1928-01-4

Basic information

• Product Name: naphthalene-1,5-disulfonyl chloride
• Synonyms: naphthalene-1,5-disulfonyl chloride;1,5-Naphthalenebis(sulfonic acid chloride);1,5-Naphthalenebis(sulfonyl chloride);1,5-Naphthalenedisulfonic acid dichloride;1,5-Naphthalenedisulfonyl chloride;Naphthalene-1,5-disulfonic acid dichloride;1,5-Naphthalenedisulfonyl dichloride
• CAS NO: 1928-01-4
• Molecular Formula: C₁₀H₆Cl₂O₄S₂
• Molecular Weight: 325.19
• Mol File: 1928-01-4.mol

Chemical Properties

• Melting Point: 183 °C
• Boiling Point: 446.2°Cat760mmHg
• Flash Point: 223.6°C
• Appearance: /
• Density: 1.651g/cm³
• Vapor Pressure: 9.78E-08mmHg at 25°C
• Refractive Index: 1.647
• CAS DataBase Reference: naphthalene-1,5-disulfonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: naphthalene-1,5-disulfonyl chloride(1928-01-4)
• EPA Substance Registry System: naphthalene-1,5-disulfonyl chloride(1928-01-4)

Safety Data

• Hazardous Substances Data: 1928-01-4(Hazardous Substances Data)

Usage

Uses

Used in Dye Industry:
Naphthalene-1,5-disulfonyl chloride is used as a sulfonating agent for the synthesis of dyes. Its ability to introduce sulfonic acid groups into organic molecules aids in the production of various dye compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, naphthalene-1,5-disulfonyl chloride serves as a key intermediate in the synthesis of various drug molecules. Its sulfonating properties enable the creation of new chemical entities with potential therapeutic applications.
Used in Agrochemical Industry:
Naphthalene-1,5-disulfonyl chloride is utilized as a sulfonating agent in the development of agrochemicals. Its reactivity allows for the introduction of sulfonic acid groups into organic molecules, leading to the formation of compounds with pesticidal or herbicidal properties.
Used in Polymer Manufacturing:
naphthalene-1,5-disulfonyl chloride is employed in the manufacturing of polymers and specialty chemicals. The introduction of sulfonic acid groups through naphthalene-1,5-disulfonyl chloride enhances the properties of polymers, making them suitable for various applications.
Used in Organic Synthesis:
Naphthalene-1,5-disulfonyl chloride is a versatile reagent in organic synthesis, where it is used to introduce sulfonic acid groups into a wide range of organic molecules. This modification can alter the physical, chemical, and biological properties of the target compounds, expanding their potential applications in various fields.

InChI:InChI=1/C10H6Cl2O4S2/c11-17(13,14)9-5-1-3-7-8(9)4-2-6-10(7)18(12,15)16/h1-6H

Upstream product

• 91-20-3 naphthalene 
• 1655-29-4 disodium 1,5-naphthalenedisulfonate 
• 7790-94-5 chlorosulfonic acid 
• 56-23-5 tetrachloromethane 
• 81-04-9 naphthalene-1,5-disulfonate 

Downstream Products

• 5325-88-2 1,5-naphthalenedithiol 
• 102704-74-5 N,N'-diphenyl-naphthalene-1,5-disulfonamide 
• 1825-30-5 1,5-dichloronaphthalene 
• 10075-74-8 1,5-bis(methylthio)naphthalene 
• 27715-44-2 1,5-diiodonaphthalene 

