6461-77-4

Basic information

• Product Name: 1,4-Benzenedisulfonyl dichloride
• Synonyms: 1,4-Benzenedisulfonyl dichloride
• CAS NO: 6461-77-4
• Molecular Formula: C₆H₄Cl₂O₄S₂
• Molecular Weight: 275.12956
• Mol File: 6461-77-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: 138 °C
• Boiling Point: 375.549 °C at 760 mmHg
• Flash Point: 180.926 °C
• Appearance: /
• Density: 1.691 g/cm³
• CAS DataBase Reference: 1,4-Benzenedisulfonyl dichloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Benzenedisulfonyl dichloride(6461-77-4)
• EPA Substance Registry System: 1,4-Benzenedisulfonyl dichloride(6461-77-4)

Safety Data

• Hazardous Substances Data: 6461-77-4(Hazardous Substances Data)

Usage

General Description

1,4-Benzenedisulfonyl dichloride is a chemical compound that is used as a crosslinking agent and as a building block in organic synthesis. It is a white crystalline powder that is soluble in organic solvents and is highly reactive due to the presence of two sulfonyl chloride groups. It is commonly used in the production of polymers, particularly in the manufacture of nylon, where it is used to introduce crosslinking functionality. Additionally, it is utilized in the preparation of pharmaceuticals and agricultural chemicals. However, it is important to handle 1,4-Benzenedisulfonyl dichloride with caution as it is corrosive and can cause severe irritation to the skin, eyes, and respiratory system.

Synthetic route

benzene-1,4-dithiol (624-39-5) → benzene-1,4-disulfonyl chloride (6461-77-4)

Conditions	Yield
With chlorine; acetic acid
Multi-step reaction with 4 steps 1: alkali 2: nitric acid 3: concentrated hydriodic acid 4: glacial acetic acid; chlorine View Scheme
Multi-step reaction with 5 steps 1: alkali 2: chloroform; bromine 3: diluted alkaline solution 4: concentrated hydriodic acid 5: glacial acetic acid; chlorine View Scheme
Multi-step reaction with 3 steps 1: alkali 2: chloroform; iodine 3: glacial acetic acid; chlorine View Scheme

1,4-bis-(diiodo-methyl-λ4-sulfanyl)-benzene → benzene-1,4-disulfonyl chloride (6461-77-4)

Conditions	Yield
With chlorine; acetic acid

dipotassium p-benzenedisulfonate (16056-13-6) → benzene-1,4-disulfonyl chloride (6461-77-4)

Conditions	Yield
With phosphorus pentachloride

p-benzenedisulfonate potassium → benzene-1,4-disulfonyl chloride (6461-77-4)

Conditions	Yield
With phosphorus pentachloride

potassium salt of/the/ p-benzenedisulfonic acid → benzene-1,4-disulfonyl chloride (6461-77-4)

Conditions	Yield
With phosphorus pentachloride; phosphorus trichloride

sodium-salt of/the/ benzene-1,4-disulfonic acid → benzene-1,4-disulfonyl chloride (6461-77-4)

Conditions	Yield
With chlorosulfonic acid

p-sulfobenzenediazonium chloride (6118-33-8) → benzene-1,4-disulfonyl chloride (6461-77-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / SO2 / CuCl / aq. HCl; acetic acid / 3 h / 45 °C 2: phosphorus pentachloride View Scheme

1,4-Bis(methylthio)benzene (699-20-7) → benzene-1,4-disulfonyl chloride (6461-77-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: nitric acid 2: concentrated hydriodic acid 3: glacial acetic acid; chlorine View Scheme
Multi-step reaction with 4 steps 1: chloroform; bromine 2: diluted alkaline solution 3: concentrated hydriodic acid 4: glacial acetic acid; chlorine View Scheme
Multi-step reaction with 2 steps 1: chloroform; iodine 2: glacial acetic acid; chlorine View Scheme

