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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.

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  • 61832-41-5 Structure
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    1. Product Name: N-Methyl-1-(methylthio)-2-nitroethylen-1-amine
    2. 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
    3. CAS NO:61832-41-5
    4. Molecular Formula: C4H8N2O2S
    5. Molecular Weight: 149.19
    6. EINECS: 263-266-9
    7. 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
    8. Mol File: 61832-41-5.mol
  • Chemical Properties

    1. Melting Point: 112-118 °C(lit.)
    2. Boiling Point: 236.5 °C at 760 mmHg
    3. Flash Point: 96.8 °C
    4. Appearance: /
    5. Density: 1.199 g/cm3
    6. Vapor Pressure: 0.168mmHg at 25°C
    7. Refractive Index: 1.533
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: 0.86±0.70(Predicted)
    11. BRN: 2828017
    12. CAS DataBase Reference: N-Methyl-1-(methylthio)-2-nitroethylen-1-amine(CAS DataBase Reference)
    13. NIST Chemistry Reference: N-Methyl-1-(methylthio)-2-nitroethylen-1-amine(61832-41-5)
    14. EPA Substance Registry System: N-Methyl-1-(methylthio)-2-nitroethylen-1-amine(61832-41-5)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36-37/39
    4. RIDADR: UN 3335
    5. WGK Germany: 3
    6. RTECS:
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 61832-41-5(Hazardous Substances Data)

61832-41-5 Usage

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.

Check Digit Verification of cas no

The CAS Registry Mumber 61832-41-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,1,8,3 and 2 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 61832-41:
(7*6)+(6*1)+(5*8)+(4*3)+(3*2)+(2*4)+(1*1)=115
115 % 10 = 5
So 61832-41-5 is a valid CAS Registry Number.
InChI:InChI=1/C4H8N2O2S/c1-5-4(9-2)3-6(7)8/h3H2,1-2H3/b5-4-

61832-41-5 Well-known Company Product Price

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  • Alfa Aesar

  • (B22608)  1-Methylthio-1-methylamino-2-nitroethylene, 97%   

  • 61832-41-5

  • 10g

  • 239.0CNY

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  • Alfa Aesar

  • (B22608)  1-Methylthio-1-methylamino-2-nitroethylene, 97%   

  • 61832-41-5

  • 50g

  • 660.0CNY

  • Detail
  • Alfa Aesar

  • (B22608)  1-Methylthio-1-methylamino-2-nitroethylene, 97%   

  • 61832-41-5

  • 250g

  • 2794.0CNY

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  • Aldrich

  • (417459)  N-Methyl-1-(methylthio)-2-nitroethenamine  98%

  • 61832-41-5

  • 417459-25G

  • 391.95CNY

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61832-41-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name N-Methyl-1-(methylthio)-2-nitroethylen-1-amine

1.2 Other means of identification

Product number -
Other names NMSM

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:61832-41-5 SDS

61832-41-5Synthetic route

methylamine
74-89-5

methylamine

1,1-di(methylsulfanyl)-2-nitroethylene
13623-94-4

1,1-di(methylsulfanyl)-2-nitroethylene

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

Conditions
ConditionsYield
In ethanol for 5h; Reflux;75%
methylamine hydrochloride
593-51-1

methylamine hydrochloride

1,1-di(methylsulfanyl)-2-nitroethylene
13623-94-4

1,1-di(methylsulfanyl)-2-nitroethylene

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

Conditions
ConditionsYield
With potassium carbonate In dichloromethane
1-(n-methylsulfinyl)-1-(n-methylthio)-2-nitroethene
61832-49-3

1-(n-methylsulfinyl)-1-(n-methylthio)-2-nitroethene

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

Conditions
ConditionsYield
With methylamine In methanol
(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

benzaldehyde
100-52-7

benzaldehyde

N,1-dimethyl-6-(methylthio)-3,5-dinitro-4-phenyl-1,4-dihydropyridin-2-amine
1620024-38-5

N,1-dimethyl-6-(methylthio)-3,5-dinitro-4-phenyl-1,4-dihydropyridin-2-amine

Conditions
ConditionsYield
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

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

3-methoxy-2-hydroxybenzaldehyde
148-53-8

3-methoxy-2-hydroxybenzaldehyde

N-[8-methoxy-4-(methylsulfanyl)-3-nitro-4H-2-chromenyl]-N-methylamine
1173429-63-4

