1-Chlorethylchlorformiat

Bezeichnung:1-Chlorethylchlorformiat

CAS-Nr50893-53-3

Englisch Name:1-Chloroethyl chloroformate

CBNumberCB5320341

SummenformelC3H4Cl2O2

Molgewicht142.97

MOL-Datei50893-53-3.mol

Synonyma

1-Chlorethylchlorformiat

1-Chlorethylchlorformiat physikalisch-chemischer Eigenschaften

Schmelzpunkt	-65°C
Siedepunkt	118-119 °C (lit.)
Dichte	1.325 g/mL at 25 °C (lit.)
Dampfdruck	3.25 psi ( 20 °C)
Brechungsindex	n20/D 1.422(lit.)
Flammpunkt	105 °F
storage temp.	2-8°C
Löslichkeit	Miscible with most organic solvents.
Aggregatzustand	Liquid
Farbe	Clear colorless
Sensitive	Moisture Sensitive
BRN	1747601
Stabilität	Hygroscopic, Moisture Sensitive
InChIKey	QOPVNWQGBQYBBP-UHFFFAOYSA-N
CAS Datenbank	50893-53-3(CAS DataBase Reference)
NIST chemische Informationen	«ALPHA»-chloroethyl chloroformate(50893-53-3)

Sicherheit

Kennzeichnung gefährlicher	T
R-Sätze:	10-22-23-34
S-Sätze:	26-36/37/39-45
RIDADR	UN 2742 6.1/PG 2
WGK Germany	3
F	10-19-21
TSCA	No
HazardClass	6.1
PackingGroup	II
HS Code	29159000

Gefahreninformationscode (GHS)

1-Chloroethyl chloroformate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R10:Entzündlich.
R22:Gesundheitsschädlich beim Verschlucken.
R23:Giftig beim Einatmen.
R34:Verursacht Verätzungen.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
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).
Chemische Eigenschaften
Clear and colorless liquid
Verwenden
1-Chloroethyl chloroformate was used:
- for N-demethylation reaction during determination of multiple drugs of abuse in biological fluids using capillary electrophoresis with native fluorescence and laser-induced fluorescence detection
- as catalyst in chemoselective desilylation of silyl-protected alcohols
- as reagent in N-demethylation of tertiary amines to produce drug metabolite reference material for forensic toxicological applications
- as reagent to cleave benzhydryl groups from amines
Verwenden
Reagent for the selective N-dealkylation of tertiary amines in high yields.
synthetische
1-Chloroethyl chloroformate is obtained by stirring phosgene and acetaldehyde in the presence of benzyltributylammonium chloride, followed by distillation (96% yield).
Reaktivität anzeigen
1-chloroethyl chloroformate was found to be the potential reagent of choice for the N-demethylation of tertiary amines. The reaction was performed by refluxing in dry 1,2-dichloroethane under nitrogen, and the carbamate intermediate was hydrolysed by treatment with methanol[1].

The debenzylation conditions were mediated by 1-chloroethyl chloroformate (green), which gave the expected secondary amine 3 (blue) an excellent yield. The debenzylation proceeds presumably via a carbamate intermediate following the reaction of the starting material 6 with 1-chloroethyl chloroformate and loss of benzyl chloride. Subsequent decarboxylation, promoted by excess methanol and reflux conditions, produced the desired secondary amine 3.
Synthese
An initiator solution was formed by dissolving 0.33 gram of 2,2'-azobis(2-methylpropanenitrile) in 61 grams of ethyl chloroformate. The initiator solution was charged to the syringe. The flask was charged with 590 grams of ethyl chloroformate. The flask was then heated to obtain close to maximum reflux without flooding. The syringe pump was set to feed approximately 5 millilitres of the initiator solution per hour. The introduction of molecular chlorine gas through the first inlet at 0.47 gram per minute was then begun. During the reaction, the condenser functioned as a total reflux condenser. The chlorine introduction was terminated twelve hours later, and the reaction mixture was allowed to cool. The final reaction product weighed 806 grams. Gas chromatographic analysis of the reaction product showed it to contain 18.8 area percent of ethyl chloroformate, 45.4 area percent of 1-chloroethyl chloroformate, 34.7 area percent of 2-chloroethyl chloroformate, and 1.06 area percent of dichlorinated ethyl chloroformate.
Einzelnachweise
[1] Anna Pelander, Tapio A. Hase, Ilkka Ojanper? . “Preparation of N-demethylated drug metabolites for analytical purposes using 1-chloroethyl chloroformate.” Forensic science international 85 3 (1997): Pages 193-198.
[2] Katrina A Badiola. “Efficient Synthesis and Anti-Tubercular Activity of a Series of Spirocycles: An Exercise in Open Science.” PLoS ONE (2014): e111782.

1-Chloroethyl chloroformate Upstream-Materialien And Downstream Produkte

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