107-14-2 Usage
Product features
Chloroacetonitrile, also known as "cyanide chloromethane" has its chemical formula being ClCH2CN and the molecular weight being 75.50. It is colorless and fuming liquid with the melting point being 38 ℃ and boiling point being 126~127 ℃ (decomposition), 30~32 ℃ (2.0kPa), the relative density being 1.1930 and the refractive index being 1.420225. It is soluble in ether, alcohol and hydrocarbons but insoluble in water. It is highly toxic. It can form adduct with aluminum trichloride and react with various kinds of reagents including phloroglucinol trimethylether, methoxyacetophenone, Grignard reagent and anhydrous hydrogen chloride. It can be obtained through the dehydration of chloroacetamide under the action of phosphorus pentoxide, or the reaction between excess amount of acetonitrile with chlorine at 460 ℃ as well as introducing ammonia gas into the ether solution of dichloro acetylene. Chloroacetonitrile can be used as a fumigant.
Fumigants refer to a kind of pesticides whose volatile vapor can be applied to poison and kill pests. Its gaseous molecules can enter into the body of the harmful organisms and exert toxic effects. It can also exist in forms being different from gas such as liquid, solid or compressed gaseous form. The usage dose can be calculated according to the volume of space fumigation place (unit: g/m 3). The applied concentration can be based on the fumigation period, the closeness extent of fumigation place and the amount of material as well as its absorption capability of fumigant vapor. It is suitable to be used in the closed or nearly closed conditions in places such as warehouse, tent, house, car, etc. In the case of large concentration of the object to be fumigated, it can effectively eliminate hidden pests or pathogens.
The fumigant vapor generally directly enters into the respiratory system through the skin or valve of the pests, thus penetrating into blood and cause the poisoning and death of pests. Its insecticidal effect is generally believed to be located in the chemical action on the enzyme. For example, methyl bromide can combine with thiol, causing gradually reversible or irreversible inhibitory effects on various kinds of enzymes inside the pest body. Phosphine can cause inhibition on the animal central nervous system, irritate the lungs and cause edema, resulting in swelling heart syndrome. Fumigants such as trichloroethane, dibromoethane and carbon tetrachloride are mainly narcotics while carbon dioxide mainly causes stifling effect.
This information is edited by Xiongfeng Dai from lookchem.
Chemical Properties
Different sources of media describe the Chemical Properties of 107-14-2 differently. You can refer to the following data:
1. It is colorless, transparent fuming liquid with a pungent choking smell. It is soluble in alcohol and ether.
2. colourless liquid
3. A clear, colorless liquid. Pungent odor.
Uses
Different sources of media describe the Uses of 107-14-2 differently. You can refer to the following data:
1. 1. It can be used as raw material of organic synthesis and analytical reagents.
2. It can be used as pharmaceutical intermediates, pesticides.
2. Fumigant, intermediate.
3. Chloroacetonitrile is used in the electrochemical synthesis of cyanoacetic acid with carbon dioxide. It is involved in phase-transfer-catalyzed Darzen's condensation reaction with cyclohexanone. It is also used as an eluent additive in thermospray liquid chromatography/mass spectrometry. Further, it is used to prepare polysubstituted pyrido[1,2-a]benzimidazole by reacting with other reactant such as malononitrile, aromatic aldehyde and pyridine.
Production method
It can be obtained through: chloroacetic acid is reacted with ethanol to generate ethyl chloroacetate, which then generate chloroacetamide through reaction with ammonia; finally have dehydration to get it. Detailed process: add trichloroacetic acid to the ethanol; add under stirring of concentrated sulfuric acid; the stirring was stopped after heating reflux; have the reaction for 8-10 h, filter and wash with water, separate out the water layer to obtain ethyl chloroacetate. Add it to the ammonia of 0-2 ℃ with the temperature being not exceed 15 ℃; sir for 10 to 15 mins after finishing adding added, cool, stand, filtrate and dry to obtain the chloroacetamide. Then, to the chloroacetamide, add phosphorus pentoxide and perform thermal dehydration with heating and distilling chloroacetonitrile out simultaneously; finally perform distillation under reduced pressure to evaporate out all the chloroacetonitrile. The resulting crude product is hydrated using phosphorus pentoxide and magnesium sulfate with vacuum distillation to derive the finished products.
