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13623-94-4 Usage

Chemical Properties

yellow powder

Uses

Bis(methylthio)-2-nitroethylene is a synthetic intermediate as well as an Impurity of the ulcerostatic agent, Ranitidine (R120000).

Check Digit Verification of cas no

The CAS Registry Mumber 13623-94-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,6,2 and 3 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 13623-94:
(7*1)+(6*3)+(5*6)+(4*2)+(3*3)+(2*9)+(1*4)=94
94 % 10 = 4
So 13623-94-4 is a valid CAS Registry Number.
InChI:InChI=1/C4H7NO2S2/c1-8-4(9-2)3-5(6)7/h3H,1-2H3

13623-94-4 Well-known Company Product Price

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  • TCI America

  • (B1378)  1,1-Bis(methylthio)-2-nitroethylene  >98.0%(GC)

  • 13623-94-4

  • 25g

  • 675.00CNY

  • Detail
  • TCI America

  • (B1378)  1,1-Bis(methylthio)-2-nitroethylene  >98.0%(GC)

  • 13623-94-4

  • 100g

  • 2,180.00CNY

  • Detail
  • Alfa Aesar

  • (A11789)  1,1-Bis(methylthio)-2-nitroethylene, 99%   

  • 13623-94-4

  • 5g

  • 404.0CNY

  • Detail
  • Alfa Aesar

  • (A11789)  1,1-Bis(methylthio)-2-nitroethylene, 99%   

  • 13623-94-4

  • 25g

  • 1336.0CNY

  • Detail
  • Alfa Aesar

  • (A11789)  1,1-Bis(methylthio)-2-nitroethylene, 99%   

  • 13623-94-4

  • 100g

  • 4276.0CNY

  • Detail
  • Aldrich

  • (279706)  1,1-Bis(methylthio)-2-nitroethylene  95%

  • 13623-94-4

  • 279706-25G

  • 1,323.27CNY

  • Detail

13623-94-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,1-Bis(methylthio)-2-nitroethylene

1.2 Other means of identification

Product number -
Other names Nitroketene dimethyl mercaptal

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:13623-94-4 SDS

13623-94-4Synthetic route

dipotassium 2-nitroethylene-1,1-dithiolate
25963-52-4

dipotassium 2-nitroethylene-1,1-dithiolate

dimethyl sulfate
77-78-1

dimethyl sulfate

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

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

Conditions
ConditionsYield
In hexane; toluene at 0℃; for 2.5h;85%
In methanol at 20℃; for 2h;70%
In methanol at 20℃; for 2h;70%
In methanol at 20℃; for 2h;70%
In methanol; water
dipotassium 2-nitroethylene-1,1-dithiolate
25963-52-4

dipotassium 2-nitroethylene-1,1-dithiolate

methyl iodide
74-88-4

methyl iodide

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

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

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;77.5%
In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;77.5%
In acetonitrile at 20℃;60%
dimethyl sulfate
77-78-1

dimethyl sulfate

potassium; nitro-dithioacetate

potassium; nitro-dithioacetate

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

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

Conditions
ConditionsYield
With methanol In water for 2h; Ambient temperature;77%
carbon disulfide
75-15-0

carbon disulfide

nitromethane
75-52-5

nitromethane

methyl iodide
74-88-4

methyl iodide

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

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

Conditions
ConditionsYield
Stage #1: carbon disulfide; nitromethane at -15℃; for 0.25h; Inert atmosphere;
Stage #2: With potassium hydroxide In methanol at -10℃; for 2h; Inert atmosphere;
Stage #3: methyl iodide In methanol; water at 20℃; for 2h;
74%
Stage #1: carbon disulfide; nitromethane With potassium hydroxide In ethanol at 20℃; for 0.5h;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 1h;
72%
2-[(2-guanidinothiazol-4-yl)methylthio]ethylamine dihydrochloride
69014-10-4, 71916-64-8

