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Hydroquinone CAS 123-31-9 Factory supply
Cas No: 123-31-9
USD $ 6500.0-6500.0 / Metric Ton 1 Metric Ton 30000 Metric Ton/Day Wuhan Biet Co., Ltd Contact Supplier
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USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
High purity Best Price Hydroquinone
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Factory Supply 1,4-Benzenediol
Cas No: 123-31-9
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123-31-9 Usage

Brand name

Aida;Ambi- skin tone;Black and white;Creme des 3 fleur d'orient;Eldopaque forte;Eldoquin forte 4% cream;Epocler;Esoterica facial;Esoterica regular;Esoterica sensitive skin;Esoterica sunscreen;Melanex topical sollution;Melpaque hp;Melqui hp;Neostrata aha gel;Neostrata hq;Nuquin hp;Pigmanorm;Porcelana;Sinquin;Solaquin forte sun bleaching;Superfade age spot;Ultraquin plaine.

World Health Organization (WHO)

Hydroquinone was introduced in 1965 as a topical depigmenting agent for hyperpigmentation. At high concentrations hydroquinone is corrosive and in most countries has been restricted to the level of approximately 2% and limited to the period of less than 2 months. Additional consideration for restrictive action is that animal experiments have also demonstrated carcinogenic and mutagenic potential of hydroquinone.

General Description

Light colored crystals or solutions. May irritate the skin, eyes and mucous membranes. Mildly toxic by ingestion or skin absorption.

Environmental fate

Biological. In activated sludge, 7.5% mineralized to carbon dioxide after 5 d (Freitag et al., 1985). Under methanogenic conditions, inocula from a municipal sewage treatment plant digester degraded hydroquinone to phenol prior to being mineralized to carbon dioxide and methane (Young and Rivera, 1985). In various pure cultures, hydroquinone degraded to the following intermediates: benzoquinone, 2-hydroxy-1,4-benzoquinone, and β-ketoadipic acid. Hydroquinone also degraded in activated sludge but no products were identified (Harbison and Belly, 1982). Heukelekian and Rand (1955) reported a 5-d BOD value of 0.74 g/g which is 39.2% of the ThOD value of 1.89 g/g. In activated sludge inoculum, following a 20-d adaptation period, 90.0% COD removal was achieved. The average rate of biodegradation was 54.2 mg COD/g?h (Pitter, 1976). Photolytic. A carbon dioxide yield of 53.7% was achieved when hydroquinone adsorbed on silica gel was irradiated with light (λ >290 nm) for 17 h (Freitag et al., 1985). Chemical/Physical. Ozonolysis products reported are p-quinone and dibasic acids (Verschueren, 1983). Moussavi (1979) studied the autoxidation of hydroquinone in slightly alkaline (pH 7 to 9) aqueous solutions at room temperature. The oxidation of hydroquinone by oxygen followed first-order kinetics that yielded hydrogen peroxide and p-quinone as products. At pH values of 7.0, 8.0, and 9.0, the calculated half-lives of this reaction were 111, 41, and 0.84 h, respectively (Moussavi, 1979). Chlorine dioxide reacted with hydroquinone in an aqueous solution forming p-benzoquinone (Wajon et al., 1982). Kanno et al. (1982) studied the aqueous reaction of hydroquinone and other substituted aromatic hydrocarbons (aniline, toluidine, 1- and 2-naphthylamine, phenol, cresol, pyrocatechol, resorcinol, and 1-naphthol) with hypochlorous acid in the presence of ammonium ion. They reported that the aromatic ring was not chlorinated as expected but was cleaved by chloramine forming cyanogen chloride. As the pH was lowered, the amount of cyanogen chloride formed increased (Kanno et al., 1982). At influent concentrations of 1.0, 0.1, 0.01, and 0.001 mg/L, the GAC adsorption capacities were 160, 90, 51, and 29 mg/g, respectively (Dobbs and Cohen, 1980).

Contact allergens

Hydroquinone is used in photography developers (black and white, X-ray, and microfilms), in plastics, in hair dyes as an antioxidant and hair colorant. Hydroquinone is found in many skin bleaching creams.

Uses

Use as photographic reducer and developer; as reagent in the determination of small quantities of phosphate; as antioxidant. Depigmentor

Uses

Photographic reducer and developer; antioxidant; stabilizing agent for some polymers; intermediate in the manufacturing of some dyes and pigments; in cosmetic formulations.

Therapeutic Function

Depigmentor

Fire Hazard

Dust cloud may explode if ignited in an enclosed area. Hydroquinone can react with oxidizing materials and is rapidly oxidized in the presence of alkaline materials. Oxidizes in air.