Category
Toxic substances.
Toxicity grading
Highly toxic.
Acute toxicity
Oral-rat LD50: 220 mg/kg; Oral-Mouse LD50: 139 mg/kg.
Irritation data
Skin-Rabbit 14 mg/24 hr mild; Eye-Rabbit 20 mg/24 hours of moderate.
Flammable and hazardous characteristics
Combustible upon fire with thermal decomposition into toxic nitrogen compounds, chloride and cyanide gas.
Storage characteristics
Treasury: ventilated and low-temperature and dry; store it separately from oxidants, acids and food additives.
Extinguishing agent
Dry powder, carbon dioxide and sand. pH extinguishing agent should be disabled.
Preparation
In a 3-L round-bottomed, threenecked flask fitted with an efficient mechanical stirrer, a reflux condenser, and a thermometer were placed phosphorus pentoxide (170 g, 1.2 mol), chloroacetamide 1423 (187 g, 2 mol), and dry technical grade trimethylbenzene (800 mL). The mixture was gently refluxed with vigorous stirring for 1 h. It was then allowed to cool to about 100 C° with continuous stirring, and the reflux condenser was replaced with a distillation head fitted with a thermometer and a water-cooled condenser. The crude product and part of the solvent were distilled at atmospheric pressure. The yield of crude product boiling at 124–128 C° was 121–131 g (80–87%). In order to obtain a pure product, the crude chloroacetonitrile was mixed with phosphorus pentoxide (10 g) and redistilled through an efficient packed fractionating column. The yield of pure chloroacetonitrile distilling at 123–124 C° was 93–106 g (62–70%).
General Description
A colorless liquid with a pungent odor. Flash point 118°F. Insoluble in water and denser than water. Hence, sinks in water. Very toxic by ingestion, inhalation and skin absorption. A lachrymator. Used to make other chemicals and as a fumigant.
Air & Water Reactions
Flammable. Insoluble in water and denser than water. Hence, sinks in water. Reacts with water and steam to produce toxic vapors of hydrogen chloride.
Reactivity Profile
Chloroacetonitrile reacts with water, steam, strong acids or acid fumes to produce toxic vapors of hydrogen chloride. When heated to decomposition, Chloroacetonitrile emits highly toxic fumes of hydrogen cyanide and hydrogen chloride [Sax, 2nd ed., 1963, p. 600].
Hazard
Irritant. Questionable carcinogen.
Health Hazard
TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
Fire Hazard
HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
Safety Profile
Poison by ingestion,
skin contact, and intraperitoneal routes.
Moderately toxic by inhalation. A skin
irritant. Human mutation data reported.
Questionable carcinogen with experimental
tumorigenic data. Flammable liquid. See also
NITRILES. When heated to decomposition
it emits very toxic fumes of Cl-, NOx, and
CN-.
Potential Exposure
A chlorinated haloacetonitrile used as
a fumigant and as a manufacturing chemical intermediate
for making other chemicals
Shipping
UN2668 Chloroaceto nitrile Hazard class: 6.1,
Labels: 6.1-Poison Inhalation Hazard, 3-Flammable liquid
Inhalation Hazard Zone B.
Purification Methods
Reflux it with P2O5 for one day, then distil it through a helices-packed column. Also purified by gas chromatography. [Beilstein 2 IV 492.] LACHRYMATOR, HIGHLY TOXIC.
Incompatibilities
Highly flammable, forms explosive mixture with air. Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides. Reacts with water and
steam, releasing toxic and corrosive vapors of hydrogen
chloride. 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 low aqueous solubility. They are also insoluble in aqueous
acids.
with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have
Waste Disposal
Use a licensed professional
waste disposal service to dispose of this material. Dissolve
or mix the material with a combustible solvent and burn in
a chemical incinerator equipped with an afterburner and
scrubber. All federal, state, and local environmental regulations must be observed.
Check Digit Verification of cas no
The CAS Registry Mumber 107-14-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 7 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 107-14:
(5*1)+(4*0)+(3*7)+(2*1)+(1*4)=32
32 % 10 = 2
So 107-14-2 is a valid CAS Registry Number.
