cis-4,5-Dihydroxycyclohexa-2,6-diene-1,2-dicarboxylic acid

Base Information

• Chemical Name: cis-4,5-Dihydroxycyclohexa-2,6-diene-1,2-dicarboxylic acid
• CAS No.: 130073-64-2
• Molecular Formula: C8H8 O6
• Molecular Weight: 200.15
• DSSTox Substance ID: DTXSID501164430
• Nikkaji Number: J478.875C
• Wikidata: Q27102535
• Metabolomics Workbench ID: 51004
• Mol file: 130073-64-2.mol

Synonyms:130073-64-2;cis-4,5-dihydroxycyclohexa-2,6-diene-1,2-dicarboxylic acid;Phthalate-4,5-cis-dihydrodiol;(4S,5R)-4,5-dihydroxycyclohexa-2,6-diene-1,2-dicarboxylic acid;rel-(4R,5S)-4,5-dihydroxycyclohexa-2,6-diene-1,2-dicarboxylic acid;2,6-Cyclohexadiene-1,2-dicarboxylic acid, 4,5-dihydroxy-, (4R,5S)-rel-;C04783;SCHEMBL813574;CHEBI:17692;1,2-DICARBOXY-CIS-4,5-DIHYDROXYCYCLOHEXA-2,6-DIENE;DTXSID501164430;Q27102535;(4R,5S)-4,5-dihydroxycyclohexa-2,6-diene-1,2-dicarboxylic acid;rel-(4R,5S)-4,5-Dihydroxy-2,6-cyclohexadiene-1,2-dicarboxylic acid

Chemical Property of cis-4,5-Dihydroxycyclohexa-2,6-diene-1,2-dicarboxylic acid

Chemical Property:

• Vapor Pressure: 7.84E-12mmHg at 25°C
• Refractive Index: 1.6630 (estimate)
• Boiling Point: 494°Cat760mmHg
• PKA: 3.57±0.70(Predicted)
• Flash Point: 266.7°C
• PSA: 115.06000
• Density: 1.861g/cm³
• LogP: -1.25620
• Storage Temp.: -20°C
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 200.03208797
• Heavy Atom Count: 14
• Complexity: 306

Purity/Quality:

PhthalicAcid4,5-cis-Dihydrodiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=CC(C1O)O)C(=O)O)C(=O)O
• Isomeric SMILES: C1=C(C(=C[C@@H]([C@@H]1O)O)C(=O)O)C(=O)O
• Uses: Phthalic Acid 4,5-cis-Dihydrodiol is a bacterial metabolite of phthalic acid (P384480) which is an organic reagent used to synthesize phthalates.

Technology Process of cis-4,5-Dihydroxycyclohexa-2,6-diene-1,2-dicarboxylic acid

There total 8 articles about cis-4,5-Dihydroxycyclohexa-2,6-diene-1,2-dicarboxylic 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:

glutamic acid sodium salt → phthalic acid cis-4,5-dihydrodiol (130073-64-2,128666-29-5)

Guidance literature:

In ethanol;

Reference yield:

bis<2-(trimethylsilyl)ethyl> (2-exo,3-endo,5-exo,6-exo)-5,6-dihydroxy-7-oxabicyclo<2.2.1>heptane-2,3-dicarboxylate (141849-04-9) → phthalic acid cis-4,5-dihydrodiol (130073-64-2,128666-29-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / p-toluenesulfonic acid monohydrate / acetone / 4 h / 60 °C

2: 54 percent / lithium hexamethyldisilazide / tetrahydrofuran / a) - 42 deg C, 4 h, b) -23 deg C, 1.5 h

3: 88 percent / methanesulfonyl chloride, triethylamine / CH₂Cl₂ / 1 h / 0 °C

4: 70 percent / iodine / methanol / 3 h / Heating

5: 70 percent Turnov_. / tetra(n-butyl)ammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature

With tetrabutyl ammonium fluoride; iodine; methanesulfonyl chloride; triethylamine; lithium hexamethyldisilazane; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; acetone;

DOI:10.1021/jo00040a023

Reference yield:

bis<2-(trimethylsilyl)ethyl> (2-exo,3-endo)-7-oxabicyclo<2.2.1>hept-5-ene-2,3-dicarboxylate (141849-03-8) → phthalic acid cis-4,5-dihydrodiol (130073-64-2,128666-29-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / trimethylamine N-oxide dihydrate / osmium tetroxide / 2-methyl-propan-2-ol; acetone / Ambient temperature

2: 100 percent / p-toluenesulfonic acid monohydrate / acetone / 4 h / 60 °C

3: 54 percent / lithium hexamethyldisilazide / tetrahydrofuran / a) - 42 deg C, 4 h, b) -23 deg C, 1.5 h

4: 88 percent / methanesulfonyl chloride, triethylamine / CH₂Cl₂ / 1 h / 0 °C

5: 70 percent / iodine / methanol / 3 h / Heating

6: 70 percent Turnov_. / tetra(n-butyl)ammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature

With trimethylamine-N-oxide; tetrabutyl ammonium fluoride; iodine; methanesulfonyl chloride; triethylamine; lithium hexamethyldisilazane; osmium(VIII) oxide; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; acetone; tert-butyl alcohol;

DOI:10.1021/jo00040a023

upstream raw materials:

bis<2-(trimethylsilyl)ethyl> cis-5,6-dihydroxy-1,3-cyclohexadiene-2,3-dicarboxylate

bis<2-(trimethylsilyl)ethyl> (2-exo,3-endo)-7-oxabicyclo<2.2.1>hept-5-ene-2,3-dicarboxylate

bis<2-(trimethylsilyl)ethyl> cis-5,6-dihydroxy-1,3-cyclohexadiene-2,3-dicarboxylate O-acetonide

bis<2-(trimethylsilyl)ethyl> (2-exo,3-endo,5-exo,6-exo)-5,6-dihydroxy-7-oxabicyclo<2.2.1>heptane-2,3-dicarboxylate

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