710-24-7

Usage

Chemical Properties

White Solid

Uses

P-Acetamidobenzenesulfinic Acid is a component used in the preparation of Cyanine dyes.

Synthetic route

Acetanilid (103-84-4) → 4-acetamidobenzenesulfinic acid (710-24-7)

Conditions	Yield
With hydrogenchloride; aluminium(III) triflate; sulfur dioxide In ethanol at 0℃; under 7600.51 Torr; for 50h; Pressure; Temperature;	94%
With sulfur dioxide at 90℃; for 1h; Reagent/catalyst; Temperature; Inert atmosphere;	94.07%

p-acetylaminobenzenesulfonyl chloride (121-60-8) → 4-acetamidobenzenesulfinic acid (710-24-7)

Conditions	Yield
With sodium hydrogencarbonate; sodium sulfite In water at 70 - 80℃; for 1h; Reduction;	72%
With triethylamine; para-thiocresol In dichloromethane at -76℃; for 0.25h;	64%
With sodium sulfite

o-nitrophenyl N-acetylthiosulfanilate (18522-22-0) + N,N'-diethyl-N,N'-diphenylmethionamide (77505-27-2) → 4-acetamidobenzenesulfinic acid (710-24-7) + (2-Nitro-phenylsulfanyl)-methanedisulfonic acid bis-(ethyl-phenyl-amide)

Conditions	Yield
With potassium 1) toluene, 2) 70 deg C, 10 h, boiling water bath, 1 h; Yield given. Multistep reaction;	A n/a B 49%
With potassium 1) toluene, 2) 70 deg C, 10 h, boiling water bath, 1 h; Yield given. Multistep reaction;	A 48% B n/a

4-acetamidobenzenesulfonylhydrazine (3989-50-2) → 4-acetamidobenzenesulfinic acid (710-24-7)

Conditions	Yield
With sodium hydroxide

acetic acid-[4-(3-oxo-3-phenyl-propane-1-sulfonyl)-anilide] (87015-43-8) → 4-acetamidobenzenesulfinic acid (710-24-7) + Phenyl vinyl ketone (768-03-6)

Conditions	Yield
With sodium hydroxide In acetone at 20℃; Rate constant; Equilibrium constant;
With potassium dihydrogenphosphate; acetaldehyde; citric acid; NADH; aldehyde dehydrogenase In water at 20℃; Rate constant;

acetic acid-[4-(2-nitro-1-phenyl-ethanesulfonyl)-anilide] (87015-50-7) → (2-nitroethenyl)benzene (102-96-5) + 4-acetamidobenzenesulfinic acid (710-24-7)

Conditions	Yield
With sodium hydroxide In acetone at 20℃; Rate constant; Equilibrium constant;

di-isopropyl azodicarboxylate (2446-83-5) + 4-acetamidobenzenesulfinic acid (710-24-7) → diisopropyl 1-(4-acetamidophenylsulfonyl)hydrazine-1,2-dicarboxylate

Conditions	Yield
In methanol at 20℃; for 12h; Green chemistry;	97%

1-ethenyl-2-pyrrolidinone (88-12-0) + 4-acetamidobenzenesulfinic acid (710-24-7) → N-(4-((1-(2-oxopyrrolidin-1-yl)ethyl)sulfonyl)phenyl)acetamide

Conditions	Yield
With photoredox catalyst Ni/TiO2 In acetonitrile at 20℃; for 12h; Molecular sieve; Irradiation;	90%

3-(3-phenylpropyl-2-yn-1-ylidene)-2,4-pentanedione (67082-95-5) + 4-acetamidobenzenesulfinic acid (710-24-7) → N-(4-(((4-acetyl-5-methylfuran-2-yl)(phenyl)methyl)sulfonyl)phenyl)acetamide

Conditions	Yield
With air In water at 80℃; for 3h;	82%

4-methyl-β-nitrostyrene (7559-36-6) + 4-acetamidobenzenesulfinic acid (710-24-7) → N-[4-(2-Nitro-1-p-tolyl-ethanesulfonyl)-phenyl]-acetamide

Conditions	Yield
In ethanol for 24h;	80%

4-acetamidobenzenesulfinic acid (710-24-7) + 1,3-Dimethoxybenzene (151-10-0) → N-(4-((2,4-dimethoxyphenyl)sulfinyl)phenyl)acetamide

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 30℃; for 0.833333h;	77%

4-acetamidobenzenesulfinic acid (710-24-7) + 1-nitro-4-phenyl-but-3-en-2-one (103264-16-0) → 1-nitro-4-phenyl-4-(p-acetanilidosulfonyl)-2-butanone (106148-72-5)

