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Acrylsäure-2-cyanoethylester

2-Cyanoethyl acrylate

HCID 7825
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GrundinformationenNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
106-71-8
Standard-SMILES
C=CC(=O)OCCC#N
InChIKey
AEPWOCLBLLCOGZ-UHFFFAOYSA-N
Summenformel
C6H7NO2
Durchschnittliche Molmasse
125,13 g/mol
Monoisotopische Masse
125,04767846

Namen und Bezeichner

Bevorzugter Name
2-Cyanoethyl acrylate
IUPAC
2-cyanoethyl prop-2-enoate
Lokaler Name
Acrylsäure-2-cyanoethylester
Englischer Name
2-Cyanoethyl acrylate
Summenformel
C6H7NO2
Molmasse
125.13

Namen und Synonyme

2-CYANOETHYL ACRYLATE2-cyanoethyl prop-2-enoateCyanoethyl acrylate2-Cyanoethyl propenoatebeta-cyanoethyl acrylate2-Propenoic acid, 2-cyanoethyl esterAcrylic acid, 2-cyanoethyl esterHSDB 5372Hydracrylonitrile, acrylateAcrylic acid, ester with hydracrylonitrileEINECS 203-426-7NSC 18593
Weitere Namen anzeigen
2-cyanoethylcyanoethylacrylateB-CYANOETHYL ACRYLATE2-cyanoethylpropenoateacrylatede2-cyanoethylehydracrylonitrileacrylate2-CYANOETHYL-2-PROPENOATE3-ACRYLOYLOXYPROPIONITRILE
DTXSID1044776UNII-3ICU1C15OY3ICU1C15OYBRN 1756010AI3-028852-CYANOETHYL ACRYLATE [HSDB]NSC-18593DTXCID9024776

Datenbank-Bezeichner

CAS
106-71-8
PubChem CID
7825
DTXSID
DTXSID1044776

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,6
Polarare Oberfläche (TPSA)
50,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
4
Schwere Atome
9
Formalladung
0
Komplexität
154

Experimentelle und physikochemische Eigenschaften

PolymersPlastics & Rubber -> (Meth)acrylates
Density2.069
Color/FormLiquid
SolubilitySoluble in water
Flash Point · 2 Einträge

124 °C

255 °F (124 °C) (OPEN CUP)

DecompositionWhen heated to decomposition it emits toxic fumes of nitroxides and CN-.
Melting PointFreezing point: -16.9 °C
Vapor Density4.3 (AIR= 1)
Vapor Pressure0.22 [mmHg]
Physical DescriptionColorless liquid; [CHEMINFO]
Other Experimental Properties · 2 Einträge

Polymerizes when heated

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 · 4 Einträge

Danger

H301 (18.8%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, 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 16 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory InformationChemical: 2-Propenoic acid, 2-cyanoethyl ester
Fire PotentialA fire hazard when exposed to heat or flame.
Hazards Summary · 1 Eintrag

Irritating to skin and eyes; [SAX] External application to rabbit eyes scored 8 on a scale of 1-10 (10 being most severe) for degree of injury after 24 hours; [HSDB] A severe skin and eye irritant, based on animal studies; [CHEMINFO] May polymerize on light exposure; May decompose on exposure to moisture; A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis and pulmonary edema; A possible sensitizer; [MSDSonline] See ACRYLIC RESINS (MONOMERS).

NFPA Hazard Classification · 3 Einträge

2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.

1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.

1 - Materials that in themselves are normally stable but that can become unstable at elevated temperatures and pressures.

Chemie und Industrie

Verwendung und Herstellung

Uses · 3 Einträge

Used to form polymers and copolymers in adhesives and textile finishes and sizes; [HSDB]

Working with Glues and Adhesives [Category: Other]

Forms polymers and copolymers for viscosity index improvers; adhesives; textile finishes & sizes.

U.S. Imports(1983) 1.36x10+9 g /Acrylates & Acrylic Acid/
U.S. Production · 2 Einträge

(1977) AT LEAST 4.54X10+6 G

(1981) NO EVIDENCE OF COMMERCIAL PRODN IN U.S.

