Benzyloxyacetyl chloride

Base Information

• Chemical Name: Benzyloxyacetyl chloride
• CAS No.: 19810-31-2
• Molecular Formula: C9H9ClO2
• Molecular Weight: 184.622
• Hs Code.: 29189900
• Mol file: 19810-31-2.mol

Synonyms:Acetylchloride, (benzyloxy)- (6CI,8CI);Acetyl chloride, (phenylmethoxy)- (9CI);(Benzyloxy)acetyl chloride;(Phenylmethoxy)acetyl chloride;2-(Benzyloxy)acetylchloride;2-Phenylmethoxyacetyl chloride;Benzyloxyacetic chloride;a-(Benzyloxy)acetyl chloride;2-(benzyloxy)acetyl chloride;

Chemical Property of Benzyloxyacetyl chloride

Chemical Property:

• Vapor Pressure: 0.00339mmHg at 25°C
• Melting Point: 120 °C (decomp)
• Refractive Index: n20/D 1.523(lit.)
• Boiling Point: 224 °C at 760 mmHg
• Flash Point: 73.5 °C
• PSA: 26.30000
• Density: 1.244 g/cm³
• LogP: 1.96860
• Storage Temp.: −20°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: Reacts with water.

Purity/Quality:

99% ^*data from raw suppliers

2-(Benzyloxy)acetylChloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 14-34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

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

Technology Process of Benzyloxyacetyl chloride

There total 15 articles about Benzyloxyacetyl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

benzyloxyacetic acid (30379-55-6) → Benzyloxyacetyl chloride (19810-31-2)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20 ℃; for 5h;

Reference yield: 100.0%

6-iodoimidazo[1,5-a]pyridine-1-carboxylic acid → Benzyloxyacetyl chloride (19810-31-2)

Guidance literature:

With thionyl chloride; benzyloxyacetic acid; In dichloromethane; at 0 - 45 ℃; for 3h;

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → Benzyloxyacetyl chloride (19810-31-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH

2: 83 percent / thionyl chloride / 1) 0-10 deg C, 45 min; 2) 65 deg C, 30 min

With thionyl chloride; sodium hydride;

DOI:10.1021/jo00199a053

upstream raw materials:

benzyloxyacetic acid

benzyl alcohol

oxalyl dichloride

ethyl benzyloxyacetate

Downstream raw materials:

4,11-bis-benzyloxyacetyl-1,8-dioxa-4,11-diaza-cyclotetradecane-2,5,9,12-tetraone

2-Benzyloxy-peressigsaeure-tert.-butylester

N-(1'-methoxycarbonyl-ethyl)-N-benzyloxyacetyl-2,6-dimethylaniline

N-(1'-methoxycarbonyl-ethyl)-N-benzyloxyacetyl-2,3,6-trimethylaniline

Refernces

• 1、 -. "ISOINDOLE DERIVATIVE". Paragraph 0260. . Retrieved 2021/02/25.
• 2、 -. "TRANSGLUTAMINASE 2 (TG2) INHIBITORS". Paragraph 00735. . Retrieved 2020/03/02.