Phenetidine

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Phenetidine
Surname 2-phenetidine 3-phenetidine 4-phenetidine
other names o -phenetidine,
2-ethoxyaniline,
o -aminophenetol 		m -phenetidine,
3-ethoxyaniline,
m -aminophenetol 		p -phenetidine,
4-ethoxyaniline,
p -aminophenetol
Structural formula O-Phenetidine.svg M-Phenetidine.svg P-Phenetidine.svg
CAS number 94-70-2 621-33-0 156-43-4
PubChem 7203 12120 9076
ECHA InfoCard 100.002.143 100.009.711 100.005.324
Molecular formula C 8 H 11 NO
Molar mass 137.18 g mol −1
Physical state liquid
Brief description colorless to
brown liquid
with an aromatic odor 		yellowish
near odorless liquid
  		colorless to
yellowish liquid
with a characteristic odor
Melting point −4 ° C - 3 ° C
boiling point 232-234 ° C 248 ° C 254 ° C
pK s value
(of the conjugate
acid BH + ) 		4.43 4.17 5.20
solubility 7 g l −1 (20 ° C) poorly soluble 20 g l −1 (20 ° C)
GHS
labeling
06 - Toxic or very toxic 08 - Dangerous to health
danger
06 - Toxic or very toxic 08 - Dangerous to health
danger
08 - Dangerous to health 07 - Warning
Caution
H and P phrases 301-311-331-373 301 + 311 + 331-373 341-302 + 312-331-317-319-412
no EUH phrases no EUH phrases no EUH phrases
280-302 + 352
304 + 340-309 + 310 		280-261-301 + 310-311 280-260-301 + 310-314-501

The phenetidines (also ethoxyanilines or aminophenetols ) form a group of substances that are derived from both phenetol (ethoxybenzene) and aniline . The structure consists of a benzene ring with attached ethoxy  (–OCH 2 CH 3 ) and amino groups  (–NH 2 ) as substituents . Their different arrangement results in three constitutional isomers with the empirical formula C 8 H 11 NO. Primarily they can be viewed as ethoxy substituted anilines.

Just as the anis idines are derived from the root anis ol , the naming of the ethoxy derivatives as phenet idines proceeding from phenet ol in an analogous manner .

properties

The phenetidines have (4.603) only slightly different pK opposite the aniline s values.

Extraction and presentation

2- and 4-phenetidine are produced from phenetol by nitration (to 2- or 4-nitrophenetol ) and subsequent hydrogenation .

Individual evidence

  1. ↑ a b c d Entry on 2-phenetidine in the GESTIS substance database of the IFA , accessed on December 26, 2019(JavaScript required) .
  2. ↑ a b c d Entry on 3-phenetidine in the GESTIS substance database of the IFA , accessed on December 26, 2019(JavaScript required) .
  3. ↑ a b c d Entry on 4-phenetidine in the GESTIS substance database of the IFA , accessed on December 26, 2019(JavaScript required) .
  4. ↑ a b CRC Handbook of Tables for Organic Compound Identification , Third Edition, 1984, ISBN 0-8493-0303-6 .
  5. ↑ Entry on Phenetidine. In: Römpp Online . Georg Thieme Verlag, accessed on December 17, 2014.