Reactivity Profile

Hydroquinone is a slight explosion hazard when exposed to heat. Incompatible with strong oxidizing agents. Also incompatible with bases. Hydroquinone reacts with oxygen and sodium hydroxide. Reacts with ferric salts . Hot and/or concentrated NaOH can cause Hydroquinone to decompose exothermically at elevated temperature. (NFPA Pub. 491M, 1975, 385)

Air & Water Reactions

Darkens on exposure to air and light. Miscible in water. Solutions become brown in air due to oxidation. Oxidation is very rapid in the presence of alkali.

Originator

Quinnone,Dermohr,US,1980

Health Hazard

Hydroquinone is very toxic; the probable oral lethal dose for humans is 50-500 mg/kg, or between 1 teaspoon and 1 ounce for a 150 lb. person. It is irritating but not corrosive. Fatal human doses have ranged from 5-12 grams, but 300-500 mg have been ingested daily for 3-5 months without ill effects. Death is apparently initiated by respiratory failure or anoxia.

Source

Hydroquinone occurs naturally in strawberry tree leaves, pears, blackberries, Chinese alpenrose, bilberries, blackberries, hyacinth flowers, anise, cowberries, and lingonberries (Duke, 1992).

Clinical Use

Hydroquinone is applied topically to treat disorders characterized by excessive melanin in the epidermis, such as melasma. In the United States, nonprescription skin-lightening products contain hydroquinone at concentrations of 2% or less; higher concentrations are available by prescription.

Production Methods

There are three current manufacturing processes for HQ: oxidative cleavage of diisopropylbenzene, oxidation of aniline, and hydroxylation of phenol. Diisopropylbenzene is air oxidized to the intermediate diisopropylbenzene bishydroperoxide. This hydroperoxide is purified by extraction and reacted further to form hydroquinone. The purified product is isolated by filtration and packaged. The process can be almost entirely closed, continuous, computer-controlled, and monitored. HQcan also be prepared by oxidizing aniline to quinone in the presence of manganese dioxide and sulfuric acid. p-Benzoquinone is then reduced to HQ using iron oxide. The resulting hydroquinone is crystallized and dried. The process occurs in a closed system. HQis also manufactured by hydroxylation of phenol using hydrogen peroxide as a hydroxylation agent. The reaction is catalyzed by strong mineral acids or ferrous or cobalt salts.

Manufacturing Process

Into a pressure reactor there was charged 100 ml of methanol and 1 g of diruthenium nonacarbonyl. The reactor was closed, cooled in solid carbon dioxide/acetone, and evacuated. Acetylene, to the extent of 1 mol (26 g), was metered into the cold reactor. Carbon monoxide was then pressured into this vessel at 835-980 atmospheres, during a period of 16.5 hours; while the reactor was maintained at 100°C to 150°C. The reactor was then cooled to room temperature and opened. The reaction mixture was removed from the vessel and distilled at a pressure of 30-60 mm, and a bath temperature of 30°C to 50°C until the methanol had all been removed. The extremely viscous tarry residue remaining in the still pot was given a very crude distillation, the distillate boiling at 82°C to 132°C/2 mm. In an attempt to purify this distillate by a more careful distillation, 5.3 g of a liquid distilling from 53°C to 150°C/5 mm was collected. At this point, much solid sublimate was noted not only in this distillate but in the condenser of the still. 7 g of the solid sublimate was scraped out of the condenser of the still. Recrystallization of the sublimate from ethyl acetate containing a small amount of petroleum ether gave beautiful crystals melting at 175°C to 177°C (5 g). Infrared analysis confirmed that this compound was hydroquinone (9% conversion).

Uses

hydroquinone is a pigment-lightening agent used in bleaching creams. Hydroquinone combines with oxygen very rapidly and becomes brown when exposed to air. Although it occurs naturally, the synthetic version is the one commonly used in cosmetics. Application to the skin may cause allergic reaction and increase skin sun sensitivity. Hydroquinone is potentially carcinogenic and is associated with causing ochronosis, a discoloration of the skin. The u.S. FDA has banned hydroquinone from oTC cosmetic formulations, but allows 4 percent in prescription products. Its use in cosmetics is prohibited in some european countries and in Australia.

Uses

reducing agent prevents polymerization of resin monomers lightens darkened skin, light sensitive

Purification Methods

Crystallise quinol from acetone, *benzene, EtOH, EtOH/*benzene, water or acetonitrile (25g in 30mL), preferably under nitrogen. Dry it under vacuum. [Wolfenden et al. J Am Chem Soc 109 463 1987, Beilstein 6 H 836, 6 IV 5712.]

Physical properties

Colorless to pale brown, odorless, hexagonal crystals

Definition

ChEBI: A benzenediol comprising benzene core carrying two hydroxy substituents para to each other.

Uses

K channel agonist, antihypertensive

Carcinogenicity

No case reports of cancer associated with HQ exposure have been published.