1,4-bis(methylsulfinyl)benzene (90953-82-5, 150513-92-1) → benzene-1,4-disulfonyl chloride (6461-77-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated hydriodic acid 2: glacial acetic acid; chlorine View Scheme

1,4-bis-(dibromo-methyl-λ4-sulfanyl)-benzene → benzene-1,4-disulfonyl chloride (6461-77-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: diluted alkaline solution 2: concentrated hydriodic acid 3: glacial acetic acid; chlorine View Scheme

benzene-1,4-disulfonyl chloride (6461-77-4) + 2,4-difluoro-1-benzenesulfonamide (13656-60-5) → 4-(N-((2,4-difluorophenyl)sulfonyl)sulfamoyl)benzenesulfonyl chloride

Conditions	Yield
With triethylamine In acetonitrile at 0℃;	91%

benzene-1,4-disulfonyl chloride (6461-77-4) + C68H81N13O10*C2HF3O2 → C142H164N26O24S2

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one for 45h; Substitution;	81%

benzene-1,4-disulfonyl chloride (6461-77-4) + hexan-1-ol (111-27-3) → benzene-1,4-disulfonicacid-di-n-hexyl-ester (82965-01-3)

Conditions	Yield
With sodium	78%

benzene-1,4-disulfonyl chloride (6461-77-4) + Ac-Glu(OtBu)-Tyr-Leu-Arg(Pmc)-NH2 (192052-76-9) → C98H142N16O26S4 + Ac-Glu(OtBu)-Tyr[SO2C6H4(4-SO3H)]-Leu-Arg(Pmc)-NH2

Conditions	Yield
With Tris buffer In 1,4-dioxane for 24h; Ambient temperature;	A 22% B 53%

benzene-1,4-disulfonyl chloride (6461-77-4) + C68H81N13O10*C2HF3O2 → 4-{(3S,4S)-3,4-Bis-[((1R,2R)-2-{2-[4-(2-{ethyl-[4-(4-nitro-phenylazo)-phenyl]-amino}-ethoxy)-phenyl]-ethylcarbamoyl}-cyclohexanecarbonyl)-amino]-pyrrolidine-1-sulfonyl}-benzenesulfonic acid

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one for 45h; Substitution;	38%

pyridine (110-86-1) + 2-aminopyridine (504-29-0) + benzene-1,4-disulfonyl chloride (6461-77-4) → N,N'-di-[2]pyridyl-benzene-1,4-disulfonamide (71862-98-1)

Conditions	Yield
With benzene

benzene-1,4-disulfonyl chloride (6461-77-4) + sodium methylate (124-41-4) → benzol-1,4-disulfonsaeure dimethylester (33301-74-5)

Conditions	Yield
With benzene

benzene-1,4-disulfonyl chloride (6461-77-4) + dimethyl amine (124-40-3) → tetra-N-methyl-benzene-1,4-disulfonamide (103393-65-3)

benzene-1,4-disulfonyl chloride (6461-77-4) + diethylamine (109-89-7) → tetra-N-ethyl-benzene-1,4-disulfonamide (108620-77-5)

benzene-1,4-disulfonyl chloride (6461-77-4) → Benzol-disulfonsaeure-(1,4)-diazid (53965-92-7)

Conditions	Yield
With sodium azide

benzene-1,4-disulfonyl chloride (6461-77-4) → 1,4-Benzoldisulfonylfluorid (35426-72-3)

Conditions	Yield
With ion-exchange resin - form> In acetonitrile

benzene-1,4-disulfonyl chloride (6461-77-4) → 4-Chlorosulfonyl-benzenesulfonic acid (134187-88-5)

