propanedinitrile

• ChemBase ID: 92314
• Molecular Formular: C3H2N2
• Molecular Mass: 66.06138
• Monoisotopic Mass: 66.02179807
• SMILES: N#CCC#N
• Canonical SMILES: N#CCC#N
• InChI: InChI=1S/C3H2N2/c4-2-1-3-5/h1H2
• InChIKey: CUONGYYJJVDODC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: propanedinitrile
• IUPAC Traditional name: malononitrile
• Synonyms: Malononitrile; Cyanoacetonitrile; Malonic Dinitrile; Methylene Cyanide; Propanedinitrile; Malonic acid dinitrile; Dicyanomethane; Propane-1,3-dinitrile; Malononitrile; 二氰基甲烷; 丙二腈

Database IDs

• CAS Number: 109-77-3
• EC Number: 203-703-2
• MDL Number: MFCD00001883
• Beilstein Number: 773697
• Merck Index: 145711
• PubChem SID: 162079012; 24896644
• PubChem CID: 8010
• CHEBI ID: 33186
• Chemspider ID: 13884495
• Gmelin ID: 1303
• MeSH Name: dicyanmethane
• Wikipedia Title: Malononitrile

CALCULATED PROPERTIES

• Acid pKa: 8.516603
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.21563675
• LogD (pH = 7.4): -0.24716792
• Log P: -0.21521954
• Molar Refractivity: 16.9464 cm^3
• Polarizability: 5.9808116 Å^3
• Polar Surface Area: 47.58 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Soluble in water
• Apperance: Colourless crystals
• Melting Point: 30-32 °C(lit.); 30-34°C; 30-34°C; 31.85°C (305K); 32-34°C
• Boiling Point: 220 °C(lit.); 220°C; 220.05°C (493.2K); 220-222°C
• Flash Point: 112°C(233°F); 186.8 °F; 234°C; 86 °C; 86°C
• Density: 1.049; 1.049 g mL^-1; 1.049 g/ml; 1.049 g/mL at 25 °C(lit.)
• Refractive Index: 1.4150
• Vapor Pressure: 11 mm Hg at 99 °C, 20 mm Hg at 109 °C (measured)
• Heat Capacity: 110.29 J K^-1 mol^-1
• Std enthalpy of combustion: -1.6540–-1.6544 MJ mol^-1
• Std enthalpy of formation: 187.7–188.1 kJ mol^-1
• Std molar entropy: 130.96 J K^-1 mol^-1

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Toxic/Light Sensitive/Air Sensitive/Keep Cold/Store under Argon
• RTECS: OO3150000
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 2647; UN2647
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Australian Hazchem: 2X
• Risk Statements: 23/24/25-50/53; R:23/24/25-50/53; R23/24/25, R50/53
• Safety Statements: 23-27-45-60-61; S:23-27-45-60-61; S1/2, S27, S45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 153
• TSCA Listed: 是
• EU Index: 608-009-00-7
• GHS Pictograms: GHS environment; GHS skull and crossbones; GHS06; GHS09
• GHS Signal Word: DANGER; Danger
• LD50: 19 mg kg^-1 (oral, mouse); 350 mg kg^-1 (dermal, rat)
• GHS Hazard statements: 301, 311, 331, 410; H301-H311-H331-H400-H410; H301-H311-H331-H410
• GHS Precautionary statements: 261, 273, 280, 301+310, 311; P261-P273-P280-P301 + P310-P311-P501; P261-P301+P310-P361-P302+P352-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges; Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2647 6.1/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99%; ≥99.0% (calculated, GC, KF); 98%; 99%
• Grade: Lonza quality
• Impurities: ≤0.10% water; ≤0.50% (E)-2-butenedinitrile; ≤0.50% (Z)-2-butenedinitrile; ≤0.50% butanedinitrile
• Linear Formula: CH2(CN)2

DETAILS

MP Biomedicals - 02102240

Off-white solid
Purity: 98%
Used as a crosslinking agent
for the modification of proteins via amidation.

MP Biomedicals - 05201071

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 690414

Packaging
1 kg in glass bottle
10 kg in comp drum

Sigma Aldrich - M1407

Packaging
5, 100, 500 g in glass bottle

REFERENCES

• Davies, G.E., and Stark, G.R., Proc. Natl. Acad. Sci. U.S.A. , 66 : 651, (1970).
• Reviews of the chemistry of malononitrile: Chem. Rev., 69, 591 (1969); Synthesis, 165, 241 (1978); 925 (1981); Synlett, 2247 (2004).
• The Na derivative can be arylated by reaction with aryl halides with a Pd catalyst: J. Chem. Soc., Chem. Commun., 932 (1984). In the presence of butadiene, an additional 4-carbon unit is introduced: J. Chem. Soc., Perkin 1, 647 (1990):
  
• Ternary condensation with an aromatic aldehyde and a cycloalkanone in the presence of ammonium acetate can give a variety of products. With cyclohexanone, the 2-amino-4-aryl-5,6,7,8-tetrahydroquinoline-3-carbonitriles are the major products: J. Chem. Res. (Synop.), 146 (1995).