3,7-dihydroxytropolone

Base Information

• Chemical Name: 3,7-dihydroxytropolone
• CAS No.: 85233-29-0
• Molecular Formula: C₇H₆O₄
• Molecular Weight: 154.122
• Mol file: 85233-29-0.mol

Synonyms:3,4-Dihydroxytropolone;BMY 28438

Chemical Property of 3,7-dihydroxytropolone

Chemical Property:

• Vapor Pressure: 0.0201mmHg at 25°C
• Boiling Point: 223°C at 760 mmHg
• Flash Point: 102.9°C
• PSA: 77.76000
• Density: 1.802g/cm³
• LogP: 0.16360

Purity/Quality:

99%min ^*data from raw suppliers

2,3,7-TRIHYDROXYCYCLOHEPTA-2,4,6-TRIEN-1-ONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3,7-dihydroxytropolone

There total 9 articles about 3,7-dihydroxytropolone 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: 87.0%

2,3,7-triacetoxytropone → 3,4-Dihydroxytropolone (85233-29-0)

Guidance literature:

In water; acetic acid; at 100 ℃; for 7h;

DOI:10.1246/bcsj.60.4325

Reference yield: 71.0%

3,4-Dimethyl-α-tropolone (69432-64-0) → 3,4-Dihydroxytropolone (85233-29-0)

Guidance literature:

With hydrogen bromide; In acetic acid; for 2h; Heating;

Reference yield:

(1α,2α,3α,6α)-7,7-dibromobicyclo<4.1.0>hept-4-ene-2,3-diol (137834-24-3,142732-32-9) → 3,4-Dihydroxytropolone (85233-29-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 1. NaH / 1. THF, a.) 0 deg C to r.t., b.) r.t., 0.5 h; 2. a.) 0 deg C to r.t., b.) r.t., 17 h

3: 1. trifluoroacetic anhydride (TFFA), DMSO; 2. Et₃N / 1. CH₂Cl₂, -60 deg C, 2 h; 2. a.) -60 deg C, 1.5 h, b.) -60 deg C to 20 deg C, 0.5 h, c.) 2 h

4: 87 percent / pyridine / CH₂Cl₂ / 15 h / Ambient temperature

5: 94 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / 3 h / 50 °C

6: 71 percent / 48percent aq. HBr / acetic acid / 2 h / Heating

With pyridine; hydrogen bromide; sodium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; acetic acid;

upstream raw materials:

puberulic acid

3,4-Dimethyl-α-tropolone

(1α,2α,3α,6α)-7,7-dibromobicyclo<4.1.0>hept-4-ene-2,3-diol

(1α,4α,5α,6α)-7,7-Dibromo-4,5-dimethoxybicyclo<4.1.0>hept-2-ene

Downstream raw materials:

3-Hydroxy-4-(4-nitrobenzyloxy)tropolone

3,4-Bis(4-nitrobenzyloxy)tropone

2,3,4-Tris(4-nitrobenzyloxy)tropone

2,3,7-Tris(4-nitrobenzyloxy)tropone

Refernces

• 1、 Takeshita, Hitoshi,Mori, Akira,Kusaba, Tomoyuki,Watanabe, Hiroyasu. "Preparation of Polyacetoxytropones and Polyhydroxytropolones by Acetolysis and Hydrolysis of Halotroponoids by Acetyl Trifluoroacetate with Exhaustive Displacement of Halogens on the Tropone Ring. Predominant Formation of Reductive Acetolysates from Fully-Substituted Tropones". . p. 4325 - 4334. Retrieved 2007/10/02.