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Cyanoacetic acid
2-Cyanoacetic acid · 2-cyanoacetate · Cyanicycnab acid · CYAD · NCCH2COOH · Cyanoacetic · usafkf-17 · USAF kf-17
Identifikatoren & physikalische Daten
| CAS No. | 372-09-8 |
|---|---|
| Summenformel | C3H3NO2 |
| Durchschnittliche Molmasse | 85,06 g/mol |
| Monoisotopische Masse | 85,01637834 g/mol |
| SMILES | N#CCC(=O)O |
| InChIKey | MLIREBYILWEBDM-UHFFFAOYSA-N |
| PubChem CID | 9740 |
| ChEMBL | CHEMBL3185860 |
| ChEBI | CHEBI:51889 |
| EC No. | 206-743-9 |
| DTXSID | DTXSID0027149 |
| Lokaler Name | Cyanessigsäure |
Chemische & physikalische Eigenschaften
| XLogP | -0,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 61,1 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 6 |
| Formalladung | 0 |
| Komplexität | 98 |
| LogP (Verteilungskoeffizient) | log Kow = -0.76 |
| Dichte | greater than 1.1 at 68 °F (USCG, 1999)1.3676 (rough estimate) |
| Color/Form | Hygroscopic crystals |
| Löslichkeit | Sol in water, alcohol, etherslightly sol in benzene, chloroformSlightly sol in acetic acidH2O: soluble50mg/mL, clear, colorless to very faintly yellow1000 g/L (20 ºC) |
| Siedepunkt | 108 °C at 15 mm Hg108 °C0.15 mm Hg(lit.) |
| Decomposition | Decomposes at 320 °F (160 °C) with release of acetonitrile.When heated to decomposition it emits toxic fumes of /nitrogen oxide and hydrogen cyanide/. |
| Schmelzpunkt | 151 °F (USCG, 1999)66 °C65 °C |
| Dampfdruck | 0.03 [mmHg]0.1 mm Hg ( 100 °C) |
| Physical Description | Cyanoacetic acid is a yellow-brown liquid with an unpleasant odor. Sinks and mixes with water. (USCG, 1999)White hygroscopic solid[Hawley] White crystalline solid[MSDSonline] |
| Dissociation Constants | pKa = 2.45 at 25 °C |
| Other Experimental Properties | Hygroscopicdecomp at 160 °C into CO2 and acetonitrile |
| Brechungsindex | 1.3764 (estimate) |
| Flammpunkt | 226 °F |
| Lagerbedingungen | Store below +30°C. |
| pKa (Säurekonstante) | 2.45(at 25℃) |
| Aggregatzustand | Adhering Crystalline Solid |
| Farbe | White to light beige |
| pH | 1.6 (50g/l, H2O, 20℃) |
| Merck | 14,2689 |
| BRN | 506325 |
| Dielektrizitätskonstante | 33.0(4℃) |
| InChI | 1S/C3H3NO2/c4-2-1-3(5)6/h1H2,(H,5,6) |
| InChIKey | MLIREBYILWEBDM-UHFFFAOYSA-N |
| SMILES | OC(=O)CC#N |
| LogP (Verteilungskoeffizient) | -0.76 |
| CAS Datenbank | 372-09-8(CAS DataBase Reference) |
| NIST chemische Informationen | Acetic acid, cyano-(372-09-8) |
| EPA chemische Informationen | Cyanoacetic acid (372-09-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 1.2% (3 of 245) of reports.DangerH302+H332 (21.2%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oralacute toxicity, inhalation]H302 (98.4%): Harmful if swallowed [Warning Acute toxicity, oral]H314 (98.8%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]H318 (67.3%): Causes serious eye damage [Danger Serious eye damage/eye irritation]H332 (86.9%): Harmful if inhaled [Warning Acute toxicity, inhalation]H412 (12.2%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 245 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 3 of 245 reports by companies.There are 21 notifications provided by 242 of 245 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: Acetic acid, cyano-Status: Active Update: 16-04-2014 https://echa.europa.eu/registration-dossier/-/registered-dossier/7134Status: Active Update: 31-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13908Cyanoacetic acid: Does not have an individual approval but may be used under an appropriate group standard |
| DOT-Kennzeichnung | Corrosive |
| Brandgefahren | Special Hazards of Combustion Products: Toxic oxides of nitrogen and toxic and flammable acetonitrile vapors may form in fire. (USCG, 1999) |
| Brandpotenzial | Combustible solid. When heated to decomp, emits ... flammable acetonitrile vapor. |
| Gesundheitsgefahren | Contact irritates eyes and may irritate skin. (USCG, 1999) |
