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Malononitrile suppliers in China
Cas No: 109-77-3
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
Malononitrile, Methylene dicyanide, Malonitrile, Malonodinitrile, MDN
Cas No: 109-77-3
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High quality Malononitrile   supplier in China
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High purity Various Specifications Malononitrile CAS:109-77-3
Cas No: 109-77-3
USD $ 100.0-500.0 / Gram 1 Gram 99999 Gram/Year Hangzhou Dingyan Chem Co., Ltd Contact Supplier
Malononitrile
Cas No: 109-77-3
USD $ 2.0-2.0 / Gram 1 Gram 500 Metric Ton/Year Jinan Finer Chemical Co., Ltd Contact Supplier
Malonodinitrile
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Malononitrile
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USD $ 2.0-3.0 / Kilogram 1 Kilogram 50 Metric Ton/Day EAST CHEMSOURCES LIMITED Contact Supplier
Factory Supply Malononitrile
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Malononitrile 109-77-3
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Amadis Chemical offer CAS#109-77-3;CAT#A15111
Cas No: 109-77-3
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109-77-3 Usage

Chemical Properties

Malononitrile may polymerize violently on prolonged heating at 130°C or at lower temperatures on contact with strong bases.

Health Hazard

Metabolized by body to cyanide and thiocyanate; effects of inhalation of toxic fumes will be related to cyanide. Causes brain and heart damage related to lack of cellular oxygen. It is classified as extremely toxic. Probable oral lethal dose for humans is 5-50 mg/kg, or between 7 drops and 1 teaspoonful, for a 70 kg (150 lb.) person.

Air & Water Reactions

Soluble in water.

Purification Methods

Crystallise the nitrile from water, EtOH, *benzene or chloroform. Distil it in a vacuum from, and store over, P2O5. [Bernasconi et al. J Am Chem Soc 107 7692 1985, Gratenhuis J Am Chem Soc 109 8044 1987, Beilstein 2 IV 1892.]

Waste Disposal

Generators of waste containing this contaminant (≥100 kg/mo) must conform to EPA regulations governing storage, transportation, treatment, and waste disposal

General Description

A white-colored crystalline solid. Denser than water and soluble in water. Toxic by ingestion and may severely irritate skin and eyes. May polymerize violently if exposed to temperatures above 266°F. Used to make other chemicals.

Health Hazard

Malononitrile is a highly toxic compound by all toxic routes. Its acute toxicity is somewhat greater than that of the aliphatic mononitriles, propionitrile, and butyronitrile. The increased toxicity may be attributed to the greater degree of reactivity in the molecule arising from two- CN functional groups. The acute toxic symptoms in test animals have not been well documented. An intraperitoneal dose of 10 mg/kg was lethal to rats. LD50 value, intravenous (rabbits): 28 mg/kg LD50 value, oral (mice): 19 mg/kg Malononitrile is an eye irritant. The irritation from 5 mg in 24 hours was severe in rabbits’ eyes. There is no report of teratogenic and carcinogenic action in animals or humans.

Production Methods

Malononitrile is prepared by continuous introduction of preheated acetonitrile and cyanogen chloride into a tube reactor until the reaction mixture reaches a temperature of approximately 780°C.

Fire Hazard

When heated to decomposition, Malononitrile emits highly toxic fumes (cyanide). May polymerize violently on prolonged heating. Avoid heat. Hazardous polymerization may occur, at prolonged heating at 266F or contact with strong bases at lower temperatures.

Chemical Properties

Malononitrile is a white powder or colorless, odorless crystalline substance.

Industrial uses

Malononitrile is used primarily as an intermediate in the synthesis of drugs and vitamins (thiamine). It has also been employed in the manufacture of photosensitizes, acrylic fibers and dyestuffs and as an oil-soluble polar additive in lubricating oil. Malononitrile was used formerly in treatment of various forms of mental illness such as alteration of psychic functions and schizophrenic disorders.

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 NOx and CN-. See also NITRILES.

Metabolism

The in vitro metabolsim of malononitrile has been described by Stern et al. In the presence of thiosulphate, brain, liver and kidney slices metabolized malononitrile to thiocyanate. The formation of thiocyanate from malononitrile and thiosulphate was greatest in the presence of liver slices, lowest in brain, and intermediate with kidney slices. The liver enzyme system was saturated at a concentration of 3.3 mM malononitrile and a pH optimum of 7.0. This enzyme system was inhibited by cysteine and glutathione and inactivated by boiling. Stern et al indicated that thiosulphate increased cyanide and thiocyanate formed from malononitrile in tissue slices.