2-[(2-guanidinothiazol-4-yl)methylthio]ethylamine dihydrochloride

A

1-{2-[(2-guanidino-4-thiazolyl)methylthio]ethylamino}-1-methylthio-2-nitroethene

1-{2-[(2-guanidino-4-thiazolyl)methylthio]ethylamino}-1-methylthio-2-nitroethene

B

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

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

Conditions
ConditionsYield
With sodium methylate In methanolA 65%
B n/a
nitro ketene dithioacetal
127476-96-4

nitro ketene dithioacetal

methyl iodide
74-88-4

methyl iodide

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

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

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
1,1-di(methylsulfanyl)-2-nitroethylene
13623-94-4

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

1,1-diamino-2-nitroethene
71090-35-2

1,1-diamino-2-nitroethene

Conditions
ConditionsYield
With ammonia In methanol at 50℃; for 18h;100%
With ammonia77%
With ammonia In methanol at 50℃; for 18h;76.9%
4-methoxy-aniline
104-94-9

4-methoxy-aniline

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

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

(E)-4-methoxy-N-[1-(methylthio)-2-nitroethenyl]benzenamine
143884-69-9

(E)-4-methoxy-N-[1-(methylthio)-2-nitroethenyl]benzenamine

Conditions
ConditionsYield
In ethanol at 110℃; for 1.5h; Microwave irradiation; Inert atmosphere;99%
In ethanol for 24h; Heating;91%
N-butylamine
109-73-9

N-butylamine

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

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

N,N'-dibutyl-2-nitroethene-1,1-diamine
1456912-96-1

N,N'-dibutyl-2-nitroethene-1,1-diamine

Conditions
ConditionsYield
In ethanol for 48h; Reflux;99%
5-hydroxypentylamine
2508-29-4

5-hydroxypentylamine

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

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

5,5'-((2-nitroethene-1,1-diyl)bis(azanediyl))bis(pentan-1-ol)
1456912-97-2

5,5'-((2-nitroethene-1,1-diyl)bis(azanediyl))bis(pentan-1-ol)

Conditions
ConditionsYield
In ethanol for 48h; Reflux;99%
ethylenediamine
107-15-3

ethylenediamine

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

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

2-(nitromethylene)imidazolidine
13623-98-8

2-(nitromethylene)imidazolidine

Conditions
ConditionsYield
In ethanol Reflux;98%
In ethanol at 110℃; for 0.333333h; Microwave irradiation;98%
In ethanol for 8h; Reflux;87%
4-fluoroaniline
371-40-4

4-fluoroaniline

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

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

4-fluoro-N-[1-(methylsulfanyl)-2-nitroethenyl]aniline
75178-04-0

4-fluoro-N-[1-(methylsulfanyl)-2-nitroethenyl]aniline

Conditions
ConditionsYield
In ethanol at 110℃; for 1.5h; Microwave irradiation; Inert atmosphere;98%
In ethanol for 10h; Heating;84%
In ethanol at 110℃; for 1.5h; Microwave irradiation;
In ethanol for 24h; Reflux;
In ethanol at 80℃; for 3h; Inert atmosphere;
cyclohexylamine
108-91-8

cyclohexylamine

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

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

N-[1-(methylthio)-2-nitroethenyl]cyclohexanamine
148342-52-3

N-[1-(methylthio)-2-nitroethenyl]cyclohexanamine

Conditions
ConditionsYield
In ethanol at 110℃; for 1.5h; Microwave irradiation; Inert atmosphere;98%
In ethanol for 18h; Heating;75%
for 24h; Heating;75%
Trimethylenediamine
109-76-2

Trimethylenediamine

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

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

1,2,3,4,5,6-hexahydro-2-(nitromethylidene)pyrimidine
59760-97-3

1,2,3,4,5,6-hexahydro-2-(nitromethylidene)pyrimidine

Conditions
ConditionsYield
In ethanol at 110℃; for 0.333333h; Microwave irradiation;98%
In ethanol at 80℃; for 4h;93%
In ethanol Reflux;85%
1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

5-nitroisatin
611-09-6

5-nitroisatin

ethylenediamine
107-15-3

ethylenediamine

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

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

4,5'-dinitro-2,3-dihydro-1H,6H-spiro[imidazo[1,2-a]indeno[2,1-e]pyridine-5,3′-indole]-2′,6(1′H)-dione

