94125-42-5

Basic information

• Product Name: Benzenesulfonamide, 2-(3,3,3-trifluoropropyl)-
• Synonyms: 2-(3,3,3-Trifluoropropyl)benzenesulfonamide
• CAS NO: 94125-42-5
• Molecular Formula: C9H10 F3 N O2 S
• Molecular Weight: 253.245
• Mol File: 94125-42-5.mol

Chemical Properties

• CAS DataBase Reference: Benzenesulfonamide, 2-(3,3,3-trifluoropropyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, 2-(3,3,3-trifluoropropyl)-(94125-42-5)
• EPA Substance Registry System: Benzenesulfonamide, 2-(3,3,3-trifluoropropyl)-(94125-42-5)

Safety Data

• Hazardous Substances Data: 94125-42-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Benzenesulfonamide, 2-(3,3,3-trifluoropropyl)is utilized as an intermediate in the synthesis of various pharmaceuticals for its ability to interact with biological receptors and enzymes, which is crucial in the development of new drugs.
Used in Agrochemical Industry:
Benzenesulfonamide, 2-(3,3,3-trifluoropropyl)also serves as an intermediate in the production of agrochemicals, contributing to the development of substances that can enhance crop protection and management.
Used in Organic Compounds Synthesis:
Benzenesulfonamide, 2-(3,3,3-trifluoropropyl)is used in the synthesis of a range of other organic compounds, expanding its applications beyond the pharmaceutical and agrochemical sectors.
Used in Materials and Polymers Synthesis:
It may also find use in the synthesis of materials and polymers, indicating its versatility in chemical applications and potential for innovation in material science.
It is important to handle Benzenesulfonamide, 2-(3,3,3-trifluoropropyl)with care due to its potential hazards to human health and the environment if not properly managed.

Synthetic route

2-(3,3,3-trifluoro-1-propenyl)benzenesulfonamide → 2-(3,3,3-Trifluoropropyl)benzenesulfonamide (94125-42-5)

Conditions	Yield
With methanol; magnesium at 30 - 40℃; for 2h; Temperature;	95.5%

prosulfuron (94125-34-5) → 2-(3,3,3-Trifluoropropyl)benzenesulfonamide (94125-42-5) + 1-(4'-methoxy-6'-methyltriazin-2'-yl)-3{[2''-(3''',3''',3'''-trifluoropropyl)-3''-hydroxyphenyl]sulfonyl}urea + 1-(4'-methoxy-6'-methyltriazin-2'-yl)-3-{[2''-(1'''-hydroxy-3''',3''',3'''-trifluoropropyl)phenyl]sulfonyl}urea + 1-(4'-methoxy-6'-methyltriazin-2'-yl)-3-{[2''-(3''',3''',3'''-trifluoropropyl)-3'',4''-dihydroxyphenyl]sulfonyl}urea + 1-(4-hydroxy-6-methyl-1,3,5-triazin-2-yl)-3-[2-(3,3,3-trifluoropropyl)phenylsulfonyl]urea + 1-[4-(hydroxymethyl)-6-methoxy-1,3,5-triazin-2-yl]-3-[2-(3,3,3-trifluoropropyl)phenylsulfonyl]urea + further byproducts

Conditions	Yield
With Streptomyces griseolus (ATCC 11796) In N,N-dimethyl-formamide for 72h; Product distribution; other microorganisms; metabolism;	A n/a B 14% C 13% D 12% E n/a F 19% G n/a

prosulfuron (94125-34-5) → 2-(3,3,3-Trifluoropropyl)benzenesulfonamide (94125-42-5)

Conditions	Yield
With sodium acetate; acetic acid at 70℃; for 27h; pH=3.8;	60 mg

2-(3,3,3-trifluoro-1-propen-1-yl)-phenylsulfonamide → 2-(3,3,3-Trifluoropropyl)benzenesulfonamide (94125-42-5)

Conditions	Yield
palladium-carbon In ethyl acetate

isocyanate de chlorosulfonyle (1189-71-5) + 2-(3,3,3-Trifluoropropyl)benzenesulfonamide (94125-42-5) → N-(aminocarbonyl)-2-(3,3,3-trifluoropropyl)benzenesulfonamide (173171-98-7)

Conditions	Yield
With water 1.) CH3CN, 45 min, 2.) CH3CN, 40 deg C, 15 min; Yield given. Multistep reaction;

2-(3,3,3-Trifluoropropyl)benzenesulfonamide (94125-42-5) → N-<<(aminocarbonyl)amino>carbonyl>-2-(3,3,3-trifluoropropyl)benzenesulfonamide

Conditions	Yield
Multi-step reaction with 2 steps 1: 2.) H2O / 1.) CH3CN, 45 min, 2.) CH3CN, 40 deg C, 15 min 2: 2.) H2O / 1.) CH3CN, 1.5 h, 2.) CH3CN, 40 deg C, 15 min View Scheme

2-(3,3,3-Trifluoropropyl)benzenesulfonamide (94125-42-5) → N-<<<<(aminocarbonyl)amino>carbonyl>amino>carbonyl>-2-(3,3,3-trifluoropropyl)benzenesulfonamide

Conditions	Yield
Multi-step reaction with 3 steps 1: 2.) H2O / 1.) CH3CN, 45 min, 2.) CH3CN, 40 deg C, 15 min 2: 2.) H2O / 1.) CH3CN, 1.5 h, 2.) CH3CN, 40 deg C, 15 min 3: 2.) H2O / 1.) CH3CN, 1.5 h, 2.) CH3CN, 40 deg C, 15 min View Scheme

