MALONONITRILE supplier | CasNO.109-77-3

Name
Malononitrile
EINECS 203-703-2
CAS No. 109-77-3
Article Data74
CAS DataBase
Density 1.049 g/cm³
Solubility 13.3 g/100 mL (20 °C) in water
Melting Point 30-32 °C(lit.)
Formula C₃H₂N₂
Boiling Point 218.499 °C at 760 mmHg
Molecular Weight 66.0623
Flash Point 112.222 °C
Transport Information UN 2647 6.1/PG 2
Appearance white crystalline powder
Safety 23-27-45-60-61
Risk Codes 23/24/25-50/53
Molecular Structure
Hazard Symbols T,N
Synonyms Methylene cyanide;dicyanomethane;Propanedinitrile;Methane, dicyano-;Malononitrile (nominals);Malonodinitrile;Malonsaeuredinitril;Cyanoacetonitrile;Malonic acid dinitrile;Methylenedinitrile;Nitril kyseliny malonove;dicyanmethane;Malononitrile (Malonitrile);Malonic Dinitrile;DWUMETYLOSULFOTLENKU (POLISH);NITRIL KYSELINY MALONOVE (CZECH);RCRA WASTE NUMBER U149;Usaf a-4600;
PSA 47.58000
LogP 0.42366

Synthetic route

: 123506-40-1
6-hydrazino-1,3-dimethyl-1H-pyrimidine-2,4-dione

: 2700-22-3
Benzylidenemalononitrile

A: 35221-08-0
1,7-Dihydro-5,7-dimethyl-3-phenyl-4H-pyrazolo<3,4-d>pyrimidin-4,6(5H)-dion

B: 1867-37-4
Benzylmalononitrile

C: 109-77-3
malononitrile

Conditions

Conditions	Yield
In propan-1-ol for 2h; Heating;	A 90% B 97% C 90%

...Expand

: 123506-40-1
6-hydrazino-1,3-dimethyl-1H-pyrimidine-2,4-dione

: 709-79-5
2-cyano-3-phenylacrylamide

A: 35221-08-0
1,7-Dihydro-5,7-dimethyl-3-phenyl-4H-pyrazolo<3,4-d>pyrimidin-4,6(5H)-dion

B: 1867-37-4
Benzylmalononitrile

C: 109-77-3
malononitrile

Conditions

Conditions	Yield
In propan-1-ol for 2h; Heating;	A 90% B 97% C 90%

...Expand

: 123506-40-1
6-hydrazino-1,3-dimethyl-1H-pyrimidine-2,4-dione

: 2025-40-3
ethyl benzylidenecyanoacetate

A: 35221-08-0
1,7-Dihydro-5,7-dimethyl-3-phenyl-4H-pyrazolo<3,4-d>pyrimidin-4,6(5H)-dion

B: 1867-37-4
Benzylmalononitrile

C: 109-77-3
malononitrile

Conditions

Conditions	Yield
In propan-1-ol for 2h; Heating;	A 90% B 97% C 90%

...Expand

: 773837-37-9
sodium cyanide

: 74-95-3
1,2-dibromomethane

: 109-77-3
malononitrile

Conditions

Conditions	Yield
With sodium iodide In dimethyl sulfoxide at 150℃; for 15h; Temperature; Sealed tube; Inert atmosphere;	95.14%

: potassium cyanide

: 74-95-3
1,2-dibromomethane

: 109-77-3
malononitrile

Conditions

Conditions	Yield
With potassium iodide at 160℃; for 8h; Sealed tube; Inert atmosphere;	95.01%

: 55042-38-1
3-(Chloromethyl)-2-benzoxazolinethione

: 151-50-8
potassium cyanide

A: 71528-27-3
3-<(2-Benzoxazolyl)thiomethyl>-2(3H)-benzoxazolethione

B: 109-77-3
malononitrile

Conditions

Conditions	Yield
In acetone for 24h; Product distribution; Mechanism; Heating;	A 95% B n/a

