116091-63-5

Basic information

• Product Name: 5-Acetonyl-2-methoxybenzene sulfonamide
• Synonyms: 5-ACETONYL-2-METHOXYBENZENE SULFONAMIDE;5-ACETONYL-2-METHOXYBENZENE SULPHONAMIDE;5-(2-OXOPROPYL)-2-METHOXY BENZENE SULPHONAMIDE;2-METHOXY-5-(2-OXO-PROPYL)BENZENESULFONAMIDE;2-METHOXY-5-(2-OXOPROPYL)BENZENE SULPHONAMIDE;5-(2-Oxypropyl)-2-methoxybenzenesulfonamide;5-(2-OXYPROPYL)-2-METHOXYBENZENE SULPHONAMIDE 98+%;5-(2-Oxypropyl)-2-methoxybenze
• CAS NO: 116091-63-5
• Molecular Formula: C₁₀H₁₃NO₄S
• Molecular Weight: 243.28
• EINECS: 1806241-263-5
• Product Categories: API intermediates;(intermediate of tamsulosin);Tamsulosin;Valsartan
• Mol File: 116091-63-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 194-197°C
• Boiling Point: 444.618 °C at 760 mmHg
• Flash Point: 222.697 °C
• Appearance: Yellow crystalline powder
• Density: 1.288 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 9.91±0.60(Predicted)
• CAS DataBase Reference: 5-Acetonyl-2-methoxybenzene sulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Acetonyl-2-methoxybenzene sulfonamide(116091-63-5)
• EPA Substance Registry System: 5-Acetonyl-2-methoxybenzene sulfonamide(116091-63-5)

Safety Data

• Hazardous Substances Data: 116091-63-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 116091-63-5 differently. You can refer to the following data:
1. 5-Acetonyl-2-methoxybenzene is used in the synthesis of tamsulosin, a drug used in benign prostatic hyperplasia therapy.
2. 5-Acetonyl-2-methoxybenzene sulfonamide can be used as Tamsulosine intermediate.

InChI:InChI=1/C10H12O2.H3NO2S/c1-8(11)7-9-3-5-10(12-2)6-4-9;1-4(2)3/h3-6H,7H2,1-2H3;4H,(H2,1,2,3)

Synthetic route

2-methoxy-5-(2-oxopropyl)benzenesulfonyl chloride (80223-79-6) → 2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5)

Conditions	Yield
With ammonia In tetrahydrofuran; water	74%
With ammonium hydroxide In tetrahydrofuran for 2h; Ambient temperature; Yield given;
With ammonia In tetrahydrofuran; water at 20℃;
With ammonia; triethylamine In dichloromethane at 0 - 20℃; for 5h;
With ammonium hydroxide In ethyl acetate at -5 - 20℃; for 2h;	63 g

4-methoxybenzyl methyl ketone (122-84-9) → 2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 11.4 g / ClSO3H / 2 h / Ambient temperature 2: conc. aq. NH4OH / tetrahydrofuran / 2 h / Ambient temperature View Scheme
Stage #1: 4-methoxybenzyl methyl ketone With chlorosulfonic acid at -5 - 15℃; for 4h; Stage #2: With ammonia In tetrahydrofuran at 8 - 25℃; for 15h; pH=8.8 - 9.8;
With chlorosulfonic acid; ammonium hydroxide In water; ethyl acetate
Multi-step reaction with 2 steps 1: chlorosulfonic acid / 2 h / 0 - 20 °C 2: ammonia; triethylamine / dichloromethane / 5 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: chlorosulfonic acid / 2 h / -15 - 20 °C 2: ammonium hydroxide / ethyl acetate / 2 h / -5 - 20 °C View Scheme

C10H12O5S → 2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5)

Conditions	Yield
With ammonia In tetrahydrofuran at 8 - 40℃; for 15h; pH=~ 8.8 - 9.8;

2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) + Benzhydrylamine (91-00-9) → 5-(2-(benzhydrylamino)propyl)-2-ethylbenzenesulfonamide

Conditions	Yield
With titanium(IV) isopropylate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; C27H34NO2P; hydrogen; trifluoroacetic acid In dichloromethane at 20℃; under 45603.1 Torr; Autoclave; Molecular sieve; enantioselective reaction;	91%

