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N-(1,1-Dimethyl-3-oxo-butyl)-2-propenamid

N-(1,1-Dimethyl-3-oxobutyl)acrylamide

HCID 17888
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Grundinformationen

CAS
2873-97-4
Standard-SMILES
C=CC(=O)NC(C)(C)CC(C)=O
InChIKey
OMNKZBIFPJNNIO-UHFFFAOYSA-N
Summenformel
C9H15NO2
Durchschnittliche Molmasse
169,22 g/mol
Monoisotopische Masse
169,11027872

Überblick

Diacetone acrylamide appears as white crystals. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
N-(1,1-Dimethyl-3-oxobutyl)acrylamide
IUPAC
N-(2-methyl-4-oxopentan-2-yl)prop-2-enamide
Lokaler Name
N-(1,1-Dimethyl-3-oxo-butyl)-2-propenamid
Englischer Name
Diacetone acrylamide
Summenformel
C9H15NO2
Molmasse
169.22

Namen und Synonyme

N-(1,1-Dimethyl-3-oxobutyl)acrylamideDAAm compoundRefChem:586138DIACETONE ACRYLAMIDE2873-97-4DiacetoneacrylamideN-(2-Methyl-4-oxopentan-2-yl)acrylamide2-Propenamide, N-(1,1-dimethyl-3-oxobutyl)-N-(2-methyl-4-oxopentan-2-yl)prop-2-enamideN-(1,1-Dimethyl-3-oxobutyl)-2-propenamideAcrylamide, N,N-diacetonyl-Acrylamide, N-(1,1-dimethyl-3-oxobutyl)-
Weitere Namen anzeigen
DAAMDAACmcSodiumSalt(EdifasB)Diacetone acryL5-oxo-2-hexenamideDIAECTONEACRYLAMIDEDiacetonyl acrylamide
CCRIS 5898DTXSID1024916N-(2-(2-Methyl-4-oxopentyl))acrylamideMFCD00008788DAAADIACETONE ACRYLAMIDE [HSDB]WLN: 1V1X1&1&MV1U1ZINC1717544

Datenbank-Bezeichner

CAS
2873-97-4

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,4
Polarare Oberfläche (TPSA)
46,2 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
4
Schwere Atome
12
Formalladung
0
Komplexität
207

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Other Organic Compounds
Color/FormWhite crystalline solid
Solubility · 3 Einträge

Very soluble (NTP, 1992)

Highly sol in water and most organic solvents

Soluble in chloroform

Boiling Point · 2 Einträge

248 °F at 8 mmHg (NTP, 1992)

120 °C @ 8 mm Hg

DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Melting Point · 2 Einträge

135 to 136 °F (NTP, 1992)

57-58 °C

Vapor Pressure0.000579 [mmHg]
Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical Description · 3 Einträge

Diacetone acrylamide appears as white crystals. (NTP, 1992)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 18% (65 of 362) of reports.

Warning

H302 (82%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 362 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: 2-Propenamide, N-(1,1-dimethyl-3-oxobutyl)-

2-Propenamide, N-(1,1-dimethyl-3-oxobutyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenamide, N-(1,1-dimethyl-3-oxobutyl)- 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)

REACH registered substance: N-(1,1-dimethyl-3-oxobutyl)acrylamide (EC: 220-713-2)

2-Propenamide, N-(1,1-dimethyl-3-oxobutyl)-: Does not have an individual approval but may be used under an appropriate group standard

Health HazardsACUTE/CHRONIC HAZARDS: Toxic. Irritant. Flammable. Hazardous decomposition products. (NTP, 1992)
Hazards SummaryToxic by ingestion; [HSDB] Causes somnolence and convulsions in lethal-dose feeding studies of rats; [RTECS] An irritant; [CAMEO] An irritant; Effects in high-dose animal studies include convulsions; [MSDSonline]
Reactive GroupAmides and Imides
Reactivity AlertsPolymerizable

Chemie und Industrie

Verwendung und Herstellung

Uses · 6 Einträge

Used to make coatings, laminates, sealers, adhesives, and lubricating oils; to impart water tolerance and vapor permeability to copolymer films; as cross-linking agent in polyester resins; in color photography; in orthopedic bandages; in air sprays; [HSDB] Used as adhesion improver for cellulosics, concrete, and glass; [Hawley]

Textiles (Fiber & Fabric Manufacturing) [Category: Industry]

In mfr of coatings, laminates, sealers, adhesives, lubricating oils

Imparts water tolerance and vapor permeability to copolymer films; cross-linking agent in polyester resins; color photography

ORTHOPEDIC BANDAGE COMPRISING DIACETONE ACRYLAMIDE

IN AIR SPRAYS

U.S. Imports(1979) 2.52X10+6 GRAMS (PRINCPL CUSTMS DISTS)
U.S. Production · 3 Einträge

2023: 1,000,000 - <2,500,000 lb

(1977) NOT PRODUCED COMMERCIALLY IN US

(1979) NOT PRODUCED COMMERCIALLY IN US

Industry UsesOther
Methods of Manufacturing · 3 Einträge

REACTION OF ACRYLONITRILE WITH ACETONE IN PRESENCE OF CONCENTRATED SULFURIC ACID; REACTION OF ACRYLONITRILE WITH 1,1-DIMETHYL-3-OXOBUTANOL VIA RITTER REACTION

Prepd by reaction of acrylonitrile with acetone in presence of concn sulfuric acid: Coleman et al, J Polym Sci 3a, 1601 (1965); Coleman, US patent 3,277,056 (1966 to Lubrizol).