Incompatibilities

Incompatible with strong bases. May polymerize violently on prolonged heating @ 129C, or in contact with strong bases at lower temperatures. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.

Chemical Properties

Solidified melt

Hazard

Toxic by ingestion and inhalation.

Potential Exposure

Malononitrile is used in organic synthesis; as a lubricating oil additive; for thiamine synthesis; for pteridine-type anticancer agent synthesis; and in the synthesis of photosensitizers, acrylic fibers, and dyestuffs. It has also been used in the treatment of various forms of mental illness. It has been used as a leaching agent for gold

Health Hazard

In the late 1940's, malononitrile was used experimentally in the treatment of schizophrenia and depression. Patients were given an iv infusion of 5% malononi-trile for 10-69 min. The total dose during such treatments was 1-6 mg/kg and treatments were given 2-3 times/wk. Ten to twenty min after beginning infusion, all patients experienced tachycardia. In addition, redness, nausea, vomiting, headache, shivering, muscle spasms, and numbness were reported with varying frequency.

Definition

ChEBI: A dinitrile that is methane subtituted by two cyano groups.

Shipping

UN2647 Malononitrile, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN3439 Nitriles, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required

Reactivity Profile

Malononitrile is a white, low-melting powder (m. p. 30.5° C), toxic, combustible. Violent polymerization on contact with strong bases (sodium hydroxide, potassium hydroxide) or when heated above 130° C. When stored at 70-80° C for 2 months, spontaneous explosion (decomposition) occurred [Bretherick, 5th ed., 1995, p. 394].

Uses

Malononitrile is used in organic synthesis.

Uses

Malononitrile is an important building block for the syntheses of pharmaceuticals (e.g. triamterene, adenine and methotrexate), thiamin (vitamin B1), pesticides dyestuffs for color photography and synthetic fibers (e.g. vinylidene cyanide). Product Data Sheet

Uses

The chemical properties of malononitrile are determined by the nucleophilicity of the malononitrile anion, formed by deprotonation with relatively weak bases and by the two electrophilic cyano groups.

Uses

In organic synthesis.

109-77-3 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (A15046)  Malononitrile, 99%    109-77-3 5g 111.0CNY Detail
Alfa Aesar (A15046)  Malononitrile, 99%    109-77-3 100g 156.0CNY Detail
Alfa Aesar (A15046)  Malononitrile, 99%    109-77-3 500g 612.0CNY Detail
Alfa Aesar (A15046)  Malononitrile, 99%    109-77-3 2500g 2543.0CNY Detail

109-77-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name malononitrile

1.2 Other means of identification

Product number -
Other names Propanedinitrile

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
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:109-77-3 SDS

109-77-3Synthetic route

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

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

Benzylidenemalononitrile
2700-22-3

Benzylidenemalononitrile

A

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

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

B

Benzylmalononitrile
1867-37-4

Benzylmalononitrile

C

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
In propan-1-ol for 2h; Heating;A 90%
B 97%
C 90%
6-hydrazino-1,3-dimethyl-1H-pyrimidine-2,4-dione
123506-40-1

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

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

2-cyano-3-phenylacrylamide

A

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

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

B

Benzylmalononitrile
1867-37-4

Benzylmalononitrile

C

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
In propan-1-ol for 2h; Heating;A 90%
B 97%
C 90%
6-hydrazino-1,3-dimethyl-1H-pyrimidine-2,4-dione
123506-40-1

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

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

A

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

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

B

Benzylmalononitrile
1867-37-4

Benzylmalononitrile

C

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
In propan-1-ol for 2h; Heating;A 90%
B 97%
C 90%
sodium cyanide
773837-37-9

sodium cyanide

1,2-dibromomethane
74-95-3

1,2-dibromomethane

malononitrile
109-77-3

malononitrile

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

potassium cyanide

1,2-dibromomethane
74-95-3

1,2-dibromomethane

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
With potassium iodide at 160℃; for 8h; Sealed tube; Inert atmosphere;95.01%
3-(Chloromethyl)-2-benzoxazolinethione
55042-38-1

