1561-92-8

Basic information

• Product Name: Sodium 2-methylprop-2-ene-1-sulfonate
• Synonyms: 2-methyl-2-propene-1-sulfonicacisodiumsalt;2-Propene-1-sulfonicacid,2-methyl-,sodiumsalt;methallylsulfonate;sodiummethallylsulfonate(35%);SODIUM METHALLYLSULFONATE;SODIUM 2-METHYL-2-PROPENE-1-SULFONATE;2-METHYL-2-PROPENE-1-SULFONIC ACID SODIUM SALT;1-(2-METHYL-2-PROPENE)SULFONIC ACID SODIUM SALT
• CAS NO: 1561-92-8
• Molecular Formula: C₄H₇O₃S*Na
• Molecular Weight: 158.15
• EINECS: 216-341-5
• Product Categories: Sulfonic/Sulfinic Acid Salts;Organic Building Blocks;Sulfur Compounds
• Mol File: 1561-92-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: >300 °C(lit.)
• Appearance: White flakes crystal
• Density: 1.26g/cm3
• Vapor Pressure: 0Pa at 20℃
• Refractive Index: 1.475
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: 523g/L at 20℃
• CAS DataBase Reference: Sodium 2-methylprop-2-ene-1-sulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium 2-methylprop-2-ene-1-sulfonate(1561-92-8)
• EPA Substance Registry System: Sodium 2-methylprop-2-ene-1-sulfonate(1561-92-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37
• WGK Germany: 1
• Hazardous Substances Data: 1561-92-8(Hazardous Substances Data)

Usage

Uses

2-Methyl-2-propene-1-sulfonic acid sodium salt was used as anionic monomer to investigate the effect of different cationic or anionic moieties in acrylonitrile-based copolymers on the interaction with fibroblasts. It was used to reduce the homopolymerization during graft copolymerization of methyl methacrylate with water-emulsified solution onto preirradiated jute fiber.

Flammability and Explosibility

Flammable

Synthesis

The synthesis of?2-METHYL-2-PROPENE-1-SULFONIC ACID SODIUM SALT is as follows:The neutralization was carried out with sodium carbonate to pH 7. The neutralized filtrate was evaporated under reduced pressure (20 mmHg) to remove water and to obtain 46.5 g of white crystalline sodium methallyl sulfonate. The product was identified with a standard sample by IR spectrum. The purity of the product was 95.5% and the yield 95%.

InChI:InChI=1/C4H8O3S/c1-4(2)3-8(5,6)7/h1,3H2,2H3,(H,5,6,7)

Synthetic route

2-methyl-prop-2-ene-1-sulfonic acid (3934-16-5) → sodium methallylsulfonate (1561-92-8)

Conditions	Yield
With sodium hydroxide In water at 50℃; for 0.2h; Product distribution / selectivity;

sulfur trioxide -N-tert-butylacetamide + N-tert-butylacetamide (762-84-5) + isobutene (115-11-7) → sodium methallylsulfonate (1561-92-8)

Conditions	Yield
With sodium hydroxide; sulfur trioxide In 1,2-dichloro-ethane

N-tert-butylpropionamide (1118-32-7) → sodium methallylsulfonate (1561-92-8)

3-Chloro-2-methylpropene (563-47-3) → sodium methallylsulfonate (1561-92-8)

Conditions	Yield
With sodium sulfite In ethanol; water for 18h; Reflux;

sodium methallylsulfonate (1561-92-8) + N-phenylphenylene-1,4-diamine (101-54-2) → N-(4-anilino)phenylisopropenylsulfonamide + 2-methylprop-2-ene-1-sulfonyl chloride (14568-34-4)

Conditions	Yield
With phosphorus pentachloride; triethylamine	A 79% B n/a

6NO3(1-)*H2O*4HO(1-)*4O(2-)*6Bi(3+) + water (7732-18-5) + sodium methallylsulfonate (1561-92-8) + dimethyl sulfoxide (67-68-5) → 90O(2-)*30NO3(1-)*7H2O*76Bi(3+)*18C4H7O3S(1-)*38.5C2H6OS

