496-74-2

Basic information

• Product Name: TOLUENE-3,4-DITHIOL
• Synonyms: 1-METHYL-3,4-DIMERCAPTOBENZENE;1,2-DIMERCAPTO-4-METHYLBENZENE;4-METHYL-1,2-BENZENEDITHIOL;4-METHYL-1,2-DIMERCAPTOBENZENE;3,4-DIMERCAPTOTOLUENE;3,4-TOLUENEDITHIOL;DITHIOL;'DITHIOL'
• CAS NO: 496-74-2
• Molecular Formula: C7H8S2
• Molecular Weight: 156.27
• EINECS: 207-828-3
• Product Categories: Charge Transfer Complexes (Synthetic Intermediates);Charge Transfer Complexes for Organic Metals;Functional Materials;Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;aromatic mercaptan
• Mol File: 496-74-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 30-33 °C(lit.)
• Boiling Point: 135-137 °C17 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White to yellow/Crystalline Low Melting Solid
• Density: 1.179 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.015mmHg at 25°C
• Refractive Index: 1.6180 (estimate)
• Storage Temp.: −20°C
• Solubility: Soluble in benzene and aqueous alkali hydroxide solutions
• PKA: 6.29±0.48(Predicted)
• Sensitive: Air Sensitive
• Stability: Stable. Incompatible with strong oxidizing agents, strong bases.
• Merck: 14,9531
• BRN: 1635270
• CAS DataBase Reference: TOLUENE-3,4-DITHIOL(CAS DataBase Reference)
• NIST Chemistry Reference: TOLUENE-3,4-DITHIOL(496-74-2)
• EPA Substance Registry System: TOLUENE-3,4-DITHIOL(496-74-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-36/37/39
• RIDADR: 3071
• WGK Germany: 3
• RTECS: XT2275000
• F: 13
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 496-74-2(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Uses

Different sources of media describe the Uses of 496-74-2 differently. You can refer to the following data:
1. For the detection of bismuth, molybdenum, rhenium, tin, tungsten, see Bickford et al., J. Am. Pharm. Assoc. Sci. Ed. 37, 255 (1948).
2. Used to generate the corresponding dithiolate ligand in a study of dinuclear gold(I) dithiolate complexes.
3. Toluene-3,4-dithiol may be suitable as colorimetric reagent for the determination of technetium using spectrophotometry.

General Description

Toluene-3,4-dithiol with molybdenum(VI) in mineral acid forms dark-green coloured complex. It is purified by vacuum distillation under nitrogen.

InChI:InChI=1/C7H8S2/c1-5-2-3-6(8)7(9)4-5/h2-4,8-9H,1H3/p-2

Synthetic route

5-methyl-2-mercaptobenzenesulfonyl chloride → 3,4-dimercaptotoluene (496-74-2)

Conditions	Yield
Stage #1: 5-methyl-2-mercaptobenzenesulfonyl chloride With iron In water at 0℃; for 0.5h; Stage #2: With hydrogenchloride In water for 2.5h; Reagent/catalyst; Reflux;	98%

Methoxy-2-benzo-4,5-methyl-7-dithiaphospholan-1,3,2 (57093-52-4) → 3,4-dimercaptotoluene (496-74-2)

Conditions	Yield
With methanol In benzene at 80℃; for 12h;

2,8-dimethyldibenzotetrathiocin (66086-39-3) → 3,4-dimercaptotoluene (496-74-2)

Conditions	Yield
With 2-hydroxyethanethiol In d(4)-methanol; water-d2 at 25℃; Equilibrium constant; phosphate buffer(0.5 mM, pH 7.0);

toluene-disulfonic acid-(3.4)-dichloride → 3,4-dimercaptotoluene (496-74-2)

Conditions	Yield
With hydrogenchloride; tin

7-methyl-1,2,3,4,5-benzopentathiepin (109988-33-2) → 3,4-dimercaptotoluene (496-74-2)

Conditions	Yield
With triethylamine; 2-hydroxyethanethiol In chloroform at 25℃; for 0.5h;

dimethyl-(5-methyl-benzo[1,3,2]dithiaphosphol-2-yl)-amine (53827-17-1) → 3,4-dimercaptotoluene (496-74-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: benzene / 5 h / 20 °C 2: MeOH / benzene / 12 h / 80 °C View Scheme