3-(Chloromethyl)-2-benzoxazolinethione

potassium cyanide
151-50-8

potassium cyanide

A

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

3-<(2-Benzoxazolyl)thiomethyl>-2(3H)-benzoxazolethione

B

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
In acetone for 24h; Product distribution; Mechanism; Heating;A 95%
B n/a
cyanoacetic acid amide
107-91-5

cyanoacetic acid amide

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
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 water76%
phosgene
75-44-5

phosgene

cyanoacetic acid amide
107-91-5

cyanoacetic acid amide

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
With pyridine In 1,2-dichloro-ethane at 75℃; for 15h; Reagent/catalyst; Solvent; Temperature;94%
3-chloromethyl-3H-benzothiazole-2-thione
41526-42-5

3-chloromethyl-3H-benzothiazole-2-thione

potassium cyanide
151-50-8

potassium cyanide

A

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

3-<(2-Benzothiazolyl)thiomethyl>-2(3H)-benzothiazolethione

B

malononitrile
109-77-3

malononitrile

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

potassium cyanide

dichloromethane
75-09-2

dichloromethane

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
With potassium iodide at 155℃; for 12h; Sealed tube; Inert atmosphere;91.04%
2-(N-morpholinyl)methyl-4-nitrophenol
69245-79-0

2-(N-morpholinyl)methyl-4-nitrophenol

A

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

4-amino-2-morpholinomethylphenol

B

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
With hydrazine hydrateA 91%
B 52%
hydrogen cyanide
74-90-8

hydrogen cyanide

chloroacetonitrile
107-14-2

chloroacetonitrile

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
at 160℃; Temperature; Inert atmosphere;89.53%
sodium cyanide
773837-37-9

sodium cyanide

dichloromethane
75-09-2

dichloromethane

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
With aluminum (III) chloride; tetrabutylammomium bromide at 90℃; for 8h; Reagent/catalyst;89%
malonodiamide
108-13-4

malonodiamide

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
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;
bromomalononitrile
1885-22-9

bromomalononitrile

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
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;
1,3,5-trichloro-2,4,6-triazine
108-77-0

1,3,5-trichloro-2,4,6-triazine

cyanoacetic acid amide
107-91-5

cyanoacetic acid amide

A

isocyanuric acid
108-80-5

isocyanuric acid

B

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
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%
octyl 2-cyanoacetate
15666-97-4

octyl 2-cyanoacetate

ethenetetracarbonitrile
670-54-2

ethenetetracarbonitrile

A

n-Octyl tricyanoacrylate

n-Octyl tricyanoacrylate

B

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
With pyridine In tetrahydrofuran at 65℃; for 0.75h;A 63%
B n/a
1,3,5-trichloro-2,4,6-triazine
108-77-0

1,3,5-trichloro-2,4,6-triazine

cyanoacetic acid amide
107-91-5

cyanoacetic acid amide

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
N,N-dimethyl-formamide In ethyl acetate at 50 - 60℃; for 11 - 12h;52%
benzyl 2-cyanoacetate
14447-18-8

benzyl 2-cyanoacetate

ethenetetracarbonitrile
670-54-2

ethenetetracarbonitrile

A

Benzyl tricyanoacrylate

Benzyl tricyanoacrylate

B

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
With pyridine In tetrahydrofuran at 65℃; for 0.75h;A 48%
B n/a
aniline hydroiodide
45497-73-2

aniline hydroiodide

Hexacyanocyclopropane
139952-06-0

Hexacyanocyclopropane

A

anilino-ethenetricarbonitrile
41996-49-0

anilino-ethenetricarbonitrile

B

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
In ethyl acetate at 40℃; Mechanism; other amine hydroiodides, reaction time 3-5 min;A 46%
B n/a
cyanoacetic acid tert-butyl ester
1116-98-9

cyanoacetic acid tert-butyl ester

ethenetetracarbonitrile
670-54-2

ethenetetracarbonitrile

A

tert-butyl tricyanoethylenecarboxylate
833447-41-9

tert-butyl tricyanoethylenecarboxylate

B

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
With pyridine In tetrahydrofuran for 40h; Michael addition; Reflux;A 41%
B n/a
cyanoacetic acid n-propyl ester
14447-15-5

cyanoacetic acid n-propyl ester

ethenetetracarbonitrile
670-54-2

ethenetetracarbonitrile

A

n-Propyl tricyanoacrylate

n-Propyl tricyanoacrylate

B

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
With pyridine In tetrahydrofuran at 65℃; for 0.75h;A 38%
B n/a
allyl cyanoacetate
13361-32-5

allyl cyanoacetate

ethenetetracarbonitrile
670-54-2

ethenetetracarbonitrile

A

allyl tricyanoethylenecarboxylate
1142329-69-8

allyl tricyanoethylenecarboxylate

B

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
With pyridine In tetrahydrofuran for 40h; Michael addition; Reflux;A 26%
B n/a
9-Cyano-10-methyl-10-thiaanthracene
59181-71-4

