Nonafluoro-tert-butyl alcohol

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Nonafluoro-tert-butyl alcohol
Nonafluoro-tert-butanol.png
Names
Preferred IUPAC name
1,1,1,3,3,3-Hexafluoro-2-(trifluoromethyl)propan-2-ol
Other names
perfluoro-tert-butyl alcohol, perfluoro-tert-butanol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.017.417 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 219-157-3
PubChem CID
  • InChI=1S/C4HF9O/c5-2(6,7)1(14,3(8,9)10)4(11,12)13/h14H
  • OC(C(F)(F)F)(C(F)(F)F)C(F)(F)F
Properties
C4F9OH
Molar mass 236.04 g/mol
AppearanceColorless liquid
Boiling point 45 °C (113 °F; 318 K)
Miscible
Acidity (pKa)5.4 (in H2O)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Corrosive, eye irritant
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Nonafluoro-tert-butyl alcohol (IUPAC name: 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol) is a fluoroalcohol. It is the perfluorinated analog of tert-butyl alcohol. Notably, as a consequence of its electron withdrawing fluorine substituents, it is very acidic for an alcohol, with a pKa value of 5.4, similar to that of a carboxylic acid. As another consequence of being a perfluorinated compound, it is also one of the lowest boiling alcohols, with a boiling point lower than that of methanol.

Contents

Synthesis

It is prepared by addition of trichloromethyllithium to hexafluoroacetone, followed by halogen exchange with antimony pentafluoride. [1] The aluminate derived from its alkoxide anion, tetrakis[1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-oxy]aluminate(1–), {Al[(CF3)3CO]4} is used as a weakly coordinating anion. [2]

See also

Related Research Articles

<span class="mw-page-title-main">Alcohol (chemistry)</span> Organic compound with at least one hydroxyl (–OH) group

In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl functional group bound to a saturated carbon atom. Alcohols range from the simple, like methanol and ethanol, to complex, like sucrose and cholesterol. The presence of an OH group strongly modifies the properties of hydrocarbons, conferring hydrophilic (water-loving) properties. The OH group provides a site at which many reactions can occur.

Butanol (also called butyl alcohol) is a four-carbon alcohol with a formula of C4H9OH, which occurs in five isomeric structures (four structural isomers), from a straight-chain primary alcohol to a branched-chain tertiary alcohol; all are a butyl or isobutyl group linked to a hydroxyl group (sometimes represented as BuOH, n-BuOH, i-BuOH, and t-BuOH). These are n-butanol, 2 stereoisomers of sec-butanol, isobutanol and tert-butanol. Butanol is primarily used as a solvent and as an intermediate in chemical synthesis, and may be used as a fuel. Biologically produced butanol is called biobutanol, which may be n-butanol or isobutanol.

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.

The Hofmann rearrangement is the organic reaction of a primary amide to a primary amine with one less carbon atom. The reaction involves oxidation of the nitrogen followed by rearrangement of the carbonyl and nitrogen to give an isocyanate intermediate. The reaction can form a wide range of products, including alkyl and aryl amines.

<span class="mw-page-title-main">Hexafluoro-2-propanol</span> Chemical compound

Hexafluoroisopropanol, commonly abbreviated HFIP, is the organic compound with the formula (CF3)2CHOH. This fluoroalcohol finds use as solvent in organic chemistry. Hexafluoro-2-propanol is transparent to UV light with high density, low viscosity and low refractive index. It is a colorless, volatile liquid with a pungent odor.

<span class="mw-page-title-main">2-Butanol</span> Secondary alcohol

2-Butanol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. Its structural isomers are 1-butanol, isobutanol, and tert-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-2-butanol and (S)-(+)-2-butanol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.

