N-(4-Acetylphenyl)methanesulfonamide supplier

Name
N-(4-Acetylphenyl)methanesulfonamide
EINECS
CAS No. 5317-89-5
Article Data29
CAS DataBase
Density 1.32 g/cm³
Solubility
Melting Point 150-152 °C
Formula C₉H₁₁NO₃S
Boiling Point 369.4 °C at 760 mmHg
Molecular Weight 213.257
Flash Point 177.2 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols Xi
Synonyms Methanesulfonamide, N-(4-acetylphenyl)-;N-(4-Acetyl-phenyl)-methanesulfon-amide;
PSA 71.62000
LogP 2.41450

Synthetic route

: 99-92-3
4-Aminoacetophenone

: 124-63-0
methanesulfonyl chloride

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 23h; Inert atmosphere;	100%
With pyridine In dichloromethane at 0 - 20℃; for 16h;	98%
In dichloromethane at 20 - 25℃; for 1h; Large scale;	96%

: 3144-09-0
methanesulfonamide

: 99-90-1
para-bromoacetophenone

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

Conditions

Conditions	Yield
With potassium phosphate; copper(l) iodide; dimethylaminoacetic acid In N,N-dimethyl-formamide for 48h; Heating;	96%
With bis(η3-allyl-μ-chloropalladium(II)); potassium carbonate; tert-butyl XPhos In 2-methyltetrahydrofuran at 80℃; for 6h; Inert atmosphere;	95%
With di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; bis(η3-allyl-μ-chloropalladium(II)); sodium t-butanolate In water at 50℃; for 24h; Inert atmosphere; Green chemistry;	85%

: N-(4-acetylphenyl)-N-(methylsulfonyl)methanesulfonamide

A: 1-[4-amino-3-(methylsulfonyl) phenyl] ethanone

B: 5317-89-5
4'-(methylsulfonylamino)acetophenone

C: 5470-49-5
4-methanesulfonylphenylamine

D: 99-92-3
4-Aminoacetophenone

Conditions

Conditions	Yield
In acetonitrile for 24h; Inert atmosphere; Irradiation;	A 26% B 12% C 5% D 30%

...Expand

: 1197-22-4
N-phenylmethanesulfonamide

: 108-24-7
acetic anhydride

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

Conditions

Conditions	Yield
With aluminium trichloride In 1,2-dichloro-ethane Friedel-Crafts acylation;

: 99-92-3
4-Aminoacetophenone

: 7143-01-3
Methanesulfonic anhydride

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

Conditions

Conditions	Yield
With pyridine; sodium hydrogencarbonate In dichloromethane

: 4'-acetyl-2'-bromomethanesulfonanilide

: 367-27-1
2,4-difluorophenol

A: 5317-89-5
4'-(methylsulfonylamino)acetophenone

B: 4'-acetyl-2'-(2,4-difluorophenoxy)methanesulfonanilide

Conditions

Conditions	Yield
With pyridine; potassium carbonate; copper(l) chloride at 115℃; for 6h; Reagent/catalyst; Time; Ullmann Condensation; Inert atmosphere; Large scale;	A 35 %Chromat. B 54 %Chromat.

...Expand

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: N-[4-(1-hydrazonoethyl)phenyl]methanesulfonamide

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate; hydrazine In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;	99%

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 4'-acetyl-2'-bromomethanesulfonanilide

Conditions

Conditions	Yield
With bromine; acetic acid In water at 15℃; for 7h; Large scale; regiospecific reaction;	97%

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 74-88-4
methyl iodide

: N-(4-acetyl-phenyl)-N-methyl-methanesulfonamide

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 12h;	93%

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 5577-42-4
N-[4-(2-bromoacetyl)phenyl]methanesulfonamide

Conditions

Conditions	Yield
With bromine; acetic acid at 55℃; for 0.25h; regiospecific reaction;	92%
With aluminium trichloride; bromine In chloroform at 0℃; for 0.5h;	81%
With tetra-N-butylammonium tribromide In methanol; dichloromethane at 20℃; for 19h; Inert atmosphere;	60%