Conditions	Yield
In neat (no solvent) at 80℃; for 4h;	68%

Isopropylbenzene (98-82-8) + sodium methallylsulfonate (1561-92-8) → 2-(4-isopropyl-phenyl)-2-methyl-propane-1-sulfonic acid

Conditions	Yield
With sulfuric acid; boron trifluoride

tert-butylbenzene (253185-03-4, 253185-04-5) + sodium methallylsulfonate (1561-92-8) → 2-(4-tert-butyl-phenyl)-2-methyl-propane-1-sulfonic acid

Conditions	Yield
With sulfuric acid; boron trifluoride; 1,2-dichloro-ethane

ethylbenzene (100-41-4) + sodium methallylsulfonate (1561-92-8) → 2-(4-ethyl-phenyl)-2-methyl-propane-1-sulfonic acid

Conditions	Yield
With sulfuric acid; boron trifluoride; 1,2-dichloro-ethane

Propylbenzene (103-65-1) + sodium methallylsulfonate (1561-92-8) → 2-methyl-2-(4-propyl-phenyl)-propane-1-sulfonic acid

Conditions	Yield
With sulfuric acid; boron trifluoride

1-butylbenzene (104-51-8) + sodium methallylsulfonate (1561-92-8) → 2-(4-butyl-phenyl)-2-methyl-propane-1-sulfonic acid

Conditions	Yield
With sulfuric acid; boron trifluoride; 1,2-dichloro-ethane

hexylbenzene (1077-16-3) + sodium methallylsulfonate (1561-92-8) → 2-(4-hexyl-phenyl)-2-methyl-propane-1-sulfonic acid

Conditions	Yield
With sulfuric acid; boron trifluoride; 1,2-dichloro-ethane

Octylbenzene (2189-60-8) + sodium methallylsulfonate (1561-92-8) → 2-methyl-2-(4-octyl-phenyl)-propane-1-sulfonic acid

Conditions	Yield
With sulfuric acid; boron trifluoride; 1,2-dichloro-ethane

decylbenzene (104-72-3) + sodium methallylsulfonate (1561-92-8) → 2-(4-decyl-phenyl)-2-methyl-propane-1-sulfonic acid

Conditions	Yield
With sulfuric acid; boron trifluoride; 1,2-dichloro-ethane

tridecylbenzene (123-02-4) + sodium methallylsulfonate (1561-92-8) → 2-methyl-2-(4-tridecyl-phenyl)-propane-1-sulfonic acid

Conditions	Yield
With sulfuric acid; boron trifluoride; 1,2-dichloro-ethane

tery-amylbenzene (2049-95-8) + sodium methallylsulfonate (1561-92-8) → 2-methyl-2-(4-tert-pentyl-phenyl)-propane-1-sulfonic acid

Conditions	Yield
With sulfuric acid; boron trifluoride; 1,2-dichloro-ethane

undecylbenzene (6742-54-7) + sodium methallylsulfonate (1561-92-8) → 2-methyl-2-(4-undecyl-phenyl)-propane-1-sulfonic acid

Conditions	Yield
With sulfuric acid; boron trifluoride; 1,2-dichloro-ethane

sodium methallylsulfonate (1561-92-8) + toluene (108-88-3) → 2-methyl-2-p-tolyl-propane-1-sulfonic acid

Conditions	Yield
With sulfuric acid; boron trifluoride; 1,2-dichloro-ethane

sodium methallylsulfonate (1561-92-8) → 2-methylprop-2-ene-1-sulfonyl chloride (14568-34-4)

Conditions	Yield
With phosphorus pentachloride
With thionyl chloride In N,N-dimethyl-formamide at 20℃; for 4h;
With phosphorus pentachloride In dichloromethane at 20℃; for 16h;	4.672 g

sodium methallylsulfonate (1561-92-8) → sodium 2-methyl-2,3-propanediol-1-sulfonate + Sodium; (2-methyl-oxiranyl)-methanesulfonate

Conditions	Yield
With Oxone In water-d2 for 0.416667h; Product distribution; Ambient temperature; pH 3 to 1; var. olefines;

sodium methallylsulfonate (1561-92-8) → Sodium; (2-methyl-oxiranyl)-methanesulfonate