InChI:InChI=1/C2H2ClN/c3-1-2-4/h1H2
107-14-2Relevant articles and documents
-
Chi,Tshin
, p. 90 (1942)
-
The Photolyses of 2,6- and 2,4-Difluorohalobenzenes
Song, Yong-Qi,Yuzuri, Tomoaki,Suezawa, Hiroko,Sakakibara, Kazuhisa,Hirota, Minoru,Nakada, Masahiro
, p. 1875 - 1878 (1997)
Photolyses of 2,6- and 2,4-difluorobromobenzenes in acetonitrile gave isomerized and brominated products in addition to 1,3-difluorobenzene produced by the dehalogenation.The reactions were compared with similar reactions of the corresponding chloro- and iodoarenes.In general, photolytic cleavage of the C-X bond of 2,6-difluorohalo(X)benzene was shown to proceed more easily than the corresponding 2,4-difluorohalo compound.
Photocatalytic C-H activation and the subtle role of chlorine radical complexation in reactivity
Yang, Qiaomu,Wang, Yu-Heng,Qiao, Yusen,Gau, Michael,Carroll, Patrick J.,Walsh, Patrick J.,Schelter, Eric J.
, p. 847 - 852 (2021/05/28)
The functionalization of methane, ethane, and other alkanes derived from fossil fuels is a central goal in the chemical enterprise. Recently, a photocatalytic system comprising [CeIVCl5(OR)]2- [CeIV, cerium(IV); OR, -OCH3 or -OCCl2CH3] was disclosed. The system was reportedly capable of alkane activation by alkoxy radicals (RO·) formed by CeIV-OR bond photolysis. In this work, we present evidence that the reported carbon-hydrogen (C-H) activation of alkanes is instead mediated by the photocatalyst [NEt4]2[CeCl6] (NEt4+, tetraethylammonium), and RO· are not intermediates. Spectroscopic analyses and kinetics were investigated for C-H activation to identify chlorine radical (Cl·) generation as the ratelimiting step. Density functional theory calculations support the formation of [Cl·][alcohol] adducts when alcohols are present, which can manifest a masked RO· character. This result serves as an important cautionary note for interpretation of radical trapping experiments.
New method for synthesis of chlorocyanomethane
-
Paragraph 0049-0050, (2020/07/21)
The invention discloses a new method for synthesis of chlorocyanomethane, and belongs to the technical field of synthesis. The method comprises the following steps: firstly, dissolving a compound rawmaterial with a general formula (II) in a solvent, then adding a chlorination reagent to carry out chlorination reaction, and at the end of the reaction, not treating the reaction liquid; and then adding a catalyst into water, adding the reaction liquid obtained at the end of the chlorination reaction into the water dropwise, carrying out hydrolysis decarboxylation reaction, and performing purification at the end of the reaction so as to obtain the chlorocyanomethane. The method has the advantages of mild reaction conditions, high product yield and good product quality.
Synthetic method for methanesulfonic phentolamine drug intermediate chloroacetonitrile
-
Paragraph 0014; 0015, (2016/11/09)
The invention relates to a synthetic method for methanesulfonic phentolamine drug intermediate chloroacetonitrile. The synthetic method includes the following steps that 6.3 mol of 1-chloro-2,2-dyhydroxyl ethylamine, 5.6 mol of cuprous chloride, 7.3-7.6 mol of a 2-amino bromobenzene solution and 300 ml of cyclohexane are added into a reaction container provided with a stirrer, a thermometer and a dropping funnel, the stirring speed is controlled to be 150-190 rpm, the solution temperature is raised to 90 DEG C-98 DEG C to carry out reaction for 5-7 h, the solution temperature is lowered to 70 DEG C-76 DEG C to continue to carry out reaction for 80-120 min, the solution temperature is lowered to 10 DEG C-16 DEG C, the solution stands for 8-10 h, and a solid is separated, filtered, washed with a saline solution, acetonitrile and ethanediamine, and dehydrated with a dehydrating agent, and distilled in a reduced pressure mode, and fraction at the temperature of 100 DEG C-108 DEG C is collected and recrystallized in dimethylamine to obtain crystal chloroacetonitrile.