88-46-0

Basic information

• Product Name: 2,5-dihydroxybenzenesulphonic acid
• Synonyms: 2,5-dihydroxybenzenesulphonic acid;EINECS 201-833-4;Dobesilate
• CAS NO: 88-46-0
• Molecular Formula: C₆H₆O₅S
• Molecular Weight: 190.17384
• EINECS: 201-833-4
• Mol File: 88-46-0.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• Density: 1.744 g/cm³
• Refractive Index: 1.657
• PKA: -0.51±0.30(Predicted)
• CAS DataBase Reference: 2,5-dihydroxybenzenesulphonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-dihydroxybenzenesulphonic acid(88-46-0)
• EPA Substance Registry System: 2,5-dihydroxybenzenesulphonic acid(88-46-0)

Safety Data

• Hazardous Substances Data: 88-46-0(Hazardous Substances Data)

Usage

Originator

Dicynone,Delalande,France,1965

Definition

ChEBI: A dihydroxybenzenesulfonic acid that is hydroquinone in which one of the phenyl hydrogens is substituted by a sulfonic acid group.

Manufacturing Process

163 grams of pure diethylamine bisulfite are added to an ethyl alcohol solution of 108 grams of 1,4-benzoquinone at a temperature not above 5°C and under continuous stirring. After reaction, the alcohol is removed by distilling under vacuum. The product is recrystallized from ethyl alcohol at 80°C. Yield: 198 grams of diethylammonium cyclohexadienol 4-one-1- sulfonate-4. MP 125°C.

InChI:InChI=1/C6H6O5S/c7-4-1-2-5(8)6(3-4)12(9,10)11/h1-3,7-8H,(H,9,10,11)

Synthetic route

2,5-bis(acetyloxy)benzenesulfonic acid → dobesilate (88-46-0)

Conditions	Yield
With water; sodium hydroxide at 40℃; for 2h; Temperature;	91.1%

p-benzoquinone (106-51-4) → dobesilate (88-46-0) + hydroquinone (123-31-9)

Conditions	Yield
With sulfur dioxide In not given 0-80°C;	A 20% B 80%
With SO2 In not given 0-80°C;	A 20% B 80%
With sulphurous acid

p-benzoquinone (106-51-4) + sodium sulfite (7757-83-7) → dobesilate (88-46-0) + hydroquinone (123-31-9) + dithionic acid (14970-71-9)

Conditions	Yield
byproducts: H2SO4; slight amount of Na2S2O6;	A 57% B 3% C n/a
byproducts: H2SO4; slight amount of Na2S2O6;	A 57% B 3% C n/a

p-benzoquinone (106-51-4) + sodium sulfite (7757-83-7) → dobesilate (88-46-0)

Conditions	Yield
addn. of alkali;	35%
addn. of alkali;	35%

2,5-dichlorobenzenesulfonic acid (88-42-6) → dobesilate (88-46-0)

Conditions	Yield
With sodium hydroxide at 200℃; in einem Kupferkessel;

hydroquinone (123-31-9) → dobesilate (88-46-0)

Conditions	Yield
With sulfuric acid at 50 - 100℃; Kinetik;
With oxygen; sodium sulfite
Darst. durch Sulfurieren;

p-benzoquinone (106-51-4) → 2,5-dihydroxybenzene-1,4-disulphonic acid (4444-23-9) + dobesilate (88-46-0)

Conditions	Yield
With sodium sulfite

p-benzoquinone (106-51-4) → dobesilate (88-46-0)

Conditions	Yield
With sodium sulfite

hydroquinone (123-31-9) → 1,4-bis-sulfooxy-benzene (2458-55-1) + sulfuric acid mono-(4-hydroxy-phenyl ester) (17438-29-8) + dobesilate (88-46-0)

Conditions	Yield
With sulfur trioxide In nitromethane-d3 at 20℃; Product distribution; (with 1 equiv. SO3); product distribution between 10 and 10000 min;

hydroquinone (123-31-9) → sulfuric acid mono-(4-hydroxy-phenyl ester) (17438-29-8) + 2,5-dihydroxybenzene-1,4-disulphonic acid (4444-23-9) + dobesilate (88-46-0) + 2,5-dihydroxy-benzene-1,3-disulfonic acid (81010-88-0) + 2-Hydroxy-5-sulfooxy-benzene-1,3-disulfonic acid + 2-Hydroxy-5-sulfooxy-benzenesulfonic acid

