5000-65-7

Basic information

• Product Name: 3'-METHOXYPHENACYL BROMIDE
• Synonyms: 3'-Methoxyphenacyl Bromide [for HPLC Labeling];1-(Bromoacetyl)-3-methoxybenzene;α-Bromo-3'-methoxyacetophenone;α-Bromo-m-methoxyacetophenone;2-Bromo-3'-methoxyacetophenone,97%;m-Mehtoxyphenacyl Bromide;2-bromo-3-methyoxyacetophenone;NSC 405833
• CAS NO: 5000-65-7
• Molecular Formula: C₉H₉BrO₂
• Molecular Weight: 229.07
• EINECS: 225-666-1
• Product Categories: Analytical Chemistry;Carboxyl Group Labeling Reagents for HPLC;HPLC Labeling Reagents;UV Detection (HPLC Labeling Reagents);Aromatics;Intermediates;Aromatic Halides (substituted)
• Mol File: 5000-65-7.mol
• Article Data: 85

Chemical Properties

• Melting Point: 60-62 °C(lit.)
• Boiling Point: 215.8°C (rough estimate)
• Flash Point: 122 °C
• Appearance: White to slightly yellow-green/Crystalline Powder
• Density: 1.4921 (rough estimate)
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: 0-6°C
• Solubility: soluble in Methanol
• BRN: 510128
• CAS DataBase Reference: 3'-METHOXYPHENACYL BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-METHOXYPHENACYL BROMIDE(5000-65-7)
• EPA Substance Registry System: 3'-METHOXYPHENACYL BROMIDE(5000-65-7)

Safety Data

• Hazard Codes: C
• Statements: 34-36/37-22
• Safety Statements: 26-27-28-36/37/39-45-34
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 5000-65-7(Hazardous Substances Data)

Usage

Chemical Properties

WHITE TO SLIGHTLY YELLOW-GREEN CRYST. POWDER

Uses

Different sources of media describe the Uses of 5000-65-7 differently. You can refer to the following data:
1. Derivatizing reagent.
2. 2-bromo-3′-methoxyacetophenone, an alkylating agent, has been used to stabilize clopidogrel active metabolite (AM) in human plasma. It has also been used in the derivatisation of active metabolites in blood to ensure its stability during sample processing and storage.

Preparation

Obtained by reaction of bromine with 3-methoxyacetophenone in chloroform at 0° for 3 h (88%).

Synthetic route

1-(3-Methoxyphenyl)ethanone (586-37-8) → 2-bromo-3'-methoxyacetophenone (5000-65-7)

Conditions	Yield
With phenyltrimethylammonium tribromide In tetrahydrofuran at 20℃; for 1h;	100%
With bromine In chloroform at 20℃; for 24h;	100%
With bromine In chloroform at 20℃; for 4h;	97%

acetophenone (98-86-2) → 2-bromo-3'-methoxyacetophenone (5000-65-7)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sulfuric acid; nitric acid / 0.33 h / -10 - -5 °C 2.1: hydrogenchloride; iron / water / Reflux 3.1: sulfuric acid / water / 0.5 h / 45 - 50 °C 3.2: 0.5 h / 0 - 5 °C 3.3: 2 h / 90 °C 4.1: 50 - 60 °C 5.1: N-Bromosuccinimide / ethyl acetate / 3 h / 20 °C View Scheme

3-Nitroacetophenone (121-89-1) → 2-bromo-3'-methoxyacetophenone (5000-65-7)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogenchloride; iron / water / Reflux 2.1: sulfuric acid / water / 0.5 h / 45 - 50 °C 2.2: 0.5 h / 0 - 5 °C 2.3: 2 h / 90 °C 3.1: 50 - 60 °C 4.1: N-Bromosuccinimide / ethyl acetate / 3 h / 20 °C View Scheme

1-(3-aminophenyl)ethanone (99-03-6) → 2-bromo-3'-methoxyacetophenone (5000-65-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sulfuric acid / water / 0.5 h / 45 - 50 °C 1.2: 0.5 h / 0 - 5 °C 1.3: 2 h / 90 °C 2.1: 50 - 60 °C 3.1: N-Bromosuccinimide / ethyl acetate / 3 h / 20 °C View Scheme

2-bromo-3'-methoxyacetophenone (5000-65-7) + benzenecarbothioamide (2227-79-4) → C16H13NOS (1013593-35-5)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 8h; Reflux;	100%

