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2-Cyano-N,N-diethylacetamide

Product Name
2-Cyano-N,N-diethylacetamide
CAS No.
26391-06-0
Chemical Name
2-Cyano-N,N-diethylacetamide
Synonyms
DEFA;N,N-DIETHYLCYANOACETAMIDE;N,N-diethyl caynoacetaMide;2-Cyano-N,N-diethylacetaMid;2-Cyano-N,N-diethylacetamide;N,N-Diethyl-2-cyanoacetoamide;Acetamide, 2-cyano-N,N-diethyl-;2-Cyano-N,N-diethylacetamide >2-Cyano-N,N-diethylacetamide;N,N-Diethyl-2-cyanoacetoamide
CBNumber
CB22130981
Molecular Formula
C7H12N2O
Formula Weight
140.18
MOL File
26391-06-0.mol
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2-Cyano-N,N-diethylacetamide Property

Melting point:
121 °C
Boiling point:
114°C/4mmHg(lit.)
Density 
1.013 g/mL at 25 °C
refractive index 
n20/D1.466
Flash point:
>110℃
storage temp. 
2-8°C
solubility 
Chloroform, Ethyl Acetate, Tetrahydrofuran, Methanol
form 
Oil
pka
4.53±0.10(Predicted)
color 
Light Yellow to Light Brown
InChI
InChI=1S/C7H12N2O/c1-3-9(4-2)7(10)5-6-8/h3-5H2,1-2H3
InChIKey
RYSHIRFTLKZVIH-UHFFFAOYSA-N
SMILES
C(N(CC)CC)(=O)CC#N
CAS DataBase Reference
26391-06-0(CAS DataBase Reference)
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Safety

WGK Germany 
3
HazardClass 
IRRITANT
HS Code 
2926907090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
761133
Product name
N,N-Diethyl-2-cyanoacetoamide
Purity
97%
Packaging
5g
Price
$187
Updated
2025/07/31
Sigma-Aldrich
Product number
761133
Product name
N,N-Diethyl-2-cyanoacetoamide
Purity
97%
Packaging
25g
Price
$913
Updated
2025/07/31
TCI Chemical
Product number
C2822
Product name
2-Cyano-N,N-diethylacetamide
Purity
>98.0%(GC)
Packaging
5g
Price
$67
Updated
2025/07/31
TCI Chemical
Product number
C2822
Product name
2-Cyano-N,N-diethylacetamide
Purity
>98.0%(GC)
Packaging
25g
Price
$168
Updated
2021/12/16
TRC
Product number
D444140
Product name
N,N-Diethylcyanoacetamide
Packaging
2g
Price
$70
Updated
2021/12/16
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2-Cyano-N,N-diethylacetamide Chemical Properties,Usage,Production

Chemical Properties

Pale Brown Oil

Uses

N,N-Diethyl-2-cyanoacetoamide can be used:

  • To prepare N,N-diethyl 2-cyano-2-fluoro-2-phenylthioacetoamide, which is further used in the synthesis of various cyanofluoroamides.
  • In the synthesis of entacapone, a catechol-O-methyltransferase inhibitor by reacting with 3,4-dihydroxy-5-nitrobenzaldehyde.
  • As a building block in the synthesis of fluorophores, applicable as endoplasmic reticulum probes.

Definition

ChEBI: N,N-diethylcyanoacetamide is an aliphatic nitrile and a monocarboxylic acid amide.

