CAS NO. 109-75-1
Content: ≥99%
Packaging: 170 kg per barrel
3-butenitrile Details:
3-butenenitrile. Its chemical formula is C4H5N and its molecular weight is 67.09 g/mol.
3-Butenenitrile is an aliphatic nitrile and an olefinic compound. It has a carbon-carbon double bond and a carbon-nitrogen triple bond in its structure. It belongs to the class of organic compounds that contain a nitrile group with the general formula R-CN, where R is an organic group.
Some of the physical properties of 3-butenenitrile are listed below:
-
Color: clear colorless to yellow liquid
-
Shape: linear molecule
-
Odor: onion-like odor
-
Density: 0.834 g/mL at 25 °C (lit.)
-
Melting point: -87 °C
-
Boiling point: 116-121 °C (lit.)
-
Flash point: 75 °F
-
Solubility: not miscible in water; soluble in chloroform and ethyl acetate
-
Refractive index: n20/D 1.406
-
Vapor pressure: 16.3±0.2 mmHg at 25°C
-
Electrical conductivity: no data available
Some of the chemical properties of 3-butenenitrile are listed below:
-
Stability: stable under normal conditions; may polymerize in the presence of metals and some metal compounds
-
Reactivity: reacts with acids, strong oxidizing agents, and reducing agents; may form explosive peroxides in air
-
Acidity: weakly acidic; pKa = 25.5 (estimated)
-
Basicity: weakly basic; pKb = 8.5 (estimated)
-
Oxidation-reduction potential: E° = -0.46 V (estimated)
3-butenitrile Preparation methods
There are several methods to synthesize 3-butenenitrile, such as:
-
Reaction of allyl bromide and cuprous cyanide:
CH2=CHCH2Br+CuCN→CH2=CHCH2CN+CuBr
This method can yield 91.3% of 3-butenenitrile with
tetrabutylammonium bromide as a catalyst and toluene as a solvent at 60
°C for 6 hours.
-
Reaction of allyl chloride and sodium cyanide:
CH2=CHCH2Cl+NaCN→CH2=CHCH2CN+NaCl
This method can yield 99.5% of 3-butenenitrile with ferrous sulfate
as a reducing agent and sodium chloride as a salting-out agent at 60 °C
for 6 hours.
-
Hydrocyanation of butadiene:
CH2=CHCH=CH2+HCN→CH2=CHCH2CN
This method can yield 3-butenenitrile selectively with nickel
complexes as catalysts and phosphorus-containing ligands as modifiers.
3-butenitrile Uses and applications
Some of the uses and applications of 3-butenenitrile are listed below:
-
It is used as an anti-microbial agent, as it can release cyanide that inhibits the growth of bacteria and fungi.
-
It is used as a pharmaceutical intermediate, as it can be converted
into various compounds with biological activities, such as
anti-inflammatory, antiviral, antifungal, and anticancer agents.
-
It is used as a monomer for polymerization, as it can form
polyacrylonitrile and copolymers with other olefins, such as styrene and
acrylonitrile.
-
It is used as a flavor and fragrance ingredient, as it can impart
green, fruity, floral, and spicy notes to various products, such as
cosmetics, perfumes, food, and beverages.
3-butenitrile Safety and storage
Some of the safety and storage precautions for 3-butenenitrile are listed below:
-
It is a flammable, toxic, and irritant substance that can cause
severe harm to human health and the environment. It can cause skin and
eye irritation, respiratory distress, nausea, vomiting, headache,
dizziness, convulsions, coma, and death by inhalation, ingestion, or
skin contact.
-
It should be handled with care and personal protection, such as
gloves, goggles, masks, and clothing. It should be avoided contact with
skin, eyes, and mucous membranes. It should be used only in
well-ventilated areas or with respiratory protection. It should be kept
away from heat, sparks, flames, and other sources of ignition.
-
It should be stored in a cool, dry, and well-ventilated place. It
should be kept in a tightly closed container. It should be isolated from
incompatible materials, such as acids, oxidizers, and reducers. It
should be disposed of properly according to local regulations.
