Acetophenone tosylhydrazone

Base Information

• Chemical Name: Acetophenone tosylhydrazone
• CAS No.: 4545-21-5
• Molecular Formula: C15H16N2O2S
• Molecular Weight: 288.37
• Hs Code.: 2935009090
• NSC Number: 126912
• Mol file: 4545-21-5.mol

Synonyms:Acetophenone tosylhydrazone;4545-21-5;4-methyl-n'-(1-phenylethylidene)benzenesulfonohydrazide;Acetophenone p-Toluenesulfonylhydrazone;MLS002919908;NSC126912;(Z)-4-methyl-N'-(1-phenylethylidene)benzenesulfonohydrazide;SCHEMBL715107;SCHEMBL715108;Acetophenone tosylhydrazone, 97%;MFCD01140191;AKOS003238781;NSC-126912;A826804;4-methyl-n'-[(1e)-1-phenylethylidene]benzenesulfonohydrazide

Chemical Property of Acetophenone tosylhydrazone

Chemical Property:

• Melting Point: 144-149oC(lit.)
• Boiling Point: 437.1°Cat760mmHg
• PKA: 9.81±0.40(Predicted)
• Flash Point: 218.1°C
• PSA: 66.91000
• Density: 1.17g/cm³
• LogP: 4.16920
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 288.09324893
• Heavy Atom Count: 20
• Complexity: 425

Purity/Quality:

97% ^*data from raw suppliers

Acetophenone tosylhydrazone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NN=C(C)C2=CC=CC=C2
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)N/N=C(\C)/C2=CC=CC=C2
• General Description: Acetophenone tosylhydrazone, also known as acetophenone p-toluenesulfonylhydrazone or acetophenone N-tosylhydrazone, is a derivative of acetophenone where the carbonyl group is converted into a tosylhydrazone functional group. It serves as a precursor for generating diazo compounds, which are valuable intermediates in the synthesis of metal complexes, such as aluminum compounds, and can be applied in catalytic reactions like hydroboration. ACETOPHENONE TOSYLHYDRAZONE is part of a broader class of N-tosyl hydrazones used in organic and organometallic synthesis to facilitate the formation of reactive intermediates for constructing complex molecular structures.

Technology Process of Acetophenone tosylhydrazone

There total 9 articles about Acetophenone tosylhydrazone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

acetophenone (98-86-2) + toluene-4-sulfonic acid hydrazide (1576-35-8) → acetophenone p-toluenesulfonylhydrazone (4545-21-5)

Guidance literature:

In 1,4-dioxane; at 50 ℃; for 0.166667h; Temperature; Concentration; Flow reactor;

DOI:10.1039/c6ra19022g

Reference yield: 90.0%

1-azidostyrene (16717-64-9) + toluene-4-sulfonic acid hydrazide (1576-35-8) → acetophenone p-toluenesulfonylhydrazone (4545-21-5)

Guidance literature:

In water; at 60 ℃; Temperature; Solvent;

Reference yield: 52.0%

C10H13N3 (76291-23-1) + p-toluenesulfonyl chloride (98-59-9) → acetophenone p-toluenesulfonylhydrazone (4545-21-5) + N3-(1-phenylethylidene)-N1-methyl-N1-p-toluenesulfonylformamide hydrazone (76291-26-4)

Guidance literature:

With triethylamine; In toluene; for 72h;

DOI:10.3891/acta.chem.scand.34b-0233

upstream raw materials:

acetophenone

toluene-4-sulfonic acid hydrazide

C₁₀H₁₃N₃

p-toluenesulfonyl chloride

Downstream raw materials:

(1-diazoethyl)benzene

3-phenyl-2-oxabutane

(2-methylcyclopropane-1,1,2-triyl)tribenzene

1-ethoxy-1-phenylethane

Refernces

N-Tosyl Hydrazone Precursor for Diazo Compounds as Intermediates in the Synthesis of Aluminum Complexes

10.1021/acs.organomet.8b00518

The research explores the synthesis of aluminum compounds using N-tosyl hydrazones as precursors for diazo compounds. The study involves a one-pot reaction of LAlH2 with various N-tosyl hydrazones, resulting in the formation of aluminum complexes with unique structures. The chemicals that played a crucial role in this research include LAlH2 (β-diketiminato aluminum dihydride), N-tosyl hydrazones (such as 4-methyl-N′-(1-phenylethylidene)benzenesulfonohydrazide, N′-(thiophen-2-ylmethylene)benzenesulfonohydrazide, and N′-(2-fluorobenzylidene)-4-methylbenzenesulfonohydrazide), and NaH (sodium hydride). These compounds were used to generate diazo intermediates, which then reacted with LAlH2 to form the desired aluminum complexes. The study also investigates the catalytic activity of these aluminum compounds in the hydroboration of benzaldehyde, yielding high conversion rates. The research provides a novel method for the synthesis of aluminum compounds with potential applications in catalysis and organic synthesis.