3-Chlorperbenzoesure Chemische Eigenschaften,Einsatz,Produktion Methoden
R-S?tze Betriebsanweisung:
R5:Beim Erw?rmen explosionsf?hig.
R8:Feuergefahr bei Berührung mit brennbaren Stoffen.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R43:Sensibilisierung durch Hautkontakt m?glich.
R7:Kann Brand verursachen.
R34:Verursacht Ver?tzungen.
R22:Gesundheitssch?dlich beim Verschlucken.
S-S?tze Betriebsanweisung:
S17:Von brennbaren Stoffen fernhalten.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn m?glich, dieses Etikett vorzeigen).
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S3/7:Beh?lter dicht geschlossen halten und an einem kühlen Ort aufbewahren.
S14:Von . . . fernhalten (inkompatible Substanzen sind vom Hersteller anzugeben).
S27:Beschmutzte, getr?nkte Kleidung sofort ausziehen.
S7/9:Beh?lter dicht geschlossen an einem gut gelüfteten Ort aufbewahren.
Chemische Eigenschaften
White moist powder
Verwenden
3-Chloroperoxybenzoic acid is a strong oxidizing agent used in the oxidation reactions such as aldehydes and ketones to esters (Bayer-Villiger-Oxidation), olefines to epoxides, sulfides to sulfoxides and sulfones, and amines to nitroalkanes, N-oxides.
Reaktionen
3-Chloroperoxybenzoic acid (MCPBA) is one of the most popular oxidation reagent in organic synthesis, because of its outstanding performance in terms of:
reactivity, combined with reducing the number of reaction steps in classical synthetic routes,
regio- and stereoselectivity,
protection of functional groups mostly not required,
high purity and yields.
Its literature covers a huge area of different syntheses and below reaction equations just can be a brief overview of its interesting applications:
Allgemeine Beschreibung
3-Chloroperoxybenzoic acid is sensitive to heat. Storage of 3-Chloroperoxybenzoic acid must be done so with stringent temperature control measures. It's explosion hazard is also mitigated by mixing the peroxide in a solvent slurry.
Reaktivit?t anzeigen
May explode from heat, shock, friction or contamination. May ignite combustibles (wood, paper, oil, clothing, etc.). May be ignited by heat, sparks or flames.
l?uterung methode
Recrystallise MCPBA from CH2Cl2 [Traylor & Mikztal J Am Chem Soc 109 2770 1987]. Peracid of 99+% purity can be obtained by washing commercial 85% material with phosphate buffer pH 7.5 and drying the residue under reduced pressure. Alternatively the peracid can be freed from m-chlorobenzoic acid by dissolving 50g/L of *benzene and washing with an aqueous solution buffered at pH 7.4 (NaH2PO4/NaOH) (5 x 100mL). The organic layer is dried over MgSO4 and carefully evaporated under vacuum. Necessary care should be taken in case of EXPLOSION. The solid is recrystallised twice from CH2Cl2/Et2O and stored at 0o in a plastic container as glass catalyses the decomposition of the peracid. The acid is assayed iodometrically. [Schwartz & Blumbrgs J Org Chem 29 1976 1964, Bortolini et al. J Org Chem 52 5093 1987, McDonald et al. Org Synth Coll Vol VI 276 1988, Beilstein 9 IV 972.]
3-Chlorperbenzoesure Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
5-Bromo-2-hydroxymethylpyridine
3-(TERT-BUTOXYCARBONYLAMINO-METHYL)-PYRIDINE-2-CARBOXYLIC ACID
6-BROMO-1H-PYRROLO[2,3-B]PYRIDINE
5-BROMO-2-METHYLPYRIDINE N-OXIDE
LORACARBEF (200 MG)
4-IODO-7-AZAINDOLE
1,2-Epoxyhexan
4-(CHLOROSULFONYL)-7-FLUORO-2,1,3-BENZOXADIAZOLE
1,4-Dihydro-3H-2-benzopyran-3-on
4-(METHYLSULFINYL)PHENOL
3,5-DIMETHYLPYRIDIN-4-AMINE
8-HYDROXYQUINOLINE-2-CARBONITRILE
4,5-DICHLORO-2-METHYLPYRIDINE
1H-Pyrrolo[2,3-b]pyridine, 4-nitro-, 7-oxide
3-AMINOMETHYL-PYRIDINE-2-CARBOXYLIC ACID
4-[(TERT-BUTOXYCARBONYLAMINO)METHYL]-2-CYANOPYRIDINE
4-Bromo-7-azaindole
Tacalcitol
Nitrocyclohexan
4-Chloro-7-azaindole
7-OXIDE-7-AZAINDOLE
4-(BOC-AMINOMETHYL)PYRIDINE-2-CARBOXYLIC ACID
4-Chloro-2-(methylsulfonyl)pyrimidine
5-BROMO-4-CHLORO-2-METHANESULFONYL-PYRIMIDINE
4-FLUORO-2,1,3-BENZOXADIAZOLE
2-(2,3-DIHYDRO-1-BENZENESULFONYL-PYRROLO[2,3-B]PYRIDIN-3-YL)ACETONITRILE
METHYL(2R,3S)-2,2-DIMETHYL-3-(2-OXOPROPYL)-CYCLOPROPANEACETATE
1,7-DIDEAZAADENINE
Pantoprazole
Omeprazole
1,2-Epoxycyclopentan
3-NITROSOBENZAMIDE
5-Bromopyridine-2-carbaldehyde
6-CHLORO-1H-PYRROLO[2,3-B]PYRIDINE
1,4-OXATHIANE SULFOXIMINE
1H-PYRROLO[2,3-B]PYRIDINE, 4-NITRO-
2,5-Dichlorpyridin
S-METHYL-S-(2-METHYLPYRAZINYL) SULFOXIMINE
1,2-EPOXY-9-DECENE
1-PROPANESULPHONYLACETONITRILE