542-56-3

Basic information

• Product Name: Isobutylnitrite
• Synonyms: ISOBUTYL NITRITE;2-METHYLPROPYL NITRITE;Nitrous acid，2-Methylpropyl ester;blackjack;IBN;NCI-C61052;Nitrous acid, isobutyl ester;nitrousacid,isobutylester
• CAS NO: 542-56-3
• Molecular Formula: C₄H₉NO₂
• Molecular Weight: 103.12
• EINECS: 208-819-7
• Product Categories: Nitrogen Compounds;Organic Building Blocks;Organic Nitrates/Nitrites;Organic Nitrates/Nitrites;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 542-56-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 66-67 °C(lit.)
• Flash Point: −6 °F
• Appearance: colourless to pale yellow liquid
• Density: 0.87 g/mL at 25 °C(lit.)
• Vapor Pressure: 140mmHg at 25°C
• Refractive Index: n20/D 1.373(lit.)
• Storage Temp.: 0-6°C
• Water Solubility: <0.1 g/100 mL (19℃)
• Sensitive: Light Sensitive/Air Sensitive
• Stability: Stable. Incompatible with acids, alcohols, strong bases. Decomposes slowly in water. Flammable - incompatible with strong oxidiz
• Merck: 14,5149
• BRN: 1699518
• CAS DataBase Reference: Isobutylnitrite(CAS DataBase Reference)
• NIST Chemistry Reference: Isobutylnitrite(542-56-3)
• EPA Substance Registry System: Isobutylnitrite(542-56-3)

Safety Data

• Hazard Codes: F,T,Xi
• Statements: 45-11-20/22-68
• Safety Statements: 53-45
• RIDADR: UN 2351 3/PG 2
• WGK Germany: 3
• RTECS: RA0805000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 542-56-3(Hazardous Substances Data)

Usage

Chemical Properties

Isobutyl nitrite is a colourless to pale yellow liquid and has a pleasant and fruity odor.

Uses

Isobutyl 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.

Definition

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

Preparation

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

General Description

Isobutyl 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.

Air & Water Reactions

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

Reactivity Profile

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.

Fire Hazard

Isobutylnitrite is flammable.

References

https://en.wikipedia.org/wiki/Isobutyl_nitritehttps://www.ncbi.nlm.nih.gov/pubmed/3698454http://amylnitrite.org/isobutyl

InChI:InChI=1/C4H9NO2/c1-4(2)3-7-5-6/h4H,3H2,1-2H3

Synthetic route

2-methyl-propan-1-ol (78-83-1) → nitrous acid isobutyl ester (542-56-3)

Conditions	Yield
With sodium nitrite in saurer Loesung;
With Nitrogen dioxide
With nitrosylchloride

Isobutyl bromide (78-77-3) → nitrous acid isobutyl ester (542-56-3) + 1-nitroisobutane (625-74-1)

Conditions	Yield
With silver(I) nitrite unter Kuehlung;

Isobutyl iodide (513-38-2) → nitrous acid isobutyl ester (542-56-3) + 1-nitroisobutane (625-74-1)

Conditions	Yield
With silver(I) nitrite unter Kuehlung;
With silver(I) nitrite; Petroleum ether

isobutyloxyl (26397-34-2) → nitrous acid isobutyl ester (542-56-3) + isobutyraldehyde (78-84-2)

Conditions	Yield
With H2(15)NO at 175℃; Product distribution; ratios of disproportion to combination reactions; labeled by 15N;

potassium isobutyl sulfate → nitrous acid isobutyl ester (542-56-3)

Conditions	Yield
With alkali nitrite beim schmelzen;
With alkaline earth nitrite Man schmilzt zusammen;

Isobutyl bromide (78-77-3) + silver nitrite → nitrous acid isobutyl ester (542-56-3) + 1-nitroisobutane (625-74-1)

Isobutyl iodide (513-38-2) + silver nitrite → nitrous acid isobutyl ester (542-56-3) + 1-nitroisobutane (625-74-1)

2-methyl-propan-1-ol (78-83-1) + cis-nitrous acid (7782-77-6) → nitrous acid isobutyl ester (542-56-3)

2-Methyl-4,5-dihydrofuran (1487-15-6) → nitrous acid isobutyl ester (542-56-3)