Methods of Manufacturing · 2 Einträge

Sodium cyanide + ethylene oxide + acrylic acid (epoxidation/esterification)

In ... propylene oxidation process acrolein is first formed by the catalytic oxidation of propylene vapor at high temp in the presence of steam. The acrolein is then oxidized to acrylic acid. ... The acrylic acid is esterified with alcohol to the ... acrylic ester in a separate process. /Acrylic ester monomers/

Formulations/Preparations... Hydroquinone or monomethyl ether hydroquinone are added to acrylic monomers to stabilize them .... /Acrylic ester monomers/
General Manufacturing Information2-Propenoic acid, 2-cyanoethyl ester: ACTIVE

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

3-Hydroxypropiononitrilacrylic acid methyl ester

Anbieter57 Anbieter

梯希爱(上海)化成工业发展有限公司

Zugehörige Reaktionen

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Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 64665
HRID 64665als Produktals Eduktuspto-grants-1986_09
Reaktionsgleichung von HRID 651954
HRID 651954als Produktals Eduktuspto-grants-1987_06
Reaktionsgleichung von HRID 1112075
HRID 1112075als Eduktuspto-grants-1978_10
Reaktionsgleichung von HRID 1112076
HRID 1112076als Eduktuspto-grants-1978_10
Reaktionsgleichung von HRID 1590762
HRID 1590762als Eduktuspto-grants-1993_04

Notizen zur Verbindung

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Auf dieser SeiteGrundinformationenNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
ChEMBL
CHEMBL3184893
UNII
3ICU1C15OY
EC Number
203-426-7
Nikkaji
J60.948J

React readily with electrophilic, free-radical, and nucleophilic agents /Acrylic acid & esters/

Physikochemische Eigenschaften

Schmelzpunkt
-16.8 °C · -16.8°C
Siedepunkt
90 °C · 90°C 5mm
Dichte
1.07 · 1.07
Brechungsindex
1.443 · 1.4430-1.4470
Flammpunkt
124 °C · 124 °C
storage temp.
2 · under inert gas (nitrogen or Argon) at 2-8°C
Wasserlöslichkeit
Soluble in water
Aggregatzustand
clear liquid
Farbe
Colorless to Almost colorless
CAS Datenbank
106 · 106-71-8(CAS DataBase Reference)
EPA chemische Informationen
2 · 2-Cyanoethyl acrylate (106-71-8)
Peroxide Forming Chemical · 4 Einträge

2-Cyanoethyl acrylate

C*: Compounds that autopolymerize due to peroxide formation if inhibitors are depleated or not present

PubChem

Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. 1(78) 349

Hazard Classes and CategoriesAcute Tox. 3 (18.8%)
Skin, Eye, and Respiratory Irritations · 2 Einträge

THE LOWER-MOL-WT ESTERS OF ACRYLIC ACIDS ARE IRRITANTS TO SKIN, EYES, & MUCOUS MEMBRANES. /ACRYLIC ACID ESTERS/

A skin and eye irritant.

Sicherheit und Schutzausrüstung

Fire Fighting ProceduresWater or foam may cause frothing ....
Storage Conditions · 1 Eintrag

The effectiveness of phenolic inhibitors is dependent on the presence of oxygen and the monomers must be stored under air rather than an inert atmosphere. Temp must be kept low to minimize formation of peroxides and other products. ... The acrylic esters may be stored in mild or stainless steel, or aluminum. /Acrylic acid & derivatives/

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.

Preventive Measures · 3 Einträge

Awareness of the dangers and of good engineering design are essential to safety. Employees should be instructed about the necessity of cleansing the skin if it is contaminated by materials which are irritants or skin-absorbed. With careful design, however, and complete enclosure of those processes where toxic chemicals or intermediates occur, dangerous exposures can be avoided. /Acrylic acid & derivatives/

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

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) · 2 Einträge

SUITABLE PROTECTIVE CLOTHING & SELF-CONTAINED RESP PROTECTIVE APPARATUS SHOULD BE AVAILABLE FOR USE OF THOSE WHO MAY HAVE TO RESCUE PERSONS OVERCOME BY FUMES. /ACRYLIC ACID & DERIVATIVES/

