3-Methyl-3-pentanol

Last updated
3-Methyl-3-pentanol [1]
3-Methyl-3-pentanol.svg
3-Methyl-3-pentanol molecule ball.png
Names
Preferred IUPAC name
3-Methylpentan-3-ol
Other names
3-Methyl-3-pentanol
Diethyl carbinol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.959 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-053-4
PubChem CID
UNII
  • InChI=1S/C6H14O/c1-4-6(3,7)5-2/h7H,4-5H2,1-3H3 Yes check.svgY
    Key: FRDAATYAJDYRNW-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H14O/c1-4-6(3,7)5-2/h7H,4-5H2,1-3H3
    Key: FRDAATYAJDYRNW-UHFFFAOYAV
  • OC(C)(CC)CC
Properties
C6H14O
Molar mass 102.174 g/mol
Appearancecolorless liquid
Odor fruity
Density 0.8286 g/cm3 at 20 °C
Melting point −23.6 °C (−10.5 °F; 249.6 K)
Boiling point 122.4 °C (252.3 °F; 395.5 K)
45 g/L
Solubility miscible with ethanol, diethyl ether
Thermochemistry
293.4 J·mol−1·K−1 (liquid)
Hazards
Safety data sheet (SDS) http://www.sciencelab.com/msds.php?msdsId=9926087
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Warning
H226, H302
P210, P233, P240, P241, P242, P243, P264, P270, P280, P301+P312, P303+P361+P353, P330, P370+P378, P403+P235, P501
Lethal dose or concentration (LD, LC):
710 mg/kg rat
Related compounds
Related compounds
Hexanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

3-Methyl-3-pentanol (IUPAC name: 3-methylpentan-3-ol) is an organic chemical compound and a tertiary hexanol. It is used in the synthesis of the tranquilizer emylcamate, [2] and has similar sedative and anticonvulsant actions itself. [3]

Synthesis

It can be prepared by reacting ethylmagnesium bromide with methyl acetate in the so-called Grignard reaction using dried diethyl ether or tetrahydrofuran as solvent.

Synthesis of 3-Methyl-3-pentanol 3-Methyl-3-pentanol chemical equation.png
Synthesis of 3-Methyl-3-pentanol

It can be prepared also by reacting ethylmagnesium bromide with butanone in the same conditions already mentioned.

Related Research Articles

Bromine Chemical element, symbol Br and atomic number 35

Bromine is a chemical element with the symbol Br and atomic number 35. It is the third-lightest halogen, and is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between those of chlorine and iodine. Isolated independently by two chemists, Carl Jacob Löwig and Antoine Jérôme Balard, its name was derived from the Ancient Greek βρῶμος ("stench"), referring to its sharp and pungent smell.

Ether Class of organic compounds

Ethers are a class of organic compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula R–O–R′, where R and R′ represent the alkyl or aryl groups. Ethers can again be classified into two varieties: if the alkyl 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" (CH3–CH2–O–CH2–CH3). Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.

Haloalkane Group of chemical compounds derived from alkanes containing one or more halogens

The haloalkanes known as halogenoalkanes' or alkyl halides) are alkanes containing one or more halogen substituents. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially. They are used as flame retardants, fire extinguishants, refrigerants, propellants, solvents, and pharmaceuticals. Subsequent to the widespread use in commerce, many halocarbons have also been shown to be serious pollutants and toxins. For example, the chlorofluorocarbons have been shown to lead to ozone depletion. Methyl bromide is a controversial fumigant. Only haloalkanes that contain chlorine, bromine, and iodine are a threat to the ozone layer, but fluorinated volatile haloalkanes in theory may have activity as greenhouse gases. Methyl iodide, a naturally occurring substance, however, does not have ozone-depleting properties and the United States Environmental Protection Agency has designated the compound a non-ozone layer depleter. For more information, see Halomethane. Haloalkane or alkyl halides are the compounds which have the general formula "RX" where R is an alkyl or substituted alkyl group and X is a halogen.

S<sub>N</sub>2 reaction Substitution reaction where bonds are broken and formed simultaneously

The SN2 reaction is a type of reaction mechanism that is common in organic chemistry. In this mechanism, one bond is broken and one bond is formed synchronously, i.e., in one step. SN2 is a kind of nucleophilic substitution reaction mechanism, the name referring to the Hughes-Ingold symbol of the mechanism. Since two reacting species are involved in the slow (rate-determining) step, this leads to the term substitution nucleophilic (bi-molecular) or SN2; the other major kind is SN1. Many other more specialized mechanisms describe substitution reactions.

Potassium bromide Chemical compound

Potassium bromide is a salt, widely used as an anticonvulsant and a sedative in the late 19th and early 20th centuries, with over-the-counter use extending to 1975 in the US. Its action is due to the bromide ion. Potassium bromide is used as a veterinary drug, as an antiepileptic medication for dogs.

