Acetonitrile

Base Information

• Chemical Name: Acetonitrile
• CAS No.: 75-05-8
• Deprecated CAS: 54841-72-4
• Molecular Formula: C2H3N
• Molecular Weight: 41.0525
• Hs Code.: 2926.90 Oral rat LD50: 2460 mg/kg
• European Community (EC) Number: 200-835-2,686-125-7
• ICSC Number: 0088
• NSC Number: 7593
• UN Number: 1648
• UNII: Z072SB282N
• DSSTox Substance ID: DTXSID7020009
• Nikkaji Number: J1.438I,J2.371.304G
• Wikipedia: Acetonitrile
• Wikidata: Q408047,Q83054373
• Metabolomics Workbench ID: 52223
• ChEMBL ID: CHEMBL45211
• Mol file: 75-05-8.mol

Synonyms:acetonitrile;acetonitrile, 1-(14)C-labeled;acetonitrile, 3H-labeled

Chemical Property of Acetonitrile

Chemical Property:

• Appearance/Colour: Clear liquid
• Vapor Pressure: 9.7kPa
• Melting Point: -46 °C
• Refractive Index: n20/D 1.344(lit.)
• Boiling Point: 63.452 °C at 760 mmHg
• Flash Point: 5.556 °C
• PSA: 23.79000
• Density: 0.747 g/cm³
• LogP: 0.52988
• Water Solubility.: miscible
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 41.026549100
• Heavy Atom Count: 3
• Complexity: 29.3
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): F, Xn, Xi, T
• Hazard Codes: F:Flammable;;
• Statements: R11:; R20/21/22:; R36:
• Safety Statements: S16:; S36/37:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: CC#N
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes. The substance may cause effects on the cellular respiration (inhibition). This may result in convulsions and respiratory failure. Exposure far above the OEL could cause death. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: The substance may have effects on the blood. This may result in anaemia. The substance may have effects on the kidneys, liver and thyroid. This may result in impaired functions.
• Properties as a Solvent for Acid-Base Chemistry: Acetonitrile is a useful solvent for non-aqueous acid-base chemistry due to its high relative permittivity (系r=36), which promotes the dissociation of ion pairs into free ions. It has a very low autoprotolysis constant, making it a good differentiating solvent, and its basicity is low for a dipolar aprotic solvent.; Acetonitrile's low ability for anion solvation makes it suitable for studies of strong acids.
• Application in Non-Aqueous Electrochemistry: Acetonitrile is a useful solvent for non-aqueous electrochemistry, being transparent for UV radiation down to 190 nm and readily available in high purity.
• Reactivity in Organic Reactions: Acetonitrile, as a small polar molecule with a high relative permittivity, can dissociate ion pairs into free ions, and its methyl proton is faintly acidic. It can be deprotonated to form nucleophiles and its nitrogen with lone pair electrons can also act as a nucleophile.; The cleavage of the H3C-CN bond generates radicals, making acetonitrile useful as a synthon in organic reactions.
• Utility in Organic Synthesis: Acetonitrile is widely used as a common solvent in organic synthesis due to its low price, excellent solvent properties, and availability. It serves as a synthetic intermediate and a source of nitrogen for the preparation of nitrogen-containing compounds, including nitrile-containing compounds used in medicines and materials.
• Role as a Building Block in Organic Reactions: Acetonitrile provides three active sites: two carbons and one nitrogen, enabling its use in various transformations such as cyanomethylation, the Ritter reaction, cyanation, and cyclization reactions. It has been used in the synthesis of heterocyclic compounds like pyridine, oxazole, and tetrazole.
• Application in Catalysis and Electrochemistry: Acetonitrile is commonly used as a nonaqueous solvent in catalysis and electrochemistry due to its favorable properties.
• Production and Potential Feedstocks: Acetonitrile has historically been produced as a byproduct in the production of acrylonitrile via propylene ammoxidation. With the depletion of crude reservoirs, light alkanes like propane, ethane, and methane are being explored as potential feedstocks for the synthesis of acrylonitrile and acetonitrile.

