1617-17-0

Basic information

• Product Name: 2-Chloropropionitrile
• Synonyms: 2-Chloropropanenitrile;Propanenitrile, 2-chloro-;2-CHLOROPROPIONITRILE;(2S)-2-chloropropanenitrile;(2S)-2-chloropropionitrile;2-Chloropropionitrile 95%
• CAS NO: 1617-17-0
• Molecular Formula: C₃H₄ClN
• Molecular Weight: 89.52
• EINECS: 216-570-0
• Product Categories: C1 to C5;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 1617-17-0.mol

Chemical Properties

• Melting Point: 54-55 °C
• Boiling Point: 120-122 °C(lit.)
• Flash Point: 92 °F
• Appearance: /
• Density: 1.012 g/mL at 25 °C(lit.)
• Vapor Pressure: 14mmHg at 25°C
• Refractive Index: n20/D 1.413(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-Chloropropionitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloropropionitrile(1617-17-0)
• EPA Substance Registry System: 2-Chloropropionitrile(1617-17-0)

Safety Data

• Hazard Codes: T
• Statements: 10-23/24/25-36/37/38
• Safety Statements: 16-26-27-36/37/39-45
• RIDADR: UN 3275 6.1/PG 2
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 1617-17-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloropropionitrile is used as a key intermediate in the synthesis of various pharmaceutical compounds, including active pharmaceutical ingredients (APIs) and drug candidates. Its reactivity and functional groups make it a versatile building block for the development of new drugs and therapies.
Used in Polymer Synthesis:
2-Chloropropionitrile is used as an initiator in the single-pot atom-transfer radical polymerization under microwave irradiation for the synthesis of polyacrylonitrile. This process allows for the creation of polymers with specific properties, such as enhanced strength, flexibility, or chemical resistance, which can be tailored for various applications.
Used in Synthesis of Nitrile Functionalized Methimazole-Based Ionic Liquids:
2-Chloropropionitrile is used as a starting material in the synthesis of nitrile functionalized methimazole-based ionic liquids, which are valuable compounds in the development of green chemistry and sustainable energy solutions.
Used in Synthesis of (+)and (-)-Anatoxin:
2-Chloropropionitrile is also used in the synthesis of (+)and (-)-anatoxin, which are biologically active compounds with potential applications in the pharmaceutical industry. These compounds can be used for the development of new drugs or as research tools to study biological processes and mechanisms.

Environmental Fate

Most of the toxicity of propionitrile results from release of cyanide. Cause of death is due to lack of oxygen to the body’s cells, especially to the brain and heart cells.

Acquired resistance

According to Henry’s law constant of 1.43×10-5 atmm3 mol-1, vapor pressure of 2.770mmHg and water solubility of 45 g ml-1 at 25°C are expected to indicate that volatilization from moist soil and water surfaces is expected to be an important fate process and also it can be volatilized from dry soil surfaces and exist as a vapor in the atmosphere.When heated to decomposition, it emits very toxic fumes of chlorine-containing compounds: nitrogen oxides, hydrogen cyanide, and hydrogen chloride.

InChI:InChI=1/C3H4ClN/c1-3(4)2-5/h3H,1H3

Upstream product

• 78-97-7 2-hydroxy-propionitrile 
• 27816-36-0 2-Chloropropionamide 
• 75-44-5 phosgene 
• 107-12-0 propiononitrile 
• 74-90-8 hydrogen cyanide 
• 75-07-0 acetaldehyde 
• 7782-50-5 chlorine 
• 19481-82-4 2-bromopropionitrile 
• 107-13-1 acrylonitrile 
• 76-02-8 trifluoroacetyl chloride 