Conditions	Yield
With sodium acetate; acetic acid at 25℃; Rate constant; k = 1.80E-3/sec;

benzene-1,4-disulfonyl chloride (6461-77-4) + cyclohexylamine (108-91-8) → 1,4-Benzoldisulfonsaeure-dicyclohexylamid (53965-95-0)

benzene-1,4-disulfonyl chloride (6461-77-4) + aniline (62-53-3) → benzol-1,4-disulfonsaeuredianilid (53965-93-8)

benzene-1,4-disulfonyl chloride (6461-77-4) + methyl iodide (74-88-4) → 1,4-Bis(methylthio)benzene (699-20-7)

Conditions	Yield
(i) phosphorus, (ii) /BRN= 969135/, NaOEt, EtOH; Multistep reaction;

hydrogenchloride (7647-01-0) + benzene-1,4-disulfonyl chloride (6461-77-4) + tin → benzene-1,4-dithiol (624-39-5)

ethanol (64-17-5) + benzene-1,4-disulfonyl chloride (6461-77-4) + zinc → benzene-1,4-disulfinic acid (147139-87-5)

benzene-1,4-disulfonyl chloride (6461-77-4) → 4-Sulfino-benzenesulfonic acid hexyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / 1.) sodium 2: 76 percent / tetrabutyl-ammonium bromid / acetonitrile / 18 - 20 °C / electroreduction View Scheme

benzene-1,4-disulfonyl chloride (6461-77-4) → C18H34N2O4P2S8 (111297-07-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaN3 View Scheme

Upstream product

• 90953-82-5 1,4-bis(methylsulfinyl)benzene 
• 699-20-7 1,4-Bis(methylthio)benzene 
• 16056-13-6 dipotassium p-benzenedisulfonate 
• 624-39-5 benzene-1,4-dithiol 
• 6118-33-8 p-sulfobenzenediazonium chloride 

Downstream Products

• 624-39-5 benzene-1,4-dithiol 
• 120830-49-1 N,N'-(benzene-1,4-disulfonyl)-bis-imidophosphoric acid hexaphenyl ester 
• 111297-07-5 C₁₈H₃₄N₂O₄P₂S₈ 
• 147139-87-5 benzene-1,4-disulfinic acid 
• 699-20-7 1,4-Bis(methylthio)benzene 
• 53965-93-8 benzol-1,4-disulfonsaeuredianilid 
• 53965-95-0 1,4-Benzoldisulfonsaeure-dicyclohexylamid 
• 82965-01-3 benzene-1,4-disulfonicacid-di-n-hexyl-ester 
• 134187-88-5 4-Chlorosulfonyl-benzenesulfonic acid 
• 35426-72-3 1,4-Benzoldisulfonylfluorid 
• 53965-92-7 Benzol-disulfonsaeure-(1,4)-diazid 
• 108620-77-5 tetra-N-ethyl-benzene-1,4-disulfonamide 
• 103393-65-3 tetra-N-methyl-benzene-1,4-disulfonamide 
• 71862-98-1 N,N'-di-[2]pyridyl-benzene-1,4-disulfonamide 

Relevant articles and documents

STUDIEN ZUM VORGANG DER WASSERSTOFFUEBERTRAGUNG 62. HERSTELLUNG UND ELEKTROREDUKTIVE SPALTUNG EINIGER ARYLDISULFONSAEUREDERIVATE

Benzene-disulfonylchlorides were converted to the corresponding dialkyl- and diphenylesters, N-alkyl- and N-aryl disulfonamides.The half-wave-potentials E11/2 and E21/2 were measured and the products obtained on potentiostatic fission at E11/2 were isolated and characterized.The electroreduction of benzene-1,4-disulfonic acid-diphenylester in methanol yields phenol in quantity approximately corresponding to the current passed, but no corresponding quantity of sulfinic acid.In dry acetonitrile, benzene-1,4-disulfonic acid diesters and diamides undergo potentiostatic fission (at E11/2) in good chemical and current yields, giving the corresponding monosulfonate-sulfinic acid or monosulfonamide-sulfinic acid and alcohol or amine.The passage of further electrical current reduces the sulfinic acids to other, as yet undetermined, products.