...Expand

: 107-91-5
cyanoacetic acid amide

: 109-77-3
malononitrile

Conditions

Conditions	Yield
With pyridine; phosgene In 1,2-dichloro-ethane at 75℃; for 15h; Solvent; Temperature; Reagent/catalyst;	94%
With phosgene; trichlorophosphate at 70 - 73℃; for 5 - 7h; Temperature;	93.59%
With pyridine; trichlorophosphate In water	76%

: 75-44-5
phosgene

: 107-91-5
cyanoacetic acid amide

: 109-77-3
malononitrile

Conditions

Conditions	Yield
With pyridine In 1,2-dichloro-ethane at 75℃; for 15h; Reagent/catalyst; Solvent; Temperature;	94%

: 41526-42-5
3-chloromethyl-3H-benzothiazole-2-thione

: 151-50-8
potassium cyanide

A: 77860-11-8
3-<(2-Benzothiazolyl)thiomethyl>-2(3H)-benzothiazolethione

B: 109-77-3
malononitrile

Conditions

Conditions	Yield
In acetone for 24h; Product distribution; Mechanism; Heating;	A 92% B n/a

...Expand

: potassium cyanide

: 75-09-2
dichloromethane

: 109-77-3
malononitrile

Conditions

Conditions	Yield
With potassium iodide at 155℃; for 12h; Sealed tube; Inert atmosphere;	91.04%

: 69245-79-0
2-(N-morpholinyl)methyl-4-nitrophenol

A: 76226-59-0
4-amino-2-morpholinomethylphenol

B: 109-77-3
malononitrile

Conditions

Conditions	Yield
With hydrazine hydrate	A 91% B 52%

: 74-90-8
hydrogen cyanide

: 107-14-2
chloroacetonitrile

: 109-77-3
malononitrile

Conditions

Conditions	Yield
at 160℃; Temperature; Inert atmosphere;	89.53%

: 773837-37-9
sodium cyanide

: 75-09-2
dichloromethane

: 109-77-3
malononitrile

Conditions

Conditions	Yield
With aluminum (III) chloride; tetrabutylammomium bromide at 90℃; for 8h; Reagent/catalyst;	89%

: 108-13-4
malonodiamide

: 109-77-3
malononitrile

Conditions

Conditions	Yield
With phosphorus pentoxide under 15.0015 - 37.5038 Torr; for 1h; Temperature; Heating;	86%
With phosphorus pentaoxide
With phosphorus pentoxide at 250℃; under 15001.5 - 37503.8 Torr; for 1h; Temperature;
under 15.0015 - 37.5038 Torr; for 1h; Temperature; Heating;

: 1885-22-9
bromomalononitrile

: 109-77-3
malononitrile

Conditions

Conditions	Yield
With bis(triethylgermyl)mercury In tetrahydrofuran at 20℃; for 0.333333h;	78.3%
With 3-Methyl-2-phenyl-2,3-dihydrobenzothiazoline; tris(2,2'-bipyridyl)ruthenium dichloride In [D3]acetonitrile at 20℃; for 0.7h; Irradiation;

: 108-77-0
1,3,5-trichloro-2,4,6-triazine

: 107-91-5
cyanoacetic acid amide

A: 108-80-5
isocyanuric acid

B: 109-77-3
malononitrile

Conditions

Conditions	Yield
N,N-dimethyl-formamide In acetonitrile at 50 - 60℃; for 11 - 12h;	A n/a B 67%
N,N-dimethyl-formamide In tetrahydrofuran at 50 - 60℃; for 11 - 12h;	A n/a B 53%
N,N-dimethyl-formamide In 1,4-dioxane at 50 - 60℃; for 11 - 12h;	A n/a B 44%

...Expand

: 15666-97-4
octyl 2-cyanoacetate

: 670-54-2
ethenetetracarbonitrile

A: n-Octyl tricyanoacrylate

B: 109-77-3
malononitrile

Conditions

Conditions	Yield
With pyridine In tetrahydrofuran at 65℃; for 0.75h;	A 63% B n/a

...Expand

: 108-77-0
1,3,5-trichloro-2,4,6-triazine

: 107-91-5
cyanoacetic acid amide

: 109-77-3
malononitrile

Conditions

Conditions	Yield
N,N-dimethyl-formamide In ethyl acetate at 50 - 60℃; for 11 - 12h;	52%

