4151-50-2

Basic information

• Product Name: Sulfluramid
• Synonyms: SULFLURAMID;N-ETHYL HEPTADECAFLUOROOCTYLSULFONAMIDE;n-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-octanesulfonamide;N-ETHYL PERFLUOROOCTANESULFONAMIDE;N-ETHYL PERFLUOROOCTANESULPHONAMIDE;N-ETHYL PERFLUOROOCTYLSULFONAMIDE;N-ETHYL PERFLUOROOCTYLSULPHONAMIDE;Ethylperfluorooctanesulfonamide
• CAS NO: 4151-50-2
• Molecular Formula: C₁₀H₆F₁₇NO₂S
• Molecular Weight: 527.19
• EINECS: 223-980-3
• Product Categories: Organics;Pesticide & intermediate;Metal Isotopes;Sulfur & Selenium Compounds;Agro-Products;Aliphatics
• Mol File: 4151-50-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 75-85°C
• Boiling Point: 120°C 0,5mm
• Flash Point: 102.9 °C
• Appearance: Tan powder
• Density: 1.1561
• Vapor Pressure: 0.0269mmHg at 25°C
• Refractive Index: 1.5327
• Storage Temp.: -20°C Freezer
• PKA: 9.5 (very weak acid)
• Water Solubility: Insoluble (25 °C)
• CAS DataBase Reference: Sulfluramid(CAS DataBase Reference)
• NIST Chemistry Reference: Sulfluramid(4151-50-2)
• EPA Substance Registry System: Sulfluramid(4151-50-2)

Safety Data

• Hazard Codes: Xi,N,Xn
• Statements: 21-22-51/53
• Safety Statements: 36/37-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• RTECS: RG9701300
• Hazardous Substances Data: 4151-50-2(Hazardous Substances Data)

Usage

Chemical Properties

Tan Powder

Uses

Different sources of media describe the Uses of 4151-50-2 differently. You can refer to the following data:
1. Sulfluramid is an insecticide.
2. Sulfluramid is used for the control of ants and roaches in households and of the red imported fire ant in wider situations.

Definition

ChEBI: A sulfonamide obtained by the formal condensation of perfluorooctane-1-sulfonic acid with ethylamine.

Agricultural Uses

Insecticide, Acaricide, Termiticide: Used as ant, roach and termite trap bait. Not listed for use in EU countries. Actively registered for use in the U.S. According to the Fluoride Action Network, this chemical is not registered for use on food or crops and is scheduled to phased out by 2016.

Trade name

FINITRON?; FIRSTLINE?; FLUORGUARD?; GX-071?; MICRO-GEN ANT REACTOR?; VOLCANO?

Metabolic pathway

Sulfluramid is a highly fluorinated sulfonamide which was introduced relatively recently for the control of ants and roaches. It is also used now for the control of the red imported fire ant (Solenupsis invicta). Its fate in rats has been studied but, due to its limited use pattern, there appears to be no information yet published on its environmental fate nor on its metabolism in plants. It is biotransformed by N-de-ethylation to an insecticidally active and toxic metabolite.

Degradation

Sulfluramid is stable for more than 90 days at 50 °C and it is similarly stable in light under glass. Though a weak acid, it is highly lipophilic due to the perfluorooctyl group.

InChI:InChI=1/C10H6F17NO2S/c1-2-28-31(29,30)10(26,27)8(21,22)6(17,18)4(13,14)3(11,12)5(15,16)7(19,20)9(23,24)25/h28H,2H2,1H3

Synthetic route

perfluorooctyl sulfofluorure (307-35-7) + ethylamine (75-04-7) → N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2)

Conditions	Yield
Stage #1: perfluorooctyl sulfofluorure; ethylamine With triethylamine In diethyl ether at 0 - 20℃; for 17h; Stage #2: With sodium hydrogencarbonate In diethyl ether for 3h; Heating; Further stages.;	56%
In diethyl ether anhydr. ether, at -5 to 0°C, 2.75 h;
With triethylamine In di-isopropyl ether for 4h; Reflux;
In diethyl ether anhydr. ether, at -5 to 0°C, 2.75 h;

perfluorooctanesulphonyl chloride (423-60-9) + tri-n-butylamine hydrofluoride (25152-55-0, 60435-94-1, 73602-62-7, 127322-37-6, 130089-03-1) + ethylamine (75-04-7) → N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) + N,N-dibutyl perfluorooctanesulfonamide

Conditions	Yield
In various solvent(s)	A 0.05 mol B 0.005 mol

perfluorooctanesulphonyl chloride (423-60-9) + ethylamine (75-04-7) → N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) + C8HF17O2S + C8HF17O2S*C2H7N

Conditions	Yield
In dichloromethane Product distribution; var. solv, investigated;

perfluorooctyl sulfofluorure (307-35-7) + ethylamine (75-04-7) → hydrogen fluoride ethylamine (65756-36-7) + N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2)

Conditions	Yield
In diethyl ether at -30-0°C,2.75 h;
In diethyl ether at -30-0°C,2.75 h;

N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) + 2-bromoethanol (540-51-2) → N-ethyl-N-(2-hydroxyethyl)-perfluorooctane-1-sulfonamide (1691-99-2)

Conditions	Yield
With potassium carbonate; sodium iodide In acetone for 48h; Heating;	99%