(R)-1-phenyl-ethyl-amine (3886-69-9) + 2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → 5-[[(2R)-2-[(1R)-N-(1-methylbenzyl)]amino]propyl]-2-methoxybenzenesulfonamide hydrochloride (116091-64-6)

Conditions	Yield
Stage #1: (R)-1-phenyl-ethyl-amine; 2-methoxy-5-(2-oxopropyl)benzenesulfonamide With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 30 - 35℃; for 16h; Stage #2: With hydrogenchloride In water for 0.5h;	71.7%
Stage #1: (R)-1-phenyl-ethyl-amine; 2-methoxy-5-(2-oxopropyl)benzenesulfonamide With hydrogen; platinum(IV) oxide In methanol under 760.051 Torr; for 20h; Stage #2: With hydrogenchloride In ethanol	53%
With hydrogen; nickel In methanol at 50℃; under 2625.26 - 4125.41 Torr;
With hydrogen; nickel In methanol at 50℃; under 2625.26 - 4125.41 Torr;

2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) + benzylamine (100-46-9) → 5-[2-(N-benzyl-amino)-propyl]-2-methoxy-benzenesulphonamide hydrochloride (671817-79-1)

Conditions	Yield
Stage #1: 2-methoxy-5-(2-oxopropyl)benzenesulfonamide; benzylamine In methanol for 2h; Heating / reflux; Stage #2: With sodium hydroxide; sodium tetrahydroborate In methanol at 35 - 40℃; for 2h; Stage #3: With hydrogenchloride In ethanol pH=1;	55.2%

2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → (+/-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide (112244-38-9)

Conditions	Yield
With ammonium acetate; sodium cyanoborohydride In methanol at 20℃; for 15h;	35%

2-(2-methoxy-phenoxy)-ethylamine (1836-62-0) + 2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → 2-Methoxy-5-{2-[(E)-2-(2-methoxy-phenoxy)-ethylimino]-propyl}-benzenesulfonamide

Conditions	Yield
In methanol for 1h; Heating;

2-(5-fluoro-2-methoxy-phenoxy)ethylamine (120352-00-3) + 2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → 5-{2-[(E)-2-(5-Fluoro-2-methoxy-phenoxy)-ethylimino]-propyl}-2-methoxy-benzenesulfonamide

Conditions	Yield
In methanol for 1h; Heating;

2-(5-Chloro-2-methoxy-phenoxy)-ethylamine + 2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → 5-{2-[(E)-2-(5-Chloro-2-methoxy-phenoxy)-ethylimino]-propyl}-2-methoxy-benzenesulfonamide

Conditions	Yield
In methanol for 1h; Heating;

2-(3-Fluoro-2-methoxy-phenoxy)-ethylamine (125960-72-7) + 2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → 5-{2-[(E)-2-(3-Fluoro-2-methoxy-phenoxy)-ethylimino]-propyl}-2-methoxy-benzenesulfonamide

Conditions	Yield
In methanol for 1h; Heating;

2-(4-fluoro-2-methoxyphenoxy)ethan-1-amine (125960-68-1) + 2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → 5-{2-[(E)-2-(4-Fluoro-2-methoxy-phenoxy)-ethylimino]-propyl}-2-methoxy-benzenesulfonamide

Conditions	Yield
In methanol for 1h; Heating;

3-(5-Fluoro-2-methoxy-phenoxy)-propylamine (147291-85-8) + 2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → 5-{2-[(E)-3-(5-Fluoro-2-methoxy-phenoxy)-propylimino]-propyl}-2-methoxy-benzenesulfonamide

Conditions	Yield
In methanol for 1h; Heating;

2-(2-Ethoxy-5-fluoro-phenoxy)-ethylamine (125960-76-1) + 2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → 5-{2-[(E)-2-(2-Ethoxy-5-fluoro-phenoxy)-ethylimino]-propyl}-2-methoxy-benzenesulfonamide

Conditions	Yield
In methanol for 1h; Heating;

2-(5-Fluoro-2-propoxy-phenoxy)-ethylamine (125960-84-1) + 2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → 5-{2-[(E)-2-(5-Fluoro-2-propoxy-phenoxy)-ethylimino]-propyl}-2-methoxy-benzenesulfonamide

