4- (dimethylamino) pyridine
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| General | |||||||||||||||||||
| Surname | 4- (dimethylamino) pyridine | ||||||||||||||||||
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| Molecular formula | C 7 H 10 N 2 | ||||||||||||||||||
| Brief description |
unpleasant and slightly amine-like smelling, beige powder |
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| properties | |||||||||||||||||||
| Molar mass | 122.17 g mol −1 | ||||||||||||||||||
| Physical state |
firmly |
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| Melting point |
110-112 ° C |
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| boiling point |
138–140 ° C (24 h Pa ) |
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| solubility |
moderately soluble in water: 60 g l −1 (20 ° C), 76 g l −1 (25 ° C), slightly soluble in methanol |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
4- (Dimethylamino) pyridine (abbr .: DMAP or 4-DMAP, EC number : 214-353-5) is a substituted pyridine .
properties
4- (Dimethylamino) pyridine is an unpleasant and slightly amine- like smelling solid at room temperature . If 60 grams of 4- (dimethylamino) pyridine are dissolved in 1 liter of water at 20 ° C, the pH value of this solution is around 11. The flash point is 124 ° C and the ignition temperature is 420 ° C. The bulk density of 4- (dimethylamino) pyridine is 520 kg · m −3 .
use
4- (Dimethylamino) pyridine is used as a nucleophilic catalyst in organic chemistry . 4- (Dimethylamino) pyridine is often used as a catalyst for the esterification of sterically demanding secondary and tertiary alcohols with carboxylic acid anhydrides under mild conditions (Steglich catalyst).
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DMAP is also used for the phase transfer of nanoparticles from toluene to water. On its surface, it forms a monolayer that is positively charged towards the outside , which prevents the nanoparticles from clumping together through the repulsive forces. The pyridine layer can later be replaced relatively easily by other functional groups.
safety instructions
Inhalation of the dusts of this chemical can cause irritation of the respiratory tract, drowsiness, nausea, drowsiness and headache. If the chemical is inhaled, it can cause edema in the body's respiratory tract . After contact with skin and eyes irritation occurs, after swallowing diarrhea, nausea and vomiting occur. Accordingly, one should not inhale the dust of 4- (dimethylamino) pyridine, wear suitable protective gloves (e.g. made of nitrile rubber ) and protective clothing when working with the substance . 4- (Dimethylamino) -pyridine is highly hazardous to water and therefore has WGK 3. Accordingly, the substance should not be allowed to get into bodies of water, sewage or soil.
The material may only be stored in an accessible place for specialists.
Individual evidence
- ↑ a b c d e f g h i j Data sheet 4- (dimethylamino) -pyridine (PDF) from Merck , accessed on March 18, 2011.
- ↑ Data sheet 4- (dimethylamino) -pyridine from Acros, accessed on March 25, 2007.
- ^ David I. Gittins, Frank Caruso: Spontaneous Phase Transfer of Nanoparticulate Metals from Organic to Aqueous Media. In: Angewandte Chemie International Edition. 40, 2001, pp. 3001-3004, doi : 10.1002 / 1521-3773 (20010817) 40:16 <3001 :: AID-ANIE3001> 3.0.CO; 2-5 .
literature
- Alan C. Spivey, Stellios Arseniyadis: Nucleophilic catalysis by 4- (dialkylamino) pyridines rewound: Optimization of reactivity and selectivity. In: Angew. Chem. 116. 2004, 5552-5557: doi : 10.1002 / anie.200460373 .
- B. Neises, W. Steglich: Simple Method for the Esterification of Carboxylic Acids. In: Angew. Chem. Int. Ed. 17. 1978, 522-524. doi : 10.1002 / anie.197805691 .