: 14447-18-8
benzyl 2-cyanoacetate

: 670-54-2
ethenetetracarbonitrile

A: Benzyl tricyanoacrylate

B: 109-77-3
malononitrile

Conditions

Conditions	Yield
With pyridine In tetrahydrofuran at 65℃; for 0.75h;	A 48% B n/a

...Expand

: 45497-73-2
aniline hydroiodide

: 139952-06-0
Hexacyanocyclopropane

A: 41996-49-0
anilino-ethenetricarbonitrile

B: 109-77-3
malononitrile

Conditions

Conditions	Yield
In ethyl acetate at 40℃; Mechanism; other amine hydroiodides, reaction time 3-5 min;	A 46% B n/a

...Expand

: 1116-98-9
cyanoacetic acid tert-butyl ester

: 670-54-2
ethenetetracarbonitrile

A: 833447-41-9
tert-butyl tricyanoethylenecarboxylate

B: 109-77-3
malononitrile

Conditions

Conditions	Yield
With pyridine In tetrahydrofuran for 40h; Michael addition; Reflux;	A 41% B n/a

...Expand

: 14447-15-5
cyanoacetic acid n-propyl ester

: 670-54-2
ethenetetracarbonitrile

A: n-Propyl tricyanoacrylate

B: 109-77-3
malononitrile

Conditions

Conditions	Yield
With pyridine In tetrahydrofuran at 65℃; for 0.75h;	A 38% B n/a

...Expand

: 13361-32-5
allyl cyanoacetate

: 670-54-2
ethenetetracarbonitrile

A: 1142329-69-8
allyl tricyanoethylenecarboxylate

B: 109-77-3
malononitrile

Conditions

Conditions	Yield
With pyridine In tetrahydrofuran for 40h; Michael addition; Reflux;	A 26% B n/a

...Expand

: 59181-71-4
9-Cyano-10-methyl-10-thiaanthracene

: 670-54-2
ethenetetracarbonitrile

A: 59181-21-4
9-Cyano-9-methylthioxanthene

B: 59215-71-3
9-Cyano-9-(dicyanomethyl)thioxanthene

C: 492-22-8
thio-xanthene-9-one

D: 66223-43-6
2,2,3,3-Tetracyanobutane

E: 109-77-3
malononitrile

Conditions

Conditions	Yield
In tetrahydrofuran Mechanism;	A 8.5% B 11% C 13% D 24% E 120 mg

...Expand

: 670-54-2
ethenetetracarbonitrile

: 105-56-6
ethyl 2-cyanoacetate

A: 153814-39-2
ethyl tricyanoethylenecarboxylate

B: 109-77-3
malononitrile

Conditions

Conditions	Yield
With pyridine In tetrahydrofuran at 65℃; for 0.75h;	A 22% B n/a
With pyridine In tetrahydrofuran for 40h; Michael addition; Reflux;	A 14% B n/a

...Expand

: 670-54-2
ethenetetracarbonitrile

: 105-34-0
methyl 2-cyanoacetate

A: 101342-43-2
methyl tricyanoethylenecarboxylate

B: 109-77-3
malononitrile

Conditions

Conditions	Yield
With pyridine In tetrahydrofuran for 40h; Michael addition; Reflux;	A 4% B n/a

...Expand

: 107-13-1
acrylonitrile

: 109-77-3
malononitrile

Conditions

Conditions	Yield
durch Copolymerisation(Herstellung);

: 75-05-8
acetonitrile

: 506-77-4
cyanogen chloride

: 109-77-3
malononitrile

Conditions

Conditions	Yield
With carbon dioxide at 650℃;

: 5666-55-7
(phenylsulfonyl)phosphorimidic trichloride

: 1663-67-8
malonoyl dichloride

: 109-77-3
malononitrile

Conditions

Conditions	Yield
at 130℃;

