2-Bromohydroquinone supplier

Name
BROMOHYDROQUINONE
EINECS 209-516-2
CAS No. 583-69-7
Article Data53
CAS DataBase
Density 1.844 g/cm³
Solubility
Melting Point 112-116 °C(lit.)
Formula C₆H₅BrO₂
Boiling Point 278.3 °C at 760 mmHg
Molecular Weight 189.008
Flash Point 122.1 °C
Transport Information
Appearance beige to brown fine crystalline powder
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Hydroquinone,bromo- (6CI,7CI,8CI);1-Bromo-2,5-dihydroxybenzene;2-Bromo-1,4-benzenediol;2-Bromo-1,4-dihydroxybenzene;2-Bromo-1,4-hydroquinone;2-Bromohydroquinone;2-Bromoquinol;Bromohydroquinone;NSC 3977;
PSA 40.46000
LogP 1.86030

Synthetic route

: 123-31-9
hydroquinone

: 583-69-7
2-bromobenzene-1,4-diol

Conditions

Conditions	Yield
With dihydrogen peroxide; potassium bromide In water; acetonitrile	97%
With o-xylylene bis(triethylammonium tribromide) In acetonitrile at 20℃; for 0.0833333h; regioselective reaction;	97%
With bromine In chloroform at 0 - 25℃; for 3.25h;	92%

: 3958-82-5
2-bromo-1,4-benzoquinone

: 583-69-7
2-bromobenzene-1,4-diol

Conditions

Conditions	Yield
With sodium azide In water; acetone at 20℃;	95%
With 1,4-dihydronicotinamide adenine dinucleotide In water; acetonitrile at 30℃; Rate constant; pH=7.0;

: 52376-16-6
2-bromo-1,4-phenylene diacetate

: 583-69-7
2-bromobenzene-1,4-diol

Conditions

Conditions	Yield
With sodium hydroxide for 12h; Ambient temperature;	90%
With sodium hydroxide at 20℃;

: 637-88-7
1,4-Cyclohexanedione

: 583-69-7
2-bromobenzene-1,4-diol

Conditions

Conditions	Yield
With oxygen; copper diacetate; trifluoroacetic acid; lithium bromide In acetonitrile at 80℃; under 760.051 Torr; for 10h; Sealed tube;	88%

: 52376-17-7
1,4-O-di-propanoylbromohydroquinone

: 583-69-7
2-bromobenzene-1,4-diol

Conditions

Conditions	Yield
With Candida antarctica lipase B In di-isopropyl ether; isopropyl alcohol at 45℃; for 1h; Enzymatic reaction; regioselective reaction;	86%

: 123-31-9
hydroquinone

A: 583-69-7
2-bromobenzene-1,4-diol

B: 14753-51-6
2,5-dibromohydroquinone

Conditions

Conditions	Yield
With Diethyl 2-bromomalonate at 100℃; for 48h; Product distribution; Further Variations:; Reagents;	A 80% B 11%

: 108-86-1
bromobenzene

A: 5926-51-2
bromomaleic anhydride

B: 591-20-8
3-Bromophenol

C: 95-56-7
2-hydroxybromobenzene

D: 583-69-7
2-bromobenzene-1,4-diol

Conditions

Conditions	Yield
With Fe2(N,N-bis(pyridin-2-ylmethyl)prop-2-yn-1-amine)2(μ2-Cl)2Cl2; dihydrogen peroxide In acetonitrile at 70℃; for 2h;	A 6% B 49% C 29% D 23%

...Expand

: 95-56-7
2-hydroxybromobenzene

: 583-69-7
2-bromobenzene-1,4-diol

Conditions

Conditions	Yield
With ammonium peroxydisulfate
With edetate disodium; L-proline; diothiothreitol In dimethyl sulfoxide; glycerol at 28℃; for 24h; pH=7.2; Microbiological reaction; sodium phosphate buffer;

