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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:
110-46-3
Molecular Weight:
117.15
Beilstein:
969510
EC Number:
203-770-8
MDL number:
MFCD00002057
UNSPSC Code:
12171500
PubChem Substance ID:
24849038
NACRES:
NA.47

Quality Level

200

Assay

96%

form

liquid

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.
  • as a reagent in the preparation of 4-carboxy-phenyl diazonium salt tetrafluoroborate.
  • in the synthesis of peroxynitrite (ONOO-).
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.

Signal Word

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

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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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)
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)
Tetrahedron Letters, 31, 1113-1113 (1990)
Hossein Mehrabi
Ultrasonics sonochemistry, 15(4), 279-282 (2007-10-26)
The reaction of 6-acylmethylphenanthridines with isoamyl nitrite results alpha-oximino-6-acylmethylphenanthridines in 73-95% yields in DMF under ultrasound irradiation. Compared with conventional methods, the main advantages of the present procedure are milder conditions, shorter reaction time and higher yields.
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