Conditions	Yield
With sulfuric acid In water at 25℃; for 18.8889h; Product distribution; Rate constant; various times, concentrations;

sulfur trioxide (7446-11-9) + hydroquinone (123-31-9) → dobesilate (88-46-0)

Conditions	Yield
unter einer Glasglocke;

p-benzoquinone (106-51-4) + Na2SO3 → dobesilate (88-46-0)

p-benzoquinone (106-51-4) + Na2SO3 → dobesilate (88-46-0) + β-hydroquinonedisulfonic acid

water (7732-18-5) + p-benzoquinone (106-51-4) + SO2 → dobesilate (88-46-0) + hydroquinone (123-31-9)

benzene-1,4-diyl diacetate (1205-91-0) → dobesilate (88-46-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: chlorosulfonic acid / 1,2-dichloro-ethane / 2.5 h / 5 - 90 °C 2: sodium hydroxide; water / 2 h / 40 °C View Scheme

dabigatran etexilate (211915-06-9) + dobesilate (88-46-0) → dabigatran etexilate 2,5-dihydroxybenzenesulfonate

Conditions	Yield
In ethyl acetate at 30℃; Solvent; Temperature;	92%

Upstream product

• 88-42-6 2,5-dichlorobenzenesulfonic acid 
• 123-31-9 hydroquinone 
• 106-51-4 p-benzoquinone 
• 7446-11-9 sulfur trioxide 
• 7732-18-5 water 
• 7757-83-7 sodium sulfite 
• 1205-91-0 benzene-1,4-diyl diacetate 

Downstream Products

• 877-19-0 3,6-dioxo-cyclohexa-1,4-dienesulfonic acid 
• 23149-36-2 2,3,5-tribromo-1,4-dihydroxybenzene 
• 118-75-2 chloranil 
• 2624-44-4 ethamsylate 
• 4444-23-9 2,5-dihydroxybenzene-1,4-disulphonic acid 
• 20123-80-2 calcium dobesilate 
• 123-31-9 hydroquinone 
• 81010-88-0 2,5-dihydroxy-benzene-1,3-disulfonic acid 

Relevant articles and documents

Etamsylate and calcium dobesilate impurities, and preparation method and application thereof

The invention discloses four types of etamsylate and calcium dobesilate impurities, namely a 2,5-dihydroxy-1,4-benzene disulfonic acid compound, a 2,4-dihydroxy-1,5-benzene disulfonic acid compound, a2,5-dihydroxy benzene sulfonate compound and a 2,3-dihydroxy benzene sulfonic acid compound, and a preparation method thereof. The purity of all the prepared compound is 96% or more, and the compounds can be used for the quality control of etamsylate and calcium dobesilate bulk drugs and preparations.

C10H17NO5S.1/20H2O compound

The invention discloses a C10H17NO5S.1/20H2O compound and a preparation method thereof. The compound is measured by using a powder X-ray diffraction measurement method, and shows characteristic diffraction peaks represented by a diffraction angle of 2theta +/- 0.2 degrees at the places of 13.4 degrees, 17.2 degrees, 20.5 degrees, 21.4 degrees, 23.7 degrees, 24.5 degrees, 26.9 degrees, 28.0 degreesand 34.0 degrees. The C10H17NO5S.1/20H2O compound prepared by the preparation method has the advantages of good thermal stability, high purity, and weak hygroscopicity, has a simple process, a high yield and strong repeatability, and is suitable for industrial production.

Hydroxybenzene disulphonic acid as well as calcium salt and preparation method thereof

A preparation method of hydroxybenzene disulphonic acid comprises steps as follows: hydroquinone and water-containing sulphuric acid are subjected to a reaction to produce a liquid containing hydroxybenzene sulphonic acid, the liquid containing hydroxybenzene sulphonic acid is subjected to a reaction with fuming sulphuric acid, and hydroxybenzene disulphonic acid is produced. A preparation methodof calcium hydroxybenzene disulphonate comprises steps as follows: a liquid containing hydroxybenzene sulphonic acid is produced from hydroquinone and sulphuric acid and is subjected to a reaction with fuming sulphuric acid, a liquid containing hydroxybenzene disulphonic acid is produced and subjected to a reaction with calcium carbonate, and calcium hydroxybenzene disulphonate is produced. The preparation method of hydroxybenzene disulphonic acid, calcium hydroxybenzene disulphonate and the preparation method of calcium hydroxybenzene disulphonate have the advantage that large-scale synthesisof hydroxybenzene disulphonic acid and calcium hydroxybenzene disulphonate is expected to be realized with a certain technology.