1-[3-(2-pyridyl)-2-pyridyl]piperazine (1414942-27-0) + 2-bromo-3'-methoxyacetophenone (5000-65-7) → 1-(3-methoxyphenyl)-2-[4-[3-(2-pyridyl)-2-pyridyl]piperazin-1-yl]ethanone (1414942-20-3)

Conditions	Yield
With potassium carbonate In acetonitrile Reflux;	100%
With potassium carbonate In acetonitrile Reflux;	100%

2-bromo-3'-methoxyacetophenone (5000-65-7) + potassium thioacetate (10387-40-3) → 2-(acetylsulfanyl)-1-(3-methoxyphenyl)ethan-1-one (175657-38-2)

Conditions	Yield
In ethanol; acetone at 20℃; for 2h;	100%

phenylglyoxylic acid potassium salt (63468-90-6) + 2-bromo-3'-methoxyacetophenone (5000-65-7) → 2-(3-methoxyphenyl)-2-oxoethyl 2-oxo-2-phenylacetate

Conditions	Yield
In dimethyl sulfoxide at 20℃; for 0.5h; Inert atmosphere; Schlenk technique;	100%

4-methoxypyridine (620-08-6) + 2-bromo-3'-methoxyacetophenone (5000-65-7) → 4-methoxy-1-(2-(3-methoxyphenyl)-2-oxoethyl)pyridin-1-ium bromide

Conditions	Yield
In tetrahydrofuran for 0.5h; Reflux;	99%
In acetonitrile at 45℃; Kinetics; pyridinolysis;
In acetone at 20℃; for 5h; Inert atmosphere;

[(2,2'-bipyridine)Cu(SeCF3)]2 (1447204-38-7) + 2-bromo-3'-methoxyacetophenone (5000-65-7) → C10H9F3O2Se

Conditions	Yield
With potassium phosphate In dichloromethane at 45℃; for 16h; Inert atmosphere;	98%

2-bromo-3'-methoxyacetophenone (5000-65-7) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → (3-methoxybenzoylmethyldiphenyl-2-diphenylphosphinoethylphosphonium)-bromide

Conditions	Yield
In chloroform	98%
In chloroform at 20℃; for 15h; Inert atmosphere; Schlenk technique;	98%

p-toluidine (106-49-0) + 2-bromo-3'-methoxyacetophenone (5000-65-7) → 1-(3-methoxyphenyl)-2-(4-methylphenylamino)ethanone

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 20℃; for 24h;	98%

2-bromo-3'-methoxyacetophenone (5000-65-7) → 2-bromo-1-(3-methoxyphenyl)ethan-1-one oxime

Conditions	Yield
With hydroxylamine hydrochloride In methanol; water at 0 - 20℃;	98%

2-Amino-4-methylpyridine (695-34-1) + 2-bromo-3'-methoxyacetophenone (5000-65-7) → 2-(3-Methoxy-phenyl)-7-methyl-imidazo[1,2-a]pyridine

Conditions	Yield
In neat (no solvent) at 25 - 30℃; Milling; Green chemistry;	98%

2-bromo-3'-methoxyacetophenone (5000-65-7) + hex-1-yne (693-02-7) → 2-(4-butyl-1H-1,2,3-triazol-1-yl)-1-(3-methoxyphenyl)ethanone (1536405-99-8)

Conditions	Yield
With sodium azide; sodium ascorbate In ethanol; water at 20℃; for 0.333333h; regioselective reaction;	97%
With sodium azide; sodium L-ascorbate In ethanol; water at 85℃; for 0.416667h;	96%

2-bromo-3'-methoxyacetophenone (5000-65-7) + 7-hydroxy-4-(4-methoxyphenyl)-8-methyl-2H-2-chromenone (370583-62-3) → 4-(4-methoxyphenyl)-7-[2-(3-methoxyphenyl)-2-oxoethoxy]-8-methyl-2-chromenone (500203-99-6)

Conditions	Yield
With potassium carbonate In acetone at 50 - 56℃; Williamson reaction;	96%

N-Cbz-L-Phe (1161-13-3) + 2-bromo-3'-methoxyacetophenone (5000-65-7) → 2-(1-(S)-((Phenylmethoxy)carbonyl)-amino-2-phenylethyl)-4-(4-methoxyphenyl)-imidazole

Conditions	Yield
With ammonium acetate; caesium carbonate In water; N,N-dimethyl-formamide	96%

