Acrylamide

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Acrylamide (or acrylic amide) is an organic compound with the chemical formula CH2=CHC(O)NH2. It is a white odorless solid, soluble in water and several organic solvents. From the chemistry perspective, acrylamide is a vinyl-substituted primary amide (CONH2). It is produced industrially mainly as a precursor to polyacrylamides, which find many uses as water-soluble thickeners and flocculation agents.

Quick facts: Names, Identifiers, Properties, Hazards... ▼
Acrylamide
Acrylamide-2D-skeletal.png
Acrylamide-MW-2000-3D-balls.png
Names
Preferred IUPAC name
Prop-2-enamide[1]
Other names
Acrylamide
Acrylic amide[2]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.067 OOjs_UI_icon_edit-ltr-progressive.svg
KEGG
UNII
  • InChI=1S/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5) Yes_check.svgY
    Key: HRPVXLWXLXDGHG-UHFFFAOYSA-N Yes_check.svgY
  • InChI=1/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5)
    Key: HRPVXLWXLXDGHG-UHFFFAOYAS
  • O=C(C=C)N
  • C=CC(=O)N
Properties
C3H5NO
Molar mass 71.079 g·mol−1
Appearance white crystalline solid, no odor[2]
Density 1.322 g/cm3
Melting point 84.5 °C (184.1 °F; 357.6 K)
Boiling point None (polymerization); decomposes at 175-300°C[2]
390 g/L (25 °C)[3]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 potential occupational carcinogen[2]
GHS labelling:
GHS-pictogram-skull.svgGHS-pictogram-silhouette.svg[4]
H301, H312, H315, H317, H319, H332, H340, H350, H361, H372[4]
P201, P280, P301+P310, P305+P351+P338, P308+P313[4]
NFPA 704 (fire diamond)
3
2
2
Flash point 138 °C (280 °F; 411 K)
424 °C (795 °F; 697 K)
Lethal dose or concentration (LD, LC):
100-200 mg/kg (mammal, oral)
107 mg/kg (mouse, oral)
150 mg/kg (rabbit, oral)
150 mg/kg (guinea pig, oral)
124 mg/kg (rat, oral)[5]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 0.3 mg/m3 [skin][2]
REL (Recommended)
 Ca TWA 0.03 mg/m3 [skin][2]
IDLH (Immediate danger)
 60 mg/m3[2]
Safety data sheet (SDS) ICSC 0091
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Acrylamide forms in burnt areas of food, particularly starchy foods like potatoes, when cooked with high heat, above 120 °C (248 °F).[6][7] Despite health scares following its discovery in 2002, dietary acrylamide is thought unlikely to be carcinogenic for humans; Cancer Research UK categorized the idea that burnt food causes cancer as a "myth".[8][9]