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Chloracetonitril
2-Chloroacetonitrile · Chloracetonitrile · CH2ClCN · Chlorocyanomethane · CHLOROMETHYL CYANIDE · usafkf-5 · USAF kf-5 · oroacetonitriL
Identifikatoren & physikalische Daten
| CAS No. | 107-14-2 |
|---|---|
| Summenformel | C2H2ClN |
| Durchschnittliche Molmasse | 75,5 g/mol |
| Monoisotopische Masse | 74,98757674 g/mol |
| SMILES | N#CCCl |
| InChIKey | RENMDAKOXSCIGH-UHFFFAOYSA-N |
| PubChem CID | 7856 |
| ChEMBL | CHEMBL3187297 |
| ChEBI | CHEBI:82416 |
| EC No. | 203-467-0 |
| DTXSID | DTXSID7021524 |
| Lokaler Name | Chloracetonitril |
Chemische & physikalische Eigenschaften
| XLogP | 0,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 23,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 4 |
| Formalladung | 0 |
| Komplexität | 41,2 |
| Stoffklassen | Nitrogen Compounds -> NitrilesFlammable agents - 2nd degree |
| SpringerMaterials Properties | Coriolis coupling |
| LogP (Verteilungskoeffizient) | log Kow = 0.450.23 |
| Geruch | Pungent odor |
| Dichte | 1.2020 to 1.2035 at 77 °F (NTP, 1992)1.1930 g/cu cm at 20 °CRelative density (water = 1): 1.191.193 @ 20°C1.193 g/mL at 25 °C (lit.) |
| Color/Form | Colorless liquid |
| Löslichkeit | 50 to 100 mg/mL at 70.7 °F (NTP, 1992)Soluble in hydrocarbons, alcoholsIn ether and ethanolIn water, > 1X10+5 mg/L, temperature not specifiedSolubility in water: noneChloroform, Ethyl AcetateINSOLUBLE |
| Flammpunkt | 118 °F (NTP, 1992)47 °C |
| Siedepunkt | 259 to 261 °F at 760 mmHg (NTP, 1992)126.5 °C126 °C126.5 °C @760 [mm Hg]124-126 °C (lit.) |
| Decomposition | When heated to decomposition it emits very toxic fumes of /chlorides, nitrogen oxides, and cyanides/. |
| Dampfdichte | 2.61 (Air = 1)Relative vapor density (air = 1): 2.613 (vs air) |
| Dampfdruck | 8.7 [mmHg]8 mm Hg at 20 °CVapor pressure, kPa at 20 °C: 1.1615 [mm Hg] @30 °C1.78 psi ( 20 °C) |
| Schmelzpunkt | 38℃ |
| Brechungsindex | n20/D 1.422(lit.) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless |
| BRN | 506028 |
| Henry-Konstante | 9.1×10-1 mol/(m3Pa) at 25℃, HSDB (2015) |
| Dielektrizitätskonstante | 30.0 |
| Stabilität | Stable, but reacts with water. Combustible. Incompatible with water, moisture, strong oxidizing agents, acids. |
| InChI | 1S/C2H2ClN/c3-1-2-4/h1H2 |
| InChIKey | RENMDAKOXSCIGH-UHFFFAOYSA-N |
| SMILES | ClCC#N |
| LogP (Verteilungskoeffizient) | 0.45 |
| CAS Datenbank | 107-14-2(CAS DataBase Reference) |
| NIST chemische Informationen | Acetonitrile, chloro-(107-14-2) |
| EPA chemische Informationen | Chloroacetonitrile (107-14-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)H226 (79.3%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P321, P330, P337+P317, P361+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Hazards Identification | Toxic/poison by inhalation (TIH/PIH) |
| Regulatorische Informationen | Chemical: Acetonitrile, chloro-Status: Active Update: 02-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/20882Chloroacetonitrile: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| DOT-Kennzeichnung | Poison Inhalation Hazard Flammable Liquid |
| Brandgefahren | Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 47 °C explosive vapour/air mixtures may be formed. |
| Brandpotenzial | Flammable liquid. |
| Gesundheitsgefahren | Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:· TOXICmay be fatal if inhaled, ingested or absorbed through skin. |
| Gefahrenübersicht | A lachrymatorBurns the skin and eyesReacts with water and acids to form hydrogen chlorideHydrogen cyanide and hydrogen chloride are produced in a fire[CAMEO] See NITRILES. |
| DOT-Nummer und Handbuch | 2668 131 |
| Reaktive Gruppe | Halogenated Organic Compounds |
| EG-Einstufung | Symbol: T, NR: 23/24/25-51/53S: (1/2)-45-61 |
| UN-Einstufung | UN Hazard Class: 6.1UN Subsidiary Risks: 3UN Pack Group: II |
| RCRA-Anforderungen | P030As stipulated in 40 CFR 261.33, when chloroacetonitrile, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)). /Cyanides (soluble cyanide salts), not otherwise specified/ |
| Brandbekämpfung | Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention . |
| Freisetungsmaßnahmen | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.General First Aid: |
| Sichere Lagerung | Fireproof. Separated from strong oxidants, strong bases, strong acids and food and feedstuffs. Well closed. Cool. Ventilation along the floor. |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA).TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016]. |