: 2973-78-6
3-bromo-4-hydroxybenzylaldehyde

: 583-69-7
2-bromobenzene-1,4-diol

Conditions

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide

: 106-34-3
quinhydrone

: 583-69-7
2-bromobenzene-1,4-diol

Conditions

Conditions	Yield
With tetrachloromethane; bromine

: 106-51-4
p-benzoquinone

: 583-69-7
2-bromobenzene-1,4-diol

Conditions

Conditions	Yield
With diethyl ether; hydrogen bromide
With chloroform; hydrogen bromide
With hydrogen bromide

: 106-51-4
p-benzoquinone

A: 583-69-7
2-bromobenzene-1,4-diol

B: 14753-51-6
2,5-dibromohydroquinone

Conditions

Conditions	Yield
With hydrogen bromide

: 150-78-7
1,4-dimethoxybezene

A: 17332-11-5
2-bromo-4-methoxyphenol

B: 583-69-7
2-bromobenzene-1,4-diol

Conditions

Conditions	Yield
With hydrogen bromide; fluorosulphonic acid; lead dioxide 1.)-72 deg C, 3 h; Yield given. Multistep reaction. Yields of byproduct given;

: 60-29-7
diethyl ether

: 67-66-3
chloroform

: 7726-95-6
bromine

: 123-31-9
hydroquinone

: 583-69-7
2-bromobenzene-1,4-diol

...Expand

: 67-66-3
chloroform

: 10035-10-6, 12258-64-9
hydrogen bromide

: 106-51-4
p-benzoquinone

A: 583-69-7
2-bromobenzene-1,4-diol

B: 14753-51-6
2,5-dibromohydroquinone

...Expand

: 7732-18-5
water

: 10035-10-6, 12258-64-9
hydrogen bromide

: 106-51-4
p-benzoquinone

A: 583-69-7
2-bromobenzene-1,4-diol

B: 14753-51-6
2,5-dibromohydroquinone

Conditions

Conditions	Yield
bei laengerer Einwirkung;

...Expand

: 2973-78-6
3-bromo-4-hydroxybenzylaldehyde

: 7722-84-1
dihydrogen peroxide

: furan-2,3,5(4H)-trione pyridine (1:1)

: 583-69-7
2-bromobenzene-1,4-diol

...Expand

: 33851-43-3
3-bromo-2,5-dihydroxy-benzoic acid

: 7732-18-5
water

: 583-69-7
2-bromobenzene-1,4-diol

Conditions

Conditions	Yield
at 160℃; im Rohr;

: 123-31-9
hydroquinone

A: 583-69-7
2-bromobenzene-1,4-diol

B: 106-51-4
p-benzoquinone

Conditions

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 30℃; for 0.2h; UV-irradiation; Title compound not separated from byproducts.;

: 106-51-4
p-benzoquinone

naphthalene-disulfinic acid-(1.5): naphthalene-disulfinic acid-(1.5)

: 583-69-7
2-bromobenzene-1,4-diol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / ZnBr2 / 3 h / 100 °C 2: aq. NaOH / 20 °C View Scheme

: 591-20-8
3-Bromophenol

: 583-69-7
2-bromobenzene-1,4-diol

Conditions

Conditions	Yield
With edetate disodium; L-proline; diothiothreitol In dimethyl sulfoxide; glycerol at 28℃; for 24h; pH=7.2; Microbiological reaction; sodium phosphate buffer;

: 108-86-1
bromobenzene

: 127-17-3
2-oxo-propionic acid

A: 583-69-7
2-bromobenzene-1,4-diol

B: 38739-13-8
(2S)-2-amino-3-(3-bromo-4-hydroxyphenyl)propanoic acid

Conditions

Conditions	Yield
With glucose dehydrogenase; D-glucose; pyridoxal 5'-phosphate; P450 monooxygenase BM3 variant M2; tyrosine phenol lyase mutant M379V; ammonia; oxygen; NADPH; catalase In aq. phosphate buffer; dimethyl sulfoxide at 20℃; for 6h; pH=8; Enzymatic reaction; enantioselective reaction;	A n/a B n/a

