1-Bromo-2,5-dimethoxybenzene supplier

Name
1-Bromo-2,5-dimethoxybenzene
EINECS 246-756-7
CAS No. 25245-34-5
Article Data61
CAS DataBase
Density 1.412 g/cm³
Solubility Insoluble in water.
Melting Point
Formula C₈H₉BrO₂
Boiling Point 269.6 °C at 760 mmHg
Molecular Weight 217.062
Flash Point 106 °C
Transport Information
Appearance Clear colorless to yellowish liquid
Safety 37/39-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2,5-Dimethoxyphenyl bromide;2-Bromo-1,4-dimethoxybenzene;2-Bromo-4-methoxyanisole;NSC 159052;
PSA 18.46000
LogP 2.46630

Synthetic route

: 150-78-7
1,4-dimethoxybezene

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

Conditions

Conditions	Yield
With (CH3)4Br In liquid sulphur dioxide at -23℃; Rate constant;	100%
With (CH3)4Br In liquid sulphur dioxide at -23℃;	100%
With Selectfluor; sodium bromide In acetonitrile at 20℃; for 113h;	100%

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

: 74-88-4
methyl iodide

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

Conditions

Conditions	Yield
With potassium carbonate In acetone at 20℃; Inert atmosphere; Cooling with ice;	97.9%

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

: 77-78-1
dimethyl sulfate

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

Conditions

Conditions	Yield
Stage #1: 2-bromo-4-methoxyphenol With potassium carbonate In acetone at 20℃; for 0.166667h; Stage #2: dimethyl sulfate In acetone at 20℃; for 12h;	97%

: 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%

: 107099-99-0
2,5-dimethoxyphenylboronic acid

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

Conditions

Conditions	Yield
With tetrabutylammomium bromide; copper(ll) bromide In water at 100℃; Sealed tube;	78%

: potassium (2,5-dimethoxyphenyl)trifluoroborate

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

Conditions

Conditions	Yield
With tetra-N-butylammonium tribromide In tetrahydrofuran; water at 20℃; for 0.333333h; chemoselective reaction;	72%
With tetra-N-butylammonium tribromide In tetrahydrofuran; water at 20℃; for 0.333333h; chemoselective reaction;	72%

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

: 77-78-1
dimethyl sulfate

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

Conditions

Conditions	Yield
With alkali

: 150-78-7
1,4-dimethoxybezene

A: 2674-34-2
1,4-dibromo-2,5-dimethoxybenzene

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

Conditions

Conditions	Yield
With phosphorus pentabromide Erwaermen auf dem Dampfbad;
With hydrogenchloride; potassium nitrate; sodium bromide In diethyl ether; water at 25℃; for 4h; Time;

: 7789-69-7
phosphorus pentabromide

: 150-78-7
1,4-dimethoxybezene

A: 2674-34-2
1,4-dibromo-2,5-dimethoxybenzene

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

...Expand

: 150-76-5
4-methoxy-phenol

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / acetonitrile / 3 h / 0 - 20 °C 2.1: potassium carbonate / acetone / 0.17 h / 20 °C 2.2: 12 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: bromine / dichloromethane / 2 h / Cooling with ice 2: potassium carbonate / acetone / 20 °C / Inert atmosphere; Cooling with ice View Scheme

: 123-31-9
hydroquinone

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 12 h / 20 °C 2: bromine; acetic acid / 1 h / 0 - 20 °C View Scheme

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

: 286-20-4
cyclohexane-1,2-epoxide

: 500554-45-0
C14H20O3

Conditions

Conditions	Yield
Stage #1: 1-bromo-2,5-dimethoxybenzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: cyclohexane-1,2-epoxide With boron trifluoride diethyl etherate In tetrahydrofuran at -78℃;	100%

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

: 115-19-5
2-methyl-but-3-yn-2-ol

: 22944-10-1
2-methyl-4-(2,5-dimethoxyphenyl)-3-butyn-2-ol

Conditions

Conditions	Yield
With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; triethylamine In water; acetonitrile at 80℃; for 8h; Sonogashira Cross-Coupling;	99%
With piperidine; copper(l) iodide; triphenylphosphine; palladium dichloride at 80℃; for 12h; Sonogashira Cross-Coupling;	90%
With copper(l) iodide; triethylamine; triphenylphosphine; palladium diacetate at 80℃; Sonogashira coupling;	40%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 12h; Sonogashira cross-coupling;

: 1353713-99-1
2-[4,5-dihexyl(1,1'-biphenyl)-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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

: 1353714-02-9
2,5-dimethoxy-4',5'-dihexyl-1,1':2',1''-terphenyl

Conditions

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate monohydrate; palladium diacetate In water; toluene at 20 - 100℃; for 0.05h; Suzuki coupling;	99%