: 98-01-1
furfural

: 109-77-3
malononitrile

: 3237-22-7
2-cyano-3-(2-furanyl)acrylonitrile

Conditions

Conditions	Yield
With 1-butyl-1,4-diazabicyclo[2.2.2]octanylium hydrotetrafluoroborate In water at 20℃; for 0.0166667h; Knoevenagel condensation;	100%
With 1,4-diaza-bicyclo[2.2.2]octane In water at 20℃; for 0.0166667h; Knoevenagel Condensation; Green chemistry;	100%
With hydroquinone; p-benzoquinone In water at 20℃; for 3h; Reagent/catalyst; Knoevenagel Condensation; Inert atmosphere; Sealed tube;	100%

: 120-57-0
piperonal

: 109-77-3
malononitrile

: 2972-82-9
2-benzo[1,3]dioxol-5-ylmethylene-malononitrile

Conditions

Conditions	Yield
In ethanol; water at 75℃; for 0.166667h; Knoevenagel Condensation;	100%
With strong base anion-exchange resin In water at 20℃; for 1.4h; Knoevenagel condensation;	98%
With antimony(III) chloride for 0.0666667h; Knoevenagel condensation; microwave irradiation;	96%

: 108-94-1
cyclohexanone

: 109-77-3
malononitrile

: 4354-73-8
2-(cyclohexylidene)malononitrile

Conditions

Conditions	Yield
hydrotalcite structure integrating fluoride ions In DMF (N,N-dimethyl-formamide) at 25℃; for 2h; Conversion of starting material; Knoevenagel Condensation;	100%
With 1-butyl-1,4-diazabicyclo[2.2.2]octanylium hydrotetrafluoroborate In water at 20℃; for 0.0333333h; Knoevenagel condensation;	100%
Ru(+)Cp(NCCHCO2Et)(-)(PPh3)2 In tetrahydrofuran at 25℃; for 5h; Condensation; Aldol reaction;	99%

: 104-88-1
4-chlorobenzaldehyde

: 109-77-3
malononitrile

: 1867-38-5
4-chlorobenzylidenemalonodinitrile

Conditions

Conditions	Yield
at 150℃; for 1h; Knoevenagel condensation;	100%
hydrotalcite structure integrating fluoride ions In DMF (N,N-dimethyl-formamide) at 25℃; for 0.25h; Conversion of starting material; Knoevenagel Condensation;	100%
With 1-butyl-1,4-diazabicyclo[2.2.2]octanylium hydrotetrafluoroborate In water at 20℃; for 0.0333333h; Knoevenagel condensation;	100%

: 89-98-5
2-chloro-benzaldehyde

: 109-77-3
malononitrile

: 2698-41-1
o-chlorobenzylidene malononitrile

Conditions

Conditions	Yield
With poly(4-vinylpyridine) supported on MCM-48 at 25℃; for 0.133333h; Knoevenagel condensation; neat (no solvent);	100%
Stage #1: malononitrile; piperidine In water at 20 - 30℃; Stage #2: 2-chloro-benzaldehyde In water at 50℃; Product distribution / selectivity; Knoevenagel Condensation;	99.5%
In N,N-dimethyl-formamide for 1h; Knoevenagel Condensation;	99.9%

: 66-77-3
1-naphthaldehyde

: 109-77-3
malononitrile

: 2972-83-0
(1-naphthylmethylidene)malononitrile

Conditions

Conditions	Yield
With aluminum oxide Inert atmosphere; Neat (no solvent);	100%
With 1,4-diaza-bicyclo[2.2.2]octane In water at 20℃; for 0.05h; Knoevenagel Condensation; Green chemistry;	100%
With polystyrene-supported DABCO In methanol at 25℃; for 0.8h; Knoevenagel Condensation; Green chemistry;	99%

: 99-61-6
3-nitro-benzaldehyde

: 109-77-3
malononitrile

: 2826-32-6
3-nitrobenzylidenemalononitrile

Conditions

Conditions	Yield
With C7H15N4(1+)*BF4(1-) In water at 20℃; for 0.0166667h; Knoevenagel Condensation; Green chemistry;	100%
With sodium sulfide; aluminum oxide In dichloromethane at 20℃; for 0.0833333h; Knoevenagel reaction;	99%
With third generation polystyrene supported poly(amidoamine) dendrimer In ethanol at 30℃; for 0.25h; Knoevenagel condensation;	99%

