Conditions | Yield |
---|---|
With ammonia | 100% |
With ammonia In tetrahydrofuran; water at 20℃; for 2h; | 93% |
With ammonium hydroxide In tetrahydrofuran at 20℃; for 24h; | 91% |
Conditions | Yield |
---|---|
With ammonia at -25 - -5℃; for 1h; Temperature; | 98.4% |
Stage #1: methyl 2-cyanoacetate With ammonia In methanol at 20℃; Stage #2: With pyrographite In methanol at 50℃; for 2h; |
Conditions | Yield |
---|---|
With water at 110℃; for 6h; | 95% |
With nitrile hydratase from Rhodococcus rhodochrous J1 Y68T/W72Y mutant In aq. phosphate buffer at 35℃; for 4h; pH=7.4; Enzymatic reaction; regioselective reaction; |
Conditions | Yield |
---|---|
With sodium methylate In methanol | 91% |
formamide
methyl 2-cyanoacetate
cyanoacetic acid amide
Conditions | Yield |
---|---|
With potassium tert-butylate for 0.0333333h; microwave irradiation; | 72% |
ethanol
2,4-dicyano-3-isopropyl-glutaric acid diamide
cyanoacetic acid amide
sodium cyanoacetic acid ethyl ester
cyanoacetic acid amide
Conditions | Yield |
---|---|
With tetrachloromethane; ethanol at 100℃; |
cyanoacetic acid
phenol
A
phenyl 2-cyanoacetate
B
cyanoacetic acid amide
Conditions | Yield |
---|---|
at 160℃; |
ethyl 2-cyanoacetate
pentan-3-one
A
4,4-diethyl-2,6-dioxo-piperidine-3,5-dicarbonitrile
B
cyanoacetic acid amide
Conditions | Yield |
---|---|
With ammonia |
ethyl 2-cyanoacetate
cycloheptanone
A
2,4-dioxo-3-aza-spiro[5.6]dodecane-1,5-dicarbonitrile
B
cyanoacetic acid amide
Conditions | Yield |
---|---|
With ammonia |
ASPARAGINE
chloroamine-T
A
toluene-4-sulfonamide
B
cyanoacetic acid amide
Conditions | Yield |
---|---|
With sodium hydroxide; copper(II) In water at 45℃; Rate constant; Kinetics; Mechanism; variation of temperature, variation of concentrations; |
Conditions | Yield |
---|---|
at 27℃; microbial hydrolysis by Acidovorax facilis 72W, ATCC 55746; pH 7.0 (potassium phosphate buffer); | A 83 % Chromat. B n/a |
Conditions | Yield |
---|---|
beim Eindampfen; |
cyanoacetic acid amide
Conditions | Yield |
---|---|
With ammonia; water |
ammonia
ethyl 2-cyanoacetate
cycloheptanone
A
cyanoacetic acid amide
Conditions | Yield |
---|---|
at 0℃; |
tetrachloromethane
ethanol
sodium cyanoacetic acid ethyl ester
A
diethyl 2-amino-1-cyanopropene-1,3-dicarboxylate
B
cyanoacetic acid amide
Conditions | Yield |
---|---|
at 100℃; |
2,4-dicyano-3-isopropyl-glutaric acid diamide
water
cyanoacetic acid amide
Conditions | Yield |
---|---|
With ammonium hydroxide |
Conditions | Yield |
---|---|
With N-Bromosuccinimide In phosphate buffer; N,N-dimethyl-formamide at 20℃; for 0.5h; pH=5; | |
With hydrogenchloride; sode de l'acide trichloroisocyanurique In water for 3h; | |
With N-Bromosuccinimide In aq. phosphate buffer; N,N-dimethyl-formamide at 20℃; pH=5; |
Conditions | Yield |
---|---|
With potassium hydroxide; sodium methylate In water |
Conditions | Yield |
---|---|
for 0.5h; Reflux; |
Conditions | Yield |
---|---|
With nitrile hydratase from Rhodococcus rhodochrous J1 Y68T mutant In aq. phosphate buffer at 35℃; for 4h; pH=7.4; Reagent/catalyst; Enzymatic reaction; regioselective reaction; |
4-dimethylamino-benzaldehyde
cyanoacetic acid amide
(E)-2-cyano-3-[4-(dimethylamino)phenyl]-2-propenamide
Conditions | Yield |
---|---|
With triethylamine at 20℃; for 24h; Knoevenagel condensation; | 100% |
With tetra(n-butyl)ammonium hydroxide In ethanol; water at 20℃; for 0.166667h; Knoevenagel condensation; | 94% |
With Tonsil Actisil FF at 80℃; for 0.333333h; Irradiation; | 55% |
With potassium-exchanged zirconium hydrogen phosphate at 100℃; for 4h; Knoevenagel condensation; | 49% |
With diethylamine |
4-chlorobenzaldehyde
cyanoacetic acid amide
(E)-2-cyano-3-(4-chlorophenyl)-2-propenamide
Conditions | Yield |
---|---|
