4426-75-9

Usage

InChI:InChI=1/C9H10S/c1-2-4-9-7-10-6-5-8(9)3-1/h1-4H,5-7H2

Upstream product

• 253-38-3 1H-isothiochromene 
• 38256-56-3 1-(2-bromo-ethyl)-2-bromomethyl-benzene 
• 344320-33-8 2-<2-(2-hydroxyethyl)-phenylmethylthio>-1,3-benzoxazole 
• 136843-31-7 1-thiacyclodec-5-ene-3,7-diyne 
• 17356-08-0 thiourea 
• 95675-86-8 2-ethyl-3,4-dihydro-1H-2-benzothiopyranium perchlorate 
• 6346-00-5 2-(2-hydroxyethyl)benzyl alcohol 
• 4410-99-5 2-mercaptophenylethane 
• 3970-21-6 2-Methoxyethoxymethyl chloride 
• 493-05-0 isochromane 
• 122444-35-3 2-(2-bromomethyl)-phenethyl alcohol 
• 64-17-5 ethanol 
• 7732-18-5 water 

Downstream Products

• 108277-71-0 3,4-dihydro-1-phenylethynyl-1H-2-benzothiopyran 
• 108446-98-6 1-vinylisothiochroman S-(p-toluenesulfonyl)imide 
• 108447-00-3 4-(p-toluenesulfonyl)-1,2,4,5-tetrahydro-3,4-benzothiazonine 
• 83501-57-9 1-Benzyl-1-isothiochromancarbaldehyd 
• 68099-90-1 C₁₈H₂₀N₂O₂S₂ 
• 68099-91-2 C₂₂H₂₄N₂O₄S₂ 
• 68099-92-3 2,2'-(Dithiodiethylen)-dibenzonitril 
• 1428485-04-4 2-(isothiochroman-1-yl)-1-phenylethanone 
• 80253-06-1 2-(methylsulfanylmethyl)styrene 
• 97318-32-6 1-phenyl-3,4-dihydro-1H-2-benzothiopyran 

Relevant academic research and scientific papers

Alkylthioether synthesis via imidazole mediated Mitsunobu condensation

Unsymmetric alkylthioethers can be prepared from aliphatic thiols and unhindered alcohols under modified Mitsunobu conditions using trimethylphosphine/1,1'-(azodicarbonyl)dipiperdine (ADDP) in the presence of imidazote (2 equivalents).

SYNTHESIS OF A SULFUR-CONTAINING 10-MEMBERED ENEDIYNE MODEL COMPOUND RELATED TO THE ESPERAMICIN/CALICHEAMICIN/DYNEMICIN AGLYCONES

Synthesis of the 10-membered heterocyclic enediyne 4 and its conversion to the benzenoid adduct 10 via the Bergman reaction are described.

Indium-catalyzed direct conversion of dibenzyl ethers to dibenzyl sulfides using elemental sulfur and a hydrosilane and its application to the preparation of benzyl selenides

Described herein is a catalytic system composed of an indium(III) compound, a hydrosilane and an easily handled form of elemental sulfur (S8) that effectively and directly catalyzes the sulfidation of dibenzyl ethers to produce dibenzyl sulfides. This system could also be applied to selenium in a straightforward conversion to dibenzyl selenides.

Manganese dioxide-methanesulfonic acid promoted direct dehydrogenative alkylation of sp3 C-H bonds adjacent to a heteroatom

A manganese dioxide (MnO2)-methanesulfonic acid (CH 3SO3H) oxidation system has been developed to efficiently promote direct coupling of benzylic ethers and carbamates with simple ketones via oxidative C-H bond activation.

General procedure for the synthesis of ortho-vinylbenzyl-substituted amines, ethers, and sulfides

A convenient procedure has been proposed for the synthesis ortho-vinylbenzyl-substituted ethers, amines, and sulfides via reaction of o-(2-bromoethyl)benzyl bromide with various nucleophiles.

Nucleophilic Substitution Factors. 1. Coplanar vs. Orthogonal Bimolecular Substitution at a Benzylic Carbon. X-ray Structure of 2-Isobutyl-1,3-dihydrobenzothiophenium Perchlorate

A stereoelectronic effect in bimolecular nucleophilic substitution at a benzylic center has been observed in the rates of reaction of thiourea in dimethyl-d6 sulfoxide with a series of sulfonium perchlorates with differing degrees of constraint in the orientation of the reacting C-S+ bond with respect to the plane of the aromatic ring.The substrates and their relative rates (at 37 deg C, unless otherwise noted) are as follows: (a, highly constrained) 2-ethyl-1,3-dihydrobenzothiophenium perchlorate (4b), 1,00, and 2-isobutyl-1,3-dihydrobenzothiophenium perchlorate (4c), 2.8; (b, partly constrained) 2-ethyl-3,4-dihydro-1H-2-benzothiopyranium perchlorate (7), 45 (at 82 deg C); (c, unconstrained) S,S-dibenzyl-S-ethylsulfonium perchlorate (5b), 8.1*103.An (8*103-fold rate difference was also observed between S,S-dibenzyl-S-ethylsulfonium terafluoroborate (5a) and 2-ethyl-1,3-dihydrobenzothiophenium tetrafluoroborate (4a) with potassium thiocyanate-18-crown-6 in acetonitrile-d3.Analysis of these rate differences, taken with inspection of molecular models which show that the observed rate differences are not adequately accounted for by simple nonbonding or angle strain effects, clearly indicates a dihedral angle dependent factor consistent with ?-overlap between p-orbitals on the aromatic ring and the carbon atom undergoing substitution.The "orbital-overlap factor" is estimated to increase the reactivity of the benzylic center in 5b (4*103-fold relative to that of the corresponding ethyl group (in 21).A single-crystal X-ray analysis on 4c showed the salt crystallizes in space group P21/n, unit cell dimensions a = 17.382 (1) Angstroem, b = 9.1731(6) Angstroem, c = 8.7828 (3) Angstroem, and β = 91.7 (2) deg, with Z = 4.On the basis of 2054 unique data with F2 > 2?, full matrix refinement converged at R = 0.044 for 232 variables.There is a dihedral angle of 3.8 deg between the C2,S,C9 plane and the plane of the aromatic ring consistent with the observed low reactivity of the benzylic center and the present analysis.The entropies of activation for benzylic substitution of the cyclic and acyclic substrates (4b, 4c, and 5b) with thiourea in Me2SO-d6 are very similar (-12 +/- 1 cal mol-1 K-1), in contrast to the great ΔS(excit.) difference reported for an analogous α-carbonyl system by Bartlett and Trachtenberg; the origin of this difference is discussed.