Downstream Products

• 64879-76-1 2-tosylpropionitrile 
• 27816-36-0 2-Chloropropionamide 
• 107-13-1 acrylonitrile 
• 72335-18-3 2-Methyl-4-phenyl-4-chlorobutyronitril 
• 71270-15-0 N-(Cyano-methyl-methyl)-N-(2,6-dimethyl-phenyl)-methanesulfonamide 
• 62916-19-2 2-(Cyano-methyl-methoxy)-4-(2,6-dichloro-4-trifluoromethyl-phenoxy)-benzonitrile 
• 94217-06-8 2-(N-Benzyl-propion-amidinium)-thiosulfat 
• 801977-33-3 N-Butyl-α-chlor-propionamidin 
• 57836-69-8 2-[4-(2,4-Dichloro-benzyl)-phenoxy]-propionitrile 
• 62916-24-9 α-[3-(2'-chloro-4'-trifluoromethylphenoxy)-6-chlorophenoxy]propionitrile 
• 62916-20-5 2-[2-Bromo-5-(2-chloro-4-trifluoromethyl-phenoxy)-phenoxy]-propionitrile 
• 100402-23-1 2-Hydroxy-2-<1-Chlor-cyclohexyl-(1)>-propioimidsaeure-aethylester 
• 6275-86-1 3-hydroxy-2-methyl-3,3-diphenyl-propionitrile 
• 78302-27-9 2-(2,6-dichlorophenoxy)-propionitrile 

Relevant articles and documents

COMPETITION BETWEEN n,?- AND n,?-ORBITAL INTERACTIONS IN CHLORINATED ETHERS R-O-CHClR1

Using the AM-1 method, we have studied CH2=CH-O-CHClR1 molecules (R1 = H, Me).We have shown that the sc conformation with respect to the Csp3-O bond is preferred.We have systematized the 35Cl NOR data on the degree of manifestation of the generalized anomeric effect in R-OCHClR1 2C(=O)> molecules.We have established that enhancement of n,? conjugation in the R-O fragment leads to weakening of the n,? interaction in the O-C-Cl triad.

Nickel-Catalyzed Asymmetric Reductive Cross-Coupling between Heteroaryl Iodides and α-Chloronitriles

A Ni-catalyzed asymmetric reductive cross-coupling of heteroaryl iodides and α-chloronitriles has been developed. This method furnishes enantioenriched α,α-disubstituted nitriles from simple organohalide building blocks. The reaction tolerates a variety of heterocyclic coupling partners, including pyridines, pyrimidines, quinolines, thiophenes, and piperidines. The reaction proceeds under mild conditions at room temperature and precludes the need to pregenerate organometallic nucleophiles.

Mechanism of halogen exchange in ATRP

Detailed mechanistic studies reveal that halogen exchange (HE) in ATRP can occur not only by a radical pathway (atom transfer) but also by an ionic pathway (SN2 reaction) because Cu(I)(L)X and Cu (II)(L)X2 complexes contain weakly associated halide anion that can participate in the SN2 reaction with alkyl halide (ATRP initiator). Both pathways were kinetically studied, and their contributions to the HE process were quantitatively evaluated for seven alkyl halides and three Cu(I)(L)Cl complexes. Radical pathway dominates the HE process for 3° and 2° alkyl bromides with more active complexes such as Cu (I)(TPMA)Cl. Interestingly, ionic pathway dominates for 1° alkyl bromides and less active ATRP catalysts. These studies also revealed that degree of association of alkyl halide anion depends on the structure of copper complexes. In addition, radical pathway is accompanied by the reverse reactions such as deactivation of radicals to alkyl bromides and also activation of alkyl chlorides, reducing the efficiency of halogen exchange.

Reinvestigation of the reaction of trichloroacetyl chloride and acrylonitrile in the preparation of 3,5,6-trichloropyridin-2-ol

The synthesis of 3,5,6-trichloropyridin-2-ol via the CuCl-catalyzed reaction of trichloroacetyl chloride and acrylonitrile under both pressure and atmospheric conditions and the hydrolysis of the reaction mixture were reinvestigated. The products and byproducts formed in each case, before the hydrolysis step, were characterized, and the factors causing their formation are discussed. It was found that two newly identified byproducts influence the yield of the reaction.

PREPARATION OF NITRILES BY DEHYDRATION OF PRIMARY CARBOXAMIDES WITH A SUPPORTED PHOSPHORUS PENTOXIDE REAGENT

The use of a supported phosphorus pentoxide reagent in the synthesis of selected nitriles is discussed.