Thian

Structural formula
General
Surname	Thian
other names	Tetrahydrothiopyran Thiacyclohexane Pentamethylene sulfide
Molecular formula	C 5 H 10 S
External identifiers / databases
CAS number 1613-51-0 EC number 216-561-1 ECHA InfoCard 100.015.056 PubChem 15367 ChemSpider 14628 Wikidata Q413411
properties
Molar mass	102.19 g mol −1
Physical state	liquid to solid connection
density	0.99 g cm −3 (20 ° C)
Melting point	19 ° C
boiling point	140-142 ° C
Vapor pressure	116.5 h Pa (75 ° C)
Refractive index	1.5067 (20 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 225 P: 210
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

Thiane , also called tetrahydrothiopyran , is the simplest sulfur-containing saturated six-membered heterocycle .

presentation

Thiane can be obtained in good yield by the reaction of 1,5-dibromopentane with sodium sulfide .

${\displaystyle \mathrm {Br{-}(CH_{2})_{5}{-}Br+Na_{2}S\longrightarrow } }$ ${\displaystyle \mathrm {C_{5}H_{10}S+2\ NaBr} }$

Reaction of 1,5-dibromopentane with sodium sulfide to give thiane and sodium bromide .

Another possibility is the cyclization of 5-bromo-1-pentanethiol in the presence of a base .

${\displaystyle \mathrm {Br{-}(CH_{2})_{5}{-}SH+NaH\longrightarrow } }$ ${\displaystyle \mathrm {C_{5}H_{10}S+NaBr+H_{2}\ } }$

Reaction of 5-bromo-1-thiol with sodium hydride to form thiane, sodium bromide and hydrogen .

It can also be produced by reacting 1,5-dichloropentane with sodium sulfide .

properties

Thian crystallizes in the cubic crystal system with the lattice parameter a  = 869  pm and four formula units per unit cell .

Reactions

Thiane can react as a nucleophile , but only with good leaving groups . Organohalides can be activated with silver salts. So-called tetrahydrothiopyranium salts are formed here .

Reaction of thiane with bromoacetic acid

swell

1. ↑ GH Jeffery, R. Parker, AI Vogel in: J. Chem. Soc. 1961 , 570-574.
2. ↑ D. Vedal, OH Ellestad, P. Klaboe, G. Hagen in: Spectrochim. Acta Part A 1975 , 31 , 355-372.
3. ↑ RL Crumbie, DD Ridley in: Aust. J. Chem. 1979 , 32 , 2777-2781.
4. ^ PT White, DG Barnard – Smith, FA Fidler in: Ind. Eng. Chem. 1952 , 44 , 1430-1438.
5. ↑ 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. 3-482.
6. ↑ ^{a b} Datasheet Pentamethylene sulfide from Sigma-Aldrich , accessed on April 24, 2011 ( PDF ).
7. ↑ K. Nagasawa, A. Yoneta: Chemistry. II. Use of Dimethyl Sulfoxide - a Facile Synthesis of Cyclic Sulfides in Chem. Pharm. Bull. 1985 , 33 , 5048-5052, doi: 10.1248 / cpb.33.5048 , pdf .
8. ^ MB Anderson, MG Ranasinghe, JT Palmer, PL Fuchs: Cytochalasin support studies. 10. Nucleophilic and electrophilic mercaptanylations via 2- (trimethylsilyl) ethanethiol-derived reagents in: J. Org. Chem. 1988 , 53 , 3125-3127, doi : 10.1021 / jo00248a045 .
9. ↑ Data sheet 1,5-dichloropentane, 98% from AlfaAesar, accessed on October 29, 2018 ( PDF )(JavaScript required) .
10. ↑ S. Kondo in: Bull. Chem. Soc. Jpn. 1956 , 29 , 999.
11. ^ E. Ziegler, H. Wittmann, H. Sterk in: Monatsh. Chem. 1987 , 118 , 115-126.