Bis(trichlormethyl)carbonat Chemische Eigenschaften,Einsatz,Produktion Methoden
R-Sätze Betriebsanweisung:
R26:Sehr giftig beim Einatmen.
R34:Verursacht Verätzungen.
R29:Entwickelt bei Berührung mit Wasser giftige Gase.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S9:Behälter an einem gut gelüfteten Ort aufbewahren.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S7/9:Behälter dicht geschlossen an einem gut gelüfteten Ort aufbewahren.
Beschreibung
Triphosgene is also known as solid phosgene. Its chemical name is bis (Trichloromethyl) carbonate, and its English name is bisgriehloromethyl) carbonate or triphosgene, abbreviated as BTC. Triphosgene is a white crystal, similar to the smell of phosgene. It is mainly used to synthesize chloroformate, isocyanate, polycarbonate and acyl chloride. It is widely used as an intermediate in plastics, medicine, herbicides and pesticides.
Chemische Eigenschaften
White solid
Verwenden
Triphosgene is used as a carbonylating agent for aza-peptide synthesis. It reacts with several alfa-amino acids to give the corresponding N-carboxyanhydrides. It is involved in the preparation of the esterification coupling reagent, di-2-thienyl carbonate from 2(5H)-thiophenone. Further, it is used as a reagent in organic synthesis and converts an amino group into isocyanate. In addition to this, it is employed in the preparation of 2-chloronicotinaldehydes through cyclization of the corresponding enamides. It is considered as a useful substitute for phosgene.
Allgemeine Beschreibung
Triphosgene [Bis(trichloromethyl)carbonate] is a versatile organic reagent used in organic synthesis alternative to phosgene. A catalytic amount of triphosgene is particularly used in chloroformylations, carbonylations, chlorinations, and dehydration reactions.
Synthese
Triphosgene is synthesized by exhaustive free radical chlorination of dimethyl carbonate:
CH
3OCO
2CH
3 + 6 Cl
2 → CCl
3OCO
2CCl
3 + 6 HCl
Triphosgene can be easily recrystallized from hot hexanes.
läuterung methode
It is a good solid substitute for phosgene (using a third mol per mol). Crystallise it from pet ether (b 60-80o), wash it with anhydrous cold Et2O, de-gas it at 200mm then dry at 0.1mm (over H2SO4). It has IR: max 900 and 1900 cm-1 . It is a lachrymator, is TOXIC and should be handled with gloves and in an efficient fume hood. [Hales et al. J Chem Soc 620 1957, Eckert & Forster Angew Chem, Int Ed Engl 26 894 1987, Aldrichimica Acta 21 47 1988, Beilstein 3 H 17, 3 I 8, 3 II 16, 3 III 36, 3 IV 33.]
Bis(trichlormethyl)carbonat Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
Ritonavir
4-Isocyanatobenzonitril
3-Bromophenyl isocyanate
3-Methoxyphenylisocyanat
2-CHLOROBENZYL CHLOROFORMATE
1-CHLORO-2-METHYLPROPYL CHLOROFORMATE
Fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate
2,2,2-Trichlorethylchlorformiat
4-DIMETHYLAMINOPHENYL ISOCYANATE
2-Methoxyphenylisocyanat
N-Boc-N'-(2-chlorobenzyloxycarbonyl)-L-lysine
Bis(p-nitrophenyl)carbonat
Pentyl isocyanate
Phenylchlorformiat
4-Methylbenzyl isocyanate
H-LYS(2-CL-Z)-OH
(S)-3-TERT-BUTYL-2,5-PIPERAZINEDIONE
5-FLUORO-2H-3,1-BENZOXAZINE-2,4(1H)-DIONE
α,α,α-Trifluor-o-tolylisocyanat
4-(2'-Oxobenzimidazolin-1'-yl)piperidin
2-Chlorphenylisocyanat
(S)-(-)-4-tert-Butyloxazolidine-2,5-dione
Tetranatrium-3,3'-[carbonylbis[imino(2-methyl-4,1-phenylen)azo]]bisnaphthalin-1,5-disulfonat
3-Trifluormethylphenylisocyanat
4-Methoxyphenylisocyanat
3,5-DIMETHYLISOXAZOL-4-YL ISOCYANATE
2-FLUOROPHENYL ISOCYANATE
2-CHLORO-5-(TRIFLUOROMETHYL)PHENYL ISOCYANATE
1-Naphthylisocyanat
3,4-(METHYLENEDIOXY)PHENYL ISOCYANATE
5-Bromthiophen-2-carbaldehyd
4-Fluorphenylisocyanat
(1-METHYL-1H-PYRROL-2-YL)METHYLAMINE
2-Naphthylisocyanat
Tetranatrium-5,5'-[carbonylbis[imino(2-sulfonato-4,1-phenylen)azo]]bis(6-amino-4-hydroxynaphthalin-2-sulfonat)
1,5-Diphenylcarbonohydrazid
4-Methoxybenzyl isocyanate
4-Fluorphenylisocyanat
3,4-(METHYLENEDIOXY)PHENYL ISOCYANATE
