2527-58-4

Basic information

• Product Name: 2,2'-dithiobis[N-methylbenzamide]
• Synonyms: 2,2'-dithiobis[n-methyl-benzamid];N-methyl-2-[2-(methylcarbamoyl)phenyl]disulfanylbenzamide;N-methyl-2-[2-(methylcarbamoyl)phenyl]disulfanyl-benzamide;Densil P;Dithio-2,2'-bis(N-methylbenzamide);2,2'-disulfanediylbis(N-MethylbenzaMide);2,2'-dithiobis[N-methylbenzamide];DITHIOMETHYLBENZAMIDE
• CAS NO: 2527-58-4
• Molecular Formula: C₁₆H₁₆N₂O₂S₂
• Molecular Weight: 332.44
• EINECS: 219-768-5
• Mol File: 2527-58-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 217-219℃
• Boiling Point: 545.9 °C at 760 mmHg
• Flash Point: 283.9 °C
• Appearance: /
• Density: 1.31
• PKA: 14.19±0.46(Predicted)
• CAS DataBase Reference: 2,2'-dithiobis[N-methylbenzamide](CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-dithiobis[N-methylbenzamide](2527-58-4)
• EPA Substance Registry System: 2,2'-dithiobis[N-methylbenzamide](2527-58-4)

Safety Data

• Hazardous Substances Data: 2527-58-4(Hazardous Substances Data)

Usage

General Description

2,2'-dithiobis[N-methylbenzamide] is a chemical compound that is commonly used as a cross-linking agent in the production of rubber, particularly in the vulcanization process. It is known for its ability to enhance the physical properties of rubber, such as its tensile strength and elasticity. The compound consists of two benzamide groups linked together by a dithio group, which gives it the ability to form strong cross-links within rubber molecules. This makes it an important additive in the production of tires, conveyor belts, and other rubber products that require high durability. However, it is important to handle this chemical with care, as it can be toxic if ingested or inhaled, and it may cause skin and eye irritation upon contact. Therefore, proper safety measures should be taken when working with 2,2'-dithiobis[N-methylbenzamide].

Synthetic route

2,2'-dithiodibenzoic acid dichloride (19602-82-5) + methylamine (74-89-5) → 2,2'-dithiobis(N-methylbenzamide) (2527-58-4)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 16h;	96%
In tetrahydrofuran at 0 - 20℃; for 11h; pH=9 - 10;	75%
In tetrahydrofuran at 0 - 20℃; for 16.6667h;	65%

2,2'-dithiodibenzoic acid dichloride (19602-82-5) + methylamine hydrochloride (593-51-1) → 2,2'-dithiobis(N-methylbenzamide) (2527-58-4)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	75%

2-bromo-N-methylbenzamide (61436-88-2) → 2,2'-dithiobis(N-methylbenzamide) (2527-58-4)

Conditions	Yield
With sodium sulfide hydrate; copper(l) chloride In 1-methyl-pyrrolidin-2-one; ethylene glycol at 70 - 100℃; for 6h;	69.8%

3H-1,2-benzodithiol-3-one (1677-27-6) + methylamine (74-89-5) → 2,2'-dithiobis(N-methylbenzamide) (2527-58-4)

Conditions	Yield
With ethanol

2,2'-dithiobenzoic acid (119-80-2) + methylamine (74-89-5) → 2,2'-dithiobis(N-methylbenzamide) (2527-58-4)

Conditions	Yield
(i) SOCl2, dioxane, (ii) /BRN= 741851/; Multistep reaction;

2-methyl-1,2-benzisothiazole-3(2H)-one (2527-66-4) + ethanol (64-17-5) + hydrogen sulfide (7783-06-4) → 2,2'-dithiobis(N-methylbenzamide) (2527-58-4)

Conditions	Yield
at 50℃;

2-methyl-1,2-benzisothiazole-3(2H)-one (2527-66-4) + sulfur dioxide → 2,2'-dithiobis(N-methylbenzamide) (2527-58-4)

Conditions	Yield
at 20℃;

2-methyl-α.β-benzisothiazolone → 2,2'-dithiobis(N-methylbenzamide) (2527-58-4)

Conditions	Yield
With ethanol; hydrogen sulfide at 50℃;
With ethanol; sulfur dioxide

2,2'-dithiobenzoic acid (119-80-2) → 2,2'-dithiobis(N-methylbenzamide) (2527-58-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 / 1 h / Heating 2: 147 g / benzene; tetrahydrofuran / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride / Reflux 2: dichloromethane / 0.5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride / N,N-dimethyl-formamide / 4 h / Reflux 2: tetrahydrofuran / 11 h / 0 - 20 °C / pH 9 - 10 View Scheme
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 42 h / 20 - 50 °C 2: tetrahydrofuran / 16 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; thionyl chloride / toluene / 20 h / 82 °C 2: tetrahydrofuran / 16.67 h / 0 - 20 °C View Scheme

methylamine (74-89-5) + Methyl thiosalicylate (4892-02-8) → 2,2'-dithiobis(N-methylbenzamide) (2527-58-4)