9-Cyano-10-methyl-10-thiaanthracene

ethenetetracarbonitrile
670-54-2

ethenetetracarbonitrile

A

9-Cyano-9-methylthioxanthene
59181-21-4

9-Cyano-9-methylthioxanthene

B

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

9-Cyano-9-(dicyanomethyl)thioxanthene

C

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

thio-xanthene-9-one

D

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

2,2,3,3-Tetracyanobutane

E

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
In tetrahydrofuran Mechanism;A 8.5%
B 11%
C 13%
D 24%
E 120 mg
ethenetetracarbonitrile
670-54-2

ethenetetracarbonitrile

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

A

ethyl tricyanoethylenecarboxylate
153814-39-2

ethyl tricyanoethylenecarboxylate

B

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
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
ethenetetracarbonitrile
670-54-2

ethenetetracarbonitrile

methyl 2-cyanoacetate
105-34-0

methyl 2-cyanoacetate

A

methyl tricyanoethylenecarboxylate
101342-43-2

methyl tricyanoethylenecarboxylate

B

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
With pyridine In tetrahydrofuran for 40h; Michael addition; Reflux;A 4%
B n/a
acrylonitrile
107-13-1

acrylonitrile

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
durch Copolymerisation(Herstellung);
acetonitrile
75-05-8

acetonitrile

cyanogen chloride
506-77-4

cyanogen chloride

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
With carbon dioxide at 650℃;
(phenylsulfonyl)phosphorimidic trichloride
5666-55-7

(phenylsulfonyl)phosphorimidic trichloride

malonoyl dichloride
1663-67-8

malonoyl dichloride

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
at 130℃;
furfural
98-01-1

furfural

malononitrile
109-77-3

malononitrile

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

2-cyano-3-(2-furanyl)acrylonitrile

Conditions
ConditionsYield
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%
piperonal
120-57-0

piperonal

malononitrile
109-77-3

malononitrile

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

2-benzo[1,3]dioxol-5-ylmethylene-malononitrile

Conditions
ConditionsYield
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%
cyclohexanone
108-94-1

cyclohexanone

malononitrile
109-77-3

malononitrile

2-(cyclohexylidene)malononitrile
4354-73-8

2-(cyclohexylidene)malononitrile

Conditions
ConditionsYield
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%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

malononitrile
109-77-3

malononitrile

4-chlorobenzylidenemalonodinitrile
1867-38-5

4-chlorobenzylidenemalonodinitrile

Conditions
ConditionsYield
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%
2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

malononitrile
109-77-3

malononitrile

o-chlorobenzylidene malononitrile
2698-41-1

o-chlorobenzylidene malononitrile

Conditions
ConditionsYield
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%
1-naphthaldehyde
66-77-3

1-naphthaldehyde

malononitrile
109-77-3

malononitrile

(1-naphthylmethylidene)malononitrile
2972-83-0

(1-naphthylmethylidene)malononitrile

Conditions
ConditionsYield
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%
3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

malononitrile
109-77-3

malononitrile

3-nitrobenzylidenemalononitrile
2826-32-6

3-nitrobenzylidenemalononitrile

Conditions
ConditionsYield
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%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

malononitrile
109-77-3

malononitrile

4-Nitrobenzylidenemalononitrile
2700-23-4

4-Nitrobenzylidenemalononitrile

Conditions
ConditionsYield
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%
benzaldehyde
100-52-7

benzaldehyde

malononitrile
109-77-3

malononitrile

Benzylidenemalononitrile
2700-22-3

Benzylidenemalononitrile

Conditions
ConditionsYield
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%
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

malononitrile
109-77-3

malononitrile

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

2-(4-hydroxyphenylmethylene)malononitrile

Conditions
ConditionsYield
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%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

malononitrile
109-77-3

malononitrile

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

2-(4-methoxyphenylmethylene)malononitrile

Conditions
ConditionsYield
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%
vanillin
121-33-5

vanillin

malononitrile
109-77-3

malononitrile

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

2-(4-hydroxy-3-methoxybenzylidene)malononitrile

Conditions
ConditionsYield
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%
3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

malononitrile
109-77-3

malononitrile

3,4-dimethoxybenzylidenemalononitrile
2972-80-7

3,4-dimethoxybenzylidenemalononitrile

Conditions
ConditionsYield
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%
acrylonitrile
107-13-1

