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Malononitrile is a versatile chemical reagent widely used in organic synthesis, particularly in multicomponent reactions such as Knoevenagel condensations, Friedl?nder syntheses, and the preparation of heterocyclic compounds like pyrano[2,3-d]pyrimidines, quinolines, and 4H-pyran derivatives. It serves as an active methylene compound, enabling the formation of α,β-unsaturated nitriles, as well as acting as a precursor for nonlinear optical chromophores and pharmaceutical intermediates. Its applications extend to catalysis, green chemistry, and the development of bioactive molecules, including antimicrobial and enzyme-inhibiting agents. Malononitrile's reactivity and compatibility with various catalysts and reaction conditions make it valuable in both academic and industrial research.

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  • 109-77-3 Structure
  • Basic information

    1. Product Name: Malononitrile
    2. Synonyms: AKOS BBS-00004370;METHYLENE DICYANIDE;METHYLENE CYANIDE;MALONODINITRILE;MALONITRILE;MALONONITRILE;MALONIC ACID DINITRILE;MDN
    3. CAS NO:109-77-3
    4. Molecular Formula: C3H2N2
    5. Molecular Weight: 66.06
    6. EINECS: 203-703-2
    7. Product Categories: Dinitriles;Dinitriles & Trinitriles;Agrochemicals;Pharmaceutical intermediates
    8. Mol File: 109-77-3.mol
  • Chemical Properties

    1. Melting Point: 30-32 °C(lit.)
    2. Boiling Point: 220 °C(lit.)
    3. Flash Point: 234 °F
    4. Appearance: White to yellow-brown/Crystalline Low Melting Mass
    5. Density: 1.049 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.125mmHg at 25°C
    7. Refractive Index: 1.4150
    8. Storage Temp.: 2-8°C
    9. Solubility: 133g/l
    10. PKA: 11(at 25℃)
    11. Water Solubility: 13.3 g/100 mL (20 ºC)
    12. Merck: 14,5711
    13. BRN: 773697
    14. CAS DataBase Reference: Malononitrile(CAS DataBase Reference)
    15. NIST Chemistry Reference: Malononitrile(109-77-3)
    16. EPA Substance Registry System: Malononitrile(109-77-3)
  • Safety Data

    1. Hazard Codes: T,N
    2. Statements: 23/24/25-50/53
    3. Safety Statements: 23-27-45-60-61
    4. RIDADR: UN 2647 6.1/PG 2
    5. WGK Germany: 3
    6. RTECS: OO3150000
    7. F: 8
    8. TSCA: Yes
    9. HazardClass: 6.1
    10. PackingGroup: II
    11. Hazardous Substances Data: 109-77-3(Hazardous Substances Data)

109-77-3 Usage

Chemical Description

Malononitrile is a compound with the formula CH2(CN)2.

Chemical Description

Malononitrile is a versatile reagent used in organic synthesis, while the other three chemicals are derivatives synthesized and studied in the article.

Chemical Description

Malononitrile is a versatile reagent used in organic synthesis.

Check Digit Verification of cas no

The CAS Registry Mumber 109-77-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 9 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 109-77:
(5*1)+(4*0)+(3*9)+(2*7)+(1*7)=53
53 % 10 = 3
So 109-77-3 is a valid CAS Registry Number.

109-77-3 Well-known Company Product Price

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  • 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%

109-77-3Relevant articles and documents

Infrared Spectrum of Matrix-Isolated Hexamethylenetetramine in Ar and H2O at Cryogenic Temperatures

Bernstein, Max P.,Sanford, Scott A.,Allamandola, Louis J.,Chang, Sherwood

, p. 12206 - 12210 (1994)

The infrared spectra of hexamethylenetetramine (HMT) isolated in an argon matrix at 12 K, frozen in H2O at temperatures from 12 to 200 K, and as a pure solid, are reported.The results of ultraviolet photolysis of matrix-isolated HMT and HMT frozen in H2O ice are also presented, and implications for infrared astronomy and astrochemistry are discussed.Furthermore, a simple technique for incorporating large nonvolatile organic molecules into a matrix is described.

Cyanocarbon Acids: Direct Evidence That Their Ionization Is Not an Encounter-Controlled Process and Rationalization of the Unusual Solvent Isotope Effects

Hojatti, M.,Kresge, A. J.,Wang, W.-H.

