61832-41-5

Basic information

• Product Name: N-Methyl-1-(methylthio)-2-nitroethylen-1-amine
• Synonyms: N-Methyl-1-(methylth;Methyl (1Z)-N-Methyl-2-nitroethaniMidothioate;1-(Methylthio)-2-nitro-N-MethylethyleneaMine;2-(Methylthio)-2-(MethylaMino)-1-nitroethene;Nizatidine EP IMpurity B;(E)-N-Methyl-1-(Methylthio)-2-nitroethenaMine;1-(Methylamino)-1-(methylthio)-2-nitroethylene, N-Methyl-1-(methylsulphanyl)-2-nitroethenamine;N-Methyl-1-(methylthio)-2-nitroethenamine
• CAS NO: 61832-41-5
• Molecular Formula: C₄H₈N₂O₂S
• Molecular Weight: 149.19
• EINECS: 263-266-9
• Product Categories: Sulfur Compounds;Intermediates;Sulfur & Selenium Compounds;PHARMACEUTICAL INTERMEDIATES;Anilines, Aromatic Amines and Nitro Compounds;Amines;(intermediate of ranitidine);Organic Building Blocks;Sulfides/Disulfides
• Mol File: 61832-41-5.mol
• Article Data: 15

Chemical Properties

• Melting Point: 112-118 °C(lit.)
• Boiling Point: 236.5 °C at 760 mmHg
• Flash Point: 96.8 °C
• Appearance: /
• Density: 1.199 g/cm³
• Vapor Pressure: 0.168mmHg at 25°C
• Refractive Index: 1.533
• PKA: 0.86±0.70(Predicted)
• BRN: 2828017
• CAS DataBase Reference: N-Methyl-1-(methylthio)-2-nitroethylen-1-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methyl-1-(methylthio)-2-nitroethylen-1-amine(61832-41-5)
• EPA Substance Registry System: N-Methyl-1-(methylthio)-2-nitroethylen-1-amine(61832-41-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• RIDADR: UN 3335
• WGK Germany: 3
• Hazardous Substances Data: 61832-41-5(Hazardous Substances Data)

Usage

Description

N-Methyl-1-(methylthio)-2-nitroethylen-1-amine, also known as (E)-N-methyl-1-(methylthio)-2-nitroethenamine (NMSM), is an organic compound that serves as an intermediate in the synthesis of various pharmaceuticals. It is a yellow solid with specific chemical properties that make it a valuable component in the production of certain drugs.

Uses

Used in Pharmaceutical Industry:
N-Methyl-1-(methylthio)-2-nitroethylen-1-amine is used as an intermediate in the synthesis of Ranitidine and Nizatidine, which are H2 receptor antagonists used to treat conditions like peptic ulcers, gastroesophageal reflux disease (GERD), and other acid-related disorders.
Additionally, NMSM may be used for the synthesis of other compounds such as pyrano[2,3-c]pyrazol-6-amines and 6-methoxy-N-methyl-3-nitro-4-nitromethyl-4H-chromen-2-amine, which could potentially have applications in various fields, including pharmaceuticals and chemical research.

InChI:InChI=1/C4H8N2O2S/c1-5-4(9-2)3-6(7)8/h3H2,1-2H3/b5-4-

Synthetic route

methylamine (74-89-5) + 1,1-di(methylsulfanyl)-2-nitroethylene (13623-94-4) → (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5)

Conditions	Yield
In ethanol for 5h; Reflux;	75%

methylamine hydrochloride (593-51-1) + 1,1-di(methylsulfanyl)-2-nitroethylene (13623-94-4) → (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5)

Conditions	Yield
With potassium carbonate In dichloromethane

1-(n-methylsulfinyl)-1-(n-methylthio)-2-nitroethene (61832-49-3) → (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5)

Conditions	Yield
With methylamine In methanol

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + benzaldehyde (100-52-7) → N,1-dimethyl-6-(methylthio)-3,5-dinitro-4-phenyl-1,4-dihydropyridin-2-amine (1620024-38-5)