acrylonitrile

malononitrile
109-77-3

malononitrile

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

4,4-dicyano-heptanedinitrile

Conditions
ConditionsYield
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%
acetophenone
98-86-2

acetophenone

malononitrile
109-77-3

malononitrile

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

2-(1-phenylethylidene)propanedinitrile

Conditions
ConditionsYield
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%
ortho-anisaldehyde
135-02-4

ortho-anisaldehyde

malononitrile
109-77-3

malononitrile

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

2-(2-methoxybenzylidene)malononitrile

Conditions
ConditionsYield
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%
4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

malononitrile
109-77-3

malononitrile

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

p-(N-dimethylamino benzylidene) malononitrile

Conditions
ConditionsYield
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%
3,4-dihydronaphthalene-1(2H)-one
529-34-0

3,4-dihydronaphthalene-1(2H)-one

malononitrile
109-77-3

malononitrile

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

1,2,3,4-tetrahydro-1-naphthylidene malononitrile

Conditions
ConditionsYield
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%
2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

malononitrile
109-77-3

malononitrile

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

2-(2-nitrobenzylidene)malononitrile

Conditions
ConditionsYield
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%
Benzophenone imine
1013-88-3

Benzophenone imine

malononitrile
109-77-3

malononitrile

2-(diphenylmethylene)malononitrile
10394-96-4

2-(diphenylmethylene)malononitrile

Conditions
ConditionsYield
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%
m-bromobenzoic aldehyde
3132-99-8

m-bromobenzoic aldehyde

malononitrile
109-77-3

malononitrile

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

2-(3-bromobenzylidene)malononitrile

Conditions
ConditionsYield
With glycine In dichloromethane100%
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%
9-fluorenone
486-25-9

9-fluorenone

malononitrile
109-77-3

malononitrile

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

2-fluoren-9-ylidene-malononitrile

Conditions
ConditionsYield
for 0.0833333h; Inert atmosphere; Neat (no solvent);100%
With piperidine In ethanol at 20℃; for 0.5h; Knoevenagel condensation;87%
With ethanol; ammonia
malononitrile
109-77-3

malononitrile

cyanogen chloride
506-77-4

cyanogen chloride

sodium tricyanomethanide
36603-80-2

sodium tricyanomethanide

Conditions
ConditionsYield
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
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

malononitrile
109-77-3

malononitrile

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

2-(4-methylbenzylidene)malononitrile

Conditions
ConditionsYield
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-)*2C27H18N6*3Ni(2+)*15H2O*5C2H6O In dichloromethane at 60℃; for 2h; Knoevenagel Condensation; Inert atmosphere;100%
benzyl bromide
100-39-0

benzyl bromide

malononitrile
109-77-3

malononitrile

2,2-dibenzylmalononitrile
3779-31-5

2,2-dibenzylmalononitrile

Conditions
ConditionsYield
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%
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

malononitrile
109-77-3

malononitrile

4-fluorobenzylidenemalononitrile
2826-22-4

4-fluorobenzylidenemalononitrile

Conditions
ConditionsYield
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-)*2C27H18N6*3Ni(2+)*15H2O*5C2H6O 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%
benzil
134-81-6

benzil

malononitrile
109-77-3

malononitrile

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

2-(2-oxo-1,2-diphenylethylidene)malononitrile

Conditions
ConditionsYield
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;
4-methoxycinnamaldehyde
1963-36-6

4-methoxycinnamaldehyde

malononitrile
109-77-3

malononitrile

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

4-(4-methoxyphenyl)-1,1-dicyano-1,3-butadiene

Conditions
ConditionsYield
With L-arginine at 20℃; for 0.0666667h; Knoevenagel condensation; Ionic liquid;100%
With piperidine
Knoevenagel Condensation; Alkaline conditions;
dipentyl ketone
927-49-1

dipentyl ketone

malononitrile
109-77-3

malononitrile

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

2-(1-pentyl-hexylidene)-malononitrile

Conditions
ConditionsYield
100%
With 5% active carbon-supported ruthenium In ethanol at 78℃; for 18h;94.7%
With ammonium acetate; acetic acid
carbon disulfide
75-15-0

carbon disulfide

malononitrile
109-77-3

malononitrile

methyl iodide
74-88-4

methyl iodide

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

[Bis(methylthio)methylene]malononitrile

Conditions
ConditionsYield
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%

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