82097-01-6

Basic information

• Product Name: 2-(2-CHLOROETHOXY)-BENZENESULFONAMIDE
• Synonyms: 2-(2-CHLOROETHOXY)-BENZENESULFONAMIDE;2-(2-chloroethoxy)benzensulfonamide;2-(2-CHLOROETHOXY)BENZENESULFONAMIDE, 99%+;2-(2-CHLOROETHOXY)-BENZENESULFOMIDE
• CAS NO: 82097-01-6
• Molecular Formula: C₈H₁₀ClNO₃S
• Molecular Weight: 235.69
• Mol File: 82097-01-6.mol

Chemical Properties

• Melting Point: 119 °C
• Boiling Point: 421.1°C at 760 mmHg
• Flash Point: 208.5°C
• Appearance: /
• Density: 1.384g/cm³
• Vapor Pressure: 2.68E-07mmHg at 25°C
• Refractive Index: 1.559
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.97±0.60(Predicted)
• CAS DataBase Reference: 2-(2-CHLOROETHOXY)-BENZENESULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-CHLOROETHOXY)-BENZENESULFONAMIDE(82097-01-6)
• EPA Substance Registry System: 2-(2-CHLOROETHOXY)-BENZENESULFONAMIDE(82097-01-6)

Safety Data

• Hazardous Substances Data: 82097-01-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(2-Chloroethoxy)-benzenesulfonamide is used as a potential antibacterial agent for its sulfonamide center, which is known to inhibit bacterial growth. However, further research is needed to confirm its effectiveness and safety.
Used in Chemical Research:
2-(2-Chloroethoxy)-benzenesulfonamide is used as a subject of study in chemical research to explore its properties, potential applications, and possible toxicity. This can help in understanding its potential uses in various industries and guide safe handling procedures.

InChI:InChI=1/C8H10ClNO3S/c9-5-6-13-7-3-1-2-4-8(7)14(10,11)12/h1-4H,5-6H2,(H2,10,11,12)

Upstream product

• 3724-14-9 2-hydroxybenzenesulfonamide 
• 82097-50-5 triasulfuron 

Downstream Products

• 99722-82-4 2-(2-chloroethoxy)benzenesulfonyl isocyanate 

Relevant articles and documents

Discovery of ortho-Alkoxy Substituted Novel Sulfonylurea Compounds That Display Strong Herbicidal Activity against Monocotyledon Grasses

In the present study, we have designed and synthesized a series of 42 novel sulfonylurea compounds with ortho-alkoxy substitutions at the phenyl ring and evaluated their herbicidal activities. Some target compounds showed excellent herbicidal activity against monocotyledon weed species. When applied at 7.5 g ha-1, 6-11 exhibited more potent herbicidal activity against barnyard grass (Echinochloa crus-galli) and crab grass (Digitaria sanguinalis) than commercial acetohydroxyacid synthase (AHAS; EC 2.2.1.6) inhibitors triasulfuron, penoxsulam, and nicosulfuron at both pre-emergence and postemergence conditions. 6-11 was safe for peanut for postemergence application at this ultralow dosage, suggesting that it could be considered a potential herbicide candidate for peanut fields. Although 6-11 and triasulfuron share similar chemical structures and have close Ki values for plant AHAS, a significant difference has been observed between their LUMO maps from DFT calculations, which might be a possible factor that leads to their different behaviors toward monocotyledon weed species.

Kinetics and Hydrolysis Mechanism of Triasulfuron

The hydrolysis of the sulfonylurea herbicide triasulfuron [(2-(2-chloroethoxy)-N-[[4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl] benzenesulfonamide] was studied in aqueous buffers of pH values 2, 3, 4, 5, 6, 7, and 9. The reaction was of first-order and pH-dependent. Triasulfuron was more persistent in neutral or weakly basic than in acidic solution. Five metabolites have been isolated and identified. At all pH values studied, the primary pathway of degradation was the cleavage of the sulfonylurea bridge. However, minor degradation pathways have also been observed like O-demethylation and opening of the triazine ring. The product distribution was pH-dependent.