Chemical Properties

white needle-like crystals or crystalline powder

Health Hazard

Exposures to hydroquinone in large quantities by accidental oral ingestion produce toxicity and poisoning. The symptoms of poisoning include, but are not limited to, blurred speech, tinnitus, tremors, sense of suffocation, vomiting, muscular twitching, headache, convul- sions, dyspnea and cyanosis from methemoglobinemia, coma, and collapse from respira- tory failure. Occupational workers should be allowed to work with protective clothing and dust masks with full-face or goggles to protect the eyes, and under proper management.

Synthesis Reference(s)

Chemistry Letters, 14, p. 731, 1985The Journal of Organic Chemistry, 50, p. 1722, 1985Tetrahedron Letters, 22, p. 2337, 1981 DOI: 10.1016/S0040-4039(01)82900-2

Chemical Properties

Hydroquinone, a colorless, hexagonal prism, has been reported to be a good antimitotic and tumor-inhibiting agent. It is a reducing agent used in a photographic developer, which polymerizes in the presence of oxidizing agents. In the manufacturing industry it may occur include bacteriostatic agent, drug, fur processing, motor fuel, paint, organic chemicals, plastics, stone coating, and styrene monomers.

Indications

Hydroquinone interferes with the production of the pigment melanin by epidermal melanocytes through at least two mechanisms: it competitively inhibits tyrosinase, one of the principal enzymes responsible for converting tyrosine to melanin, and it selectively damages melanocytes and melanosomes (the organelles within which melanin is stored).

Hazard

Toxic by ingestion and inhalation, irritant. Questionable carcinogen.

Side effects

The incidence of adverse effects with hydroquinone increases in proportion to its concentration. A relatively common side effect is local irritation, which may actually exacerbate the discoloration of the skin being treated. Allergic contact dermatitis occurs less commonly. A rare but more serious complication is exogenous ochronosis, in which a yellow-brown pigment deposited in the dermis results in blue-black pigmentation of the skin that may be permanent.
InChI:InChI=1/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H

123-31-9 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (H0186)  Hydroquinone  >99.0%(T) 123-31-9 25g 115.00CNY Detail
TCI America (H0186)  Hydroquinone  >99.0%(T) 123-31-9 500g 280.00CNY Detail
Alfa Aesar (A11411)  Hydroquinone, 99%    123-31-9 250g 226.0CNY Detail
Alfa Aesar (A11411)  Hydroquinone, 99%    123-31-9 1000g 658.0CNY Detail
Alfa Aesar (A11411)  Hydroquinone, 99%    123-31-9 5000g 2326.0CNY Detail
Sigma-Aldrich (74347)  Hydroquinone  certified reference material, TraceCERT® 123-31-9 74347-100MG 992.16CNY Detail
Sigma-Aldrich (PHR1469)  Hydroquinone  secondary pharmaceutical standard; traceable to USP 123-31-9 PHR1469-1G 791.15CNY Detail
USP (1324002)  Hydroquinone  United States Pharmacopeia (USP) Reference Standard 123-31-9 1324002-500MG 4,662.45CNY Detail

123-31-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name hydroquinone

1.2 Other means of identification

Product number -
Other names 1,4-benzenediol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Hydroquinone is used as a developing agent in black-and-white photography, lithography, and x-ray films. It is also used as an intermediate to produce antioxidants for rubber and food. It is added to a number of industrial monomers to inhibit polymerization during shipping, storage, and processing.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:123-31-9 SDS

123-31-9Synthetic route

p-benzoquinone
106-51-4

p-benzoquinone

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
With nickel In tetrahydrofuran at 20℃; for 0.166667h; Reduction;100%
With boron trifluoride diethyl etherate; sodium iodide In acetonitrile at 0℃; for 0.0833333h;99%
With hydrazine hydrate In acetonitrile at 20℃; for 18h; Irradiation;99%
4-Benzyloxyphenol
103-16-2

4-Benzyloxyphenol

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 50℃; under 750.075 Torr; Reagent/catalyst; Flow reactor;100%
With hydrogen In methanol at 20℃; under 760.051 Torr; for 18h; Reagent/catalyst; chemoselective reaction;100%
With hydrogen In methanol at 20℃; for 6h; chemoselective reaction;100%
Multi-step reaction with 3 steps
1: potassium carbonate, potassium iodide / acetonitrile / 1 h / Heating
2: 84 percent / hydrogen / 10percent palladium on carbon / tetrahydrofuran; ethanol / 3 h / 760 Torr
3: 88 percent / hydrogen / 10percent palladium on carbon / ethanol / 15 h / 3040 Torr
View Scheme
With formic acid for 3h; Heating / reflux;
1,4-dibenzyloxybenzene
621-91-0