Conditions	Yield
In methanol for 1h; Heating;

4-(5-Fluoro-2-methoxy-phenoxy)-butylamine + 2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → 5-{2-[(E)-4-(5-Fluoro-2-methoxy-phenoxy)-butylimino]-propyl}-2-methoxy-benzenesulfonamide

Conditions	Yield
In methanol for 1h; Heating;

2-(2-Butoxy-5-fluoro-phenoxy)-ethylamine (125960-80-7) + 2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → 5-{2-[(E)-2-(2-Butoxy-5-fluoro-phenoxy)-ethylimino]-propyl}-2-methoxy-benzenesulfonamide

Conditions	Yield
In methanol for 1h; Heating;

2-(5-Fluoro-2-hexyloxy-phenoxy)-ethylamine + 2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → 5-{2-[(E)-2-(5-Fluoro-2-hexyloxy-phenoxy)-ethylimino]-propyl}-2-methoxy-benzenesulfonamide

Conditions	Yield
In methanol for 1h; Heating;

2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) + 2-(5-Fluoro-2-octyloxy-phenoxy)-ethylamine → 5-{2-[(E)-2-(5-Fluoro-2-octyloxy-phenoxy)-ethylimino]-propyl}-2-methoxy-benzenesulfonamide

Conditions	Yield
In methanol for 1h; Heating;

2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) + 2-(2-Decyloxy-5-fluoro-phenoxy)-ethylamine → 5-{2-[(E)-2-(2-Decyloxy-5-fluoro-phenoxy)-ethylimino]-propyl}-2-methoxy-benzenesulfonamide

Conditions	Yield
In methanol for 1h; Heating;

2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → (+/-)-5-<2--N-methylamino>propyl>-2-methoxybenzenesulfonamide (144818-58-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: methanol / 1 h / Heating 2: NaBH4 / methanol / 3 h / Ambient temperature 3: methanol; H2O / 1 h / Heating 4: NaBH4 / methanol; H2O / 1 h / Ambient temperature View Scheme

2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → 5-(2-{[2-(5-Fluoro-2-methoxy-phenoxy)-ethyl]-formyl-amino}-propyl)-2-methoxy-benzenesulfonamide

Conditions	Yield
Multi-step reaction with 3 steps 1: methanol / 1 h / Heating 2: NaBH4 / methanol / 3 h / Ambient temperature 3: methanol; H2O / 1 h / Heating View Scheme

2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → 2-methoxy-5-[2-[2-(2-methoxyphenoxy)ethylamino]-2-methylethyl]-benzensulfonamide (94666-11-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 1 h / Heating 2: NaBH4 / methanol / 3 h / Ambient temperature View Scheme

2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → 5-[2-[2-(3-Fluoro-2-methoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide (144818-65-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 1 h / Heating 2: NaBH4 / methanol / 3 h / Ambient temperature View Scheme

2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → (+/-)-5-<2-<<2-(5-fluoro-2-methoxyphenoxy)ethyl>amino>propyl>-2-methoxybenzenesulfonamide (144818-22-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 1 h / Heating 2: NaBH4 / methanol / 3 h / Ambient temperature View Scheme

2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → 5-{2-[2-(5-Chloro-2-methoxy-phenoxy)-ethylamino]-propyl}-2-methoxy-benzenesulfonamide (144818-67-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 1 h / Heating 2: NaBH4 / methanol / 3 h / Ambient temperature View Scheme

2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → 5-[2-[2-(4-Fluoro-2-methoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide (144818-66-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 1 h / Heating 2: NaBH4 / methanol / 3 h / Ambient temperature View Scheme

2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → 5-[2-[2-(2-Ethoxy-5-fluorophenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide (144818-59-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 1 h / Heating 2: NaBH4 / methanol / 3 h / Ambient temperature View Scheme

2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → 5-{2-[3-(5-Fluoro-2-methoxy-phenoxy)-propylamino]-propyl}-2-methoxy-benzenesulfonamide (144818-56-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 1 h / Heating 2: NaBH4 / methanol / 3 h / Ambient temperature View Scheme

