2824-46-6

Basic information

• Product Name: 1,3-BENZOTHIAZOLE-2-SULFONYL CHLORIDE,97%
• Synonyms: 1,3-BENZOTHIAZOLE-2-SULFONYL CHLORIDE,97%;1,3-Benzothiazole-2-sulfonyl chloride;benzo[d]thiazole-2-sulfonyl chloride;Benzothiazole-2-sulfonyl chloride
• CAS NO: 2824-46-6
• Molecular Formula: C₇H₄ClNO₂S₂
• Molecular Weight: 233.69516
• Mol File: 2824-46-6.mol
• Article Data: 13

Chemical Properties

• Melting Point: 140.8℃
• Boiling Point: 398.39 °C at 760 mmHg
• Flash Point: 194.74 °C
• Appearance: /
• Density: 1.635 g/cm³
• PKA: -4.34±0.10(Predicted)
• CAS DataBase Reference: 1,3-BENZOTHIAZOLE-2-SULFONYL CHLORIDE,97%(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-BENZOTHIAZOLE-2-SULFONYL CHLORIDE,97%(2824-46-6)
• EPA Substance Registry System: 1,3-BENZOTHIAZOLE-2-SULFONYL CHLORIDE,97%(2824-46-6)

Safety Data

• Hazard Codes: C:Corrosive
• Statements: R34:Causes burns.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36/37/39:Wear suitabl
• Hazardous Substances Data: 2824-46-6(Hazardous Substances Data)

Usage

General Description

1,3-Benzothiazole-2-sulfonyl chloride, also known as BTSCl, is a chemical compound with a purity of 97%. 1,3-BENZOTHIAZOLE-2-SULFONYL CHLORIDE,97% is used in organic synthesis as a versatile building block for the preparation of various biologically active molecules and pharmaceuticals. It is a sulfonating agent that reacts with amines, alcohols, and phenols to form sulfonamides, sulfonate esters, and sulfonic acid derivatives, respectively. Additionally, it is used in the synthesis of dyestuffs, fluorescent brighteners, and as a corrosion inhibitor. It is a highly reactive and versatile chemical that has wide applicability in organic chemistry.

Synthetic route

2-Mercaptobenzothiazole (149-30-4) → benzothiazole-2-sulfonyl chloride (2824-46-6)

Conditions	Yield
With chlorine; acetic acid	97%
With hydrogenchloride; chlorine	71%
With hydrogenchloride; sodium hypochlorite In dichloromethane; water at -10 - -5℃;	66%

2-thioxo-3H-1,3-benzothiazole (149-30-4) → benzothiazole-2-sulfonyl chloride (2824-46-6)

Conditions	Yield
With chlorine; acetic acid

sodium 2-mercaptobenzothiazole (2492-26-4) → benzothiazole-2-sulfonyl chloride (2824-46-6)

Conditions	Yield
With hydrogenchloride; sodium hypochlorite solution In dichloromethane; water at -10 - -5℃; for 0.333333h;
With hydrogenchloride; sodium hypochlorite In dichloromethane; water at -10 - -5℃; for 0.333333h;

benzothiazole-2-sulfonyl chloride (2824-46-6) + (R)-2-amino-3-(3-chloro-4-hydroxyphenyl)propionic acid methyl ester hydrochloride → C24H18ClN3O7S4 (1014985-70-6)

Conditions	Yield
With pyridine; triethylamine In dichloromethane at 20℃; for 16h;	100%

benzothiazole-2-sulfonyl chloride (2824-46-6) + (R)-phenylglycine (875-74-1) → (R)-(Benzothiazole-2-sulfonylamino)-phenyl-acetic acid (184222-92-2)

