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150495

Sigma-Aldrich

Isopentyl nitrite

96%

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Synonym(s):
Isoamyl nitrite
Linear Formula:
(CH3)2CHCH2CH2ONO
CAS Number:
Molecular Weight:
117.15
Beilstein/REAXYS Number:
969510
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.47

Quality Level

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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This Item
4912682037079857
Isopentyl nitrite 96%

150495

Isopentyl nitrite

Isoamyl nitrite-15N 98 atom % 15N, 97% (CP)

491268

Isoamyl nitrite-15N

tert-Butyl nitrite technical, &#8805;90% (GC)

20370

tert-Butyl nitrite

Isopentyl acetate analytical standard

79857

Isopentyl acetate

application(s)

diagnostic assay manufacturing
hematology
histology

application(s)

-

application(s)

-

application(s)

cleaning products
cosmetics
environmental
flavors and fragrances
food and beverages
personal care

form

liquid

form

-

form

liquid

form

-

solubility

water: soluble 0.38 g/L at 25 °C

solubility

-

solubility

alcohol: very soluble, chloroform: very soluble, diethyl ether: very soluble, glycerol: insoluble, water: slightly soluble

solubility

-

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

-

assay

96%

assay

97% (CP)

assay

≥90% (GC)

assay

≥99.7% (GC)

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.

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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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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