Anions that interact weakly with cations are termed non-coordinating anions, although a more accurate term is weakly coordinating anion. Non-coordinating anions are useful in studying the reactivity of electrophilic cations. They are commonly found as counterions for cationic metal complexes with an unsaturated coordination sphere. These special anions are essential components of homogeneous alkene polymerisation catalysts, where the active catalyst is a coordinatively unsaturated, cationic transition metal complex. For example, they are employed as counterions for the 14 valence electron cations [(C5H5)2ZrR]+ (R = methyl or a growing polyethylene chain). Complexes derived from non-coordinating anions have been used to catalyze hydrogenation, hydrosilylation, oligomerization, and the living polymerization of alkenes. The popularization of non-coordinating anions has contributed to increased understanding of agostic complexes wherein hydrocarbons and hydrogen serve as ligands. Non-coordinating anions are important components of many superacids, which result from the combination of Brønsted acids and Lewis acids.

<i>tert</i>-Butyl alcohol Chemical compound

tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

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

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Di-<i>tert</i>-butyl dicarbonate Chemical compound

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.

Pivalic acid, also known as neovaleric acid, is a carboxylic acid with a molecular formula of (CH3)3CCO2H. This colourless, odiferous organic compound is solid at room temperature. A common abbreviation for the pivalyl or pivaloyl group (t-BuC(O)) is Piv and for pivalic acid (t-BuC(O)OH) is PivOH. It is an isomer of valeric acid, the other two isomers of it are 2-Methylbutanoic acid and 3-Methylbutanoic acid.

tert-Butyl chloride is the organochloride with the formula (CH3)3CCl. It is a colorless, flammable liquid. It is sparingly soluble in water, with a tendency to undergo hydrolysis to the corresponding tert-butyl alcohol. It is produced industrially as a precursor to other organic compounds.

Isopropyl alcohol is a colorless, flammable organic compound with a pungent alcoholic odor. As an isopropyl group linked to a hydroxyl group it is the simplest example of a secondary alcohol, where the alcohol carbon atom is attached to two other carbon atoms. It is a structural isomer of propan-1-ol and ethyl methyl ether.

<span class="mw-page-title-main">Perfluorinated compound</span>

A perfluorinated compound (PFC) or perfluoro compound is an organofluorine compound lacking C-H bonds. Many perfluorinated compounds have properties that are quite different from their C-H containing analogues. Common functional groups in PFCs are OH, CO2H, chlorine, O, and SO3H. Electrofluorination is the predominant method for their production. Due to their chemical stability, some of these perfluorinated compounds bioaccumulate.

<span class="mw-page-title-main">Jones oxidation</span> Oxidation of alcohol

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Ether cleavage refers to chemical substitution reactions that lead to the cleavage of ethers. Due to the high chemical stability of ethers, the cleavage of the C-O bond is uncommon in the absence of specialized reagents or under extreme conditions.

2,4,6-Tri-<i>tert</i>-butylphenol Chemical compound

2,4,6-Tri-tert-butylphenol (2,4,6-TTBP) is a phenol symmetrically substituted with three tert-butyl groups and thus strongly sterically hindered. 2,4,6-TTBP is a readily oxidizable aromatic compound and a weak acid. It oxidizes to give the deep-blue 2,4,6-tri-tert-butylphenoxy radical. 2,4,6-TTBP is related to 2,6-di-tert-butylphenol, which is widely used as an antioxidant in industrial applications. These compounds are colorless solids.

Fluoroalcohols are organofluorine compounds consisting of an alcohol functional group with at least one C-F bond. These compounds often have distinctive solvent properties.

<i>tert</i>-Butyl nitrite Chemical compound

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.

References

  1. Filler, Robert; Schure, Ralph M. (1967-04-01). "Highly acidic perhalogenated alcohols. A new synthesis of perfluoro-tert-butyl alcohol". The Journal of Organic Chemistry. 32 (4): 1217–1219. doi:10.1021/jo01279a081. ISSN   0022-3263.
  2. Krossing, Ingo; Raabe, Ines (2004-04-13). "Noncoordinating Anions—Fact or Fiction? A Survey of Likely Candidates". Angewandte Chemie International Edition. 43 (16): 2066–2090. doi:10.1002/anie.200300620. ISSN   1433-7851. PMID   15083452.