Protection required for safe handling of acrylic acid and esters commonly includes use of impervious gloves, shoe soles, and clothing; splash-proof goggles ... /Acrylic acid & derivatives/

Toxikologische Informationen

Adverse EffectsDermatotoxin - Skin burns.
Human Toxicity Excerpts · 2 Einträge

Three cases of contact dermatitis, due to exposure to ethyl cyanoacrylate (ECA) containing glue, in women aged 42, 23, and 48 years were described. The patients presented with complaints of a pruritic eczematous eruption on the hands. The lesions were concentrated primarily around the periungual folds and fingertips. In the 48 year old, patient the hand dermatitis was associated with chronic eyelid dermatitis. The 23 and 48 year old patients had been undergoing nail wrapping for about 6 months. The 42 year old patient was a manicurist who specialized in nail wrapping. Patch testing with the International Contact Dermatitis Research Group (ICDRG) standard battery and a resin of toluene-sulfonamide and formaldehyde was performed. All patients were negative to the resin and the 42 and 23 year old patients gave negative responses to the entire ICDRG battery. The 48 year old patient was negative to the ICDRG battery except for 0.5 percent diaminodiphenylmethane in petrolatum. The patients were patch tested with Krazy Glue, an acrylate based glue used in nail wrapping. All three gave moderate to strong positive responses. Their dermatitis cleared when they avoided contact with Krazy Glue. Analytical data supplied by the manufacturer showed that Krazy Glue contains 99.95 percent ECA and 0.05 percent undefined acrylic contaminants. The product had not induced any allergic reactions in animal studies. The author suggests that ECA is the allergen responsible for the patients' dermatitis, and that the localization of the rash to the hands suggests that the dermatitis originates from direct contact with ECA rather than from systemic absorption. He also suggests that dermatologists in areas where nail wrapping is popular should be on the alert for patients with possible cyanoacrylate allergies.

THE ACUTE TOXICITY OF THE ACRYLATES DECREASES WITH INCREASING MOLECULAR WEIGHT. ... HUMAN SIGNS & SYMPTOMS FOLLOWING INGESTION OF ACRYLIC MONOMERS INCL COLLAPSE, SEVERE RESPIRATORY DIFFICULTIES, & CNS STIMULATION. ACUTE INHALATION OF HIGHER CONCN MAY CAUSE MARKED IRRITATION, SALIVATION, CONJUNCTIVAL IRRITATION, & PRONOUNCED PULMONARY IRRITATION OR EDEMA. PROLONGED SKIN OR EYE CONTACT MAY RESULT IN SEVERE TISSUE DAMAGE. THE PATHOLOGY FROM SINGLE EXPOSURE IS CONTRARY TO REPEATED EXPOSURE EFFECTS, WHICH INCL PULMONARY CONGESTION OR HEMORRHAGE & CLOUDY SWELLING OF LIVER & KIDNEY. /ACRYLATES/

Non-Human Toxicity Excerpts · 2 Einträge

Acrylic acid 2-cyanoethyl ester has been tested externally on the eyes of rabbits & ... rated 8 on scale of 1 to 10 according to the degree of injury observed after 24 hr. The most severely injurious substances have been rated 10.

Contact sensitivity was produced in Guinea pigs with mono-, di-, and tri- acrylate compounds. /Mono-, di-, and tri- acrylate compounds/

Antidote and Emergency Treatment · 2 Einträge

Basic treatment: Establish a patent airway. Suction if necessary. Encourage patient to take deep breaths. Watch for signs of respiratory insufficiency and assist ventilations if necessary. 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 ... . /Irritating materials/

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. Early intubation at the first sign of upper airway obstruction may be necessary. Positive-pressure ventilation techniques with a bag-valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W TKO /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 ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Irritating materials/

Non-Human Toxicity Values · 2 Einträge

LD50 Rat oral 180 mg/kg

LD50 Rabbit skin 220 ul/kg

Sicherheitsdaten

tsca
TSCA listed
ridadr
3276
hs_code
2926907090
RTECS-Nr.
AT1500000
risk_code
20/21/22-36/37/38
safety_code
26-36/37/39
hazard_class
8
packing_group
II
Giftige Stoffe Daten
106-71-8(Hazardous Substances Data)
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