2-isopropyl naphthalene

Structural formula
General
Surname	2-isopropyl naphthalene
other names	2- (1-methylethyl) naphthalene
Molecular formula	C 13 H 14
Brief description	yellow liquid
External identifiers / databases
CAS number 2027-17-0 EC number 217-976-0 ECHA InfoCard 100.016.343 PubChem 16238 ChemSpider 15410 Wikidata Q27259457
properties
Molar mass	170.255 g mol −1
Physical state	liquid
density	0.975 g cm −3
Melting point	14 ° C
boiling point	268 ° C
solubility	2.81 mg l −1 in water (25 ° C, mixture of 1-isopropylnaphthalene and 2-isopropylnaphthalene) soluble in diethyl ether , ethanol and benzene
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
Toxicological data	5300 mg kg −1 ( LD 50 ,  mouse ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2-Isopropylnaphthalene is a naphthalene substituted in the β-position . The systematic name is 2- (1-methylethyl) naphthalene.

Occurrence

2-Isopropylnaphthalene is part of the complex mixture of substances called crude oil .

Extraction and presentation

2-Isopropylnaphthalene can be prepared in the laboratory, for example, by Friedel-Crafts alkylation of naphthalene with propene .

Biological importance

It is broken down in the atmosphere by photolysis or by reaction with hydroxyl radicals present .

safety instructions

It was found in laboratory mice that isopropylnaphthalenes and their photoproducts are lung toxins. Isopropylnaphthalenes, more precisely the mixture of 1-isopropylnaphthalene and 2-isopropylnaphthalene, are on the CoRAP list due to the suspicion of PBT / vPvB , their environmental exposure and their widespread use .

Individual evidence

1. ^ RJ Lewis, Sr (Ed.): Hawley's Condensed Chemical Dictionary. 13th edition. John Wiley & Sons, New York 1997, p. 634.
2. ↑ ^{a b c d e} data sheet 2-Isopropylnaphthalene, 96% from AlfaAesar, accessed on June 14, 2017 ( PDF )(JavaScript required) .
3. ↑ Registration dossier on isopropylnaphthalenes (section Water solubility ) at the European Chemicals Agency (ECHA), accessed on December 11, 2018.
4. ↑ DR Lide, GWA Milne (Ed.): Handbook of Data on Organic Compounds. Volume I, 3rd edition. CRC Press, Boca Raton, FL. 1994, p. V4 3553.
5. ^ RJ Lewis: Sax's Dangerous Properties of Industrial Materials. 9th edition. Volumes 1-3. Van Nostrand Reinhold, New York 1996, p. 1990.
6. ^ RE Kirk, DF Othmer: Encyclopedia of Chemical Technology. 4th edition. Volumes 1, John Wiley and Sons, New York 1991, pp. V16 967.
7. ↑ Terry F. Bidleman: Atmospheric processes. In: Environmental Science & Technology . 22 (4), 1988, pp. 361-367. doi: 10.1021 / es00169a002 .
8. ↑ BJ Zwolinksi, RC Wilhoit: Handbook of vapor pressures and heats of vaporizaton of hydrocarbons and related compounds. (= API44-TRC101 ). Thermodynamics Research Center, College Station, TX 1971, pp. 227-228.
9. ^ William M. Meylan, Philip H. Howard: Computer estimation of the Atmospheric gas-phase reaction rate of organic compounds with hydroxyl radicals and ozone. In: Chemosphere . 26 (12), 1993, pp. 2293-2299. doi: 10.1016 / 0045-6535 (93) 90355-9 .
10. ↑ Koichi Fukuda, Yasushi Inagaki, Toshiro Maruyama, Harumi Imamura Kojima, Tamao Yoshida: On the photolysis of alkylated naphthalenes in aquatic systems. In: Chemosphere. 17 (4), 1988, pp. 651-659. doi: 10.1016 / 0045-6535 (88) 90245-7 .
11. ↑ T. Honda, M. Kiyozumi, S. Kojima: Alkylnaphthalene. XI. Pulmonary toxicity of naphthalene, 2-methylnaphthalene, and isopropylnaphthalenes in mice. In: Chem Pharm Bull . (Tokyo). 38 (11), 1990, pp. 3130-3135. PMID 2085898 .
12. ↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): Isopropylnaphthalene , accessed on December 11, 2018.