3,4-dimercaptotoluene (496-74-2) + methyl 10-oxoundecanoate (18993-09-4) → methyl 10,10-toluene-3,4-disulphideundecanoate (130891-85-9)

Conditions	Yield
With boron trifluoride diethyl etherate; acetic acid for 0.25h; Ambient temperature;	99%

3,4-dimercaptotoluene (496-74-2) + octaperfluorocyclopentene (559-40-0) → 1,1,2,2,3,3-hexafluoro-6-methyl-2,3-dihydro-1H-benzocyclopenta-p-dithiine (110890-06-7)

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Ambient temperature;	98%

3,4-dimercaptotoluene (496-74-2) + N-(4-Nitrobenzoyl)-1-pyrrolidinecarbimidoyl Chloride (76098-31-2) → N-(5-Methyl-1,3-benzodithiol-2-yliden)-4-nitrobenzamid (81322-25-0)

Conditions	Yield
With triethylamine In 1,2-dimethoxyethane for 24h; Ambient temperature;	98%

3,4-dimercaptotoluene (496-74-2) + Isopropyl isocyanate (1795-48-8) → 4-Methyl-phenylen-1,2-bis(N-isopropylthiolurethan)

Conditions	Yield
N-benzyl-trimethylammonium hydroxide In diethyl ether at 20℃; for 2h;	98%

3,4-dimercaptotoluene (496-74-2) + dimethoxydiphenylmethane (2235-01-0) → 5-methyl-2,2-diphenylbenzo[d][1,3]dithiol

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 12h; Reagent/catalyst; Solvent; Temperature; Reflux; Dean-Stark;	98%

3,4-dimercaptotoluene (496-74-2) + diphenyltin(IV) dichloride (1135-99-5) → (C6H5)2Sn(CH3C6H3S2) (4312-02-1)

Conditions	Yield
With KOH In water soln. of ligand and KOH in H2O was added to suspn. of Sn-complex in H2Ounder stirring for 15 min, ppt. was extd. with ether; dried over Na2SO4, filtered, solvent was evapd., recrystd. from benzeneand hexane;	97%
With KOH In methanol; water mixt. of KOH and dithiol in methanol is homogenized by shaking at room temp., pH value is adjusted to 7 by addn. of 2 N HCl, soln. of Ph2SnCl2 in water is added during 0.5 h with vigorous stirring; after 1 h ppt. is filtered off, washed with H2O, dried in vac. and dissolved in CH2Cl2, soln. is dried over Na2SO4, product is precipitated by addn. of n-hexane, recrystn. from CHCl3, elem. anal.;	44%

3,4-dimercaptotoluene (496-74-2) + methyl Nτ-(3-chloroquinoxalin-2-yl)-L-histidinate → 2-methyl-5,12-dithianaphtho<2,3-b>quinoxaline (106161-11-9)

Conditions	Yield
With dipotassium hydrogenphosphate In water; N,N-dimethyl-formamide at 20℃; for 0.166667h;	97%

3,4-dimercaptotoluene (496-74-2) → 2-Chloro-5-methyl-1,3,2-benzodithiaphosphole (57351-95-8)

Conditions	Yield
With phosphorus trichloride In dichloromethane at 20℃; for 24h; Inert atmosphere; Schlenk technique;	96%
With phosphorus trichloride In benzene
With phosphorus pentachloride; triethylamine In diethyl ether for 2h; Ambient temperature;
Multi-step reaction with 2 steps 1: 64.2 percent / triethylamine / diethyl ether / 3 h / Heating 2: phosphorus pentachloride / toluene / 10 h / Heating View Scheme
Multi-step reaction with 2 steps 1: phosphorus pentachloride / CH2Cl2 / -10 °C 2: toluene-3,4-dithiol / CH2Cl2 / 16 h / Ambient temperature View Scheme

3,4-dimercaptotoluene (496-74-2) + dimethyltin dichloride (753-73-1) → [Sn(CH3)2(3,4-toluenedithiolate)] (4312-00-9)

