2-Propenenitrile,3-(dimethylamino)- supplier

Name
3-(DIMETHYLAMINO)ACRYLONITRILE
EINECS 219-305-7
CAS No. 2407-68-3
Article Data26
CAS DataBase
Density 0.912 g/cm³
Solubility
Melting Point
Formula C₅H₈N₂
Boiling Point 277.6 °C at 760 mmHg
Molecular Weight 96.1319
Flash Point 131.9 °C
Transport Information
Appearance clear yellow liquid
Safety 26-36
Risk Codes 22-36/37/38
Molecular Structure
Hazard Symbols Xn
Synonyms Acrylonitrile,3-(dimethylamino)- (7CI,8CI);3-(Dimethylamino)acrylonitrile;NSC 127942;b-(Dimethylamino)acrylonitrile;
PSA 27.03000
LogP 0.58528

Synthetic route

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 372-09-8
cyanoacetic acid

: 2407-68-3
3-dimethylaminoacrylonitrile

Conditions

Conditions	Yield
In 1,4-dioxane at 80℃; for 2h;	100%
In 1,4-dioxane at 20 - 90℃; for 16h;

: 21511-55-7, 34643-89-5
(methoxymethylidene)dimethylammonium methyl sulfate

: 1071-36-9
sodium cyanoacetate

: 2407-68-3
3-dimethylaminoacrylonitrile

Conditions

Conditions	Yield
In ethanol at 30℃; for 10h; Temperature; Solvent;	97.4%

: 1070-71-9
propiolonitrile

: 124-40-3
dimethyl amine

: 2407-68-3
3-dimethylaminoacrylonitrile

Conditions

Conditions	Yield
In water at 20℃; for 20h;	94%

: 34644-27-4
2-dimethylamino-2-ethoxy-1-cyanoethylene

: 2407-68-3
3-dimethylaminoacrylonitrile

Conditions

Conditions	Yield
With platinum on carbon; hydrogen In ethanol at 50℃; under 30003 Torr; for 16h; Autoclave;	65%
With platinum on carbon; hydrogen

: 372-09-8
cyanoacetic acid

: 2-aza-1,3-bis(dimethylamino)-3-methoxy-1-propen

A: 2407-68-3
3-dimethylaminoacrylonitrile

B: 4-aza-5-dimethylamino-2,4-pentadienenitrile

Conditions

Conditions	Yield
In benzene 80 deg C, then 105 deg C, 2 h;	A n/a B 8%
In benzene 80 deg C, then 105 deg C, 2 h; Title compound not separated from byproducts;

...Expand

: 3721-37-7
cis-β-chloroacrylonitrile

: 124-40-3
dimethyl amine

: 2407-68-3
3-dimethylaminoacrylonitrile

Conditions

Conditions	Yield

: 2-aza-1,3-bis(dimethylamino)-3-methoxy-1-propen

: 75-05-8
acetonitrile

A: 2407-68-3
3-dimethylaminoacrylonitrile

B: 4-aza-5-dimethylamino-2,4-pentadienenitrile

Conditions

Conditions	Yield
for 120h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 73233-19-9
MeCN*HCl

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 2407-68-3
3-dimethylaminoacrylonitrile

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 110℃; for 9h;

: 21511-55-7, 34643-89-5
(methoxymethylidene)dimethylammonium methyl sulfate

: 372-09-8
cyanoacetic acid

: 2407-68-3
3-dimethylaminoacrylonitrile

Conditions

Conditions	Yield
Stage #1: (methoxymethylidene)dimethylammonium methyl sulfate; cyanoacetic acid In ethanol at 5 - 40℃; Stage #2: With sodium hydroxide In water-d2 pH=8; Stage #3: In toluene at 5 - 50℃; Temperature; pH-value; Irradiation;

: 124-40-3
dimethyl amine

: 107-13-1
acrylonitrile

: 2407-68-3
3-dimethylaminoacrylonitrile

Conditions

Conditions	Yield
at 120℃; under 225.023 Torr; Temperature; Pressure; Cooling with ice;