Technology Process of Acetonitrile

There total 836 articles about Acetonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

4-hydroxy-3-methyl-4-phenylisoxazoline-5-one (80490-51-3) → Benzoylformic acid (611-73-4) + acetonitrile (75-05-8,26809-02-9)

Guidance literature:

With 2,6-dichloro-benzonitrile; In benzene; for 0.5h; Heating;

Reference yield: 44.0%

3-phenyl-4,4-dimethyl-5-oxo-2-isoxazoline (51942-54-2) → styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 2,2-dimethyl-3-phenyl-2H-azirine (14491-02-2) + acetonitrile (75-05-8,26809-02-9)

Guidance literature:

at 600 ℃; under 7.50075E-05 - 0.000750075 Torr;

DOI:10.1021/jo402667y

Reference yield: 40.0%

2,2-dimethyl-3-phenyl-2H-azirine (14491-02-2) → styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + acetonitrile (75-05-8,26809-02-9)

Guidance literature:

at 650 ℃; under 7.50075E-05 - 0.000750075 Torr;

DOI:10.1021/jo402667y

upstream raw materials:

diazomethane

hydrogen cyanide

pyridine

thioacetamide

Downstream raw materials:

crotononitrile

but-3-enenitrile

1-piperidin-1-yl-ethanone

dichloro(2-cyanoethyl)methylsilane

Refernces

• 1、 Hassoon, Salah,Rajapakse, Nandani,Snavely, Deanne L.. "Vibrational Overtone Activation of the Isomerization of Methyl Isocyanide". . p. 2576 - 2581. Retrieved 1992.
• 2、 Lynn, K. R.,Yankwich, P. E.. "-". . p. 3220 - 3223. Retrieved 1961.
• 3、 Gamasa, Pilar M.,Gimeno, Jose,Lastra, Elena,Solans, Xavier. "An unusual coordination mode of acetylide ligands: synthesis of tetranuclear copper(I) complexes containing μ3-η1acetylide ridging ligands. Crystal structure of 3-η1-CCPh)-(Ph2Ppy-P)>4 (Ph2Ppy=2-(diphenylphosphine)pyridine)". . p. 277 - 286. Retrieved 1988.
• 4、 Ayari,Mhamdi,álvarez-Rodríguez,Guerrero Ruiz,Delahay,Ghorbel. "Ammoxidation of ethylene over low and over-exchanged Cr-ZSM-5 catalysts". . p. 132 - 140. Retrieved 2012.
• 5、 Kang, Yunji,Park, In-Hyeok,Ikeda, Mari,Habata, Yoichi,Lee, Shim Sung. "A double decker type complex: Copper(I) iodide complexation with mixed donor macrocycles via [1:1] and [2:2] cyclisations". . p. 4528 - 4533. Retrieved 2016.
• 6、 Cohen, Benyamin,Weiss, Shmuel. "Picosecond Kinetics by Exchange Broadening in the Infrared and Raman. 3. CH3CN.IBr". . p. 3974 - 3976. Retrieved 1984.
• 7、 Schneider,Rabinovitch. "-". . p. 4215,4217. Retrieved 1962.
• 8、 Shultz, M. J.,Yam, L. M.,Tricca, Robert E.. "ENERGY TRANSFER IN THE INFRARED LASER-INDUCED REACTION OF METHYL ISOCYANIDE". . p. 1884 - 1888. Retrieved 1989.
• 9、 Galanov,Sidorova. "Effect of phosphorus-oxygen compounds on structural, acidic, and catalytic properties of γ-alumina in the acetic acid ammonolysis reaction". . p. 387 - 391. Retrieved 2014.
• 10、 Shultz, M. J.,Tricca, Robert E.,Yam, Loretta M.. "Interdependence of Fluence and Pressure in the Laser-Induced Isomerization of Methyl Isocyanide". . p. 58 - 61. Retrieved 1985.