Anisidines
| Anisidines | |||||||||||
| Surname | 2-anisidine | 3-anisidine | 4-anisidine | ||||||||
| other names |
o -anisidine, 2-methoxyaniline, o -aminoanisole |
m -anisidine, 3-methoxyaniline, m -aminoanisole |
p -anisidine, 4-methoxyaniline, p -aminoanisole |
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| Structural formula |
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| CAS number | 90-04-0 | 536-90-3 | 104-94-9 | ||||||||
| PubChem | 7000 | 10824 | 7732 | ||||||||
| Molecular formula | C 7 H 9 NO | ||||||||||
| Molar mass | 123.15 g mol −1 | ||||||||||
| Physical state | liquid | firmly | |||||||||
| Brief description | yellowish liquid |
yellowish liquid with an aromatic odor |
colorless to gray-brown mass with a weak aniline odor |
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| Melting point | 5 ° C | −1 ° C | 57 ° C | ||||||||
| boiling point | 225 ° C | 251 ° C | 243 ° C | ||||||||
|
pK s value (of the conjugate acid BH + ) |
4.52 | 4.20 | 5.31 | ||||||||
| density | 1.09 g cm −3 | 1.10 g cm −3 | 1.08 g cm −3 | ||||||||
| Vapor pressure | 0.05 mbar (20 ° C) | 0.0035 mbar (20 ° C) | 0.02 mbar (20 ° C) | ||||||||
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Solubility in water |
15.0 g l −1 (25 ° C) | poorly soluble | 22 g l −1 (20 ° C) | ||||||||
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GHS labeling |
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| H and P phrases | 350-331-311-301-341 | 301-311-331-373-411 | 330-310-300-373-400 | ||||||||
| no EUH phrases | no EUH phrases | no EUH phrases | |||||||||
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201-280-302 + 352 304 + 340-309 + 310 |
260-273-280-301 + 310 302 + 350-304 + 340 |
201-260-264 273-280-284 |
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The anisidines (also methoxyanilines or aminoanisoles ) form a group of substances in chemistry that is derived from both anisole (methoxybenzene) and aniline . The structure consists of a benzene ring with attached methoxy (–OCH 3 ) and amino (–NH 2 ) groups as substituents . Their different arrangement ( ortho , meta or para ) results in three constitutional isomers with the empirical formula C 7 H 9 NO. First and foremost, they can be viewed as methoxy-substituted anilines.
The nitrated or halogenated derivatives are also referred to as anisidines. If they contain an additional methyl group , they form the group of cresidins . Just as the anise idine from ordinary registered anise oil or Phenet idine of Phenet ol derived, was carried out in a manner analogous to the naming for Kres idine from Kres ol (nitrogen-containing derivatives of cresols).
properties
The Anisidines have (4.603) only slightly different pK opposite the aniline s values. They differ more clearly in their melting points. Due to its symmetry, 4-anisidine has the highest melting point and is a solid.
use
Anisidines are intermediates in the manufacture of azo dyes and pharmaceuticals. The anisidines are used as starting substances for the preparation of the chlorine , bromine and iodine anisoles by means of the Sandmeyer reaction . After reductive cleavage of azo groups, ortho-ansidin must not be released from textiles or leather products that come into direct contact with human skin for a long period of time (Appendix 1 of the Consumer Goods Ordinance ).
The methoxyphenols can be prepared by boiling the diazonium salts .
It is also a component of a detection reagent in thin-layer chromatography of monosaccharides .
Derivatives
Individual evidence
- ↑ a b c Entry on 2-anisidine in the GESTIS substance database of the IFA , accessed on November 17, 2014(JavaScript required) .
- ↑ a b c Entry on 3-anisidine in the GESTIS substance database of the IFA , accessed on November 17, 2014(JavaScript required) .
- ↑ a b c Entry on 4-anisidine in the GESTIS substance database of the IFA , accessed on November 17, 2014(JavaScript required) .
- ↑ a b CRC Handbook of Tables for Organic Compound Identification , Third Edition, 1984, ISBN 0-8493-0303-6 .
- ↑ Reinhard Mattisek, Gabriele Steiner, Markus Fischer: Food Analysis . 4th edition. Springer, Berlin 2010, ISBN 978-3-540-92205-6 .
