79791-38-1 Usage
Uses
1. Used in Pharmaceutical Industry:
Dodecylbenzenesulfonyl azide is used as a reactant or reagent for the synthesis of positron emission tomography (PET) ligands, specifically for imaging metabotropic glutamate receptor type 1. This application aids in the detection and monitoring of neurological disorders.
2. Used in Organic Synthesis:
Dodecylbenzenesulfonyl azide serves as a stitching agent for the introduction of aziridines into functionalized organic molecules. This process is crucial in the development of complex organic compounds and materials.
3. Used in Antibiotic Production:
In the pharmaceutical industry, dodecylbenzenesulfonyl azide is utilized as a parenteral cephalosporin, which is a type of antibiotic. It plays a vital role in the treatment of bacterial infections.
4. Used in Chemical Research:
Dodecylbenzenesulfonyl azide is employed as a reagent for intermolecular metal-catalyzed carbenoid cyclopropanations. This reaction is essential in the synthesis of various organic compounds, including pharmaceuticals and agrochemicals.
5. Used in Solid-phase Synthesis:
In the field of chemical research, dodecylbenzenesulfonyl azide is used in the solid-phase synthesis of indolecarboxylates using palladium-catalyzed reactions. This method is significant for the production of indole-based compounds, which have applications in pharmaceuticals, agrochemicals, and materials science.
6. Used in Rhodium Carbenoid N-H Insertion Reactions:
Dodecylbenzenesulfonyl azide is also used as a reagent in solid-phase rhodium carbenoid N-H insertion reactions. This reaction is crucial for the synthesis of various nitrogen-containing organic compounds, which are valuable in the development of new drugs and other chemical products.
7. Used as a Diazo-transfer Reagent:
Dodecylbenzenesulfonyl azide is utilized as a diazo-transfer reagent for activated methylene groups. This application is essential in the synthesis of various organic compounds, particularly those with complex structures.
Preparation
prepared by addition of granular sodium azide (1.3 equiv) to a mixture of isomeric sulfonyl chlorides (from a commercial mixture of isomers of p-dodecylbenzenesulfonic acid) in acetone solution.
Reactions
Reagent for Diazo-function Transfer.
The title reagent has been called a safer diazo-transfer reagent, and is a mixture of 12 or more isomeric p-dodecylbenzenesulfonyl azides, ranging by HPLC from 24% to 1% in area and giving essentially a single spot by TLC.
The title reagent has been shown to be very useful for the synthesis of various crystalline diazocarbonyl compounds such as diazobarbituric and diazoisopropylidenemalonic acids, derivatives and homologs of diazoacetoacetic acid, and 9-diazoanthrone (eq 1).
Formation of noncrystalline byproduct dodecylsulfonamides facilitates the workup procedure and isolation of the target crys- talline diazo compounds from the reaction mixture.
storage
Dodecylbenzenesulfonyl azide is the safest of the usual are nesulfonyl azides (tosyl azide, etc.) employed in diazo-transfer processes;appropriate care should be taken,as with all azides. Use in a fume hood.
Purification Methods
elution through short column containing silica gel G with methylene chloride-hexane (1:4) as eluant.
Check Digit Verification of cas no
The CAS Registry Mumber 79791-38-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,9,7,9 and 1 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 79791-38:
(7*7)+(6*9)+(5*7)+(4*9)+(3*1)+(2*3)+(1*8)=191
191 % 10 = 1
So 79791-38-1 is a valid CAS Registry Number.
InChI:InChI=1/C18H29N3O2S/c1-2-3-4-5-6-7-8-9-10-11-14-17-15-12-13-16-18(17)24(22,23)21-20-19/h12-13,15-16H,2-11,14H2,1H3
79791-38-1Relevant articles and documents
Microchannel synthesis method of aryl sulfonyl azide
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Paragraph 0031-0032, (2019/07/04)
The invention discloses a microchannel synthesis method of aryl sulfonyl azide. Sodium azide and water are uniformly stirred and prepared into a material A, aryl sulfonyl chloride and acetone are uniformly stirred and prepared into a material B, and the material A and the material B are continuously fed into a microchannel reactor at the flow rate of 6mL/min-70mL/min and efficiently react to prepare the aryl sulfonyl azide. Compared with the prior art, the microchannel synthesis method has the advantages that process route operation is safe, conversion rate is high, cost is saved, and the yield of the aryl sulfonyl azide is higher than 80%.
Iridium-catalyzed intermolecular amidation of sp3 C-H bonds: Late-stage functionalization of an unactivated methyl group
Kang, Taek,Kim, Youngchan,Lee, Donggun,Wang, Zhen,Chang, Sukbok
supporting information, p. 4141 - 4144 (2014/04/03)
Reported herein is the iridium-catalyzed direct amidation of unactivated sp3 C-H bonds. With sulfonyl and acyl azides as the amino source, the amidation occurs efficiently under mild conditions over a wide range of unactivated methyl groups with high functional group tolerance. This procedure can be successfully applied for the direct introduction of an amino group into complex compounds and thus can serve as a powerful synthetic tool for late-stage C-H functionalization.
2-thiosubstituted carbapenems
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, (2008/06/13)
Carbapenem antibiotic compounds of the general formula: STR1 wherein the moiety STR2 is a 4, 5 or 6 membered mono, di- or tri- substituted oxygen or sulfur containing ring; wherein Z is oxygen, sulfur, sulfoxide and sulfone, pharmaceutical compositions thereof useful for the treatment of bacterial infections, processes for preparing the compounds and new intermediates useful in the process.