With triethylamine at 20℃; for 24h; Knoevenagel condensation; | 100% |
With sodium chloride for 0.0222222h; Knoevenagel condensation; Irradiation; | 98% |
for 0.00833333h; Knoevenagel Condensation; Microwave irradiation; stereoselective reaction; | 98% |
Conditions | Yield |
---|---|
With triethylamine at 20℃; for 24h; Knoevenagel condensation; | 100% |
With USY zeolite In benzene for 5h; Heating; | 90% |
With 1-methyl-piperazine In methanol at 20℃; for 20h; Aldol condensation; | 90% |
2,4-dibenzoyl-3-phenyl-1,4-pentadiene
cyanoacetic acid amide
3,5-Dibenzoyl-1-cyano-4-phenyl-cyclohexanecarboxylic acid amide
Conditions | Yield |
---|---|
With potassium hydroxide In pyridine Ambient temperature; | 100% |
(E)-(S)-2-Ethyl-2-methoxymethoxy-5-(3-methoxymethyl-quinolin-2-yl)-5-oxo-pent-3-enoic acid diethylamide
cyanoacetic acid amide
(S)-4-Cyano-2-ethyl-2-methoxymethoxy-3-[2-(3-methoxymethyl-quinolin-2-yl)-2-oxo-ethyl]-pentanedioic acid 5-amide 1-diethylamide
Conditions | Yield |
---|---|
With potassium tert-butylate In dimethyl sulfoxide for 0.5h; Ambient temperature; | 100% |
With potassium tert-butylate In N,N-dimethyl-formamide at 25℃; Yield given; |
cyanoacetic acid amide
Conditions | Yield |
---|---|
With potassium tert-butylate In dimethyl sulfoxide Ambient temperature; | 100% |
cyanoacetic acid amide
Conditions | Yield |
---|---|
With potassium tert-butylate In dimethyl sulfoxide Ambient temperature; | 100% |
cyanoacetic acid amide
Conditions | Yield |
---|---|
With potassium tert-butylate In dimethyl sulfoxide Ambient temperature; | 100% |
(Z)-5a,6,7,9a-Tetrahydro-5a,6-tetramethylene-11-[ethoxycarbonyl(nitro)methylene]naphtho[1',2':4,5]imidazo[1,2-a]pyridine
cyanoacetic acid amide
Conditions | Yield |
---|---|
With sodium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; methylene exchange; | 100% |
2-Aminonicotinaldehyde
cyanoacetic acid amide
2-Amino-1,8-naphthyridine-3-carboxamide
Conditions | Yield |
---|---|
With piperidine at 20℃; for 0.166667h; Friedlander condensation; | 100% |
N-tert-butyloxycarbonylpiperidin-4-one
cyanoacetic acid amide
tert-butyl 2-amino-3-carbamoyl-4,5-dihydrothieno[2,3-c]pyridine-6(7H)-carboxylate
Conditions | Yield |
---|---|
With morpholine; sulfur In ethanol at 20℃; | 100% |
With morpholine; sulfur In ethanol for 4h; Gewald Aminoheterocycles Synthesis; Reflux; Inert atmosphere; | 95% |
With sulfur; diethylamine In ethanol at 20℃; | 93% |
1,4-dithiane-2,5-diol
cyanoacetic acid amide
2-aminothiophene-3-carboxamide
Conditions | Yield |
---|---|
With triethylamine In ethanol at 68℃; for 12h; Gewald Aminoheterocycles Synthesis; Inert atmosphere; | 100% |
With triethylamine In ethanol at 20℃; for 2.08333h; Heating / reflux; | 88% |
Stage #1: 1,4-dithiane-2,5-diol; cyanoacetic acid amide In ethanol at 20℃; for 0.166667h; Stage #2: With N-methylpiperazine-functionalized Polyacrylonitrile Fiber In ethanol for 4h; Gewald Aminoheterocycles Synthesis; Reflux; | 87% |
3-chloro-2-cyclohexenone
cyanoacetic acid amide
2-cyano-2-(3-oxocyclohexa-1-en-1-yl)acetamide
Conditions | Yield |
---|---|
Stage #1: cyanoacetic acid amide With sodium hydride In diethylene glycol dimethyl ether; mineral oil for 0.0833333h; Stage #2: 3-chloro-2-cyclohexenone In diethylene glycol dimethyl ether; mineral oil for 4.5h; | 100% |
Stage #1: cyanoacetic acid amide With sodium hydride In diethylene glycol dimethyl ether at 20℃; for 0.0833333h; Stage #2: 3-chloro-2-cyclohexenone In diethylene glycol dimethyl ether at 20℃; for 4h; Stage #3: With hydrogenchloride In diethylene glycol dimethyl ether; water | 76% |
In methanol; 1,2-dimethoxyethane; water | |
In methanol; 1,2-dimethoxyethane; water | |
