Grundinformationen
- CAS
542-56-3- Standard-SMILES
CC(C)CON=O- InChIKey
APNSGVMLAYLYCT-UHFFFAOYSA-N- Summenformel
- C4H9NO2
- Durchschnittliche Molmasse
- 103,12 g/mol
- Monoisotopische Masse
- 103,06332853
Überblick
Isobutyl Nitrite can cause cancer according to The National Toxicology Program.
Namen und Bezeichner
- Bevorzugter Name
- Isobutyl nitrite
- IUPAC
- 2-methylpropyl nitrite
- Lokaler Name
- Isobutylnitrit
- Englischer Name
- Isobutyl nitrite
- Summenformel
- C4H9NO2
- Molmasse
- 103.12
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
542-56-3- PubChem CID
- 10958
- DTXSID
DTXSID3020750- ChEMBL
CHEMBL1526886- ChEBI
CHEBI:46643- UNII
- GW9WAB6QOM
- EC Number
- 208-819-7
- Nikkaji
- J4.509H
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,4
- Polarare Oberfläche (TPSA)
- 38,7 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 7
- Formalladung
- 0
- Komplexität
- 53,7
Experimentelle und physikochemische Eigenschaften
Chemical Classes
Nitrogen Compounds -> Nitrates and Nitrites
Flammable agents - 3rd degree
Density
0.87 at 72 °F (NTP, 1992) - Less dense than water; will float
0.870 AT 22 °C/4 °C
Relative density (water = 1): 0.87
0.87 at 72 °F
Solubility
less than 1 mg/mL at 66 °F (NTP, 1992)
SLIGHTLY SOLUBLE AND GRADUALLY DECOMPOSED BY WATER; MISCIBLE WITH ALCOHOL
Solubility in water: very poor
Flash Point
-10 °F (NTP, 1992)
-10 °F
-21 °C
-10 °F
Boiling Point
153 °F at 760 mmHg (NTP, 1992)
67 °C
67 °C
154.4 °F
Vapor Density
greater than 1 (NTP, 1992) (Relative to Air)
Relative vapor density (air = 1): 3.56
>1
Vapor Pressure
10 mmHg at 68 °F ; 17.80 mmHg at 86 °F (NTP, 1992)
10.0 [mmHg]
Vapor pressure, kPa at 20 °C: 1.3
10 mmHg
Physical Description
Isobutyl nitrite is a clear colorless to pale yellow liquid. Boiling point 154.4 °F (68 °C).
Clear colorless to pale yellow liquid; [CAMEO]
COLOURLESS LIQUID.
Clear colorless to pale yellow liquid.
Physikochemische Eigenschaften
- Siedepunkt
- 66 · 66-67 °C(lit.)
- Dichte
- 0.87 g/mL · 0.87 g/mL at 25 °C(lit.)
- Brechungsindex
- 20 · n20/D 1.373(lit.)
- Flammpunkt
- 6 °F · −6 °F
- storage temp.
- 0 · 0-6°C
- Aggregatzustand
- clear liquid
- Farbe
- Light yellow to Yellow to Orange
- Wasserlöslichkeit
- 0.1 g/100 · <0.1 g/100 mL (19 ºC)
- Merck
- 14 · 14,5149
- BRN
- 1699518 · 1699518
- Stabilität
- Stable. Incompatible with acids, alcohols, strong bases. Decomposes slowly in water. Flammable - incompatible with strong oxidizing agents. Note wide explosion limits. May be light and moisture sensitive. Oxidizer. May explode if heated.
- InChI
- 1S/C4H9NO2/c1-4(2)3-7-5-6/h4H,3H2,1-2H3
- InChIKey
- APNSGVMLAYLYCT-UHFFFAOYSA-N
- SMILES
- CC(C)CON=O
- CAS Datenbank
- 542 · 542-56-3(CAS DataBase Reference)
- NIST chemische Informationen
- (CH3)2CHCH2ONO(542-56-3)
- EPA chemische Informationen
- Isobutyl nitrite (542-56-3)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H225: Highly Flammable liquid and vapor [Danger Flammable liquids]
P203, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P317, P303+P361+P353, P304+P340, P317, P318, P330, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)
Danger
H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P203, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P317, P303+P361+P353, P304+P340, P317, P318, P330, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)
Gefahrenhinweise
Regulatory Information
Hazard Traits - Carcinogenicity
The 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.)
Fire Hazards
This chemical is flammable. (NTP, 1992)
Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive.
Hazards Summary
High doses cause death from methemoglobinemia in acute and subchronic animal studies. Delayed animal deaths were attributeed to hepatotoxicity; [ACGIH] Liver damage as a cause of death was suggested in one animal study. [HSDB] A volatile substance that may be abused by inhalation mainly for its vasodilator properties; [Reference #1]
Special Reports
Toxicology & Carcinogenesis Studies of Isobutyl Nitrite in F344/N Rats and B6C3F1 Mice (Inhalation Studies). Technical Report Series No. 448 (1996) NIH Publication No. 96-3364 U.S. Department of Health and Human Services, National Toxicology Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709
Sicherheit und Schutzausrüstung
Fire Fighting
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
Use dry powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures
Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.