| Gefahrenübersicht | A corrosive substance that can cause injury to the skin and eyesA respiratory tract irritantEmergency treatment: see Acetonitrile. [HSDB] A skin and eye irritant[CAMEO] A corrosive substance that can cause injury to the skin, eyes, and respiratory tractInhalation may cause chemical pneumonitis[MSDSonline] |
| Reaktive Gruppe | Acids, CarboxylicNitrilesAcids, Weak |
| Reactivity Profile | White, moderately toxic solid, combustible. When heated to decomposition it emits toxic fumes of nitrile and oxides of nitrogen. A stirred mixture with furfuryl alcohol exploded violently upon heating [MCA Case History No 858]. |
| Luftstandards | This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Cyanoacetic acid is produced, as an intermediate or a final product, by process units covered under this subpart. |
| Air and Water Reactions | Water soluble. |
| Other Hazardous Reactions | Combustion may produce irritants and toxic gases. |
| Toxic Combustion Products | Combustion may produce irritants and toxic gases. |
| Brandbekämpfung | Fire Extinguishing Agents: Water, foam, dry chemical, carbon dioxide (USCG, 1999) |
| Erste Hilfe | INHALATION: move to fresh air.INGESTION: give large amounts of waterget medical attention.EYES: flush with water for at least 15 min.SKIN: flush with water. (USCG, 1999) |
| Brandbekämpfungsverfahren | ... Water ... effective in controlling firehowever, resulting liquid ... extremely corrosive ...Use water spray, dry chemical, or carbon dioxide. Use water spray to keep fire-exposed containers cool. Control corrosive runoff and isolate discharged material for proper disposal. Approach fire from upwind to avoid hazardous vapors and toxic decomposition products. |
| Lagerbedingungen | Protect against physical damage. Separate from other storage ... /Store/ away from any area where fire hazard may be acute. Outside or detached storage is preferred ...Store in a cool, dry, well-ventilated location. Separate from acids, alkalies, oxidizing materials, reducing agents. |
| Reinigungsverfahren | Stop or control the leak, if this can be done without undue risk. Absorb in noncombustible material for proper disposal. |
| Freisetung ohne Brand | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2024) |
| Entsorgungsverfahren | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Preventive Measures | SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directionsalso, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024) |
| Personal Protective Equipment (PPE) | Dust maskgoggles or face shieldrubber gloves (USCG, 1999)... Full protective clothing except that in absence of heat self-contained breathing apparatus is not required.Wear special protective clothing and positive pressure self-contained breathing apparatus. |
| Treatment | Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97) |
| Gesundheitliche Auswirkungen | Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97) |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that cyanoacetic acid is expected to have very high mobility in soil(SRC). Furthermore, the pka of cyanoacetic acid is 2.45(3), indicating it will exist as an anion under environmental conditions and anions generally have greater mobility in soils than neutral compounds(4). Volatilization from moist soil surfaces will not be an important environmental fate process since anions do not volatilize(SRC). The potential for volatilization of cyanoacetic acid from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 0.035 mm Hg determined from a fragment constant method(5). Cyanoacetic acid was readily degraded in 2 weeks using an activated sludge inoculum and the Japanese MITI test, suggesting that it will be susceptible to biodegradation in soil(6).