8-Amino-7-chloro-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid

Base Information

• Chemical Name: 8-Amino-7-chloro-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid
• CAS No.: 148703-26-8
• Molecular Formula: C9H8ClNO4
• Molecular Weight: 229.61712
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID80472362
• Wikidata: Q82301258
• Mol file: 148703-26-8.mol

Synonyms:148703-26-8;8-Amino-7-chloro-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid;5-amino-6-chloro-2,3-dihydro-1,4-benzodioxine-8-carboxylic acid;8-amino-7-chloro-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid;8-amino-7-chloro-1,4-benzodioxan-5-carboxylic acid;SCHEMBL2944408;DTXSID80472362;KGEWUGWPCVDMCP-UHFFFAOYSA-N;8-Amino-7-chloro-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylicacid;CS-0446837

Chemical Property of 8-Amino-7-chloro-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid

Chemical Property:

• PSA: 81.78000
• LogP: 1.97280
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 229.0141854
• Heavy Atom Count: 15
• Complexity: 263

Purity/Quality:

97% ^*data from raw suppliers

8-Amino-7-chloro-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COC2=C(O1)C(=CC(=C2N)Cl)C(=O)O

Technology Process of 8-Amino-7-chloro-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid

There total 6 articles about 8-Amino-7-chloro-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid 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: 67.7%

8-(acetylamino)-2,3-dihydro-1,4-benzodioxin-5-carboxylic acid (66411-27-6) → 8-amino-7-chloro-2,3-dihydro-benzo[1,4]dioxine-5-carboxylic acid (148703-26-8)

Guidance literature:

With N-chloro-succinimide; acetic acid; at 50 - 85 ℃; for 8h; Industrial scale;

DOI:10.1021/acs.oprd.6b00262

Reference yield:

8-Acetylamino-7-chloro-2,3-dihydro-benzo[1,4]dioxine-5-carboxylic acid (152045-64-2) → 8-amino-7-chloro-2,3-dihydro-benzo[1,4]dioxine-5-carboxylic acid (148703-26-8)

Guidance literature:

With sodium hydroxide; water; Heating;

DOI:10.1021/jm00077a018

Reference yield:

6,7-dibromo-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid (66411-17-4) → 8-amino-7-chloro-2,3-dihydro-benzo[1,4]dioxine-5-carboxylic acid (148703-26-8)

Guidance literature:

Multi-step reaction with 4 steps

1: acetic acid; sulfuric acid; nitric acid / 12 h / 11 - 43 °C / Industrial scale

2: triethylamine; hydrogen; palladium on activated charcoal / methanol; water / 0.5 h / 50 - 75 °C / 3375.34 Torr / Industrial scale

3: 15 - 25 °C / Inert atmosphere; Industrial scale

4: acetic acid; N-chloro-succinimide / 8 h / 50 - 85 °C / Industrial scale

With N-chloro-succinimide; sulfuric acid; palladium on activated charcoal; hydrogen; nitric acid; acetic acid; triethylamine; In methanol; water;

DOI:10.1021/acs.oprd.6b00262

upstream raw materials:

8-Acetylamino-7-chloro-2,3-dihydro-benzo[1,4]dioxine-5-carboxylic acid

8-(acetylamino)-2,3-dihydro-1,4-benzodioxin-5-carboxylic acid

6,7-dibromo-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid

2,3-dihydro-1,4-benzodioxine-5-carboxylic acid

Downstream raw materials:

(1-butyl-4-piperidinylmethyl)-8-amino-7-chloro-1,4-benzodioxan-5-carboxylate