: 555-16-8
4-nitrobenzaldehdye

: 109-77-3
malononitrile

: 2700-23-4
4-Nitrobenzylidenemalononitrile

Conditions

Conditions	Yield
at 150℃; for 1h; Knoevenagel condensation;	100%
In various solvent(s) at 20℃; for 3h; Knoevenagel condensation;	100%
hydrotalcite structure integrating fluoride ions In acetonitrile at 25℃; for 1.5h; Conversion of starting material; Knoevenagel Condensation;	100%

: 100-52-7
benzaldehyde

: 109-77-3
malononitrile

: 2700-22-3
Benzylidenemalononitrile

Conditions

Conditions	Yield
With calcite grains for 0.5h; Product distribution; Further Variations:; Reagents; Knoevenagel condensation; ball-milling conditions;	100%
at 150℃; for 1h; Knoevenagel condensation;	100%
With 3-(1-piperazino)propyl functionalised silica gel In acetonitrile Knoevenagel condensation;	100%

: 123-08-0
4-hydroxy-benzaldehyde

: 109-77-3
malononitrile

: 3785-90-8
2-(4-hydroxyphenylmethylene)malononitrile

Conditions

Conditions	Yield
at 150℃; for 1h; Knoevenagel condensation;	100%
hydrotalcite structure integrating fluoride ions In acetonitrile at 25℃; for 1.5h; Conversion of starting material; Knoevenagel Condensation;	100%
With polymer supported poly(propylene imine)dendrimer In ethanol at 20℃; for 0.166667h; Knoevenagel Condensation; Green chemistry;	100%

: 123-11-5
4-methoxy-benzaldehyde

: 109-77-3
malononitrile

: 2826-26-8
2-(4-methoxyphenylmethylene)malononitrile

Conditions

Conditions	Yield
With third generation polystyrene supported poly(amidoamine) dendrimer In ethanol at 30℃; for 0.25h; Knoevenagel condensation;	100%
With [3-(3-silica-supported-propyl)-1-(2,4,6-trimethylphenyl)-1H-imidazol-3-ium iodide]*10SiO2 at 100℃; for 16h; Knoevenagel condensation;	100%
With ethylenediamine-modified poly(vinyl chloride) at 20℃; for 0.05h; Solvent; Knoevenagel Condensation; Green chemistry;	100%

: 121-33-5
vanillin

: 109-77-3
malononitrile

: 3696-12-6
2-(4-hydroxy-3-methoxybenzylidene)malononitrile

Conditions

Conditions	Yield
With third generation polystyrene supported poly(amidoamine) dendrimer In ethanol at 30℃; for 0.333333h; Knoevenagel condensation;	100%
With polymer supported poly(propylene imine)dendrimer In ethanol at 20℃; for 0.0833333h; Knoevenagel Condensation; Green chemistry;	99%
With Zn(1+)*C5H8NO2(1-) In water at 80℃; for 0.166667h; Knoevenagel Condensation;	99%

: 120-14-9
3,4-dimethoxy-benzaldehyde

: 109-77-3
malononitrile

: 2972-80-7
3,4-dimethoxybenzylidenemalononitrile

Conditions

Conditions	Yield
With polymer supported poly(propylene imine)dendrimer In ethanol at 20℃; for 0.0833333h; Knoevenagel Condensation; Green chemistry;	100%
With third generation polystyrene supported poly(amidoamine) dendrimer In ethanol at 30℃; for 0.333333h; Knoevenagel condensation;	99%
With antimony(III) chloride for 0.0416667h; Knoevenagel condensation; microwave irradiation;	97%

: 107-13-1
acrylonitrile

: 109-77-3
malononitrile

: 63877-68-9
4,4-dicyano-heptanedinitrile

Conditions

Conditions	Yield
With 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane hydroxide at 20℃; for 0.0166667h; Michael Addition; Green chemistry;	100%
With 1-butyl-3-methylimidazolium hydroxide at 20℃; for 1h; Michael addition;	96%
With tetra(n-butyl)ammonium hydroxide In N,N-dimethyl-formamide for 3h; electrolysis;	95%

