4-(Chloroacetyl)-3,4-dihydro-2H-1,4-benzoxazine

Base Information

• Chemical Name: 4-(Chloroacetyl)-3,4-dihydro-2H-1,4-benzoxazine
• CAS No.: 22178-82-1
• Molecular Formula: C10H10 Cl N O2
• Molecular Weight: 211.6449
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID00544873
• Wikidata: Q82422168
• Mol file: 22178-82-1.mol

Synonyms:22178-82-1;4-(CHLOROACETYL)-3,4-DIHYDRO-2H-1,4-BENZOXAZINE;1-(2H-Benzo[b][1,4]oxazin-4(3H)-yl)-2-chloroethanone;2-CHLORO-1-(2,3-DIHYDRO-1,4-BENZOXAZIN-4-YL)ETHANONE;2-Chloro-1-(2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)ethan-1-one;2H-1,4-Benzoxazine, 4-(chloroacetyl)-3,4-dihydro- (8CI,9CI);SCHEMBL10858113;DTXSID00544873;XAA17882;MFCD08691656;AKOS009489700;BS-37609;CS-0328298;Z415725932;2-chloro-1-(2, 3-dihydro-1, 4-benzoxazin-4-yl)ethanone;2-Chloro-1-(2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethan-1-one

Chemical Property of 4-(Chloroacetyl)-3,4-dihydro-2H-1,4-benzoxazine

Chemical Property:

• Vapor Pressure: 6.43E-07mmHg at 25°C
• Refractive Index: 1.572
• Boiling Point: 409.6°C at 760 mmHg
• Flash Point: 201.5°C
• PSA: 29.54000
• Density: 1.314g/cm³
• LogP: 1.71580
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 211.0400063
• Heavy Atom Count: 14
• Complexity: 222

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-(Chloroacetyl)-3,4-dihydro-2H-1,4-benzoxazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COC2=CC=CC=C2N1C(=O)CCl

Technology Process of 4-(Chloroacetyl)-3,4-dihydro-2H-1,4-benzoxazine

There total 4 articles about 4-(Chloroacetyl)-3,4-dihydro-2H-1,4-benzoxazine 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%

1,4-benzoxazine (5735-53-5) + chloroacetyl chloride (79-04-9) → 2-chloro-1-(2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)ethan-1-one (22178-82-1)

Guidance literature:

With pyridine; In benzene; Ambient temperature;

DOI:10.1016/S0960-894X(97)00261-8

Reference yield:

2-hydroxynitrobenzene (88-75-5,78813-12-4) → 2-chloro-1-(2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)ethan-1-one (22178-82-1)

Guidance literature:

Multi-step reaction with 4 steps

1: acetic acid; iron / ethanol; water

2: potassium carbonate / acetonitrile / 20 h / Reflux

3: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

4: triethylamine / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; iron; potassium carbonate; acetic acid; triethylamine; In tetrahydrofuran; ethanol; water; acetonitrile;

DOI:10.1002/ardp.201800024

Reference yield:

2-amino-phenol (95-55-6) → 2-chloro-1-(2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)ethan-1-one (22178-82-1)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / acetonitrile / 20 h / Reflux

2: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

3: triethylamine / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; potassium carbonate; triethylamine; In tetrahydrofuran; acetonitrile;

DOI:10.1002/ardp.201800024

upstream raw materials:

1,4-benzoxazine

chloroacetyl chloride

2-hydroxynitrobenzene

2-amino-phenol

Refernces

• 1、 Zhao, He,Thurkauf, Andrew,He, Xiaoshu,Hodgetts, Kevin,Zhang, Xiaoyan,Rachwal, Stanislaw,Kover, Renata X.,Hutchison, Alan,Peterson, John,Kieltyka, Andrzej,Brodbeck, Robbin,Primus, Renee,Wasley, Jan W.F.. "Indoline and piperazine containing derivatives as a novel class of mixed D2/D4 receptor antagonists. Part 1: Identification and structure-activity relationships". . p. 3105 - 3109. Retrieved 2007/10/03.