Conditions	Yield
With pyridine; hydrogenchloride; water In methanol at 65℃; for 1h; Solvent; Temperature; Reagent/catalyst;

nitrous acid isobutyl ester (542-56-3) → isobutyraldehyde (78-84-2)

Conditions	Yield
With dimethyl sulfoxide at 70℃; for 6h;	95.95%
With boron trifluoride diethyl etherate In diethyl ether for 4h; Ambient temperature;	92%

nitrous acid isobutyl ester (542-56-3) + 2-bromo-p-toluidine (583-68-6) → 3-bromo-4-fluorotoluene (452-62-0)

Conditions	Yield
With hydrogen fluoride; boron trifluoride In 1,2-dimethoxyethane	92.4%

nitrous acid isobutyl ester (542-56-3) + 2-bromo-p-toluidine (583-68-6) → 2-bromo-4-methylbenzenediazonium tetrafluoborate + 3-bromo-4-fluorotoluene (452-62-0)

Conditions	Yield
With hydrogen fluoride; boron trifluoride In 2-methyl-propan-1-ol	A n/a B 92.4%

3-isopentyl-3-(isobutyl α-D-glucopyranose-3-yl)-1-(2-chloroethyl)urea + nitrous acid isobutyl ester (542-56-3) → 3-n-propyl-3-(isobutyl α-D-glucopyranose-6-yl)-1-(2-chloroethyl)-1-nitrosourea + 3-isopentyl-3-(isobutyl α-D-glucopyranose-3-yl)-1-(2-chloroethyl)-1-nitrosourea

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; ethanol	A 67.3% B n/a

nitrous acid isobutyl ester (542-56-3) + 1-(9,9-dipropyl-9H-fluorene-2-yl)-4-cyclopentyl-1-butanone → 1-(9,9-dipropyl-9H-fluorene-2-yl)-4-cyclopentyl-1,2-butanedione-2-oxime

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 10℃; for 6h;	61.7%

nitrous acid isobutyl ester (542-56-3) + 1-(9,9-dipropyl-9H-fluorene-2yl)-3-cyclopentyl-1-propanone → 1-(9,9-dipropyl-9H-fluorene-2yl)-3-cyclopentyl-1,2-propanedione-2-oxime

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 5℃; for 6h;	60.1%

nitrous acid isobutyl ester (542-56-3) + 1-(9,9-dipropyl-9H-fluorene-2yl)-1-nonanone → 1-(9,9-dipropyl-9H-fluorene-2yl)-1,2-nonanedione-2-oxime

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 10℃; for 6h;	56.1%

nitrous acid isobutyl ester (542-56-3) + 1-(9,9-dipropyl-9H-fluorene-2yl)-1-octanone → 1-(9,9-dipropyl-9H-fluoren-2-yl)-1,2-octanedione-2-oxime

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 10℃; for 6h;	55.8%

nitrous acid isobutyl ester (542-56-3) + 1-(9H-fluoren-2-yl)-3-cyclopentyl-1-propanone → 1-(9H-fluoren-2-yl)-3-cyclopentyl-1,2-propanedione-2-oxime

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 5℃; for 6h;	53%

nitrous acid isobutyl ester (542-56-3) + 1-(9,9-dimethyl-9H-fluorene-2yl)-3-cyclopentyl-1-propanone → 1-(9,9-dimethyl-9H-fluorene-2yl)-3-cyclopentyl-1,2-propanedione-2-oxime

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 5℃; for 6h;	50.8%

nitrous acid isobutyl ester (542-56-3) + Triphenylmethylamin (5824-40-8) + sodium sulfate (7757-82-6) + (6R)-3-methyl-8-oxo-7c-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (27250-44-8) → Triphenylmethyl 3-methyl-7β-phenoxyacetamidoceph-3-em-4-carboxylate

Conditions	Yield
In dichloromethane; water; toluene	50%

cephalothin + nitrous acid isobutyl ester (542-56-3) + cyclohexylamine (108-91-8) → Cyclohexyl 3-acetoxymethyl-7β-(2-thienylacetamido)ceph-3-em-4-carboxylate

