Cas no 23735-43-5 ((S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate)

(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate is a chiral sulfonate ester widely used as an intermediate in organic synthesis, particularly in the preparation of enantiomerically pure compounds. Its key advantages include high stereochemical stability, facilitating asymmetric synthesis with excellent enantioselectivity. The p-toluenesulfonate (tosylate) group serves as a versatile leaving group, enabling efficient nucleophilic substitution reactions. The dioxolane ring enhances solubility in common organic solvents, improving reaction handling. This compound is valuable in pharmaceutical and fine chemical applications, where precise chiral control is critical. Its well-defined structure and reactivity make it a reliable choice for complex synthetic routes requiring high purity and consistency.
(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate structure
23735-43-5 structure
Product Name:(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate
CAS No:23735-43-5
MF:C13H18O5S
MW:286.344023227692
MDL:MFCD00063234
CID:52372
PubChem ID:87568972
Update Time:2025-10-31

(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate Chemical and Physical Properties

Names and Identifiers

    • (S)-(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate
    • (s)-(+)-2,2-Dimethyl-1,3-dioxolane-4-ylmethyl p-toluenesulfonate
    • (S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate
    • L-(+)-1,2-Isopropylideneglycerol 3-(p-Toluenesulfonate)
    • (S)-2 2-Dimethyl-1 3-Dioxolane-4-Methanol Tosylate
    • (S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate
    • (S)-(+)-2,2-Dimethyl-4-(hydroxymethyl)-1,3-dioxolane-p-toluenesulfonate
    • 2,3-Isopropylidene-sn-glycerol 1-tosylate
    • L-glycero-2,3-dihydroxy-2,3-O-isopropylidenepropyl p-toluenesulfonate
    • SRKDUHUULIWXFT-NSHDSACASA-N
    • [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate
    • (S)-(+)-2,2-Dimethyl-1,3-dioxolane-4-ylmethyl- p-toluenesulfonate
    • (S)-(+)-2,2-Dimethyl-4-(hydroxymethyl)-1,3-dioxol
    • ((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate
    • [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 4-methylbenzene-sulfonate
    • toluene-4-sulfonic acid (S)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl ester
    • [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 4-methylbenzene-1-sulfonate
    • L-alpha,beta-Isopropylideneglycerol-gamma-tosylate
    • CS-W012219
    • AKOS005257643
    • (S)-(2,2-dimethyl-1,3-dioxalan-4-yl)methyl-4-methylbenzenesulfonate
    • SCHEMBL898388
    • (4s)-2,2-dimethyl-4-toluene-4-sulfonyloxymethyl 1,3-dioxolane
    • AKOS015890122
    • MS-20174
    • (S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate, purum, >=99.0% (sum of enantiomers, GC)
    • GEO-01178
    • (S)-toluene-4-sulfonic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
    • (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl4-methylbenzenesulfonate
    • para-toluenesulfonic acid (S)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl ester
    • C74224
    • W-200245
    • para-toluenesulfonic acid (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
    • (S)-(+)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl p-toluene sulfonate
    • DTXSID90369097
    • EN300-7403268
    • D2550
    • (S)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate
    • (S)-2,2-Dimethyl-1,3-dioxolane-4-ylmethyl p-toluenesulfonate
    • toluene-4-sulfonic acid (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
    • (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-ylmethyl p-toluenesulfonate
    • MFCD00063234
    • [(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 4-methyl-benzenesulfonate
    • (S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate, 97%
    • (2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate #
    • 23735-43-5
    • XH1305
    • 2,2-Dimethyl-1,3-dioxolane-4-methanol-4-methylbenzenesulfonate; 4-Methylbenzenesulfonic Acid (S)-(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl Ester; Toluene-4-sulfonic Acid (S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl Ester; p-Toluenesulfonic Acid ((4S)-2,2-Dimethyl-1,3-dioxolan-4-yl)methyl Ester
    • STL554969
    • BBL101173
    • (S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate
    • MDL: MFCD00063234
    • Inchi: 1S/C13H18O5S/c1-10-4-6-12(7-5-10)19(14,15)17-9-11-8-16-13(2,3)18-11/h4-7,11H,8-9H2,1-3H3/t11-/m0/s1
    • InChI Key: SRKDUHUULIWXFT-NSHDSACASA-N
    • SMILES: S(C1C=CC(C)=CC=1)(=O)(=O)OC[C@@H]1COC(C)(C)O1

Computed Properties

  • Exact Mass: 286.08700
  • Monoisotopic Mass: 286.087
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 4
  • Complexity: 390
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: 1.8
  • Topological Polar Surface Area: 70.2

