Tert-Amyl chloride

Last updated
tert-Amyl chloride [1]
2-Chloro-2-methylbutane Structural Formula V1.svg
Tert-amyl chloride-3D-balls.png
Names
Preferred IUPAC name
2-Chloro-2-methylbutane
Other names
1,1-Dimethylpropyl chloride; 2-Methyl-2-chlorobutane; tert-Pentyl chloride; t-Pentyl chloride; 2-methyl-2-butyl chloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.944 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C5H11Cl/c1-4-5(2,3)6/h4H2,1-3H3 Yes check.svgY
    Key: CRNIHJHMEQZAAS-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C5H11Cl/c1-4-5(2,3)6/h4H2,1-3H3
    Key: CRNIHJHMEQZAAS-UHFFFAOYAL
  • CCC(C)(Cl)C
Properties
C5H11Cl
Molar mass 106.59 g·mol−1
AppearanceColorless liquid
Odor unpleasant
Density 0.866 g/mL
Melting point −73 °C (−99 °F; 200 K)
Boiling point 85 to 86 °C (185 to 187 °F; 358 to 359 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

tert-Amyl chloride (2-methyl-2-butyl chloride) is an alkyl chloride used for flavoring and odorizing. [2] At room temperature, it is a colorless liquid with an unpleasant odor. It is an isomer of 1-chloropentane (n-amyl chloride).

Contents

Synthesis

tert-Amyl chloride can be synthesized from tert-amyl alcohol via an SN1 reaction with concentrated hydrochloric acid. [3]

See also

Related Research Articles

<span class="mw-page-title-main">Ether</span> Organic compounds made of alkyl/aryl groups bound to oxygen (R–O–R)

In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom bonded to two organyl groups. They have the general formula R−O−R′, where R and R′ represent the organyl groups. Ethers can again be classified into two varieties: if the organyl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether". Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.

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

Heptane or n-heptane is the straight-chain alkane with the chemical formula H3C(CH2)5CH3 or C7H16. When used as a test fuel component in anti-knock test engines, a 100% heptane fuel is the zero point of the octane rating scale (the 100 point is 100% iso-octane). Octane number equates to the anti-knock qualities of a comparison mixture of heptane and iso-octane which is expressed as the percentage of iso-octane in heptane, and is listed on pumps for gasoline (petrol) dispensed globally.

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.

<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">Tin(II) chloride</span> Chemical compound

Tin(II) chloride, also known as stannous chloride, is a white crystalline solid with the formula SnCl2. It forms a stable dihydrate, but aqueous solutions tend to undergo hydrolysis, particularly if hot. SnCl2 is widely used as a reducing agent (in acid solution), and in electrolytic baths for tin-plating. Tin(II) chloride should not be confused with the other chloride of tin; tin(IV) chloride or stannic chloride (SnCl4).

<span class="mw-page-title-main">Chiral auxiliary</span> Stereogenic group placed on a molecule to encourage stereoselectivity in reactions

In stereochemistry, a chiral auxiliary is a stereogenic group or unit that is temporarily incorporated into an organic compound in order to control the stereochemical outcome of the synthesis. The chirality present in the auxiliary can bias the stereoselectivity of one or more subsequent reactions. The auxiliary can then be typically recovered for future use.

Silyl ethers are a group of chemical compounds which contain a silicon atom covalently bonded to an alkoxy group. The general structure is R1R2R3Si−O−R4 where R4 is an alkyl group or an aryl group. Silyl ethers are usually used as protecting groups for alcohols in organic synthesis. Since R1R2R3 can be combinations of differing groups which can be varied in order to provide a number of silyl ethers, this group of chemical compounds provides a wide spectrum of selectivity for protecting group chemistry. Common silyl ethers are: trimethylsilyl (TMS), tert-butyldiphenylsilyl (TBDPS), tert-butyldimethylsilyl (TBS/TBDMS) and triisopropylsilyl (TIPS). They are particularly useful because they can be installed and removed very selectively under mild conditions.

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

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.

<span class="mw-page-title-main">Alkyl nitrite</span> Organic compounds of the form R–O–N=O

In organic chemistry, alkyl nitrites are a group of organic compounds based upon the molecular structure R−O−N=O, where R represents an alkyl group. Formally they are alkyl esters of nitrous acid. They are distinct from nitro compounds.

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

2-Naphthylamine is one of two isomeric aminonaphthalenes, compounds with the formula C10H7NH2. It is a colorless solid, but samples take on a reddish color in air because of oxidation. It was formerly used to make azo dyes, but it is a known carcinogen and has largely been replaced by less toxic compounds.

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.

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

tert-Amyl alcohol (TAA) or 2-methylbutan-2-ol (2M2B), is a branched pentanol.

tert-Amyl methyl ether (TAME) is an ether used as a fuel oxygenate. TAME derives from C5 distillation fractions of naphtha. It has an ethereous odor. Unlike most ethers, it does not require a stabilizer as it does not form peroxides on storage.

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

tert-Butylthiol, also known as tert-butyl mercaptan (TBM), and abbreciated t-BuSH, is an organosulfur compound with the formula (CH3)3CSH. This thiol has a strong odor. It is considered a flavoring agent.

<span class="mw-page-title-main">1-Chloropentane</span> Chemical compound

1-Chloropentane is an alkyl halide with the chemical formula CH3(CH2)4Cl. It is a colorless, flammable liquid. It can be prepared from 1-pentanol by treatment with hydrogen chloride.

The molecular formula C5H11Cl (molar mass: 106.59 g/mol, exact mass: 106.0549 u) may refer to:

<i>N</i>-<i>tert</i>-Butylbenzenesulfinimidoyl chloride Chemical compound

N-tert-Butylbenzenesulfinimidoyl chloride is a useful oxidant for organic synthesis reactions. It is a good electrophile, and the sulfimide S=N bond can be attacked by nucleophiles, such as alkoxides, enolates, and amide ions. The nitrogen atom in the resulting intermediate is basic, and can abstract an α-hydrogen to create a new double bond.

Amyl chloride may refer to any of the monochlorinated derivatives of the isomers of pentane. They have the molecular formula C5H11Cl.

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

Glybuzole is a hypoglycaemic medicine, mainly used to treat diabetes mellitus type 2. It is an oral antidiabetic drug (OAD), when administered in the right dose it will help bring the blood glycose level down by stimulating the insulin production. Similar medicines are glimepiride, glipizide, glibenclamide, gliclazide, and gliquidone.

<i>tert</i>-Butoxybis(dimethylamino)methane Chemical compound

tert-Butoxybis(dimethylamino)methane is an organic compound with the formula (CH3)3COCH(N(CH3)2)2. The compound is classified as an aminal ester, i.e. the tert-butyl alcohol derivative of the aminal bis(dimethylamino)methane. It is a colorless liquid with a amine odor.

References

  1. 2-Chloro-2-methylbutane at Sigma-Aldrich
  2. tert-Amyl chloride, degussa-bk.com
  3. Esselman, Brian J.; Hofstetter, Heike; Ellison, Aubrey J.; Fry, Charles G.; Hill, Nicholas J. (2020-08-11). "S N 1, E1, and E2 Reactions of tert -Amyl Compounds: Improved Analysis Using Computational Chemistry and ASAP-HSQC NMR Spectroscopy". Journal of Chemical Education. 97 (8): 2280–2285. doi:10.1021/acs.jchemed.0c00071. ISSN   0021-9584.