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N,N'-Methylendiacrylamid
MBA · BIS · METHYLENEBISACRYLAMIDE · BISACRYLAMIDE · N, N-METHYLENE-BIS-ACRYLAMIDE · N,N'-Methylenediacrylamide · napp · N,N-Methylenebisa
Identifikatoren & physikalische Daten
| CAS No. | 110-26-9 |
|---|---|
| Summenformel | C7H10N2O2 |
| Durchschnittliche Molmasse | 154,17 g/mol |
| Monoisotopische Masse | 154,07422757 g/mol |
| SMILES | C=CC(=O)NCNC(=O)C=C |
| InChIKey | ZIUHHBKFKCYYJD-UHFFFAOYSA-N |
| PubChem CID | 8041 |
| ChEMBL | CHEMBL1401480 |
| EC No. | 203-750-9 |
| DTXSID | DTXSID8025595 |
| Lokaler Name | N,N'-Methylendiacrylamid |
Chemische & physikalische Eigenschaften
| XLogP | 0,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 58,2 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 167 |
| Dichte | 1.235 at 86 °F (NTP, 1992) - Denser than waterwill sink1.235 @ 30°C |
| Löslichkeit | 0.1 to 1 mg/mL at 64 °F (NTP, 1992)H2O: 20 mg/mL at 20 °C, clear, colorless0.01-0.1 g/100 mL at 18 ºC |
| Schmelzpunkt | 365 °F (with decomposition) (NTP, 1992)>300 °C(lit.) |
| Dampfdichte | 5.31 (NTP, 1992) - Heavier than airwill sink (Relative to Air)5.31 (vs air) |
| Physical Description | N,n'-methylenebisacrylamide is a white crystalline powder with a neutral odor. (NTP, 1992)Dry PowderWhite solid[CAMEO] |
| Collision Cross Section | 138.1 Ų [M+Na]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID8025595] |
| Siedepunkt | 277.52°C (rough estimate) |
| Dampfdruck | 0-0.073Pa at 20-84.85℃ |
| Brechungsindex | 1.4880 (estimate) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | powder |
| pKa (Säurekonstante) | 13.07±0.46(Predicted) |
| Farbe | White |
| Geruch | Odorless |
| pH | >=5.0 (25g/l, H2O, 20℃) |
| BRN | 1706297 |
| Stabilität | Light Sensitive |
| InChI | 1S/C7H10N2O2/c1-3-6(10)8-5-9-7(11)4-2/h3-4H,1-2,5H2,(H,8,10)(H,9,11) |
| InChIKey | ZIUHHBKFKCYYJD-UHFFFAOYSA-N |
| SMILES | C=CC(=O)NCNC(=O)C=C |
| LogP (Verteilungskoeffizient) | -1.52--0.08 at 24-25℃ and pH4-10 |
| Oberflächenspannung | 70.2-70.3mN/m at 1g/L and 20℃ |
| CAS Datenbank | 110-26-9(CAS DataBase Reference) |
| NIST chemische Informationen | 2-Propenamide, n,n'-methylenebis-(110-26-9) |
| EPA chemische Informationen | N,N'-Methylenebisacrylamide (110-26-9) |
| Absorption | ≤0.2 at 290 at 1% |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH340: May cause genetic defects [Danger Germ cell mutagenicity]P203, P280, P318, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Chemical: 2-Propenamide, N,N'-methylenebis-Hazard Traits - GenotoxicityAuthoritative List - EC Annex VI CMRs - Cat. 1BReport - if used as a fragrance or flavor ingredient2-Propenamide, N,N'-methylenebis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenamide, N,N'-methylenebis- 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: 10-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/210362-Propenamide, N,N'-methylenebis: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | Evaluation - 2-Propenamide, N,N'-methylenebis- (N,N'-methylenebisacrylamide) |
| Brandgefahren | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this type of compound may include irritation and redness of the skin, irritation of the eyes, drowsiness, tingling sensation, fatigue, weakness, stumbling, slurred speech and shaking. Chronic exposure to this type of compound may lead to muscular weakness, incoordination, skin rashes, excessive sweating of the hands and feet, cold hands and peeling of the skin.ACUTE/CHRONIC HAZARDS: This compound is toxic by ingestion. It may be harmful by inhalation or skin absorption. Solutions may be absorbed through the IMMEDIATELY leave the contaminated areatake deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be usedif not available, use a level of protection greater than or equal to that advised under Protective Clothing. (NTP, 1992) |
| Gefahrenübersicht | May cause skin and eye irritation and symptoms indicative of nervous system effects[NTP] May cause irritationHarmful by ingestion and inhalationMay cause reproductive disorders, based on animal studies[Sigma-Aldrich MSDS] See Acrylamide. |
| Reaktive Gruppe | Amides and ImidesHydrocarbons, Aliphatic Unsaturated |
| Reactivity Profile | N,N'-METHYLENEBISACRYLAMIDE is incompatible with strong oxidizers, strong acids and strong bases. (NTP, 1992) |
| Air and Water Reactions | Very slightly water soluble. |
| Hazard Classes and Categories | Acute Tox. 3 (54.4%)Acute Tox. 4 (45.6%)Acute Tox. 4 (35.3%)Skin Sens. 1 (19.1%)Eye Dam. 1 (19.1%)Acute Tox. 4 (51.1%)Muta. 1B (54.6%)Carc. 1B (35.1%)Carc. 2 (19.3%)Repr. 1B (19.1%)Repr. 2 (31.4%)STOT RE 1 (54.4%)Acute toxicity (Oral) - Category 3Germ cell mutagenicity - Category 1BReproductive toxicity - Category 1BSpecific target organ toxicity - Single exposure - Category 1 (nervous system, reproductive organs (male)) |
| Brandbekämpfung | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992) |
| 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.SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.INHALATION: IMMEDIATELY leave the contaminated areatake deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be usedif not available, use a level of protection greater than or equal to that advised under Protective Clothing.INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992) |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.STORAGE PRECAUTIONS: You should store this material under ambient temperatures away from oxidizers, acids and bases. (NTP, 1992) |
| Protective Action Criteria (PAC) | 1.2 [mg/m3]13 [mg/m3]77 [mg/m3] |
| Personal Protective Equipment (PPE) | RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992) |
| Toxicity Data | LC (rat) > 41 ppm/6hr |
| F | 8 |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2811 |
| Zollcode | 29241900 |
| RTECS-Nr. | AS3678000 |
| R-Sätze (R) | 20/22-20/21/22-36/37/38 |
| Toxizität | LD50 orally in Rabbit: 390 mg/kg |
| Gefahrensymbole | Xn,Xi |
| Sicherheitshinweise (S) | 22-36/37-36-26 |
| Gefahrenklasse | 6.1(b)Acute Tox. 3 OralAcute Tox. 4 DermalCarc. 1BMuta. 1BRepr. 2STOT RE 1 Oral |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
Anwendungen & Verwendung
Verwenden
N,N'-Methylenebisacrylamide is used in the preparation of polyacrylamide gels for electrophoretic separation of nucleic acids and proteins. It has also been used as a test compound for studying the biochemical isolation of insoluble Tau in transgenic mouse models of tauopathy by examining the two main isolation methods sarkosyl and formic acid extraction.