...Expand

: 108-86-1
bromobenzene

A: 64-18-6
formic acid

B: 583-69-7
2-bromobenzene-1,4-diol

C: 120-80-9
benzene-1,2-diol

D: 123-31-9
hydroquinone

Conditions

Conditions	Yield
With iron-tungstate oxide capsule; air In water-d2 at 20℃; under 750.075 Torr; for 24h; Electrolysis;

...Expand

: 583-69-7
2-bromobenzene-1,4-diol

: 107-30-2
chloromethyl methyl ether

: 131136-47-5
2-Bromo-1,4-bis(methoxymethoxy)benzene

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;	100%
Stage #1: 2-bromobenzene-1,4-diol With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Stage #2: chloromethyl methyl ether In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 0.5h;	83%
Stage #1: 2-bromobenzene-1,4-diol With ethylmagnesium bromide In tetrahydrofuran; diethyl ether at 20℃; for 1h; Stage #2: chloromethyl methyl ether In tetrahydrofuran; diethyl ether at 20 - 55℃; Further stages.;	81%
With ethylmagnesium bromide 1.) THF, room temperature, 1 h, 2.) 20-25 deg C, overnight, then 50-55 deg C, 1 h; Yield given. Multistep reaction;
With ethylmagnesium bromide 1.) THF, r.t., 6 h; 2.) THF; r.t., 12 h; 50 - 55 degC, 1 h; Yield given. Multistep reaction;

: 75-77-4
chloro-trimethyl-silane

: 583-69-7
2-bromobenzene-1,4-diol

: 67289-10-5
1,4-bis(trimethylsilyloxy)-2-bromobenzene

Conditions

Conditions	Yield
With triethylamine for 1h;	100%

: 583-69-7
2-bromobenzene-1,4-diol

: 3958-82-5
2-bromo-1,4-benzoquinone

Conditions

Conditions	Yield
With oxygen; Nitrogen dioxide In dichloromethane at -10℃; for 10h;	99%
With oxygen; Nitrogen dioxide In dichloromethane at -10℃; for 10h;	99%
With tetrabutylammonium chromate In dichloromethane for 0.5h; Reflux;	99%

: 583-69-7
2-bromobenzene-1,4-diol

: 999-97-3
1,1,1,3,3,3-hexamethyl-disilazane

: 67289-10-5
1,4-bis(trimethylsilyloxy)-2-bromobenzene

Conditions

Conditions	Yield
for 15h; Heating;	99%

: 583-69-7
2-bromobenzene-1,4-diol

: 79271-56-0
Triethylsilyl trifluoromethanesulfonate

: 387400-90-0
2-bromo-1,4-bis-triethylsilanyloxy-benzene

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 0.5h;	98%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃;	98%

: 292638-84-7
styrene

: 583-69-7
2-bromobenzene-1,4-diol

: 34701-63-8
trans-2,5-dihydroxystilbene

Conditions

Conditions	Yield
With palladium diacetate; tetrabutyl-ammonium chloride; sodium carbonate In N,N-dimethyl-formamide at 100℃; for 5h; Heck reaction;	98%

: 592-41-6
1-hexene

: 583-69-7
2-bromobenzene-1,4-diol

: trans-hex-1-enylhydroquinone

Conditions

Conditions	Yield
With palladium diacetate; tetrabutyl-ammonium chloride; sodium carbonate In N,N-dimethyl-formamide at 100℃; for 5h; Heck reaction;	96%

: 583-69-7
2-bromobenzene-1,4-diol

: 108-24-7
acetic anhydride

: 52376-16-6
2-bromo-1,4-phenylene diacetate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	95%

: 583-69-7
2-bromobenzene-1,4-diol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 78018-59-4
1,4-Bis(tert-butyldimethysiloxy)-2-bromobenzene

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 15h; Ambient temperature;	95%

: 5292-43-3
bromoacetic acid tert-butyl ester

: 583-69-7
2-bromobenzene-1,4-diol

: 1191430-29-1
C18H25BrO6

Conditions

Conditions	Yield
Stage #1: 2-bromobenzene-1,4-diol With caesium carbonate In acetone at 20℃; for 0.5h; Inert atmosphere; Stage #2: bromoacetic acid tert-butyl ester In acetone at 70℃; for 1h; Inert atmosphere;	94%