| Brandbekämpfungsverfahren | Use water spray, dry chemical, foam, or carbon dioxide. Use water spray to keep fire-exposed containers cool. Approach fire from upwind to avoid hazardous vapors and toxic decomposition products.If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Extinguish fire using agent suitable for type surrounding fire(Material itself using agent does not burn or burns with difficulty). Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources. |
| Lagerbedingungen | Store in a cool, dry well-ventilated location. Separate from acids, alkalies, oxidizing materials, and reducing agents. Outside or detached storage preferred. |
| Reinigungsverfahren | Releases may require isolation or evacuation. Eliminate all ignition sources. Stop or control the leak, if this can be done with undue risk. Use water sprat or foam to cool and disperse vapors and protect personnel. Approach from upwind. Control runoff and isolate discharged material for proper disposal. |
| Freisetung ohne Brand | Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: |
| Entsorgungsverfahren | Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste numbers D003 and P030 must conform with USEPA regulations in storage, transportation, treatment and disposal of waste. /Cyanides (soluble cyanide salts), not otherwise specified/SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.A poor candidate for incineration. /Cyanides/ |
| Verschüttetes entsorgen | Evacuate danger area! Consult an expert! Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 9(SRC), determined from a structure estimation method(2), indicates that chloroacetonitrile is expected to have very high mobility in soil(SRC). Volatilization of chloroacetonitrile from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.08X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Chloroacetonitrile is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 8 mm Hg at 20 °C(3). Based on studies using pure culture soil methylotroph Methylosirius trichosporium OB-3b, chloroacetonitrile is expected to biodegrade in soil(4).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 9(SRC), determined from a structure estimation method(2), indicates that chloroacetonitrile is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.08X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 days and 25 days, respectively(SRC). According to a classification scheme(4), an estimated BCF of 3(SRC), from its log Kow of 0.45(5) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The aqueous hydrolysis rate constant for chloroacetonitrile at 20 °C and pH 8.7 was experimentally determined to be 1.2X10-6/sec(6) which corresponds to a half-life of 6.68 days(SRC)hydrolysis rates at neutral or acidic conditions is much slower(6) by approximately one to two orders of magnitude based on observed hydrolysis rates of the nine haloacetonitriles used in the study(SRC). Based on studies using pure culture soil methylotroph Methylosirius trichosporium OB-3b, chloroacetonitrile is expected to biodegrade in water(7).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chloroacetonitrile, which has a vapor pressure of 8 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase chloroacetonitrile is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 240 days(SRC), calculated from its rate constant of 6.74X10-14 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns. |
| Expositionspfade | The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion. |
| Signs and Symptoms | Sore throat. Cough. Headache. Laboured breathing. Weakness. Unconsciousness.MAY BE ABSORBED! Redness. Further see Inhalation.Further see Inhalation. |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from, as of June 21, 2012: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=107-14-2] |
| Effluent Concentrations | Chloroacetonitrile has been qualitatively detected in a wastewater effluent collected from the electronics industry (source and sampling date not reported)(1)and in the effluents from water treatment facilities that use chlorination(2). |
| ICSC Environmental Data | The substance is toxic to aquatic organisms. |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of chloroacetonitrile can be estimated to be 9(SRC). According to a classification scheme(2), this estimated Koc value suggests that chloroacetonitrile is expected to have very high mobility in soil. |