N-Substituted acrylamides may also be prepared from acetylene, carbon monoxide, and an amine using an iron or nickel carbonyl catalyst.

Formulations/PreparationsPurity 99+%
General Manufacturing Information · 3 Einträge

Paint and Coating Manufacturing

2-Propenamide, N-(1,1-dimethyl-3-oxobutyl)-: ACTIVE

Similar to acrylic esters in polymerization behavior. Forms high mol wt polymers in bulk, soln, or emulsion. Esp suitable for electropolymerization.

Zugehörige Reaktionen

4
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 381614
HRID 381614als Eduktuspto-grants-2001_10
Reaktionsgleichung von HRID 1390851
HRID 1390851als Eduktuspto-grants-1979_02
Reaktionsgleichung von HRID 1390852
HRID 1390852als Eduktuspto-grants-1979_02
Reaktionsgleichung von HRID 2058305
HRID 2058305als Eduktuspto-grants-1980_07

Notizen zur Verbindung

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PubChem CID
17888
DTXSID
DTXSID1024916
ChEMBL
CHEMBL3183854
UNII
3Z8J3430Z2
EC Number
220-713-2
Nikkaji
J7.924C

Large Crystals; Dry Powder; Liquid

White hygroscopic solid; [Merck Index] White or yellow crystalline solid; [MSDSonline]

Stability/Shelf Life · 2 Einträge

HAS LONG SHELF LIFE; SHOWS NO POLYMERIZATION ON PROLONGED STORAGE.

50% NEUTRAL WATER SOLN IS STABLE @ PH 7.5-7.7 FOR UP TO 6 MO; HIGHLY REACTIVE VINYL MONOMER.

Collision Cross Section145.2 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID1024916]
Other Experimental PropertiesHygroscopic

Physikochemische Eigenschaften

Schmelzpunkt
54 · 54-56 °C (lit.)
Siedepunkt
120 °C · 120 °C (8 mmHg)
Dichte
1.0873 · 1.0873 (rough estimate)
Dampfdruck
0.109 Pa · 0.109Pa at 20℃
Brechungsindex
1.42 · 1.4200 (estimate)
Flammpunkt
230 °F · >230 °F
storage temp.
Inert atmosphere,Room Temperature
pka
14.12 · 14.12±0.46(Predicted)
Aggregatzustand
Crystalline Powder or Flakes
Farbe
White to cream
Wasserlöslichkeit
soluble
Merck
14 · 14,2963
BRN
1928444 · 1928444
InChI
1S/C9H15NO2/c1-5-8(12)10-9(3,4)6-7(2)11/h5H,1,6H2,2-4H3,(H,10,12)
InChIKey
OMNKZBIFPJNNIO-UHFFFAOYSA-N
SMILES
CC(=O)CC(C)(C)NC(=O)C=C
LogP
0.321 at · 0.321 at 21℃
CAS Datenbank
2873 · 2873-97-4(CAS DataBase Reference)
NIST chemische Informationen
2 · 2-Propenamide, n-(1,1-dimethyl-3-oxobutyl)-(2873-97-4)
EPA chemische Informationen
N-(1,1-Dimethyl-3-oxobutyl)acrylamide (2873-97-4)
Reactivity Profile · 1 Eintrag

DIACETONE ACRYLAMIDE forms polymers in solution, in bulk, or in emulsion. May react vigorously with strong oxidizing agents. Can react exothermically with reducing agents (such as alkali metals and hydrides) to release gaseous hydrogen. May react exothermically with both acids and bases. May undergo autoxidation upon exposure to the air to form explosive peroxides.

Air and Water ReactionsWater soluble.
Toxic Combustion ProductsWhen heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Hazard Classes and Categories · 2 Einträge

Acute Tox. 4 (82%)

Acute toxicity (Oral) - Category 4

Sicherheit und Schutzausrüstung

Fire FightingA fire in your laboratory involving this chemical should be extinguished with a dry chemical, carbon dioxide or halon extinguisher. (NTP, 1992)
First Aid · 1 Eintrag

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.

Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a strong 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.

Disposal Methods · 1 Eintrag

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.

Personal Protective Equipment (PPE) · 1 Eintrag

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.

Toxikologische Informationen

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Non-Human Toxicity ExcerptsModerately toxic by ingestion.
Antidote and Emergency Treatment · 2 Einträge

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

Non-Human Toxicity Values · 2 Einträge

LD50 Rat oral 1770 mg/kg

LD50 Mouse oral 1303 mg/kg

Sicherheitsdaten

F
3
wgk
1
tsca
TSCA listed
hs_code
29241990
RTECS-Nr.
AS3475000
risk_code
22
Toxizität
LD50 orally in mice: 7.7 mmol/kg (Hashimoto)
hazard_code
Xn
safety_code
23-24/25
Speicherklasse
11 - Combustible Solids
Giftige Stoffe Daten
2873-97-4(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 4 Oral

Anwendungen

VerwendenDiacetone acrylamide is used in epoxy resin, acryl emulsion, water based paints, waste water treatment, photosensitive resins, waterborne coatings and gel electrophoresis. It is also used in the manufacture of permanent press fabrics.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Tetrachlormethan4-Hydroxy-4-methylpentan-2-onAcrylnitrilAcetonEssigsäureanhydrid