1,4-dibenzyloxybenzene

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
With hydrogen In tetrahydrofuran; carbon dioxide at 50℃; under 75007.5 Torr; gas-expanded solution;100%
dimethanesulfonate hydroquinone
126150-65-0

dimethanesulfonate hydroquinone

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
With sodium phosphate In aq. phosphate buffer; water; dimethyl sulfoxide at 25℃; for 0.333333h; pH=7.5; Enzymatic reaction;100%
1,4-dimethoxybezene
150-78-7

1,4-dimethoxybezene

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
With hydrogenchloride In water at 250℃; under 37503.8 Torr; for 3h; Autoclave; Inert atmosphere; Green chemistry;98%
With hydrogen iodide at 25℃; for 24h; Inert atmosphere;96%
With lithium triethylborohydride In tetrahydrofuran at 67℃; for 168h;90%
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
With dihydrogen peroxide at 20℃; for 0.666667h; Dakin Phenol Oxidation; Green chemistry;98%
With dihydrogen peroxide In water at 20℃; for 2h; Dakin Phenol Oxidation; Green chemistry;98%
With dihydrogen peroxide; 5-ethyl-10-methyl-2,4-dioxo-2,3,4,10-tetrahydrobenzo[g]pteridin-5-ium perchlorate; sodium hydrogencarbonate In methanol; water at 20℃; for 24h; Reagent/catalyst; Dakin Phenol Oxidation; chemoselective reaction;97%
hydrazine hydroquinone complex
97108-34-4

hydrazine hydroquinone complex

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

A

bis(4-hydroxybenzylidene)hydrazine
5466-23-9

bis(4-hydroxybenzylidene)hydrazine

B

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
at 25 - 30℃; for 1h; Product distribution; Further Variations:; Reaction partners; Reaction types; Condensation; solid state, in ball mill;A 98%
B n/a
(p-hydroxyphenyl)boronic acid
71597-85-8

(p-hydroxyphenyl)boronic acid

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
With 2,5-dimethylfuran; zinc(II) phthalocyanine; oxygen In tetrahydrofuran at 25℃; under 760.051 Torr; for 1.5h; Irradiation; Sealed tube; Schlenk technique;98%
With 1-carboxymethyl-3-methylimidazolium tetrachloroferrate; dihydrogen peroxide In neat (no solvent) at 20℃; for 0.116667h;95%
With iron(III) oxide; oxygen In tetrahydrofuran Irradiation;91%
1,4-bis(trimethylsilyloxy)benzene
2117-24-0

1,4-bis(trimethylsilyloxy)benzene

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0833333h; Green chemistry;98%
p-benzoquinone
106-51-4

p-benzoquinone

2-mesitylmagnesium bromide
2633-66-1

2-mesitylmagnesium bromide

A

4-hydroxy-4-(2,4,6-trimethylphenyl)-2,5-cyclohexadiene

4-hydroxy-4-(2,4,6-trimethylphenyl)-2,5-cyclohexadiene

B

hydroquinone
123-31-9

hydroquinone

C

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
In tetrahydrofuran Grignard reaction;A 97%
B 3%
C 4%
p-Coumaric Acid
7400-08-0

p-Coumaric Acid

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
With NADH In aq. phosphate buffer at 37℃; for 8h; pH=7.0; Enzymatic reaction;97%
Multi-step reaction with 3 steps
1.1: feruloyl-CoA synthetase / Enzymatic reaction
1.2: Enzymatic reaction
2.1: vanillin dehydrogenase from genom of Pseudomonas putida KT2440 (NC_002947.4) / Enzymatic reaction
3.1: 4-hydroxybenzoate 1-hydroxylase MNX1 from yeast Candida parapsilosis strain CDC317 / 2 h / Enzymatic reaction
View Scheme
Multi-step reaction with 3 steps
1: E. coli (pET28a-TtAdo-BLPad) / aq. phosphate buffer / 6 h / 37 °C / pH 7.0 / Enzymatic reaction
2: vanillin dehydrogenase from genom of Pseudomonas putida KT2440 (NC_002947.4) / Enzymatic reaction
3: 4-hydroxybenzoate 1-hydroxylase MNX1 from yeast Candida parapsilosis strain CDC317 / 2 h / Enzymatic reaction
View Scheme
Multi-step reaction with 4 steps
1: Bacillus licheniformis strain CGMCC 7172 phenolic acid decarboxylase / 6 h / Enzymatic reaction
2: oxygen; Thielavia terrestris NRRL 8126 aromatic dioxygenase TtAdo (XP_003653923) / 37 °C / pH 7.0 / Enzymatic reaction
3: vanillin dehydrogenase from genom of Pseudomonas putida KT2440 (NC_002947.4) / Enzymatic reaction
4: 4-hydroxybenzoate 1-hydroxylase MNX1 from yeast Candida parapsilosis strain CDC317 / 2 h / Enzymatic reaction
View Scheme
sec.-butyllithium
598-30-1

sec.-butyllithium

p-benzoquinone
106-51-4

p-benzoquinone

A

hydroquinone
123-31-9

hydroquinone

B

4-sec-Butyl-4-hydroxy-cyclohexa-2,5-dienone

4-sec-Butyl-4-hydroxy-cyclohexa-2,5-dienone

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; for 0.5h;A 96%
B 4%
1,4-Phenyldiboronic acid
4612-26-4

