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Names | |
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Preferred IUPAC name tert-Butyl hypochlorite | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.007.339 |
EC Number |
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PubChem CID | |
UNII | |
UN number | 3255 |
CompTox Dashboard (EPA) | |
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Properties | |
C4H9ClO | |
Molar mass | 108.57 g·mol−1 |
Appearance | Yellow liquid |
Density | 0.9583 g/cm3 |
Boiling point | 79.6 °C (175.3 °F; 352.8 K) explosive |
Sparingly | |
Hazards | |
GHS labelling: | |
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Danger | |
H225, H250, H251, H271, H314, H334 | |
P210, P220, P221, P222, P233, P235+P410, P240, P241, P242, P243, P260, P261, P264, P280, P283, P285, P301+P330+P331, P302+P334, P303+P361+P353, P304+P340, P304+P341, P305+P351+P338, P306+P360, P310, P321, P342+P311, P363, P370+P378, P371+P380+P375, P403+P235, P405, P407, P413, P420, P422, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
tert-Butyl hypochlorite is the organic compound with the formula (CH3)3COCl. A yellow liquid, it is a rare example of an organic hypochlorite, i.e. a compound with an O-Cl bond. It is a reactive material that is useful for chlorinations. It can be viewed as a lipophilic version of sodium hypochlorite (bleach). [1]
It is produced by chlorination of tert-butyl alcohol in the presence of base: [2] [3]
tert-Butyl hypochlorite is useful in the preparation of organic chloramines: [4]
In chemistry, hypochlorite, or chloroxide is an anion with the chemical formula ClO−. It combines with a number of cations to form hypochlorite salts. Common examples include sodium hypochlorite and calcium hypochlorite. The Cl-O distance in ClO− is 1.69 Å.
An isocyanide is an organic compound with the functional group –N+≡C−. It is the isomer of the related nitrile (–C≡N), hence the prefix is isocyano. The organic fragment is connected to the isocyanide group through the nitrogen atom, not via the carbon. They are used as building blocks for the synthesis of other compounds.
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.
1-Bromobutane is the organobromine compound with the formula CH3(CH2)3Br. It is a colorless liquid, although impure samples appear yellowish. It is insoluble in water, but soluble in organic solvents. It is primarily used as a source of the butyl group in organic synthesis. It is one of several isomers of butyl bromide.
Hydroperoxides or peroxols are compounds of the form ROOH, where R stands for any group, typically organic, which contain the hydroperoxy functional group. Hydroperoxide also refers to the hydroperoxide anion and its salts, and the neutral hydroperoxyl radical (•OOH) consist of an unbond hydroperoxy group. When R is organic, the compounds are called organic hydroperoxides. Such compounds are a subset of organic peroxides, which have the formula ROOR. Organic hydroperoxides can either intentionally or unintentionally initiate explosive polymerisation in materials with unsaturated chemical bonds.
tert-Butyllithium is a chemical compound with the formula (CH3)3CLi. As an organolithium compound, it has applications in organic synthesis since it is a strong base, capable of deprotonating many carbon molecules, including benzene. tert-Butyllithium is available commercially as solutions in hydrocarbons (such as pentane); it is not usually prepared in the laboratory.
Trimethylsilyl cyanide is the chemical compound with the formula (CH3)3SiCN. This volatile liquid consists of a cyanide group, that is CN, attached to a trimethylsilyl group. The molecule is used in organic synthesis as the equivalent of hydrogen cyanide. It is prepared by the reaction of lithium cyanide and trimethylsilyl chloride:
Chloramines refer to derivatives of ammonia and organic amines wherein one or more N−H bonds have been replaced by N−Cl bonds. Two classes of compounds are considered: inorganic chloramines and organic chloramines. Chloramines are the most widely used members of the halamines.
The Sharpless oxyamination is the chemical reaction that converts an alkene to a vicinal amino alcohol. The reaction is related to the Sharpless dihydroxylation, which converts alkenes to vicinal diols. Vicinal amino-alcohols are important products in organic synthesis and recurring pharmacophores in drug discovery.
Pivalic acid is a carboxylic acid with a molecular formula of (CH3)3CCO2H. This colourless, odiferous organic compound is solid at room temperature. Two abbreviations for pivalic acid are t-BuC(O)OH and PivOH. The pivalyl or pivaloyl group is abbreviated t-BuC(O).
sec-Butyllithium is an organometallic compound with the formula CH3CHLiCH2CH3, abbreviated sec-BuLi or s-BuLi. This chiral organolithium reagent is used as a source of sec-butyl carbanion in organic synthesis.
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.
tert-Butylamine (also erbumine and other names) is an organic chemical compound with the formula (CH3)3CNH2. It is a colorless liquid with a typical amine-like odor. tert-Butylamine is one of the four isomeric amines of butane, the others being n-butylamine, sec-butylamine and isobutylamine.
Trimethyltin chloride is an organotin compound with the formula (CH3)3SnCl. It is a white solid that is highly toxic and malodorous. It is susceptible to hydrolysis.
tert-Butyl isocyanide is an organic compound with the formula Me3CNC (Me = methyl, CH3). It is an isocyanide, commonly called isonitrile or carbylamine, as defined by the functional group C≡N-R. tert-Butyl isocyanide, like most alkyl isocyanides, is a reactive colorless liquid with an extremely unpleasant odor. It forms stable complexes with transition metals and can insert into metal-carbon bonds.
Diethyl chlorophosphate is an organophosphorus compound with the formula (C2H5O)2P(O)Cl. As a reagent in organic synthesis, it is used to convert alcohols to the corresponding diethylphosphate esters. It is a colorless liquid with a fruity odor. It is a corrosive, and as a cholinesterase inhibitor, highly toxic through dermal absorption. The molecule is tetrahedral.
Vinyllithium is an organolithium compound with the formula LiC2H3. A colorless or white solid, it is encountered mainly as a solution in tetrahydrofuran (THF). It is a reagent in synthesis of organic compounds, especially for vinylations.
Diethyl phosphite is the organophosphorus compound with the formula (C2H5O)2P(O)H. It is a popular reagent for generating other organophosphorus compounds, exploiting the high reactivity of the P-H bond. Diethyl phosphite is a colorless liquid. The molecule is tetrahedral.
tert-Butyldimethylsilyl chloride is an organosilicon compound with the formula (Me3C)Me2SiCl (Me = CH3). It is commonly abbreviated as TBSCl or TBDMSCl. It is a chlorosilane containing two methyl groups and a tert-butyl group. As such it is more bulky that trimethylsilyl chloride. It is a colorless or white solid that is soluble in many organic solvents but reacts with water and alcohols. The compound is used to protect alcohols in organic synthesis.
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.