4,5'-dinitro-2,3-dihydro-1H,6H-spiro[imidazo[1,2-a]indeno[2,1-e]pyridine-5,3′-indole]-2′,6(1′H)-dione

Conditions
ConditionsYield
Stage #1: ethylenediamine; 1,1-di(methylsulfanyl)-2-nitroethylene In ethanol for 6h; Reflux; Green chemistry;
Stage #2: 1H-indene-1,3(2H)-dione; 5-nitroisatin With aluminum potassium sulfate dodecahydrate In ethanol at 60℃; for 1h; Green chemistry;
98%
4-bromo-aniline
106-40-1

4-bromo-aniline

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

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

4-bromo-N-[1-(methylthio)-2-nitroethenyl]benzenamine
168649-00-1

4-bromo-N-[1-(methylthio)-2-nitroethenyl]benzenamine

Conditions
ConditionsYield
In ethanol at 110℃; for 1.5h; Microwave irradiation; Inert atmosphere;97%
In ethanol at 110℃; for 1.5h; Microwave irradiation;
In ethanol for 24h; Reflux;
1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

ethylenediamine
107-15-3

ethylenediamine

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

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

4-nitro-5-(4-nitrophenyl)-2,3-dihydroimidazo[1,2-a]indeno[2,1-e]pyridine-6(5H)-one

4-nitro-5-(4-nitrophenyl)-2,3-dihydroimidazo[1,2-a]indeno[2,1-e]pyridine-6(5H)-one

Conditions
ConditionsYield
Stage #1: ethylenediamine; 1,1-di(methylsulfanyl)-2-nitroethylene In ethanol for 6h; Reflux;
Stage #2: 1H-indene-1,3(2H)-dione; 4-nitrobenzaldehdye With KAl(SO4)2·12H2O In ethanol for 1h; Reflux;
97%
1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

ethylenediamine
107-15-3

ethylenediamine

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

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

10b-hydroxy-4-nitro-5-(3-nitrophenyl)-2,3,5,5a-tetrahydro-1H-imidazo[1,2-a]indeno[2,1-e]pyridin-6(10bH)-one

10b-hydroxy-4-nitro-5-(3-nitrophenyl)-2,3,5,5a-tetrahydro-1H-imidazo[1,2-a]indeno[2,1-e]pyridin-6(10bH)-one

Conditions
ConditionsYield
Stage #1: ethylenediamine; 1,1-di(methylsulfanyl)-2-nitroethylene In ethanol for 6h; Reflux;
Stage #2: 1H-indene-1,3(2H)-dione; 3-nitro-benzaldehyde In ethanol for 1h; Reflux;
97%
1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

5-Bromo-1H-indole-2,3-dione
87-48-9

5-Bromo-1H-indole-2,3-dione

ethylenediamine
107-15-3

ethylenediamine

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

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

5'-bromo-4-nitro-2,3-dihydro-1H,6H-spiro[imidazo[1,2-a]indeno[2,1-e]pyridine-5,3′-indole]-2′,6(1′H)-dione

5'-bromo-4-nitro-2,3-dihydro-1H,6H-spiro[imidazo[1,2-a]indeno[2,1-e]pyridine-5,3′-indole]-2′,6(1′H)-dione

Conditions
ConditionsYield
Stage #1: ethylenediamine; 1,1-di(methylsulfanyl)-2-nitroethylene In ethanol for 6h; Reflux; Green chemistry;
Stage #2: 1H-indene-1,3(2H)-dione; 5-Bromo-1H-indole-2,3-dione With aluminum potassium sulfate dodecahydrate In ethanol at 60℃; for 1.16667h; Green chemistry;
97%
2-Hydroxy-1,4-naphthoquinone
83-72-7

2-Hydroxy-1,4-naphthoquinone

2,2-Dimethyl-1,3-diaminopropane
7328-91-8

2,2-Dimethyl-1,3-diaminopropane

(4-fluorophenyl)glyoxal
403-32-7

(4-fluorophenyl)glyoxal

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

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

2-[6-(4-fluoro-phenyl)-3,3-dimethyl-8-nitro-1,2,3,4-tetrahydro-pyrrolo[1,2-a]pyrimidin-7-yl]-3-hydroxy-[1,4]naphthoquinone