: 98-86-2
acetophenone

: 109-77-3
malononitrile

: 5447-87-0
2-(1-phenylethylidene)propanedinitrile

Conditions

Conditions	Yield
With ethylenediamine-modified poly(vinyl chloride) at 20℃; for 0.116667h; Solvent; Knoevenagel Condensation; Green chemistry;	100%
With third generation polystyrene supported poly(amidoamine) dendrimer In ethanol at 50℃; for 0.5h; Knoevenagel condensation;	98%
With MIL-53(Fe) metal organic framework encapsulated on silica-coated nickel ferrite magnetic nanoparticles In ethanol at 20℃; for 2h; Knoevenagel Condensation;	95%

: 135-02-4
ortho-anisaldehyde

: 109-77-3
malononitrile

: 2834-10-8
2-(2-methoxybenzylidene)malononitrile

Conditions

Conditions	Yield
hydrotalcite structure integrating fluoride ions In DMF (N,N-dimethyl-formamide) at 25℃; for 0.25h; Conversion of starting material; Knoevenagel Condensation;	100%
With polyacrylonitrile fiber functionalized with N,N-dimethyl-1,3-propanediamine In ethanol at 20℃; for 1h; Knoevenagel condensation;	99%
With polyacrylonitrile fiber modified with triethylenetetramine In water at 20℃; for 1.5h; Knoevenagel condensation;	99%

: 100-10-7
4-dimethylamino-benzaldehyde

: 109-77-3
malononitrile

: 2826-28-0
p-(N-dimethylamino benzylidene) malononitrile

Conditions

Conditions	Yield
With third generation polystyrene supported poly(amidoamine) dendrimer In ethanol at 30℃; for 0.333333h; Knoevenagel condensation;	100%
With polymer supported poly(propylene imine)dendrimer In ethanol at 20℃; for 0.0833333h; Knoevenagel Condensation; Green chemistry;	100%
With potassium hydrogen phthalate In water at 20℃; for 0.116667h; Knoevenagel Condensation; Green chemistry;	99%

: 529-34-0
3,4-dihydronaphthalene-1(2H)-one

: 109-77-3
malononitrile

: 2510-03-4
1,2,3,4-tetrahydro-1-naphthylidene malononitrile

Conditions

Conditions	Yield
With aluminum oxide Inert atmosphere; Neat (no solvent);	100%
With ammonium acetate; acetic acid In toluene for 10h; Reflux; Dean-Stark;	93%
With 1-butyl-3-methylimidazolium hydroxide at 25 - 30℃; for 0.666667h; Knoevenagel condensation;	89%

: 552-89-6
2-nitro-benzaldehyde

: 109-77-3
malononitrile

: 2826-30-4
2-(2-nitrobenzylidene)malononitrile

Conditions

Conditions	Yield
With Fe3O4(at)SiO2-N1-(3-trimethoxysilylpropyl)diethylenetriamine nanoparticles catalyst In toluene at 75℃; for 0.75h; Solvent; Knoevenagel Condensation;	100%
With hydroquinone; p-benzoquinone In water at 20℃; for 3h; Knoevenagel Condensation; Inert atmosphere; Sealed tube;	100%
With Zr(IV)-salen-MCM-41 In water at 35℃; for 0.5h; Catalytic behavior; Solvent; Knoevenagel Condensation;	99%

: 1013-88-3
Benzophenone imine

: 109-77-3
malononitrile

: 10394-96-4
2-(diphenylmethylene)malononitrile

Conditions

Conditions	Yield
at 20℃; for 0.0833333h; Inert atmosphere; Neat (no solvent);	100%
With ammonium acetate; acetic acid In tetrahydrofuran at 20℃; for 1.08333h; Dean-Stark; Schlenk technique; Inert atmosphere;	85%