Relevant articles and documents

Synthesis and biocidal activity of some naphthalene-based cationic surfactants

In this study, different cationic surfactants were prepared by reacting dodecyl bromide with tertiary amines to produce a series of quaternary ammonium salts that were converted subsequently to stannous and cobalt cationic complexes via complexing them with stannous (II) or cobalt (II) ions. Surface properties such as surface- and interfacial-tension, and the emulsifying power of these surfactants were investigated. The surface parameters including critical micelle concentration, maximum surface excess, minimum surface area, tension lowering efficiency and effectiveness were studied. The free energy of micellization and adsorption were calculated. Antimicrobial activity was determined via the inhibition zone diameter of the prepared compounds, which was measured against six strains of a representative group of microorganisms. The antimicrobial activity of some of the prepared surfactants against sulfate reducing bacteria was determined by the dilution method. FTIR spectra, elemental analysis and a H1 NMR spectrum were examined to confirm compound structure and purity. The results obtained indicate that these compounds have good surface properties and good biocidal effect on broad spectrum of micro organisms. AOCS 2011.

Molecule 1,5-C10H6(SO2Cl)2 as prototype of conformational properties of naphthalene sulfonyl derivatives

Conformational composition of the vapor (T?=?413(5)?K) and the conformer structures of 1,5-naphthalenedisulfonylchloride (1,5-NaphDSC) have been studied by a combined gas-phase electron diffraction and mass spectrometry (GED/MS) method complemented by quantum chemical calculations. According to quantum chemical calculations at DFT/B3LYP/cc-pVTZ and MP2/cc-pVTZ theory levels, the molecule 1,5-NaphDSC possesses four conformers differing mutual orientation of the two SO2Cl groups. GED data clearly indicate that only two conformers, whose structures are characterized by deviation of two S[sbnd]Cl bonds from perpendicular position relative to the plane of the naphthalene skeleton (syn-symmetry C2 and anti-symmetry Ci), are present in vapor at 413?K. The following geometrical parameters of these conformers were obtained from the experiment (? and degrees; uncertainties are in parentheses): rh1(C[sbnd]H)?=?1.098(9), rh1(C[sbnd]C)?=?1.405(3), rh1(C[sbnd]S)?=?1.781(4), rh1(S[sbnd]O)?=?1.426(3), rh1(S[sbnd]Cl)?=?2.056(4), ∠C[sbnd]CS[sbnd]C?=?122.9(1), ∠CS[sbnd]S[sbnd]Cl?=?101.8(6); C9[sbnd]C1[sbnd]S[sbnd]Cl?=?71.2(12), C10[sbnd]C5[sbnd]S[sbnd]Cl?=?71.2(12)-syn conformer; C9[sbnd]C1[sbnd]S[sbnd]Cl?=?71.2(12), C10[sbnd]C5[sbnd]S[sbnd]Cl?=??71.2(12) -anti-conformer. The presence of C9Hn+ ions in the mass spectra of naphthalenesulfonyl chlorides, which are absent in the mass spectrum of naphthalene, may be attributed to the weakening of two C[sbnd]C bonds adjacent to the substituent of the naphthalene skeleton. This reflects in the geometric parameters of 1,5-NaphDSC. The barriers to internal rotation of sulfonyl chloride groups were calculated. It is shown that the low-energy syn- and anti-conformers are structurally rigid, in contrast to high-energy conformers with one or two S[sbnd]Cl bonds, lying in the plane of the naphthalene skeleton. The dependence of C1[sbnd]C2, C[sbnd]S, S[sbnd]Cl bond lengths from SO2Cl groups orientation relative to naphthalene skeleton is discussed in terms of NBO-analysis of electron density distribution. The relationship between conformational properties of molecule and some physicochemical characteristics of the 1,5-NaphDSC compound is discussed.

Dependence of single-molecule conductance on molecule junction symmetry

The symmetry of a molecule junction has been shown to play a significant role in determining the conductance of the molecule, but the details of how conductance changes with symmetry have heretofore been unknown. Herein, we investigate a naphthalenedithiol single-molecule system in which sulfur atoms from the molecule are anchored to two facing gold electrodes. In the studied system, the highest single-molecule conductance, for a molecule junction of 1,4-symmetry, is 110 times larger than the lowest single-molecule conductance, for a molecule junction of 2,7-symmetry. We demonstrate clearly that the measured dependence of molecule junction symmetry for single-molecule junctions agrees with theoretical predictions.