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

: 21433-93-2
(±)-2-methyl-but-3-yne-1,2-diol

: 4-(2,5-dimethoxyphenyl)-2-methylbut-3-yne-1,2-diol

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); N-butylamine for 21h; Sonogashira Cross-Coupling; Inert atmosphere; Heating;	99%

: 1066-35-9
dimethylmonochlorosilane

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

: 1393446-11-1
(2,5-dimethoxyphenyl)dimethylsilane

Conditions

Conditions	Yield
With iodine; magnesium In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique;	99%

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

: 98545-68-7
1-bromo-2,5-dimethoxy-4-nitrobenzene

Conditions

Conditions	Yield
With nitric acid In acetic acid at 20℃; for 0.25h;	98%
With nitric acid; acetic acid for 0.5h;	92%
With cerium(IV) ammonium nitrate supported on silica In dichloromethane for 0.25h; Ambient temperature;	87%

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

: 4555-64-0
2,2',5,5'-tetramethoxybiphenyl

Conditions

Conditions	Yield
With (i-Pent2(C6H3))2(C3H2N2))PdCl2((C5H4N)Cl); tert.-butyl lithium In toluene at 20℃; for 1h; Schlenk technique; Inert atmosphere;	98%
With bis(triphenylphosphine)nickel(II) chloride; tetraethylammonium iodide; zinc In tetrahydrofuran at 50℃; for 20h; Inert atmosphere;	70%
With iron; sodium bromide; (2,2'-bipyridine)nickel(II) dibromide In methanol; ethanol Reduction; Electrolysis;	29%
With n-butyllithium; Trimethyl borate; sodium carbonate; tetrakis(triphenylphosphine) palladium(0) 1) THF, -78 deg C -> room temperature, 4 h; room temperature, overnight, 2) THF, EtOH, H2O, toluene, reflux, 24 h; Yield given. Multistep reaction;

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

: 98-80-6
phenylboronic acid

: 54113-30-3
2,5-dimethoxy-1,1′-biphenyl

Conditions

Conditions	Yield
With potassium fluoride; 2-(diphenylphosphino)phenylferrocene; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran at 20℃; for 24h; Suzuki-Miyaura coupling;	98%
With dihydrogen dichloro-bis(di-tert-butylphosphinito-κP)palladium(2-); caesium carbonate In 1,4-dioxane at 100℃; for 20h; Suzuki-Miyaura cross-coupling reaction;	97%
With potassium carbonate In water; isopropyl alcohol at 60℃; for 4h; Catalytic behavior; Suzuki-Miyaura Coupling;	92%

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

: 675825-21-5
Lithium enolate of the acetaldehyde

: 87046-36-4
2,5-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-ol

Conditions

Conditions	Yield
With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran at -78℃; regioselective reaction;	98%
With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere;	61%

: 753-90-2
trifluoroethylamine

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

: C10H12F3NO2

Conditions

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); 5-(di(adamantan-1-yl)phosphino)-1′,3′,5′-triphenyl-1′H-1,4′-bipyrazole; potassium phenolate In 1,4-dioxane at 100℃; for 6h; Sealed tube; Inert atmosphere;	98%
With bis(η3-allyl-μ-chloropalladium(II)); 5-(di(adamantan-1-yl)phosphino)-1′,3′,5′-triphenyl-1′H-1,4′-bipyrazole; potassium phenolate In 1,4-dioxane at 100℃; for 6h; Sealed tube; Glovebox;	98%

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

: 57260-71-6
1-t-Butoxycarbonylpiperazine

: tert-butyl 4-(2,5-dimethoxyphenyl)piperazine-1-carboxylate

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 16h; Inert atmosphere;	97.01%

: 42599-16-6
(E)-1-octen-1-ylboronic acid

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

: (E)-1-(2,4-dimethoxyphenyl)octene

Conditions

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In tetrahydrofuran at 40℃; for 24h; Suzuki-Miyaura coupling;	97%

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

: 24067-17-2
4-nitrophenylboronic acid

: 112148-15-9
2,5-dimethoxy-4'-nitro-1,1'-biphenyl

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In ethanol; water; toluene at 80℃; for 8h; Suzuki Coupling; Inert atmosphere;	95.83%

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

: 1079-66-9
chloro-diphenylphosphine

: 72666-56-9
(2,5-dimethoxyphenyl)diphenylphosphine oxide

Conditions

Conditions	Yield
With sodium hydrogen sulfate; n-butyllithium; ammonium chloride; dihydrogen peroxide In tetrahydrofuran; methanol; hexane; dichloromethane	95.8%