Rinse and then wash skin with water and soap.
Rinse with plenty of water for several minutes (remove contact lenses if easily possible).
Rinse mouth. Give a slurry of activated charcoal in water to drink. Refer for medical attention .
First Aid
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
SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed 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.
Spillage Disposal
Personal protection: self-contained breathing apparatus. Evacuate danger area! Consult an expert! Ventilation. Remove all ignition sources. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer.
Toxikologische Informationen
Signs and Symptoms
Sore throat. Headache. Dizziness. Blue lips, fingernails and skin. Nausea. Confusion. Convulsions. Unconsciousness. Symptoms may be delayed.
See Inhalation.
Ongoing Test Status
The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=542-56-3]
Human Toxicity Excerpts
THOUGH THE USUAL ROUTE OF ADMINISTRATION BY INHALATION HAS NOT RESULTED IN ANY TOXICOLOGICALLY VERIFIED DEATHS, ISOBUTYL NITRITE MAY CAUSE FATAL TOXIC METHEMOGLOBINEMIA IF INGESTED. A CASE WITH A FATAL OUTCOME IS PRESENTED.
METHEMOGLOBINEMIA OCCURRED IN A 36-YR-OLD MAN WHO INGESTED 15 ML OF ISOBUTYL NITRITE (RUSH). HE RECOVERED AFTER TREATMENT WITH INTRAVENOUS 1% METHYLENE BLUE, 20 ML, INFUSED OVER 20 MINUTES.
A CASE REPORT OF SEVERE AND PROLONGED TRACHEOBRONCHITIS IN A 23-YR-OLD MALE, FOLLOWING THE INHALATION OF 2 BOTTLES OF LOCKER ROOM (ISOBUTYL NITRITE), IS PRESENTED.
AT A 1% ADDED CONCN, ISOBUTYL NITRITE LYSED HUMAN LEUKOCYTES AND REDUCED VIABILITY FROM 95 TO 21% IN 24 HR. AT LESS THAN OR EQUAL TO 0.5%, CELL COUNT AND VIABILITY WERE UNAFFECTED, BUT ISOBUTYL NITRITE INHIBITED IN VITRO LYMPHOCYTE BLASTOGENIC RESPONSES TO PHYTOHEMAGGLUTININ, POKEWEED MITOGEN, AND CONCANAVALIN A. IT INHIBITED NATURAL KILLER CELL ACTIVITY TO THE K562 CELL LINE, LYMPHOCYTE-MEDIATED ANTIBODY-DEPENDENT CELLULAR CYTOTOXICITY TO THE CEM CELL LINE, MONOCYTE-MEDIATED ANTIBODY-DEPENDENT CELLULAR CYTOTOXICITY TO HUMAN RED BLOOD CELLS, AND IN VITRO ADHERENCE AND TRANSFORMATION OF MONOCYTES TO MACROPHAGES. INHIBITORY EFFECTS WERE GREATER THAN 90% AT 0.5% AND STILL DETECTABLE AT 0.01%. ISOBUTYL NITRITE INHIBITED LEUCINE, URIDINE, AND THYMIDINE INCORPORATION APPROX EQUALLY. AFTER 24 HR OF EXPOSURE, THE EFFECTS ON VARIOUS LYMPHOCYTE FUNCTION PARAMETERS WERE NOT REVERSIBLE.
Carcinogen Classification
Isobutyl nitrite
Group 2B: Possibly carcinogenic to humans
Volume 122: (2019) Isobutyl Nitrite, β-Picoline, and Some Acrylates
2019
2018
Isobutyl Nitrite
Non-Human Toxicity Excerpts
IN DETERMINING LD50 VALUES (MICE, INTRAPERITONEAL) FOR EACH COMPOUND, NO DEATHS WERE OBSERVED AFTER 30 MINUTES POSTADMINISTRATION FOR ISOBUTYL NITRITE. GROSS POSTMORTEM EXAMINATION SUGGESTED THE DELAYED LETHALITY MAY BE DUE TO LIVER DAMAGE.
WHEN MICE WERE EXPOSED TO BUTYL NITRITES IN AN INHALATION CHAMBER, A SIGNIFICANT LEVEL OF METHEMOGLOBINEMIA IS PRODUCED. THE POTENCY ORDER FOR METHEMOGLOBIN PRODUCTION OF THE 4 BUTYL NITRITES N-BUTYL NITRITE, ISO-BUTYL NITRITE, SEC-BUTYL NITRITE, AND TERT-BUTYL NITRITE IS THE SAME AS THAT OF THEIR LC50 VALUES AND PARALLELS THE ABILITY OF THE AGENTS TO CAUSE METHEMOGLOBIN FORMATION IN MOUSE ERYTHROCYTES IN VITRO.