Conditions	Yield
In methanol; ethanol at 0 - 21℃; for 17h;	4.56 g

2,2'-dithiobis(N-methylbenzamide) (2527-58-4) → 2-methyl-1,2-benzisothiazole-3(2H)-one (2527-66-4)

Conditions	Yield
With chlorine; potassium iodide In 1,4-dioxane at 55 - 70℃; for 0.333333h;	92%
With tetrachloromethane durch Bromierung und Kochen des Reaktionsprodukts mit Eisessig;

2,2'-dithiobis(N-methylbenzamide) (2527-58-4) → 2-mercapto-N-methylbenzamide (20054-45-9)

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran; ethanol at 20℃; for 4h;	90%
With sodium tetrahydroborate; water In tetrahydrofuran at 20℃; Inert atmosphere;	89%
Stage #1: 2,2'-dithiobis(N-methylbenzamide) With sodium tetrahydroborate In ethanol at 0℃; for 9h; Stage #2: With hydrogenchloride In ethanol; water for 0.25h; pH=1.73;	72%

2,2'-dithiobis(N-methylbenzamide) (2527-58-4) + benzoic acid anhydride (93-97-0) → S-2-(methylcarbamoyl)phenyl benzothioate (1002759-79-6)

Conditions	Yield
Stage #1: 2,2'-dithiobis(N-methylbenzamide) With sodium tetrahydroborate In ethanol at 0 - 20℃; for 0.5h; Stage #2: benzoic acid anhydride With potassium carbonate In ethanol at 0 - 20℃; pH=9 - 10; Further stages.;	77%

2,2'-dithiobis(N-methylbenzamide) (2527-58-4) → N-methylsaccharin (15448-99-4)

Conditions	Yield
With dihydrogen peroxide; acetic acid at 100℃;

2,2'-dithiobis(N-methylbenzamide) (2527-58-4) → (2-methylcarbamoyl-phenylsulfanyl)-acetic acid (91950-10-6)

Conditions	Yield
With hydrogenchloride; ethanol; zinc Erwaermen des erhaltenen 2-Mercapto-N-methyl-benzamids mit Natrium-chloracetat und wss. Natronlauge;

2,2'-dithiobis(N-methylbenzamide) (2527-58-4) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2-(tetra-O-acetyl-β-D-glucopyranosylmercapto)-benzoic acid methylamide (114202-82-3)

Conditions	Yield
With potassium hydroxide; acetone

2,2'-dithiobis(N-methylbenzamide) (2527-58-4) + potassium acetate (127-08-2) + acetic anhydride (108-24-7) → 2-acetyl-3-hydroxybenzo[b]thiophene (3260-92-2) + benzo[b]thiophen-3-yl acetate (24434-82-0) + 3-hydroxy-benzothiophene-carboxylic acid-(2)-methylamide

Conditions	Yield
at 130℃;

2,2'-dithiobis(N-methylbenzamide) (2527-58-4) + dihydrogen peroxide (7722-84-1) + acetic acid (64-19-7) → N-methyl-saccharin

Conditions	Yield
at 100℃;

2,2'-dithiobis(N-methylbenzamide) (2527-58-4) → 2-(N-methylcarbamoyl)phenyl 4-methoxyphenyl sulfide (127905-51-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 40 percent / Zn; AcOH / 6 h / Heating 2: 74 percent / Cu2O / pyridine / 2 h / Heating View Scheme

2,2'-dithiobis(N-methylbenzamide) (2527-58-4) → 2-(N-methylcarbamoyl)phenyl 2-methoxyphenyl sulfide (127905-49-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 40 percent / Zn; AcOH / 6 h / Heating 2: 70 percent / Cu2O / pyridine / 2 h / Heating View Scheme

2,2'-dithiobis(N-methylbenzamide) (2527-58-4) → spiro(3H-2,1-benzoxathiol-3'-one-1,1'-3H-2,1-benzazathiol)-2-methyl-3-one (89784-57-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 40 percent / Zn; AcOH / 6 h / Heating 2: Cu2O / pyridine / 2 h / Heating 3: t-BuOCl / CH2Cl2 / 20 °C View Scheme

2,2'-dithiobis(N-methylbenzamide) (2527-58-4) → 2-<2-(N-methylcarbamoyl)phenylthio>benzoic acid (135781-45-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 40 percent / Zn; AcOH / 6 h / Heating 2: Cu2O / pyridine / 2 h / Heating View Scheme

2,2'-dithiobis(N-methylbenzamide) (2527-58-4) → 2-(N-methylcarbamoyl)phenyl 2-(methoxycarbonyl)phenyl sulfide (100695-82-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 40 percent / Zn; AcOH / 6 h / Heating 2: 70 percent / Cu2O / pyridine / 2 h / Heating View Scheme

2,2'-dithiobis(N-methylbenzamide) (2527-58-4) → bis[2-(N-methylcarbamoyl)phenyl] sulfoxide