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

: 102-56-7
2,5-dimethoxyaniline

Conditions

Conditions	Yield
With bis(tri-ortho-tolylphosphine)palladium(0); (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 100℃; for 12h; Inert atmosphere;	95%
With copper(I) oxide; sodium azide; L-proline In dimethyl sulfoxide at 100℃; for 6h; Inert atmosphere;	71%
With potassium amide In ammonia	62%
Stage #1: 1-bromo-2,5-dimethoxybenzene With magnesium In tetrahydrofuran Inert atmosphere; Stage #2: With C10H17NO In tetrahydrofuran; toluene at -45℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water; toluene Inert atmosphere;	58%

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

: 93605-93-7, 93605-94-8, 107136-09-4, 107136-10-7, 107136-11-8, 107136-12-9, 108586-11-4
1β,2α-dimethyl-5α-(t-butyldimethylsilyloxy)-1,2,4aβ,5,6,7,8,8aα-octahydronaphthalene-1α-carboxaldehyde

: trans-5α-(tert-butyldimethylsilyloxy)-1α-[(2,5-dimethoxyphenyl)-hydroxymethyl]-1,2,4a,5,6,7,8,8a-octahydro-1β,2α-dimethylnaphthalene

Conditions

Conditions	Yield
Stage #1: 1-bromo-2,5-dimethoxybenzene With magnesium; ethylene dibromide In tetrahydrofuran; diethyl ether for 2.5h; Metallation; Heating; Stage #2: 1β,2α-dimethyl-5α-(t-butyldimethylsilyloxy)-1,2,4aβ,5,6,7,8,8aα-octahydronaphthalene-1α-carboxaldehyde In tetrahydrofuran; diethyl ether at 0℃; for 0.5h; Grignard reaction;	95%

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

: 1066-54-2
trimethylsilylacetylene

: 531504-78-6
((2,5-dimethoxyphenyl)ethynyl)trimethylsilane

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine; triphenylphosphine In N,N-dimethyl-formamide at 120℃; for 0.5h; Sonogashira Cross-Coupling; Microwave irradiation; Inert atmosphere;	95%
With piperidine; copper(l) iodide; triphenylphosphine; palladium dichloride for 24h; Sonogashira coupling; Heating;	89%

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

: 107-19-7
propargyl alcohol

: 3-(2,5-dimethoxyphenyl)-prop-2-yn-1-ol

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); N-butylamine for 21h; Sonogashira Cross-Coupling; Inert atmosphere; Heating;	95%
With copper(l) iodide; diisopropylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 80℃; for 18h;	29%

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

: 78-80-8
2-methyl-1-buten-3-yne

: 22944-05-4
1,4-dimethoxy-2-(3-methylbut-3-en-1-yn-1-yl)benzene

Conditions

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-butylamine at 0 - 100℃; for 21h; Catalytic behavior; Temperature; Sonogashira Cross-Coupling; Inert atmosphere;	94%

: 1066-35-9
dimethylmonochlorosilane

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

: 2-bromo-1,4-dimethoxy-3-(dimethylsilyl)benzene

Conditions

Conditions	Yield
With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; diethyl ether at -110 - -80℃; for 1h; Solvent; Temperature; Glovebox; Inert atmosphere;	94%
With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; diethyl ether at -110 - -80℃; Inert atmosphere;	94%

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

: 106-95-6
allyl bromide

: 19754-22-4
2-allyl-1,4-dimethoxybenzene

Conditions

Conditions	Yield
With magnesium In diethyl ether at 0 - 20℃; for 2h; Grignard Reaction; Inert atmosphere;	93%
With n-butyllithium; copper (I) iodide Yield given. Multistep reaction;
Stage #1: 1-bromo-2,5-dimethoxybenzene With iodine; magnesium In tetrahydrofuran for 4h; Reflux; Inert atmosphere; Stage #2: allyl bromide With copper(I) bromide; lithium bromide In tetrahydrofuran at 20℃; Inert atmosphere;

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

: 24342-03-8
isobutyl vinylacetate

: (E)-isobutyl 4-(2,5-dimethoxyphenyl)but-3-enoate

Conditions

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); N-Methyldicyclohexylamine In toluene at 110℃; for 12h; Heck Reaction; Inert atmosphere;	93%

: 611-20-1
salicylonitrile

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

: 3-(2,5-dimethoxyphenyl)benzo[d]isoxazole

Conditions

Conditions	Yield
With magnesium; triphenylphosphine In tetrahydrofuran; toluene at 90℃; for 4h; Reagent/catalyst;	93%

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

: 75-36-5
acetyl chloride

: 90841-64-8
1-(4-bromo-2,5-dimethoxyphenyl)ethanone

Conditions

Conditions	Yield
With aluminium trichloride In nitrobenzene for 2h; Ambient temperature;	92%