Process for the preparation of 2-(2-chloroethoxy)-benzenesulfonamide

In accordance with a novel process, 2-(2-chloroethoxy)-benzenesulfonamide of formula I STR1 is prepared by etherification of 4-chlorophenol of formula II STR2 with ethylene carbonate and chlorination of the resulting 4-(2-hydroxyethoxy)-chlorobenzene of formula III STR3 with phosgene or thionyl chloride to give 4-(2-chloroethoxy)-chlorobenzene of formula IV STR4 which is converted with chlorosulfonic acid ClSO3 H and sodium hydroxide to the sulfonic acid sodium salt of formula V STR5 which is hydrogenated to the compound of formula VI STR6 which is subsequently reacted with phosgene to the sulfonic acid chloride of formula VII STR7 which is reacted with amonia to the sulfonamide of formula I.

Process for the preparation of 2-(2-chloroethoxy)-benzenesulfonamide

In accordance with a novel process, 2-(2-chloroethoxy)-benzene-sulfonamide of formula I STR1 is prepared by etherification of 4-chlorophenol of formula II STR2 with ethylene carbonate and chlorination of the resulting 2-(2-hydroxyethoxy)-chlorobenzene of formula III STR3 with phosgene to give 2-(2-chloroethoxy)-chlorobenzene of formula IV STR4 which is converted with chlorosulfonic acid ClSO3 H and sodium hydroxide to the sulfonic acid sodium salt of formula V STR5 which is hydrogenated to the compound of formula VI STR6 which is subsequently reacted with phosgene to the sulfonic acid chloride of formula VII STR7 which is reacted with ammonia to the sulfonamide of formula I.

Process for producing sulfonylureas

There is described a novel process for producing sulfonylureas of formula I STR1 wherein R1 is hydrogen or alkyl, R2 is STR2 E is =N-- or =CH--, R3 is alkyl, alkoxy or halogen, R4 is alkyl, cycloalkyl, alkoxy, halogen, alkoxy-alkyl, halo-alkyl or halo-alkoxy, R5 is hydrogen or alkyl, T is a substituted phenyl group STR3 Y is hydrogen or halogen, X is hydrogen, halogen, alkyl, halo-alkyl, alkenyl, halo-alkenyl, alkynyl, alkoxy, halo-alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, halo-alkylthio, alkylsulfonyloxy, phenylsulfonyloxy, phenylsulfonyloxy mono- or polysubstituted by alkyl, or is di-alkylsulfamoyl, and A is a bridge member which has 3 or 4 atoms and which contains 1 or 2 hetero atoms, selected from the group consisting of oxygen, sulfur and nitrogen, the said process comprising reacting a silfonamide of the formula II in the presence of a base, with diphenyl carbonate to form a salt of a phenyl carbamate converting this salt into the free phenyl carbamate and reacting this further with an amine. Sulfonylureas are herbicidally effective compounds.

N-Phenylsulfonyl-N'-triazinylureas

N-Phenylsulfonyl-N'-triazinylureas of the general formula STR1 and the salts thereof with amines, alkali metal or alkaline earth metal bases or with quaternary ammonium bases, have good pre- and postemergence selective herbicidal and growth regulating properties. In the above formula Q is fluorine, fluoromethyl, chloromethyl, trichloromethyl, 1,2-dichloroethyl, 1,2-dibromoethyl, 1,2-dichloropropyl, 1,2-dibromopropyl, 1,2-dibromoisobutyl, 1,2-dichloro-1-methyl-ethyl or 1,2-dibromo-1-methyl-ethyl, X is oxygen, sulfur, a sulfinyl or sulfonyl bridge, Z is oxygen or sulfur, R2 is hydrogen, halogen, C1 -C5 alkyl, C2 -C5 alkenyl, C1 -C4 haloalkyl, or a radical --Y--R5, --COOR6, --NO2 or --CO--NR7 --R8, R3 and R4, each independently of the other, are hydrogen, C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 alkylthio, C1 -C4 haloalkyl, halogen or alkoxyalkyl of at most 4 carbon atoms, R5 and R6, each independently of the other, are C1 -C5 alkyl, C2 -C5 alkenyl or C2 -C6 alkynyl, R7 and R8, each independently of the other, are hydrogen, C1 -C5 alkyl, C2 -C5 alkenyl or C2 -C6 alkynyl, and Y is oxygen, sulfur, a sulfinyl or sulfonyl bridge.