: 354-32-5
trifluoracetyl chloride

: 2407-68-3
3-dimethylaminoacrylonitrile

: 339011-85-7
2-((dimethylamino)methylene)-4,4,4-trifluoro-3-oxobutyronitrile

Conditions

Conditions	Yield
With pyridine In toluene Product distribution / selectivity; Cooling with ice; Inert atmosphere;	99%

: 2407-68-3
3-dimethylaminoacrylonitrile

: C8H15ClN2O3

: C11H15N3O3

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethyl acetate at 20℃;	97%

: 2407-68-3
3-dimethylaminoacrylonitrile

: 312324-17-7
C8H15ClN2O3

: C11H15N3O3

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethyl acetate at 20℃;	96%

: 2407-68-3
3-dimethylaminoacrylonitrile

: 1399716-78-9
(S)-tert-butyl 2-(chloro(hydroxyimino)methyl)pyrrolidine-1-carboxylate

: C13H17N3O3

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethyl acetate at 20℃;	95%

: 2407-68-3
3-dimethylaminoacrylonitrile

: 1222172-49-7
methyl 5-acetamido-2-amino-4-ethoxybenzoate

: 1222172-50-0
methyl 5-acetamido-2-[(2-cyanovinyl)amino]-4-ethoxybenzoate

Conditions

Conditions	Yield
Stage #1: methyl 5-acetamido-2-amino-4-ethoxybenzoate; acetic acid at 20℃; Stage #2: 3-dimethylaminoacrylonitrile at 25 - 30℃; Product distribution / selectivity;	94.8%
With acetic acid at 20℃; for 5h; Large scale;	92%

: 2407-68-3
3-dimethylaminoacrylonitrile

: 76-05-1
trifluoroacetic acid

: 339011-85-7
2-((dimethylamino)methylene)-4,4,4-trifluoro-3-oxobutyronitrile

Conditions

Conditions	Yield
With phosgene; triethylamine In toluene at 5 - 25℃; Product distribution / selectivity;	94%
With triethylamine In toluene at 5℃; for 3h;	92.12%
With oxalyl dichloride; triethylamine; N,N-dimethyl-formamide In toluene at 20℃; Product distribution / selectivity; Cooling with ice;	89%

: 603-76-9
1-methylindole

: 2407-68-3
3-dimethylaminoacrylonitrile

: 3-(dimethylamino)-3-(1-methyl-1H-indol-3-yl)propanenitrile

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 28℃; for 4h; Solvent; Reagent/catalyst;	94%
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 4h; Temperature; Reagent/catalyst; Friedel-Crafts Alkylation;	93%

: 2407-68-3
3-dimethylaminoacrylonitrile

: tert-butyl 3-(chloro(hydroxyimino)methyl)azetidine-1-carboxylate

: C12H15N3O3

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethyl acetate at 20℃;	94%

: 1148049-26-6
tert-butyl (2R)-2-[chloro(hydroxyimino)methyl]pyrrolidine-1-carboxylate

: 2407-68-3
3-dimethylaminoacrylonitrile

: C13H17N3O3

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethyl acetate at 20℃;	93%

: 2407-68-3
3-dimethylaminoacrylonitrile

: 64-19-7
acetic acid

: 885121-98-2
(E/Z)-2-((dimethylamino)methylene)-3-oxobutanenitrile

Conditions

Conditions	Yield
With phosgene; triethylamine In water; toluene at 0 - 20℃; for 3h;	93%

