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235385

Sigma-Aldrich

tert-Butyl nitrite

90%

Synonym(s):

1,1-Dimethylethyl nitrite

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25 ML
$52.10
100 ML
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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%

$52.10

Please contact Customer Service for Availability
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Quality Level

200

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.)

functional group

O-nitroso
nitroso

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[1]. TBN participates in photocatalyzed conversion of aryl- and heteroarylamines to selenides[2]. It also participates in radical multifunctionalization reactions of aliphatic alkenes[3].

Application

tert-Butyl nitrite has been used as reagent:
  • for diazotization and nitros­ation of alcohols, thiols, amines and cycloalkanes[1]
  • for the preparation of aryl azides from aryl amines[4]

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG9576
BCCG6710
BCCG6034
BCCF0154
BCCC3995

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The Journal of Organic Chemistry, 42, 2426-2426 (1977)
tert-Butyl Nitrite.
Liu Y.
Synlett, 2011(08), 1184-1185 (2011)
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, 3494-3494 (1977)
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
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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