: 3132-99-8
m-bromobenzoic aldehyde

: 109-77-3
malononitrile

: 2972-74-9
2-(3-bromobenzylidene)malononitrile

Conditions

Conditions	Yield
With glycine In dichloromethane	100%
With ethanolamine-phosphoric acid functionalized polyacrylonitrile fibers, hydrophobized with benzylamine (Bn-PANEAPF) In water at 20℃; for 2h; Knoevenagel Condensation; Green chemistry;	99%
In various solvent(s) at 50℃; for 3h; Knoevenagel condensation;	98%

: 486-25-9
9-fluorenone

: 109-77-3
malononitrile

: 1989-32-8
2-fluoren-9-ylidene-malononitrile

Conditions

Conditions	Yield
for 0.0833333h; Inert atmosphere; Neat (no solvent);	100%
With piperidine In ethanol at 20℃; for 0.5h; Knoevenagel condensation;	87%
With ethanol; ammonia

: 109-77-3
malononitrile

: 506-77-4
cyanogen chloride

: 36603-80-2
sodium tricyanomethanide

Conditions

Conditions	Yield
With phosphoric acid; sodium hydroxide In methanol; water at 25 - 30℃; for 3.5h; pH=7.0 - 7.2; Product distribution / selectivity;	100%
With ethanol; sodium

: 104-87-0
4-methyl-benzaldehyde

: 109-77-3
malononitrile

: 2826-25-7
2-(4-methylbenzylidene)malononitrile

Conditions

Conditions	Yield
With L-arginine at 20℃; for 0.0833333h; Knoevenagel condensation; Ionic liquid;	100%
With 1,4-diaza-bicyclo[2.2.2]octane In water at 20℃; for 0.0333333h; Knoevenagel Condensation; Green chemistry;	100%
With 2C9H3O6(3-)2C27H18N63Ni(2+)15H2O5C2H6O In dichloromethane at 60℃; for 2h; Knoevenagel Condensation; Inert atmosphere;	100%

: 100-39-0
benzyl bromide

: 109-77-3
malononitrile

: 3779-31-5
2,2-dibenzylmalononitrile

Conditions

Conditions	Yield
With potassium carbonate; tetrabutylammomium bromide for 96h; Ambient temperature;	100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; for 2h;	91%
With 1-butyl-3-methylimidazolium hydroxide at 100℃; under 51.7148 Torr; for 0.0833333h; microwave irradiation;	82%

: 459-57-4
4-fluorobenzaldehyde

: 109-77-3
malononitrile

: 2826-22-4
4-fluorobenzylidenemalononitrile

Conditions

Conditions	Yield
With 1-(3-silica-supported propyl)-3-[(3-{[1-(3-silica-supported propyl)-4,5-dihydro-1H-imidazol-3-ium-3-yl]methyl}-2,4,6-trimethylphenyl)methyl]-4,5-dihydro-1H-imidazol-3-ium chloride at 100℃; for 4h; Knoevenagel condensation;	100%
With 2C9H3O6(3-)2C27H18N63Ni(2+)15H2O5C2H6O In dichloromethane at 60℃; for 2h; Knoevenagel Condensation; Inert atmosphere;	100%
With N,N-dimethyl-N-hydroxyethylammonium acetate at 20℃; for 0.0333333h; Knoevenagel Condensation;	99%

: 134-81-6
benzil

: 109-77-3
malononitrile

: 23195-86-0
2-(2-oxo-1,2-diphenylethylidene)malononitrile

Conditions

Conditions	Yield
With third generation polystyrene supported poly(amidoamine) dendrimer In ethanol at 50℃; for 2h; Knoevenagel condensation;	100%
With N,N-dimethyl-aniline In ethanol
With potassium carbonate In ethanol for 8h; Reflux;

: 1963-36-6
4-methoxycinnamaldehyde

: 109-77-3
malononitrile

: 122055-54-3
4-(4-methoxyphenyl)-1,1-dicyano-1,3-butadiene

Conditions

Conditions	Yield
With L-arginine at 20℃; for 0.0666667h; Knoevenagel condensation; Ionic liquid;	100%
With piperidine
Knoevenagel Condensation; Alkaline conditions;

