5-Chlorothiophene-2-sulfonyl chloride
- Product Name
- 5-Chlorothiophene-2-sulfonyl chloride
- CAS No.
- 2766-74-7
- Chemical Name
- 5-Chlorothiophene-2-sulfonyl chloride
- Synonyms
- AKOS B019398;BUTTPARK 27\04-09;TIMTEC-BB SBB003378;ART-CHEM-BB B019398;5-chlorothiophene-2-sulfonyl;5-chlorobenzenesulfonyl chloride;5-CHLOROTHIOPHENESULPHONYL CHLORIDE;5-CHLORO-2-THIENYLSULFONYL CHLORIDE;5-Chlorothiophen-2-sulfonyl chloride;5-CHLOROTHIOPHENE-2-SULFONYL CHLORIDE
- CBNumber
- CB4283960
- Molecular Formula
- C4H2Cl2O2S2
- Formula Weight
- 217.09
- MOL File
- 2766-74-7.mol
5-Chlorothiophene-2-sulfonyl chloride Property
- Melting point:
- 25-28°C
- Boiling point:
- 112-117 °C (lit.)
- Density
- 1.623 g/mL at 25 °C (lit.)
- refractive index
- n20/D 1.586(lit.)
- Flash point:
- >230 °F
- storage temp.
- 2-8°C
- form
- solid
- Specific Gravity
- 1.623
- color
- Colorless to Yellow to Orange
- Water Solubility
- Not miscible in water.
- Sensitive
- Moisture Sensitive
- BRN
- 130710
- InChI
- InChI=1S/C4H2Cl2O2S2/c5-3-1-2-4(9-3)10(6,7)8/h1-2H
- InChIKey
- SORSTNOXGOXWAO-UHFFFAOYSA-N
- SMILES
- C1(S(Cl)(=O)=O)SC(Cl)=CC=1
- CAS DataBase Reference
- 2766-74-7(CAS DataBase Reference)
Safety
- Hazard Codes
- C
- Risk Statements
- 34-29-14
- Safety Statements
- 26-27-36/37/39-45-28A-25
- RIDADR
- UN 3265 8/PG 2
- WGK Germany
- 3
- Hazard Note
- Corrosive
- HazardClass
- 8
- PackingGroup
- II
- HS Code
- 29349990
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H314Causes severe skin burns and eye damage
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P363Wash contaminated clothing before reuse.
P405Store locked up.
N-Bromosuccinimide Price
- Product number
- 544272
- Product name
- 5-Chlorothiophene-2-sulfonyl chloride
- Purity
- 96%
- Packaging
- 5g
- Price
- $29.33
- Updated
- 2025/07/31
- Product number
- 544272
- Product name
- 5-Chlorothiophene-2-sulfonyl chloride
- Purity
- 96%
- Packaging
- 1g
- Price
- $25
- Updated
- 2023/06/20
- Product number
- C2343
- Product name
- 5-Chloro-2-thiophenesulfonyl Chloride
- Purity
- >98.0%(GC)(T)
- Packaging
- 5g
- Price
- $59
- Updated
- 2025/07/31
- Product number
- C2343
- Product name
- 5-Chloro-2-thiophenesulfonyl Chloride
- Purity
- >98.0%(GC)(T)
- Packaging
- 25g
- Price
- $236
- Updated
- 2025/07/31
- Product number
- C420520
- Product name
- 5-Chloro-2-thiophenesulfonyl Chloride
- Packaging
- 1g
- Price
- $130
- Updated
- 2021/12/16
5-Chlorothiophene-2-sulfonyl chloride Chemical Properties,Usage,Production
Chemical Properties
5-Chlorothiophene-2-sulfonyl chloride is white to yellow crystalline low melting solid
Uses
5-Chloro-2-thiophenesulfonyl Chloride is a sulfonylthiophene derivative used in the preparation of Notch-1-sparing γ-secretase inhibitors for the treatment of Alzheimer's disease.
Uses
5-Chlorothiophene-2-sulfonyl chloride is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuffs. It is used in the preparation of Notch-1-sparing γ-secretase inhibitors for the treatment of Alzheimer's disease.
Synthesis Reference(s)
Tetrahedron, 21, p. 1333, 1965 DOI: 10.1016/S0040-4020(01)98293-6
General Description
5-Chlorothiophene-2-sulfonyl chloride can be prepared from 2-chlorothiophene by reacting with chlorosulfonic acid in the presence of phosphorus pentachloride.
Synthesis
96-43-5
2766-74-7
The following procedure is adapted from C. A. Hunt et al. J. Med. Chem. 1994, 37, 240-247. chlorosulfonic acid (240 mL, 3.594 mol) was added to a three-necked round-bottomed flask equipped with a mechanical stirrer, air condenser, dropping funnel, and moisture-proof tubing. Phosphorus pentachloride (PCl5, 300 g, 1.44 mol, 0.40 eq.) was added in batches with stirring, taking 45 minutes. During the addition process, a large amount of hydrogen chloride gas was violently released, but the temperature of the mixture did not rise significantly (<40 °C). When all the PCl5 was added, an almost clear light yellow solution was formed with only a few solid fragments suspended in it. Stirring was continued until gas escape ceased (~0.5 h). Subsequently, the reaction vessel was cooled in an ice bath and 2-chlorothiophene (66.0 mL, 0.715 mol) was slowly added through a dropping funnel over a period of 1.0 hour. After the addition of the first few drops of 2-chlorothiophene, the mixture changed to a dark purple color, and when all the thiophene was added, a dark purple solution was formed. Hydrogen chloride gas was continuously released at a slow rate during the addition. The reaction mixture was stirred at room temperature overnight. Subsequently, the dark purple clear solution was added dropwise to crushed ice (3 L) over a period of 0.5 hours. The purple color disappeared instantly, except for the ice, and a colorless dilute emulsion was formed, which was mechanically stirred at room temperature for about 1 hour. Next, the mixture was extracted with dichloromethane (CH2Cl2, 3 x 300 mL). The combined dichloromethane extracts were washed sequentially with water (1 × 200 mL), saturated sodium bicarbonate solution (NaHCO3, 1 × 250 mL), and brine (1 × 100 mL), dried over anhydrous sodium sulfate (Na2SO4), and concentrated on a rotary evaporator to give the crude product as a pale white to pale yellow viscous mass, which gradually solidified into a semi-solid. Finally, it was purified by high vacuum distillation (boiling point 110-112 °C, pressure 712 mmHg) to obtain 135.20 g (88% yield) of 5-chlorothiophene-2-sulfonyl chloride as a colorless to light yellow semi-solid.
References
[1] Patent: WO2007/56167, 2007, A2. Location in patent: Page/Page column 33-34
[2] Patent: WO2008/137809, 2008, A2. Location in patent: Page/Page column 61-62
[3] Pharmazie, 1994, vol. 49, # 2-3, p. 115 - 117
[4] Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 3, p. 1063 - 1064
[5] Justus Liebigs Annalen der Chemie, 1937, vol. 532, p. 250,279
5-Chlorothiophene-2-sulfonyl chloride Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 5-Chlorothiophene-2-sulfonyl chloride manufacturers
- Product
- 5-Chlorothiophene-2-sulfonyl chloride 2766-74-7
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 97%
- Supply Ability
- As your request
- Release date
- 2025-03-19
- Product
- 5-Chlorothiophene-2-sulfonyl chloride 2766-74-7
- Price
- US $2.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- Customise
- Release date
- 2018-08-09