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 4'-(methylsulfonylamino)acetophenone oxime

Conditions

Conditions	Yield
With pyridine; hydroxylamine hydrochloride at 70℃; for 3h;	91%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 401909-82-8
N-[4-(1-hydroxyimino-ethyl)-phenyl]-methanesulfonamide

Conditions

Conditions	Yield
With pyridine; hydroxylamine hydrochloride	88%
With hydrogenchloride; hydroxylamine; sodium acetate
With pyridine; hydroxylamine hydrochloride at 70℃; for 3h;
With pyridine; hydroxylamine hydrochloride

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 1383579-32-5
4-amino-5-(hydroxymethyl)-2-(methylthio)furo[2,3-d]pyrimidine

: 1383579-39-2
N-(4-acetylphenyl)-N-({4-amino-2-(methylthio)furo[2,3-d]pyrimidin-5-yl}methyl)methanesulfonamide

Conditions

Conditions	Yield
Stage #1: 4'-(methylsulfonylamino)acetophenone With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0℃; for 0.166667h; Mitsunobu reaction; Stage #2: 4-amino-5-(hydroxymethyl)-2-(methylthio)furo[2,3-d]pyrimidine In tetrahydrofuran at 0 - 20℃; Mitsunobu reaction;	78%

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 86-81-7
3,4,5-trimethoxy-benzaldehyde

: N-(4-(3-(3,4,5-trimethoxyphenyl)acryloyl)phenyl)methanesulfonamide

Conditions

Conditions	Yield
With sodium hydroxide In ethanol at 20℃;	78%

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 104-88-1
4-chlorobenzaldehyde

: N-(4-(3-(4-chlorophenyl)acryloyl)phenyl)methanesulfonamide

Conditions

Conditions	Yield
With sodium hydroxide In ethanol at 20℃;	75%

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 555-16-8
4-nitrobenzaldehdye

: N-(4-(3-(4-nitrophenyl)acryloyl)phenyl)methanesulfonamide

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃;	75%

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 17852-67-4
4-(methylsulfonyl)phenylhydrazine hydrochloride

: (E)-N-(4-(1-(2-(4-(methylsulfonyl)phenyl)hydrazono)ethyl)phenyl)methanesulfonamide

Conditions

Conditions	Yield
In ethanol for 12h; Reflux;	66%

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 124-63-0
methanesulfonyl chloride

: N-(4-acetylphenyl)-N-(methylsulfonyl)methanesulfonamide

Conditions

Conditions	Yield
With sodium hydroxide In water for 0.5h;	59%

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 107-21-1
ethylene glycol

: N-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)methanesulfonamide

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 18h; Dean-Stark; Reflux;	56%

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 459-57-4
4-fluorobenzaldehyde

: N-{4-[3-(4-fluoro-phenyl)-acryloyl]-phenyl}-methanesulfonamide

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 25℃; Claisen-Schmidt condensation;	52%

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 100-52-7
benzaldehyde

: N-(4-cinnamoylphenyl)methanesulfonamide

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 25℃; Claisen-Schmidt condensation;	51%

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 104-87-0
4-methyl-benzaldehyde

: N-[4-(3-p-tolyl-acryloyl)-phenyl]-methanesulfonamide

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 25℃; Claisen-Schmidt condensation;	45%

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 3930-20-9, 27948-47-6, 30236-31-8, 30236-32-9
sotalol

Conditions

Conditions	Yield
Stage #1: 4'-(methylsulfonylamino)acetophenone With iodine; dimethyl sulfoxide at 120℃; Stage #2: With isopropylamine In 1,2-dichloro-ethane at 25℃; for 2h; Stage #3: With sodium tetrahydroborate In 1,2-dichloro-ethane at 0℃; for 2h;	45%

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 123-11-5
4-methoxy-benzaldehyde

: N-(4-(3-(4-methoxyphenyl)acryloyl)phenyl)methanesulfonamide

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 25℃; Claisen-Schmidt condensation;	44%

