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235385

Sigma-Aldrich

tert-Butyl nitrite

90%

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Synonym(s):
1,1-Dimethylethyl nitrite
Linear Formula:
(CH3)3CONO
CAS Number:
Molecular Weight:
103.12
Beilstein:
1209339
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

90%

refractive index

n20/D 1.368 (lit.)

bp

61-63 °C (lit.)

solubility

alcohol: very soluble(lit.)
carbon disulfide: very soluble(lit.)
chloroform: very soluble(lit.)
diethyl ether: very soluble(lit.)
glycerol: insoluble (practically)(lit.)
water: slightly soluble(lit.)

density

0.867 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)(C)ON=O

InChI

1S/C4H9NO2/c1-4(2,3)7-5-6/h1-3H3

InChI key

IOGXOCVLYRDXLW-UHFFFAOYSA-N

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This Item
2037011625229415
tert-Butyl nitrite 90%

Sigma-Aldrich

235385

tert-Butyl nitrite

tert-Butyl nitrite technical, ≥90% (GC)

Sigma-Aldrich

20370

tert-Butyl nitrite

refractive index

n20/D 1.368 (lit.)

refractive index

n20/D 1.368 (lit.)

refractive index

-

refractive index

-

bp

61-63 °C (lit.)

bp

61-63 °C (lit.)

bp

-

bp

135 °C (lit.)

solubility

alcohol: very soluble(lit.), carbon disulfide: very soluble(lit.), chloroform: very soluble(lit.), diethyl ether: very soluble(lit.), glycerol: insoluble (practically)(lit.), water: slightly soluble(lit.)

solubility

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

solubility

-

solubility

ethanol: very soluble(lit.)

density

0.867 g/mL at 25 °C (lit.)

density

0.864 g/mL at 20 °C, 0.867 g/mL at 25 °C (lit.)

density

-

density

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

General description

tert-Butyl nitrite (TBN) is an efficient NO source. TBN participates in photocatalyzed conversion of aryl- and heteroarylamines to selenides. It also participates in radical multifunctionalization reactions of aliphatic alkenes.

Application

tert-Butyl nitrite has been used as reagent:
  • for diazotization and nitros­ation of alcohols, thiols, amines and cycloalkanes
  • for the preparation of aryl azides from aryl amines

Other Notes

remainder 2-methyl-2-propanol

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

14.0 °F - closed cup

Flash Point(C)

-10 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Daisuke Hirose et al.
Beilstein journal of organic chemistry, 9, 1713-1717 (2013-09-26)
Water induces a change in the product of radical multifunctionalization reactions of aliphatic alkenes involving an sp(3) C-H functionalization by an 1,5-hydrogen shift using tert-butyl nitrite and molecular oxygen. The reaction without water, reported previously, gives nitrated γ-lactols, whereas the
The Journal of Organic Chemistry, 42, 2426-2426 (1977)
tert-Butyl Nitrite.
Liu Y.
Synlett, 2011(08), 1184-1185 (2011)
The Journal of Organic Chemistry, 42, 3494-3494 (1977)
The Journal of Organic Chemistry, 42, 2431-2431 (1977)

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