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that cyanoacetic acid is not expected to adsorb to suspended solids and sediment(SRC). The pka of cyanoacetic acid is 2.45(3), indicating it will exist as an anion under environmental conditions. Volatilization from water surfaces is not an important environmental fate process since anions do not volatilize(SRC). According to a classification scheme(4), an estimated BCF of 3(SRC), from a log Kow of -0.76(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Cyanoacetic acid is highly reactive in chlorinated water, rapidly degrading to dichloroacetic acid, dichloromalonic acid, and trichloroacetic acid at pH 4-10(7). Cyanoacetic acid was readily degraded in 2 weeks using an activated sludge inoculum and the Japanese MITI test, suggesting that it will be susceptible to biodegradation in water(8).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cyanoacetic acid, which has an estimated vapor pressure of 0.035 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase cyanoacetic acid 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 25 days(SRC), calculated from its rate constant of 6.5X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.Other Poison - Chemical AsphyxiantDermatotoxin - Skin burns.Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors. |
| Expositionspfade | Oral (L96)inhalation (L96)dermal (L96) |
| Toxizitätsübersicht | Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97) |
| Signs and Symptoms | Cyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97) |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc for cyanoacetic acid can be estimated to be 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that cyanoacetic acid is expected to have very high mobility in soil(SRC). In addition, the pKa of cyanoacetic acid is 2.45(3), indicating that this compound will exist primarily as an anion in the environment, and anions generally possess higher mobility in soil than their neutral counterpart(4). |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ Corrosive. Causes severe eye and skin burns. May be harmful if absorbed through skin or inhaled. Irritating to skin, eyes, and respiratory system./OTHER TOXICITY INFORMATION/ ...Acetonitrile /formed when cyanoacetic acid is heated/ is irritating to skin... high concentration ...rapidly fatal. |
| Artificial Pollution Sources | Cyanoacetic acid's production and use for the manufacture of the fungicide cymoxanil, the cough remedy dextromethorphan(1), and the production of barbital(2) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: Cyanoacetic acid, present at 100 mg/L, reached 90% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(1). |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| F | 3-10-21 |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3261 8/PG 2 |
| Zollcode | 2926 90 70 |
| RTECS-Nr. | AG3675000 |
| R-Sätze (R) | 22-31-34-52/53-20/22 |
| Toxizität | LD50 orally in Rabbit: 1500 mg/kg LD50 dermal Rabbit > 2000 mg/kg |
| Gefahrensymbole | C |
| Sicherheitshinweise (S) | 26-36/37/39-45-61-20 |
| Gefahrenklasse | 8Acute Tox. 4 InhalationAcute Tox. 4 OralEye Dam. 1Skin Corr. 1B |
| Verpackungsgruppe | II |
| Lagerklasse | 8A - Combustible corrosive hazardous materials |
| Gefahrstoffdaten | 372-09-8(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Cyanoacetic acid is an organic compound. It is a white, hygroscopic solid. The compound contains two functional groups, a nitrile (C≡N) and a carboxylic acid. It is a precursor to cyanoacrylates, components of adhesives.Cyanoacetic acid is used in pharmaceutical industry for producing vitamin B6 and caffeine. It is also used in making dyes, agricultural chemicals, and in the synthesis of phenylacetic acid esters. It acts as a precursor cyanoacrylates viz. ethyl cyanoacrylate.
Verwenden
Cyanoacetic acid was used in the synthesis of N-piperidine-cyanacetamide and N-morpholyl-cyanacetamide. It was also used in the preparation of a panchromatic dye for dye-sensitized solar cells.
Herstellung & Synthese
synthetische
Cyanoacetic acid is prepared by treatment of chloroacetate salts with sodium cyanide followed by acidification. Electrosynthesis by cathodic reduction of carbon dioxide and anodic oxidation of acetonitrile also affords cyanoacetic acid.