N-[8-methoxy-4-(methylsulfanyl)-3-nitro-4H-2-chromenyl]-N-methylamine

Conditions
ConditionsYield
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

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

ethyl acetoacetate
141-97-9

ethyl acetoacetate

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

phenylhydrazine
100-63-0

phenylhydrazine

4-(2-methylphenyl)-N,3-dimethyl-5-nitro-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazol-6-amine

4-(2-methylphenyl)-N,3-dimethyl-5-nitro-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazol-6-amine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In ethanol Reflux;96%
(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

β-naphthol
135-19-3

β-naphthol

1-(3,4,5-trimethoxyphenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

1-(3,4,5-trimethoxyphenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

Conditions
ConditionsYield
In ethanol; water at 60℃; for 0.583333h; Green chemistry;96%
(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

β-naphthol
135-19-3

β-naphthol

1-(4-methoxyphenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

1-(4-methoxyphenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

Conditions
ConditionsYield
In ethanol; water at 60℃; for 0.6h; Green chemistry;96%
2,7-Dihydroxynaphthalene
582-17-2

2,7-Dihydroxynaphthalene

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

1-(4-methoxyphenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-9-ol

1-(4-methoxyphenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-9-ol

Conditions
ConditionsYield
In ethanol; water at 60℃; for 0.583333h; Green chemistry;96%
(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

4-ethoxybenzaldehyde
10031-82-0

4-ethoxybenzaldehyde

β-naphthol
135-19-3

β-naphthol

1-(4-ethoxyphenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

1-(4-ethoxyphenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

Conditions
ConditionsYield
In ethanol; water at 60℃; for 0.583333h; Green chemistry;96%
piperonal
120-57-0

piperonal

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

β-naphthol
135-19-3

β-naphthol

1-(benzo[d][1,3]dioxol-6-yl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

1-(benzo[d][1,3]dioxol-6-yl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

Conditions
ConditionsYield
In ethanol; water at 60℃; for 0.616667h; Green chemistry;96%
1H-benzimidazol-2-amine
934-32-7

1H-benzimidazol-2-amine

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

N-methyl-3-nitro-4-(p-tolyl)-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-2-amine

N-methyl-3-nitro-4-(p-tolyl)-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-2-amine

Conditions
ConditionsYield
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

1H-benzimidazol-2-amine

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

4-ethoxybenzaldehyde
10031-82-0

4-ethoxybenzaldehyde

4-(4-ethoxyphenyl)-N-methyl-3-nitro-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-2-amine

4-(4-ethoxyphenyl)-N-methyl-3-nitro-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-2-amine

Conditions
ConditionsYield
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

1H-benzimidazol-2-amine

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

4-(4-methoxyphenyl)-N-methyl-3-nitro-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-2-amine

4-(4-methoxyphenyl)-N-methyl-3-nitro-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-2-amine

Conditions
ConditionsYield
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

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Benzoylacetonitrile
614-16-4

Benzoylacetonitrile

6-(methylamino)-4-(4-chlorophenyl)-5-nitro-2-phenyl-4H-pyran-3-carbonitrile

6-(methylamino)-4-(4-chlorophenyl)-5-nitro-2-phenyl-4H-pyran-3-carbonitrile

Conditions
ConditionsYield
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

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

3-(1H-indol-3-yl)-3-oxo-propionitrile
20356-45-0

3-(1H-indol-3-yl)-3-oxo-propionitrile

2-(1H-indol-3-yl)-6-(methylamino)-5-nitro-4-(4-chlorophenyl)-4H-pyran-3-carbonitrile
1463535-38-7

2-(1H-indol-3-yl)-6-(methylamino)-5-nitro-4-(4-chlorophenyl)-4H-pyran-3-carbonitrile

Conditions
ConditionsYield
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

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

Benzoylacetonitrile
614-16-4

Benzoylacetonitrile

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

6-(methylamino)-4-(4-bromophenyl)-5-nitro-2-phenyl-4H-pyran-3-carbonitrile
1463535-58-1

6-(methylamino)-4-(4-bromophenyl)-5-nitro-2-phenyl-4H-pyran-3-carbonitrile

Conditions
ConditionsYield
With triethylamine In ethanol for 1.5h; Reflux; regioselective reaction;95%
(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

ethyl acetoacetate
141-97-9

ethyl acetoacetate

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

phenylhydrazine
100-63-0

phenylhydrazine

4-(4-bromophenyl)-N,3-dimethyl-5-nitro-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazol-6-amine

