34866-41-6

Basic information

• Product Name: 4H-1,3,5-Dithiazine,dihydro-5-(1-methylethyl)-(9CI)
• Synonyms: 4H-1,3,5-Dithiazine,dihydro-5-(1-methylethyl)-(9CI)
• CAS NO: 34866-41-6
• Molecular Formula: C₆H₁₃NS₂
• Molecular Weight: 163.30412
• Product Categories: ISOPROPYL
• Mol File: 34866-41-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4H-1,3,5-Dithiazine,dihydro-5-(1-methylethyl)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1,3,5-Dithiazine,dihydro-5-(1-methylethyl)-(9CI)(34866-41-6)
• EPA Substance Registry System: 4H-1,3,5-Dithiazine,dihydro-5-(1-methylethyl)-(9CI)(34866-41-6)

Safety Data

• Hazardous Substances Data: 34866-41-6(Hazardous Substances Data)

Upstream product

• 50-00-0 formaldehyd 
• 75-31-0 isopropylamine 
• 111184-80-6 isoprene 
• 75-09-2 dichloromethane 

Relevant articles and documents

Mono- and di-alkyl-[1,3,5]-dithiazinanes and their N-borane adducts revisited. Structural and theoretical study

Structural analyses of a series of 5-alkyl-[1,3,5]-dithiazinanes [R = Me (1), iPr (2), tBu (3)], their N-BH3 adducts (1BH3-3BH3) and their 2-alkyl (R0) derivatives are reported: R = Me, R0 = Me (7); R = Me, R0 iPr (8); R = iPr, R0 =Me (10); R = tBu, R0 =Me (11); and R = Me, R0 = nBu (12). The reaction of 2-lithium-5-methyl-[1,3,5]-dithiazinane (4) with I2 affords the bis-(5-methyl-[1,3,5]-dithiazinan-2-yl) (13). Isostructural compounds: [2,5,5]-trimethyl-[1,3,5]-dithiazinan-5-ium iodide (14), 5-borane-2,5-dimethyl- [1,3,5]-dithiazinane (15) and 2,5,5-trimethyl-[1,3,5,6]-dithiazaborata (16) are compared. Structures of 7, 8 and 10-13 were determined by 11B, 13C and 1H NMR and the X-ray diffraction analyses of 2, 1BH3, 13 and 14 are reported. Optimization of two chair conformers of heterocycles 1-3, 1BH3-3BH3, 7, 9 (R = Me, R0 = tBu), 13-16 were performed by HF/6-31++G and B3LYP/6-31G(d,p) methods and their minimum energy is compared. 2-Alkyl substituents or N-BH3 anchor the [1,3,5]-dithiazinane ring conformation allowing the analyses of steric and electronic interactions as well as the lone pairs effect in these molecules.

Benzotriazole mediated synthesis of some 5-alkyl-dihydro-4H-1,3,5- dithiazines

An efficient synthesis of N-substituted dihydro-4H-1,3,5-dithiazines is described. N,N-Bis(benzotriazolylmethyl)alkylamines 1 smoothly under go cyclisation reaction in the presence of formaldehyde and hydrogen sulfide to give 5-substituted dihydro-4H-1,3,5-dithiazines 2.

New chiral heterocycles: 5-[(R)-(+)-1'-methylbenzyl]-1,3,5-dithiazine and 3,7-di-[(R)-(+)-1'-methylbenzyl]-3,7-diaza-1,5-dithiacyclooctane. Conformational studies and their reactions with borane

We report herein the syntheses of a new 5-[(R)-(+)-1'-methylbenzyl)-1,3,5-dithiazine 1, the 5-isopropyl-1,3,5--dithiazine 2 and the 3,7-di-[(R)-(+)-1'-methylbenzyl]-3,7-diaza-1,5-dithiacyclooctane 3, two of them (1 and 3) are new sulfur and nitrogen heterocycles bearing a chiral N-substituent. Compounds 1 and 2 were found in conformational equilibrium when observed at rt at 1H-270 MHz or 13C-67.8 MHz, when cooling a preferred chair conformation was observed with the N-substituent in the axial position. Heterocycle 3 was in an anchored crown conformation at rt. A conformational study of ring inversions for 1 and 3 was performed and their thermodynamic data were obtained, ΔG° = 48.1 ± 0.8 for 1 and ΔG° = 64.8 ± 1.2 kJ/mol for 3. The reactivity of 1-3 with BH3-THF was investigated, the N- or S-BH3 adducts were not stable, the reactions afforded cleanly the N-borane-N-dimethyl-N-alkylamine adducts. The reactions of 3 with BD3 gave the N-BD3 adduct of [CH2D]2N-CH[CH3]C6H5. An X-ray diffraction study of 3 confirmed its crown conformation with the N-substituents in pseudo-axial position.