: 927-49-1
dipentyl ketone

: 109-77-3
malononitrile

: 13017-59-9
2-(1-pentyl-hexylidene)-malononitrile

Conditions

Conditions	Yield
	100%
With 5% active carbon-supported ruthenium In ethanol at 78℃; for 18h;	94.7%
With ammonium acetate; acetic acid

: 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

MALONONITRILE Chemical Properties

Malononitrile(109-77-3) is a nitrile and it is also called propanedinitrile with formula CH₂(CN)₂. Malononitrile(109-77-3)'s Pka in water is 11, which is relatively acidic. malononitrile(109-77-3) is used as a suitable starting material for the Gewald reaction, in related chemistry. In Gewald reaction, a 2-aminothiophenethe is produced by nitrile condenses with a ketone or aldehyde in the presence of elemental sulfur and a base.

Product Name:Malononitrile
CAS No:109-77-3
Synonyms:AKOS BBS-00004370;METHYLENE DICYANIDE;METHYLENE CYANIDE;MALONODINITRILE;MALONITRILE;MALONONITRILE;MALONIC ACID DINITRILE;MDN
Molecular Formula:C₃H₂N₂
Formula Weight:66.06
Density:1.049 g/mL at 25 °C(lit.)
Melting Point:30-32 °C(lit.)
Boiling Point:220 °C(lit.)
Refractive Index:1.4150
Flash Point:234 °F
Molecular Structure:

MALONONITRILE Uses

1. Malononitrile is used in the Knoevenagel condensation, such as CS gas' preparation.

2. malononitrile is used as a suitable starting material for the Gewald reaction in related chemistry. In Gewald reaction, the nitrile condenses with a ketone or aldehyde in the presence of elemental sulfur and a base to produce a 2-aminothiophene.

MALONONITRILE Toxicity Data With Reference

1.	eye-rbt 5 mg/24H SEV	85JCAE Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,899.
2.	orl-rat LD50:60,800 μg/kg	28ZPAK Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,158.
3.	skn-rat LD50:350 mg/kg	MEPAAX Medycyna Pracy. Industrial Medicine. 27 (1976),1.
4.	LD50:20,550 μg/kg	MEPAAX Medycyna Pracy. Industrial Medicine. 27 (1976),1.
5.	scu-rat LD50:31,500 μg/kg	. 27 (1976),1.
	orl-mus LD50:19 mg/kg	KHZDAN Khigiena i Zdraveopazvane. 9 (1966),50.
7.	scu-rat LDLo:7 mg/kg	AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. 3 (1897),77.
8.	ipr-mus LD50:13 mg/kg	NATUAS Nature. 228 (1970),1315.
	LDLo:8 mg/kg	AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. 3 (1897),77.
10.	ivn-mus

MALONONITRILE Consensus Reports

Cyanide and its compounds are on the Community Right-To-Know List. EPA Extremely Hazardous Substances List. Reported in EPA TSCA Inventory.

MALONONITRILE Safety Profile

Poison by ingestion, skin contact, subcutaneous, intravenous, and intraperitoneal routes. A severe eye irritant. Combustible when exposed to heat or flame. Polymerizes violently when heated to 130°C or on contact with strong base. May spontaneously explode when stored at 70–80°C. To fight fire, use water, fog, spray, foam. When heated to decomposition it emits toxic fumes of NO_x and CN⁻.

Hazard Codes T,N
Risk Statements 23/24/25-50/53
Safety Statements 23-27-45-60-61
RIDADR UN 2647 6.1/PG 2
WGK Germany 3
RTECS OO3150000
F 8
HazardClass 6.1
PackingGroup II

MALONONITRILE Standards and Recommendations

NIOSH REL: (Nitriles) TWA 8 mg/m³
DOT Classification: 6.1; Label: Poison

Product Name

Malononitrile

Synthetic route

MALONONITRILE Chemical Properties

MALONONITRILE Uses

MALONONITRILE Toxicity Data With Reference

MALONONITRILE Consensus Reports

MALONONITRILE Safety Profile

MALONONITRILE Standards and Recommendations

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