, p. 4023 - 4028 (1987)

The rate of exchange of the acidic hydrogen of tert-butylmalononitrile was examined by using as a tracer, and the process was found not to be inhibited by hydronium ions in dilute aqueous hydrochloric acid solutions.This rules out the Swain-Grunwald mechanism for this reaction under these conditions.The bromination of malonitrile was investigated under conditions where reprotonation of the dicyanomethyl carbanion and its reaction with bromine occur at comparable rates, and the bromination reaction was found to have a specific rate twice that for reprotonation.Reprotonation therefore cannot be a diffusion-controlled process, and malonitrile is not a "normal" acid.The unusually large solvent kinetic isotope effects found for these cyanocarbon acid ionization reactions are explained by postulating that the transferring hydrogen and its positive charge are becoming associated with a solvent cluster rather than with a single water molecule.The thermodynamic acidity constant of malonitrile was determined to be 11.41 in aqueous solution at 25 deg C.

Hydrolysis study of fluoroorganic and cyano-based ionic liquid anions - Consequences for operational safety and environmental stability

Steudte, Stephanie,Neumann, Jennifer,Bottin-Weber, Ulrike,Diedenhofen, Michael,Arning, Juergen,Stepnowski, Piotr,Stolte, Stefan

, p. 2474 - 2483 (2012)

The hydrolytic stability of ionic liquid anions is a key property with regard to their technical applicability and environmental stability. From a technical point of view hydrolytic processes may lead to reduced durability, diminished technical performance and reduced operational safety in that corrosive and/or toxic hydrolysis products are formed. On the other hand, susceptibility to hydrolytic processes is advantageous where environmental stability and persistency are concerned, since hydrolysis is the most important abiotic degradation pathway in the environment. We investigated the hydrolytic stability of the most common ionic liquid anions, dicyanimide [N(CN) 2]-, tricyanmethanide [C(CN)3]-, tetracyanidoboranate [B(CN)4]-, bis(trifluoromethylsulphonyl)imide [(CF3SO2) 2N]-, trifluorotris(pentafluoroethyl)phosphate [(C 2F5)3PF3]- and 1,1,2,2-tetrafluoroethanesulphonic acid [H(C2F4)SO 3]-, as a function of pH (1, 7, 9 and 13) and temperature. The results show that there was no difference in hydrolytic stability as recorded for 1-ethyl-3-methylimidazolium (IM12) or for the alkali cations. All the anions were stable under neutral and slightly basic conditions (half-lives at 25 °C ?1 year). In strongly acidic and basic solutions, however, B(CN)4-, (CF3SO2)2N -, (C2F5)3PF3- and H(C2F4)SO3- were hydrolytically stable, whereas N(CN)2- and C(CN)3- were not. The kinetics of hydrolysis were recorded and Arrhenius plots were generated for the latter two anions. In addition, their hydrolysis pathways and the resulting products were identified via mass spectrometry. The cytotoxicity of hydrolysed IL solutions towards the mammalian cell line IPC-81 and the identified hydrolysis products (pure compounds) was investigated for a first estimate of their toxicological properties.

Preparation method of malononitrile and malononitrile prepared by preparation method

-

Paragraph 0056-0103, (2021/05/01)

The invention relates to the technical field of chemical synthesis methods, particularly to a malononitrile preparation method and malononitrile prepared thereof. The malononitrile preparation method comprises the following steps: mixing cyanoacetamide, a catalyst and a solvent, heating, refluxing, and introducing phosgene to synthesize malononitrile, wherein the mass ratio of the cyanoacetamide to the catalyst to the solvent is (2.5-3.5):(0.005-0.02):(7.5-10.5), the solvent is any one of dichloromethane, dichloroethane or methylbenzene, and the catalyst is any one or more of diethylamine, N,N-dimethylformamide or pyridine. According to the invention, cyanoacetamide is adopted to synthesize malononitrile in one step under the action of phosgene, wherein the required raw materials are cheap and easy to obtain, the synthetic reaction steps are few, harsh conditions are avoided, the operation is simple, stable and good in controllability, and the yield of the prepared malononitrile can reach 93% or above and is far higher than that of malononitrile obtained through other process schemes; and the preparation method is low in three-waste treatment cost, and has objective economic benefit.

