2-[Di(methylthio)methylidene]malononitrile supplier

Name
2-[DI(METHYLTHIO)METHYLIDENE]MALONONITRILE
EINECS
CAS No. 5147-80-8
Article Data41
CAS DataBase
Density 1.256 g/cm³
Solubility
Melting Point 76-78°C
Formula C6H6 N2 S2
Boiling Point 248.3 °C at 760 mmHg
Molecular Weight 170.259
Flash Point 103.9 °C
Transport Information 3439
Appearance orange
Safety 26-36/37/39
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.;
Synonyms Malononitrile,carbonyl-, dimethyl mercaptole (6CI,7CI,8CI); Propanedinitrile,[bis(methylthio)methylene]- (9CI); 1,1-Dicyano-2,2-bis(methylthio)ethene;1,1-Dicyano-2,2-bis(methylthio)ethylene;2,2-Bis(methylthio)-1,1-ethylenedicarbonitrile;2-Cyano-3,3-bis(methylthio)acrylonitrile;2-[Bis(methylsulfanyl)methylene]propanedinitrile;2-[Bis(methylthio)methylene]malononitrile;3,3-(Bismethylthio)-2-cyanoacronitrile;3,3-Bis(methylthio)-2-cyanoacrylonitrile;3,3-Di(methylthio)-2-cyanoacrylonitrile; NSC 202533;[2-Cyano-3,3-di(methylthio)]acrylonitrile;[Bis(methylthio)methylene]malononitrile; [Bis(methylthio)methylene]propanedinitrile;[Bis(methylthio)methylidene]propanedinitrile
PSA 98.18000
LogP 1.97116

Synthetic route

: 75-15-0
carbon disulfide

: 109-77-3
malononitrile

: 74-88-4
methyl iodide

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

Conditions

Conditions	Yield
With potassium carbonate; tetrabutylammomium bromide In benzene at 60℃; for 3h;	100%
Stage #1: malononitrile With potassium carbonate In dimethyl sulfoxide at 20℃; for 0.166667h; Large scale reaction; Stage #2: carbon disulfide In dimethyl sulfoxide at 0 - 22℃; for 0.5h; Large scale reaction; Stage #3: methyl iodide In dimethyl sulfoxide at 5 - 20℃; Large scale reaction;	99%
Stage #1: carbon disulfide; malononitrile With potassium carbonate In dimethyl sulfoxide at 0 - 20℃; for 2h; Stage #2: methyl iodide In dimethyl sulfoxide at 0 - 20℃; for 12h;	93.9%

...Expand

: 4777-48-4
potassium 1,1-dicyanoethylene-2,2-ditholate

: 74-88-4
methyl iodide

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

Conditions

Conditions	Yield
In water at 25 - 30℃; for 72h;	89%

: 106719-99-7
disodium iso-maleonitriledithiolate monohydrate

: 74-88-4
methyl iodide

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

Conditions

Conditions	Yield
	86%

: 75-15-0
carbon disulfide

: 77-78-1
dimethyl sulfate

: 109-77-3
malononitrile

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

Conditions

Conditions	Yield
Stage #1: carbon disulfide; malononitrile With sodium ethanolate In ethanol at 20℃; for 1h; Stage #2: dimethyl sulfate In ethanol	85%
Stage #1: malononitrile With potassium hydroxide In water; N,N-dimethyl-formamide at 0 - 20℃; for 2h; Stage #2: carbon disulfide In water; N,N-dimethyl-formamide at 20℃; for 1.5h; Stage #3: dimethyl sulfate In water; N,N-dimethyl-formamide at 0 - 20℃; for 4h;	85%
(i) NaOMe, MeOH, (ii) /BRN= 635994/; Multistep reaction;
Stage #1: malononitrile With potassium hydroxide at 20℃; Stage #2: carbon disulfide Stage #3: dimethyl sulfate

...Expand

: 2314-48-9
(S,S)-dimethyl trithiocarbonate

: C3Ag2N2

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

Conditions

Conditions	Yield
In methanol

: 77-78-1
dimethyl sulfate

: 2-Dimercaptomethylene-malononitrile; compound with ammonia

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

Conditions

Conditions	Yield
With sodium hydroxide

: 42717-51-1
2,2-Dicyano-1-mercapto-ethenethiolatetetrabutyl-ammonium;

: 74-88-4
methyl iodide

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

Conditions

Conditions	Yield
In N,N-dimethyl-formamide

: 20602-68-0
potassium (2,2-dicyano-1-methylsulfanylethen-1-yl)thiolate

: 74-88-4
methyl iodide

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

Conditions

Conditions	Yield
In ethanol

: 18771-14-7
dimercaptomethylene-malononitrile

: 77-78-1
dimethyl sulfate

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

Conditions

Conditions	Yield
In dimethyl sulfoxide for 2h; Ambient temperature; Yield given;