ORAL ADMIN OF SINGLE DOSES OF BUTYL NITRITES TO MICE YIELDED LD50 VALUES FROM 171 TO 428 MG/KG. THE LETHAL TOXICITY OF SINGLE DOSES OF ISOBUTYL NITRITE, THE ISOMER COMMONLY USED AS A RECREATIONAL DRUG, COULD BE REDUCED BY PRETREATMENT WITH METHYLENE BLUE OR TOLUIDINE BLUE.
WHEN TESTED BY THE AMES MUTAGENICITY TEST ON SALMONELLA, ISOBUTYL NITRITE WAS MUTAGENIC WITH OR WITHOUT METABOLIC ACTIVATION. THE POTENTIAL CARCINOGENIC RISK OF SOME ALIPHATIC NITRITES, WHICH ARE BEING USED AS STREET DRUGS, IS DISCUSSED.
For more Non-Human Toxicity Excerpts (Complete) data for ISOBUTYL NITRITE (8 total), please visit the HSDB record page.
National Toxicology Program Studies
... Male and female F344/N rats and B6C3F1 mice were exposed to isobutyl nitrite (purity of 93% or greater) by inhalation for ... 2 years. ... 2-YEAR STUDY IN RATS: ... Isobutyl nitrite exposure concentrations selected for the 2 yr inhalation study in rats were 37.5, 75, and 150 ppm. Groups of 56 male and 56 female rats were exposed to 0, 37.5, 75, or 150 ppm (equivalent to 0, 158, 315, or 630 mg/cu m) isobutyl nitrite by inhalation for 6 hr/ day, 5 days/wk, for 103 wk. ... 2 YEAR STUDY IN MICE: ... Isobutyl nitrite exposure concentrations selected for the 2 yr inhalation study in mice were 37.5, 75, and 150 ppm. Groups of 60 male and 60 female mice were exposed to 0, 37.5, 75, or 150 ppm (equivalent to 0, 158. 315, or 630 mg/cu m) isobutyl nitrite by inhalation for 6 hr/day, 5 days/wk, for 103 wk. ... CONCLUSIONS: Under the conditions of these 2 year inhalation studies, there was clear evidence of carcinogenic activity of isobutyl nitrite in male and female F344/N rats based on the increased incidences of alveolar/bronchiolar adenoma and alveolar/bronchiolar adenoma or carcinoma (combined). There was some evidence of carcinogenic activity of isobutyl nitrite in male and female B6C3F1 mice based on the increased incidences of alveolar/bronchiolar adenoma and alveolar/bronchiolar adenoma or carcinoma (combined) in males andfemales. The increased incidence of thyroid gland follicular cell adenoma in male mice may have been related to isobutyl nitrite exposure.
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 2351 3/PG 2
- hs_code
- 29209090
- RTECS-Nr.
- RA0805000
- risk_code
- 45-11-20/22-68
- hazard_code
- F,T,Xi
- hazard_note
- Irritant/Highly Flammable/Keep Cold/Air Sensitive/Light Sensitive
- safety_code
- 53-45
- hazard_class
- 3
- packing_group
- II
- Speicherklasse
- 3 - Flammable liquids
- Giftige Stoffe Daten
- 542-56-3(Hazardous Substances Data)
- Hazard Classifications
- Acute Tox. 4 InhalationAcute Tox. 4 OralCarc. 1BFlam. Liq. 2Muta. 2
Chemie und Industrie
Pharmakologische Informationen
Verwendung und Herstellung
Uses
Used as a chemical intermediate and a drug for angina pectoris; [ACGIH] Amyl nitrite and isobutyl nitrite are used as illicit, aphrodisiac inhalants to enhance erection. [AHLS, p. 199]
USED TO A LIMITED EXTENT IN INDUSTRY AS INTERMEDIATES IN CHEMICAL SYNTHESES /ALIPHATIC NITRITES/
Anwendungen
VerwendenIsobutyl nitrite is an alkyl nitrite. It is mainly used in “poppers”, consumed as a recreational drug for their psychoactive effects. Poppers are illegal in many countries, and as a result are commonly sold as air fresheners or deodorizers. Other minor uses of isobutyl nitrite include as an intermediate in the synthesis of aliphatic nitrites, nail polish removers, video head cleaners, fuels, and jet propellants.Isobutyl nitrite was used to study inhalant-induced immunotoxicity. It is used in the preparation of plasmoquin.
Darstellung
synthetischeIsobutyl nitrite is synthesized by reacting isobutyl alcohol with sodium nitrite in dilute sulfuric acid (NTP, 1996).
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