4-(4-bromophenyl)-N,3-dimethyl-5-nitro-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazol-6-amine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In ethanol Reflux;95%
(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

ethyl acetoacetate
141-97-9

ethyl acetoacetate

3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

phenylhydrazine
100-63-0

phenylhydrazine

4-(3,4,5-trimethoxyphenyl)-N,3-dimethyl-5-nitro-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazol-6-amine

4-(3,4,5-trimethoxyphenyl)-N,3-dimethyl-5-nitro-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazol-6-amine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In ethanol Reflux;95%
1-prop-2-ynyl-1H-indole-2,3-dione
4290-87-3

1-prop-2-ynyl-1H-indole-2,3-dione

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

edaravone
89-25-8

edaravone

C24H19N5O4
1609627-39-5

C24H19N5O4

Conditions
ConditionsYield
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

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

β-naphthol
135-19-3

β-naphthol

N-methyl-2-nitro-1-o-tolyl-1H-benzo[f]chromen-3-amine

N-methyl-2-nitro-1-o-tolyl-1H-benzo[f]chromen-3-amine

Conditions
ConditionsYield
In ethanol; water at 60℃; for 0.633333h; Green chemistry;95%
2,7-Dihydroxynaphthalene
582-17-2

2,7-Dihydroxynaphthalene

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

1-(3-methoxyphenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-9-ol

1-(3-methoxyphenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-9-ol

Conditions
ConditionsYield
In ethanol; water at 60℃; for 0.633333h; Green chemistry;95%
(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

2,3-naphthalenediol
92-44-4

2,3-naphthalenediol

1-(4-bromophenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-5-ol

1-(4-bromophenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-5-ol

Conditions
ConditionsYield
In ethanol; water at 60℃; for 0.666667h; Green chemistry;95%
2,7-Dihydroxynaphthalene
582-17-2

2,7-Dihydroxynaphthalene

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

1-(4-bromophenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-9-ol

1-(4-bromophenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-9-ol

Conditions
ConditionsYield
In ethanol; water at 60℃; for 0.633333h; Green chemistry;95%
(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

β-naphthol
135-19-3

β-naphthol

1-(4-chlorophenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

1-(4-chlorophenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

Conditions
ConditionsYield
In ethanol; water at 60℃; for 0.583333h; Green chemistry;95%
2,7-Dihydroxynaphthalene
582-17-2

2,7-Dihydroxynaphthalene

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

1-(4-fluorophenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-9-ol

1-(4-fluorophenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-9-ol

Conditions
ConditionsYield
In ethanol; water at 60℃; for 0.616667h; Green chemistry;95%
(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

4-ethoxybenzaldehyde
10031-82-0

4-ethoxybenzaldehyde

2,3-naphthalenediol
92-44-4

2,3-naphthalenediol

1-(4-ethoxyphenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-5-ol

1-(4-ethoxyphenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-5-ol

Conditions
ConditionsYield
In ethanol; water at 60℃; for 0.633333h; Green chemistry;95%
2,7-Dihydroxynaphthalene
582-17-2

2,7-Dihydroxynaphthalene

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

4-ethoxybenzaldehyde
10031-82-0

4-ethoxybenzaldehyde

1-(4-ethoxyphenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-9-ol

1-(4-ethoxyphenyl)-3-(methylamino)-2-nitro-1H-benzo[f]chromen-9-ol

Conditions
ConditionsYield
In ethanol; water at 60℃; for 0.6h; Green chemistry;95%
(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

β-naphthol
135-19-3

β-naphthol

1-(3-chlorophenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

1-(3-chlorophenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

Conditions
ConditionsYield
In ethanol; water at 60℃; for 0.633333h; Green chemistry;95%
(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

β-naphthol
135-19-3

β-naphthol

1-(4-isopropylphenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

1-(4-isopropylphenyl)-N-methyl-2-nitro-1H-benzo[f]chromen-3-amine

Conditions
ConditionsYield
In ethanol; water at 60℃; for 0.633333h; Green chemistry;95%
thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

