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20370

Sigma-Aldrich

tert-Butyl nitrite

technical, ≥90% (GC)

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:
329752006
NACRES:
NA.22
Pricing and availability is not currently available.

grade

technical

Quality Level

200

Assay

≥90% (GC)

form

liquid

impurities

≤8% tert-butyl alcohol

refractive index

n20/D 1.368 (lit.)
n20/D 1.368

bp

61-63 °C (lit.)

solubility

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

density

0.864 g/mL at 20 °C
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 is an organic building block widely used in various organic transformations such as oxidation, diazotization, nitrosation, nitration, oximation, N-synthon, and miscellaneous reactions[1].

Application

tert-Butyl nitrite can be used as a reactant to synthesize aryl diazonium salts via diazotation[2].

Other Notes

Reagent for nitrosations, kinetics[3]; Clean source of Me3C radicals by near-UV photolysis[4]

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
BCCG6034
BCCF0154
BCCC3995
BCCB6099

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L. Batt et al.
International Journal of Chemical Kinetics, 21, 535-535 (1989)
Quantum defects as versatile anchors for carbon nanotube functionalization
Mann F, et al.
Nature Protocols, 17, 727-747 (2022)
tert-Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis
Dahiya A, et al.
Chemistry - An Asian Journal, 14, 4454-4492 (2019)
M.J. Crookes et al.
J. Chem. Soc. Perkin Trans. II, 1339-1339 (1988)
Brenden Kilpatrick et al.
Chemical communications (Cambridge, England), 49(5), 514-516 (2012-12-01)
A methodology for the efficient conversion of aromatic sulfonamides into their mono-nitro derivatives using tert-butyl nitrite is reported. The reaction exhibits a high degree of chemoselectivity for sulfonamide functionalized aryl systems, even in the presence of other sensitive or potentially

Questions

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  1. 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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  2. 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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