: 16939-57-4
(E)-1-Phenyl-1,3-butadiene

: 583-69-7
2-bromobenzene-1,4-diol

: 2-[(E)-2-phenylethenyl]coumaran-5-ol

Conditions

Conditions	Yield
With palladium diacetate; tetrabutyl-ammonium chloride; sodium carbonate In N,N-dimethyl-formamide at 100℃; for 5h; Heck reaction;	92%

: 583-69-7
2-bromobenzene-1,4-diol

: 112-89-0
1-Bromooctadecane

: 642476-84-4
1-bromo-2,5-dioctadecyloxybenzene

Conditions

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20 - 30℃; for 8h;	92%
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 2h;	90%

: 583-69-7
2-bromobenzene-1,4-diol

: 126689-00-7
2-methyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-propene

: 2-(2-methylprop-1-en-1-yl)benzene-1,4-diol

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 48h; Suzuki Coupling; Inert atmosphere;	92%

: 583-69-7
2-bromobenzene-1,4-diol

: 100-39-0
benzyl bromide

: 2237-21-0
(2-bromo-1,4-phenylene)bis(oxy)bis(methylene)dibenzene

Conditions

Conditions	Yield
With potassium carbonate In acetone Reflux;	91%
With potassium carbonate In acetone for 15h; Reflux;	89%
With potassium carbonate In acetone for 15h; Alkylation; Heating;	88%

: 111-25-1
1-bromo-hexane

: 583-69-7
2-bromobenzene-1,4-diol

: 202798-00-3
2-bromo-1,4-bis(hexyloxy)benzene

Conditions

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In N,N-dimethyl-formamide at 110℃; for 24h; Inert atmosphere;	90%
With 18-crown-6 ether; potassium carbonate In N,N-dimethyl-formamide at 110℃; for 24h; Inert atmosphere;	90%
With potassium carbonate In acetone for 72h; Reflux;	40%

: 583-69-7
2-bromobenzene-1,4-diol

: 143-15-7
1-dodecylbromide

: 171368-73-3
1-bromo-2,5-didodecyloxybenzene

Conditions

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 100℃; for 16h; Alkylation;	88%
With sodium hydroxide In N,N-dimethyl-formamide for 48h; Williamson reaction; Heating;	62%

: 110-87-2
3,4-dihydro-2H-pyran

: 583-69-7
2-bromobenzene-1,4-diol

: C16H21BrO4

Conditions

Conditions	Yield
With trifluoroacetic acid at 20℃; for 15h;	88%

: 111-83-1
1-bromo-octane

: 583-69-7
2-bromobenzene-1,4-diol

: 194204-71-2
2-bromo-1,4-bis(octyloxy)benzene

Conditions

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 22h;	87%
Stage #1: 2-bromobenzene-1,4-diol With potassium carbonate In acetonitrile at 20℃; for 1h; Stage #2: 1-bromo-octane In acetonitrile for 18h; Reflux;	77%
With potassium carbonate In butanone for 24h; Reflux; Inert atmosphere;	3.71 g

: 583-69-7
2-bromobenzene-1,4-diol

: 112-82-3
hexadecanyl bromide

: 2-bromo-1,4-bis(hexadecyloxy)benzene

Conditions

Conditions	Yield
With potassium hydroxide In ethanol Heating;	86%

: 583-69-7
2-bromobenzene-1,4-diol

: 74-88-4
methyl iodide

: 25245-34-5
1-bromo-2,5-dimethoxybenzene

Conditions

Conditions	Yield
With sodium hydride	83%

: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-phenyl trifluorovinyl ether

: 583-69-7
2-bromobenzene-1,4-diol

: 1372769-43-1
4'-(trifluorovinyloxy)biphenyl-2,5-diol

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 12h; Suzuki coupling; Inert atmosphere;	80%

