2-dietilaminoetanotiol - 2-dietilaminoetanotiol

2-dietilaminoetanotiol
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IUPAC name
2- (dietilamino) etanotiol
General
Other names 2-dietilaminoetil-mercaptano Dietilcisteamina
DEAET
Semi-developed formula (CH3-CH2)2N-CH2-CH2-SH
Molecular formula C6H15NS
Identifiers
CAS number 100-38-9[1]
ChemSpider 15224
PubChem 16032
Physical properties
Appearance Liquid oily colorless to orange.
Density 900 kg/; 0,9 g/cm³
Molar mass 133.26 g / mol
Melting point −29 °C (244 K)
Boiling point 162 °C (435 K)
Vapor pressure 2,3 ± 0,3 mmHg
Refractive index (n D ) 1,469
Chemical properties
Solubility in water 5 g/L
log P 1,82
Family Amine , thiol
Dangerousness
Flash point 325,15 K (52 °C)
Related compounds
amines Triethylamine
2- (methylthio) ethylamine
aminotioles Cisteamina
Captamina 2- (etilamino) etanotiol
Values ​​in the SI and under standard conditions
(25 and 1 atm ), unless otherwise indicated.

The 2-diethylaminoethanethiol , also known as dietilcisteamina , [ 2 ] is an organic compound of molecular formula C 6 H 15 N S . It is an aminothiol with a single tertiary amino group . Its structure is related to that of cysteamine , but unlike the latter, the two hydrogens attached to the nitrogen are replaced by two ethyl groups . It is also similar to that of triethylamine , with a thiol group (-SH) added at one end.

Physical and chemical properties

2-Diethylaminoethanethiol is an oily liquid with a colorless to orange hue. [ 3 ] It reaches the boiling point at 162 ° C , while its melting point is -29 ° C, both of which are estimated values. Its flash point - the minimum temperature at which the vapors of a fluid initiate combustion - is 52 ± 23 ° C. [ 4 ]

It has a density of 0.9 g / L . It is somewhat soluble in water, in an approximate proportion of 5 g / L. The value of the logarithm of its partition coefficient , log P = 1.82, indicates that its solubility in hydrophobic solvents is considerably higher than in hydrophilic solvents . Its estimated surface tension is 30 dyne / cm, [ 4 ] less than half that of water.

Synthesis and uses

2-Diethylaminoethanethiol can be synthesized by reacting S- [2- (diethylamino) ethyl] benzenecarbothioate with hydrogen chloride . It is also obtained from S- (2-chloroethyl) ethanethioate, ethyl ether and diethylamine . [ 5 ]

In terms of uses, this aminothiol is an intermediate in the synthesis of S-pregabalin (P704790), [ 3 ] enantiomer of pregabalin used as anticonvulsant and analgesic anxiolytic . [ 6 ] On the other hand, 2-diethylaminoethanethiol is an intermediate product or appears as an impurity in the manufacture of chemical weapons . [ 2 ] In this sense, it is one of the degradation products of type V nerve gases , having developed methods for its detection both in running water and in river waters. [ 7][8]

Precautions

This compound is irritating to the eyes, skin and respiratory system. [ 3 ]

See also

The following aminothiols are isomers of 2-diethylaminoethanethiol:

The following compounds are thioethers also isomers of 2-diethylaminoethanethiol:

References

  1. CAS number
  2. a b 2-(Diethylamino)ethanethiol (PubChem)
  3. a b c 2-Diethylaminoethanethiol(100-38-9) (Chemical Book)
  4. a b 2-Diethylaminoethanethiol (ChemSpider)
  5. 2-(diethylamino)ethanethiol 100-38-9 Synthesis Route (Molbase)
  6. P704790 (Toronto Research Chemicals)
  7. Wang J, Zima J, Lawrence NS, Chatrathi MP, Mulchandani A, Collins GE (2004). «Microchip capillary electrophoresis with electrochemical detection of thiol-containing degradation products of V-type nerve agents.». Analytical chemistry 76 (16): 4721-4726. Consultado el 5 de junio de 2016.
  8. Joshi KA1, Prouza M, Kum M, Wang J, Tang J, Haddon R, Chen W, Mulchandani A. (2006). «V-type nerve agent detection using a carbon nanotube-based amperometric enzyme electrode.». Analytical chemistry 78 (1): 4721-4726. Consultado el 5 de junio de 2016.