: 4885-93-2
2-(2,4-dithia-1,5-disodapentan-3-ylidene)propanedinitrile

CH3X, X=halogen: CH3X, X=halogen

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

Conditions

Conditions	Yield
In isopropyl alcohol Heating;

: 75-15-0
carbon disulfide

malononitrile, sodium-compound: malononitrile, sodium-compound

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

Conditions

Conditions	Yield
With diethyl ether; methyl iodide Einwoechiges Erwaermen des Reaktionsgemisches mit Methyljodid.;

: 77-78-1
dimethyl sulfate

: 109-77-3
malononitrile

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

Conditions

Conditions	Yield
With carbon disulfide; sodium methylate In methanol	18.6 g (11%)

: 75-15-0
carbon disulfide

: 109-77-3
malononitrile

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

Conditions

Conditions	Yield
alcoholic sodium methoxide
alcoholic sodium methoxide

: 4885-93-2
2-(2,4-dithia-1,5-disodapentan-3-ylidene)propanedinitrile

: 74-88-4
methyl iodide

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

Conditions

Conditions	Yield
In ice-water
In methanol
In ethanol at 20℃;

: 4777-48-4
potassium 1,1-dicyanoethylene-2,2-ditholate

: 77-78-1
dimethyl sulfate

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

Conditions

Conditions	Yield
In water

: 18771-14-7
dimercaptomethylene-malononitrile

: 74-88-4
methyl iodide

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

Conditions

Conditions	Yield
With tetrabutylammomium bromide In N,N-dimethyl-formamide at 60℃; for 64h; Inert atmosphere;	3.4 g
In dimethyl sulfoxide at 5 - 20℃; for 12h;	18.2 g

: 75-15-0
carbon disulfide

: 74-88-4
methyl iodide

: 1,3-dicyano-1,3-propanedione

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

Conditions

Conditions	Yield
Stage #1: carbon disulfide; 1,3-dicyano-1,3-propanedione With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 8.25h;

...Expand

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 100-46-9
benzylamine

: 152588-23-3
2-benzylamino-2-methylthio-1,1-ethylenedicarbonitrile

Conditions

Conditions	Yield
at 20℃;	100%
Heating;
In ethyl acetate

: 4897-50-1
4-piperidinopiperidin

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 904677-87-8
[(methylthio)(4-piperidinopiperidino)methylene]malononitrile

Conditions

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 0.25h;	100%

: C18H18N2O

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: C23H20N4OS

Conditions

Conditions	Yield
In xylene Heating;	100%

: 852913-53-2
9-amino-9-deoxy-epihydroquinine

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: C25H29N5OS

Conditions

Conditions	Yield
In tetrahydrofuran for 24h; Reflux;	100%

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 156-87-6
propan-1-ol-3-amine

: 904678-69-9
[1-(1-benzylpiperidin-4-ylamino)-2-(3-hydroxypropylamino)methylene]malononitrile

Conditions

Conditions	Yield
Stage #1: 4-amino-1-benzylpiperidine; [Bis(methylthio)methylene]malononitrile In tetrahydrofuran at 20℃; for 2.5h; Stage #2: propan-1-ol-3-amine In tetrahydrofuran at 60℃; for 16h;	99.5%

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 111-92-2
dibutylamine

: 85106-65-6
2-(Dibutylamino-methylsulfanyl-methylene)-malononitrile

Conditions

Conditions	Yield
In benzene Ambient temperature;	99%
In dichloromethane Heating;

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 2365-48-2
Methyl thioglycolate

: 129332-45-2
methyl 3-amino-4-cyano-5-(methylsulfanyl)-2-thiophenecarboxylate

Conditions

Conditions	Yield
With triethylamine In methanol for 2h; Reflux;	99%
With triethylamine In methanol for 1h; Heating;	84%
With triethylamine In methanol at 130℃; for 0.0666667h; Microwave irradiation;	82%
With triethylamine In methanol

: 536-90-3
m-Anisidine

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 155557-30-5
2-cyano-3-(3-methoxyphenylamino)-3-methylsulfanylacrylonitrile

Conditions

Conditions	Yield
In methanol for 15h; Heating;	99%
With 4-methoxy-aniline at 100℃; for 2h;	70%
Heating;
Stage #1: m-Anisidine; [Bis(methylthio)methylene]malononitrile In pyridine for 1h; Reflux; Stage #2: In pyridine

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 623-51-8
ethyl 2-sulfanylacetate

: 116170-90-2
3-amino-4-cyano-5-(methylthio)thiophene-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With triethylamine In methanol for 2h; Reflux;	99%
With triethylamine In methanol for 2h; Reflux;	99%
With triethylamine In ethanol at 0 - 20℃; for 12h;	72.6%

