Malononitrile
- CAS No.
- 109-77-3
- Chemical Name:
- Malononitrile
- Synonyms
- PROPANEDINITRILE;MALONITRILE;malonic;MALONODINITRILE;CH2(CN)2;MDN;DICYANOMETHANE;propanedinitrite;Malonic dinitrile;MALONIC ACID DINITRIL
- CBNumber:
- CB2259712
- Molecular Formula:
- C3H2N2
- Molecular Weight:
- 66.06
- MOL File:
- 109-77-3.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/7/29 17:07:33
| Melting point | 30-32 °C (lit.) |
|---|---|
| Boiling point | 220 °C (lit.) |
| Density | 1.049 g/mL at 25 °C (lit.) |
| vapor pressure | 1 hPa (50 °C) |
| refractive index | 1.4150 |
| Flash point | 234 °F |
| storage temp. | 2-8°C |
| solubility | 133g/l |
| pka | 11(at 25℃) |
| form | Crystalline Low Melting Mass |
| color | White to yellow-brown |
| Specific Gravity | 1.049 |
| PH | pH : 4.5 |
| Water Solubility | 13.3 g/100 mL (20 ºC) |
| Merck | 14,5711 |
| BRN | 773697 |
| Exposure limits | TLV-TWA 8 mg/m3 (3 ppm) (NIOSH). |
| Dielectric constant | 46.0 |
| InChIKey | CUONGYYJJVDODC-UHFFFAOYSA-N |
| CAS DataBase Reference | 109-77-3(CAS DataBase Reference) |
| NIST Chemistry Reference | Malononitrile(109-77-3) |
| EPA Substance Registry System | Malononitrile (109-77-3) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS06,GHS09 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H300-H311+H331-H317-H319-H410 | |||||||||
| Precautionary statements | P273-P280-P301+P310-P302+P352+P312-P304+P340+P311-P305+P351+P338 | |||||||||
| Hazard Codes | T,N | |||||||||
| Risk Statements | 23/24/25-50/53 | |||||||||
| Safety Statements | 23-27-45-60-61 | |||||||||
| OEB | B | |||||||||
| OEL | TWA: 3 ppm (8 mg/m3) | |||||||||
| RIDADR | UN 2647 6.1/PG 2 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | OO3150000 | |||||||||
| F | 8 | |||||||||
| Autoignition Temperature | 365 °C | |||||||||
| TSCA | Yes | |||||||||
| HazardClass | 6.1 | |||||||||
| PackingGroup | II | |||||||||
| HS Code | 29269090 | |||||||||
| Toxicity | LD50 i.p. in mice: 12.9 mg/kg (Jones, Israel) | |||||||||
| NFPA 704 |
|
Malononitrile price More Price(21)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | M1407 | Malononitrile ≥99% | 109-77-3 | 5G | ₹1558.8 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | M1407 | Malononitrile ≥99% | 109-77-3 | 100G | ₹1948.5 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | M1407 | Malononitrile ≥99% | 109-77-3 | 500G | ₹7339.35 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 8.06189 | Malononitrile for synthesis | 109-77-3 | 100G | ₹4589.99 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 8.06189 | Malononitrile for synthesis | 109-77-3 | 250G | ₹7770 | 2022-06-14 | Buy |
Malononitrile Chemical Properties,Uses,Production
Description
Malonitrile, also known as Malononitrile, is an aliphatic nitrile that can release cyanide through chemical or biological transformation. It was also used decades ago for treating certain forms of mental illness.
Chemical Properties
Malononitrile is a white powder or colorless, odorless crystalline substance. It may polymerize violently on prolonged heating at 130°C or at lower temperatures on contact with strong bases.
Uses
Malononitrile is an important building block for the syntheses of pharmaceuticals (e.g. triamterene, adenine and methotrexate), thiamin (vitamin B1), pesticides dyestuffs for color photography and synthetic fibers (e.g. vinylidene cyanide). Product Data Sheet
Definition
ChEBI: Malononitrile is a dinitrile that is methane substituted by two cyano groups. It is a dinitrile and an aliphatic nitrile.
Production Methods
Malononitrile can be synthesized by a continuous method where preheated acetonitrile and cyanogen chloride are introduced into a tube reactor until the reaction mixture reaches a temperature of about 780°C. Another way to prepare malononitrile is by reacting phosphorus pentachloride with cyanoacetamide, or by using phosphorus pentoxide to react with malonamide or cyanoacetamide.
DOI: 10.15227/orgsyn.010.0066
General Description
A white-colored crystalline solid. Denser than water and soluble in water. Toxic by ingestion and may severely irritate skin and eyes. May polymerize violently if exposed to temperatures above 266°F. Used to make other chemicals.
