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25717-80-0

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25717-80-0 Usage

Chemical Properties

White to Off-White Solid

Originator

Corvasal,Hoechst

Uses

Different sources of media describe the Uses of 25717-80-0 differently. You can refer to the following data:
1. Molsidomine is an antianginal agent. Molsidomine is an effective therapeutic agents in the treatment of angina pectoris. Molsidomine is a sydnonimine derivative that acts as a heterocyclic direct nitr ic oxide donor.
2. Molsidomine is an antianginal agent. Molsidomine is an effective therapeutic agents in the treatment of angina pectoris. Molsidomine is a sydnonimine derivative that acts as a heterocyclic direct nitric oxide donor.

Manufacturing Process

1.6 parts by volume of ethyl chloroformate is stirred dropwise into a suspension of 1.0 part by weight of 3-morpholinosydnonimine hydrochloride in 5 parts by volume of pyridine, and the mixture is agitated for a while to allow reaction to take place. Pyridine is removed from the reaction mixture by evaporation, and the residue is dissolved in a small amount of water and extracted with chloroform several times. The extract is dehydrated by adding anhydrous magnesium sulfate and subjected to filtration. Chloroform is removed from the filtrate by distillation, crude crystals being obtained. Recrystallization of the crude crystals from toluene gives 0.6 part by weight of 3-morpholino-N-carboethoxysydnonimine having a melting point of 140°- 141°C. Yield 51%.

Brand name

Corvaton (Hoechst-Roussel).

Therapeutic Function

Coronary vasodilator

Check Digit Verification of cas no

The CAS Registry Mumber 25717-80-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,5,7,1 and 7 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 25717-80:
(7*2)+(6*5)+(5*7)+(4*1)+(3*7)+(2*8)+(1*0)=120
120 % 10 = 0
So 25717-80-0 is a valid CAS Registry Number.
InChI:InChI=1/C9H14N4O4/c1-2-16-9(14)10-8-7-13(11-17-8)12-3-5-15-6-4-12/h7H,2-6H2,1H3

25717-80-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (M2524)  Molsidomine  >98.0%(HPLC)(T)

  • 25717-80-0

  • 1g

  • 430.00CNY

  • Detail
  • TCI America

  • (M2524)  Molsidomine  >98.0%(HPLC)(T)

  • 25717-80-0

  • 5g

  • 1,390.00CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000821)  Molsidomine  European Pharmacopoeia (EP) Reference Standard

  • 25717-80-0

  • Y0000821

  • 1,880.19CNY

  • Detail
  • Sigma

  • (M2901)  Molsidomine  

  • 25717-80-0

  • M2901-500MG

  • 746.46CNY

  • Detail
  • Sigma

  • (M2901)  Molsidomine  

  • 25717-80-0

  • M2901-5G

  • 4,443.66CNY

  • Detail

25717-80-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Molsidomine

1.2 Other means of identification

Product number -
Other names (1E)-1-ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate

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:25717-80-0 SDS

25717-80-0Synthetic route

4-lithiomolsidomine

4-lithiomolsidomine

molsidomine
25717-80-0

molsidomine

Conditions
ConditionsYield
With water100%
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

Linsidomine hydrochloride
16142-27-1

Linsidomine hydrochloride

molsidomine
25717-80-0

molsidomine

Conditions
ConditionsYield
With sodium hydrogencarbonate
molsidomine
25717-80-0

molsidomine

4-lithiomolsidomine

4-lithiomolsidomine

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran; tetrahydrofuran-d8 Inert atmosphere;100%
sulfur
10544-50-0

sulfur

molsidomine
25717-80-0

molsidomine

mercury dichloride

mercury dichloride

bis((6-ethoxycarbonyl-3-morpholinyl-sydnone imine-4-yl)thio)mercury(II)

bis((6-ethoxycarbonyl-3-morpholinyl-sydnone imine-4-yl)thio)mercury(II)

Conditions
ConditionsYield
Stage #1: molsidomine With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: sulfur In tetrahydrofuran at 0℃; Inert atmosphere;
Stage #3: mercury dichloride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
88%
triphenylborane
960-71-4

triphenylborane

molsidomine
25717-80-0

molsidomine

(5-ethylcarbamate-3-morpholinyl-1,2,3-oxadiazolium-4-yl)triphenylborate

(5-ethylcarbamate-3-morpholinyl-1,2,3-oxadiazolium-4-yl)triphenylborate

Conditions
ConditionsYield
Stage #1: molsidomine With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: triphenylborane In tetrahydrofuran at -10 - 20℃; for 4h; Inert atmosphere;
87%
molsidomine
25717-80-0

molsidomine

methyl iodide
74-88-4

methyl iodide

6-ethoxycarbonyl-4-methylthio-3-morpholinyl sydnone imine

6-ethoxycarbonyl-4-methylthio-3-morpholinyl sydnone imine

Conditions
ConditionsYield
Stage #1: molsidomine With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With sulfur In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
Stage #3: methyl iodide In tetrahydrofuran at 0 - 20℃; for 2.5h; Inert atmosphere;
85%
molsidomine
25717-80-0

molsidomine

mercury dichloride

mercury dichloride

bis(6-ethoxycarbonyl-3-morpholinyl-sydnone imine-4-yl)mercury(II)

bis(6-ethoxycarbonyl-3-morpholinyl-sydnone imine-4-yl)mercury(II)

