2-cyanoacetamide

• ChemBase ID: 70633
• Molecular Formular: C3H4N2O
• Molecular Mass: 84.07666
• Monoisotopic Mass: 84.03236276
• SMILES: C(=O)(CC#N)N
• Canonical SMILES: NC(=O)CC#N
• InChI: InChI=1S/C3H4N2O/c4-2-1-3(5)6/h1H2,(H2,5,6)
• InChIKey: DGJMPUGMZIKDRO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-cyanoacetamide
• IUPAC Traditional name: acetamide, 2-cyano-
• Synonyms: 2-Cyanoacetamide; Malonamide nitrile; 3-Nitrilopropionamide; Cyanoacetamide; CYANOACETAMIDE; 氰基乙酰胺

Database IDs

• CAS Number: 107-91-5; 107-95-1
• EC Number: 203-531-8
• MDL Number: MFCD00008024
• Beilstein Number: 878221
• Merck Index: 142688
• PubChem SID: 162036348; 24857071; 24846668
• PubChem CID: 7898
• Chemspider ID: 7610
• Wikipedia Title: Cyanoacetamide

CALCULATED PROPERTIES

• Acid pKa: 8.527349
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.0804565
• LogD (pH = 7.4): -1.106448
• Log P: -1.080111
• Molar Refractivity: 19.7893 cm^3
• Polarizability: 7.3931203 Å^3
• Polar Surface Area: 66.88 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 118-122°C; 119 - 121°C; 119-121 °C(lit.); 120-122 °C
• Boiling Point: 351.2°C
• Flash Point: 215 °C; 215°C(419°F); 419 °F
• Density: 1.163 g/cm^3

Safety Information

• Storage Warning: IRRITANT
• RTECS: AB5950000
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• UN Number: 3439
• German water hazard class: 2
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-36/37/38; 36/37/38; R8 R23/24/25 R36/38 R45
• Safety Statements: 22-26; 26-37; S17 S45
• TSCA Listed: false; 是
• EU Index: Not listed
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3439 6.1/PG 3

Product Information

• Purity: ≥98.0% (GC); 95+%; 98%; 99%
• Grade: purum
• Linear Formula: NCCH2CONH2

DETAILS

MP Biomedicals - 05215892

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 108448

Packaging
100, 500 g in glass bottle

Sigma Aldrich - 28280

Other Notes
Reagent for the analysis of uronic acids by HPLC1; For the spectrofluorimetric determination of catecholamines2

REFERENCES

• Review of utility in heterocyclic synthesis: Heterocycles, 24, 2023 (1986). Reaction with various enones and enals in the presence of KO-t-Bu and oxygen in DMSO provides a one-step route to functionalized 3-cyano-2-pyridones: Tetrahedron Lett., 36, 3307 (1995):
  
• In the absence of oxygen, only Michael addition occurs.