Conditions	Yield
With KOH In ethanol; water treatment of dithiol with KOH (in EtOH) for 15 min, addn. of 1 equiv. aq. Me2SnCl2, stirring for 30 min (pptn.); collection (filtration); elem. anal.;	96%
With KOH In methanol; water mixt. of KOH and dithiol in methanol is homogenized by shaking at room temp., pH value is adjusted to 7 by addn. of 2 N HCl, soln. of Me2SnCl2 in water is added during 0.5 h with vigorous stirring; after 1 h ppt. is filtered off, washed with H2O, dried in vac. and dissolved in CH2Cl2, soln. is dried over Na2SO4, product is precipitated by addn. of n-hexane, recrystn. from CHCl3, elem. anal.;	46%

3,4-dimercaptotoluene (496-74-2) + oxotitanium(IV) meso-tetraphenylporphinato (58384-89-7) → (3,4-toluenedithiolato)(tetraphenylporphyrinato)titanium(IV) CH3OH

Conditions	Yield
With methanol In dichloromethane stirring at room temp. under Ar, TLC on silica gel, concg. of the soln., addn. of methanol; elem. anal.;	96%

3,4-dimercaptotoluene (496-74-2) + C8H8Cl2N4O2 → N2,N3,7-trimethylbenzo[5,6][1,4]dithiino[2,3-b]pyrazine-2,3-dicarboxamide

Conditions	Yield
With dipotassium hydrogenphosphate In water; N,N-dimethyl-formamide at 20℃; for 0.166667h;	96%

2,3-dichloroquinoxaline (2213-63-0) + 3,4-dimercaptotoluene (496-74-2) → 2-methyl-5,12-dithianaphtho<2,3-b>quinoxaline (106161-11-9)

Conditions	Yield
With dipotassium hydrogenphosphate In water; N,N-dimethyl-formamide at 20℃; for 0.166667h;	95%
With ammonia; sodium; iron(III) chloride 1.) -33 deg C, 2.) irradiation, -33 deg C, 180 min; Yield given. Multistep reaction;

3,4-dimercaptotoluene (496-74-2) + methyl 12-oxooctadecanoate (2380-27-0) → methyl 12,12-toluene-3,4-disulphideoctadecanoate (130891-86-0)

Conditions	Yield
With boron trifluoride diethyl etherate; acetic acid for 0.5h; Ambient temperature;	95%

3,4-dimercaptotoluene (496-74-2) + 9,10-diketostearic acid (656-73-5) → 9,9,10,10-bis(toluene-3,4-disulphide)octadecanoic acid (130911-99-8)

Conditions	Yield
With boron trifluoride diethyl etherate; acetic acid for 1h; Ambient temperature;	95%

Upstream product

• 66086-39-3 2,8-dimethyldibenzotetrathiocin 
• 3460-29-5 4-nitro-2,5-xylidine 
• 73713-69-6 2,5-Dimethyl-4-nitrobenzonitrile 
• 53827-17-1 dimethyl-(5-methyl-benzo[1,3,2]dithiaphosphol-2-yl)-amine 
• 109988-33-2 7-methyl-1,2,3,4,5-benzopentathiepin 
• 57093-52-4 Methoxy-2-benzo-4,5-methyl-7-dithiaphospholan-1,3,2 

Downstream Products

• 100146-01-8 3,4-bis-benzoylmercapto-toluene 
• 73486-36-9 2-benzoylmethyl-5-methyl-2-phenyl-1,3-benzodithiole 
• 29690-14-0 4-methyl-1,2-di(methylthio)benzene 
• 7783-06-4 hydrogen sulfide 
• 126975-34-6 C₁₃H₂₀O₂S₂Ti 
• 67-63-0 isopropyl alcohol 
• 113230-66-3 {Mo(H)2(S₂C₆H₃CH₃)(PCH₃(C₆H₅)2)3} 
• 113230-68-5 {Mo(S₂C₆H₃CH₃)2(PCH₃(C₆H₅)2)2} 
• 530099-71-9 [Ru(dimethyl sulfoxide)(3,4-toluenedithiolato)(2,2':6',2''-terpyridine)] 
• 81097-99-6 Ni(1,2-bis(diphenylphosphino)ethane)(toluene-3,4-dithiolate) 
• 87006-51-7 Cd⁽²⁺⁾*CH₃C₆H₃S₂^(2-)=Cd(CH₃C₆H₃S₂) 

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