| Human Toxicity Excerpts | /GENOTOXICITY/ Chlorinated and brominated haloacetonitriles (HAN) were investigated for genotoxic activity. The HAN produced DNA strand breaks in cultured human lymphoblastic (CCRF-CEM) cells, bound to the nucleophilic trapping agent 4-(p-nitrobenzyl)pyridine and formed a covalent bond to polyadenylic acid in a cell-free reaction system. Thus, /it was/ demonstrated that these chemicals are genotoxic, which would indicate a potential for carcinogenic activity and for human health hazard. /haloacetonitriles//GENOTOXICITY/ The alkylating potential of the HAN to react with the electrophile-trapping agent, 4-(p-nitrobenzyl)pyridine, followed the order dibromoacetonitrile (DBAN) greater than bromochloroacetonitrile (BCAN) greater than chloroacetonitrile (CAN) greater than dichloroacetonitrile (DCAN) greater than trichloroacetonitrile (TCAN). ... The HAN produced DNA strand breaks in cultured human lymphoblastic (CCRF-CEM) cells. TCAN was the most potent DNA strand breaker, and BCAN greater than DBAN greater than DCAN greater than CAN, which was only marginally active. DCAN reacted with polyadenylic acid and DNA to form adducts in a cell-free systemhowever, the oral administration of DBAN or DCAN to rats did not result in detectable adduct formation in liver DNA. .../ALTERNATIVE and IN VITRO TESTS/ The present studies were initiated to measure the permeation coefficients (K(p)) for haloacetonitriles (HANs) and chloral hydrate (CH), important cytotoxic DBPs. The K(p) values measured using fully hydrated dermatomed torso skin at 37 °C for the HANs ranged from 0.099 to 0.17 cm h(-1) , and was 0.0039 cm h(-1) for CH. Of the HANs, dibromoacetonitrile had the highest permeability while chloroacetonitrile had the lowest permeability and a direct relationship was observed between their K(p) and their octanol/water partition coefficients (K(ow) ). The K(p) values of the HANs were also approximately 30 times that of CH. The monthly dermal and ingestion doses of HANs and CH of an average American population were estimated using Monte Carlo simulations. The dermal doses of HANs from showering and bathing ranged from 0.39 to 0.78 times their ingestion doses but only approximately 0.02 times their ingestion doses for CH, assuming that the K(p) values determined are applicable to shorter water contact times. However, that ratio can vary markedly with chlorinated swimming pool exposures, with a range of 0.30-2.3 for HANs and 0.19-0.25 for CH. Dermal exposure to HANs and CH seems to be a significant route of exposure and should be considered when evaluating their total exposure during the routine usage of water for bathing and swimming. /haloacetonitriles//OTHER TOXICITY INFORMATION/ Sister chromatid exchange was induced in one study using Chinese hamster ovary (CHO) cells, and DNA strand breaks (weakly) were induced in another using a human lymphoblast cell line. |
| Artificial Pollution Sources | Chloroacetonitrile's production and use as a chemical intermediate in the synthesis of the cardiovascular drug guanethidine and the insecticide fenoxycarb(1) may result in its release to the environment through various waste streams(SRC). Chloroacetonitrile has been detected in the wastewater effluent from the electronics industry(2) and in the effluents from water treatment facilities that use chlorination(3). Chloroacetonitrile is reported to be a disinfectant by-product of drinking water chlorination(4,5). |
| Environmental Biodegradation | PURE CULTURE: The biodegradation of chloroacetonitrile was studied using the soil methylotroph Methylosirius trichosporium OB-3b at pH 7.4 with 0.1 M phosphate buffer. Chloroacetonitrile was degraded entirely after 24 hours with formate being the major degradation product. Carbon monoxide, carbon dioxide, bicarbonate and cyanide were also listed as biodegradation products(1). |
| Carcinogen Classification | ChloroacetonitrileGroup 3: Not classifiable as to its carcinogenicity to humansVolume 52: (1991) Chlorinated Drinking-waterChlorination By-productsSome Other Halogenated CompoundsCobalt and Cobalt Compounds19991998 |
| Wassergefährdungsklasse (WGK) | 3 |
| Sofort lebensgefährliche Konzentration | 14 ppm |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2668 |
| Zollcode | 29269095 |
| RTECS-Nr. | AL8225000 |
| R-Sätze (R) | 23/24/25-51/53 |
| Gefahrensymbole | T,N |
| Sicherheitshinweise (S) | 45-61 |
| Gefahrenklasse | 6.1Acute Tox. 2 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Chronic 2Eye Irrit. 2Flam. Liq. 3 |
| Verpackungsgruppe | I |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrstoffdaten | 107-14-2(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
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.
Herstellung & Synthese
synthetische
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%).