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150495

Sigma-Aldrich

Isopentyl nitrite

96%

Synonym(s):

Isoamyl nitrite

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About This Item

Linear Formula:
(CH3)2CHCH2CH2ONO
CAS Number:
Molecular Weight:
117.15
Beilstein/REAXYS Number:
969510
EC Number:
MDL number:
UNSPSC Code:
12171500
PubChem Substance ID:
NACRES:
NA.47

Quality Level

assay

96%

form

liquid

technique(s)

titration: suitable

color

colorless to green-yellow
colorless to yellow

refractive index

n20/D 1.386 (lit.)

bp

99 °C (lit.)

mp

<-80 °C

solubility

water: soluble 0.38 g/L at 25 °C

density

0.872 g/mL at 25 °C (lit.)

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General description

Isopentyl nitrite, also known as isoamyl nitrite, is an oxidant, and nitrosating agent for phosphoramidites which rearrange into phosphotriesters during nitrosation.

Application

Isopentyl nitrite has been used:
  • as a radical initiator to functionalize multi-walled carbon nanotubes.[1]
  • as a reagent in the preparation of 4-carboxy-phenyl diazonium salt tetrafluoroborate.[2]
  • in the synthesis of peroxynitrite (ONOO-).[3]
Isopentyl nitrite, also known as isoamyl nitrite, is used for the generation of benzyne from anthranilic acid. It is a smooth muscle relaxant that may be suitable as nitrovasodilators and as recreational drugs known as poppers. Its applications are also seen in kits to treat cyanide poisoning, its function being to oxidize hemoglobin (Hb) to methemoglobin (metHb) which reacts with cyanide to form the non-toxic cyano-metHb.

signalword

Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Muta. 2 - Skin Corr. 1B - Skin Sens. 1

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

-4.0 °F - closed cup

flash_point_c

-20 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Comparing nitrosative versus oxidative stress toward zinc finger-dependent transcription. Unique role for NO.
Kroncke KD
The Journal of Biological Chemistry, 277(15), 13294-13301 (2002)
Electron transfer at Au surfaces modified by Tethered Osmium bipyridine?pyridine complexes
Journal of Solid State Electrochemistry, 11:11, 1511-1520 null
Tetrahedron Letters, 31, 1113-1113 (1990)
New insights into the functionalization of multi-walled carbon
nanotubes with aniline derivatives
Lipinska M E
Carbon, 50, 3280 -33294 (2012)
V M Ramanathan et al.
Journal of toxicology and environmental health. Part A, 55(5), 345-358 (1998-11-26)
Isoamyl nitrite (IAN) is a member of the family of volatile organic nitrites that exert vasodilatory effects and have recently exhibited a considerable potential for inhalation abuse. In an effort to provide mechanistic insight into the neurotoxic effects and abuse

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