Conditions	Yield
With sodium hydroxide at 10℃; for 10h;	97%

C29H38F3N5O4 (947768-33-4) + benzothiazole-2-sulfonyl chloride (2824-46-6) → C36H41F3N6O6S2 (947768-89-0)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	95%

benzothiazole-2-sulfonyl chloride (2824-46-6) + ethyl N-(2-aminoethyl)glycinate dihydrochloride → N-[2-(benzothiazole-2-sulfonylamino)ethyl]glycine ethyl ester (620628-51-5)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h;	92%
With triethylamine In dichloromethane at 20℃; for 2.08333h;	92%
With triethylamine In dichloromethane at 20℃; for 2.08333h;	92%

benzothiazole-2-sulfonyl chloride (2824-46-6) + L-valine hydrochloride (17498-50-9, 25616-14-2, 31320-20-4) → (S)-2-(Benzothiazole-2-sulfonylamino)-3-methyl-butyric acid (184222-96-6)

Conditions	Yield
With sodium hydroxide at 10℃; for 10h; pH=10 - 10.5; Substitution;	91%

benzothiazole-2-sulfonyl chloride (2824-46-6) + benzylamine (100-46-9) → N-benzylbenzo[d]thiazole-2-sulfonamide (2655-38-1)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;	90%

benzothiazole-2-sulfonyl chloride (2824-46-6) + L-Tryptophyl-L-methionyl-L-aspartyl-L-phenylalanine amide hydrochloride (5609-49-4) → (S)-3-{(S)-2-[(S)-2-(Benzothiazole-2-sulfonylamino)-3-(1H-indol-3-yl)-propionylamino]-4-methylsulfanyl-butyrylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid

Conditions	Yield
With sodium hydroxide	90%

benzothiazole-2-sulfonyl chloride (2824-46-6) + L-alanine hydrochloride (6003-05-0, 16428-74-3, 25616-13-1, 26570-06-9) → (S)-2-(Benzothiazole-2-sulfonylamino)-propionic acid (184222-98-8)

Conditions	Yield
With sodium hydroxide at 10℃; for 10h; pH=10 - 10.5; Substitution;	89%

indole (120-72-9) + benzothiazole-2-sulfonyl chloride (2824-46-6) → 2-(Indole-1-sulfonyl)-benzothiazole

Conditions	Yield
With sodium hydride In tetrahydrofuran	88%

benzothiazole-2-sulfonyl chloride (2824-46-6) + 4-piperidone hydrochloride (41979-39-9) → N-(benzothiazole-2-sulfonyl)-4-piperidone (1012884-70-6)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water for 10h; pH=10 - 11;	88%

benzothiazole-2-sulfonyl chloride (2824-46-6) + L-leucine hydrochloride (760-84-9) → (S)-2-(Benzothiazole-2-sulfonylamino)-4-methyl-pentanoic acid (270261-48-8)

Conditions	Yield
With sodium hydroxide at 10℃; for 10h; pH=10 - 10.5; Substitution;	87%

benzothiazole-2-sulfonyl chloride (2824-46-6) + (1R,2R)-1,2-diaminocyclohexane (20439-47-8) → C20H20N4O4S4

Conditions	Yield
With potassium carbonate In diethyl ether at 0℃;	85%

(S)-valinol (2026-48-4) + benzothiazole-2-sulfonyl chloride (2824-46-6) → N-(benzothiazol-2-sulfonyl)-(S)-valinol (377779-82-3)

Conditions	Yield
With sodium carbonate In dichloromethane; water at 0 - 20℃; for 12h;	82%
With triethylamine In dichloromethane at 20℃; for 1h;	3.1 g
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;
With triethylamine In dichloromethane at 20℃; for 1h;	3.1 g

L-tert-Leucine (20859-02-3) + benzothiazole-2-sulfonyl chloride (2824-46-6) → N-(benzothiazol-2-sulfonyl)-(S)-tert-leucine

Conditions	Yield
With sodium hydroxide at 10℃; for 10h;	81%

benzothiazole-2-sulfonyl chloride (2824-46-6) + C16H16FNO2 (1014985-09-1) → Bts-(D)Phe(3F)-OBn (1014985-10-4)

Conditions	Yield
With pyridine; triethylamine In dichloromethane at 20℃; Product distribution / selectivity;	74.4%

benzothiazole-2-sulfonyl chloride (2824-46-6) + 2-Methylaziridine (75-55-8, 41927-28-0, 76612-76-5, 76612-77-6, 205537-16-2) → 2-(2-methylaziridin-1-ylsulfonyl)benzo[d]thiazole (1258934-27-8)