Sodium bromide Inorganic salt: NaBr

Sodium bromide is an inorganic compound with the formula NaBr. It is a high-melting white, crystalline solid that resembles sodium chloride. It is a widely used source of the bromide ion and has many applications.

2-Butanol Secondary alcohol

2-Butanol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. This secondary alcohol is a flammable, colorless liquid that is soluble in three parts water and completely miscible with organic solvents. It is produced on a large scale, primarily as a precursor to the industrial solvent methyl ethyl ketone. 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.

Hydrohalogenation

A hydrohalogenation reaction is the electrophilic addition of hydrohalic acids like hydrogen chloride or hydrogen bromide to alkenes to yield the corresponding haloalkanes.

Phosphorus tribromide Chemical compound

Phosphorus tribromide is a colourless liquid with the formula PBr3. The liquid fumes in moist air due to hydrolysis and has a penetrating odour. It is used in the laboratory for the conversion of alcohols to alkyl bromides.

The Corey–House synthesis (also called the Corey–Posner–Whitesides–House reaction and other permutations) is an organic reaction that involves the reaction of a lithium diorganylcuprate (R2CuLi) with an organyl (pseudo)halide (R'X) to form a new alkane, as well as an ill-defined organocopper species and lithium halide as byproducts.

Boron trichloride is the inorganic compound with the formula BCl3. This colorless gas is a reagent in organic synthesis. It is highly reactive toward water.

Grignard reagent Grignard reagents are extremely useful organometallic compounds in the field of organic chemistry

A Grignard reagent or Grignard Compound is a chemical compound with the generic formula R−Mg−X, where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride Cl−Mg−CH3 and phenylmagnesium bromide (C6H5)−Mg−Br. They are a subclass of the organomagnesium compounds.

Methyllithium Chemical compound

Methyllithium is the simplest organolithium reagent with the empirical formula CH3Li. This s-block organometallic compound adopts an oligomeric structure both in solution and in the solid state. This highly reactive compound, invariably used in solution with an ether as the solvent, is a reagent in organic synthesis as well as organometallic chemistry. Operations involving methyllithium require anhydrous conditions, because the compound is highly reactive toward water. Oxygen and carbon dioxide are also incompatible with MeLi. Methyllithium is usually not prepared, but purchased as a solution in various ethers.

Organocadmium compound

An organocadmium compound is an organometallic compound containing a carbon to cadmium chemical bond. Organocadmium chemistry describes physical properties, synthesis, reactions and use of these compounds. Cadmium shares group 12 with zinc and mercury and their corresponding chemistries have much in common.

Trimethylphosphine Chemical compound

Trimethylphosphine is the organophosphorus compound with the formula P(CH3)3, commonly abbreviated as PMe3. This colorless liquid has a strongly unpleasant odor, characteristic of alkylphosphines. The compound is a common ligand in coordination chemistry.

Organophosphines are organophosphorus compounds with the formula PRnH3−n, where R is an organic substituent. These compounds can be classified according to the value of n: primary phosphines (n = 1), secondary phosphines (n = 2), tertiary phosphines (n = 3). All adopt pyramidal structures. Organophosphines are generally colorless, lipophilic liquids or solids. The parent of the organophosphines is phosphine (PH3).

Magnesium bromide Chemical compound

Magnesium bromide (MgBr2) is a chemical compound of magnesium and bromine that is white and deliquescent. It is often used as a mild sedative and as an anticonvulsant for treatment of nervous disorders. It is water-soluble and somewhat soluble in alcohol. It can be found naturally in small amounts in some minerals such as: bischofite and carnallite, and in sea water, such as that of the Dead Sea.

The von Braun reaction is an organic reaction in which a tertiary amine reacts with cyanogen bromide to an organocyanamide. An example is the reaction of N,N-dimethyl-1-naphthylamine:

Ethylmagnesium bromide Chemical compound

Ethylmagnesium bromide is a Grignard reagent with formula C2H5MgBr. It is widely used in the laboratory synthesis of organic compounds.

Nitrogen tribromide is a chemical compound with the formula NBr3. It is extremely explosive in its pure form, even at −100 °C, and was not isolated until 1975. It is a deep-red and volatile solid.

References

  1. Lide DR (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, Florida: CRC Press. pp. 3–400, 5–47, 8–106. ISBN   0-8493-0594-2.
  2. Sittig M (1988). Pharmaceutical manufacturing encyclopedia. 2 (2 ed.). William Andrew. pp. 555–556. ISBN   978-0-8155-1144-1 . Retrieved 2010-01-22.
  3. Brown B, Schaffarzick RW, Dreisbach RH (October 1955). "Anticonvulsant properties of certain secondary and tertiary alcohols". The Journal of Pharmacology and Experimental Therapeutics. 115 (2): 230–9. PMID   13272171.