1,4-Phenyldiboronic acid

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
With urea hydrogen peroxide adduct In methanol at 27 - 29℃; for 0.0833333h; Green chemistry; chemoselective reaction;96%
With LACTIC ACID; dihydrogen peroxide In water at 20℃; for 0.166667h; Reagent/catalyst; Green chemistry;95%
With dihydrogen peroxide In ethanol at 20℃; for 0.166667h;91%
benzene
71-43-2

benzene

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
With dihydrogen peroxide; copper(II) nitrate In phosphate buffer; acetonitrile at 50℃; Oxidation;95%
With dihydrogen peroxide; vanadia In water; acetic acid; acetonitrile at 59.84℃; for 6h; Green chemistry;4.1%
With ethanol; sulfuric acid Electrolysis;
1,4-bis{[(tert-butyl)(dimethyl)silyl]oxy}benzene
78018-57-2

1,4-bis{[(tert-butyl)(dimethyl)silyl]oxy}benzene

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
With aluminium(III) chloride hexahydrate In methanol at 50℃; for 12h; Solvent; Temperature; Heating; Sealed tube; chemoselective reaction;95%
With cerium (IV) sulfate tetrahydrate In methanol at 130℃; for 0.333333h; Microwave irradiation;93%
With dichloro bis(acetonitrile) palladium(II) In water; acetone at 75℃; for 19h;79%
With potassium hydrogen difluoride In methanol at 20℃; for 1h;67%
With copper(ll) sulfate pentahydrate In methanol at 100℃; for 0.25h; Microwave irradiation;64%
p-benzoquinone
106-51-4

p-benzoquinone

CH3MgX

CH3MgX

A

4-hydroxy-4-methyl-cyclohexa-2,5-dienone
23438-23-5

4-hydroxy-4-methyl-cyclohexa-2,5-dienone

B

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; for 0.5h;A 95%
B n/a
p-benzoquinone
106-51-4

p-benzoquinone

(C2H5)(CH3)CHMgX

(C2H5)(CH3)CHMgX

A

hydroquinone
123-31-9

hydroquinone

B

4-sec-Butyl-4-hydroxy-cyclohexa-2,5-dienone

4-sec-Butyl-4-hydroxy-cyclohexa-2,5-dienone

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; for 0.5h;A 95%
B 5%
phenylmagnesium bromide

phenylmagnesium bromide

p-benzoquinone
106-51-4

p-benzoquinone

A

4-hydroxy-4-phenyl-cyclohexa-2,5-dienone
42860-77-5

4-hydroxy-4-phenyl-cyclohexa-2,5-dienone

B

hydroquinone
123-31-9

hydroquinone

C

benzene
71-43-2

benzene

Conditions
ConditionsYield
In tetrahydrofuran Grignard reaction;A 94%
B 3%
C 3%
phenol
108-95-2

phenol

A

maleic anhydride
108-31-6

maleic anhydride

B

succinic acid
110-15-6

succinic acid

C

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
With sulfuric acid; water; oxygen; titanium silicalite 1 (TS-1) at 65℃; for 4 - 6h; pH=~ 1.2 - 1.8; Product distribution / selectivity; Electrolysis;A n/a
B n/a
C 93.4%
4-isopropenylphenol
4286-23-1

4-isopropenylphenol

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
93.3%
With hydrogenchloride; dihydrogen peroxide at 20 - 40℃; for 0.583333h; Product distribution; other alkenyl phenols;91%
With sulfuric acid; dihydrogen peroxide; sodium sulfite In acetone
4-methoxy-phenol
150-76-5

4-methoxy-phenol

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
With Cyclohexyl iodide In N,N-dimethyl-formamide for 3h; Product distribution; Further Variations:; Reagents; Solvents; Temperatures; time; Heating;93%
With water; hydrogen bromide; Aliquat 336 at 105℃; for 7h; Catalytic behavior;85%
With 1-butylpyridinium bromide at 100℃; Microwave irradiation; Neat (no solvent);77%
cyclohexylamine
108-91-8

cyclohexylamine

(1-butyl)-(-4-oxy-phenylene) carbonate
81577-19-7

(1-butyl)-(-4-oxy-phenylene) carbonate

A

butyl N-cyclohexylcarbamate
17671-80-6

butyl N-cyclohexylcarbamate

B

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
With N,N-dimethyl-formamideA 92%
B n/a
4-(1-cyclopenten-1-yl)phenol
877-46-3