2-[6-(4-fluoro-phenyl)-3,3-dimethyl-8-nitro-1,2,3,4-tetrahydro-pyrrolo[1,2-a]pyrimidin-7-yl]-3-hydroxy-[1,4]naphthoquinone

Conditions
ConditionsYield
Stage #1: 2,2-Dimethyl-1,3-diaminopropane; 1,1-di(methylsulfanyl)-2-nitroethylene In ethanol; water for 4h; Reflux;
Stage #2: 2-hydroxynaphtho-1,4-quinone; (4-fluorophenyl)glyoxal In ethanol; water at 60℃; for 0.0833333h; regioselective reaction;
97%
2-Hydroxy-1,4-naphthoquinone
83-72-7

2-Hydroxy-1,4-naphthoquinone

(4-fluorophenyl)glyoxal
403-32-7

(4-fluorophenyl)glyoxal

1,4-diaminobutane
110-60-1

1,4-diaminobutane

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

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

2-[7-(4-fluoro-phenyl)-9-nitro-2,3,4,5-tetrahydro-1H-pyrrolo[1,2-a][1,3]diazepin-8-yl]-3-hydroxy-[1,4]naphthoquinone

2-[7-(4-fluoro-phenyl)-9-nitro-2,3,4,5-tetrahydro-1H-pyrrolo[1,2-a][1,3]diazepin-8-yl]-3-hydroxy-[1,4]naphthoquinone

Conditions
ConditionsYield
Stage #1: 1,4-diaminobutane; 1,1-di(methylsulfanyl)-2-nitroethylene In ethanol; water for 4h; Reflux;
Stage #2: 2-hydroxynaphtho-1,4-quinone; (4-fluorophenyl)glyoxal In ethanol; water at 60℃; for 0.0833333h; regioselective reaction;
97%
1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

ethylenediamine
107-15-3

ethylenediamine

4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

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

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

4-nitro-5-(4-cyanophenyl)-2,3-dihydroimidazo[1,2-a]indeno[2,1-e]pyridine-6(5H)-one

4-nitro-5-(4-cyanophenyl)-2,3-dihydroimidazo[1,2-a]indeno[2,1-e]pyridine-6(5H)-one

Conditions
ConditionsYield
Stage #1: ethylenediamine; 1,1-di(methylsulfanyl)-2-nitroethylene In ethanol for 6h; Reflux;
Stage #2: 1H-indene-1,3(2H)-dione; 4-cyanobenzaldehyde With KAl(SO4)2·12H2O In ethanol for 1.5h; Reflux;
96%
1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

ethylenediamine
107-15-3

ethylenediamine

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

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

4-nitro-5-(3-nitrophenyl)-2,3-dihydroimidazo[1,2-a]indeno[2,1-e]pyridine-6(5H)-one

4-nitro-5-(3-nitrophenyl)-2,3-dihydroimidazo[1,2-a]indeno[2,1-e]pyridine-6(5H)-one

Conditions
ConditionsYield
Stage #1: ethylenediamine; 1,1-di(methylsulfanyl)-2-nitroethylene In ethanol for 6h; Reflux;
Stage #2: 1H-indene-1,3(2H)-dione; 3-nitro-benzaldehyde With KAl(SO4)2·12H2O In ethanol for 1h; Reflux;
96%
1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

ethylenediamine
107-15-3

ethylenediamine

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

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

cis-10b-hydroxy-4-nitro-5-(4-nitrophenyl)-1,2,3,5,5a,10b-hexahydro-6H-imidazo[1,2-a]indeno[2,1-e]pyridin-6-one

cis-10b-hydroxy-4-nitro-5-(4-nitrophenyl)-1,2,3,5,5a,10b-hexahydro-6H-imidazo[1,2-a]indeno[2,1-e]pyridin-6-one