Conditions	Yield
In ISOPROPYLAMIDE; ethyl acetate; acetonitrile	22.9%

nitrous acid isobutyl ester (542-56-3) + ethyl 7-(2-amino-4-(tert-butoxycarbonyl)phenoxy)-8-bromo-6-chlorochroman-4-carboxylate (1202890-01-4) → ethyl 8-bromo-7-(4-(tert-butoxycarbonyl)phenoxy)-6-chlorochroman-4-carboxylate (1202890-02-5)

Conditions	Yield
In N,N-dimethyl-formamide at 70℃; for 0.5h;	17%

2,3-dihydro-1H-benzindene-1-one (6342-87-6) + nitrous acid isobutyl ester (542-56-3) → 3H-cyclopenta[a]naphthalene-1,2-dione-2-oxime (109725-95-3)

nitrous acid isobutyl ester (542-56-3) + 3-chloropropiophenone (936-59-4) → 3-chloro-1-phenyl-propane-1,2-dione-2-oxime (61655-94-5)

Conditions	Yield
With hydrogenchloride; ether benzene

nitrous acid isobutyl ester (542-56-3) + 3-methoxy-1-phenylpropan-1-one (55563-72-9) → 3-chloro-1-phenyl-propane-1,2-dione-2-oxime (61655-94-5)

Conditions	Yield
With hydrogenchloride; ether benzene

nitrous acid isobutyl ester (542-56-3) + 3-methoxy-1-phenylpropan-1-one (55563-72-9) → 3-methoxy-1-phenyl-propane-1,2-dione-2-oxime

Conditions	Yield
With hydrogenchloride

nitrous acid isobutyl ester (542-56-3) + 3-methoxy-1-phenylpropan-1-one (55563-72-9) → 3-methoxy-1-phenyl-propane-1,2-dione-2-[O-(4-nitro-benzoyl)-oxime ]

Conditions	Yield
anschliessendes Behandeln mit 4-Nitro-benzoylchlorid;

nitrous acid isobutyl ester (542-56-3) + ethyl 3,4-dimethoxyphenyl ketone (1835-04-7) → 1-(3,4-dimethoxy-phenyl)-propane-1,2-dione-2-oxime (103502-07-4)

Conditions	Yield
With hydrogenchloride; benzene

nitrous acid isobutyl ester (542-56-3) + 1-(4-hydroxy-3-methylphenyl)propan-1-one (940-04-5) → 1-(4-hydroxy-3-methyl-phenyl)-propane-1,2-dione-2-oxime

Conditions	Yield
With hydrogenchloride; diethyl ether; benzene

nitrous acid isobutyl ester (542-56-3) + 3,4-diethoxy-deoxybenzoin (810661-50-8) → 3,4-diethoxy-benzil-α'-oxime

Conditions	Yield
With hydrogenchloride; benzene

nitrous acid isobutyl ester (542-56-3) + N-(2-Hydroxy-phenyl)-N'''-phenyl-3-undecyl-formazan → 2-(2-hydroxy-phenyl)-3-phenyl-5-undecyl-tetrazolium; chloride

Conditions	Yield
With hydrogenchloride; methanol

nitrous acid isobutyl ester (542-56-3) + β-(N,N-diethylamino)propiophenone hydrochloride (884-12-8) → 3-diethylamino-1-phenyl-propane-1,2-dione-2-oxime (101265-02-5)

Conditions	Yield
With hydrogenchloride; methanol

nitrous acid isobutyl ester (542-56-3) + 3-dipropylamino-1-phenyl-propan-1-one; hydrochloride (101356-15-4) → 3-dipropylamino-1-phenyl-propane-1,2-dione-2-oxime

Conditions	Yield
With hydrogenchloride; methanol

nitrous acid isobutyl ester (542-56-3) + 3-(benzyl methylamino)-1-phenylpropan-1-one hydrochloride (5409-62-1) → 3-(benzyl-methyl-amino)-1-phenyl-propane-1,2-dione-2-oxime

Conditions	Yield
With hydrogenchloride; methanol

nitrous acid isobutyl ester (542-56-3) + 1-phenyl-3-piperidino-propan-1-one; hydrochloride (886-06-6) → 1-phenyl-3-piperidino-propane-1,2-dione-2-oxime (108488-77-3)