Malononitrile preparation method and malononitrile prepared thereof

-

Paragraph 0056-0095; 0103, (2020/08/02)

The invention relates to the technical field of chemical synthesis methods, in particular to a malononitrile preparation method and malononitrile prepared thereof. The malononitrile preparation methodcomprises the following steps that cyanoacetamide, a catalyst and a solvent are mixed, heated, refluxed and introduced with phosgene, and malononitrile is synthesized, wherein the mass ratio of the cyanoacetamide to the catalyst to the solvent is (2.5-3.5):(0.005-0.02):(7.5 to 10.5); the solvent is any one of dichloromethane, dichloroethane or methylbenzene; and the catalyst is any one or more ofdiethylamine, N, N-dimethylformamide or pyridine. According to the invention, cyanoacetamide is adopted to synthesize malononitrile in one step under the action of phosgene; the method has the advantages of cheap and easily available required raw materials, few synthesis reaction steps, no harsh conditions, simple operation, stability and good controllability, the yield of the prepared malononitrile can reach 93% or above and is far higher than that of other process schemes, and the preparation method has the advantages of low three-waste treatment cost and objective economic benefits.

Preparation method of malononitrile

-

Paragraph 0044-0051, (2020/07/24)

The invention discloses a preparation method of an important organic synthesis raw material malononitrile, which comprises the following steps: performing a reaction on chloroacetonitrile and hydrogencyanide as raw materials in a tubular reactor, and separating the reaction product by condensation and negative pressure distillation to obtain the malononitrile. The method has the advantages of mild reaction conditions, simple separation and purification process, high product yield and purity, energy saving, environmental protection and low cost.

Synthetic method of malononitrile

-

Paragraph 0011-0030, (2020/01/08)

The invention belongs to the technical field of organic synthesis, and provides a malononitrile synthesis method. The synthetic method comprises the following steps: adding dichloromethane and sodiumcyanide into a reaction kettle at a molar ratio of (1: 1)-(3: 1), slowly adding a catalyst into the reaction kettle under stirring and heating conditions, controlling the temperature in the reaction kettle to be 90 DEG C, and carrying out thermal preservation reaction for 5-9 hours after feeding is finished; after the reaction is finished, adding deionized water into an obtained reaction product to wash an organic phase for a plurality of times, separating out the organic phase, drying the organic phase, and rectifying to obtain malononitrile; wherein the catalyst is a composition of aluminumtrichloride and tetrabutylammonium bromide. According to the method, the malononitrile product is directly synthesized by taking cheap dichloromethane as a raw material through a one-step method, theprocess route is simple, and the cost is low.

Synthesis method of malononitrile

-

Paragraph 0038-0041, (2019/02/06)

The invention discloses a synthesis method of malononitrile. Metal hydride and dihalomethane are used as an initial reactant system; under the existence of metal iodate catalysts, a dipolar aprotic solvent is used as a reaction auxiliary agent to prepare a target product of malononitrile. The method has the advantages that through the addition of the reaction auxiliary agent for reaction promotion, the malononitrile hydrolysis or alcoholysis due to polar solvents of water, alcohol and the like can be avoided; high yield and high quality of malononitrile are ensured; the malononitrile with theyield higher than 91.0 percent and the purity higher than 99.3 percent can be obtained.

Synthesis method of malononitrile

-

Paragraph 0029; 0030; 0031; 0032; 0033; 0034; 0035-0053, (2018/05/16)

The invention relates to the technical field of malononitrile synthesis, and particularly discloses a synthesis method of malononitrile. The synthesis method of the malononitrile comprises the following steps: performing mixing treatment on a solvent, cyanoacetamide, phosphoryl chloride and solid phosgene to obtain suspension, heating to 50 to 90 DEG C, and performing heat-preservation reaction toobtain a malononitrile solution; performing heating distillation treatment on the malononitrile solution, recycling the solvent and the phosphoryl chloride to obtain a distillation residue; performing vacuum reduced pressure distillation treatment on the distillation residue to obtain the malononitrile. The synthesis method of the malononitrile has the advantages of simple process, convenient operation and low cost; the phosphoryl chloride and the solid phosgene are adopted as a mixed dehydrating agent, so that the yield and the quality of a product are greatly improved, and production of solid wastes is avoided.

Corresponding amine nitrile and method of manufacturing thereof (by machine translation)

-

Paragraph 0136; 0137; 0140, (2018/07/15)

The present invention relates to a nitrile manufacturing method, which has characteristics of significantly-reduced ammonia source consumption, low environmental pressure, low energy consumption, low production cost, high nitrile purity, high nitrile yield and the like compared with the method in the prior art, wherein nitrile having a complicated structure can be obtained through the method. The present invention further relates to a method for producing a corresponding amine from the nitrile.

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