Conditions	Yield
With toluene-4-sulfonic acid In water at 20℃; for 0.25h; Catalytic behavior; Solvent; Reagent/catalyst; Green chemistry;	98%
In neat (no solvent) at 100℃; for 0.166667h; Temperature; Solvent; Reagent/catalyst; Microwave irradiation; Green chemistry;	94%
With 2-aminopyridine In ethanol at 80℃; for 5h;	92%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 3-methoxy-2-hydroxybenzaldehyde (148-53-8) → N-[8-methoxy-4-(methylsulfanyl)-3-nitro-4H-2-chromenyl]-N-methylamine (1173429-63-4)

Conditions	Yield
With cholin hydroxide In water at 20℃; for 5h; Green chemistry;	96%
Stage #1: 3-methoxy-2-hydroxybenzaldehyde With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 20℃; Stage #2: (E-)-N-methyl-1-(methylthio)-2-nitroethanamine In methanol at 20℃; for 15h;	85%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + ethyl acetoacetate (141-97-9) + 2-methylphenyl aldehyde (529-20-4) + phenylhydrazine (100-63-0) → 4-(2-methylphenyl)-N,3-dimethyl-5-nitro-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazol-6-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol Reflux;	96%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 3,4,5-trimethoxy-benzaldehyde (86-81-7) + β-naphthol (135-19-3) → 1-(3,4,5-trimethoxyphenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

Conditions	Yield
In ethanol; water at 60℃; for 0.583333h; Green chemistry;	96%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-methoxy-benzaldehyde (123-11-5) + β-naphthol (135-19-3) → 1-(4-methoxyphenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

Conditions	Yield
In ethanol; water at 60℃; for 0.6h; Green chemistry;	96%

2,7-Dihydroxynaphthalene (582-17-2) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-methoxy-benzaldehyde (123-11-5) → 1-(4-methoxyphenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-9-ol

Conditions	Yield
In ethanol; water at 60℃; for 0.583333h; Green chemistry;	96%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-ethoxybenzaldehyde (10031-82-0) + β-naphthol (135-19-3) → 1-(4-ethoxyphenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

Conditions	Yield
In ethanol; water at 60℃; for 0.583333h; Green chemistry;	96%

piperonal (120-57-0) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + β-naphthol (135-19-3) → 1-(benzo[d][1,3]dioxol-6-yl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

Conditions	Yield
In ethanol; water at 60℃; for 0.616667h; Green chemistry;	96%

1H-benzimidazol-2-amine (934-32-7) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-methyl-benzaldehyde (104-87-0) → N-methyl-3-nitro-4-(p-tolyl)-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-2-amine

Conditions	Yield
With polyethylene glycol methacrylate-grafted tetraethylene glycol-bridged dicationic imidazolium based ionic liquid In neat (no solvent) at 80℃; Green chemistry;	96%
With toluene-4-sulfonic acid In ethanol at 80℃; for 3h;	91%

1H-benzimidazol-2-amine (934-32-7) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-ethoxybenzaldehyde (10031-82-0) → 4-(4-ethoxyphenyl)-N-methyl-3-nitro-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-2-amine

Conditions	Yield
With polyethylene glycol methacrylate-grafted tetraethylene glycol-bridged dicationic imidazolium based ionic liquid In neat (no solvent) at 80℃; Green chemistry;	96%

1H-benzimidazol-2-amine (934-32-7) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-methoxy-benzaldehyde (123-11-5) → 4-(4-methoxyphenyl)-N-methyl-3-nitro-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-2-amine

Conditions	Yield
With polyethylene glycol methacrylate-grafted tetraethylene glycol-bridged dicationic imidazolium based ionic liquid In neat (no solvent) at 80℃; for 0.333333h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Green chemistry;	96%
With toluene-4-sulfonic acid In ethanol at 80℃; for 3h;	91%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-chlorobenzaldehyde (104-88-1) + Benzoylacetonitrile (614-16-4) → 6-(methylamino)-4-(4-chlorophenyl)-5-nitro-2-phenyl-4H-pyran-3-carbonitrile

