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150495

Sigma-Aldrich

Isopentyl nitrite

96%

Synonym(s):

Isoamyl nitrite

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5 ML
$40.68
100 ML
$57.96
500 ML
$197.10

About This Item

Linear Formula:
(CH3)2CHCH2CH2ONO
CAS Number:
110-46-3
Molecular Weight:
117.15
Beilstein/REAXYS Number:
969510
EC Number:
203-770-8
MDL number:
MFCD00002057
UNSPSC Code:
12171500
PubChem Substance ID:
24849038
NACRES:
NA.47

$40.68

List Price$45.20Save 10%
Web-Only Promotion

Available to ship onApril 29, 2025Details

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Quality Level

200

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.)

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

2-8°C

SMILES string

CC(C)CCON=O

InChI

1S/C5H11NO2/c1-5(2)3-4-8-6-7/h5H,3-4H2,1-2H3

InChI key

OWFXIOWLTKNBAP-UHFFFAOYSA-N

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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.

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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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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ9632
BCCG2054
BCCD4387
BCBX0122
BCBV1096

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Electron transfer at Au surfaces modified by Tethered Osmium bipyridine?pyridine complexes
Journal of Solid State Electrochemistry, 11:11, 1511-1520 null
New insights into the functionalization of multi-walled carbon
nanotubes with aniline derivatives
Lipinska M E
Carbon, 50, 3280 -33294 (2012)
Tetrahedron Letters, 31, 1113-1113 (1990)
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)
R M Uppu et al.
Analytical biochemistry, 236(2), 242-249 (1996-05-01)
A new method for the preparation of high concentrations of peroxynitrite (up to 1 M) is described. The synthesis uses a two-phase system and involves a displacement reaction by the hydroperoxide anion (in the aqueous phase) on isoamyl nitrite (in
View All Related Papers

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