Conditions	Yield
With magnesium monoperoxyphthalate hexahydrate In water-d2 for 8.5h; Product distribution; Ambient temperature; add of meso-tetrakis-(4-N-methylpyridyl)porphyrinatomanganese(III) chloride: efficient cat. effect; pH 6.5 (phosphate buffer);
With Oxone In water-d2 for 1.08333h; Ambient temperature; pH 6.8 (phosphate buffer); Yield given;
With magnesium monoperoxyphthalate hexahydrate In water-d2 for 8.5h; Ambient temperature; pH 6.5 (phosphate buffer); Yield given;

bromine (7726-95-6) + sodium methallylsulfonate (1561-92-8) + phosphorus tribromide (7789-60-8) → 1,2,3-tribromo-2-methylpropane (631-28-7)

Conditions	Yield
at 85℃;

ammonia (7664-41-7) + sodium methallylsulfonate (1561-92-8) + sodium → isobutene (115-11-7) + Na2SO3

sodium methallylsulfonate (1561-92-8) → sodium 2-methyl-2,3-propanediol-1-sulfonate

Conditions	Yield
With perchloric acid; 2-pyridonato-bridged cis-diammine-Pt(III) dinuclear; sodium perchlorate at 25℃; Kinetics;

maleic anhydride (108-31-6) + sodium persulfate + sodium methallylsulfonate (1561-92-8) → 2-methyl-prop-2-ene-1-sulfonic acid (3934-16-5) + maleic acid (110-16-7)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In water

[(H2O)Pt(NH3)2(μ-α-pyridonato)2-Pt(NH3)2(H2O)] (354566-18-0, 367521-01-5) + sodium methallylsulfonate (1561-92-8) → [Pt2(NH3)4(alpha.-pyridonato)2(CH2C(CH3)(OH)CH2SO3)](2+)

Conditions	Yield
With perchloric acid; sodium perchlorate In water Kinetics; aq. soln. of Pt complex and ligand were mixed at 25°C; UV and NMR monitoring; not isolated;

Upstream product

• 563-47-3 3-Chloro-2-methylpropene 
• 3934-16-5 2-methyl-prop-2-ene-1-sulfonic acid 
• 762-84-5 N-tert-butylacetamide 
• 115-11-7 isobutene 
• 1118-32-7 N-tert-butylpropionamide 

Downstream Products

• 14568-34-4 2-methylprop-2-ene-1-sulfonyl chloride 
• 3934-16-5 2-methyl-prop-2-ene-1-sulfonic acid 
• 110-16-7 maleic acid 
• 115-11-7 isobutene 
• 631-28-7 1,2,3-tribromo-2-methylpropane 

Relevant articles and documents

Olefination with Sulfonyl Halides and Esters: E-Selective Synthesis of Alkenes from Semistabilized Carbanion Precursors

Carbanions of sulfonyl halides and activated sulfonates add to carbonyl compounds, and so-formed aldol-type adducts spontaneously fragment into olefins. This transformation mimics the one-pot Julia olefination with (hetero)aryl sulfones, but the mechanism of fragmentation involves a four-membered intermediate, typical for reactivity of phosphorus reagents. Moreover, in contrast to the reactions of sulfones, sulfonates of fluorinated alcohols (TFE and HFI) produce byproducts that are easily removed during workup. In our report, we focus on reactions of unstabilized and semistabilized carbanion precursors: alkylsulfonates, and allyl- and benzylsulfonates, respectively. In particular for semistabilized systems, olefins were synthesized as predominant E isomers in good yields. The presented studies reveal that optimal reaction conditions, including the type of base and alcohol groups of the sulfonates, are different depending on stabilization of the carbanion precursors and structure of the carbonyl substrates. The practical synthetic guide is supplemented with a discussion of the mechanism, based on reactivity studies of intermediates and identification of side-products.

Process for the preparation of methallyl sulfonic acid and its salts

A process for the preparation of methallyl sulfonic acid and its salt which process comprises the reaction of isobutylene with a complex of sulfur trioxide to form methallyl sulfonic acid and, if desired, neutralization of the formed acid with an alkaline compound to obtain its salt. The sulfur trioxide complex is prepared by a reaction of sulfur trioxide with a mono-alkyl substituted amide of an aliphatic carboxylic acid, which has a tertiary carbon atom bonded directly to the nitrogen atom thereof.