: 583-69-7
2-bromobenzene-1,4-diol

: 157945-83-0
(E)-2-(3,3-dimethylbut-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: (E)-2-(3,3-dimethylbut-1-en-1-yl)benzene-1,4-diol

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 15h; Inert atmosphere;	79%

: 583-69-7
2-bromobenzene-1,4-diol

: 69739-34-0
t-butyldimethylsiyl triflate

: 78018-59-4
1,4-Bis(tert-butyldimethysiloxy)-2-bromobenzene

Conditions

Conditions	Yield
With triethylamine In chloroform	72%

: 583-69-7
2-bromobenzene-1,4-diol

: 62921-74-8
2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate

: 913544-48-6
1,4-bis((triethylene glycol monomethyl ether)oxy)-2-bromobenzene

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In butanone for 48h; Heating;	68.5%

2-Bromohydroquinone Consensus Reports

Reported in EPA TSCA Inventory.

2-Bromohydroquinone Specification

This chemical is called 2-Bromohydroquinone, and its IUPAC name is 2-bromobenzene-1,4-diol. With the molecular formula of C₆H₅BrO₂, its product categories are Anthraquinones, Hydroquinones and Quinones; Organic Building Blocks; Oxygen Compounds; Polyols. The CAS registry number of this chemical is 583-69-7. Additionally, its classification code is Reproductive Effect. It's used in chemical reagent, water, dry powder, dry sand, carbon dioxide, foam, fire extinguishing agent 1211. Moreover, it should be stored in the dry place where the temperature is low.

Other characteristics of the 2-Bromohydroquinone can be summarised as followings: (1)ACD/LogP: 2.01; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.01; (4)ACD/LogD (pH 7.4): 2; (5)ACD/BCF (pH 5.5): 19.8; (6)ACD/BCF (pH 7.4): 19.37; (7)ACD/KOC (pH 5.5): 294.97; (8)ACD/KOC (pH 7.4): 288.48; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 18.46 Å²; (13)Index of Refraction: 1.657; (14)Molar Refractivity: 37.7 cm³; (15)Molar Volume: 102.4 cm³; (16)Polarizability: 14.94×10^-24cm³; (17)Surface Tension: 62.2 dyne/cm; (18)Density: 1.844 g/cm³; (19)Flash Point: 122.1 °C; (20)Enthalpy of Vaporization: 53.77 kJ/mol; (21)Boiling Point: 278.3 °C at 760 mmHg; (22)Vapour Pressure: 0.00255 mmHg at 25°C.

Production method of this chemical: The 2-Bromohydroquinone could be obtained by the reactant of 1,4-diacetoxy-2-bromo-benzene. This reaction needs the reagent of 2.5 N aq. NaOH. The yield is 90 %. In addition, this reaction should be taken for 12 hours at ambient temperature.

The 2-Bromohydroquinone could be obtained by the reactant of 1,4-diacetoxy-2-bromo-benzene

Uses of this chemical: The 2-Bromohydroquinone could react with isopropenylbenzene, and obtain the 2-methyl-2-phenyl-2,3-dihydro-benzofuran-5-ol. This reaction needs the reagents of Na₂CO₃, Bu₄NCl, Pd(OAc)₂ and H₂SO₄. It also needs the solvents of dimethylformamide and formic acid. The yield is 62 %. In addition, this reaction should be taken for 5 hours at the temperature of 100 °C. The other condition is heating.

The 2-Bromohydroquinone could react with isopropenylbenzene, and obtain the 2-methyl-2-phenyl-2,3-dihydro-benzofuran-5-ol

When you are using this chemical, please be cautious about it as the following: This chemical is irritating to eyes, respiratory system and skin. You should wear suitable protective clothing if you use it. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1.SMILES: Brc1cc(O)ccc1O
2.InChI: InChI=1/C6H5BrO2/c7-5-3-4(8)1-2-6(5)9/h1-3,8-9H
3.InChIKey: REFDOIWRJDGBHY-UHFFFAOYAV

Product Name

BROMOHYDROQUINONE

Synthetic route

2-Bromohydroquinone Consensus Reports

2-Bromohydroquinone Specification

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