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Sigma-Aldrich

tert-Butyl nitrite

90%

Synonym(s):

1,1-Dimethylethyl nitrite

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About This Item

Linear Formula:
(CH3)3CONO
CAS Number:
540-80-7
Molecular Weight:
103.12
Beilstein:
1209339
EC Number:
208-757-0
MDL number:
MFCD00002055
UNSPSC Code:
12352100
PubChem Substance ID:
24854101
NACRES:
NA.22

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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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
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H302 + H332

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
tert-Butyl Nitrite.
Liu Y.
Synlett, 2011(08), 1184-1185 (2011)
Karine Barral et al.
Organic letters, 9(9), 1809-1811 (2007-03-30)
[reaction: see text] An efficient and improved procedure for the preparation of aromatic azides and their application in the Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition ("click reaction") is described. The synthesis of aromatic azides from the corresponding amines is accomplished under mild
Debasish Kundu et al.
Organic letters, 16(6), 1814-1817 (2014-03-14)
A novel strategy for the direct conversion of aryl- and heteroarylamines to selenides has been developed via diazotization of amines with tert-butyl nitrite in neutral medium followed by reaction with diaryl/diheteroaryl/dialkyl diselenides in one pot under photocatalysis at room temperature
The Journal of Organic Chemistry, 42, 2431-2431 (1977)
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