Tert-Butyl nitrite

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tert-Butyl nitrite
Tert-butyl-nitrite-2D-dimensions.svg
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.962 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-757-0
PubChem CID
UNII
  • InChI=1S/C4H9NO2/c1-4(2,3)7-5-6/h1-3H3
    Key: IOGXOCVLYRDXLW-UHFFFAOYSA-N
  • CC(C)(C)ON=O
Properties
C4H9NO2
Molar mass 103.121 g·mol−1
Appearancecolorless liquid
Boiling point 61–63 °C (142–145 °F; 334–336 K)
Hazards
GHS labelling: [1]
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Danger
H225, H302, H332
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P303+P361+P353, P304+P312, P304+P340, P312, P330, P370+P378, P403+P235, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

tert-Butyl nitrite is an organic compound with the formula (CH3)3CONO. A colorless liquid, it is the tert-butyl ester of nitrous acid. It is typically employed as a solution with tert-butyl alcohol.

Contents

Use

The compound is used as a reagent in organic synthesis. [2] It reacts with secondary amides to give N-nitroso amides: [3]

RC(O)N(H)R + (CH3)3CONO → RC(O)N(NO)R + (CH3)3COH

See also

Related Research Articles

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In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula R−C(=O)−NR′R″, where R, R', and R″ represent any group, typically organyl groups or hydrogen atoms. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. It can be viewed as a derivative of a carboxylic acid with the hydroxyl group replaced by an amine group ; or, equivalently, an acyl (alkanoyl) group joined to an amine group.

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

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In organic chemistry, thioesters are organosulfur compounds with the molecular structure R−C(=O)−S−R’. They are analogous to carboxylate esters with the sulfur in the thioester replacing oxygen in the carboxylate ester, as implied by the thio- prefix. They are the product of esterification of a carboxylic acid with a thiol. In biochemistry, the best-known thioesters are derivatives of coenzyme A, e.g., acetyl-CoA. The R and R' represent organyl groups, or H in the case of R.

In organic chemistry, butyl is a four-carbon alkyl radical or substituent group with general chemical formula −C4H9, derived from either of the two isomers (n-butane and isobutane) of butane.

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Butyl nitrite is the organic compound with the formula CH3(CH2)3ONO. It is an alkyl nitrite made from n-butanol. Butyl nitrite is used recreationally as poppers. Synonyms include 1-butyl nitrite, n-butyl nitrite and nitrous acid butyl ester.

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Dimethyl sulfate (DMS) is a chemical compound with formula (CH3O)2SO2. As the diester of methanol and sulfuric acid, its formula is often written as (CH3)2SO4 or Me2SO4, where CH3 or Me is methyl. Me2SO4 is mainly used as a methylating agent in organic synthesis.

<span class="mw-page-title-main">Sodium bis(trimethylsilyl)amide</span> Chemical compound

Sodium bis(trimethylsilyl)amide is the organosilicon compound with the formula NaN(Si 3)2. This species, usually called NaHMDS, is a strong base used for deprotonation reactions or base-catalyzed reactions. Its advantages are that it is commercially available as a solid and it is soluble not only in ethers, such as THF or diethyl ether, but also in aromatic solvents, like benzene and toluene by virtue of the lipophilic TMS groups.

<span class="mw-page-title-main">Knorr pyrrole synthesis</span> Chemical reaction

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Di-tert-butyl dicarbonate is a reagent widely used in organic synthesis. Since this compound can be regarded formally as the acid anhydride derived from a tert-butoxycarbonyl (Boc) group, it is commonly referred to as Boc anhydride. This pyrocarbonate reacts with amines to give N-tert-butoxycarbonyl or so-called Boc derivatives. These carbamate derivatives do not behave as amines, which allows certain subsequent transformations to occur that would be incompatible with the amine functional group. The Boc group can later be removed from the amine using moderately strong acids. Thus, Boc serves as a protective group, for instance in solid phase peptide synthesis. Boc-protected amines are unreactive to most bases and nucleophiles, allowing for the use of the fluorenylmethyloxycarbonyl group (Fmoc) as an orthogonal protecting group.

<span class="mw-page-title-main">Trimethylsilyl cyanide</span> Chemical compound

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<i>tert</i>-Butyloxycarbonyl protecting group Protecting group used in organic synthesis

The tert-butyloxycarbonyl protecting group or tert-butoxycarbonyl protecting group is a protecting group used in organic synthesis.

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<span class="mw-page-title-main">2,6-Lutidine</span> Chemical compound

2,6-Lutidine is a natural heterocyclic aromatic organic compound with the formula (CH3)2C5H3N. It is one of several dimethyl-substituted derivative of pyridine, all of which are referred to as lutidines. It is a colorless liquid with mildly basic properties and a pungent, noxious odor.

In chemistry, hyponitrite may refer to the anion N
2
O2−
2
([ON=NO]2−), or to any ionic compound that contains it. In organic chemistry, it may also refer to the group −O−N=N−O−, or any organic compound with the generic formula R1−O−N=N−O−R2, where R1 and R2 are organic groups. Such compounds can be viewed as salts and esters of respectively hyponitrous acid H
2
N
2
O
2
or HON=NOH.

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<i>tert</i>-Butylthiol Chemical compound

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References

  1. "tert-Butyl nitrite". pubchem.ncbi.nlm.nih.gov. Retrieved 2 February 2022.
  2. Di Qiu, He Meng, Liang Jin, Shengbo Tang, Shuai Wang, Fangyang Mo, Yan Zhang, Jianbo Wang (2014). "Synthesis of Arylboronic Pinacol Esters from Corresponding Arylamines". Organic Syntheses. 91: 106. doi: 10.15227/orgsyn.091.0106 .{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. Yedage, Subhash L.; Bhanage, Bhalchandra M. (2017). "Tert-Butyl Nitrite-Mediated Synthesis of N-Nitrosoamides, Carboxylic Acids, Benzocoumarins, and Isocoumarins from Amides". The Journal of Organic Chemistry. 82 (11): 5769–5781. doi:10.1021/acs.joc.7b00570. PMID   28472882.