196872-08-9

Basic information

• Product Name: 3,3-bis(trifluoromethyl)-4,4-dimethyl-2-(phenylsulfonyl)-1-thia-2-aza-4-azonia-3-boratacyclobutan-1-one
• CAS NO: 196872-08-9
• Molecular Weight: 396.142
• Mol File: 196872-08-9.mol

Chemical Properties

• CAS DataBase Reference: 3,3-bis(trifluoromethyl)-4,4-dimethyl-2-(phenylsulfonyl)-1-thia-2-aza-4-azonia-3-boratacyclobutan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3-bis(trifluoromethyl)-4,4-dimethyl-2-(phenylsulfonyl)-1-thia-2-aza-4-azonia-3-boratacyclobutan-1-one(196872-08-9)
• EPA Substance Registry System: 3,3-bis(trifluoromethyl)-4,4-dimethyl-2-(phenylsulfonyl)-1-thia-2-aza-4-azonia-3-boratacyclobutan-1-one(196872-08-9)

Safety Data

• Hazardous Substances Data: 196872-08-9(Hazardous Substances Data)

Upstream product

• 6536-23-8 N-sulfinylbenzenesulfonamide 
• 105224-90-6 dimethylaminobis(trifluoromethyl)borane 

Relevant articles and documents

Novel [2 + 2] cycloaddition reactions of (dimethylamino)bis(trifluoromethyl)borane, (CF3)2BNMe2, with N-sulfinylsulfonamides, aminoiminophosphines, carbodiimides, and a keteneimine

(Dimethylamino)bis(trifluoromethyl)borane, (CF3)2BNMe2 (1), combines with NT-sulfinyl-sulfonamides R-O2S-N=S=O in a [2 + 2] fashion to form (CF3)2B-NMe2-S(O)-N-SO2R (R = Me (2a), Et (2b), iPr (2c), Ph (2d), and pTol (2e)). Aminoiminophosphines RN=P-NR2′ react with 1 analogously to yield the heterocycles (CF3)2B-NMe2-P(NR2′)-NR (R = SiMe3, NR2′ = N(SiMe3)2 (3a), TMP (3b); R = tBu, NR2′ = N(SiMe3)tBu (3c), NiPr2 (3d), TMP (3e)). Carbodiimides R-N=C=N-R add to the B=N bond of 1 to give unstable adducts (CF3)2B-NMe2-C(NR)-NR which rearrange at 20 °C to yield the four-membered heterocycles (CF3)2B-NR-C(NMe2)-NR (R = iPr (5a), cC6H11 (5b)). For carbodiimides with aryl substituents R = pXC6H4, this rearrangement competes with an internal electrophilic aromatic substitution reaction and mixtures of the two isomers (CF3)2B-NC6H4X-C(NMe 2)-NC6H4X (X = H (5c), Me (5d), OMe (5e)) and (CF3)2B-CCHCXCHCHC-NH-C(NMe2)-N-(C 6H4X) (X = H (6c), Me (6d), OMe (6e)) are obtained. Ph-N=C=CMe2 combines with 1 to form the four-membered ring (CF3)2B-CMe2-C(NMe2)-NPh (8). F3C-CH2-N=S=O undergoes an ene-type reaction with 1 by which the dimethylamine borane (F3C-HC=N-S-(=O))(CF3)2B-NHMe2 (9) is formed. The constitution of the novel boron compounds has been deduced from multinuclear NMR, IR, and mass spectra. The structures of 2a, 3c, 5c, 6d, 6e, and 8 have been investigated by single-crystal X-ray diffraction.