Experimental Properties

  • Color/Form: Not determined
  • Density: 1.208?g/mL?at 25?°C(lit.)
  • Melting Point: 29-31 oC
  • Boiling Point: 400.1°C at 760 mmHg
  • Flash Point: Degrees Fahrenheit:235.4°F
    Degrees Celsius:113°C
  • Refractive Index: n20/D 1.506(lit.)
  • PSA: 70.21000
  • LogP: 2.93260
  • Specific Rotation: 4.2 o (c=10, abs.alcohol)
  • Optical Activity: [α]26/D +7.5°, c =?2% in DMF
  • Solubility: Not determined

(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate Security Information

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(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate Production Method

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Tiancheng Chemical (Jiangsu) Co., Ltd
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(CAS:23735-43-5)(S)-2,2-二甲基-1,3-二氧環(huán)戊基-4-甲醇對甲基苯磺酸酯
Order Number:LE25499813
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Quantity:25KG,200KG,1000KG
Purity:99%
Pricing Information Last Updated:Friday, 20 June 2025 12:49
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Additional information on (S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate

Introduction to (S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate (CAS No. 23735-43-5)

(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate, with the CAS number 23735-43-5, is a compound of significant interest in the field of pharmaceutical chemistry and biotechnology. This organosulfonate derivative has garnered attention due to its unique structural properties and potential applications in drug development and synthetic chemistry. The compound belongs to the class of chiral auxiliaries and ligands, which are crucial in asymmetric synthesis, a domain where achieving enantiopure compounds is of paramount importance.

The< strong> stereochemistry of (S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate is characterized by its (S)-configuration at the chiral center, which imparts specific interactions with other molecules. This feature makes it an excellent candidate for use as a chiral catalyst or intermediate in the synthesis of complex organic molecules. The< strong>dioxolan moiety in its structure contributes to its stability and reactivity, making it a versatile building block in organic synthesis.

In recent years, there has been a growing interest in the development of< strong>green chemistry approaches that minimize waste and maximize efficiency. (S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate has been explored as a sustainable alternative in several synthetic pathways. Its ability to facilitate asymmetric reactions under mild conditions aligns well with the principles of green chemistry. Moreover, its< strong>p-toluenesulfonate group enhances its solubility in various solvents, broadening its applicability in different reaction systems.

One of the most compelling applications of (S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate is in the pharmaceutical industry. It has been utilized as a key intermediate in the synthesis of several active pharmaceutical ingredients (APIs). For instance, it has been employed in the preparation of nonsteroidal anti-inflammatory drugs (NSAIDs) and other therapeutic agents. The< strong>enantiopurity achieved through its use ensures that the final drug products exhibit optimal pharmacological activity while minimizing side effects.

The compound's< strong>biocompatibility and low toxicity have also made it attractive for use in biomedical research. Researchers have investigated its potential as a chiral selector in chromatographic techniques, which are essential for separating enantiomers with high precision. This application is particularly valuable in drug discovery and development, where the distinction between enantiomers can significantly impact their efficacy and safety profiles.

In addition to its pharmaceutical applications, (S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate has found utility in materials science. Its unique chemical properties have been leveraged in the design of novel polymers and coatings that exhibit enhanced mechanical strength and thermal stability. These materials are being explored for use in aerospace, automotive, and electronics industries where high performance is critical.

The< strong>catalytic activity of this compound has also been studied extensively. It has been shown to act as an effective ligand in transition metal-catalyzed reactions, such as cross-coupling reactions and hydrogenations. These reactions are fundamental to constructing complex molecular architectures and have wide-ranging applications in both academic research and industrial processes.

The synthesis of (S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate involves multi-step organic transformations that highlight its synthetic versatility. Recent advancements in synthetic methodologies have enabled more efficient and scalable production processes for this compound. These improvements have not only reduced costs but also minimized environmental impact by optimizing reaction conditions and reducing waste generation.

The< strong>regioselectivity exhibited by this compound during various chemical reactions makes it a valuable tool for synthetic chemists. It allows for precise control over reaction outcomes, enabling the construction of complex molecules with high fidelity. This capability is particularly important in drug development where structural modifications can significantly alter biological activity.

In conclusion, (S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate (CAS No. 23735-43-5) is a multifaceted compound with broad applications across multiple scientific disciplines. Its unique structural features and chemical properties make it an indispensable tool for researchers working on asymmetric synthesis, pharmaceutical development, materials science, and catalysis. As our understanding of its capabilities continues to grow, so too will its importance in advancing scientific knowledge and technological innovation.

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LE25499813
Purity:99%
Quantity:25KG,200KG,1000KG
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