Conditions	Yield
Multi-step reaction with 4 steps 1: 40 percent / Zn; AcOH / 6 h / Heating 2: Cu2O / pyridine / 2 h / Heating 3: t-BuOCl / CH2Cl2 / 20 °C 4: 78 percent / H2O / CH2Cl2 / 6 h / 20 °C View Scheme

2,2'-dithiobis(N-methylbenzamide) (2527-58-4) → 2-(N-methylcarbamoyl)phenyl 2-(methoxycarbonyl)phenyl sulfide (130138-88-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 40 percent / Zn; AcOH / 6 h / Heating 2: Cu2O / pyridine / 2 h / Heating View Scheme

2,2'-dithiobis(N-methylbenzamide) (2527-58-4) → 2-methyl-1-[2-(N-methylcarbamoyl)phenyl]-3-oxo-2,3-dihydro-1,2-benzothiazol-1-ium chloride

Conditions	Yield
Multi-step reaction with 3 steps 1: 40 percent / Zn; AcOH / 6 h / Heating 2: Cu2O / pyridine / 2 h / Heating 3: t-BuOCl / CH2Cl2 / 20 °C View Scheme

2,2'-dithiobis(N-methylbenzamide) (2527-58-4) → 2-(N-methylcarbamoyl)phenyl 4-methylphenyl sulfide (343869-27-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 40 percent / Zn; AcOH / 6 h / Heating 2: 74 percent / Cu2O / pyridine / 2 h / Heating View Scheme

2,2'-dithiobis(N-methylbenzamide) (2527-58-4) → 2-(N-methylcarbamoyl)phenyl 2-chlorophenyl sulfide (343869-25-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 40 percent / Zn; AcOH / 6 h / Heating 2: 66 percent / Cu2O / pyridine / 2 h / Heating View Scheme

2,2'-dithiobis(N-methylbenzamide) (2527-58-4) → 2-(N-methylcarbamoyl)phenyl 4-chlorophenyl sulfide (343869-28-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 40 percent / Zn; AcOH / 6 h / Heating 2: 74 percent / Cu2O / pyridine / 2 h / Heating View Scheme

2,2'-dithiobis(N-methylbenzamide) (2527-58-4) → 2-(N-methylcarbamoyl)phenyl 2-methylphenyl sulfide (343869-24-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 40 percent / Zn; AcOH / 6 h / Heating 2: 67 percent / Cu2O / pyridine / 2 h / Heating View Scheme

2,2'-dithiobis(N-methylbenzamide) (2527-58-4) → 2,3-dihydro-1-chloro-1-(4-methylphenyl)-2-methyl-3-oxo-1,2-benzisothiazole

Conditions	Yield
Multi-step reaction with 3 steps 1: 40 percent / Zn; AcOH / 6 h / Heating 2: 74 percent / Cu2O / pyridine / 2 h / Heating 3: 59 percent / t-BuOCl / CH2Cl2 / 20 °C View Scheme

Upstream product

• 1677-27-6 3H-1,2-benzodithiol-3-one 
• 74-89-5 methylamine 
• 19602-82-5 2,2'-dithiodibenzoic acid dichloride 
• 61436-88-2 2-bromo-N-methylbenzamide 
• 4892-02-8 Methyl thiosalicylate 
• 593-51-1 methylamine hydrochloride 
• 119-80-2 2,2'-dithiobenzoic acid 
• 2527-66-4 2-methyl-1,2-benzisothiazole-3(2H)-one 
• 64-17-5 ethanol 
• 7783-06-4 hydrogen sulfide 

Downstream Products

• 3260-92-2 2-acetyl-3-hydroxybenzo[b]thiophene 
• 24434-82-0 benzo[b]thiophen-3-yl acetate 
• 127905-51-5 2-(N-methylcarbamoyl)phenyl 4-methoxyphenyl sulfide 
• 127905-49-1 2-(N-methylcarbamoyl)phenyl 2-methoxyphenyl sulfide 
• 135781-45-2 2-<2-(N-methylcarbamoyl)phenylthio>benzoic acid 
• 100695-82-7 2-(N-methylcarbamoyl)phenyl 2-(methoxycarbonyl)phenyl sulfide 
• 130138-88-4 2-(N-methylcarbamoyl)phenyl 2-(methoxycarbonyl)phenyl sulfide 
• 343869-27-2 2-(N-methylcarbamoyl)phenyl 4-methylphenyl sulfide 
• 343869-25-0 2-(N-methylcarbamoyl)phenyl 2-chlorophenyl sulfide 
• 343869-28-3 2-(N-methylcarbamoyl)phenyl 4-chlorophenyl sulfide 
• 343869-24-9 2-(N-methylcarbamoyl)phenyl 2-methylphenyl sulfide 
• 343869-32-9 2-(N-methylcarbamoyl)phenyl 4-acetylphenyl sulfide 
• 252731-18-3 2-(N-methylcarbamoyl)phenyl 2-nitrophenyl sulfide 
• 343869-29-4 2-(N-methylcarbamoyl)phenyl 4-nitrophenyl sulfide 

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