135-58-0

Basic information

• Product Name: mesulfen
• Synonyms: 2,7-Dimethylthianthrene;Cutilen;Cutosolo;Mesulfen;Mesulphen;Mitabol;Mitigal;Neosulfine;Odylen;Peligal;Scabol;Sudermo;Thianthol;Thianthrol
• CAS NO: 135-58-0
• Molecular Formula: C₁₄H₁₂S₂
• Molecular Weight: 244.37508
• EINECS: 205-202-4
• Mol File: 135-58-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 382.092 °C at 760 mmHg
• Flash Point: 191.269 °C
• Appearance: /
• Density: 1.237 g/cm³
• Vapor Pressure: 1.06E-05mmHg at 25°C
• Refractive Index: 1.685
• CAS DataBase Reference: mesulfen(CAS DataBase Reference)
• NIST Chemistry Reference: mesulfen(135-58-0)
• EPA Substance Registry System: mesulfen(135-58-0)

Safety Data

• Hazardous Substances Data: 135-58-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H12S2/c1-9-3-5-11-13(7-9)15-12-6-4-10(2)8-14(12)16-11/h3-8H,1-2H3

Synthetic route

di(4-methyl)phenylthiosulfonate (2943-42-2) → Mesulfen (135-58-0)

Conditions	Yield
With sulfuric acid

bis-(2-iodo-5-methyl-phenyl)-disulfide → Mesulfen (135-58-0)

Conditions	Yield
With copper at 180℃;

tetra(p-tolyl)tin (6746-22-1) → Mesulfen (135-58-0)

Conditions	Yield
With sulfur at 190℃;

para-thiocresol (106-45-6) → Mesulfen (135-58-0)

Conditions	Yield
With sulfuric acid
With sulfuric acid at 20℃;

toluene (108-88-3) → Mesulfen (135-58-0)

Conditions	Yield
With aluminium trichloride; sulfur dichloride at -15℃; dann auf etwa +40grad;
With disulfur dichloride; aluminium trichloride
With disulfur dichloride
With disulfur dichloride; aluminium amalgam
With disulfur dichloride; aluminium

4-methylphenyl 2-pyridyl disulfide (860413-72-5) + sulfuric acid (7664-93-9) → Mesulfen (135-58-0)

6-methyl-benzo-1.2.3-thiodiazole → Mesulfen (135-58-0)

Conditions	Yield
at 200 - 220℃;

bis(3-methylphenyl)disulfide (20333-41-9) → Mesulfen (135-58-0) + C14H12S2 (1207270-56-1) + 1,8-dimethylthianthrene (1207270-57-2)

Conditions	Yield
With molybdenum(V) chloride In dichloromethane at 20℃; for 1.5h; Inert atmosphere;

Mesulfen (135-58-0) → 2,7-dimethyl-thianthrene-5,5,10-trioxide

Conditions	Yield
With dihydrogen peroxide; acetic acid

Mesulfen (135-58-0) → 5,5,10,10-tetraoxo-5λ6,10λ6-thianthrene-2,7-dicarboxylic acid (96473-63-1)

Conditions	Yield
With chromium(VI) oxide; acetic acid

Mesulfen (135-58-0) → trans-2,7-dimethylthianthrene-5,10-dioxide (96196-28-0) + 2,7-dimethyl-thianthrene-5r,10c-dioxide (96196-28-0)

Conditions	Yield
With dihydrogen peroxide; acetic acid
With dihydrogen peroxide; acetic acid

Mesulfen (135-58-0) + dihydrogen peroxide (7722-84-1) + acetic acid (64-19-7) → 2.6-dimethyl-thianthrene-bis-

Mesulfen (135-58-0) + nitric acid (7697-37-2) → 2.6-dimethyl-thianthrene-bis-

Mesulfen (135-58-0) + nitric acid (7697-37-2) + acetic acid (64-19-7) → 2.6-dimethyl-thianthrene-S oxide

Mesulfen (135-58-0) → 2,7-dimethylthianthrene-5,10-dioxide cis + trans-2,7-dimethylthianthrene-5,10-dioxide (96196-28-0)

Conditions	Yield
With dihydrogen peroxide

Mesulfen (135-58-0) → 2,7-dimethyl-thianthrene-5,5-dioxide

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous hydrogen peroxide; acetic acid 2: zinc-powder; acetic acid View Scheme

Mesulfen (135-58-0) → 5,5,10,10-tetraoxo-5λ6,10λ6-thianthrene-2,7-dicarboxylic acid dimethyl ester (97594-70-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: chromium (VI)-oxide; acetic acid 2: diethyl ether View Scheme

Upstream product

• 2943-42-2 di(4-methyl)phenylthiosulfonate 
• 6746-22-1 tetra(p-tolyl)tin 
• 106-45-6 para-thiocresol 
• 108-88-3 toluene 
• 860413-72-5 4-methylphenyl 2-pyridyl disulfide 
• 7664-93-9 sulfuric acid 
• 20333-41-9 bis(3-methylphenyl)disulfide 
• 103-19-5 di(p-tolyl) disulfide 
• 53484-09-6 Tris(5-methyl-1,3,2-benzodithiaborol-2-yl)amine 

Relevant articles and documents

Ring inversion dynamics of derivatives of thianthrene di- and tetraoxide

The ring inversion barrier for thianthrene tetraoxide was determined by making use of the variable temperature 13C NMR spectra of the 2,7-diisopropyl derivative (ΔG? = 6.5 kcal mol-1). The barrier is lower than that measured for a trans thianthrene dioxide derivative (ΔG? = 9.35 kcal mol-1). These results agree well with ab initio theoretical predictions.

RADIKALIONEN 89. EINELEKTRONEN-OXIDATIONEN VON DIARYLDISULFIDEN MIT AlCl3/H2CCl2

The single electron oxidation of 14 alkyl and alkoxy substituted diaryldisulfides by AlCl3/H2CCl2 has been investigated by ESR/ENDOR spectroscopy.The radical cations observed prove the following skeletal rearrangements: Those with ring hydrogens in ortho positions to the disulfide bridge preferentially form thianthrene derivatives.The isomeric dinaphthyl disulfides react differently, the 2,2'-isomer yielding the dibenzothianthrene radical cation and the 1,1'-isomer the well-known naphthalene-1,8-disulfide radical cation.For all diaryl disulfides with completely alkyl- or methoxy-blocked ortho positions, oxidative desulfuration is observed.As substantiated by additional (2)D and (33)S isotope marking, the bis(2,5-dimethoxyphenyl)disulfide reacts both to the corresponding thianthrene derivative as well as via desulfuration to the radical cation of the monosulfide.Accompanying cyclovoltammetric and photoelectron spectroscopic measurements prove that all ESR spectroscopically detected radical cations result from compounds Ar-S-Ar, Ar-SS-Ar and Ar(S)2Ar with rather low oxidation or ionisation potentials and thus suggest that each the most easily oxidized paramagnetic species is observed in the rather complex product mixtures, which form on AlCl3/H2CCl2 oxidation of diaryldisulfides. Key words: Diaryl disulfides; one-electron oxidation; radical cations; ESR/ENDOR spectra.