2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → 5-[2-[2-(5-Fluoro-2-n-propoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide (144818-60-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 1 h / Heating 2: NaBH4 / methanol / 3 h / Ambient temperature View Scheme

2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → 5-{2-[4-(5-Fluoro-2-methoxy-phenoxy)-butylamino]-propyl}-2-methoxy-benzenesulfonamide (144818-57-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 1 h / Heating 2: NaBH4 / methanol / 3 h / Ambient temperature View Scheme

Upstream product

• 122-84-9 4-methoxybenzyl methyl ketone 
• 80223-79-6 2-methoxy-5-(2-oxopropyl)benzenesulfonyl chloride 

Downstream Products

• 671817-79-1 5-[2-(N-benzyl-amino)-propyl]-2-methoxy-benzenesulphonamide hydrochloride 
• 116091-64-6 5-[[(2R)-2-[(1R)-N-(1-methylbenzyl)]amino]propyl]-2-methoxybenzenesulfonamide hydrochloride 
• 133868-59-4 (+/-)-5-<2-<<2-(5-fluoro-2-methoxyphenoxy)ethyl>amino>propyl>-2-methoxybenzenesulfonamide hydrochloride 
• 882494-06-6 oxalate salt of tamsulosin 
• 119714-13-5 (S)-(+)-5-(2-aminopropyl)-2-methoxybenzene sulfonamide 
• 112101-81-2 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide 
• 1391850-36-4 2-methoxy-5-[(2R)-2-(piperazin-1-yl)propyl]benzenesulfonamide 
• 1391850-34-2 2-methoxy-5-[(2R)-2-(4-methylpiperazin-1-yl)propyl]benzenesulfonamide 
• 1391850-38-6 2-methoxy-5-[(2R)-2-(4-ethylpiperazin-1-yl)propyl]benzenesulfonamide 
• 521300-99-2 (R)-tamsarocin (-)-camphor-10-sulfonate 
• 521301-00-8 (S)-tamsarocin (+)-camphor-10-sulfonate 
• 106133-20-4 tamsulosin hydrochloride 
• 94666-07-6 5-[2-[2-(2-ethoxyphenoxy)-ethylamino]-2-methylethyl]-2-methoxybenzenesulfonamide 
• 112244-38-9 (+/-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide 

Relevant articles and documents

Method of resolving tamsulosin enantiomer

The invention relates to a method of resolving tamsulosin enantiomer, and in particular, relates to a method of resolving tamsulosin, represented as the formula (I), into an R-enantiomer and an S-enantiomer. The method includes the steps of: (a) dissolving a solid mixture of (R)-tamsulosin free alkali and (S)-tamsulosin free alkali in a solvent and performing a reaction to the free alkalis with camphor-10-sulfonic acid to form a solution containing a pair of diastereomeric camphor-10-sulfonates of tamsulosin, and then preferentially precipitating one diastereomeric camphor-10-sulfonate of the tamsulosin from the solution containing a pair of the diastereomeric camphor-10-sulfonates of tamsulosin, thereby forming a precipitate, in which one diastereomer is enriched, and a solute, in which the other one diastereomer is enriched; and (b) from one of the precipitate and the solute, releasing tamsulosin free alkali to obtain optical-rotation-enriched tamsulosin free alkali. The method has excellent technical performance.

Tamsulosin derivative

The optically active compound, R(?)-5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-hydroxybenzenesulfonamide in good optical purity, a metabolite of the α1-adrenergic blocking agent tamsulosin, and methods for the preparation thereof. Pharmaceutical compositions including the optically active compound and methods of treatment comprising administration of an effective α-adrenergic antagonistic amount of such compositions to mammals.

TAMSULOSIN DERIVATIVE

The optically active compound, R (-)-5-[2-[[2-(2-ethoxyphenoxy)ethyl] amino] propyl]-2-hydroxybenzenesulfonamide in good chemical and optical purity, a metabolite of the α1-adrenergic blocking agent tamsulosin, and methods for the preparation thereof. Pharmaceutical compositions including the optically active compound and methods of treatment comprising direct administration of an effective α1-adrenergic antagonistic amount of such compositions to mammals.