4-(1-cyclopenten-1-yl)phenol

A

cyclopentanone
120-92-3

cyclopentanone

B

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
With hydrogenchloride; dihydrogen peroxide In acetonitrile at 50℃; for 3h; the excess of H2O2 was removed by catalytic hydrogenation using 10percent Pd-C;A n/a
B 91.6%
p-benzoquinone
106-51-4

p-benzoquinone

(CH3)2CHMgX

(CH3)2CHMgX

A

hydroquinone
123-31-9

hydroquinone

B

4-hydroxy-4-isopropylcyclohexa-2,5-dien-1-one

4-hydroxy-4-isopropylcyclohexa-2,5-dien-1-one

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; for 0.5h;A 90%
B 10%
p-benzoquinone
106-51-4

p-benzoquinone

A

hydroquinone
123-31-9

hydroquinone

B

phenol
108-95-2

phenol

Conditions
ConditionsYield
With cyclohexanone; cyclohexanol at 115℃; for 9h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere;A 90%
B 4.3 g
methyl 5-phenylcyclohexane-1,3-dione
18986-66-8

methyl 5-phenylcyclohexane-1,3-dione

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
With iodine; dimethyl sulfoxide at 80℃; for 24h; Sealed tube; Green chemistry;90%
acetic anhydride
108-24-7

acetic anhydride

hydroquinone
123-31-9

hydroquinone

benzene-1,4-diyl diacetate
1205-91-0

benzene-1,4-diyl diacetate

Conditions
ConditionsYield
With magnesium(II) perchlorate at 20℃; for 0.16h;100%
With tin(IV) tetraphenylporphyrin perchlorate at 20℃; for 0.0833333h;99%
beta zeolite H-form at 20℃; for 2h;99%
hydroquinone
123-31-9

hydroquinone

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With barium ferrate(VI) In benzene for 0.25h; Product distribution; Heating;100%
With benzyltrimethylammonium tribromide; sodium acetate In dichloromethane; water for 2h; Ambient temperature;100%
With bis(2,2'-bipyridyl) copper(II) permanganate In dichloromethane for 0.25h; Ambient temperature;100%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

hydroquinone
123-31-9

hydroquinone

2-(4-(tetrahydro-2H-pyran-2-yloxy)phenoxy)tetrahydro-2H-pyran
2139-44-8

2-(4-(tetrahydro-2H-pyran-2-yloxy)phenoxy)tetrahydro-2H-pyran

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane for 3h;100%
With pyridinium p-toluenesulfonate In dichloromethane at 25℃; for 2h;100%
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 48h;99%
propargyl bromide
106-96-7

propargyl bromide

hydroquinone
123-31-9

hydroquinone

1,4-bis(prop-2-yn-1-yloxy)benzene
34596-36-6

1,4-bis(prop-2-yn-1-yloxy)benzene

Conditions
ConditionsYield
Stage #1: hydroquinone With potassium carbonate In acetone for 0.5h; Reflux;
Stage #2: propargyl bromide In acetone for 12h; Reflux;
100%
Stage #1: hydroquinone With 18-crown-6 ether; potassium carbonate In acetonitrile for 0.5h; Reflux; Inert atmosphere;
Stage #2: propargyl bromide In toluene; acetonitrile Reflux; Inert atmosphere;
98%
Stage #1: hydroquinone With potassium carbonate In acetone for 0.5h;
Stage #2: propargyl bromide In acetone for 20h; Reflux;
96%
2-[2-(chloroethoxy)ethoxy]ethanol
5197-62-6

2-[2-(chloroethoxy)ethoxy]ethanol

hydroquinone
123-31-9

hydroquinone

1,4-bis-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)benzene
134881-72-4

1,4-bis-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)benzene

Conditions
ConditionsYield
With potassium tert-butylate In tert-butyl alcohol for 92h; Heating;100%
With potassium tert-butylate In tert-butyl alcohol for 65h; Heating;78%
With potassium carbonate In acetonitrile at 130℃; for 72h; Sealed tube; High pressure;75%
pentafluorosulfanyl isocyanate
2375-30-6

pentafluorosulfanyl isocyanate

hydroquinone
123-31-9

hydroquinone

1,4-Phenylene Bis<(pentafluorosulfanyl)carbamate>
90597-97-0

1,4-Phenylene Bis<(pentafluorosulfanyl)carbamate>

Conditions
ConditionsYield
In acetone -196 deg C to r.t.;100%
C14H20O4
134637-27-7