Stage #1: cyanoacetic acid amide With sodium hydride In diethylene glycol dimethyl ether for 0.333333h; Stage #2: 3-chloro-2-cyclohexenone In diethylene glycol dimethyl ether for 8h; | 900 mg |
β-formyl-β-nitroenamine
cyanoacetic acid amide
3-carbamoyl-5-nitro-2-propylaminopyridine
Conditions | Yield |
---|---|
With piperidine In tetrahydrofuran at 60℃; for 24h; | 100% |
C13H16N2O2
cyanoacetic acid amide
5-((2,6-dimethylphenyl)diazenyl)-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol at 130℃; for 0.0833333h; Microwave irradiation; | 100% |
C11H11IN2O2
cyanoacetic acid amide
5-((2-iodophenyl)diazenyl)-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol at 130℃; for 0.0833333h; Microwave irradiation; | 100% |
C13H15BrN2O2
cyanoacetic acid amide
5-((4-bromo-2,6-dimethylphenyl)diazenyl)-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol at 130℃; for 0.0833333h; Microwave irradiation; | 100% |
pentane-2,3,4-trione 3-[(2-nitro-phenyl)-hydrazone]
cyanoacetic acid amide
4,6-dimethyl-5-((2-nitrophenyl)diazenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol at 130℃; for 0.0833333h; Microwave irradiation; | 100% |
Conditions | Yield |
---|---|
With piperidine Knoevenagel Condensation; | 100% |
((E)-3-Dimethylamino-2-phenyl-allylidene)-dimethyl-ammonium; perchlorate
cyanoacetic acid amide
1,2-dihydro-2-oxo-5-phenyl-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
Stage #1: cyanoacetic acid amide With sodium ethanolate In ethanol at 20℃; for 0.5h; Stage #2: ((E)-3-Dimethylamino-2-phenyl-allylidene)-dimethyl-ammonium; perchlorate In ethanol at 25℃; for 0.333333h; Mechanism; Time; | 100% |
cyanoacetic acid amide
Conditions | Yield |
---|---|
With triethylamine Reflux; | 100% |
cyanoacetic acid amide
acetylpinacolin
4-tert-butyl-3-cyano-6-methyl-2(1H)-pyridinone
Conditions | Yield |
---|---|
With lipase from Candida cylindracea In water at 40℃; Rate constant; Kinetics; | 99.8% |
With lipase from Candida cylindracea In water at 40℃; | 99.8% |
In water at 40℃; for 96h; lipase from Candida cylindracea; | 14.5% |
benzaldehyde
cyanoacetic acid amide
(E)-2-cyano-3-phenylacrylamide
Conditions | Yield |
---|---|
for 0.00555556h; Knoevenagel Condensation; Microwave irradiation; stereoselective reaction; | 99% |
With ethanol; sodium Ambient temperature; | 98% |
With tellurium tetrachloride at 80℃; for 0.583333h; | 94% |
5,7-diphenyl-1,2,3,4,4a,5-hexahydro-13H-benzo[4,5]imidazo[2,1-j]quinoline
cyanoacetic acid amide
C30H26N4O
Conditions | Yield |
---|---|
With manganese(IV) oxide In acetone for 1h; Ambient temperature; | 99% |
5-(4-ethoxylphenyl)-2,3-dihydro-2,3-furandione
cyanoacetic acid amide
2-Cyano-N-[3-(4-ethoxy-phenyl)-3-oxo-propionyl]-acetamide
Conditions | Yield |
---|---|
In 1,4-dioxane Heating; | 99% |
4-methyl-benzaldehyde
cyanoacetic acid amide
(E)-2-cyano-3-(4-methylphenyl)acrylamide
Conditions | Yield |
---|---|
for 0.00694444h; Knoevenagel Condensation; Microwave irradiation; stereoselective reaction; | 99% |
With ammonium acetate; acetic acid for 0.00833333h; Knoevenagel condensation; Irradiation; | 94% |
With sodium azide In N,N-dimethyl-formamide at 70℃; for 5h; Knoevenagel condensation; | 91% |
With 1-methyl-piperazine In methanol at 20℃; for 20h; Aldol condensation; | 59% |
1,3-diphenyl-propen-3-one
cyanoacetic acid amide
4,6-diphenyl-2-pyridone
Conditions | Yield |
---|---|
With potassium tert-butylate In dimethyl sulfoxide at 90℃; for 4h; | 99% |
Conditions | Yield |
---|---|
In water for 4h; Heating; | 99% |
With sodium bromide at 85℃; for 0.25h; microwave irradiation; | 60% |
Conditions | Yield |
---|---|
In water for 4h; Heating; | 99% |
With sodium bromide at 85℃; for 0.25h; microwave irradiation; | 63% |
Cyanide and its compounds are on the Community Right-To-Know List. Reported in EPA TSCA Inventory.