Conditions
ConditionsYield
Stage #1: ethylenediamine; 1,1-di(methylsulfanyl)-2-nitroethylene In ethanol for 6h; Reflux;
Stage #2: 1H-indene-1,3(2H)-dione; 4-nitrobenzaldehdye In ethanol for 1h; Reflux;
96%
Stage #1: ethylenediamine; 1,1-di(methylsulfanyl)-2-nitroethylene In ethanol for 6h; Reflux; Green chemistry;
Stage #2: 1H-indene-1,3(2H)-dione; 4-nitrobenzaldehdye In ethanol for 2h; Reflux; Green chemistry; diastereoselective reaction;
92%
benzylamine
100-46-9

benzylamine

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

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

N,N'-dibenzyl-2-nitroethylene-1,1-diamine
62390-82-3

N,N'-dibenzyl-2-nitroethylene-1,1-diamine

Conditions
ConditionsYield
In ethanol at 80℃; for 2h;95%
In ethanol for 48h; Reflux;92%
In ethanol
m-phenylenediamine
108-45-2

m-phenylenediamine

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

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

N,N'-bis-(1-methylsulfanyl-2-nitro-vinyl)-benzene-1,3-diamine

N,N'-bis-(1-methylsulfanyl-2-nitro-vinyl)-benzene-1,3-diamine

Conditions
ConditionsYield
In ethanol for 24h; Heating;95%
1,1-di(methylsulfanyl)-2-nitroethylene
13623-94-4

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

benzyl alcohol
100-51-6

benzyl alcohol

1-[1,1-di(benzyloxy)-2-nitroethoxy]methylbenzene

1-[1,1-di(benzyloxy)-2-nitroethoxy]methylbenzene

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0℃;95%
1,4-bis(4-methylphenyl)-2-butyne-1,4-dione
66864-60-6

1,4-bis(4-methylphenyl)-2-butyne-1,4-dione

1,4-diaminobutane
110-60-1

1,4-diaminobutane

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

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

2-[7-hydroxy-7-(4-methylphenyl)-9-nitro-2,3,4,5-tetrahydropyrrolo[1,2-a][1,3]diazepin-8-(7H)-yliden]-1-(4-methylphenyl)-1-ethanone
1262438-91-4

2-[7-hydroxy-7-(4-methylphenyl)-9-nitro-2,3,4,5-tetrahydropyrrolo[1,2-a][1,3]diazepin-8-(7H)-yliden]-1-(4-methylphenyl)-1-ethanone

Conditions
ConditionsYield
Stage #1: 1,4-diaminobutane; 1,1-di(methylsulfanyl)-2-nitroethylene In ethanol for 4h; Reflux;
Stage #2: 1,4-bis(4-methylphenyl)-2-butyne-1,4-dione In ethanol at 20℃; for 2h; diastereoselective reaction;
95%
1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Trimethylenediamine
109-76-2

Trimethylenediamine

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

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

cis-11b-hydroxy-5-nitro-6-(4-nitrophenyl)-2,3,4,6,6a,11b-hexahydroindeno[2',1':5,6]pyrido[1,2-a]pyrimidin-7(1H)-one

cis-11b-hydroxy-5-nitro-6-(4-nitrophenyl)-2,3,4,6,6a,11b-hexahydroindeno[2',1':5,6]pyrido[1,2-a]pyrimidin-7(1H)-one

Conditions
ConditionsYield
Stage #1: Trimethylenediamine; 1,1-di(methylsulfanyl)-2-nitroethylene In ethanol for 6h; Reflux; Green chemistry;
Stage #2: 1H-indene-1,3(2H)-dione; 4-nitrobenzaldehdye In ethanol for 2h; Reflux; Green chemistry; diastereoselective reaction;
95%
1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

5-nitroisatin
611-09-6

5-nitroisatin

Trimethylenediamine
109-76-2

Trimethylenediamine

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

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

5,5'-dinitro-1,2,3,4-tetrahydro-7H-spiro[indeno[2′,1′:5,6]pyrido[1,2-a]pyrimidine-6,3′-indole]-2′,7(1′H)-dione

