4',5'-Dichloro-3',6'-dihydroxy-2',7'-dimethoxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-5-carboxylic acid

Base Information

• Chemical Name: 4',5'-Dichloro-3',6'-dihydroxy-2',7'-dimethoxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-5-carboxylic acid
• CAS No.: 82855-39-8
• Molecular Formula: C₂₃H₁₄Cl₂O₉
• Molecular Weight: 505.265
• DSSTox Substance ID: DTXSID80436186
• Wikidata: Q82251432
• Mol file: 82855-39-8.mol

Synonyms:82855-39-8;4',5'-Dichloro-3',6'-dihydroxy-2',7'-dimethoxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-5-carboxylic acid;4',5'-dichloro-3',6'-dihydroxy-2',7'-dimethoxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-carboxylic acid;4',5'-DICHLORO-3',6'-DIHYDROXY-2',7'-DIMETHOXY-3-OXO-3H-SPIRO[2-BENZOFURAN-1,9'-XANTHENE]-5-CARBOXYLIC ACID;SCHEMBL345532;DTXSID80436186;CS-0373884;A915526;4',5'-Dichloro-3',6'-dihydroxy-2',7'-dimethoxy-3-oxo-3H-spiro[isobenzo[b]furan-1,9'-xanthene]-5-carboxylic acid;4',5'-Dichloro-3',6'-dihydroxy-2',7'-dimethoxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-5-carboxylicacid

Chemical Property of 4',5'-Dichloro-3',6'-dihydroxy-2',7'-dimethoxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-5-carboxylic acid

Chemical Property:

• PSA: 131.75000
• LogP: 4.68800
• Storage Temp.: 2-8°C
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 504.0014874
• Heavy Atom Count: 34
• Complexity: 790

Purity/Quality:

97% ^*data from raw suppliers

4',5'-Dichloro-3',6'-dihydroxy-2',7'-dimethoxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-5-carboxylic acid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=C2C(=C1)C3(C4=C(C=C(C=C4)C(=O)O)C(=O)O3)C5=CC(=C(C(=C5O2)Cl)O)OC)Cl)O

Technology Process of 4',5'-Dichloro-3',6'-dihydroxy-2',7'-dimethoxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-5-carboxylic acid

There total 5 articles about 4',5'-Dichloro-3',6'-dihydroxy-2',7'-dimethoxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-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:

2-chloro-4-methoxybenzene-1,3-diol + trimellitic Anhydride (552-30-7,145253-53-8) → 4',5'-dichloro-2',7'-dimethoxy-6-carboxyfluorescein (82855-40-1) + 4',5'-dichloro-2',7'-dimethoxy-5-carboxyfluorescein (82855-39-8)

Guidance literature:

With methanesulfonic acid; tin(IV) chloride; at 40 ℃; for 6h;

DOI:10.1021/jo202229t

Reference yield:

2-chloro-3-hydroxy-4-methoxybenzaldehyde (37687-57-3) → 4',5'-dichloro-2',7'-dimethoxy-5-carboxyfluorescein (82855-39-8)

Guidance literature:

Multi-step reaction with 2 steps

1: selenium(IV) oxide; dihydrogen peroxide / dichloromethane / 48 h / 0 - 20 °C

2: methanesulfonic acid; tin(IV) chloride / 6 h / 80 °C

With selenium(IV) oxide; methanesulfonic acid; dihydrogen peroxide; tin(IV) chloride; In dichloromethane;

Reference yield:

isovanillin (621-59-0) → 4',5'-dichloro-2',7'-dimethoxy-6-carboxyfluorescein (82855-40-1) + 4',5'-dichloro-2',7'-dimethoxy-5-carboxyfluorescein (82855-39-8)

Guidance literature:

Multi-step reaction with 4 steps

1: chlorine / chloroform / 2.5 h

2: selenium(IV) oxide; dihydrogen peroxide / dichloromethane; water / 48 h / 20 °C

3: hydrogenchloride; methanol / 0.5 h / 20 °C

4: methanesulfonic acid; tin(IV) chloride / 6 h / 40 °C

With hydrogenchloride; methanol; selenium(IV) oxide; methanesulfonic acid; dihydrogen peroxide; chlorine; tin(IV) chloride; In dichloromethane; chloroform; water;

DOI:10.1021/jo202229t

upstream raw materials:

isovanillin

trimellitic Anhydride

2-chloro-3-hydroxy-4-methoxybenzaldehyde