112941-26-1

Basic information

• Product Name: o-Carbomethoxybenzyl sulfonamide
• Synonyms: 2-Methyl benzyl sulfonaMide;o-Carbomethoxybenzyl sulfomide;2-(METHYL FORMATE) BENZYL SULFONAMIDE;2-(AMINOSULFONYLMETHYL)BENZOIC ACID METHYL ESTER;2-CARBOMETHOXYBENZYL SULFONAMIDE;METHYL 2-(AMINOSULFONYLMETHYL)BENZOATE;O-CARBOMETHOXYBENZYL SULFONAMIDE;2-(Methyl formate)benzyl sulfonamie
• CAS NO: 112941-26-1
• Molecular Formula: C₉H₁₁NO₄S
• Molecular Weight: 229.25
• EINECS: 419-010-5
• Product Categories: Esters;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het
• Mol File: 112941-26-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 100 °C
• Boiling Point: 429.8 °C at 760 mmHg
• Flash Point: 213.7 °C
• Appearance: white crystal
• Density: 1.361 g/cm³
• Vapor Pressure: 1.37E-07mmHg at 25°C
• Refractive Index: 1.566
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly)
• PKA: 10.15±0.60(Predicted)
• CAS DataBase Reference: o-Carbomethoxybenzyl sulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: o-Carbomethoxybenzyl sulfonamide(112941-26-1)
• EPA Substance Registry System: o-Carbomethoxybenzyl sulfonamide(112941-26-1)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 112941-26-1(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline

Uses

o-Carbomethoxybenzyl Sulfonamide is a useful reactant in organic synthesis.

InChI:InChI=1/C9H11NO4S/c1-14-9(11)8-5-3-2-4-7(8)6-15(10,12)13/h2-5H,6H2,1H3,(H2,10,12,13)

Synthetic route

2-(Chlorosulfonylmethyl)benzoic acid methyl ester (103342-27-4) → methyl 2-[(aminosulfonyl)methyl]benzoate (112941-26-1)

Conditions	Yield
With ammonia; acetic acid In 1,2-dichloro-benzene at 10 - 50℃; for 5h; Temperature;	95%
Multi-step reaction with 2 steps 1: 440 mg / ethyl acetate / 3 h / 0 - 20 °C 2: 255 mg / trifluoroacetic acid / 3 h / 20 °C View Scheme

2-(tert-butylsulfamoyl-methyl)-benzoic acid methyl ester (415916-11-9) → methyl 2-[(aminosulfonyl)methyl]benzoate (112941-26-1)

Conditions	Yield
With trifluoroacetic acid at 20℃; for 3h;	255 mg

ortho-methylbenzoic acid (118-90-1) → methyl 2-[(aminosulfonyl)methyl]benzoate (112941-26-1)

Conditions	Yield
Multi-step reaction with 5 steps 1: 2,2'-azobis(isobutyronitrile); thionyl chloride / 1,2-dichloro-ethane / 4 h / 60 °C 2: sulfuric acid / 6 h / 80 °C 3: sodium thiosulfate / water / 3 h / 70 °C 4: water; chlorine / 1,2-dichloro-benzene / 5 h / 10 - 30 °C 5: ammonia; acetic acid / 1,2-dichloro-benzene / 5 h / 10 - 50 °C View Scheme

2-(chloromethyl)benzoic acid (85888-81-9) → methyl 2-[(aminosulfonyl)methyl]benzoate (112941-26-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid / 6 h / 80 °C 2: sodium thiosulfate / water / 3 h / 70 °C 3: water; chlorine / 1,2-dichloro-benzene / 5 h / 10 - 30 °C 4: ammonia; acetic acid / 1,2-dichloro-benzene / 5 h / 10 - 50 °C View Scheme

o-(chloromethyl)benzoic acid methyl ester (34040-62-5) → methyl 2-[(aminosulfonyl)methyl]benzoate (112941-26-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium thiosulfate / water / 3 h / 70 °C 2: water; chlorine / 1,2-dichloro-benzene / 5 h / 10 - 30 °C 3: ammonia; acetic acid / 1,2-dichloro-benzene / 5 h / 10 - 50 °C View Scheme

tert-butyldimethylsilyl chloride (18162-48-6) + methyl 2-[(aminosulfonyl)methyl]benzoate (112941-26-1) → methyl 2-((N-(tert-butyldimethylsilyl)sulfamoyl)methyl)benzoate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 24h;	100%

1-[3-cyano-5-(ethoxycarbonyl)-6-methylpyridine-2-yl]azetidine-3-carboxylic acid (898227-90-2) + methyl 2-[(aminosulfonyl)methyl]benzoate (112941-26-1) → 5-cyano-6-[3-(2-methoxycarbonyl-phenylmethanesulfonylaminocarbonyl)-azetidin-1-yl]-2-methyl-nicotinic acid ethyl ester

Conditions	Yield
With triethylamine; HATU In N,N-dimethyl-formamide at 20℃;	50%

succinic acid anhydride (108-30-5) + methyl 2-[(aminosulfonyl)methyl]benzoate (112941-26-1) → 4-({[2-(methoxycarbonyl)benzyl]sulfonyl}amino)-4-oxobutanoic acid

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 22℃; for 2h;	100 mg

methyl 2-[(aminosulfonyl)methyl]benzoate (112941-26-1) + 4,6-dimethoxy-2-isothiocyanatopyrimidine (110860-38-3) → N-(2-Methoxycarbonylbenzyl)sulfonyl-N'-(4,6-dimethoxy-2-pyrimidinyl) thiourea

