Phenylacetone

From Sciencemadness Wiki
Revision as of 15:37, 17 August 2022 by Mabus (Talk | contribs)

(diff) ← Older revision | Latest revision (diff) | Newer revision → (diff)
Jump to: navigation, search
Phenylacetone
Names
IUPAC name
1-Phenylpropan-2-one
Other names
Benzyl methyl ketone
Methyl benzyl ketone
P2P
Phenyl-2-propanone
Properties
C9H10O
C6H5CH2COCH3
Molar mass 134.178 g/mol
Appearance Colorless liquid
Odor Pleasant, floral-like
Density 1.0056 g/cm3 (20 °C)[1]
Melting point −15 °C (5 °F; 258 K)
Boiling point 214 °C (417 °F; 487 K)
0.227 g/100 ml (25 °C)
Solubility Miscible with alcohols, esters, ethers, halocarbons, ketones, toluene
Vapor pressure 0.16 mmHg (25 °C)
Thermochemistry
-152.399 kJ/mol[3]
Hazards
Safety data sheet Sigma-Aldrich
Flash point 90 °C (194 °F; 363 K)
Lethal dose or concentration (LD, LC):
2,501 mg/kg
Related compounds
Related compounds
Acetophenone
Benzylacetone
5-Phenylpentan-2-one
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Phenylacetone is an organic compound, an aromatic ketone with the formula C6H5CH2COCH3. It is used as precursor in organic chemistry for the synthesis of many aromatic compounds, but it's main infamous use is as precursor for amphetamine-class substances, although the P2P method has largely fallen out of favor due to P2P becoming a controlled substance, being replaced with the more accessible "Birch method" (pseudoephedrine reduction).

Properties

Chemical

Reduction of phenylacetone with a reducing agent, such as aluminium isopropoxide, will yield 1-phenyl-2-propanol.

C6H5CH2C(=O)CH3 → C6H5CH2CH(OH)CH3

Like with all methyl ketone compounds, addition of a basic solution containing iodine will yield iodoform.

C6H5CH2COCH3 + 2 OH- + 2 I2 → C6H5CH2COO- + I- + CHI3 + H2O

Physical

Phenylacetone is a colorless liquid, albeit impure samples tend to appear yellowish, immiscible with water, but miscible with organic solvents. It has a pleasant odor, described by different people as: "honey-like", "burnt flowers", "green apple", etc.

Availability

Phenylacetone is sold by chemical suppliers, but due to its legal status as drug precursor (used in the production amphetamine-class drugs), it cannot be purchased by the home chemist without a hard to acquire permit. Since it's classified as List I drug precursor in most countries, it's almost impossible to be acquired by the hobby chemist. In the United States it is classified as a DEA List I chemical.

Preparation

There are hundreds of synthesis routes described in literature. A list containing several routes can be found on Erowid.

Projects

  • Make 1-phenyl-2-propanol
  • Precursor for fragrances

Handling

Safety

Phenylacetone has low toxicity, though it may be irritant.

Storage

In closed, airtight bottles, away from air and light.

Disposal

Can be destroyed with excess bleach (to destroy leftover chloroform), then poured down the drain.

References

  1. Kuroyan, R. A.; Markosyan, A. I.; Engoyan, A. P.; Vartanyan, S. A.; Journal of Organic Chemistry USSR (English Translation); vol. 19; (1983); p. 1709 - 1714; Zhurnal Organicheskoi Khimii; vol. 19; nb. 9; (1983); p. 1947 - 1953,
  2. Li, Sha; Wang, Ning; Hong, Ming; Tan, Hor-Yue; Pan, Guofeng; Feng, Yibin; Molecules; vol. 23; nb. 2; (2018); Art.No: 352
  3. Nicholson et al.; Journal of the Chemical Society; (1954); p. 2767
  4. Parks et al.; Journal of Chemical Physics; vol. 22; (1954); p. 2089

Relevant Sciencemadness threads