Conditions	Yield
Stage #1: 4-chlorobenzaldehyde; Benzoylacetonitrile With triethylamine In ethanol at 20℃; for 0.0833333 - 0.166667h; Stage #2: (E-)-N-methyl-1-(methylthio)-2-nitroethanamine In ethanol for 1.5h; Reflux;	95%
With triethylamine In ethanol for 1.5h; Reflux; regioselective reaction;	93%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-chlorobenzaldehyde (104-88-1) + 3-(1H-indol-3-yl)-3-oxo-propionitrile (20356-45-0) → 2-(1H-indol-3-yl)-6-(methylamino)-5-nitro-4-(4-chlorophenyl)-4H-pyran-3-carbonitrile (1463535-38-7)

Conditions	Yield
With triethylamine In ethanol for 1.5h; Solvent; Reagent/catalyst; Reflux; regioselective reaction;	95%
With indium(III) chloride for 0.0833333h; Microwave irradiation; Sealed tube; chemoselective reaction;	86%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + Benzoylacetonitrile (614-16-4) + 4-bromo-benzaldehyde (1122-91-4) → 6-(methylamino)-4-(4-bromophenyl)-5-nitro-2-phenyl-4H-pyran-3-carbonitrile (1463535-58-1)

Conditions	Yield
With triethylamine In ethanol for 1.5h; Reflux; regioselective reaction;	95%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + ethyl acetoacetate (141-97-9) + 4-bromo-benzaldehyde (1122-91-4) + phenylhydrazine (100-63-0) → 4-(4-bromophenyl)-N,3-dimethyl-5-nitro-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazol-6-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol Reflux;	95%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + ethyl acetoacetate (141-97-9) + 3,4,5-trimethoxy-benzaldehyde (86-81-7) + phenylhydrazine (100-63-0) → 4-(3,4,5-trimethoxyphenyl)-N,3-dimethyl-5-nitro-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazol-6-amine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol Reflux;	95%

1-prop-2-ynyl-1H-indole-2,3-dione (4290-87-3) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + edaravone (89-25-8) → C24H19N5O4 (1609627-39-5)

Conditions	Yield
In water at 80℃; Solvent; Green chemistry;	95%
With indium(III) chloride In ethanol for 7h; Reflux; Green chemistry; regioselective reaction;	90%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 2-methylphenyl aldehyde (529-20-4) + β-naphthol (135-19-3) → N-methyl-2-nitro-1-o-tolyl-1H-benzo[f]chromen-3-amine

Conditions	Yield
In ethanol; water at 60℃; for 0.633333h; Green chemistry;	95%

2,7-Dihydroxynaphthalene (582-17-2) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 3-methoxy-benzaldehyde (591-31-1) → 1-(3-methoxyphenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-9-ol

Conditions	Yield
In ethanol; water at 60℃; for 0.633333h; Green chemistry;	95%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-bromo-benzaldehyde (1122-91-4) + 2,3-naphthalenediol (92-44-4) → 1-(4-bromophenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-5-ol

Conditions	Yield
In ethanol; water at 60℃; for 0.666667h; Green chemistry;	95%

2,7-Dihydroxynaphthalene (582-17-2) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-bromo-benzaldehyde (1122-91-4) → 1-(4-bromophenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-9-ol

Conditions	Yield
In ethanol; water at 60℃; for 0.633333h; Green chemistry;	95%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-chlorobenzaldehyde (104-88-1) + β-naphthol (135-19-3) → 1-(4-chlorophenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

Conditions	Yield
In ethanol; water at 60℃; for 0.583333h; Green chemistry;	95%

2,7-Dihydroxynaphthalene (582-17-2) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-fluorobenzaldehyde (459-57-4) → 1-(4-fluorophenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-9-ol

Conditions	Yield
In ethanol; water at 60℃; for 0.616667h; Green chemistry;	95%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-ethoxybenzaldehyde (10031-82-0) + 2,3-naphthalenediol (92-44-4) → 1-(4-ethoxyphenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-5-ol

