52499-14-6

Basic information

• Product Name: 4-DODECYLBENZENESULFONYL CHLORIDE
• Synonyms: P-DODECYLBENZENESULFONYL CHLORIDE;4-DODECYLBENZENESULFONYL CHLORIDE;p-dodecylbenzenesulphonyl chloride;4-Dodecylbenzenesulfonic acid chloride;4-Dodecylbenzene-1-sulfonyl chloride;Benzenesulfonylchloride, 4-dodecyl-
• CAS NO: 52499-14-6
• Molecular Formula: C₁₈H₂₉ClO₂S
• Molecular Weight: 344.94
• EINECS: 257-966-3
• Product Categories: pharmacetical
• Mol File: 52499-14-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 33 °C
• Boiling Point: 427.1 °C at 760 mmHg
• Flash Point: 212.1 °C
• Appearance: /
• Density: 1.064g/cm³
• Vapor Pressure: 4.18E-07mmHg at 25°C
• Refractive Index: 1.504
• CAS DataBase Reference: 4-DODECYLBENZENESULFONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-DODECYLBENZENESULFONYL CHLORIDE(52499-14-6)
• EPA Substance Registry System: 4-DODECYLBENZENESULFONYL CHLORIDE(52499-14-6)

Safety Data

• Hazardous Substances Data: 52499-14-6(Hazardous Substances Data)

Usage

General Description

4-Dodecylbenzenesulfonyl chloride is an organic compound commonly used as an intermediate in the production of surfactants and other industrial chemicals. It is a white to off-white solid that easily reacts with water and should be handled with care due to its potential to cause severe skin and eye irritation. This chemical is primarily used in the manufacturing of detergent formulations, as well as in the synthesis of polymers and other specialty chemicals. Its ability to lower the surface tension of water makes it valuable in a wide range of industrial applications, particularly in the production of household and industrial cleaning products.

InChI:InChI=1/C18H29ClO2S/c1-2-3-4-5-6-7-8-9-10-11-12-17-13-15-18(16-14-17)22(19,20)21/h13-16H,2-12H2,1H3

Synthetic route

potassium 4-dodecylbenzenesulfonate (14564-74-0) → p-dodecylbenzenesulfonyl chloride (52499-14-6)

Conditions	Yield
With trichlorophosphate at 20 - 170℃;	97%

para-dodecylbenzenesulfonic acid (121-65-3) → p-dodecylbenzenesulfonyl chloride (52499-14-6)

Conditions	Yield
With pyridine; thionyl chloride at 60℃; for 2h;
With trichlorophosphate at 120℃; for 4h;	51.3 g

1-dodecylbenzene (123-01-3) → p-dodecylbenzenesulfonyl chloride (52499-14-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / 1 h / 90 °C 2: trichlorophosphate / 20 - 170 °C View Scheme

p-dodecylbenzenesulfonyl chloride (52499-14-6) → 4-dodecyl-benzenesulfonic acid amide (34778-78-4)

Conditions	Yield
With ammonium hydroxide In chloroform at 20℃; for 2h;	99%

p-dodecylbenzenesulfonyl chloride (52499-14-6) + zinc(II) chloride (7646-85-7) → zinc p-dodecylbenzenesulfinate

Conditions	Yield
With sodium hydroxide; sodium sulfite In water at 70 - 100℃; for 5h; pH=7 - 8; Reagent/catalyst; pH-value;	97.5%

p-dodecylbenzenesulfonyl chloride (52499-14-6) → p-dodecylbenzenethiol (20025-90-5)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 22h; Heating;	97%

2-Amino-5-t-butyl-1,3,4-thiadiazole (39222-73-6) + p-dodecylbenzenesulfonyl chloride (52499-14-6) → N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-4-dodecylbenzenesulfonamide (1191951-60-6)

Conditions	Yield
With pyridine at 0 - 95℃;	87%
With pyridine at 95℃; for 1h;	86%

p-dodecylbenzenesulfonyl chloride (52499-14-6) + (1R,2R)-1,2-bis(3-nitrophenyl)ethane-1,2-diamine (1252644-48-6) → N-[(1R,2R)-2-amino-1,2-bis(3-nitrophenyl)ethyl]-4-dodecylbenzenesulfonamide (1408001-54-6)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 18.5h;	86%

5-methyl-1,3,4-thiadiazol-2-amine (108-33-8) + p-dodecylbenzenesulfonyl chloride (52499-14-6) → 4-dodecyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide (1191951-58-2)

Conditions	Yield
With pyridine at 95℃; for 1h;	84%
With pyridine at 0 - 95℃;

p-dodecylbenzenesulfonyl chloride (52499-14-6) → 4-dodecylbenzenesulphonyl azide (79791-38-1)

