Data51

2-Naphthalenesulfonyl Chloride Synthetic route

5586-15-2

bis(2-naphthyl)disulfide

93-11-8

2-Naphthalenesulfonyl chloride

Conditions
ConditionsYield
With dihydrogen peroxide; zirconium(IV) chloride In water; acetonitrile at 25℃; for 0.0166667h;98%
With N,N,N',N'-tetrachlorobenzene-1,3-disulphonamide; tetrabutyl-ammonium chloride; water In acetonitrile at 0 - 20℃; for 0.333333h;98%
With trichloroisocyanuric acid; tetrabutylammomium bromide; water In acetonitrile at 0 - 20℃; for 0.333333h;98%
91-60-1

2-Naphthalenethiol

93-11-8

2-Naphthalenesulfonyl chloride

Conditions
ConditionsYield
With N,N,N',N'-tetrachlorobenzene-1,3-disulphonamide; tetrabutyl-ammonium chloride; water In acetonitrile at 0 - 20℃; for 0.333333h;98%
With trichloroisocyanuric acid; water In acetonitrile at 0 - 20℃; for 0.333333h;98%
With dihydrogen peroxide; zirconium(IV) chloride In water; acetonitrile at 25℃; for 0.0166667h;97%
532-02-5

2-naphthalenesulfonic acid sodium salt

93-11-8

2-Naphthalenesulfonyl chloride

Conditions
ConditionsYield
With trichlorophosphate In chloroform at 90℃; for 9h; Temperature; Solvent; Concentration;95.8%
With trichlorophosphate; N,N-dimethyl acetamide In sulfolane; acetonitrile at 68 - 72℃; for 0.25h;91%
With 1,3,5-trichloro-2,4,6-triazine; 18-crown-6 ether In acetone for 20h; Heating;89%
With chlorine-triphenylphosphine In acetonitrile for 15h; Ambient temperature;
120-18-3

naphthalene-2-sulfonate

93-11-8

2-Naphthalenesulfonyl chloride

Conditions
ConditionsYield
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine; potassium chloride at 25℃; for 0.0333333h; Neat (no solvent);94%
With 1,3,5-trichloro-2,4,6-triazine; triethylamine In acetone for 20h; Heating;88%
With thionyl chloride In diethyl ether Ambient temperature;
With triethylamine In acetone at 80℃; for 0.333333h; microwave irradiation;
7570-97-0

benzyl 2-naphthylsulfide

93-11-8

2-Naphthalenesulfonyl chloride

Conditions
ConditionsYield
With 1,3-dichloro-5,5-dimethylhydantoin; acetic acid In dichloromethane; water at 0 - 5℃; Inert atmosphere;86%
91-20-3

naphthalene

93-11-8

2-Naphthalenesulfonyl chloride

Conditions
ConditionsYield
With chlorosulfonic acid at 60℃;70%
With chlorosulfonic acid at 5 - 65℃;
127-65-1

chloroamine-T

91-60-1

2-Naphthalenethiol

A

N-chloro-N-(4-methylbenzenesulfonyl)-naphthalene-2-sulfinamide

B

93-11-8

2-Naphthalenesulfonyl chloride

Conditions
ConditionsYield
With N-chloro-succinimide In water; acetonitrile at 35℃; for 0.25h;A 64%
B 27%
26189-33-3

2,2-dinaphthylsulfone

A

91-58-7

2-chloronaphthalene

B

93-11-8

2-Naphthalenesulfonyl chloride

Conditions
ConditionsYield
With phosphorus pentachloride at 180 - 200℃;
580-13-2

2-bromonaphthalene

93-11-8

2-Naphthalenesulfonyl chloride

Conditions
ConditionsYield
Yield given. Multistep reaction;
β-naphthalenesulfonate of alkali

β-naphthalenesulfonate of alkali

93-11-8

2-Naphthalenesulfonyl chloride

Conditions
ConditionsYield
With phosphorus pentachloride

2-Naphthalenesulfonyl Chloride Specification

The 2-Naphthalenesulfonyl Chloride is an organic compound with the formula C10H7ClO2S. The IUPAC name of this chemical is naphthalene-2-sulfonyl chloride. With the CAS registry number 93-11-8 and EINECS 202-219-9, it is also named as Naphthalene-2-sulfonic acid chloride. The product's categories are Organic Building Blocks; Sulfonyl Halides; Sulfur Compounds. It is light yellow to beige powder which is insoluble in water and sensitive to moisture. In addition, this chemical  should be sealed in the container and stored in the dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.22; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.22; (4)ACD/LogD (pH 7.4): 3.22; (5)ACD/BCF (pH 5.5): 164.3; (6)ACD/BCF (pH 7.4): 164.3; (7)ACD/KOC (pH 5.5): 1341.39; (8)ACD/KOC (pH 7.4): 1341.39; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 42.52 Å2; (13)Index of Refraction: 1.643; (14)Molar Refractivity: 57.95 cm3; (15)Molar Volume: 160.2 cm3; (16)Polarizability: 22.97×10-24 cm3; (17)Surface Tension: 50.5 dyne/cm; (18)Density: 1.414 g/cm3; (19)Flash Point: 178.4 °C; (20)Enthalpy of Vaporization: 59.4 kJ/mol; (21)Boiling Point: 371.3 °C at 760 mmHg; (22)Vapour Pressure: 2.23E-05 mmHg at 25°C.

Preparation of 2-Naphthalenesulfonyl Chloride: It can be obtained by naphthalene-2-sulfonic acid ; sodium-salt. This reaction needs reagent POCl3, catalytic agent N,N-Dimethylacetamide and solvents acetonitrile, tetrahydrothiophene 1,1-dioxide at temperature of 68-72 °C. The reaction time is 15 min. The yield is 91%.

2-Naphthalenesulfonyl Chloride can be obtained by naphthalene-2-sulfonic acid ; sodium-salt

Uses of 2-Naphthalenesulfonyl Chloride: It is used in the determination of amines and used in organic synthesis. For example: it can react with aniline to get naphthalene-2-sulfonanilide. This reaction needs reagent Et3N and solvent CH2Cl2 at temperature of 20 °C. The yield is 95%.

2-Naphthalenesulfonyl Chloride can react with aniline to get naphthalene-2-sulfonanilide

When you are using this chemical, please be cautious about it as the following:
It can cause burns. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure. 
1. SMILES:ClS(=O)(=O)c2ccc1c(cccc1)c2
2. InChI:InChI=1/C10H7ClO2S/c11-14(12,13)10-6-5-8-3-1-2-4-9(8)7-10/h1-7H
3. InChIKey:OPECTNGATDYLSS-UHFFFAOYAP

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