Conditions
ConditionsYield
Stage #1: molsidomine With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: mercury dichloride In tetrahydrofuran at 0 - 20℃; for 3.5h; Inert atmosphere;
78%
molsidomine
25717-80-0

molsidomine

ethyl-N-(1-morpholinyl-1-thioxo-ethan-2-one)carbamate

ethyl-N-(1-morpholinyl-1-thioxo-ethan-2-one)carbamate

Conditions
ConditionsYield
Stage #1: molsidomine With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With sulfur In tetrahydrofuran at 0℃; for 2.5h; Inert atmosphere;
Stage #3: With water In tetrahydrofuran Inert atmosphere;
63%
sulfur
10544-50-0

sulfur

(triphenylphosphine)gold(I) chloride
14243-64-2

(triphenylphosphine)gold(I) chloride

molsidomine
25717-80-0

molsidomine

((6-ethoxycarbonyl-3-morpholinyl-sydnone imine-4-yl)thio)(triphenylphosphine)gold(I)

((6-ethoxycarbonyl-3-morpholinyl-sydnone imine-4-yl)thio)(triphenylphosphine)gold(I)

Conditions
ConditionsYield
Stage #1: molsidomine With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: sulfur In tetrahydrofuran at 0℃; Inert atmosphere;
Stage #3: (triphenylphosphine)gold(I) chloride In tetrahydrofuran at 0 - 20℃; for 3.5h; Inert atmosphere;
36%
molsidomine
25717-80-0

molsidomine

morpholine
110-91-8

morpholine

Conditions
ConditionsYield
In methanol for 0.166667h; Product distribution; Kinetics; Irradiation; var. of solvent, also additives;
molsidomine
25717-80-0

molsidomine

peracetylated β-cyclodextrin
23739-88-0

peracetylated β-cyclodextrin

C9H14N4O4*C84H112O56

C9H14N4O4*C84H112O56

Conditions
ConditionsYield
With carbon dioxide at 45℃; under 258776 Torr; for 0.5h;
molsidomine
25717-80-0

molsidomine

trans-chloro(N3-morpholinyl-N6-ethylestersydnonimine-4-yl)bis(triphenylphosphine)palladium(II)

trans-chloro(N3-morpholinyl-N6-ethylestersydnonimine-4-yl)bis(triphenylphosphine)palladium(II)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium hexamethyldisilazane / tetrahydrofuran-d8; tetrahydrofuran / Inert atmosphere
2: tetrahydrofuran / -50 - 20 °C / Inert atmosphere
View Scheme
molsidomine
25717-80-0

molsidomine

C9H13(2)HN4O4

C9H13(2)HN4O4

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium hexamethyldisilazane / tetrahydrofuran-d8; tetrahydrofuran / Inert atmosphere
2: [D3]acetonitrile / 20 °C
View Scheme
molsidomine
25717-80-0

molsidomine

4-(methylseleno)molsidomine

4-(methylseleno)molsidomine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran-d8; tetrahydrofuran / Inert atmosphere
2.1: selenium / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
2.2: 0 - 20 °C / Inert atmosphere
View Scheme
molsidomine
25717-80-0

molsidomine

(N3-morpholinyl-N6-ethoxycarbonyl-sydnonimine-4-yl)(triphenylphosphine)gold(I)

(N3-morpholinyl-N6-ethoxycarbonyl-sydnonimine-4-yl)(triphenylphosphine)gold(I)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium hexamethyldisilazane / tetrahydrofuran-d8; tetrahydrofuran / Inert atmosphere
2: tetrahydrofuran / -50 - 20 °C / Inert atmosphere
View Scheme
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

molsidomine
25717-80-0

molsidomine

4-[(4'-chlorophenyl)hydroxymethyl]-3-morpholyl-N6-ethoxycarbonylsydnone imine

4-[(4'-chlorophenyl)hydroxymethyl]-3-morpholyl-N6-ethoxycarbonylsydnone imine

Conditions
ConditionsYield
Stage #1: molsidomine With n-butyllithium In tetrahydrofuran; hexane at -80 - 20℃; for 0.35h;
Stage #2: 4-chlorobenzaldehyde In tetrahydrofuran; hexane at 20℃; for 0.333333h; Reagent/catalyst; Time;
1-methoxy-N,N-dimethylmethanaminium methylsulphate

1-methoxy-N,N-dimethylmethanaminium methylsulphate

molsidomine
25717-80-0

molsidomine

4-formyl-3-morpholino-N6-ethoxycarbonylsydnone imine

4-formyl-3-morpholino-N6-ethoxycarbonylsydnone imine

Conditions
ConditionsYield
Stage #1: molsidomine With n-butyllithium In tetrahydrofuran; hexane at -80 - 20℃; for 0.183333h; Inert atmosphere;
Stage #2: 1-methoxy-N,N-dimethylmethanaminium methylsulphate In tetrahydrofuran; hexane; N,N-dimethyl-formamide at 20℃; for 0.333333h; Reagent/catalyst; Inert atmosphere;
66 %Spectr.

25717-80-0Downstream Products

25717-80-0Relevant articles and documents

Anionic N-heterocyclic carbenes derived from sydnone imines such as molsidomine. Trapping reactions with selenium, palladium, and gold

Freese, Tyll,Lücke, Ana-Luiza,Schmidt, Catharina A.S.,Polamo, Mika,Nieger, Martin,Namyslo, Jan C.,Schmidt, Andreas

, p. 5350 - 5357 (2017/08/11)

The sydnone imines Molsidomine and 5-(benzoylimino)-3-(2-methoxyphenyl)-1,2,3-oxadiazolium-2-ide gave anionic N-heterocyclic carbenes on deprotonation at C4 which were trapped as methylated selenium adducts, gold complexes (X-ray analysis) as well as palladium complexes (X-ray analysis). The 13C NMR resonance frequencies of the carbene carbon atom are extremely shifted upfield and appear at δ = 142.1 ppm (Molsidomine carbene) and δ = 159.8 ppm (sydnone imine carbene). The Pd complexes were applied as catalysts in Suzuki-Miyaura and Sonogashira-Hagihara cross-coupling reactions.

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