Benzyloxyacetyl chloride Chemical Properties

Melting point:

120 °C (decomp)

Boiling point:

84-87 °C/0.4 mmHg (lit.)

Density 

1.17 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.523(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

form 

Powder or Cyrstals

color 

White

Water Solubility 

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 DataBase Reference

19810-31-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

14-34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

F 

10-19

HazardClass 

8

PackingGroup 

III

HS Code 

29189900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Benzyloxyacetyl chloride Usage And Synthesis

Chemical Properties

Colorless to yellow liquid

Uses

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.

Uses

Commonly employed reagent for asymmetric synthesis of β-lactams.1,2

Synthesis

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.

References

[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

Benzyloxyacetyl chloride(19810-31-2)Related Product Information

• Trichloroacetyl chloride
• 4-Methoxybenzylchloride
• Sodium chloride
• Choline chloride
• Phenoxyacetyl chloride
• Ammonium chloride
• Calcium chloride
• Thionyl chloride
• Oxalyl chloride
• Zinc chloride
• Chloroacetyl chloride
• Acetyl chloride
• Phenylacetyl chloride
• Bromoacetyl chloride
• Acetoxyacetyl chloride
• Potassium chloride
• BENZYLOXYACETALDEHYDE
• 2-Chloroethyl ethyl ether