4-methoxy-benzaldehyde (123-11-5) + thiosemicarbazide (79-19-6) + 2-bromo-3'-methoxyacetophenone (5000-65-7) → (E)-2-(2-(4-methoxybenzylidene)hydrazinyl)-4-(3-methoxyphenyl)thiazole

Conditions	Yield
In water at 25 - 30℃;	96%

3-Hydroxy-4-methyl-7,8,9,10-tetrahydro-6H-dibenzopyran-6-one (55047-37-5) + 2-bromo-3'-methoxyacetophenone (5000-65-7) → 3-[2-(3-methoxyphenyl)-2-oxoethoxy]-4-methyl-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one

Conditions	Yield
Stage #1: 3-Hydroxy-4-methyl-7,8,9,10-tetrahydro-6H-dibenzopyran-6-one With potassium carbonate In acetone at 50 - 56℃; Williamson reaction; Stage #2: 2-bromo-3'-methoxyacetophenone In acetone for 1h; Williamson reaction; Heating;	95%

2-bromo-3'-methoxyacetophenone (5000-65-7) + diethyl 1H-pyrazole-3,5-dicarboxylate (37687-24-4) → C18H20N2O6 (1316761-36-0)

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 12h;	95%

benzophenone hydrazone (5350-57-2) + 2-bromo-3'-methoxyacetophenone (5000-65-7) + p-nitrophenyl isothiocyanate (2131-61-5) → N-(diphenylmethylene)-4-(3-methoxyphenyl)-2-(4-nitrophenylimino)thiazol-3(2H)-amine

Conditions	Yield
With triethylamine In ethanol for 3h; Reflux;	95%

thiosemicarbazide (79-19-6) + 2-bromo-3'-methoxyacetophenone (5000-65-7) + 2,4-Dimethoxybenzaldehyde (613-45-6) → (E)-2-(2-(2,4-dimethoxybenzylidene)hydrazinyl)-4-(3-methoxyphenyl)thiazole

Conditions	Yield
In water at 25 - 30℃;	95%

isonicotinic acid ethylester (1570-45-2) + 2-bromo-3'-methoxyacetophenone (5000-65-7) → 4-(ethoxycarbonyl)-1-[2-(3-methoxyphenyl)-2-oxoethyl]pyridinium bromide

Conditions	Yield
In acetone at 20℃; for 24h;	95%

5-hydroxy-2,2-dimethyl-2H-chromene-6-carbaldehyde (54287-99-9) + 2-bromo-3'-methoxyacetophenone (5000-65-7) → (7,7-dimethyl-7H-furo[2,3-f]chromen-2-yl)(3-methoxyphenyl)methanone

Conditions	Yield
With potassium carbonate In acetonitrile at 20 - 120℃; for 4h;	95%

Upstream product

• 586-37-8 1-(3-Methoxyphenyl)ethanone 
• 98-86-2 acetophenone 
• 121-89-1 3-Nitroacetophenone 
• 99-03-6 1-(3-aminophenyl)ethanone 

Downstream Products

• 99985-55-4 2-(dimethylamino)-1-(3-methoxyphenyl)ethan-1-one 
• 857724-35-7 2-isopropylamino-1-(3-methoxy-phenyl)-ethanone 
• 168154-47-0 acetylamino-(3-methoxy-phenacyl)-malonic acid diethyl ester 
• 32017-77-9 2-(m-methoxyphenyl)oxirane 
• 94195-90-1 (+/-)-ethyl 2-acetyl-4-(3-methoxyphenyl)-4-oxobutanoate 
• 65083-12-7 17aβ-(t-Butoxy)-3-methoxy-D-homo-9,10-secooestra-1,3,5(10),8(14)-tetraen-6,9-dion 
• 54669-78-2 2-[2-(3-methoxyphenyl)-2-oxoethyl]-cyclohexanone 
• 188119-49-5 3-methoxyphenacyl diethyl phosphate 
• 310902-10-4 2-[2-(3-methoxyphenyl)-2-oxoethyl]-cyclopentanone 
• 237384-18-8 methyl 4-[4-(3-methoxyphenyl)(1,3-thiazol-2-yl)]-5-methylthiothiophene-2-carboxylate 
• 384364-50-5 4-(4-methoxyphenyl)-7-[2-(3-methoxyphenyl)-2-oxoethoxy]-2H-2-chromenone 

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