: 2407-68-3
3-dimethylaminoacrylonitrile

: 467423-44-5
tert-butyl 4-(chloro(hydroxyimino)methyl)piperidine-1-carboxylate

: C14H19N3O3

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethyl acetate at 20℃;	92%

: 2407-68-3
3-dimethylaminoacrylonitrile

: 1222172-51-1
ethyl 5-acetamido-2-amino-4-ethoxybenzoate

: 1222172-52-2
ethyl 2-[(2-cyanovinyl)amino]-4-ethoxy-5-acetylamidobenzoate

Conditions

Conditions	Yield
In 1,2-dimethoxyethane at 20℃; for 12h;	89%

: 2407-68-3
3-dimethylaminoacrylonitrile

: 1070970-28-3
C7H13ClN2O3

: C10H13N3O3

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethyl acetate at 20℃;	89%

: 422-64-0
pentafluoropropionic acid

: 2407-68-3
3-dimethylaminoacrylonitrile

: 1037593-83-1
3-dimethylamino-2-(pentafluoroethylcarbonyl)acrylonitrile

Conditions

Conditions	Yield
With phosgene; triethylamine In toluene at 5 - 20℃; Cooling with ice; Inert atmosphere;	88%
With phosgene; triethylamine In toluene at 5 - 20℃; Inert atmosphere; Cooling with ice;	88%

: 2407-68-3
3-dimethylaminoacrylonitrile

: 89-98-5
2-chloro-benzaldehyde

: 4-(2-chlorophenyl)pyridine-3,5-dicarbonitrile

Conditions

Conditions	Yield
With ammonium cerium (IV) nitrate; thioacetamide In dimethyl sulfoxide at 110℃; for 12h;	88%

: 375-22-4
heptafluorobutyric Acid

: 2407-68-3
3-dimethylaminoacrylonitrile

: 1037593-84-2
3-dimethylamino-2-(heptafluoropropylcarbonyl)acrylonitrile

Conditions

Conditions	Yield
With phosgene; triethylamine In toluene at 6 - 20℃; Inert atmosphere; Cooling with ice;	86%
With phosgene; triethylamine In toluene at 6 - 20℃; Cooling with ice; Inert atmosphere;

: 1086400-66-9
(Z)-2-(ethoxymethylene)-4,4-difluoro-3-oxobutanoic acid ethyl ester

: 2407-68-3
3-dimethylaminoacrylonitrile

: 1415089-65-4
ethyl 5-cyano-2-(difluoromethyl)nicotinate

Conditions

Conditions	Yield
Stage #1: (Z)-2-(ethoxymethylene)-4,4-difluoro-3-oxobutanoic acid ethyl ester; 3-dimethylaminoacrylonitrile In N,N-dimethyl-formamide at 60 - 65℃; for 5h; Industry scale; Stage #2: With ammonium acetate In N,N-dimethyl-formamide at 60 - 65℃; for 12h; Industry scale;	85%

: (E/Z)-ethyl 2-(ethoxymethylene)-4,4-difluoro-3-oxobutanoate

: 2407-68-3
3-dimethylaminoacrylonitrile

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 1415089-65-4
ethyl 5-cyano-2-(difluoromethyl)nicotinate

Conditions

Conditions	Yield
Stage #1: (E/Z)-ethyl 2-(ethoxymethylene)-4,4-difluoro-3-oxobutanoate; 3-dimethylaminoacrylonitrile; N,N-dimethyl-formamide at 60 - 65℃; for 5h; Large scale; Stage #2: With ammonium acetate at 60 - 65℃; for 12h; Large scale;	85%

...Expand

: 2407-68-3
3-dimethylaminoacrylonitrile

: 135484-83-2
2-amino-4-bromo-benzoic acid methyl ester

: 4-bromo-2-((2-cyanovinyl)amino)benzoic acid methyl ester

Conditions

Conditions	Yield
In ethyl acetate at 20℃;	85%

: 96-54-8
N-Methylpyrrole

: 2407-68-3
3-dimethylaminoacrylonitrile

: C10H15N3

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 28℃; for 6h; Time; Temperature; Solvent; Reagent/catalyst;	85%

: 381-72-6
difluoroacetyl chloride

: 2407-68-3
3-dimethylaminoacrylonitrile

: 1037593-82-0
2-((dimethylamino)methylene)-4,4-difluoro-3-carbonylbutyronitrile

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 5h; Solvent; Inert atmosphere;	84.6%

: 2407-68-3
3-dimethylaminoacrylonitrile

: 76-04-0
2-chloro-2,2-difluoroacetic acid

: 1037593-81-9
3-dimethylamino-2-(chlorodifluoromethylcarbonyl)acrylonitrile

Conditions

Conditions	Yield
With phosgene; triethylamine In toluene at 5 - 20℃; Cooling with ice; Inert atmosphere;	83%
With phosgene; triethylamine In toluene at 5 - 20℃; Inert atmosphere; Cooling with ice;	83%