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 762-04-9
phosphonic acid diethyl ester

: 194095-91-5
(2,2-Dicyano-1-methylsulfanyl-vinyl)-phosphonic acid diethyl ester

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran	99%

: 7357-70-2
Cyanothioacetamide

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 2-amino-6-mercapto-4-(methylthio)pyridine-3,5-dicarbonitrile

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃;	99%
With triethylamine In N,N-dimethyl-formamide at 20℃; for 18h;	93%
With triethylamine In N,N-dimethyl-formamide at 20℃;	89%

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 100-63-0
phenylhydrazine

: 59334-11-1
5-amino-3-(methylsulfanyl)-1-phenyl-1H-pyrazole-4-carbonitrile

Conditions

Conditions	Yield
In methanol Heating;	98%
for 3h; Reflux;	96%
In ethanol
In ethanol Heating;
In ethanol

: 4-(2-methylpyrrolidin-1-ylmethyl)piperidine dihydrochloride

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 904677-53-8
{[4-(2-methylpyrrolidin-1-ylmethyl)piperidino](methylthio)methylene}malononitrile

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 0.25h;	98%

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 85068-29-7
3,5-bis-trifluoromethylbenzylamine

: 1598411-35-8
2-(((3,5-bis(trifluoromethyl)benzyl)amino)(methylthio)methylene)malononitrile

Conditions

Conditions	Yield
In tetrahydrofuran for 23h; Reflux; Green chemistry; stereoselective reaction;	98%
In methanol Reflux;
In tetrahydrofuran Reflux;

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 72760-85-1
5-amino-3-(methylsulfanyl)-1H-pyrazole-4-carbonitrile

Conditions

Conditions	Yield
With hydrazine hydrate In methanol for 3h; Heating;	97%
With hydrazine hydrate In ethanol Cooling with ice; Reflux;	85%
With hydrazine hydrate In methanol for 3h; Reflux;	80%

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 95-54-5
1,2-diamino-benzene

: 4933-40-8
2-(2,3-dihydro-1H-benzo[d]imidazolylidene)malononitrile

Conditions

Conditions	Yield
In ethanol for 24h; Heating;	97%
Stage #1: [Bis(methylthio)methylene]malononitrile; 1,2-diamino-benzene In ethanol for 8h; Reflux; Stage #2: With sodium ethanolate; N-Cyanoguanidine In ethanol for 5h; Reflux;	84%
In ethanol at 70℃; for 4h;	77.6%
In ethanol for 24h; Heating;

: 4-(N-methyl-N-phenylamino)piperidine dihydrochloride

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 904677-47-0
{[4-(N-methyl-N-phenylamino)piperidino](methylthio)methylene}malononitrile

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 0.25h;	97%

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 109-76-2
Trimethylenediamine

: 2-(hexahydropyrimidin-2-ylidene)malononitrile

Conditions

Conditions	Yield
In water at 25℃; regioselective reaction;	97%
	85%

: 1620-53-7
1-phenyl-2-pyridin-2-ylethanone

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 123366-01-8
1-Benzoyl-4-imino-2-methylsulfanyl-4H-quinolizine-3-carbonitrile

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide Ambient temperature;	96%

: 18166-02-4
N-trimethylsilylmethylamine

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 129757-45-5
2-[Methylsulfanyl-(trimethylsilanylmethyl-amino)-methylene]-malononitrile

Conditions

Conditions	Yield
In methanol for 0.166667h; Heating;	96%

: 109833-18-3
1-methyl-3-(2-ethoxy-2-oxoethyl)-1H-imidazol-3-ium bromide

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 139038-43-0
1-methylimidazolium N-(3,3-dicyano-1-ethoxycarbonyl-2-methylthio)allylide

Conditions

Conditions	Yield
With potassium carbonate In chloroform for 168h; Ambient temperature;	96%

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 60-23-1
Cysteamine

: 5718-93-4
2-(thiazolidin-2-ylidene)malononitrile

Conditions

Conditions	Yield
In ethanol for 2h; Heating;	96%
In ethanol at 20℃; for 4h;	73%
In water Reflux; regioselective reaction;	73%
In ethanol at 20℃; for 4h;	73%
In ethanol at 20℃; for 4h;

: 4439-20-7
N,N'-bis(2-hydroxyethyl)ethylene diamine

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 111161-06-9
[1,3-bis(2-hydroxyethyl)imidazolidin-2-ylidene]malononitrile

Conditions

Conditions	Yield
In tetrahydrofuran for 1h; Heating;	95.3%
In methanol for 14h; Heating;	92%

