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Nicotinonitril
NICOTINONITRILE · 3-PYRIDINECARBONITRILE · Pyridine-3-carbonitrile · 3-Cyjanopirydyna · 3-Azabenzonitrile · BETA-CYANOPYRIDINE · NICOTINIC ACID NITRILE · Nicotinamide EP Impurity B
Identifikatoren & physikalische Daten
| CAS No. | 100-54-9 |
|---|---|
| Summenformel | C6H4N2 |
| Durchschnittliche Molmasse | 104,11 g/mol |
| Monoisotopische Masse | 104,03744813 g/mol |
| SMILES | N#Cc1cccnc1 |
| InChIKey | GZPHSAQLYPIAIN-UHFFFAOYSA-N |
| PubChem CID | 79 |
| ChEMBL | CHEMBL3181972 |
| ChEBI | CHEBI:86556 |
| EC No. | 202-863-0 |
| DTXSID | DTXSID1026665 |
| Lokaler Name | Nicotinonitril |
Chemische & physikalische Eigenschaften
| XLogP | 0,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 36,7 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 111 |
| Stoffklassen | Nitrogen Compounds -> Nitriles |
| SpringerMaterials Properties | Boiling point |
| LogP (Verteilungskoeffizient) | log Kow = 0.36 |
| Dichte | 1.1590 @ 25 °C |
| Color/Form | NEEDLES FROM PETROLEUM ETHERColorless liquid |
| Löslichkeit | Soluble in hot petroleum etherSoluble in alcohol, ether, and benzene.In water, 1.35X10+5 mg/l @ 20 °C140g/l140 g/L (20 ºC) |
| Flammpunkt | 87 °C184 °F |
| Siedepunkt | 206.9 °C201 °C(lit.) |
| Schmelzpunkt | 51 °C48-52 °C(lit.) |
| Dampfdruck | 0.29 [mmHg]0.296 mm Hg @ 25 °C |
| Henry-Konstante | Henry's Law constant = 2.74X10-7 atm-cu m/mole @ 25 °C3.6×101 mol/(m3Pa) at 25℃, Abraham et al. (1994) |
| Physical Description | Other SolidColorless liquid[Hawley] Off-white crystalline solid[MSDSonline] |
| Brechungsindex | 1.5242 (estimate) |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Aggregatzustand | Crystalline Mass, Crystals or Chunks |
| pKa (Säurekonstante) | pK1:1.45(+1) (25°C) |
| Farbe | Colorless or white to yellow |
| BRN | 107711 |
| Stabilität | Incompatible with strong oxidizing agents, strong reducing agents, strong acids, strong bases. |
| InChI | 1S/C6H4N2/c7-4-6-2-1-3-8-5-6/h1-3,5H |
| InChIKey | GZPHSAQLYPIAIN-UHFFFAOYSA-N |
| SMILES | N#Cc1cccnc1 |
| CAS Datenbank | 100-54-9(CAS DataBase Reference) |
| NIST chemische Informationen | 3-Pyridinecarbonitrile(100-54-9) |
| EPA chemische Informationen | 3-Pyridinecarbonitrile (100-54-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 85 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H302: Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Chemical: 3-Pyridinecarbonitrile3-Pyridinecarbonitrile is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 3-Pyridinecarbonitrile are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 10-12-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/51493-Pyridinecarbonitrile: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | A skin, eye, and mucous membrane irritantEmergency treatment: PyridinePyridine is an irritant that causes CNS depression after ingestion of 1/2 cup or inhalation of 6-12 ppmIt can cause liver and kidney injury[HSDB] Causes respiratory depression and liver changes in lethal-dose studies of rats[RTECS] An irritantHarmful if swallowed[Alfa Aesar MSDS] See m-Phthalodinitrile. |
| TSCA-Anforderungen | Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 3-Pyridinecarbonitrile is included on this list. |
| Hazard Classes and Categories | Acute Tox. 4 (100%)Acute toxicity (Oral) - Category 4 |
| Skin, Eye, and Respiratory Irritations | Pyridine and its derivatives cause local irritation on contact with the skin, mucous membranes and cornea. /Pyridine and its derivatives/ |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| 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. |
| Personal Protective Equipment (PPE) | Depending on the extent of possible contact, workers should be provided with personal protective equipment. A charcoal gas mask canister respirator has been found to be effective against a 2% pyridine concentration at 30 l/min for 1 hr. Rubber and plastic gloves should not be relied upon to prevent skin contact because pyridine and many of its derivatives penetrate these materials ... . /Pyridine, homologs, and derivatives/ |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 37(SRC), determined from a measured log Kow of 0.36(2) and a regression-derived equation(3), indicates that 3-pyridinecarbonitrile is expected to have very high mobility in soil(SRC). Volatilization of 3-pyridinecarbonitrile from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 2.74X10-7 atm-cu m/mole(4). 