Isobutyl nitrite

HCID 10958

Basic information

CAS
542-56-3
Standard SMILES
CC(C)CON=O
InChIKey
APNSGVMLAYLYCT-UHFFFAOYSA-N
Molecular formula
C4H9NO2
Average molar mass
103.12 g/mol
Monoisotopic mass
103.06332853

Overview

Isobutyl Nitrite can cause cancer according to The National Toxicology Program.

Names & identifiers

Preferred name
Isobutyl nitrite
IUPAC
2-methylpropyl nitrite
English name
Isobutyl nitrite
Molecular formula
C4H9NO2
Molecular weight
103.12

Names & synonyms

ISOBUTYL NITRITE542-56-3Nitrous acid, 2-methylpropyl esterNitrous acid, isobutyl esterDTXSID3020750NCI-C61052GW9WAB6QOMDTXCID70750CHEBI:46643RefChem:7916382-methylpropyl nitrite;isobutyl nitrite208-819-7
Show more names
isobutyl nitrilei-Butyl nitriteIsobutylnitrite, stabilized with anhydrous 0.5% sodium carbonateIsobutylnitrite,94%,stabilized with anhydrous0.5% sodium carbonateIsobutylnitrite, 94%, stabilized with 0.5%anhydrous sodium carbonate
Isobutylnitrite2-methylpropyl nitritenitrous acid 2-methylpropyl esterIsobutylnitritIBNMFCD00002056(CH3)2CHCH2ONOBlackjack

Database identifiers

CAS
542-56-3
PubChem CID
10958
DTXSID
DTXSID3020750
ChEMBL
CHEMBL1526886
ChEBI
CHEBI:46643
UNII
GW9WAB6QOM
EC Number
208-819-7
Nikkaji
J4.509H

Properties

Computed structural properties

XLogP
1.4
Topological polar surface area
38.7 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
2
Heavy atoms
7

Experimental & physicochemical properties

Chemical Classes · 2 items

Nitrogen Compounds -> Nitrates and Nitrites

Flammable agents - 3rd degree

SpringerMaterials PropertiesCoriolis coupling
Density · 4 items

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

Color/FormCOLORLESS LIQUID
Solubility · 3 items

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 · 4 items

-10 °F (NTP, 1992)

-10 °F

-21 °C

-10 °F

Physicochemical properties

Boiling point
66 · 66-67 °C(lit.)
Density
0.87 g/mL · 0.87 g/mL at 25 °C(lit.)
refractive index
20 · n20/D 1.373(lit.)
Flash point
6 °F · −6 °F
storage temp.
0 · 0-6°C
form
clear liquid

Safety & regulation

GHS classification

GHS Classification · 6 items

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)

Hazard information

Regulatory Information · 2 items

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.)

DOT LabelFlammable Liquid Poison
Fire Hazards · 2 items

This chemical is flammable. (NTP, 1992)

Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive.

Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include headache, dizziness and tachycardia. Other symptoms include carboxyhemoglobinemia, fall in blood pressure and change in heart rate.
Hazards Summary · 1 item

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]

Reactive GroupNitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

Safety & protection

Fire Fighting · 2 items

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 · 4 items

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 · 1 item

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.

Safe StorageFireproof. Separated from acids. Well closed.
Exposure Control and Personal ProtectionBiological Exposure Indices (BEI) [ACGIH] - Methemoglobin in blood = 1.5% of hemoglobin during or at end of shift. [ACGIH]
Nonfire Spill Response · 1 item

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.

Toxicology

InteractionsPRETREATMENT WITH A SINGLE DOSE OF METHYLENE BLUE PREVENTS THE METHEMOGLOBIN FORMATION AND PROTECTS AGAINST THE LETHALITY OF THE BUTYL NITRITES IN MICE.
Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure RoutesThe substance can be absorbed into the body by inhalation and by ingestion.
Signs and Symptoms · 2 items

Sore throat. Headache. Dizziness. Blue lips, fingernails and skin. Nausea. Confusion. Convulsions. Unconsciousness. Symptoms may be delayed.

See Inhalation.

Ongoing Test Status · 1 item

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 · 4 items

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.

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
rtecs
RA0805000
ridadr
UN 2351 3/PG 2
hs_code
29209090

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationDrugs used to cause dilation of the blood vessels.

Uses & manufacturing

Uses · 2 items

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/

Methods of ManufacturingFROM ISOBUTYL ALCOHOL, SODIUM NITRITE, AND DILUTE SULFURIC ACID.
General Manufacturing InformationNitrous acid, 2-methylpropyl ester: ACTIVE
Applications · 2 items

UsesIsobutyl 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.

General DescriptionIsobutyl nitrite is an ester of isobutanol and nitrous acid, which has a various range of household and industrial applications. It is commonly added to a number of household cleaning liquids and air fresheners. As a volatile liquid, it also serves as a "room odorizer" which is widely sold without a prescription.Besides, Isobutyl nitrite has also been applied in pharmaceuticals, in which it acts as a vasodilator (blood vessel relaxant) and is used medically as part of the emergency antidote for cyanide poisoning.

Preparation methods

PreparationIsobutyl nitrite is synthesized by reacting isobutyl alcohol with sodium nitrite in dilute sulfuric acid (NTP, 1996).

Upstream & downstream products

Suppliers100 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
山东旭晨化工科技有限公司0533-15715337262 15715337262 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
广州纳珑化工有限公司13192879270; 13192879270 · [email protected]
温州共赢化学有限公司+86-0086-577-64498589 +86-15355981851 · [email protected]

Additional notes

DefinitionChEBI: Isobutyl nitrite is a member of nitrite esters. It derives from an isobutanol.

Related reactions

38 records

Compound notes

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