1.Introduction of 2-Cyanoacetamide
2-Cyanoacetamide , with its CAS number of 107-91-5, is a kind of White or light yellow crystal. It has synonyms of Acetamide,cyano- (7CI);Malonamide nitrile;Propionamide, 3-nitrilo-;Malonic acid, monoamide mononitrile;Kyanacetamid;cyanoiminoaceticacid;Cyanacetamide;amidkyselinykyanoctove;3-Nitrilo-propionamide and 2-cyano-acetamid. 2-Cyanoacetamide should be stored in shady and cool warehouse and commonly used as the intermediates for medicine, dyes and electroplating solution.
2.Properties of 2-Cyanoacetamide
(1) Molecular Weight: 84.08 (2) H bond acceptors: 3 (3) H bond donors: 2
(4) Freely Rotating Bonds: 1 (5) Polar Surface Area: 44.1 Å2 (6) Index of Refraction: 1.45
(7) Molar Refractivity: 19.42 cm3 (8) Molar Volume: 72.2 cm3 (9) Surface Tension: 51.9 dyne/cm
(10) Density: 1.163 g/cm3 (11) Flash Point: 215 °C (12) Enthalpy of Vaporization: 59.59 kJ/mol
(13) Boiling Point: 351.2 °C at 760 mmHg (14) Vapour Pressure: 4.17E-05 mmHg at 25°C
(15) EINECS: 203-531-8 (16) Melting Point: 119-121 °C(lit.)
3.Structure descriptors of 2-Cyanoacetamide
IUPAC Name: 2-cyanoacetamide
InChI: InChI=1S/C3H4N2O/c4-2-1-3(5)6/h1H2,(H2,5,6)
InChIKey: DGJMPUGMZIKDRO-UHFFFAOYSA-N
Canonical SMILES : C(C#N)C(=O)N
4.Safety information of 2-Cyanoacetamide
Hazard Codes: Xn
Risk Statements: 22-36/37/38-20/21/22
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 22-26-28A
S22:Do not breathe dust.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S28:After contact with skin, wash immediately with plenty of soap-suds.
RIDADR: UN 3439 6.1/PG 3
WGK Germany: 2
PackingGroup: III
5.Uses of 2-Cyanoacetamide
The 2-Cyanoacetamide can used for process for producing 2,6-dihydroxy-3,4-dimethlpridine. The process includes reacting 2-cyanoacetamide with sodium methoxide followed by condensation with ethyl 2-methylacetoacetate in methanol to give the sodium salt of 2,6-dihydroxy-4,5-dimethyl-3-pyridinecarbonitrile. The sodium salt of 2,6-dihydroxy-4,5-dimethyl-3-pyridinecarbonitrile is hydrolyzed with hydrobromic acid and decarboxylated to the hydrobromide salt of 2,6-dihydroxy-3,4-dimethylpyridine. The desired 2,6-dihydroxy-3,4-dimethylpyridine is produced from the hydrobromide salt by neutralizing the same with sodium hydroxide.
6.Toxity data of 2-Cyanoacetamide
1. | orl-mus LD50:1680 mg/kg | KHZDAN Khigiena i Zdraveopazvane. 9 (1966),50. | ||
2. | ipr-mus LD50:200 mg/kg | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD691-689 . | ||
3. | scu-gpg LD50:1155 mg/kg | MELAAD Medicina del Lavoro. Industrial Medicine. 47 (1956),192. |
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