Benzyloxyacetyl chloride

Bezeichnung:Benzyloxyacetyl chloride

CAS-Nr19810-31-2

Englisch Name:Benzyloxyacetyl chloride

CBNumberCB9167296

SummenformelC9H9ClO2

Molgewicht184.62

MOL-Datei19810-31-2.mol

Benzyloxyacetyl chloride physikalisch-chemischer Eigenschaften

Schmelzpunkt	120 °C (decomp)
Siedepunkt	84-87 °C/0.4 mmHg (lit.)
Dichte	1.17 g/mL at 25 °C (lit.)
Brechungsindex	n20/D 1.523(lit.)
Flammpunkt	>230 °F
storage temp.	2-8°C
Aggregatzustand	Powder or Cyrstals
Farbe	White
Wasserlöslichkeit	Reacts with water.
Sensitive	Moisture Sensitive
BRN	1947363
InChI	InChI=1S/C9H9ClO2/c10-9(11)7-12-6-8-4-2-1-3-5-8/h1-5H,6-7H2
InChIKey	QISAUDWTBBNJIR-UHFFFAOYSA-N
SMILES	C(Cl)(COCC1=CC=CC=C1)=O
CAS Datenbank	19810-31-2(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	C
R-Sätze:	14-34
S-Sätze:	26-36/37/39-45
RIDADR	UN 3265 8/PG 2
WGK Germany	3
F	10-19
HazardClass	8
PackingGroup	III
HS Code	29189900
Speicherklasse	8A - Combustible corrosive hazardous materials
Hazard Classifications	Skin Corr. 1B

Gefahreninformationscode (GHS)

Benzyloxyacetyl chloride Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R14:Reagiert heftig mit Wasser.
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
Colorless to yellow liquid
Verwenden
Benzyloxyacetyl chloride is a reagent used to construct substituted 2-azetidinones for further elaboration into annulated β-lactams. It is a commonly employed reagent for asymmetric synthesis of β-lactams. It is also used in preparation of (S)-3-(methylamino)-3-((R)-pyrrolidin-3-yl)propanenitrile, key intermediate in the preparation of fluoroquinolone antibiotic for respiratory tract infections, non-racemic helicene and β-lactams.
Verwenden
Commonly employed reagent for asymmetric synthesis of β-lactams.1,2
Synthese

30379-55-6

19810-31-2

Example 1 (a) Synthesis of benzyloxyacetyl chloride: to a solution of dichloromethane (50 mL) containing benzyloxyacetic acid (10.0 g, 60.0 mmol, 8.6 mL) was sequentially added oxalyl chloride (9.1 g, 72.0 mmol, 6.0 mL) and N,N-dimethylformamide (DMF, 30.0 mg, 0.4 mmol, 32.0 μL). The reaction mixture was stirred for 3 h at room temperature. Rapid gas release was observed at the beginning of the reaction, which gradually stopped as the reaction progressed. Upon completion of the reaction, the dichloromethane solution was concentrated under reduced pressure to give a colloidal product. Subsequently, additional oxalyl chloride (4.5 g, 35.7 mmol, 3.0 mL), dichloromethane (50 mL), and a drop of DMF were added to the gelatinous product, and the reaction mixture was again stirred for 2 h, during which a rapid gas release was observed. Finally, the reaction mixture was concentrated under reduced pressure to afford benzyloxyacetyl chloride (1) 11.0 g (in quantitative yield) as a gel. The structure of the product was confirmed by 13C NMR (75 MHz, CDCl3) with chemical shifts of δ 73.6, 74.8, 128.1, 128.4, 128.6, 130.0 and 171.9.
Einzelnachweise
[1] Patent: US2013/177501, 2013, A1. Location in patent: Paragraph 0152
[2] Patent: WO2015/7834, 2015, A1. Location in patent: Page/Page column 17
[3] Patent: WO2015/40087, 2015, A1. Location in patent: Page/Page column 13; 14
[4] Patent: US9168317, 2015, B2. Location in patent: Page/Page column 20
[5] Patent: US9314541, 2016, B2. Location in patent: Page/Page column 21

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