CAS 81-07-2 Saccharin - Analytical Products / Alfa Chemistry

CAT	APS81072
CAS	81-07-2
Structure
MDL Number	MFCD00005866
Synonyms	Saccharin, Benzoic sulfimide, Gluside, Saccharine, Saccharin insoluble, 1,2-Benzisothiazolin-3-one, 1,1-dioxide (8CI), o-Benzoyl sulfimide, Saccharin, 3-Benzisothiazolinone 1,1-dioxide, 2,3-Dihydro-1,2-benzisothiazol-3-one-1,1-dioxide, Saccharin acid, Saccharimide, o-Benzoic sulfimide, NSC 5349, Saccharol, o-Sulfobenzimide, Benzosulfinide, 1,1-Dioxo-1,2-benzisothiazol-3(2H)-one, Saccharinol, Anhydro-o-sulfaminebenzoic acid, Benzosulfimide, 550 Saccharine, o-Benzosulfimide, o-Sulfobenzoic acid imide, 1,1-Dioxo-1,2-benzothiazol-3-one, Garantose, 2,3-Dihydro-3-oxobenzisosulfonazole, 1,2-Benzisothiazol-3(2H)-one 1,1-dioxide, 1,1-Dioxido-3-oxo-2,3-dihydrobenzo[d]isothiazole, 1,2-Dihydro-2-ketobenzisosulfonazole, Necta Sweet, Glucid, o-Benzoic acid sulfimide, Benzoic sulphinide, Saccharinose, 3-Hydroxybenzisothiazole-S,S-dioxide
IUPAC Name	1,1-dioxo-1,2-benzothiazol-3-one
Molecular Weight	183.18
Molecular Formula	C7H5NO3S
Canonical SMILES	O=C1NS(=O)(=O)c2ccccc12
InChI	InChI=1S/C7H5NO3S/c9-7-5-3-1-2-4-6(5)12(10,11)8-7/h1-4H,(H,8,9)
InChI Key	CVHZOJJKTDOEJC-UHFFFAOYSA-N
REAXYS Number	6888

Description	United States Pharmacopeia (USP) Reference Standard
Accurate Mass	182.999
Form	neat
Format	Neat
MP	226-229 °C (lit.)
Size	200MG

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CAT	Size	Shipping	Storage Conditions	Description	Price
APS81072-250MG	250MG	Room Temperature	+20°C	Subcategory: EU Methods, Food additives, flavours and adulterants	Inquiry
APS81072-30MG	30MG	Room Temperature	2-8°C Fridge/Coldroom	Subcategory: European Pharmacopoeia (Ph. Eur.); API Family: Matrix - API Family See respective official monograph(s); Product Type: Excipient	Inquiry
APS81072-500MG	500MG	Room Temperature	+18°C	Subcategory: National Measurement Laboratory (NML) at LGC, Multi-element, Food additives, flavours and adulterants	Inquiry

Case Study

Saccharin Used for the Evaluation of Advanced Oxidation Processes in Contaminant Degradation Applications

Ye, Cheng, et al. Chemosphere 288 (2022): 132337.

Saccharin (SAC), a widely used artificial sweetener, has been increasingly detected in aquatic environments, raising environmental and health concerns due to its persistence and potential toxicity. In this study, SAC was employed as a model contaminant to evaluate the efficiency and mechanism of advanced oxidation processes (AOPs), specifically UV-activated hydrogen peroxide (UV/H₂O₂) and persulfate (UV/PS) systems.
Degradation experiments were conducted in a UV-irradiated glass reactor using a low-pressure mercury lamp (254 nm). A 0.11 mM SAC solution, buffered with 0.2 M phosphate, was treated with either H₂O₂ or persulfate under constant stirring at 20 ± 0.5 °C. Results showed that the UV/H₂O₂ process achieved complete degradation of 20 mg/L SAC within 45 minutes, outperforming the UV/PS system.
Quenching and radical probe experiments revealed that hydroxyl radicals (·OH) generated in the UV/H₂O₂ process exhibited higher reactivity toward SAC (1.37-1.56 × 10⁹ M⁻¹ s⁻¹) compared to sulfate radicals (SO₄·⁻) from UV/PS (3.84-4.13 × 10⁸ M⁻¹ s⁻¹). This mechanistic insight underscores the superiority of ·OH in degrading aromatic sulfonamide structures like saccharin.
These findings establish saccharin as a reliable probe for evaluating radical-driven AOPs and support the application of UV/H₂O₂ as an effective strategy for removing persistent organic micropollutants from water matrices.

Saccharin Used for the Initiation of Peroxide-Free Radical Polymerization of Acrylates

Takahashi, Issei, and Xavier Allonas. European Polymer Journal 188 (2023): 111900.

Saccharin (SAC1) has been successfully employed as a key component in a peroxide-free redox initiating system for radical polymerization of acrylates. In this novel approach, saccharin is combined with an aromatic amine and a copper salt to trigger polymerization, eliminating the need for traditional peroxides and minimizing associated stability risks.
To prevent premature gelation of the resin, a two-component (2K) system was developed. One part contains saccharin and copper salt, while the other includes a tertiary aromatic amine. These are mixed in a 1:1 ratio immediately prior to polymerization. Several saccharin analogs were also tested, including di-toluene sulfonamide (SAC2), 3H-1,2-benzodithiol-3-one 1,1-dioxide (SAC3), and 2-sulfobenzoic anhydride (SAC4). Among these, only SAC1 and SAC2-both containing sulfonamide groups-exhibited effective radical generation and exothermic polymerization behavior.
Differential scanning calorimetry (DSC) analysis showed that the SAC1-based system achieved a peak polymerization time (tₚₑₐₖ) of 2.0 minutes with a degree of conversion (DoC) of 61.5%. This performance correlates with saccharin's favorable redox potential (-0.47 V/SCE), indicating efficient electron transfer in the copper-amino-sulfonamide system.
This peroxide-free redox system represents a safer, efficient route for acrylate polymerization, with saccharin serving as a crucial reducing agent for controlled radical initiation.

Saccharin Used for the Preparation of Functional Ionic Liquids as Recyclable Catalysts for Heterocycle Synthesis

Pouramiri, Behjat, et al. Journal of Molecular Structure 1292 (2023): 136013.

Saccharin (1,2-benzisothiazol-3(2H)-one-1,1-dioxide) has been effectively employed in the design and synthesis of a novel functional ionic liquid (IL) that serves as a recyclable and green catalyst for the synthesis of nitrogen-containing heterocycles, specifically Biginelli and Hantzsch derivatives. This strategy offers a solvent-free, room-temperature, and environmentally benign approach to multicomponent heterocyclic synthesis.
The IL was synthesized via a multistep route starting from saccharin, which was first converted to potassium saccharin using potassium hydroxide in ethanol. The resulting intermediate underwent nucleophilic substitution with 2-bromoacetic acid under melt conditions, yielding N-saccharinylacetic acid. This compound was then neutralized with triethylamine under reflux to afford triethylammonium 2-(1,1-dioxido-3-oxobenzo\[d]isothiazol-2(3H)-yl)acetate IL in 95% yield.
This saccharin-based IL demonstrated excellent catalytic activity in promoting Biginelli and Hantzsch reactions at room temperature without the need for additional solvents or harsh conditions. Furthermore, the catalyst could be easily recovered and reused, aligning with principles of green chemistry and sustainability.
This work highlights saccharin's versatility not only as a synthetic intermediate but also as a scaffold for developing advanced functional materials for catalysis in organic synthesis.