Synthesis of C2-symmetrical bis(1,2-hydroxy sulfonamide) ligands and application in the enantioselective addition of dialkylzinc to aldehydes

The preparation of several C2-symmetric disulfonamides derived from 1,2-amino alcohols and disulfonyl derivatives, as well as their use in the titanium tetraisopropoxide-promoted enantioselective additions of dialkylzinc to aldehydes are described. The enantiomeric ratio is up to 96:4, the best results being obtained for aromatic aldehydes with electron-donating groups in the para-position. There are some differences in the enantioselectivity depending on the relative positioning of the amino alcohol moieties in the chiral ligand, the 1,3-disulfonyl derivative being the best system. In the case of para-substituted benzaldehyde derivatives, a negative relationship between the electron-withdrawing character of the para-substituted group and the enantioselectivity of the addition was seen, whereas the more electronic-donating character the substituent has, the higher the observed enantioselectivity.

Preparation of 2-chloro-5-methyl-pyridine

A process for the preparation of 2-chloro-5-methylpyridine of the formula STR1 which comprises reacting 3-methyl-pyridine-1-oxide of the formula STR2 with a chlorinating agent of the formula STR3 in which R1 represents alkyl, halogenoalkyl, cycloalkyl, optionally substituted aryl, NR2 R3 or OR4 in which R2 and R3 individually represent alkyl, cycloalkyl or aryl or together represent alkanediyl or oxaalkanediyl and R4 represents alkyl, cycloalkyl or optionally substituted aryl, in the presence of a basic organic nitrogen compound and in the presence of a diluent at a temperature between about -20° C. and +150° C.

Process for the preparation of aromatic sulfonyl chlorides

A process for the preparation of aromatic sulfonyl chlorides of the formula I STR1 in which R1, R2 and R3 are identical or different and are hydrogen, fluorine, chlorine, bromine or iodine atoms, alkyl(C1 -C4), acetamido, nitro or carboxyl groups, or R1 and R2 together form an aromatic or heteroaromatic ring having 5 or 6 ring members, which can be substituted by fluorine, chlorine, bromine or iodine atoms, alkyl(C1 -C4), acetamido, nitro or carboxyl groups, by reaction of aromatic compounds of the formula II STR2 in which R1, R2 and R3 have the abovementioned meanings, with chlorosulfonic acid in excess or with chlorosulfonic acid or oleum and thionyl chloride, by reacting in the presence of sulfamic acid as a catalyst.

OLIGODEOXYRIBONUCLEOTIDE SYNTHESIS BY USE OF S,S-DIPHENYL DEOXYRIBONUCLEOSIDE 3'-PHOSPHORODITHIOATES AND BIFUNCTIONAL CONDENSING REAGENTS IN THE PHOSPHOTRIESTER APPROACH

Four kinds of arenedisulphonyl chlorides as condensing reagents for oligodeoxyribonucleotide synthesis have been synthesised and their condensing abilities were examined in the synthesis of thymidylyl(3'-5')thymidine.Among them, mesitylenedisulphonyl chlo

Aromatic sulfonamide sulfonyl chloride compounds

An aromatic sulfonamide sulfonyl chloride, useful as an intermediate in the preparation of cyan dye-releasing redox compounds for diffusion transfer photographic materials, represented by the following general formula (I) STR1 wherein A represents a divalent benzene nucleus or a divalent naphthalene nucleus, in which in each nucleus the bonding thereto is symmetrical, and a method for the synthesis thereof comprising reacting an aromatic disulfonyl chloride represented by the formula (IIa) or (IIb) STR2 wherein the two sulfonyl chloride groups are substituted at symmetrical positions on the benzene and the naphthylene ring, with 5-amino-1-naphthol.