133525-13-0

Basic information

• Product Name: 3-[(3,3,3-trifluoropropyl)sulfanyl]propanoic acid
• Synonyms: alpha-Fluoro-omega-{2-[(2-carboxyethyl)sulfanyl]ethyl}poly(difluoromethylene)
• CAS NO: 133525-13-0
• Molecular Formula: C₅H₉FO₂S?[C₂F₄]_n
• Molecular Weight: 152.1872
• Mol File: 133525-13-0.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: 3-[(3,3,3-trifluoropropyl)sulfanyl]propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[(3,3,3-trifluoropropyl)sulfanyl]propanoic acid(133525-13-0)
• EPA Substance Registry System: 3-[(3,3,3-trifluoropropyl)sulfanyl]propanoic acid(133525-13-0)

Safety Data

• Hazardous Substances Data: 133525-13-0(Hazardous Substances Data)

Upstream product

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• 69412-76-6 3,3,3-trifluoro-propane-1-thiol 
• 460-32-2 3-bromo-1,1,1-trifluoropropane 
• 292638-85-8 acrylic acid methyl ester 

Relevant articles and documents

Preparation, reactions and physical properties of segmented 2-(perfluoroalkyl)ethanesulfinic acids and their derivatives. the role of the perfluoroalkyl group in finding new and useful compounds and in searching out new chemistry

2-(Perfluoroalkyl)ethanesulfinic acids of the formula RFCH2CH2SO2H (2, where RF=n-C6F13, or n-C8F17) are synthesized from the thiol, RFCH2CH2SH (1). These segmented acids 2 have sharp melting point (mp) and can be recrystallized. The C6 or C8 perfluoroalkyl group confers unusual "fluophilic" properties to acids 2 and their derivatives. Water solutions of acids 2 and their Na, K, Cs and Bu4N salts are highly surface active and stable for several days, and are more effective in reducing surface tension at the air/water interface than sodium n-perfluorooctanesulfonate (10). Sodium salts 2 (C6, C8) are converted to K and Cs salts by methathesis in high yield. However, the amphiphilic Bu4N salts of 2 (C6, C8) are best prepared in a biphasic system (C6, 99.6% yield). Acids 2 are synthesized by three methods. (1) Oxidation of the C8 thiol 1 (at -35°C) by m-CPBA gives acid 2 (C8) in 73% yield and unwanted disulfide (3) in 27% yield. The bulky, strongly electronegative RF group of 1 may slow oxidation of the RSOH (intermediate) to allow disproportionation with RSH into disulfide 3 and water. (2) Hydrolysis of RFCH2CH2SO2SCH2CH 2RF (4) with strong base gives salt 2 (C6, or C8; 92% yield). (3) Heating sulfone, RFCH2CH2SO2CH2CH 2Y (8) with a base (M2CO3) eliminates RFCH2CH2SO2M (2, M=Na, K, Cs) in 95-100% yield (C6, C8). Alternatively, 8 with the sodium thiolate of 1 gives RFCnH2nSCH2CH2Y (7, 90%) and sodium salt 2 (C6, 95%). Conjugate addition of the RFCH2CH2SO2- to CH2CHY gives sulfones 8, and RFCH2CH2SO2- adds stereospecifically to cyclohexene oxide, giving the trans-adduct 13. RFCH2CH2SO2H (2), with azo initiator, telomerizes acrylamide to a water-soluble, surface active product.

PROCESSES FOR THE PREPARATION OF PESTICIDAL COMPOUNDS

The disclosure relates to efficient and economical synthetic chemical processes for the preparation of pesticidal thioethers. Further, the disclosure relates to certain novel compounds useful in the preparation of pesticidal thioethers.

PESTICIDAL COMPOSITIONS AND PROCESSES RELATED THERETO

This document discloses molecules having the following formula (“Formula One”): and processes related thereto.