5,5'-dinitro-1,2,3,4-tetrahydro-7H-spiro[indeno[2′,1′:5,6]pyrido[1,2-a]pyrimidine-6,3′-indole]-2′,7(1′H)-dione

Conditions
ConditionsYield
Stage #1: Trimethylenediamine; 1,1-di(methylsulfanyl)-2-nitroethylene In ethanol for 6h; Reflux; Green chemistry;
Stage #2: 1H-indene-1,3(2H)-dione; 5-nitroisatin With aluminum potassium sulfate dodecahydrate In ethanol at 60℃; for 1h; Green chemistry;
95%
1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

5-chloroindole 2,3-dione
17630-76-1

5-chloroindole 2,3-dione

ethylenediamine
107-15-3

ethylenediamine

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

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

5'-chloro-4-nitro-2,3-dihydro-1H,6H-spiro[imidazo[1,2-a]indeno[2,1-e]pyridine-5,3′-indole]-2′,6(1′H)-dione

5'-chloro-4-nitro-2,3-dihydro-1H,6H-spiro[imidazo[1,2-a]indeno[2,1-e]pyridine-5,3′-indole]-2′,6(1′H)-dione

Conditions
ConditionsYield
Stage #1: ethylenediamine; 1,1-di(methylsulfanyl)-2-nitroethylene In ethanol for 6h; Reflux; Green chemistry;
Stage #2: 1H-indene-1,3(2H)-dione; 5-chloroindole 2,3-dione With aluminum potassium sulfate dodecahydrate In ethanol at 60℃; for 1.25h; Green chemistry;
95%
2-Hydroxy-1,4-naphthoquinone
83-72-7

2-Hydroxy-1,4-naphthoquinone

(4-fluorophenyl)glyoxal
403-32-7

(4-fluorophenyl)glyoxal

1,2-diaminopropan
78-90-0, 10424-38-1

1,2-diaminopropan

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

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

2-[5-(4-fluoro-phenyl)-2-methyl-7-nitro-2,3-dihydro-1H-pyrrolo[1,2-a]imidazol-6-yl]-3-hydroxy-[1,4]naphthoquinone

2-[5-(4-fluoro-phenyl)-2-methyl-7-nitro-2,3-dihydro-1H-pyrrolo[1,2-a]imidazol-6-yl]-3-hydroxy-[1,4]naphthoquinone

Conditions
ConditionsYield
Stage #1: 1,2-diaminopropan; 1,1-di(methylsulfanyl)-2-nitroethylene In ethanol; water for 4h; Reflux;
Stage #2: 2-hydroxynaphtho-1,4-quinone; (4-fluorophenyl)glyoxal In ethanol; water at 60℃; for 0.0833333h; regioselective reaction;
95%
2-Hydroxy-1,4-naphthoquinone
83-72-7

2-Hydroxy-1,4-naphthoquinone

phenylglyoxal hydrate
1074-12-0

phenylglyoxal hydrate

1,4-diaminobutane
110-60-1

1,4-diaminobutane

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

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

2-hydroxy-3-(9-nitro-7-phenyl-2,3,4,5-tetrahydro-1H-pyrrolo[1,2-a][1,3]diazepin-8-yl)-[1,4]naphthoquinone

2-hydroxy-3-(9-nitro-7-phenyl-2,3,4,5-tetrahydro-1H-pyrrolo[1,2-a][1,3]diazepin-8-yl)-[1,4]naphthoquinone

Conditions
ConditionsYield
Stage #1: 1,4-diaminobutane; 1,1-di(methylsulfanyl)-2-nitroethylene In ethanol; water for 4h; Reflux;
Stage #2: 2-hydroxynaphtho-1,4-quinone; phenylglyoxal hydrate In ethanol; water at 60℃; for 0.25h; regioselective reaction;
95%
2-(2,4-dichloro-phenyl)-ethylamine
52516-13-9

2-(2,4-dichloro-phenyl)-ethylamine

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

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

1,1-bis((2,4-dichlorophenethyl)amino)-2-nitroethylene

1,1-bis((2,4-dichlorophenethyl)amino)-2-nitroethylene

Conditions
ConditionsYield
In ethanol for 12h; Reflux;95%
BARBITURIC ACID
67-52-7

