| |||
Names | |||
---|---|---|---|
IUPAC name
Malononitrile
[2]
| |||
Preferred IUPAC name
Propanedinitrile
[2] | |||
Other names
Malonodinitrile, Cyanoacetonitrile, Dicyanomethane, Malonic dinitrile
[1]
| |||
Identifiers | |||
3D model (
JSmol)
|
|||
773697 | |||
ChEBI | |||
ChemSpider | |||
ECHA InfoCard | 100.003.368 | ||
EC Number |
| ||
1303 | |||
MeSH | dicyanmethane | ||
PubChem
CID
|
|||
RTECS number |
| ||
UNII | |||
UN number | 2647 | ||
CompTox Dashboard (
EPA)
|
|||
| |||
| |||
Properties | |||
CH2(CN)2 | |||
Molar mass | 66.063 g·mol−1 | ||
Appearance | Colourless or white solid [1] | ||
Density | 1.049 g cm−3 | ||
Melting point | 32 °C; 89 °F; 305 K | ||
Boiling point | 220.1 °C; 428.1 °F; 493.2 K | ||
13% (20 °C) [1][ clarification needed] | |||
Thermochemistry | |||
Heat capacity (C)
|
110.29 J K−1 mol−1 | ||
Std molar
entropy (S⦵298) |
130.96 J K−1 mol−1 | ||
Std enthalpy of
formation (ΔfH⦵298) |
187.7 to 188.1 kJ mol−1 | ||
Std enthalpy of
combustion (ΔcH⦵298) |
−1,654.0 to −1,654.4 kJ mol−1 | ||
Hazards | |||
GHS labelling: | |||
Danger | |||
H301, H311, H331, H410 | |||
P261, P273, P280, P301+P310, P311 | |||
Flash point | 86 °C (187 °F; 359 K) | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (
median dose)
|
| ||
NIOSH (US health exposure limits): | |||
PEL (Permissible)
|
none [1] | ||
REL (Recommended)
|
TWA 3 ppm (8 mg/m3) [1] | ||
IDLH (Immediate danger)
|
N.D. [1] | ||
Related compounds | |||
Related alkanenitriles
|
|||
Related compounds
|
DBNPA | ||
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Malononitrile is an organic compound nitrile with the formula CH2(CN)2. It is a colorless or white solid, although aged samples appear yellow or even brown. It is a widely used building block in organic synthesis.
It can be prepared by dehydration of cyanoacetamide. [3] This method is mainly practiced in China where environmental rules are lax. Most commonly malononitrile is produced by the gas-phase reaction of acetonitrile and cyanogen chloride: [4]
About 20,000,000 kg are produced annually (2007). Important outlets include the synthesis of thiamine, the drug triamterene and minoxidil, and the dyes disperse Yellow 90 and disperse Blue 354. [4]
Malononitrile is relatively acidic, with a pKa of 11 in water. [5] This allows it to be used in the Knoevenagel condensation, for example in the preparation of CS gas:
Malononitrile is a suitable starting material for the Gewald reaction, where the nitrile condenses with a ketone or aldehyde in the presence of elemental sulfur and a base to produce a 2-amino thiophene. [6]