Conditions	Yield
With potassium carbonate In ethyl acetate at 0 - 4℃;	71%

benzothiazole-2-sulfonyl chloride (2824-46-6) + glycine (56-40-6) → (benzothiazole-2-sulfonyl)glycine (268216-83-7)

Conditions	Yield
With sodium hydroxide; sodium carbonate In diethyl ether; water at 20℃; for 4h; Addition;	58%

benzothiazole-2-sulfonyl chloride (2824-46-6) + N-(p-ethoxyphenyl)urea (150-69-6) → C16H15N3O4S2

Conditions	Yield
With potassium carbonate In ethanol for 3h; Heating;	50%

(S)-2-(t-butyldimethylsilyloxymethyl)aziridine + benzothiazole-2-sulfonyl chloride (2824-46-6) → (S)-2-(2-((tert-butyldimethylsilyloxy)methyl)-aziridin-1-ylsulfonyl)benzo[d]thiazole

Conditions	Yield
With potassium carbonate In water; ethyl acetate at 0 - 20℃;	50%

benzothiazole-2-sulfonyl chloride (2824-46-6) + 3-O-methylfluorescein (70672-05-8) → fluorescein

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 16h;	49%

benzothiazole-2-sulfonyl chloride (2824-46-6) + aniline (62-53-3) → benzothiazole-2-sulfonic acid phenylamide (2743-86-4)

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane; water at 90℃; for 3h;	47%
With sodium hydrogencarbonate In 1,4-dioxane at 90℃; for 3h;	47%

benzothiazole-2-sulfonyl chloride (2824-46-6) + fluorescein (2321-07-5) → fluorescein

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 16h;	38%

(4-chloro-benzothiazol-2-yl)-urea (362521-53-7) + benzothiazole-2-sulfonyl chloride (2824-46-6) → C15H9ClN4O3S3

Conditions	Yield
With potassium carbonate In ethanol for 3h; Heating;	37%

7-hydroxy-2H-chromen-2-one (93-35-6) + benzothiazole-2-sulfonyl chloride (2824-46-6) → C16H9NO5S2

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 16h;	30%

benzothiazole-2-sulfonyl chloride (2824-46-6) + thiazol-2-yl-urea (35107-91-6) → C11H8N4O3S3

Conditions	Yield
With potassium carbonate In ethanol for 3h; Heating;	13%

benzothiazole-2-sulfonyl chloride (2824-46-6) → benzothiazole-2-sulfonamide (433-17-0)

Conditions	Yield
With ammonia

n-Dodecylamine (124-22-1) + benzothiazole-2-sulfonyl chloride (2824-46-6) → benzothiazole-2-sulfonic acid dodecylamide (15777-11-4)

Conditions	Yield
In ethanol

1-aminodecane (2016-57-1) + benzothiazole-2-sulfonyl chloride (2824-46-6) → benzothiazole-2-sulfonic acid decylamide (15777-10-3)

Conditions	Yield
In ethanol

Upstream product

• 149-30-4 2-Mercaptobenzothiazole 
• 2492-26-4 sodium 2-mercaptobenzothiazole 
• 149-30-4 2-thioxo-3H-1,3-benzothiazole 

Downstream Products

• 433-17-0 benzothiazole-2-sulfonamide 
• 184222-94-4 L-(benzothiazole-2-sulfonyl)phenylalanine 
• 184222-92-2 (R)-(Benzothiazole-2-sulfonylamino)-phenyl-acetic acid 
• 1047665-82-6 C₁₉H₁₈N₂O₄S₂ 
• 2743-86-4 benzothiazole-2-sulfonic acid phenylamide 
• 1014985-10-4 Bts-(D)Phe(3F)-OBn 
• 947768-89-0 C₃₆H₄₁F₃N₆O₆S₂ 
• 4276-60-2 2-(phenylthio)benzothiazole 
• 620628-51-5 N-[2-(benzothiazole-2-sulfonylamino)ethyl]glycine ethyl ester 

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