N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) + 2-(tert-butyldimethylsilyloxy)ethanol (102229-10-7) → 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonic acid [2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-ethyl-amide (1017593-64-4)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In diethyl ether at 0 - 25℃; Mitsunobu reaction; sonication;	98%

bromoethyl acetate (927-68-4) + N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) → 2-(N-ethyl-perfluorooctylsulfonamido)ethyl acetate (1017593-63-3)

Conditions	Yield
With potassium carbonate; sodium iodide In acetone for 36h; Heating;	92%

N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) + bromoacetic acid methyl ester (96-32-2) → methyl 2-(N-ethyl-perfluorooctanesulfonamido) acetate (87988-69-0)

Conditions	Yield
With potassium carbonate; sodium iodide In acetone for 3h; Heating;	90%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) → N-(4,6-dichloro-1,3,5-triazin-2-yl)-N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide

Conditions	Yield
Stage #1: N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide With sodium In ethanol for 0.5h; Metallation; Stage #2: 1,3,5-trichloro-2,4,6-triazine In acetone at -78 - 20℃; for 2h; Substitution;	72%

glycolic acid methyl ester (96-35-5) + N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) → methyl 2-(N-ethyl-perfluorooctanesulfonamido) acetate (87988-69-0)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In diethyl ether at 0 - 25℃; Mitsunobu reaction; sonication;	67%

trifluoro-[1,3,5]triazine (675-14-9) + N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) → N-(4,6-difluoro-1,3,5-triazin-2-yl)-N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide

Conditions	Yield
Stage #1: N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide With sodium In methanol for 1h; Metallation; Stage #2: trifluoro-[1,3,5]triazine In acetone at -78℃; for 3h; Substitution;	31%

vinyl chloroacetate (2549-51-1) + N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) → N-ethyl-N-(heptadecafluoro-octane-1-sulfonyl)-glycine vinyl ester (678-36-4)

N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) → N-ethyl-N-(2-hydroxyethyl)-perfluorooctane-1-sulfonamide (1691-99-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / potassium carbonate; NaI / acetone / 36 h / Heating 2: 93 percent / aq. potassium hydroxide / 3 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 98 percent / diisopropyl azodicarboxylate; triphenylphosphine / diethyl ether / 0 - 25 °C / sonication 2: 96 percent / aq. HCl / methanol / 48 h / 25 °C View Scheme
With potassium hydroxide und Erwaermen des Reaktionsprodukts mit 2-Chlor-aethanol;

[1,3]-dioxolan-2-one (96-49-1) + N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) → N-ethyl-N-(2-hydroxyethyl)-perfluorooctane-1-sulfonamide (1691-99-2)

Conditions	Yield
With pyridine at 176℃;

N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) → 2-(N-ethyl-perfluorooctane sulfonamido) acetic acid (2991-50-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / potassium carbonate; sodium iodide / acetone / 3 h / Heating 2: 40 percent / aq. NaOH / dioxane / 2 h / 65 °C View Scheme
Multi-step reaction with 2 steps 1: 67 percent / diisopropyl azodicarboxylate; triphenylphosphine / diethyl ether / 0 - 25 °C / sonication 2: 40 percent / aq. NaOH / dioxane / 2 h / 65 °C View Scheme

N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) → adipic acid bis-{2-[ethyl-(heptadecafluoro-octane-1-sulfonyl)-amino]-ethyl ester} (599-58-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide / und Erwaermen des Reaktionsprodukts mit 2-Chlor-aethanol View Scheme

N-ethyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide (4151-50-2) + allyl bromide (106-95-6) → C13H10F17NO2S (24924-36-5)

Conditions	Yield
With potassium hydroxide In water; dimethyl sulfoxide at 20℃; for 14.5 - 16.5h;

Upstream product

• 307-35-7 perfluorooctyl sulfofluorure 
• 75-04-7 ethylamine 
• 423-60-9 perfluorooctanesulphonyl chloride 
• 25152-55-0 tri-n-butylamine hydrofluoride 

Downstream Products

• 1691-99-2 N-ethyl-N-(2-hydroxyethyl)-perfluorooctane-1-sulfonamide 
• 24924-36-5 C₁₃H₁₀F₁₇NO₂S 
• 2991-50-6 2-(N-ethyl-perfluorooctane sulfonamido) acetic acid 

Relevant articles and documents

Synthesis and surface activities of organic solvent-soluble fluorinated surfactants

A variety of fluorinated surfactants soluble in organic solvent were prepared, including C8F17SO2NHCnH2n+1 (n = 2, 4, 6, 8, 10), C8F17SO2NHR (R = C6H11, C6H5), C8F17SO2N(CnH2n+1 )2 (n = 1, 2, 3, 4) and C8F17SO2NH(CH2)nN HO2SC8F17 (n = 6, 10). Their surface activities in various organic solvents were determined by surface tension measurement. The results showed that these fluorinated surfactants can reduce the surface tension of both polar and non-polar organic solvents. In general, organic solvents with strong polarity or long alkyl chain are beneficial to increase the surface activity of these polar fluorinated surfactants. By comparing fluorinated surfactants with the same fluorocarbon segment and connecting group, C8F17SO2N(CnH2n+1 )2 (n = 1, 2, 3, 4) showed lower surface activity in organic solvents than C8F17SO2NHCnH2n+1 (n = 2, 4, 6, 8) with an equal carbon number of the solvophilic group. Through surface tension vs. concentration curves given for N-octyl perfluorooctanesulfonamide in various organic solvents, a break point like the critical micelle concentration of ordinary surfactants in aqueous solutions was observed, and the effect of the different types of organic solvents on adsorption and aggregation behavior was also studied.

Method for exterminating termites

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