C14H20O4

hydroquinone
123-31-9

hydroquinone

C20H24O6
134637-24-4

C20H24O6

Conditions
ConditionsYield
With silver(l) oxide Ambient temperature;100%
hydroquinone
123-31-9

hydroquinone

A

diphenyl-2,5 furannedicarbaldehyde 3,4
36831-87-5

diphenyl-2,5 furannedicarbaldehyde 3,4

B

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With barium ferrate(VI) In benzene for 0.3h; Heating;A 70%
B 100%
3,5-dibenzyloxylbenzoyl chloride
28917-44-4

3,5-dibenzyloxylbenzoyl chloride

hydroquinone
123-31-9

hydroquinone

C48H38O8
159507-52-5

C48H38O8

Conditions
ConditionsYield
With dmap In dichloromethane for 120h; Ambient temperature;100%
bis(diethylamino)phenylphosphine
1636-14-2

bis(diethylamino)phenylphosphine

hydroquinone
123-31-9

hydroquinone

p-phenylene bis(N,N-diethyl-P-phenylphosphonamidite)

p-phenylene bis(N,N-diethyl-P-phenylphosphonamidite)

Conditions
ConditionsYield
at 115 - 120℃; for 2.5h;100%
In acetonitrile
2,3-dihydroxynaphthalene-6-sulphonic acid sodium salt
135-53-5

2,3-dihydroxynaphthalene-6-sulphonic acid sodium salt

hydroquinone
123-31-9

hydroquinone

1,3-bis(4'-fluorobenzoyl)benzene
108464-88-6

1,3-bis(4'-fluorobenzoyl)benzene

Polymer; Monomer(s): 1,3-bis(4-fluorobenzoyl)benzene, 5 mmol; sodium 6,7-dihydroxy-2-naphthalenesulfonate, 4.5 mmol; hydroquinone, 0.5 mmol

Polymer; Monomer(s): 1,3-bis(4-fluorobenzoyl)benzene, 5 mmol; sodium 6,7-dihydroxy-2-naphthalenesulfonate, 4.5 mmol; hydroquinone, 0.5 mmol

Conditions
ConditionsYield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 160 - 170℃;100%
2,3-dihydroxynaphthalene-6-sulphonic acid sodium salt
135-53-5

2,3-dihydroxynaphthalene-6-sulphonic acid sodium salt

hydroquinone
123-31-9

hydroquinone

1,3-bis(4'-fluorobenzoyl)benzene
108464-88-6

1,3-bis(4'-fluorobenzoyl)benzene

Polymer; Monomer(s): 1,3-bis(4-fluorobenzoyl)benzene, 5 mmol; sodium 6,7-dihydroxy-2-naphthalenesulfonate, 4 mmol; hydroquinone, 1 mmol

Polymer; Monomer(s): 1,3-bis(4-fluorobenzoyl)benzene, 5 mmol; sodium 6,7-dihydroxy-2-naphthalenesulfonate, 4 mmol; hydroquinone, 1 mmol

Conditions
ConditionsYield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 160 - 170℃;100%
2,3-dihydroxynaphthalene-6-sulphonic acid sodium salt
135-53-5

2,3-dihydroxynaphthalene-6-sulphonic acid sodium salt

hydroquinone
123-31-9

hydroquinone

1,3-bis(4'-fluorobenzoyl)benzene
108464-88-6

1,3-bis(4'-fluorobenzoyl)benzene

Polymer; Monomer(s): 1,3-bis(4-fluorobenzoyl)benzene, 5 mmol; sodium 6,7-dihydroxy-2-naphthalenesulfonate, 3.5 mmol; hydroquinone, 1.5 mmol

Polymer; Monomer(s): 1,3-bis(4-fluorobenzoyl)benzene, 5 mmol; sodium 6,7-dihydroxy-2-naphthalenesulfonate, 3.5 mmol; hydroquinone, 1.5 mmol

Conditions
ConditionsYield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 160 - 170℃;100%
2,3-dihydroxynaphthalene-6-sulphonic acid sodium salt
135-53-5

2,3-dihydroxynaphthalene-6-sulphonic acid sodium salt

hydroquinone
123-31-9

hydroquinone

1,3-bis(4'-fluorobenzoyl)benzene
108464-88-6

1,3-bis(4'-fluorobenzoyl)benzene

Polymer; Monomer(s): 1,3-bis(4-fluorobenzoyl)benzene, 5 mmol; sodium 6,7-dihydroxy-2-naphthalenesulfonate, 3 mmol; hydroquinone, 2 mmol

Polymer; Monomer(s): 1,3-bis(4-fluorobenzoyl)benzene, 5 mmol; sodium 6,7-dihydroxy-2-naphthalenesulfonate, 3 mmol; hydroquinone, 2 mmol

Conditions
ConditionsYield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 160 - 170℃;100%
2,3-dihydroxynaphthalene-6-sulphonic acid sodium salt
135-53-5