Air & Water Reactions
Soluble in water.
Reactivity Profile
Malononitrile is a white, low-melting powder (m. p. 30.5° C), toxic, combustible. Violent polymerization on contact with strong bases (sodium hydroxide, potassium hydroxide) or when heated above 130° C. When stored at 70-80° C for 2 months, spontaneous explosion (decomposition) occurred [Bretherick, 5th ed., 1995, p. 394].
Hazard
Toxic by ingestion and inhalation.
Fire Hazard
When heated to decomposition, Malononitrile emits highly toxic fumes (cyanide). May polymerize violently on prolonged heating. Avoid heat. Hazardous polymerization may occur, at prolonged heating at 266F or contact with strong bases at lower temperatures.
Industrial uses
Malononitrile is used primarily as an intermediate in the synthesis of drugs and
vitamins (thiamine). It has also been employed in the manufacture of photosensitizes,
acrylic fibers and dyestuffs and as an oil-soluble polar additive in lubricating
oil.
Malononitrile was used formerly in treatment of various forms of mental illness
such as alteration of psychic functions and schizophrenic
disorders.
Safety Profile
Poison by ingestion, skin contact, subcutaneous, intravenous, and intraperitoneal routes. A severe eye irritant. Combustible when exposed to heat or flame. Polymerizes violently when heated to 130°C or on contact with strong base. May spontaneously explode when stored at 70-80°C. To fight fire, use water, fog, spray, foam. When heated to decomposition it emits toxic fumes of NOx and CN-. See also NITRILES.
Environmental Fate
When heated to decomposition, nitriles may release cyanide. Malonitrile appears to decompose rapidly in contact with soil and sediment.
Metabolism
The in vitro metabolsim of malononitrile has been described by Stern et al. In the presence of thiosulphate, brain, liver and kidney slices metabolized malononitrile to thiocyanate. The formation of thiocyanate from malononitrile and thiosulphate was greatest in the presence of liver slices, lowest in brain, and intermediate with kidney slices. The liver enzyme system was saturated at a concentration of 3.3 mM malononitrile and a pH optimum of 7.0. This enzyme system was inhibited by cysteine and glutathione and inactivated by boiling. Stern et al indicated that thiosulphate increased cyanide and thiocyanate formed from malononitrile in tissue slices.
Purification Methods
Crystallise the nitrile from water, EtOH, *benzene or chloroform. Distil it in a vacuum from, and store over, P2O5. [Bernasconi et al. J Am Chem Soc 107 7692 1985, Gratenhuis J Am Chem Soc 109 8044 1987, Beilstein 2 IV 1892.]
Incompatibilities
Incompatible with strong bases. May polymerize violently on prolonged heating @ 129C, or in contact with strong bases at lower temperatures. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.
Malononitrile Preparation Products And Raw materials
Raw materials
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chevron_rightPreparation Products
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chevron_right| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| JSK Chemicals | +919879767970 | Gujarat, India | 3756 | 58 | Inquiry |
| Otto Chemie Pvt Ltd | +91-2222070099 +91-2266382599 | Maharashtra, India | 429 | 58 | Inquiry |
| S D Fine Chem Limited | +91-9323715856 +91-9323715856 | Maharashtra, India | 368 | 58 | Inquiry |
| Inventys Research Company Pvt Ltd | +91-2271400200 +91-9320013358 | Mumbai, India | 21 | 58 | Inquiry |
| ALPHA CHEMIKA | +91-22-22061123 +91-22-66382501 | Mumbai, India | 1681 | 43 | Inquiry |
| Scientific OEM | +91-22- 2343 7546 / 2341 3094 | New Delhi, India | 1996 | 38 | Inquiry |
| Multichem Specialities Pvt. Ltd. | 08048372725Ext 201 | Mumbai, India | 88 | 58 | Inquiry |
| Mahavir Interchem | 08048250471Ext 771 | Mumbai, India | 33 | 58 | Inquiry |
| Reliable Traders | 08047641743 | Mumbai, India | 24 | 58 | Inquiry |
| Organic Chemicals | 08048372709Ext 384 | Pune, India | 75 | 58 | Inquiry |
| Supplier | Advantage |
|---|---|
| JSK Chemicals | 58 |
| Otto Chemie Pvt Ltd | 58 |
| S D Fine Chem Limited | 58 |
| Inventys Research Company Pvt Ltd | 58 |
| ALPHA CHEMIKA | 43 |
| Scientific OEM | 38 |
| Multichem Specialities Pvt. Ltd. | 58 |
| Mahavir Interchem | 58 |
| Reliable Traders | 58 |
| Organic Chemicals | 58 |