Synthesis

109-89-7

105-56-6

26391-06-0

(i) Preparation of N1,N1-diethyl-2-cyanoacetamide: 30 L of anhydrous tetrahydrofuran (THF) was added to the reactor under nitrogen protection, followed by diethylamine (1.272 kg, 17.39 mol). A 33% hexane solution of lithium n-hexyl was loaded into a dropping funnel. The reactor was cooled to below -30°C. The hexyl lithium solution was slowly added dropwise to the reactor, keeping the temperature of the reaction mixture below -30°C during the dropwise addition. After the dropwise addition was completed, the reaction mixture was continued to be stirred at -30 °C for 1.5 hours. Meanwhile, ethyl cyanoacetate (0.655 kg, 5.79 mol) was dissolved in THF (2 L) and transferred to another dropping funnel. The ethyl cyanoacetate solution was slowly added dropwise to the reaction mixture at a temperature well below -30°C. After completion of the dropwise addition, the reaction mixture was gradually warmed to room temperature and stirring was continued for 30 minutes. Subsequently, ethanol (0.66 L) was slowly added dropwise to the reaction mixture and stirred overnight at room temperature. The solvent was removed by distillation under reduced pressure and the residue was treated with 10% hydrochloric acid (8 L) and extracted twice with dichloromethane (DCM, 2 x 7 L). The DCM layers were combined and washed with water (2 × 5 L). The DCM solution was dried and evaporated to dryness to afford the brown oily product N1,N1-diethyl-2-cyanoacetamide (755.29 g, 97% yield), which could be used in the subsequent steps without further purification.1H-NMR (200 MHz, CDCl3): δ 1.2 ppm (t, 6H, J = 7Hz), 3.4 ppm (q, 4H, J = 7Hz), 3.55ppm (s, 2H).

References

[1] Patent: US2008/103191, 2008, A1. Location in patent: Page/Page column 17
[2] Australian Journal of Chemistry, 1976, vol. 29, p. 1039 - 1050
[3] Synthetic Communications, 1990, vol. 20, # 20, p. 3235 - 3243
[4] Journal of the Korean Chemical Society, 2012, vol. 56, # 4, p. 459 - 463

2-Cyano-N,N-diethylacetamide Preparation Products And Raw materials

Raw materials

Preparation Products

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2-Cyano-N,N-diethylacetamide Suppliers

Americas 1 Canada 1 China 151 Europe 1 India 44 Japan 2 United Kingdom 2 United States 13 Global 215
HBCChem, Inc.
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View Lastest Price from 2-Cyano-N,N-diethylacetamide manufacturers

Career Henan Chemical Co
Product
2-Cyano-N,N-diethylacetamide 26391-06-0
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
Customized
Release date
2018-08-08

26391-06-0, 2-Cyano-N,N-diethylacetamideRelated Search:

2-Cyanoacetamide Thioacetamide DIACETAMIDE Acetamide N,N-Diethylhydroxylamine N,N-Diethylethylenediamine N,N-Dimethylacetoacetamide Diethylacetamide N,N-Dimethylacetamide 7'-METHYL-5'-OXO-3',5'-DIHYDRO-2'H-SPIRO[[1,3]DIOXOLANE-2,1'-INDOLIZINE]-6'-CARBONITRILE N-CYANOACETYLMORPHOLINE N-CYANOACETYLPYRROLIDINE 1-CYANOACETYLPIPERIDINE ETHYL 2-(6'-CYANO-5'-OXO-3',5'-DIHYDRO-2'H-SPIRO[[1,3]DIOXOLANE-2,1'-INDOLIZINE]-7'-YL)ACETATE 7-METHYL-1,5-DIOXO-1,2,3,5-TETRAHYDRO-INDOLIZINE-6-CARBONITRILE METHYL 6-CYANO-1-HYDROXY-7-METHYL-5-OXO-3,5-DIHYDROINDOLIZINE-2-CARBOXYLATE 6-(4-CHLOROPHENYL)-1-(3,4-DICHLOROBENZYL)-2-OXO-1,2-DIHYDRO-3-PYRIDINECARBONITRILE 2-Cyano-N,N-diethylacetamide

  • N,N-DIETHYLCYANOACETAMIDE
  • 2-Cyano-N,N-diethylacetamide
  • 2-Cyano-N,N-diethylacetaMid
  • N,N-diethyl caynoacetaMide
  • N,N-Diethyl-2-cyanoacetoamide
  • 2-Cyano-<i>N</i>,<i>N</i>-diethylacetamide
  • 2-Cyano-N,N-diethylacetamide &gt
  • Acetamide, 2-cyano-N,N-diethyl-
  • DEFA
  • <i>N</i>,<i>N</i>-Diethyl-2-cyanoacetoamide
  • 26391-06-0
  • Aliphatics
  • Miscellaneous Reagents
  • pharmaceutical intermediates