: 3197-06-6
N,N-bis(2-hydroxyethyl)ethylidenediamine

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 111161-06-9
[1,3-bis(2-hydroxyethyl)imidazolidin-2-ylidene]malononitrile

Conditions

Conditions	Yield
In tetrahydrofuran for 1h; Heating / reflux;	95.3%

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 111-41-1
2-(2-Aminoethylamino)ethanol

: 149138-82-9
<1-(2-hydroxyethyl)-2-imidazolidinylidene>malononitrile

Conditions

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 3h;	95.2%
In tetrahydrofuran at 20℃; for 2h;	95%
In toluene for 20h; Ambient temperature;	90%

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 137-07-5
2-amino-benzenethiol

: 4464-52-2
(2,3-dihydrobenzothiazol-2-ylidenyl)malonodinitrile

Conditions

Conditions	Yield
In ethanol for 24h; Heating;	95%
In ethanol for 6h; Heating;	90%
With piperidine In ethanol for 5h; Heating;	52%

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 60-34-4
methylhydrazine

: 151291-05-3
1H-1-methyl-3-amino-4-cyano-5-methylsulfanylpyrazole

Conditions

Conditions	Yield
In ethanol for 6h; Heating;	95%
In ethanol for 1h; Heating;	40%
In water
In water
Heating / reflux;

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 6975-75-3
4-((4-methoxyphenyl)diazenyl)-1H-pyrazole-3,5-diamine

: 155375-48-7
2,5-diamino-3-((4-methoxyphenyl)diazenyl)-7-(methylthio)pyrazolo[1,5-a]pyrimidine-6-carbonitrile

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 154℃; for 0.166667h; Microwave irradiation;	95%
With piperidine In ethanol for 4h; Heating;	85%

: 5147-80-8
[Bis(methylthio)methylene]malononitrile

: 3656-02-8
3,5-diamino-4-phenylazopyrazole

: 155375-38-5
2, 5-diamino-7-(methylthio)-3-(phenyldiazenyl)pyrazolo[1,5-a]pyrimidine-6-carbonitrile

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 154℃; for 0.166667h; Microwave irradiation;	95%
With piperidine In ethanol for 4h; Heating;	90%

2-[Di(methylthio)methylidene]malononitrile Chemical Properties

Molecule structure of Propanedinitrile,2-[bis(methylthio)methylene]- (CAS NO.5147-80-8):

IUPAC Name: 2-[Bis(methylsulfanyl)methylidene]propanedinitrile
Molecular Weight: 170.25524 [g/mol]
Molecular Formula: C₆H₆N₂S₂
XLogP3-AA: 1.4
H-Bond Acceptor: 2
Rotatable Bond Count: 2
Exact Mass: 169.99724
MonoIsotopic Mass: 169.99724
Topological Polar Surface Area: 47.6
Heavy Atom Count: 10
Index of Refraction: 1.584
Molar Refractivity: 45.41 cm³
Molar Volume: 135.4 cm³
Surface Tension: 54.6 dyne/cm
Density: 1.256 g/cm³
Melting Point: 76-78 °C
Flash Point: 103.9 °C
Enthalpy of Vaporization: 48.54 kJ/mol
Boiling Point: 248.3 °C at 760 mmHg
Vapour Pressure: 0.0245 mmHg at 25 °C
Canonical SMILES: CSC(=C(C#N)C#N)SC
InChI: InChI=1S/C6H6N2S2/c1-9-6(10-2)5(3-7)4-8/h1-2H3
InChIKey: FICQFRCPSFCFBY-UHFFFAOYSA-N
Product Categories of Propanedinitrile,2-[bis(methylthio)methylene]- (CAS NO.5147-80-8): Small molecule; Aliphatics

2-[Di(methylthio)methylidene]malononitrile Safety Profile

Hazard Codes: Toxic T, Irritant Xi
Risk Statements: 20/21/22-36/37/38
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39
RIDADR: 3439
Hazard Note: Toxic
HazardClass: IRRITANT

2-[Di(methylthio)methylidene]malononitrile Specification

Propanedinitrile,2-[bis(methylthio)methylene]-(CAS NO.5147-80-8) is also called (Bis(methylthio)methylene)propanedinitrile ; Propanedinitrile, (bis(methylthio)methylene)- ; [Bis(methylsulfanyl)methylene]malononitrile ; [Bis(Methylthio)Methylene]Malononitrile ; Propanedinitrile, (bis(methylthio)methylene)- ; [Bis(methylsulfanyl)methylidene]propanedinitrile .

Product Name

2-[DI(METHYLTHIO)METHYLIDENE]MALONONITRILE

Synthetic route

2-[Di(methylthio)methylidene]malononitrile Chemical Properties

2-[Di(methylthio)methylidene]malononitrile Safety Profile

2-[Di(methylthio)methylidene]malononitrile Specification

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