7385-85-5

Basic information

• Product Name: 2-Naphthyl p-Toluenesulfonate
• Synonyms: 2-Naphthyl p-Toluenesulfonate;p-Toluenesulfonic Acid 2-Naphthyl Ester;2-Naphthyl p-Toluenesulfonate
• CAS NO: 7385-85-5
• Molecular Formula: C₁₇H₁₄O₃S
• Molecular Weight: 298.35626
• Mol File: 7385-85-5.mol
• Article Data: 40

Chemical Properties

• Melting Point: 123.0 to 127.0 °C
• Boiling Point: 476.7°C at 760 mmHg
• Flash Point: 242.1°C
• Appearance: /
• Density: 1.277g/cm³
• Vapor Pressure: 8.61E-09mmHg at 25°C
• Refractive Index: 1.64
• CAS DataBase Reference: 2-Naphthyl p-Toluenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Naphthyl p-Toluenesulfonate(7385-85-5)
• EPA Substance Registry System: 2-Naphthyl p-Toluenesulfonate(7385-85-5)

Safety Data

• Hazardous Substances Data: 7385-85-5(Hazardous Substances Data)

Usage

General Description

2-Naphthyl p-Toluenesulfonate, also known as p-Toluenesulfonic acid 2-naphthyl ester or 2-Naphthyl tosylate, is a chemical compound utilized in the industrial and scientific fields. Its molecular formula is C17H14O3S, and it falls under the category of organic compounds named Benzenoid Monocarboxylic Acids and derivatives. This white crystalline solid is soluble in polar solvents such as alcohols and ethers. It is commonly used as a reactant in various organic synthesis processes due to its high reactivity towards nucleophiles. It also has applications in analytical chemistry to design photochemically active molecules and molecular sensors. It should be handled with care as it is harmful if swallowed, inhaled or comes in contact with skin.

InChI:InChI=1/C17H14O3S/c1-13-6-10-17(11-7-13)21(18,19)20-16-9-8-14-4-2-3-5-15(14)12-16/h2-12H,1H3

Upstream product

• 104-15-4 toluene-4-sulfonic acid 
• 135-19-3 β-naphthol 
• 98-59-9 p-toluenesulfonyl chloride 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 72973-25-2 N,N-dimethyl-1-(p-tolylsulfonyl)pyridin-1-ium-4-amine chloride 
• 4124-41-8 p-toluenesulfonylanhydride 
• 91-20-3 naphthalene 
• 3470-50-6 6-Hydroxy-1-tetralone 
• 1290085-97-0 5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl 4-methylbenzenesulfonate 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 93259-50-8 p-Toluolsulfonsaeure-<8-brom-naphthyl-(2)-ester> 
• 42768-98-9 1-bromo-2-naphthyl p-toluenesulfonate 
• 93260-53-8 5,8-Dibrom-2-tosyloxy-naphthalin 
• 59115-49-0 2-(p-tolyl)naphthalene 
• 33104-31-3 β-(3-methoxyphenyl)naphthalene 
• 1218993-00-0 3-(naphthalene-6-yl)benzonitrile 
• 1218993-01-1 2-(3-methyl-2-nitrophenyl)naphthalene 
• 1218993-02-2 2-(5-methoxy-2-nitrophenyl)naphthalene 
• 1218992-99-4 2-(5-methyl-2-nitrophenyl)naphthalene 
• 460743-71-9 2-(4-(trifluoro-methyl)phenyl)naphthalene 
• 2765-24-4 4'-nitro-2-phenylnaphthalene 
• 94064-82-1 2‐(3‐nitrophenyl)naphthalene 
• 93328-79-1 4-(naphthalene-6-yl)benzonitrile 
• 94064-83-2 2-(2-nitrophenyl)naphthalene 

Relevant articles and documents

A comparative study of thallium(iii) and iodine(iii)-mediated ring contraction reactions for the synthesis of indane

Reported herein is a comparative study of the synthesis of indaneviaring contraction reaction, mediated by iodine(iii) and thallium(iii). A series of protected 1,2-dihydronaphthalenes were synthesized and subjected to hydroxy(tosyloxy)iodobenzene (HTIB) and thallium(iii) nitrate trihydrate (TTN) in trimethyl orthoformate (TMOF) to compare the percent yields provided by both oxidizing agents. The yields of the ring contracted products (indanes) were in the range of 61-88% for reactions performed with TTN·3H2O in TMOF. However, the yields were found to be significantly lower (e.g., 18-34%) when using HTIB in TMOF with some addition products. This study provides an important development related to the efficacy of the two oxidizing agents for ring contraction reaction.

Palladium-Catalyzed Cyclobutanation of Aryl Sulfonates through both C-O and C-H Cleavage

A palladium-catalyzed cyclobutanation of aryl sulfonates with strained alkenes has been developed. The methodology is featured to achieve the cleavage of both C-O and C-H bonds of phenol derivatives in one pot. Under the reaction conditions, in addition t

Coupling of C(sp3)-H bonds with C(sp2)-O electrophiles: mild, general and selective

Herein is reported the mild and general coupling of amine/ether C(sp3)-H bonds with various kinds of C(sp2)-O electrophiles with high selectivity and efficiency. Valuable allylic/benzylic amines are generated in moderate to excellent yields. The utility of this transformation is demonstrated by a broad substrate scope (>50 examples), good functional group tolerance and facile product modification.