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109-77-3 - Malononitrile, 99% - Dicyanomethane - Propanedinitrile - A15046 - Alfa Aesar

A15046 Malononitrile, 99%

CAS Number
109-77-3
Synonyms
Dicyanomethane
Propanedinitrile

Size Price ($) Quantity Availability
100g 22.35
500g 74.92
2500g 300.60
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Malononitrile, 99%

MDL
MFCD00001883
EINECS
203-703-2

Chemical Properties

Formula
C3H2N2
Formula Weight
66.06
Melting point
30-34°
Boiling Point
220-222°
Flash Point
112°(233°F)
Density
1.049
Refractive Index
1.4150
Solubility
Soluble in water, acetone, acetic acid, chloroform, ethanol, ether and benzene.

Applications

Crosslinking agent for modification of proteins via amidationMalononitrile is used as a precursor in the preparation of anti-cancer drug, triamterene, adenine, methotrexate, thiamine, acrylic fibers and dyes. It is used in Knoevenagel condensation to prepare 2-chlorobenzalmalononitrile by reacting with 2-chlorobenzaldehyde. It acts as a leaching agent for gold. It is used as a raw material for the Gewald reaction of ketone or aldehyde to produce 2-aminothiophene using elemental sulfur and a base. Further, it plays an important role in the preparation of [1,6]-naphthyridines, gamma-ketoamides, 1,4-dihydropyridine, chromeno[2,3-b]pyridine and dihydro-1,4-dithiepine frameworks.

Notes

Store in a cool place. Incompatible with strong oxidizing agents, strong reducing agents, strong acids and strong bases.

Literature References

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).

Reviews of the chemistry of malononitrile: Chem. Rev., 69, 591 (1969); Synthesis, 165, 241 (1978); 925 (1981); Synlett, 2247 (2004).

Caruana, L.; Mondatori, M.; Corti, V.; Morales, S.; Mazzanti, A.; Fochi, M.; Bernardi, L. Catalytic Asymmetric Addition of Meldrum’s Acid, Malononitrile, and 1,3-Dicarbonyls to ortho-Quinone Methides Generated In Situ Under Basic Conditions. Chem. Eur. J. 2015, 21 (16), 6037-6041.

Adili, A.; Tao, Z. L.; Chen, D. F.; Han, Z. Y. Quinine-catalyzed highly enantioselective cycloannulation of o-quinone methides with malononitrile. Org. Biomol. Chem. 2015, 13 (8), 2247-2250.

GHS Hazard and Precautionary Statements

Hazard Statements: H301-H311-H331-H400-H410

Toxic if swallowed. Toxic in contact with skin. Toxic if inhaled. Very toxic to aquatic life. Very toxic to aquatic life with long lasting effects.

Precautionary Statements: P261-P273-P280-P301+P310-P361-P304+P340-P311-P312-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Avoid release to the environment. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. Remove/Take off immediately all contaminated clothing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Call a POISON CENTER or doctor/physician. Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,5711
Beilstein
773697
Hazard Class
6.1
Packing Group
II
Harmonized Tariff Code
2926.90
TSCA
Yes
RTECS
OO3150000

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