Conditions	Yield
With potassium carbonate In water; acetone

methyl 2-[(aminosulfonyl)methyl]benzoate (112941-26-1) → 2-[(Aminosulfonyl)methyl]benzoic acid hydrazide

Conditions	Yield
With hydrazine hydrate In ethanol; water

methyl 2-[(aminosulfonyl)methyl]benzoate (112941-26-1) → methyl 2-((N'-(tert-butyldimethylsilyl)sulfamidimidoyl)methyl)benzoate

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 24 h / 20 °C 2: dichlorotriphenylphosphorane; 2,6-dimethylpyridine / dichloromethane; chloroform / 0 - 20 °C / Inert atmosphere View Scheme

methyl 2-[(aminosulfonyl)methyl]benzoate (112941-26-1) → 2-((tert-butyldimethylsilyl)imino)-2,3-dihydro-2λ4-benzo[d][1,2]thiazin-4(1H)-one 2-oxide

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 24 h / 20 °C 2: dichlorotriphenylphosphorane; 2,6-dimethylpyridine / dichloromethane; chloroform / 0 - 20 °C / Inert atmosphere 3: sodium methylate / methanol / 1 h / 0 °C / Inert atmosphere View Scheme

methyl 2-[(aminosulfonyl)methyl]benzoate (112941-26-1) → 2-imino-2,3-dihydro-2λ4-benzo[d][1,2]thiazin-4(1H)-one 2-oxide

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 24 h / 20 °C 2: dichlorotriphenylphosphorane; 2,6-dimethylpyridine / dichloromethane; chloroform / 0 - 20 °C / Inert atmosphere 3: sodium methylate / methanol / 1 h / 0 °C / Inert atmosphere 4: hydrogenchloride / methanol; water / 0.33 h / 0 °C View Scheme

methyl 2-[(aminosulfonyl)methyl]benzoate (112941-26-1) → 1-(1,2,3,5,6,7-hexahydro-s-indacen-4-yl)-3-(2-oxido-4-oxo-3,4-dihydro-1H-2λ4-benzo[d][1,2]thiazin-2-ylidene)urea

Conditions

Yield

Multi-step reaction with 5 steps 1.1: triethylamine / dichloromethane / 24 h / 20 °C 2.1: dichlorotriphenylphosphorane; 2,6-dimethylpyridine / dichloromethane; chloroform / 0 - 20 °C / Inert atmosphere 3.1: sodium methylate / methanol / 1 h / 0 °C / Inert atmosphere 4.1: hydrogenchloride / methanol; water / 0.33 h / 0 °C 5.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C / Inert atmosphere 5.2: 2 h / 20 °C View Scheme

Upstream product

• 34040-62-5 o-(chloromethyl)benzoic acid methyl ester 
• 85888-81-9 2-(chloromethyl)benzoic acid 
• 118-90-1 ortho-methylbenzoic acid 
• 103342-27-4 2-(Chlorosulfonylmethyl)benzoic acid methyl ester 
• 415916-11-9 [[((1,1-dimethylethyl)amino)sulfonyl]methyl]benzoic acid methyl ester 

Relevant articles and documents

Synthesis method of O-formate benzyl sulfonamide

The invention discloses a synthesis method of ortho-formate benzyl sulfonamide, and relates to the technical field of battery electrolyte additives. The method comprises the following steps: taking 2 - chloromethyl benzoate as a raw material, and performing nucleophilic substitution reaction. The oxidation chlorination reaction, the ammoniation reaction and the tert-butyl protection are obtained, that is, the ortho-formate benzyl sulfonamide. To the invention, a plurality of reaction kettles are used for gradually synthesizing the ortho-formate benzyl sulfonamide, the direct connection relation between each product is isolated, the influence of byproducts generated by the solvent on different reactions is avoided, and the purity of the product is further improved by adopting a method of distilled water washing, ethyl acetate extraction and anhydrous magnesium sulfate drying. The total yield of the synthesis method reaches above 59.96%, and the purity of the ortho-formate benzyl sulfonamide reaches 99.5% or above.

Development of an immunoassay for the residues of the herbicide bensulfuron-methyl.

To develop a competitive indirect enzyme-linked immunosorbent assay based on polyclonal antibodies for the detection of the sulfonylurea herbicide bensulfuron-methyl, seven structurally related haptens were synthesized. Four of them mimicking the target analyte were conjugated to keyhole limpet hemocyanin by the N-hydroxysuccinimide activated ester method to use as immunogens, and all of them were conjugated to bovine serum albumin to use as plate-coating antigens. Polyclonal antibodies raised in rabbits and the coating antigens were screened and selected for the assay in simple homologous and heterologous ELISA formats. Three sensitive heterologous ELISAs were selected and optimized, showing the average IC(50) values of bensulfuron-methyl as low as 0.17, 0.09, and 0.09 ng/mL, the detection ranges of 0.04-0.60, 0.01-0.60, and 0.04-0.25 ng/mL, and the lowest detection limits of 0.03, 0.002, and 0.03 ng/mL, respectively. The cross-reactivities of other sulfonylurea herbicides and metabolites of bensulfuron-methyl to the antibodies were less than 15% in the two assays. Recoveries from the analyte-fortified water samples in assay I were in the range of 81-125% by simple dilution. The correlation between the ELISA and HPLC was 0.999 (n = 15) with a slope of 1.37 in the analysis of groundwater samples fortified with bensulfuron-methyl. The results obtained strongly indicate that the ELISA can be a highly sensitive and convenient tool for detecting bensulfuron-methyl residues in agricultural and environmental samples.