3-Hydroxypropiononitril
2-CYANOETHANOL · ETHYLENE CYANOHYDRIN · Cyanoethanol · HYDRACRYLONITRILE · Hydroxyacrylonitrile · Hydroxypropanenitrile · 3-HYDROXYPROPIONONITRILE · NSC 2598
Identifikatoren & physikalische Daten
| CAS No. | 109-78-4 |
|---|---|
| Summenformel | C3H5NO |
| Durchschnittliche Molmasse | 71,08 g/mol |
| Monoisotopische Masse | 71,03711378 g/mol |
| SMILES | N#CCCO |
| InChIKey | WSGYTJNNHPZFKR-UHFFFAOYSA-N |
| PubChem CID | 8011 |
| ChEBI | CHEBI:234504 |
| EC No. | 203-704-8 |
| DTXSID | DTXSID1025433 |
| Lokaler Name | 3-Hydroxypropiononitril |
Chemische & physikalische Eigenschaften
| XLogP | -0,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 44 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 5 |
| Formalladung | 0 |
| Komplexität | 51 |
| LogP (Verteilungskoeffizient) | log Kow= -0.94 |
| Dichte | 1.047 at 68 °F (USCG, 1999) - Denser than waterwill sink1.0404 @ 25 °CRelative density (water = 1): 1.041.04 g/mL at 25 °C (lit.) |
| Color/Form | WATER-WHITE LIQUIDStraw-colored liquid |
| Löslichkeit | greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)Miscible in ethanolsoluble in chloroformslightly soluble in ethyl ether.Miscible with acetone, methyl ethyl ketone, ethanol, chloroform, and diethyl etherinsoluble in benzene, carbon tetrachloride, and naphtha.Miscible with acetone, methyl ethyl ketone, ethyl alcohol. Slightly sol in ether (2.3% w/w @ 15 °C). Insol in benzene, petr ether, carbon disulfide, carbon tetrachloride.In water, 1X10+6 mg/l @ 20 °CSolubility in water: misciblediethyl ether: slightly soluble2.3% (w/w) at 15°C(lit.)>=10 g/100 mL at 20 ºC |
| Flammpunkt | greater than 265 °F (NTP, 1992)265 °F (129 °C) (Open cup)129 °C o.c.>230 °F |
| Siedepunkt | 442 °F at 760 mmHg (slight decomposition) (NTP, 1992)221 °C228 °C (lit.) |
| Decomposition | WHEN HEATED OR ON CONTACT WITH ACID OR ACID FUMES, IT EMITS HIGHLY TOXIC FUMES OF CYANIDES.228 °C |
| Schmelzpunkt | -51 °F (NTP, 1992)-46 °C-46 °C (lit.) |
| Dampfdichte | 2.5 (NTP, 1992) - Heavier than airwill sink (Relative to Air)2.45 (AIR= 1)Relative vapor density (air = 1): 2.452.5 (vs air) |
| Dampfdruck | 0.08 mmHg at 77 °F20 mmHg at 243 °F (NTP, 1992)0.08 [mmHg]0.08 MM HG @ 25 °CVapor pressure, Pa at 25 °C: 10.7<0.1 mm Hg ( 20 °C) |
| Brechungsindex | Index of refraction: 1.4248 @ 20 °C/Dn20/D 1.425(lit.) |
| Physical Description | Ethylene cyanohydrin is a colorless to yellow-brown liquid with a weak odor. Sinks and mixes with water. (USCG, 1999)Straw-colored liquid[Hawley] Colorless to yellow-brown liquid[CAMEO]COLOURLESS-TO-YELLOW LIQUID. |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | 13.82±0.10(Predicted) |
| Wichte | 1.047 (20/4℃) |
| Farbe | Clear slightly yellow to yellow |
| pH | 3.0-4.5 (H2O, 20℃)(undiluted) |
| Explosionsgrenze | 12.1% |
| Merck | 14,3794 |
| BRN | 635773 |
| Henry-Konstante | 1.3×103 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Stabilität | Stable. Flammable. Incompatible with strong oxidizing agents. Reacts with water or steam to release toxic vapours. Reacts violently with acids, amines, inorganic bases. Corrodes mild steel. |
| InChI | 1S/C3H5NO/c4-2-1-3-5/h5H,1,3H2 |
| InChIKey | WSGYTJNNHPZFKR-UHFFFAOYSA-N |
| SMILES | OCCC#N |
| LogP (Verteilungskoeffizient) | -0.94 at 20℃ |
| CAS Datenbank | 109-78-4(CAS DataBase Reference) |
| NIST chemische Informationen | Propanenitrile,3-hydroxy-(109-78-4) |
| EPA chemische Informationen | Ethylene cyanohydrin (109-78-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 75.4% (144 of 191) of all reports.WarningH315 (24.6%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (24.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (24.1%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 191 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 144 of 191 reports by companies.There are 6 notifications provided by 47 of 191 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: Propanenitrile, 3-hydroxy-Status: Active Update: 02-10-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/23661Status: Cease Manufacture Update: 30-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24268Hydracrylonitrile: 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 |
| Brandgefahren | Special Hazards of Combustion Products: Toxic gases are generated when heated.Behavior in Fire: Decomposes, generating toxic gases (USCG, 1999)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
Anwendungen & Verwendung
Occurrence
3-Hydroxypropionitrile does not occur as a natural product. Nevertheless, it may enter natural waters because it is present in concentrations between 2000 and 4000 p.p.m. in polyacrylimide polymers (Ikeda 1978) which are used as coagulants in water and wastewater purification. 3-Hydroxypropionitrile may leach from the polymer and enter the water being treated with the coagulant. Since acrylimide polymers are generally present at concentrations up to 1 p.p.m. during water purification (Sauerhoff et al 1976), if all the 3-Hydroxypropionitrile were extracted from the polymer, the concentration in water might be as high as 4 p.p.b. Fortunately, up to 99% of the 3-Hydroxypropionitrile may be removed by treatment with activated carbon in countercurrent multistage fluidized beds (Sasaoka 1975).
Verwenden
3-Hydroxypropionitrile has been used as polar solvent to investigate the orientation of the phospholipid at the surface of the polar solvents by neutral impact collision ion scattering spectroscopy and as a reagent for carboxyl protection in peptide synthesis. It has been used also in solid state composite electrolyte for dye-sensitized solar cells.