: 399-72-4
5-fluoro-2-methyl-1H-indole

: 2407-68-3
3-dimethylaminoacrylonitrile

: (E)-3-(5-fluoro-2-methyl-1H-indol-3-yl)acrylonitrile

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 28℃; for 4h; Reagent/catalyst;	83%

: 13228-39-2
1-ethyl-2-phenyl-1H-indole

: 2407-68-3
3-dimethylaminoacrylonitrile

A: (E)-3-(1-ethyl-2-phenyl-1H-indol-3-yl)acrylonitrile

B: 3-(dimethylamino)-3-(1-ethyl-2-phenyl-1H-indol-3-yl)propanenitrile

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 28℃; for 4h;	A 15% B 83%

...Expand

: 116176-92-2
5-fluoro-1-methyl-1H-indole

: 2407-68-3
3-dimethylaminoacrylonitrile

: 3-(dimethylamino)-3-(5-fluoro-1-methyl-1H-indol-3-yl)propanenitrile

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 28℃; for 4h;	82%

: 603-76-9
1-methylindole

: 2407-68-3
3-dimethylaminoacrylonitrile

: 3,3-bis(1-methyl-1H-indol-3-yl)propanenitrile

Conditions

Conditions	Yield
With dichloro-acetic acid In 1,2-dichloro-ethane at 50℃; for 4h;	82%
With dichloro-acetic acid at 50℃; for 4h; Temperature; Time;	82%

: 95-20-5
2-methyl-1H-indole

: 2407-68-3
3-dimethylaminoacrylonitrile

: (E)-3-(2-methyl-1H-indol-3-yl)acrylonitrile

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 28℃; for 4h; Reagent/catalyst; Time;	82%

2-Propenenitrile,3-(dimethylamino)- Specification

The 2-Propenenitrile,3-(dimethylamino)-, with the CAS registry number 2407-68-3, is also known as N,N-Dimethylaminoacrylonitrile. Its EINECS registry number is 219-305-7. This chemical's molecular formula is C₅H₈N₂ and molecular weight is 96.13042. Its IUPAC name is called (Z)-3-(dimethylamino)prop-2-enenitrile. This chemical is clear yellow liquid.

Physical properties of 2-Propenenitrile,3-(dimethylamino)-: (1)ACD/LogP: 0.61; (2)ACD/LogD (pH 5.5): 0.32; (3)ACD/LogD (pH 7.4): 0.61; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1.7; (6)ACD/KOC (pH 5.5): 26.25; (7)ACD/KOC (pH 7.4): 50.64; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 1; (10)Index of Refraction: 1.461; (11)Molar Refractivity: 28.9 cm³; (12)Molar Volume: 105.3 cm³; (13)Surface Tension: 32.9 dyne/cm; (14)Density: 0.912 g/cm³; (15)Flash Point: 131.9 °C; (16)Enthalpy of Vaporization: 51.62 kJ/mol; (17)Boiling Point: 277.6 °C at 760 mmHg; (18)Vapour Pressure: 0.00448 mmHg at 25°C.

Uses of 2-Propenenitrile,3-(dimethylamino)-: it can be used to produce 2-dimethylamino-2H-chromene-3-carbonitrile by heating. This reaction will need reagent p-Toluenesulfonic acid and solvent toluene with reaction time of 15 hours. The yield is about 50%.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause damage to health. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CN(C)C=CC#N
(2)Isomeric SMILES: CN(C)/C=C\C#N
(3)InChI: InChI=1S/C5H8N2/c1-7(2)5-3-4-6/h3,5H,1-2H3/b5-3-
(4)InChIKey: ZKKBIZXAEDFPNL-HYXAFXHYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD50	oral	946mg/kg (946mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 15(Suppl,

Product Name

3-(DIMETHYLAMINO)ACRYLONITRILE

Synthetic route

2-Propenenitrile,3-(dimethylamino)- Specification

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