Conditions	Yield
With hydrogenchloride

nitrous acid isobutyl ester (542-56-3) → Isobutyronitrile (78-82-0)

Conditions	Yield
With hydrogen; nickel at 320 - 330℃;

nitrous acid isobutyl ester (542-56-3) → isopropyl radical (2025-55-0)

Conditions	Yield
at 475℃;

nitrous acid isobutyl ester (542-56-3) → trans-nitrosomethane dimer (2717-67-1, 17606-84-7, 37765-15-4)

Conditions	Yield
Irradiation.mit UV-Licht; trans-dimethyl-diazene dioxide;

nitrous acid isobutyl ester (542-56-3) → (i-PrNO)2 (57527-63-6, 92670-22-9)

Conditions	Yield
Pyrolysis; cis-diisopropyl-diazene dioxide;

Upstream product

• 78-83-1 2-methyl-propan-1-ol 
• 78-77-3 Isobutyl bromide 
• 513-38-2 Isobutyl iodide 
• 26397-34-2 isobutyloxyl 
• 1487-15-6 2-Methyl-4,5-dihydrofuran 
• 7782-77-6 cis-nitrous acid 

Downstream Products

• 78-81-9 isobutylamine 
• 110-96-3 diisobutylamine 
• 78-82-0 Isobutyronitrile 
• 78-84-2 isobutyraldehyde 
• 50-00-0 formaldehyd 
• 300350-24-7 2,4,4'-trichloro-2'-bromodiphenyl ether 
• 452-62-0 3-bromo-4-fluorotoluene 
• 10102-43-9 nitrogen(II) oxide 
• 13325-10-5 4-Aminobutanol 
• 27739-28-2 iso-butyl 4-methoxybenzoate 
• 1202890-02-5 ethyl 8-bromo-7-(4-(tert-butoxycarbonyl)phenoxy)-6-chlorochroman-4-carboxylate 
• 162823-37-2 3-oximino-2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one-1-acetic acid 

Relevant articles and documents

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Preparation method of 4-(BOC-amino)-1-butanol

The invention discloses a preparation method of 4-(BOC-amino)-1-butanol. The method comprises the following steps: reacting a proper amount of 2, 3-dihydrofuran with an acidic solution to obtain 2, 3-dihydro-5-methyl furan; mixing the obtained 2, 3-dihydro-5-methyl furan with hydrochloride, and then adding the mixture into an alkaline solution for reaction to obtain isobutyl nitrite; reacting isobutyl nitrite under the action of a reducing agent to generate 4-amino-1-butyl alcohol; and reacting 4-amino-1-butyl alcohol with di-tert-butyl dicarbonate in tetrahydrofuran to generate 4-(BOC-amino)-1-butyl alcohol; according to the preparation method of the 4-(BOC-amino)-1-butanol, the total yield of the product is as high as 70%, the reaction temperature is low, and the safety coefficient is high), the reducing agent is cheaper than that in the prior art, the experimental operation method is simple, the steps are short, and the method is suitable for large-scale production.

Reaction of alcohol with NO2 on a Cleaned Glass Surface

Formation of alkyl nitrite from alcohol and NO2 was very fast on a Pyrex glass surface cleaned with chromic acid mixture.The reaction was practically zero order with respect to NO2.The rate constant was (1.7 +/- 0.08)*10E-18 cm3*molecule-1*s-1 for methyl nitrile formation and the apparent activation energy was -53.5 kJ*mol-1.

A kinetic study of the influence of alcohols on the nitrosation of morpholine in acid media. Equilibrium constants for the formation of alkyl nitrites

The effect of the aliphatic alcohols methanol, ethanol, propanol, isopropanol, 2-butanol, isobutanol, and tert-butanol on the rate of nitrosation of morpholine at pH 3 and 25 deg C has been studied.The inhibition observed is attributed to the formation of alkyl nitrites, which are poor nitrosating agents in acid media.The equilibrium constants for the formation of alkyl nitrites from nitrous acid and alcohols have been calculated both spectrophotometrically and from kinetic data for the inhibitory effect, and there is agreement between the two sets of results.The molar absorptivities at 265 nm of the alkyl nitrites have also been determined.When the concentration of alkyl nitrite is very low, a slight catalytic effect considered to be an effect of the medium has been observed.