3-Pyridinecarbonitrile is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.296 mm Hg(5). In water, the maximum pseudo-first-order rate constant and half-life for 3-pyridinecarbonitrile in an anoxic sediment slurry from the estuary of the Tansui River (Guandu, Taipei) were 9.41 per day and 1.7 hrs, respectively(6) which suggests that 3-pyridinecarbonitrile may biodegrade in soil at least under anaerobic conditions(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 37(SRC), determined from a measured log Kow of 0.36(2) and a regression-derived equation(3), indicates that 3-pyridinecarbonitrile is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 2.74X10-7 atm-cu m/mole(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The maximum pseudo-first-order rate constant and half-life for 3-pyridinecarbonitrile in an anoxic sediment slurry from the estuary of the Tansui River (Guandu, Taipei) were 9.41 per day and 1.7 hrs, respectively(7) which suggests that 3-pyridinecarbonitrile may degrade in the environment at least under anaerobic conditions(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3-pyridinecarbonitrile, which has a vapor pressure of 0.296 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase 3-pyridinecarbonitrile 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 246 days(SRC), calculated from its rate constant of 6.53X10-14 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). |
| Unerwünschte Wirkungen | Neurotoxin - Other CNS neurotoxin |
| Soil Adsorption/Mobility | The Koc of 3-pyridinecarbonitrile is estimated as 37(SRC), using a measured log Kow of 0.36(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 3-pyridinecarbonitrile is expected to have very high mobility in soil(SRC). |
| Artificial Pollution Sources | 3-Pyridinecarbonitrile's production and use in organic synthesis(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | ANAEROBIC: The maximum pseudo-first-order rate constant and half-life for 3-pyridinecarbonitrile in an anoxic sediment slurry from the estuary of the Tansui River (Guandu, Taipei) were 9.41 per day and 1.7 hrs, respectively(1). 3-Pyridinecarbonitrile was not transformed in the sterile control sediment slurry(1) which suggests that 3-pyridinecarbonitrile may degrade in the environment at least under anaerobic conditions(SRC). |
| Environmental Bioconcentration | An estimated BCF of 3 was calculated for 3-pyridinecarbonitrile(SRC), using a log Kow of 0.36(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for 3-pyridinecarbonitrile is 2.74X10-7 atm-cu m/mole(1). This Henry's Law constant indicates that 3-pyridinecarbonitrile is not expected to volatilize from water and moist soil surfaces(2). 3-Pyridinecarbonitrile is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.296 mm Hg(3). |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of 3-pyridinecarbonitrile with photochemically-produced hydroxyl radicals has been estimated as 6.53X10-14 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 246 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1). 3-Pyridinecarbonitrile is expected to undergo slow hydrolysis in the environment based upon the slow hydrolysis of other aromatic nitriles, eg, benzonitrile(2). 3-Pyridinecarbonitrile is also not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm)(SRC). |
| Probable Routes of Human Exposure | Occupational exposure to 3-pyridinecarbonitrile may occur through inhalation and dermal contact with this compound at workplaces where 3-pyridinecarbonitrile is produced or used. (SRC) |
| Environmental Fate/Exposure Summary | 3-Pyridinecarbonitrile's production and use in organic synthesis may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 0.296 mm Hg at 25 °C indicates 3-pyridinecarbonitrile will exist solely as a vapor in the ambient atmosphere. Vapor-phase 3-pyridinecarbonitrile will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicalsthe half-life for this reaction in air is estimated to be 246 days. If released to soil, 3-pyridinecarbonitrile is expected to have very high mobility based upon an estimated Koc of 37. Volatilization from moist soil surfaces is not expected to be an important fate process based upon a Henry's Law constant of 2.74X10-7 atm-cu m/mole. If released into water, 3-pyridinecarbonitrile is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. The maximum pseudo-first-order rate constant and half-life for 3-pyridinecarbonitrile in an anoxic sediment slurry were 9.41 per day and 1.7 hrs, respectively which suggests that 3-pyridinecarbonitrile may rapidly biodegrade in the environment at least under anaerobic conditions(SRC). Volatilization from water surfaces is not expected to be an important fate process based upon this compound's Henry's Law constant. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Chemical hydrolysis is expected to be slow. Occupational exposure to 3-pyridinecarbonitrile may occur through inhalation and dermal contact with this compound at workplaces where 3-pyridinecarbonitrile is produced or used. (SRC) |
| EPA Provisional Peer-Reviewed Toxicity Values | NicotinonitrilePDF Document2004 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29333999 |
| RTECS-Nr. | QT3030000 |
| R-Sätze (R) | 22-36/37/38 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 22-24/25-36/37/39-26 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 100-54-9(Hazardous Substances Data) |
| Gefahrenklasse | Acute Tox. 4 OralEye Dam. 1Skin Irrit. 2 |
Anwendungen & Verwendung
Verwenden
3-Cyanopyridine is used in the preparation of arylthiazolines and arylimidazolines via dibromodimethylhydantoin-catalyzed condensation of aryl nitriles with ethylene diamine or aminoethanethiol.