: 123-75-1
pyrrolidine

: 50-00-0
formaldehyd

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 76467-72-6
4'-[3-(1-pyrrolidinyl)propionyl]methanesulfonanilide

Conditions

Conditions	Yield
In ethanol; water at 100℃; for 50h;	17%

...Expand

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 10111-08-7
2-imidazolecarbaldehyde

: (E)‐N‐(4‐(3‐(1H‐imidazol‐2‐yl)acryloyl)phenyl)methanesulfonamide

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water at 60℃; for 7h; Michael Addition;	15%

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 61560-92-7
(4-Methanesulfonylamino-phenyl)-oxo-acetic acid

Conditions

Conditions	Yield
With pyridine; selenium(IV) oxide

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 130350-69-5
bis(ethylheptylamino)methane

: N-{4-[3-(Ethyl-heptyl-amino)-propionyl]-phenyl}-methanesulfonamide; hydrochloride

Conditions

Conditions	Yield
With acetyl chloride 1.) THF, RT, 45 min, 2.) RT, 3 d; Yield given. Multistep reaction;

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 100-39-0
benzyl bromide

: 110698-70-9
N-<4-(1-oxoethyl)phenyl>-N-(phenylmethyl)methanesulfonamide

Conditions

Conditions	Yield
With sodium methylate 1.) methanol, RT, 30 min, 2.) methanol, RT, 28 h; Yield given. Multistep reaction;

: 5317-89-5
4'-(methylsulfonylamino)acetophenone

: 919122-30-8
4-methylsulfonamidophenacyl phenylacetate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / bromine; AlCl3 / CHCl3 / 0.5 h / 0 °C 2: 81 percent / triethylamine / acetonitrile / 1 h / 25 °C View Scheme

N-(4-Acetylphenyl)methanesulfonamide Specification

The CAS register number of N-(4-Acetylphenyl)methanesulfonamide is 5317-89-5. It also can be called as Methanesulfonamide, N-(4-acetylphenyl)- and the systematic name about this chemical is N-(4-acetylphenyl)methanesulfonamide. The molecular formula about this chemical is C₉H₁₁NO₃S and molecular weight is 213.25.

Physical properties about N-(4-Acetylphenyl)methanesulfonamide are: (1)ACD/LogP: 0.66; (2)#H bond acceptors: 4; (3)#H bond donors: 1; (4)#Freely Rotating Bonds: 2; (5)Polar Surface Area: 62.83Å²; (6)Index of Refraction: 1.573; (7)Molar Refractivity: 53.21 cm³; (8)Molar Volume: 161.4 cm³; (9)Polarizability: 21.09x10^-24cm³; (10)Surface Tension: 52.4 dyne/cm; (11)Flash Point: 177.2 °C; (12)Enthalpy of Vaporization: 61.62 kJ/mol; (13)Boiling Point: 369.4 °C at 760 mmHg; (14)Vapour Pressure: 1.19E-05 mmHg at 25°C.

Preparation: this chemical can be prepared by 1-(4-amino-phenyl)-ethanone and methanesulfonyl chloride. This reaction will need reagent Py.

You can still convert the following datas into molecular structure:
(1)SMILES: O=S(=O)(Nc1ccc(cc1)C(=O)C)C
(2)InChI: InChI=1/C9H11NO3S/c1-7(11)8-3-5-9(6-4-8)10-14(2,12)13/h3-6,10H,1-2H3
(3)InChIKey: BQBFGIIQPXLTKM-UHFFFAOYAW
(4)Std. InChI: InChI=1S/C9H11NO3S/c1-7(11)8-3-5-9(6-4-8)10-14(2,12)13/h3-6,10H,1-2H3
(5)Std. InChIKey: BQBFGIIQPXLTKM-UHFFFAOYSA-N

Product Name

N-(4-Acetylphenyl)methanesulfonamide

Synthetic route

N-(4-Acetylphenyl)methanesulfonamide Specification

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