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Isobutyl nitrite

Isobutyl nitrite structure

Isobutyl nitrite 

structure
  • CAS No:

    542-56-3

  • Formula:

    C4H9NO2

  • Chemical Name:

    Isobutyl nitrite

  • Synonyms:

    Nitrous acid,2-methylpropyl ester;Nitrous acid,isobutyl ester;Isobutyl nitrite;iso-Butyl nitrite;Blackjack;2-Methylpropyl nitrite

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

colourless to pale yellow liquid


Isobutyl nitrite is a clear colorless to pale yellow liquid. Boiling point 154.4°F (68°C).|COLOURLESS LIQUID.|Clear colorless to pale yellow liquid.


Isobutyl nitrite is a clear colorless to pale yellow liquid. Boiling point 154.4°F (68°C).|Isobutyl nitrite is a member of nitrite esters. It derives from an isobutanol.

Isobutyl nitrite Basic Attributes

103.12

103.12

1699518

208-819-7

GW9WAB6QOM

1651

1992|2351

DTXSID3020750

COLORLESS LIQUID

29209090

Characteristics

38.7

1.92

Isobutyl nitrite is a clear colorless to pale yellow liquid. Boiling point 154.4°F (68°C).

0.870 g/cm3 @ Temp: 22 °C

67 °C

−6 °F

1.416

H2O: <0.1 g/100 mL (19 ºC)

0-6°C

Vapour pressure, kPa at 20°C: 1.3

>1

Oral-Rat LD50: 410 mg/kg; Oral-Mouse LD50: 205 mg/kg

It is flammable in case of open flame, high temperature and oxidant; it produces toxic nitrogen oxide fumes during combustion; it produces toxic nitrogen oxide gas when exposed to light

vol% in air: 1.26.9

UV: 3-22 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York) /Sec-butyl nitrite/

Highly flammable. Insoluble in water. Slowly decomposes in water.

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

Highly Flammable

An oxidizing agent but can serve as a reducing agent. May begin a vigorous reaction that culminates in a detonation if mixed with reducing agents, including hydrides, sulfides, nitrides, ammonium salts, cyanides, and many fuels.

The vapour is heavier than air and may travel along the ground; distant ignition possible.

Safety Information

II

3

UN 2351 3/PG 2

3

45-11-20/22-68

53-45

RA0805000

F,T,Xi

The warehouse is ventilated, low temperature and dry; stored separately from oxidants and acids

Irritant/Highly Flammable/Keep Cold/Air Sensitive/Light Sensitive

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.

P201-P210-P281-P308 + P313

H225-H302-H332-H341-H350

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

This chemical is flammable. (NTP, 1992)|Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive.|Flammable - 3rd degree, Reactive - 4th degree

|Danger|H225: Highly Flammable liquid and vapor [Danger Flammable liquids]|P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P281, P301+P312, P303+P361+P353, P304+P312, P304+P340, P308+P313, P312, P330, P370+P378, P403+P235, P405, and P501|H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]|Aggregated GHS information provided by 46 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P281, P301+P312, P303+P361+P353, P304+P340, P307+P311, P308+P313, P311, P314, P321, P330, P370+P378, P403+P233, P403+P235, P405, and P501|P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P281, P301+P312, P303+P361+P353, P304+P340, P307+P311, P308+P313, P309+P311, P311, P314, P321, P330, P370+P378, P403+P233, P403+P235, P405, and P501

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.

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

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. STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store it in an explosion-proof refrigerator. STORE AWAY FROM SOURCES OF IGNITION. (NTP, 1992)

RECOMMENDED RESPIRATOR: When working with this chemical, wear a NIOSH-approved full face chemical cartridge respirator equipped with the appropriate organic vapor cartridges. If that is not available, a half face respirator similarly equipped plus airtight goggles can be substituted. However, please note that half face respirators provide a substantially lower level of protection than do full face respirators. RECOMMENDED GLOVE MATERIALS: If this chemical makes direct contact with your gloves, or if a tear, puncture or hole develops, replace them at once. Glove Type Model Number Thickness Bkthru Time Viton North F-091 0.41 mm 18 min Butyl Rubber North B-174 0.69 mm 75 min Nitrile Edmont 37-155 0.61 mm 91 min PVA Edmont 29-250 0.53 mm 19 min PVC Edmont 34-100 0.15 mm 2 min (NTP, 1992)

Explosive limits , vol% in air: 1.2-26.9

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.

Fireproof. Separated from acids. Well closed.

A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.

The substance may cause effects on the blood and cardiovascular system. This may result in cardiac disorders and the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated. Exposure at high levels could cause death.

This substance is possibly carcinogenic to humans.

NO open flames, NO sparks and NO smoking. Closed system, ventilation, explosion-proof electrical equipment and lighting. Do NOT use compressed air for filling, discharging, or handling.

AVOID ALL CONTACT!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety spectacles.

Toxicity

highly toxic

PRETREATMENT WITH A SINGLE DOSE OF METHYLENE BLUE PREVENTS THE METHEMOGLOBIN FORMATION AND PROTECTS AGAINST THE LETHALITY OF THE BUTYL NITRITES IN MICE.

... 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.

Drug Information

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

SYMPTOMS: 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. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of nitrogen oxides. (NTP, 1992)

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 area; take 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 used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Volatile chemicals have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. 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. IMMEDIATELY transport the victim to a hospital. 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)


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).

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.

isobutyl nitrite

The substance can be absorbed into the body by inhalation and by ingestion.

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

Isobutyl nitrite Use and Manufacturing

Methods of Manufacturing

FROM ISOBUTYL ALCOHOL, SODIUM NITRITE, AND DILUTE SULFURIC ACID.

Uses

USED TO A LIMITED EXTENT IN INDUSTRY AS INTERMEDIATES IN CHEMICAL SYNTHESES /ALIPHATIC NITRITES/

Nitrous acid, 2-methylpropyl ester: ACTIVE

COMMERCIALLY AVAILABLE ISOBUTYL NITRITE WAS DETERMINED TO BE 63% PURE BY GAS-LIQUID CHROMATOGRAPHIC ANALYSIS.

Fire Hazards -> Flammable - 3rd degree, Reactive - 4th degree

Computed Properties

Molecular Weight:103.12
XLogP3:1.4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:103.063328530
Monoisotopic Mass:103.063328530
Topological Polar Surface Area:38.7
Heavy Atom Count:7
Complexity:53.7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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