2158-14-7 Usage
Description
4-Acetamidobenzenesulfonyl azide is an organic compound that serves as a crucial intermediate in the synthesis of various substituted amidobenzene products. It is characterized by its reactivity and versatility in chemical reactions, making it a valuable component in the development of different chemical and pharmaceutical applications.
Uses
Used in Organic Synthesis:
4-Acetamidobenzenesulfonyl azide is used as an important organic intermediate for the synthesis of substituted amidobenzene products. Its unique structure allows for the creation of a wide range of compounds with diverse applications.
Used as a Hydroazidation Catalyst:
In the field of organic chemistry, 4-Acetamidobenzenesulfonyl azide is utilized as a hydroazidation catalyst for the facile preparation of organoazides. This application highlights its role in promoting efficient and selective reactions, leading to the formation of valuable chemical products.
Used as a Diazo Transfer Agent:
4-Acetamidobenzenesulfonyl azide also functions as a diazo transfer agent, which is essential in various chemical reactions, particularly in the synthesis of complex organic molecules.
Used in the Synthesis of Monosaccharide-Derived Alcohols:
4-Acetamidobenzenesulfonyl azide is employed as a reagent in the synthesis of monosaccharide-derived alcohols, which are important building blocks in the pharmaceutical and chemical industries.
Used in Late-Stage Intermolecular C-H Olefination:
4-Acetamidobenzenesulfonyl azide is used in the late-stage intermolecular C-H olefination, a crucial reaction in the construction of complex organic molecules with high selectivity and efficiency.
Used in Intramolecular Isomuenchnone Cycloaddition Approach to Antitumor Agents:
The compound is also utilized in the intramolecular isomuenchnone cycloaddition approach, which is a key strategy in the synthesis of antitumor agents, contributing to the development of potential cancer treatments.
Used in Rhodium-Catalyzed Carbene Cyclization Cycloaddition Cascade Reaction of Vinylsulfonates:
4-Acetamidobenzenesulfonyl azide is involved in the rhodium-catalyzed carbene cyclization cycloaddition cascade reaction of vinylsulfonates, a complex chemical process that leads to the formation of novel molecular structures with potential applications in various fields.
Used in Suzuki-Miyaura Cross Coupling Reaction:
Lastly, this compound is used in the Suzuki-Miyaura cross coupling reaction, a widely employed method in organic chemistry for the formation of carbon-carbon bonds, which are essential in the synthesis of numerous biologically active molecules and advanced materials.
Check Digit Verification of cas no
The CAS Registry Mumber 2158-14-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,1,5 and 8 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 2158-14:
(6*2)+(5*1)+(4*5)+(3*8)+(2*1)+(1*4)=67
67 % 10 = 7
So 2158-14-7 is a valid CAS Registry Number.
InChI:InChI=1/C8H8N4O3S/c1-6(13)10-7-2-4-8(5-3-7)16(14,15)12-11-9/h2-5,9H,1H3/p+1
2158-14-7Relevant articles and documents
Synthesis of the Bestmann-Ohira reagent
Pietruszka, Joerg,Witt, Andreas
, p. 4266 - 4268 (2006)
The conversion of an aldehyde to a terminal alkyne by means of a one-carbon chain extension is a key reaction in organic synthesis. By using dimethyl 1-diazo-2-oxopropylphosphonate, the Bestmann-Ohira reagent, the transformation can be achieved in one pot. A reliable, convenient sequence for the preparation of the Bestmann-Ohira reagent is described. Georg Thieme Verlag Stuttgart.
One-pot synthesis of sulfonyl-1H-1,2,3-triazolyl-thiomorpholine 1,1-dioxide derivatives and evaluation of their biological activity
Sreerama, Rakesh,Narasimha Swamy,Ravinder,Vasudeva Reddy,Narsimha, Sirassu
, p. 455 - 460 (2020/12/17)
A one-pot procedure for the synthesis of novel 1,2,3-triazole derivatives (5a–5l) in good yields (63 to 77%) using different sulfonic acids and 4-(prop-2-yn-1-yl)thiomorpholine 1,1-dioxide through the in situ generated sulfonyl azides was developed. The structures of the newly synthesized compounds were confirmed by 1H NMR, 13C NMR, mass spectrometry, and elemental analysis. The newly synthesized compounds were screened for in?vitro antibacterial activity and free radical scavenging activity in terms of hydrogen donating or radical scavenging ability by the DPPH method. Among all, the compound N-(4-((4-((1,1-dioxidothiomorpholino) methyl)-1H-1,2,3-triazol-1-yl)sulfonyl)phenyl) acetamide (5l) was found to exhibit potent activity as compared to the standard drugs.
Synthesis of Allylboranes via Cu(I)-Catalyzed B-H Insertion of Vinyldiazoacetates into Phosphine-Borane Adducts
Drikermann, Denis,M??el, Robert S.,Al-Jammal, Walid K.,Vilotijevic, Ivan
supporting information, p. 1091 - 1095 (2020/02/15)
Cu(I) catalysts enable C-B bond formation via direct insertion of vinyldiazoacetates into B-H bonds of borane-phosphine Lewis adducts to form phosphine-protected allylboranes under mild conditions. The resulting allylborane-phosphine Lewis adducts can be used in the diastereoselective allylation of aldehydes directly without the need for removal of the phosphine. The allylation reaction proceeds with high diastereoselectivity and yields 5,6-disubstituted dihydropyranones after treatment with an appropriate acid.
Visible-Light-Mediated Sulfonylimination of Tertiary Amines with Sulfonylazides Involving Csp3-Csp3 Bond Cleavage
Gui, Jiao,Xie, Haisheng,Jiang, Huanfeng,Zeng, Wei
supporting information, p. 2804 - 2807 (2019/04/30)
Visible-light-induced cross-coupling of arylsulfonyl azides with tertiaryamines in the presence of Eosin Y at room temperature has been achieved. This transformation features alkyl C-C bond cleavage and provides a green approach to N-sulfonylamidines under mild conditions.