2,7-Dihydroxynaphthalene
582-17-2

2,7-Dihydroxynaphthalene

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

3-(methylamino)-2-nitro-1-(thiophen-2-yl)-1H-benzo[f]chromen-9-ol

3-(methylamino)-2-nitro-1-(thiophen-2-yl)-1H-benzo[f]chromen-9-ol

Conditions
ConditionsYield
In ethanol; water at 60℃; for 0.666667h; Mechanism; Solvent; Temperature; Time; Green chemistry;95%
1H-benzimidazol-2-amine
934-32-7

1H-benzimidazol-2-amine

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

4-(4-bromophenyl)-N-methyl-3-nitro-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-2-amine

4-(4-bromophenyl)-N-methyl-3-nitro-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-2-amine

Conditions
ConditionsYield
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

1H-benzimidazol-2-amine

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

4-(4-fluorophenyl)-N-methyl-3-nitro-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-2-amine

4-(4-fluorophenyl)-N-methyl-3-nitro-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-2-amine

Conditions
ConditionsYield
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%

61832-41-5Relevant articles and documents

A simple and environmentally benign synthesis of novel spiro[indoline-3,5′-pyrano[2,3-d]pyrimidine] derivatives in water

Ghadiri, Sakineh,Bayat, Mohammad,Hosseini, Fahimeh Sadat

, p. 1079 - 1084 (2019/03/14)

Abstract: A green, convenient, and efficient one-pot synthesis of a new class of spiro[indolinepyranopyrimidine] derivatives was achieved in good yields by the multi-component reaction of N-alkyl-1-(methylthio)-2-nitroethenamine derived from the addition

Rapid and catalyst free synthesis of new bis(benzo[: G] chromene) and bis(pyrano[3,2- c] chromene) derivatives and optimization of reaction conditions using response surface methodology

Hosseini, Fahimeh Sadat,Bayat, Mohammad,Afsharnezhad, Milad

, p. 39466 - 39474 (2019/12/15)

4,4′-(1,4-phenylene)bis(2-(alkylamino)-3-nitro-4H-benzo[g]chromene-5,10-dione) and 4,4′-(1,4-phenylene)bis(2-(alkylamino)-3-nitropyrano[3,2-c]chromen-5(4H)-one) derivatives are synthesized by a one-pot, multi-component reaction of N-alkyl-1-(methylthio)-2

Synthesis of Spiro[indoline-3,4′-pyrano[3,2-c]chromene]diones

Ghadiri, Sakineh,Bayat, Mohammad,Hosseini, Fahimeh Sadat

, p. 2693 - 2697 (2018/10/20)

A new series of isatin-based spiro-fused derivatives were prepared, via three-component reaction of N-alkyl-1-(methylthio)-2-nitroethenamine derived from the addition of various amines to nitroketene dithioacetal with isatin derivatives and 4-hydroxycouma

Critical Influence of 5-Hydroxymethylfurfural Aging and Decomposition on the Utility of Biomass Conversion in Organic Synthesis

Galkin, Konstantin I.,Krivodaeva, Elena A.,Romashov, Leonid V.,Zalesskiy, Sergey S.,Kachala, Vadim V.,Burykina, Julia V.,Ananikov, Valentine P.

supporting information, p. 8338 - 8342 (2016/07/19)

Spectral studies revealed the presence of a specific arrangement of 5-hydroxymethylfurfural (5-HMF) molecules in solution as a result of a hydrogen–bonding network, and this arrangement readily facilitates the aging of 5-HMF. Deterioration of the quality of this platform chemical limits its practical applications, especially in synthesis/pharma areas. The model drug Ranitidine (Zantac) was synthesized with only 15 % yield starting from 5-HMF which was isolated and stored as an oil after a biomass conversion process. In contrast, a much higher yield of 65 % was obtained by using 5-HMF isolated in crystalline state from an optimized biomass conversion process. The molecular mechanisms responsible for 5-HMF decomposition in solution were established by NMR and ESI-MS studies. A highly selective synthesis of a 5-HMF derivative from glucose was achieved using a protecting group at O(6) position.