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

: 252651-57-3
(R)-2-methyl-2-[2'-(phenylmethoxy)ethyl]oxirane

: 300661-18-1
(S)-4-benzyloxy-1-(2',5'-dimethoxyphenyl)-2-methylbutan-2-ol

Conditions

Conditions	Yield
Stage #1: 1-bromo-2,5-dimethoxybenzene With iodine; magnesium In tetrahydrofuran for 4h; Metallation; Heating; Stage #2: (R)-2-methyl-2-[2'-(phenylmethoxy)ethyl]oxirane With dilithium tetrachlorocuprate In tetrahydrofuran at -78 - -20℃; Ring cleavage; Grignard reaction;	92%

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

: 200943-34-6
4-bromo-1-(4-bromo-2,5-dimethoxyphenyl)-2,5-dimethoxybenzene

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at -40℃; for 1.5h;	91%
With iron(III) chloride In dichloromethane	70%
With iron(III) chloride In dichloromethane	68%
With aluminium trichloride; iron(III) chloride 1.) nitromethane, 30 min, RT 2.) nitromethane, RT, 5 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: bis(triphenylphosphine)nickel(II) chloride; tetraethylammonium iodide; zinc / tetrahydrofuran / 20 h / 50 °C / Inert atmosphere 2: N-Bromosuccinimide / dichloromethane / 10 h / Reflux View Scheme

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

: 205934-63-0
(2R,4R,5R,6R)-4-acetyl-5-benzyloxy-2-phenyl-6-vinyl-[1,3]dioxane

A: (2R,4R,5R,6R)-5-benzyloxy-4-[(1R)-1-hydroxy-1-(2,5-dimethoxyphenyl)-ethyl]-2-phenyl-6-vinyl-[1,3]dioxane

B: (2R,4R,5R,6R)-5-benzyloxy-4-[(1S)-1-hydroxy-1-(2,5-dimethoxyphenyl)-ethyl]-2-phenyl-6-vinyl-[1,3]dioxane

Conditions

Conditions	Yield
With n-butyllithium; cerium(III) chloride In tetrahydrofuran at -78℃; for 2h;	A 2% B 91%
With n-butyllithium In tetrahydrofuran at 0℃;	A 58% B 32%

...Expand

1-Bromo-2,5-dimethoxybenzene Specification

The Benzene,2-bromo-1,4-dimethoxy-, with the CAS registry number 25245-34-5, is also known as 2,5-Dimethoxybromobenzene. It belongs to the product categories of Aromatic Hydrocarbons (substituted) & Derivatives; Benzene derivates; API intermediates; Ethers; Organic Building Blocks; Oxygen Compounds. Its EINECS number is 246-756-7. This chemical's molecular formula is C₈H₉BrO₂ and formula weight is 217.06. What's more, its IUPAC name is 2-bromo-1,4-dimethoxybenzene. Its classification codes are: (1)TSCA Flag P; (2)TSCA Flag S.

Physical properties of Benzene,2-bromo-1,4-dimethoxy- are: (1)ACD/LogP: 2.79; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.79; (4)ACD/BCF (pH 5.5): 77.8; (5)ACD/KOC (pH 5.5): 785.53; (6)#H bond acceptors: 2; (7)#H bond donors: 0; (8)#Freely Rotating Bonds: 2; (9)Polar Surface Area: 18.46 Å²; (10)Index of Refraction: 1.527; (11)Molar Refractivity: 47.3 cm³; (12)Molar Volume: 153.6 cm³; (13)Surface Tension: 34 dyne/cm; (14)Density: 1.412 g/cm³; (15)Flash Point: 106 °C; (16)Enthalpy of Vaporization: 48.73 kJ/mol; (17)Boiling Point: 269.6 °C at 760 mmHg; (18)Vapour Pressure: 0.0119 mmHg at 25°C.

Preparation: this chemical can be prepared by 1,4-dimethoxy-benzene by heating. This reaction will need reagent Br₂ and solvent acetic acid with the reaction time of 1 hour. It is a reaction of bromination. The yield is about 90%.

Uses of Benzene,2-bromo-1,4-dimethoxy-: it can be used to produce 1-bromo-2,5-dimethoxy-4-nitro-benzene at the ambient temperature. It will need reagent cerium ammonium nitrate coated on silica and solvent CH₂Cl₂ with the reaction time of 15 min. The yield is about 87%.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you should wear suitable gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: COC1=CC(=C(C=C1)OC)Br
(2)InChI: InChI=1S/C8H9BrO2/c1-10-6-3-4-8(11-2)7(9)5-6/h3-5H,1-2H3
(3)InChIKey: DWCGNRKFLRLWCJ-UHFFFAOYSA-N

Product Name

1-Bromo-2,5-dimethoxybenzene

Synthetic route

1-Bromo-2,5-dimethoxybenzene Specification

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