Oxepan

Structural formula
General
Surname	Oxepan
other names	Hexamethylene oxide Oxacycloheptane
Molecular formula	C 6 H 12 O
Brief description	clear, slightly yellowish liquid
External identifiers / databases
CAS number 592-90-5 EC number 209-777-2 ECHA InfoCard 100,008,890 PubChem 11618 Wikidata Q253118
properties
Molar mass	100.16 g mol −1
Physical state	liquid
density	0.90 g cm −3
boiling point	124-126 ° C
Refractive index	1.4400 (20 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 225 P: 210-233-241-242-243-280-303 + 361 + 353-403 + 235-501
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Oxepan is a chemical compound from the group of saturated heterocycles . It is the simplest seven - membered oxygen - containing heteroaliphatic.

presentation

Oxepane can be prepared from the cyclization of 1,6-hexanediol in DMSO at 190 ° C., but only in poor yield. Another possibility, which, however, gives a comparably poor yield, is the cyclization of 1,6-dichlorohexane with potassium hydroxide .

Reactions

Oxepanes can be used to prepare α, ω-functionalized derivatives of hexane by ring opening . Lewis or Brønsted acids can be used to open the ring . The reaction of Oxepan with phenyl dichlorophosphate and sodium iodide produces 1,6-diiodohexane.

6-Bromohexanal is accessible from the reaction with boron tribromide with subsequent oxidation by PCC .

Individual evidence

1. ↑ ^{a b c} Entry on Hexamethylene Oxide at TCI Europe, accessed on October 31, 2016.
2. ↑ A. Müller, W. Vanc, in: Monatsh. Chem. , 1947 , 77 , pp. 259-263.
3. ↑ A. Misono, T. Osa, Y. Sanami, in: Bull. Chem. Soc. Jpn. , 1968 , 41 , pp. 2447-2453.
4. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-408.
5. ↑ VJ Traynelis, WL Hergenrother, HT Hanson, JA Valicenti, in: J. Org. Chem. , 1964 , 29 , pp. 123-129.
6. ↑ HA Zahalka, Y. Sasson, in: Synthesis , 1986 , 9 , pp. 763-765.
7. ↑ H.-J. Liu, LM Shewchuk, M. Llinas-Brunet, in: Heterocycles , 1986 , 24 , pp. 3043-3046.
8. ↑ SU Kulkarni, U. Surendra, VD Patil, in: Heterocycles , 1982 , 18 , pp. 163-167.