Conditions	Yield
In ethanol Ambient temperature;	40%

2-vinylpyridine (100-69-6) + 4-acetamidobenzenesulfinic acid (710-24-7) → acetic acid-[4-(2-[2]pyridyl-ethanesulfonyl)-anilide] (108838-79-5)

Conditions	Yield
With ethanol; water
With water

4-vinylpyridine (100-43-6) + 4-acetamidobenzenesulfinic acid (710-24-7) → N-[4-(2-pyridin-4-yl-ethanesulfonyl)-phenyl]-acetamide (741201-50-3)

Conditions	Yield
With water

2-chloro-4,5-dimethyl-1,3-thiazole (56355-41-0) + 4-acetamidobenzenesulfinic acid (710-24-7) → acetic acid-[4-(4,5-dimethyl-thiazole-2-sulfonyl)-anilide]

Conditions	Yield
With pyridine

6-Chloro-pyridin-3-ylamine (5350-93-6) + 4-acetamidobenzenesulfinic acid (710-24-7) → 6-(N-acetyl-sulfanilyl)-[3]pyridylamine

Conditions	Yield
With methanol at 160℃;

2-iodo-propane (75-30-9) + 4-acetamidobenzenesulfinic acid (710-24-7) → N-(4-(isopropylsulfonyl)phenyl)acetamide (86810-72-2)

Conditions	Yield
With sodium hydroxide

Upstream product

• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 3989-50-2 4-acetamidobenzenesulfonylhydrazine 
• 18522-22-0 o-nitrophenyl N-acetylthiosulfanilate 
• 77505-27-2 N,N'-diethyl-N,N'-diphenylmethionamide 
• 3660-40-0 S-phenyl 4-acetamidobenzenesulfonothioate 
• 64-17-5 ethanol 
• 1241-00-5 4'-acetamidophenyl-4-acetamidobenzene thiolsulfonate 
• 1126-81-4 4-acetamidothiophenol 
• 103-84-4 Acetanilid 
• 87015-50-7 acetic acid-[4-(2-nitro-1-phenyl-ethanesulfonyl)-anilide] 
• 87015-43-8 acetic acid-[4-(3-oxo-3-phenyl-propane-1-sulfonyl)-anilide] 

Downstream Products

• 108838-79-5 acetic acid-[4-(2-[2]pyridyl-ethanesulfonyl)-anilide] 
• 741201-50-3 N-[4-(2-pyridin-4-yl-ethanesulfonyl)-phenyl]-acetamide 
• 86810-72-2 N-(4-(isopropylsulfonyl)phenyl)acetamide 
• 93476-68-7 N-[4-(benzothiazole-2-sulfonyl)-phenyl]-acetamide 
• 5702-78-3 1-methyl-4-nitro-5-[4-acetamido(phenylsulfonyl)]-1H-imidazole 
• 860542-31-0 acetic acid-[4-(2,4,6-trinitro-benzenesulfonyl)-anilide] 
• 109098-80-8 acetic acid-(4-bromomethanesulfonyl-anilide) 
• 3466-30-6 acetic acid-[4-(2-phenyl-ethenesulfonyl)-anilide] 
• 101513-55-7 4'-acetamino-2-methylcarbonyl-4-nitro-diphenylsulfone 

Relevant academic research and scientific papers

Sulfination of acetanilide using liquid coordination complexes as dual catalyst and solvent

The Freidel-Crafts sulfination reaction of acetanilide with sulfur dioxide was catalyzed by several AlCl3-based liquid coordination complexes (LCCs), and the results were compared with that catalyzed by traditional ILs. Influences of different catalysts, ligand/AlCl3 molar ratios, and reaction conditions on their catalytic performance were investigated. The optimal result was obtained using acetamide-AlCl3-based LCC (molar ratio of acetamide to AlCl3 was 0.65, marked as 0.65 A A/AlCl3) as the catalyst, giving nearly 100% conversion of acetanilide within 60 min and 94.07% of selectivity to 4-acetamidobenzenesulfinic acid. AA/AlBr3 was synthesized and also showed catalytic activity for the sulfination reaction. Then a plausible reaction mechanism was proposed by investigation through the raman spectra.

Method for preparing 4-acetamidobenzene sulfinic acid

The invention belongs to the field of organic synthesis, and relates to a method for preparing 4-acetamidobenzene sulfinic acid. The method comprises the steps: taking acetanilide and sulfur dioxide as raw materials, ionic liquid as a catalyst and the third dispersed phase particles as an accelerant, carrying out catalytic reaction in a closed reaction kettle with a self-suction stirring device to obtain the 4-acetaminobenzene sulfinic acid with high yield. According to the method disclosed by the invention, the reaction time can be remarkably shortened, and the yield of the 4-acetaminobenzene sulfinic acid can reach 89.6%.

