13894-21-8 Usage
Description
ETHYNYL P-TOLYL SULFONE, also known as Tosylacetylene, is an organic compound with the chemical formula C8H6O2S. It is characterized by its ethynyl group attached to a p-tolyl sulfone moiety, which provides unique chemical properties and reactivity. ETHYNYL P-TOLYL SULFONE is a valuable synthetic intermediate in organic chemistry due to its versatile reactivity and the ability to form a wide range of derivatives.
Uses
Used in Chemical Synthesis:
ETHYNYL P-TOLYL SULFONE is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure allows for a range of reactions, making it a valuable building block in the synthesis of complex molecules.
Used in Pharmaceutical Industry:
ETHYNYL P-TOLYL SULFONE is used as a starting reagent for the synthesis of optically active indan-2-ols. These indan-2-ols are important in the development of pharmaceutical compounds, as they can exhibit biological activities and serve as key components in the design of new drugs.
Used in Organic Chemistry Research:
In the field of organic chemistry, ETHYNYL P-TOLYL SULFONE is used as a starting reagent for the synthesis of 2-(4-methylphenylsulfonyl)ethenyl (tosvinyl, Tsv) protected derivatives. These derivatives are essential for the development of new synthetic routes and the exploration of novel chemical reactions.
Overall, ETHYNYL P-TOLYL SULFONE is a versatile and valuable compound in the fields of chemical synthesis, pharmaceutical research, and organic chemistry, with applications ranging from the development of new drugs to the exploration of novel synthetic pathways.
Synthesis Reference(s)
The Journal of Organic Chemistry, 57, p. 697, 1992 DOI: 10.1021/jo00028a053
Purification Methods
Recrystallise the sulfone from pet ether, *C6H6 or EtOH (m 66o), and dry it in a vacuum. [Beilstein 6 III 1397, 6 IV 2160.]
Check Digit Verification of cas no
The CAS Registry Mumber 13894-21-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,8,9 and 4 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 13894-21:
(7*1)+(6*3)+(5*8)+(4*9)+(3*4)+(2*2)+(1*1)=118
118 % 10 = 8
So 13894-21-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H8O2S/c1-3-12(10,11)9-6-4-8(2)5-7-9/h1,4-7H,2H3
13894-21-8Relevant articles and documents
A New Synthesis of Alkynyl Sulfones and Single Crystal X-ray Structure of p-(Tolylsulfonyl)ethyne
Tykwinski, Rik R.,Williamson, Bobby L.,Fischer, David R.,Stang, Peter J.,Arif, Atta M.
, p. 5235 - 5237 (1993)
The reaction of mono- or bis(alkynyliodonium) triflate salts with sodium p-toluenesulfinate under mild conditions affords alkynyl sulfones in 60-95percent yields.
Large π-Conjugated Metal-Organic Frameworks for Infrared-Light-Driven CO2Reduction
Li, Qian-Ru,Wang, Xiao-Shuang,Xie, Bo-Ru,Zeng, Jin-Yue,Zhang, Xian-Zheng
supporting information, p. 1218 - 1231 (2022/02/05)
It remains challenging to excite traditional photocatalysts through near-infrared (NIR) light. Attempts to use NIR-light-response materials for photochemical reduction usually suffer from inapposite band position due to extremely narrow band gaps. Here, w
Metal-free synthesis of activated ynesulfonamides and tertiary enesulfonamides
Andna, Lucile,Miesch, Laurence
supporting information, p. 5688 - 5692 (2019/06/19)
An operationally simple synthesis of activated ynesulfonamides and enesulfonamides is described. Ynesulfonamides can be obtained through reaction of sulfonylamides with activated bromoalkynes and Triton B in a short time at room temperature. Likewise, terminal alkynes react with sulfonylamides to provide enesulfonamides. Z/E enesulfonamides can be transformed exclusively into E enesulfonamides.
Gold-Catalyzed Dehydrazinative C(sp)–S Coupling Reactions of Arylsulfonyl Hydrazides with Ethynylbenziodoxolones for Accessing Alkynyl Sulfones
Shinde, Popat S.,Patil, Nitin T.
, p. 3512 - 3515 (2017/07/04)
A gold(III)-catalyzed dehydrazinative coupling reaction between arylsulfonyl hydrazides and ethynylbenziodoxolone reagents was realized for the synthesis of alkynyl sulfones. The scope and versatility of the reaction were demonstrated by the efficient synthesis of 23 derivatives with diverse structural features.