Conditions	Yield
With sodium azide In water; acetone at 10 - 30℃; Temperature; Flow reactor;	82.2%
With sodium azide In water; acetone at 20℃; for 11h;

p-dodecylbenzenesulfonyl chloride (52499-14-6) + (S,S,S)-2-azabicyclo<3.3.0>octane-3-carboxylic acid hydrochloride (87269-86-1) → (2S,3aS,6aS)-1-(4-Dodecyl-benzenesulfonyl)-octahydro-cyclopenta[b]pyrrole-2-carboxylic acid

Conditions	Yield
With sodium carbonate In tetrahydrofuran for 15h;	82%

(±)-trans-1,2-diaminocyclohexane + p-dodecylbenzenesulfonyl chloride (52499-14-6) → C24H42N2O2S

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; Cooling with ice;	82%

p-dodecylbenzenesulfonyl chloride (52499-14-6) + 1,2-diamino-benzene (95-54-5) → N-(2-aminophenyl)-4-dodecyl-benzenesulfonamide

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 3h;	81%

ethyl 5-amino-1,3,4-thiadiazole-2-carboxylate (64837-53-2) + p-dodecylbenzenesulfonyl chloride (52499-14-6) → ethyl 5-(4-dodecylphenylsulfonamido)-1,3,4-thiadiazole-2-carboxylate (1191951-63-9)

Conditions	Yield
With pyridine at 20 - 95℃; for 48.25h;	78%
With pyridine at 20℃; for 4.5h;	34%

p-dodecylbenzenesulfonyl chloride (52499-14-6) → 4-dodecylbenzenesulfonyl fluoride

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran; dichloromethane at 0 - 25℃; for 1h;	73%

p-dodecylbenzenesulfonyl chloride (52499-14-6) + aniline (62-53-3) → p-dodecyl-N-phenylbenzenesulfonamide (111370-45-7)

Conditions	Yield
With pyridine at 20℃; for 3h;	68%

D-myo-inositol (87-89-8) + p-dodecylbenzenesulfonyl chloride (52499-14-6) → DL-1-O-p-dodecylbenzenesulfonyl-myo-inositol + C42H68O10S2 (1448044-01-6)

Conditions	Yield
Stage #1: D-myo-inositol; p-dodecylbenzenesulfonyl chloride With triethylamine; lithium chloride In N,N-dimethyl acetamide at 20℃; Stage #2: With pyridine; chloro-trimethyl-silane In methanol; N,N-dimethyl acetamide at 20℃; for 3h; Stage #3: With trifluoroacetic acid In methanol; chloroform at 20℃; for 2h;	A 66% B 16%

p-dodecylbenzenesulfonyl chloride (52499-14-6) + 2-amino-5-hydroxymethyl-1,3,4-thiadiazole (56951-58-7) → 4-dodecyl-N-(5-(hydroxymethyl)-1,3,4-thiadiazol-2-yl)benzenesulfonamide (1191951-64-0)

Conditions	Yield
With pyridine at 20 - 95℃; for 48.25h;	65%
at 20℃; for 4.5h;	65%

5-amino-1, 3, 4-thiadiazole-2-sulfonamide (14949-00-9) + p-dodecylbenzenesulfonyl chloride (52499-14-6) → 5-(4-dodecylphenylsulfonamido)-1,3,4-thiadiazole-2-sulfonamide (1191951-78-6)

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 48h;	63%
With triethylamine In acetonitrile at 0 - 20℃;	39%

2-amino-5-ethyl-1,3,4-thiadiazole (14068-53-2) + p-dodecylbenzenesulfonyl chloride (52499-14-6) → 4-dodecyl-N-(5-ethyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide (1191951-59-3)

Conditions	Yield
With pyridine at 95℃; for 1h;	59%
With pyridine at 0 - 95℃;	59%

4-Methylbenzyl alcohol (589-18-4) + p-dodecylbenzenesulfonyl chloride (52499-14-6) → N-(4-methylbenzyl)-N,N-dimethylanilinium 4-dodecylbenzenesulfonate

Conditions	Yield
In 1,4-dioxane; N,N-dimethyl-aniline	53%

2-Amino-1,3,4-thiadiazolyl-5-acetic acid ethyl ester (88124-55-4) + p-dodecylbenzenesulfonyl chloride (52499-14-6) → ethyl 2-(5-(4-dodecylphenylsulfonamido)-1,3,4-thiadiazol-2-yl)acetate (1191951-62-8)

Conditions	Yield
With pyridine at 20 - 95℃; for 48.25h;	53%
With pyridine at 20℃; for 4.5h;	43%

[1,3,4]Thiadiazol-2-ylamin (4005-51-0) + p-dodecylbenzenesulfonyl chloride (52499-14-6) → ARC-183 (1191951-57-1)

Conditions	Yield
With pyridine	51%
With pyridine at 0 - 95℃;

p-dodecylbenzenesulfonyl chloride (52499-14-6) + (1S,3R,4R)-2-aza-bicyclo-[2.2.1]-heptane-3-carboxylic acid (171754-03-3) → (1S,3R,4R)-2-(4-Dodecyl-benzenesulfonyl)-2-aza-bicyclo[2.2.1]heptane-3-carboxylic acid