Method for synthesizing aryl sulfonic acid by utilizing sulfur dioxide

The invention relates to a method for synthesizing aryl sulfonic acid by utilizing sulfur dioxide. The method is characterized by comprising the following steps that S1, aromatic hydrocarbon is added into a solvent, stirring is performed to achieve complete dissolution, and then a catalyst is added; S2, under the stirring condition and the conditions of 0-100 DEG C and 0-10 atm, dried excessive sulfur dioxide gas or sulfur dioxide liquid are added, and reaction is performed for 0.5-50 hours; S3, the reaction liquid obtained in the step S2 is cooled to 10 DEG C or below, pressurized filtration is performed, and a catalyst is recovered; S4, filtrate is distilled to recover unreacted sulfur dioxide, then the solvent is recovered through distillation, the residual solid is the product aryl sulfonic acid, and the product yield is higher than 85%. The raw materials for the method for synthesizing the aryl sulfonic acid by utilizing the sulfur dioxide are cheap and easy to obtain, the product yield is high, the production process is safer, ad the severe environmental pollution of a traditional process is greatly reduced.

Phenylsulfonylnitromethanes as potent irreversible inhibitors of aldose reductase

Aldose reductase (AR) inhibition provides a viable pharmacologically direct mode for the treatment of diabetic complications. We have synthesized a series of N-4 substituted analogues (15-21) of the known aldose reductase inhibitor phenyl-sulfonylnitromethane. The compounds are potent inhibitors of AR with IC50s between 0.01 and 0.19 μM. Some of the compounds are also potent affinity labels for AR. Compound 19 exhibits the highest and almost complete irreversible inhibition of AR known to date.

Substituted benzene derivatives useful as neuraminidase inhibitors

A compound of the Formula (I): STR1 or pharmaceutically-suitable salts or prodrug forms thereof, wherein: n is 0-1; m is 0; p is 0-1; R1 is --CO2 H; R2 is selected from the group consisting of H, --OH, and --NH2 ; R3 is H; R4 is --C(O)NHR8 ; R5 is --NHC(R6)NH2 R6 is selected from the group consisting of =NH, =NOH, =NCN, =O, and =S; and R8 is selected from the group consisting of C1 -C4 linear or branched alkyl substituted with 0-3 halogens on each carbon.

Sulfinic Acids and Related Compounds 23. Preparation of Sulfinic Acids by the Reaction of Sulfonyl Halides with Thiols

The reaction of arene- and alkanesulfonyl halides with p-thiocresol in the presence of triethylamine at -76 deg C gives triethylammonium sulfinates, which after acidification afford sulfinic acids of 95 - 100 percent purity in yields of 51 - 92 percent for 18 typical representatives.The synthesis succeeds in certain instances where conventional reduction with aqueous sodium sulfite fails and in other instances often is superior.The method is rapid, mild, selective, convenient, and general, although a few limitations are reported.Characterizations of the sulfinic acids are effected by titration with aqueous sodium nitrite, by IR and 1H-NMR spectra, by preparation of either a S-benzylthiuronium salt or a p-nitrobenzyl ester and either by elemental analyses or comparison with reported melting points of the acids and derivatives as appropriate.

DERIVATIVES OF METHIONIC ACID. III. CHEMICAL CHARACTERISTICS OF N,N'-DIETHYL-N,N'-DIPHENYLMETHIONAMIDE

The action of alkyl iodides on the potassium derivative of N,N'-diethyl-N,N'diphenylmethionamide (methionide) leads to the formation of N,N'-diethyl-N,N'-diphenylamides of mono- and dialkylmethionic acids; the action of sulfonyl and sulfenyl chlorides on potassiomethionide gives sulfones and sulfides, respectively; the latter are also formed in its reaction with thiosulfonic esters.Unlike diphenyl methionate, methionide does not react with aldehydes and sulfoxides and hardly reacts with p-nitrobenzenediazonium chloride.

Syntheses of Some Alkyl-, Cycloalkyl-, and Aryl-(4-aminophenyl)-sulfones

Syntheses of (4-aminophenyl)-alkyl, -cycloalkyl and -aryl sulfones 2 were achieved both by alkylation of 4-(acetylamino)-benzenesulfinic acid (7) to the corresponding acetanilides 9 followed by hydrolysis and by oxidation of the appropriate (4-nitrophenyl)-sulfides 11 to (4-nitrophenyl)-sulfones 1 with subsequent Bechamp reduction.