BARBITURIC ACID

ethylamine
75-04-7

ethylamine

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

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

acenaphthene quinone
82-86-0

acenaphthene quinone

7'-(ethylamino)-6'-nitro-2H-spiro[acenaphthylene-1,5'-pyrano[2,3-d]pyrimidine]-2,2',4'(1'H,3'H)-trione

7'-(ethylamino)-6'-nitro-2H-spiro[acenaphthylene-1,5'-pyrano[2,3-d]pyrimidine]-2,2',4'(1'H,3'H)-trione

Conditions
ConditionsYield
In ethanol for 8.5h; Reflux; chemoselective reaction;95%
1H-indene-1,3(2H)-dione
606-23-5

1H-indene-1,3(2H)-dione

2-mercaptoethylamine hydrochloride
156-57-0

2-mercaptoethylamine hydrochloride

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

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

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

10b-hydroxy-4-nitro-5-(4-nitro-phenyl)-1,2,5a,10b-tetrahydro-5H-3-thia-10c-aza-cyclopenta[c]fluoren-6-one

10b-hydroxy-4-nitro-5-(4-nitro-phenyl)-1,2,5a,10b-tetrahydro-5H-3-thia-10c-aza-cyclopenta[c]fluoren-6-one

Conditions
ConditionsYield
Stage #1: 2-mercaptoethylamine hydrochloride; 1,1-di(methylsulfanyl)-2-nitroethylene With triethylamine In ethanol; water for 4h; Reflux;
Stage #2: 1H-indene-1,3(2H)-dione; 4-nitrobenzaldehdye In ethanol; water at 80℃; for 0.0333333h; diastereoselective reaction;
95%

13623-94-4Relevant articles and documents

Nitroketene dithioacetal chemistry. Part 2: Synthesis of novel 4-(alkylsulfanyl)-2-[1-nitromethylidene]-1,3-dithioles from the dipotassium salt of 2-nitro-1,1-ethylenedithiol

Rao, H. Surya Prakash,Sakthikumar,Vanitha,Kumar, S. Siva

, p. 4701 - 4704 (2003)

The reaction of the dipotassium salt of 2-nitro-1,1-ethylenedithiol with long chain alkyl halides in acetonitrile medium furnished the novel heterocyclic, 4-(alkylsulfanyl)-2-[1-nitromethylidene]-1,3-dithioles.

Design, synthesis and biological evaluation of novel inosine 5′-monophosphate dehydrogenase (IMPDH) inhibitors

Dunkern, Torsten,Chavan, Sunil,Bankar, Digambar,Patil, Anuja,Kulkarni, Pritee,Kharkar, Prashant S.,Prabhu, Arati,Goebel, Heike,Rolser, Edith,Burckhard-Boer, Waltraud,Arumugam, Premkumar,Makhija, Mahindra T.

, p. 408 - 419 (2014/06/09)

This study is based on our attempts to further explore the structure-activity relationship (SAR) of VX-148 (3) in an attempt to identify inosine 5′-mono-phosphate dehydrogenase (IMPDH) inhibitors superior to mycophenolic acid. A five-point pharmacophore developed using structurally diverse, known IMPDH inhibitors guided further design of novel analogs of 3. Several conventional as well as novel medicinal chemistry strategies were tried. The combined structure- and ligand-based approaches culminated in a few analogs with either retained or slightly higher potency. The compounds which retained the potency were also checked for their ability to inhibit human peripheral blood mononuclear cells proliferation. This study illuminates the stringent structural requirements and strict SAR for IMPDH II inhibition.

Heterocyclic Sulfonamide Derivatives

-

Page/Page column 16, (2011/08/08)

The present invention relates to compounds of Formula I where R1a, R1b, X, R2a, R2b, W, R3, R4, and R5 are as defined herein as well as pharmaceutically acceptable salts thereof. The compounds have been shown to act as MEK inhibitors which may be useful in the treatment of hyperproliferative diseases, like cancer and inflammation.

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