Conditions	Yield
With sodium carbonate In tetrahydrofuran at 25℃; for 72h;	46%

p-dodecylbenzenesulfonyl chloride (52499-14-6) → decafluoro-4-pentacosafluorododecyl-cyclohexanesulfonyl fluoride

Conditions	Yield
With hydrogen fluoride Electrolysis;

p-dodecylbenzenesulfonyl chloride (52499-14-6) + C20H28N2O4 (243670-27-1) → C56H84N2O8S2

Conditions	Yield
With potassium carbonate Acylation;

p-dodecylbenzenesulfonyl chloride (52499-14-6) → 4-dodecylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-D-glucopyranoside

Conditions	Yield
Multi-step reaction with 2 steps 1: 97 percent / LiAlH4 / tetrahydrofuran / 22 h / Heating 2: BF3*Et2O / CH2Cl2 View Scheme

p-dodecylbenzenesulfonyl chloride (52499-14-6) → C52H76N2O8S2

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 2: LiOH / tetrahydrofuran; H2O; ethanol View Scheme

C26H35F2N2O8P (888214-02-6) + p-dodecylbenzenesulfonyl chloride (52499-14-6) → C44H63F2N2O10PS

Conditions	Yield
With potassium carbonate In tetrahydrofuran; water

α-hydroxyimino-3,4-dimethoxybenzyl cyanide + p-dodecylbenzenesulfonyl chloride (52499-14-6) → α-(4-dodecylphenylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide

Conditions	Yield
In tetrahydrofuran; ethyl acetate; triethylamine

Upstream product

• 123-01-3 1-dodecylbenzene 
• 121-65-3 para-dodecylbenzenesulfonic acid 
• 14564-74-0 potassium 4-dodecylbenzenesulfonate 

Downstream Products

• 1271729-65-7 N-(5-(5-chloropentyl)-1,3,4-thiadiazol-2-yl)-4-dodecyl benzenesulfonamide 
• 1178893-79-2 N-(5-(5-bromopentyl)-1,3,4-thiadiazol-2-yl)-4-dodecylbenzenesulfonamide 
• 1191951-78-6 5-(4-dodecylphenylsulfonamido)-1,3,4-thiadiazole-2-sulfonamide 
• 1191951-63-9 ethyl 5-(4-dodecylphenylsulfonamido)-1,3,4-thiadiazole-2-carboxylate 
• 1191951-58-2 4-dodecyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide 
• 1191951-57-1 ARC-183 
• 1191951-59-3 4-dodecyl-N-(5-ethyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide 
• 1191951-60-6 N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-4-dodecylbenzenesulfonamide 
• 1191951-64-0 4-dodecyl-N-(5-(hydroxymethyl)-1,3,4-thiadiazol-2-yl)benzenesulfonamide 
• 1191951-62-8 ethyl 2-(5-(4-dodecylphenylsulfonamido)-1,3,4-thiadiazol-2-yl)acetate 
• 1191951-61-7 2-(5-(4-dodecylphenylsulfonamido)-1,3,4-thiadiazol-2-yl)acetic acid 
• 1191951-93-5 4-dodecyl-N-(5-(5-(methylamino)pentyl)-1,3,4-thiadiazol-2-yl)benzenesulfonamide 
• 1191951-85-5 4-dodecyl-N-(5-(5-(methyl(7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)pentyl)-1,3,4-thiadiazol-2-yl)benzenesulfonamide 
• 68506-75-2 methyl para-dodecylbenzenesulfonate 

Relevant articles and documents

COLORED CHARGED SILSESQUIOXANES

The present invention provides salts of a cation and an anion, wherein the cation comprises (i) a silsesquioxane moiety of formula (ii) a chromophoric moiety D, which may which may be substituted with one or more substituents selected from the group consisting of C1-10-alkyl, phenyl, halogen, OC1-6-alkyl, OH, NH2 and NO2, and (iii) a moiety of formula wherein L4 is C1-20-alkylene, phenylene-C1-20-alkylene or C1-20-alkylene-phenylene-C1-20alkylene, R11, R12, R13 and R14 are independently from each other hydrogen or C1-4-alkyl, R15, R16, R17 and R18 are independently from each other C1-4-alkyl, R19 is C1-20-alkyl, which may be substituted with phenyl, O—C1-6-alkyl or NO2, and d is an integer from 1 to 25, and electrophoretic devices comprising the salts.

SMALL MOLECULE INHIBITORS OF THE PLECKSTRIN HOMOLOGY DOMAIN AND METHODS FOR USING SAME

Pleckstrin homology domain binding compounds, pharmaceutical compositions including such compounds, and methods for their use are described herein.