A 1 - methylamino -1 - methylthio -2 - nitroethylene method for the preparation of

-

Paragraph 0073; 0074; 0075; 0076; 0077, (2016/10/09)

The invention relates to the field of chemical synthesis, and especially relates to a preparation method for 1-methylamino-1-methylthio-2-nitroethylene. The preparation method comprises: in the presence of a solvent, taking nitromethane, carbon disulfide and potassium hydroxide to perform a condensation reaction, so as to obtain a compound of a formula II; taking the compound of the formula II and methylamine to perform amination reaction, so as to obtain a compound of a formula III and hydrosulfide ion which is reacted with an acid for generating hydrogen sulfide; taking the compound of the formula III, a methylation reagent and an alkali to perform a methylation reaction, so as to obtain 1-methylamino-1-methylthio-2-nitroethylene crude product; and refining the crude product, so as to obtain 1-methylamino-1-methylthio-2-nitroethylene. The provided preparation method for 1-methylamino-1-methylthio-2-nitroethylene eliminates generation of a main gas pollution source methyl mercaptan, guarantees product quality, substantially reduces usage amount of the raw materials, shortens the reaction time and improves the product yield.

POLYFLUORINATED COMPOUNDS ACTING AS BRUTON TYROSINE KINASE INHIBITORS

-

Paragraph 0633; 0634, (2016/08/17)

Described herein is a novel series of multi-fluoro-substituted pyrazolopyrimidine compounds or salts thereof. These compounds are Bruton's tyrosine kinase (BTK) inhibitors. These compounds may possess better BTK inhibition selectivity and pharmacokinetic properties. Disclosed herein are the synthesis methods of these compounds. Disclosed herein are novel synthesis methods of the multi-fluoro-substituted benzophenone and substituted phenoxy benzene. Also disclosed are pharmaceutical compositions comprising the BTK inhibitors described herein. The present invention also relates to pharmaceutical formulations comprising the compounds described herein as active ingredients. The present invention also includes the therapeutic methods by administering the BTK inhibitors and their formulations to treat and inhibit autoimmune disease, hypersensitivity disease, inflammatory diseases and cancer.

An efficient synthesis of N-substituted 3-nitrothiophen-2-amines

Kumar, Sundaravel Vivek,Muthusubramanian, Shanmugam,Menéndez, J. Carlos,Perumal, Subbu

supporting information, p. 1707 - 1712 (2016/04/10)

A novel protocol for the synthesis of 3-nitro-N-aryl/alkylthiophen-2-amines in good yields from the reaction of α-nitroketene N,S-aryl/alkylaminoacetals and 1,4-dithiane-2,5-diol in the presence of K2CO3 in refluxing ethanol is descr

Design, synthesis, and particular biological behaviors of chain-opening nitromethylene neonicotinoids with cis configuration

Lu, Siyuan,Shao, Xusheng,Li, Zhong,Xu, Zhiping,Zhao, Shishuai,Wu, Yinli,Xu, Xiaoyong

experimental part, p. 322 - 330 (2012/04/04)

On the basis of the structure of heterocyclic-fused cis configuration derivatives and chain-opening neonicotinoids, two series of novel chain-opening tetrahydropyridine analogues were designed and synthesized. The preliminary bioassay tests were determined on cowpea aphid (Aphis craccivora) and armyworm (Pseudaletia separata Walker). The results showed that some of the target compounds exhibited repellent effects, whereas others showed good insecticidal activities.

Inhibitors for human glutaminyl cyclase by structure based design and bioisosteric replacement

Buchholz, Mirko,Hamann, Antje,Aust, Susanne,Brandt, Wolfgang,B?hme, Livia,Hoffmann, Torsten,Schilling, Stephan,Demuth, Hans-Ulrich,Heiser, Ulrich

experimental part, p. 7069 - 7080 (2010/05/02)

The inhibition of human glutaminyl cyclase (hQC) has come into focus as a new potential approach for the treatment of Alzheimer's disease. The hallmark of this principle is the prevention of the formation of Aβ 3,11(pE)-40,42, as these Aβ-speci

Synthesis and analgesic activity evaluation of some agmatine derivatives

He, Hongxia,Liu, Mengjia,Zheng, Zhibing,Liu, Ying,Xiao, Junhai,Su, Ruibin,Hu, Chun,Li, Jin,Li, Song

, p. 393 - 402 (2007/10/03)

A series of N,N′-disubstituted-2-nitroethene-1,1-diamine and N,N′-disubstituted-N″-cyanoguanidine derivatives were prepared and evaluated for in vivo analgesic activity. The blood brain barrier (BBB) VolSurf model was used to predict the BBB permeation profiles of our synthesized compounds. Some compounds show both remarkable analgesic activity and good BBB permeation profiles, and these compounds might be developed for treatment of opioid tolerance and dependence.

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