4545-18-0

Basic information

• Product Name: Cyclohexanone Tosylhydrazone
• Synonyms: Cyclohexanone p-Toluenesulfonylhydrazone;Cyclohexanone Tosylhydrazone;N'-Cyclohexylidene-4-methylbenzenesulfonic acid hydrazide;Cyclohexanone tolysulfonylhydrazone;Cyclohexylidene p-toluenesulfonylhydrazone;NSC 126942;NSC 132020;NSC 132029
• CAS NO: 4545-18-0
• Molecular Formula: C₁₃H₁₈N₂O₂S
• Molecular Weight: 266.3592
• Mol File: 4545-18-0.mol
• Article Data: 34

Chemical Properties

• Melting Point: 161-162℃
• Boiling Point: 415.4°Cat760mmHg
• Flash Point: 205°C
• Appearance: /
• Density: 1.24g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 10.48±0.20(Predicted)
• CAS DataBase Reference: Cyclohexanone Tosylhydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanone Tosylhydrazone(4545-18-0)
• EPA Substance Registry System: Cyclohexanone Tosylhydrazone(4545-18-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-37-60
• TSCA: No
• Hazardous Substances Data: 4545-18-0(Hazardous Substances Data)

Usage

General Description

Cyclohexanone tosylhydrazone is a chemical compound that is commonly used in organic synthesis as a reagent for the preparation of hydrazones. It is derived from cyclohexanone and p-toluenesulfonyl hydrazide, and is often employed as a masking agent for carbonyl groups. Cyclohexanone Tosylhydrazone has been utilized in various reactions such as the reduction of carbonyl compounds to the corresponding alcohols, and in the synthesis of heterocyclic compounds. Additionally, cyclohexanone tosylhydrazone has been investigated for its potential biological activities, including its ability to inhibit the growth of certain bacteria and fungi, making it a versatile and widely studied compound in the field of organic chemistry.

Upstream product

• 108-94-1 cyclohexanone 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 85814-68-2 C₁₃H₁₇N₃O₄S 
• 177-12-8 1,2,4-Trioxaspiro<4.5>decan 
• 98-59-9 p-toluenesulfonyl chloride 
• 4883-67-4 2-nitrocyclohexanone 

Downstream Products

• 64884-88-4 (1R*,1'RS*)-1-cyclohex-2-enyl-propan-1-ol 
• 1192-88-7 1-cyclohexene-1-carboxaldehyde 
• 20758-60-5 1-(4-methoxyphenyl)cyclohexene 
• 1361974-18-6 2-cyclohexyl-5-(4-methoxyphenyl)oxazole 
• 104462-82-0 2-cyclohexylbenzoxazole 
• 40115-03-5 2-cyclohexyl-benzothiazole 
• 404584-29-8 2-cyclohexyl-5-methyl-1,3-benzoxazole 
• 18860-06-5 2-cyclohexyl-5-phenyloxazole 
• 1329506-06-0 2-cyclohexyl-5-phenylbenzoxazole 
• 1361974-24-4 (E)-2-cyclohexyl-5-styryloxazole 
• 1361974-22-2 4-(2-cyclohexyloxazol-5-yl)-N,N-diethylbenzamide 
• 1361974-16-4 4-{5-(2-cyclohexyl)oxazolyl}benzonitrile 
• 1361974-14-2 2-cyclohexyl-5-{4-(trifluoromethyl)phenyl}oxazole 
• 1361974-20-0 2-cyclohexyl-5-(1-naphthyl)oxazole 

Relevant articles and documents

Copper-catalyzed tri- or tetrafunctionalization of alkenylboronic acids to prepare tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles

We describe a cascade strategy for tri- or tetrafunctionalization of alkenylboronic acids to prepare diverse tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles in good yields withN-hydroxybenzotriazin-4-one (HOOBT) and arylhydrazines as oxygen and nitrogen sources, respectively. Mechanistic studies reveal that the domino reaction undergoes the copper-catalyzed Chan-Lam reaction, [2,3]-rearrangement, nucleophilic substitution, oxidation and sequential [3,3]-rearrangement over five steps in a one-pot reaction. The reaction shows a broad substrate scope and tolerates a wide range of functional groups. More importantly, the reaction is easily performed at gram scales and the product is purified by simple extraction, washing, and recrystallization without flash column chromatography. The present protocol features easily available starting materials, high site-marked functionalization, five-step cascade in one pot, multiple C-C/C-O/C-N bond formation, and diversity of indole motifs.

Pd-Catalyzed Heck-Type Reaction: Synthesizing Highly Diastereoselective and Multiple Aryl-Substituted P-Ligands

In this work, an efficient palladium-catalyzed Heck-type reaction was successfully used to synthesize a wide range of monoaryl-or diaryl-substituted P-ligands with excellent yields and diastereoselectivity (up to 98% yield, dr >20:1). The preliminary mechanistic studies demonstrated that it possibly underwent a cationic Heck reaction that was assisted by silver salt, and it revealed the significant role of P(O)Ar2 for excellent yields and diastereoselectivity.

Copper-catalyzed one-pot coupling reactions of aldehydes (ketones), tosylhydrazide and 2-amino(benzo)thiazoles: An efficient strategy for the synthesis of N-alkylated (benzo)thiazoles

An efficient and practical C–N bond formation methodology for the synthesis of N-alkylated (benzo)thiazoles was developed, via the copper-catalyzed one-pot two-step reactions of 2-amino(benzo)thiazoles and aldehydes (ketones) with tosylhydrazide. This cross-coupling reaction proceeded smoothly and tolerated a broad range of functional groups (46 examples). A variety of functionalized N-alkylated (benzo)thiazoles were obtained in moderate to high yields. Notably, gram-scale synthesis of fanetizole (anti-inflammatory drug) was also realized through this protocol.