Conditions	Yield
In ethanol; water at 60℃; for 0.633333h; Green chemistry;	95%

2,7-Dihydroxynaphthalene (582-17-2) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-ethoxybenzaldehyde (10031-82-0) → 1-(4-ethoxyphenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-9-ol

Conditions	Yield
In ethanol; water at 60℃; for 0.6h; Green chemistry;	95%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 3-Chlorobenzaldehyde (587-04-2) + β-naphthol (135-19-3) → 1-(3-chlorophenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

Conditions	Yield
In ethanol; water at 60℃; for 0.633333h; Green chemistry;	95%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + (4-isopropylbenzaldehyde) (122-03-2) + β-naphthol (135-19-3) → 1-(4-isopropylphenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

Conditions	Yield
In ethanol; water at 60℃; for 0.633333h; Green chemistry;	95%

thiophene-2-carbaldehyde (98-03-3) + 2,7-Dihydroxynaphthalene (582-17-2) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) → 3-(methylamino)-2-nitro-1-(thiophen-2-yl)-1H-benzo[f]chromen-9-ol

Conditions	Yield
In ethanol; water at 60℃; for 0.666667h; Mechanism; Solvent; Temperature; Time; Green chemistry;	95%

1H-benzimidazol-2-amine (934-32-7) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-bromo-benzaldehyde (1122-91-4) → 4-(4-bromophenyl)-N-methyl-3-nitro-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-2-amine

Conditions	Yield
With polyethylene glycol methacrylate-grafted tetraethylene glycol-bridged dicationic imidazolium based ionic liquid In neat (no solvent) at 80℃; Green chemistry;	95%
With toluene-4-sulfonic acid In ethanol at 80℃; for 3h;	89%

1H-benzimidazol-2-amine (934-32-7) + (E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 4-fluorobenzaldehyde (459-57-4) → 4-(4-fluorophenyl)-N-methyl-3-nitro-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-2-amine

Conditions	Yield
With polyethylene glycol methacrylate-grafted tetraethylene glycol-bridged dicationic imidazolium based ionic liquid In neat (no solvent) at 80℃; Green chemistry;	95%
With toluene-4-sulfonic acid In ethanol at 80℃; for 4h;	90%

Upstream product

• 75-52-5 nitromethane 
• 18805-25-9 methyl carbonimidodithioic acid dimethyl ester 
• 74-89-5 methylamine 
• 13623-94-4 1,1-di(methylsulfanyl)-2-nitroethylene 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 593-51-1 methylamine hydrochloride 
• 61832-49-3 1-(n-methylsulfinyl)-1-(n-methylthio)-2-nitroethene 

Downstream Products

• 54252-45-8 N,N'-dimethyl-2-nitro-1,1-ethenediamine 
• 74-93-1 methylthiol 
• 66357-35-5 ranitidine 
• 76963-41-2 nizatidine 
• 1173429-51-0 N-[6-ethyl-4-(methylsulfanyl)-3-nitro-4H-2-chromenyl]-N-methylamine 
• 1173429-61-2 N-[7-(benzyloxy)-4-(methylsulfanyl)-3-nitro-4H-2-chromenyl]-N-methylamine 
• 1233536-62-3 C₁₄H₁₇N₃O₂ 
• 1233536-63-4 C₁₃H₁₅N₃O₂ 
• 120738-89-8 nitenpyram 
• 1407491-94-4 C₃₃H₃₆N₈O₆ 
• 1407491-79-5 C₃₂H₃₅N₉O₆ 
• 1407491-96-6 1-methyl-N-(1-methyl-5-{[(2-{[(E)-1-(methylamino)-2-nitroethenyl]amino}ethyl)amino]carbonyl}-1H-pyrrol-3-yl)-4-({4-[(E)-2-(3-quinolinyl)ethenyl]benzoyl}amino)-1H-pyrrole-2-carboxamide trifluoroacetate 
• 1425057-73-3 4-(2-fluorophenyl)-2-(methylamino)-3-nitropyrano[3,2-c]chromen-5(4H)-one 
• 1425057-70-0 2-(methylamino)-3-nitro-4-(p-tolyl)-4H,5H-pyrano[3,2-c]chromen-5-one 

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