Upstream product

• 2856-63-5 2-Chlorophenylacetonitrile 
• 94125-34-5 prosulfuron 

Downstream Products

• 173171-98-7 N-(aminocarbonyl)-2-(3,3,3-trifluoropropyl)benzenesulfonamide 

Relevant articles and documents

Soil transformation of prosulfuron

The transformation of prosulfuron [1-(4-methoxy-6-methyltriazine-2-yl)-3- [2-(3,3,3-trifluropropyl)-phenylsulfonyl]urea] in three soils at different pH values (sterilized and unsterilized) was studied, and it was shown that the rate of transformation was high in acidic soil. From the results obtained in sterile soils, it is shown that the mechanism of dissipation was mainly chemical in acidic soils. A new metabolite, 2-(3,3,3-trifluoropropyl)phenylsulfonic acid, was identified.

Microbial Transformations of Prosulfuron

Microbial transformations were conducted with prosulfuron {1-(4′-methoxy-6′-methyltriazin-2′-yl)-3-[[2″- (3?,3?,3?-trinuoropropyl)phenyl]sulfonyl]urea} to identify pathways by which the sulfonylurea herbicide is metabolized by microorganisms. Streptomyces griseolus produced four new hydroxylated metabolites which were isolated, chromatographically purified, and characterized by mass spectrometry and NMR spectroscopy as the following: a benzyl alcohol from methyl hydroxylation on the triazine ring, phenolic and catechol metabolites by 3″ and subsequent 4″ hydroxylation on the carbocyclic aromatic ring, and a second benzylic alcohol obtained by microbial hydroxylation of the trifluoropropyl side chain. The new metabolites were used as analytical standards for soil incubation studies.

Synthesis method of prosulfuron intermediate

The invention discloses a synthesis method of a prosulfuron intermediate 2-(3, 3, 3-trifluoropropyl) benzenesulfonamide, which comprises the following steps: by taking o-chlorobenzyl cyanide and ethyl trifluoroacetate as initial raw materials, firstly carrying out acylation reaction in the presence of organic alkali, then carrying out decyanation reaction in the presence of sulfuric acid, and then carrying out reduction reaction in the presence of a reducing agent, carrying out a dehydration reaction in the presence of a catalyst, carrying out a reduction reaction in the presence of a reducing agent, carrying out a sulfhydrylation reaction with a sulfhydrylation reagent, carrying out a sulfonyl chlorination reaction with chlorine in the presence of water, and carrying out a sulfonylation reaction with ammonia water. Compared with the prior art, the synthesis method has the advantages that the adopted raw materials and auxiliaries are low in cost and easy to obtain, the reaction conditions are mild, the operation is simple and convenient, the safety is higher, the synthesis method is more environment-friendly, the synthesis route is particularly important in the current times with stricter requirements on safety and environmental protection, and the safety of industrial production can be ensured.

2 - (3, 3, 3 - [...]) benzenesulfonamide preparation method (by machine translation)

The invention discloses a 2 - (3, 3, 3 - [...]) benzenesulfonamide of the preparation method, it is composed of 2 - (3, 3, 3 - trifluoro - 1 - propenyl) benzenesulfonamide through reduction reaction; magnesium ribbon and the reduction reaction is carried out in the presence of methanol. 2 - (3, 3, 3 - Trifluoro - 1 - propenyl) benzenesulfonamide with magnesium ribbon in a molar ratio of 1:1 - 1:3; 2 - (3, 3, 3 - trifluoro - 1 - propenyl) benzenesulfonamide with methanol weight ratio of 1:3 - 1:10; reducing the reaction temperature is 10 - 60 °C; reducing the reaction time is 1 - 5 the H. This invention adopts the magnesium strip + methanol reduction system reduction 2 - (3, 3, 3 - trifluoro - 1 - propenyl) benzenesulfonamide, compared with the noble metal catalytic hydrogenation and the operation is simple, the production cost is lower. The invention through optimization of the reaction conditions, can obtain higher reaction yield and purity of the product, is suitable for industrial production. (by machine translation)

N-phenylsulfonyl-N'-triazinylureas

N-Phenylsulfonyl-N'-pyrimidinyl- and -triazinylureas of the formula I STR1 wherein A is 3,3,3-trifluoropropyl or 3,3-difluorobutyl, R1 is hydrogen, halogen, nitro, cyano, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio, C1 -C4 -alkylsulfinyl, C1 -C4 -alkylsulfonyl, --CO--R6, --NR7 R8, --CO--NR9 R10 or --SO2 --NR11 R12, R2 is hydrogen, halogen, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio, C1 -C4 -alkylsulfinyl or C1 -C4 -alkylsulfonyl, R3 and R4 independently of one another are each hydrogen, halogen, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C2 -C4 -haloalkoxy, C1 -C4 -alkylthio, C1 -C4 -haloalkylthio, C2 -C4 -alkoxyalkyl, C1 -C4 -alkoxy or --NR12 R13, R5 is hydrogen, C1 -C4 -alkyl or C1 -C4 -alkoxy, R6 is C1 -C4 -alkoxy, C1 -C4 -haloalkoxy, C1 -C4 -alkylthio, C2 -C6 -alkoxyalkoxy, hydrogen, C1 -C4 -alkyl or C1 -C4 -haloalkyl, R7, R8, R9, R10, R11, R12 and R13 independently of one another are each hydrogen or C1 -C4 -alkyl, E is nitrogen, and Z is oxygen or sulfur; and also the salts of these compounds.