GLYOXYLYL CHLORIDE P-TOLUENESULFONYLHYDRAZONE

Base Information

• Chemical Name: GLYOXYLYL CHLORIDE P-TOLUENESULFONYLHYDRAZONE
• CAS No.: 14661-69-9
• Molecular Formula: C9H11ClN2O2S
• Molecular Weight: 260.701
• Hs Code.: 2928000090
• Mol file: 14661-69-9.mol

Synonyms:GLYOXYLYL CHLORIDE P-TOLUENESULFONYLHYDRAZONE;Benzenesulfonic acid, 4-Methyl-, (2-chloro-2-oxoethylidene)hydrazide;[(p-Toluenesulfonyl)hydrazono]acetyl chloride;Glyoxylic acid chloride tosylhydrazone;(E)-2-(2-Tosylhydrazono)acetyl chloride;Benzenesulfonic acid, 4-methyl-, 2-(2-chloro-2-oxoethylidene)hydrazide

Chemical Property of GLYOXYLYL CHLORIDE P-TOLUENESULFONYLHYDRAZONE

Chemical Property:

• Melting Point: 151-153℃
• Boiling Point: 405.0±38.0 °C(Predicted)
• PKA: 7.30±0.40(Predicted)
• PSA: 83.98000
• Density: 1.41±0.1 g/cm3(Predicted)
• LogP: 2.49620
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

(E)-2-(2-Tosylhydrazono)acetylchloride 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of GLYOXYLYL CHLORIDE P-TOLUENESULFONYLHYDRAZONE

There total 6 articles about GLYOXYLYL CHLORIDE P-TOLUENESULFONYLHYDRAZONE 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: 83.0%

(E)-2-(2-benzenesulfonylhydrazide)acetic acid → (E)-2-(2-benzenesulfonylhydrazide)acetic acid chloride (14661-69-9)

Guidance literature:

With thionyl chloride; In toluene; for 2h; Inert atmosphere; Reflux;

DOI:10.1002/chem.202002675

Reference yield: 70.0%

2‐[(4‐methylbenzenesulfonamido)imino]acetic acid (14661-68-8) → p-toluenesulfonylhydrazone glyoxylic acid chloride (14661-69-9)

Guidance literature:

With thionyl chloride; In benzene; at 90 ℃; for 2h; Inert atmosphere;

DOI:10.1002/anie.201809511

Reference yield:

toluene-4-sulfonic acid hydrazide (1576-35-8) → p-toluenesulfonylhydrazone glyoxylic acid chloride (14661-69-9)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 20 °C

2: thionyl chloride / benzene; CH₂Cl₂ / 1.5 h / Heating

With thionyl chloride; In tetrahydrofuran; dichloromethane; benzene; 1: Condensation / 2: Chlorination;

DOI:10.1021/jo000029l

upstream raw materials:

2‐[(4‐methylbenzenesulfonamido)imino]acetic acid

toluene-4-sulfonic acid hydrazide

Downstream raw materials:

2-Oxo-2-phenylpropyl diazoacetate

hexyl p-toluenesulfinate

Diazo-acetic acid (2R,3R,3aS,9aR)-6-oxo-2-trityloxymethyl-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-3-yl ester

ethyl 2-diazo-3-(p-tolylsulfonyl)-pentanoate

Refernces

• 1、 Hari, Durga Prasad,Pisella, Guillaume,Wodrich, Matthew D.,Tsymbal, Artem V.,Tirani, Farzaneh Fadaei,Scopelliti, Rosario,Waser, Jerome. "Low-Temperature Intramolecular [4+2] Cycloaddition of Allenes with Arenes for the Synthesis of Diene Ligands". supporting information. p. 5475 - 5481. Retrieved 2021/01/21.
• 2、 Arter, Christopher,Chow, Shiao,Green, Adam I.,Karageorgis, George,Leggott, Abbie,Liver, Samuel,Nelson, Adam,Trask, Luke,Warriner, Stuart. "Efficient Approaches for the Synthesis of Diverse α-Diazo Amides". . p. 1695 - 1706. Retrieved 2020/05/25.