2,3-dihydroxynaphthalene-6-sulphonic acid sodium salt

hydroquinone
123-31-9

hydroquinone

1,3-bis(4'-fluorobenzoyl)benzene
108464-88-6

1,3-bis(4'-fluorobenzoyl)benzene

Polymer; Monomer(s): 1,3-bis(4-fluorobenzoyl)benzene, 5 mmol; sodium 6,7-dihydroxy-2-naphthalenesulfonate, 2.5 mmol; hydroquinone, 2.5 mmol

Polymer; Monomer(s): 1,3-bis(4-fluorobenzoyl)benzene, 5 mmol; sodium 6,7-dihydroxy-2-naphthalenesulfonate, 2.5 mmol; hydroquinone, 2.5 mmol

Conditions
ConditionsYield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 160 - 170℃;100%
6-chloro-2-(2,6-diisopropylphenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
852282-88-3

6-chloro-2-(2,6-diisopropylphenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

hydroquinone
123-31-9

hydroquinone

C30H27NO4
923584-43-4

C30H27NO4

Conditions
ConditionsYield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 24h;100%
hydroquinone
123-31-9

hydroquinone

1,1,3,3-tetramethyldisilazane
15933-59-2

1,1,3,3-tetramethyldisilazane

1,4-bis(dimethylsilyloxy)benzene
70939-99-0

1,4-bis(dimethylsilyloxy)benzene

Conditions
ConditionsYield
With dimethylmonochlorosilane In tetrahydrofuran Reflux;100%
hydroquinone
123-31-9

hydroquinone

tert-butyl alcohol
75-65-0

tert-butyl alcohol

tert-butylhydroquinone
1948-33-0

tert-butylhydroquinone

Conditions
ConditionsYield
With phosphoric acid In water at 59 - 81℃; for 2h; Temperature;99.9%
With aminosulfonic acid In 1,4-dioxane; toluene at 135℃; for 8h; Temperature;50%
With phosphoric acid In water at 80℃; for 4h; Concentration; Temperature; Time; Large scale;44.8%
acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

hydroquinone
123-31-9

hydroquinone

tert-butylhydroquinone
1948-33-0

tert-butylhydroquinone

Conditions
ConditionsYield
With sulfuric acid at 85℃; for 8h; Temperature; Large scale;99.9%
oxirane
75-21-8

oxirane

hydroquinone
123-31-9

hydroquinone

1,4-bis(2-hydroxyethoxy)benzene
104-38-1

1,4-bis(2-hydroxyethoxy)benzene

Conditions
ConditionsYield
Stage #1: hydroquinone With 1,1'-bis-(diphenylphosphino)ferrocene In diethylene glycol dimethyl ether at 100℃; Autoclave; Inert atmosphere;
Stage #2: oxirane In diethylene glycol dimethyl ether at 130 - 135℃; for 4h; Solvent; Temperature;
99.3%
anion exchange resin A (Cl-type) In 2-methoxy-ethanol; toluene at 100℃; for 6h;73%
anion exchange resin A (Cl-type) In 2-methoxy-ethanol at 100℃; for 4.5h;69 %Chromat.
2-bromoisobutyric acid bromide
20769-85-1

2-bromoisobutyric acid bromide

hydroquinone
123-31-9

hydroquinone

1,4-phenylene bis(2-bromo-2-methylpropanoate)

1,4-phenylene bis(2-bromo-2-methylpropanoate)

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 6.5h; Cooling with ice;99.2%
With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;86.8%
With triethylamine In tetrahydrofuran for 24h;
hydroquinone
123-31-9

hydroquinone

1,4-Cyclohexanediol
556-48-9

1,4-Cyclohexanediol

Conditions
ConditionsYield
With hydrogen In water at 30℃; under 7500.75 Torr; for 7h; Autoclave;99.1%
With hydrogen In water at 80℃; under 15001.5 Torr; for 6h;99%
With potassium hydroxide; samarium diiodide In tetrahydrofuran; water for 0.05h; Ambient temperature;98%
acetic acid
64-19-7

acetic acid

hydroquinone
123-31-9

hydroquinone

benzene-1,4-diyl diacetate
1205-91-0

benzene-1,4-diyl diacetate

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate for 1h; Heating;99%
With poly(4-vinylpyridine) perchlorate In neat (no solvent) at 20℃; for 0.366667h;92%
With PPA
allyl bromide
106-95-6

allyl bromide

hydroquinone
123-31-9

hydroquinone

1,4-bis(allyloxy)benzene
37592-20-4

1,4-bis(allyloxy)benzene

Conditions
ConditionsYield
Stage #1: allyl bromide With sodium hydride In N,N-dimethyl-formamide; oil at -10℃; for 0.166667h;
Stage #2: hydroquinone In N,N-dimethyl-formamide; oil for 0.75h;
99%
With potassium carbonate In acetone for 5h; Heating;95%
With potassium carbonate In acetone Reflux;90%

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