14661-69-9

Basic information

• Product Name: GLYOXYLYL CHLORIDE P-TOLUENESULFONYLHYDRAZONE
• 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
• CAS NO: 14661-69-9
• Molecular Formula: C₉H₉ClN₂O₃S
• Molecular Weight: 246.71384
• Mol File: 14661-69-9.mol

Chemical Properties

• Melting Point: 151-153℃
• Boiling Point: 405.0±38.0 °C(Predicted)
• Appearance: /
• Density: 1.41±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 7.30±0.40(Predicted)
• CAS DataBase Reference: GLYOXYLYL CHLORIDE P-TOLUENESULFONYLHYDRAZONE(CAS DataBase Reference)
• NIST Chemistry Reference: GLYOXYLYL CHLORIDE P-TOLUENESULFONYLHYDRAZONE(14661-69-9)
• EPA Substance Registry System: GLYOXYLYL CHLORIDE P-TOLUENESULFONYLHYDRAZONE(14661-69-9)

Safety Data

• Hazardous Substances Data: 14661-69-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
GLYOXYLYL CHLORIDE P-TOLUENESULFONYLHYDRAZONE is used as a reagent for the preparation of various compounds, particularly in the formation of hydrazones. Its reactivity with carbonyl compounds makes it a key component in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, GLYOXYLYL CHLORIDE P-TOLUENESULFONYLHYDRAZONE is used as an intermediate in the synthesis of pharmaceutical compounds. Its ability to form hydrazones can be utilized to create novel drug candidates with potential therapeutic applications.
Used in Chemical Research:
GLYOXYLYL CHLORIDE P-TOLUENESULFONYLHYDRAZONE is used as a research tool in chemical laboratories to study the formation of hydrazones and their properties. This can lead to a better understanding of chemical reactions and the development of new synthetic methods.
Used in Material Science:
In material science, GLYOXYLYL CHLORIDE P-TOLUENESULFONYLHYDRAZONE may be used in the development of new materials with specific properties, such as those that can be used in sensors or other high-tech applications, by leveraging its reactivity in forming hydrazones.

Upstream product

• 14661-68-8 2‐[(4‐methylbenzenesulfonamido)imino]acetic acid 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 

Downstream Products

• 63254-50-2 L-menthyl diazoacetate 
• 82527-82-0 (2E,6E)-10,11-epoxyfarnesyl diazoacetate 
• 145576-38-1 (E)-4-phenylbut-3-en-1-yl 2-diazoacetate 
• 145576-37-0 (Z)-4-phenyl-3-butenyl diazoacetate 
• 125416-39-9 2-Oxo-2-phenylpropyl diazoacetate 
• 161139-27-1 [Benzyl-(2-diazo-acetyl)-amino]-acetic acid methyl ester 
• 161139-28-2 methyl N-(4-methoxybenzyl)-N-diazoacetylglycinate 
• 132316-71-3 trans-cinnamyl α-diazoacetate 
• 208048-45-7 trans-(1R,5'R)-1-diazoacetic acid 1-(2',2'-dimethyl-[1',3']dioxolane-4'-yl)-3-phenyl-prop-2-enyl ester 
• 208048-46-8 cis-(1R,5'R)-1-diazoacetic acid 1-(2',2'-dimethyl-[1',3']dioxolane-4'-yl)-3-phenyl-prop-2-enyl ester 
• 208048-44-6 cis-(1S,5'R)-1-diazoacetic acid 1-(2',2'-dimethyl-[1',3']dioxolane-4'-yl)-3-phenyl-prop-2-enyl ester 
• 208048-43-5 trans-(1S,5'R)-1-diazoacetic acid 1-(2',2'-dimethyl-[1',3']dioxolane-4'-yl)-3-phenyl-prop-2-enyl ester 

Relevant articles and documents

Homologation of Electron-Rich Benzyl Bromide Derivatives via Diazo C-C Bond Insertion

The ability to manipulate C-C bonds for selective chemical transformations is challenging and represents a growing area of research. Here, we report a formal insertion of diazo compounds into the "unactivated"C-C bond of benzyl bromide derivatives catalyzed by a simple Lewis acid. The homologation reaction proceeds via the intermediacy of a phenonium ion, and the products contain benzylic quaternary centers and an alkyl bromide amenable to further derivatization. Computational analysis provides critical insight into the reaction mechanism, in particular the key selectivity-determining step.

Low-Temperature Intramolecular [4+2] Cycloaddition of Allenes with Arenes for the Synthesis of Diene Ligands

The intramolecular [4+2] cycloaddition between arenes and allenes first reported by Himbert gives rapid access to rigid polycyclic scaffolds. Herein, we report a one-pot oxyalkynylation/cycloaddition reaction proceeding under mild conditions (23–90 °C) an

Efficient Approaches for the Synthesis of Diverse α-Diazo Amides

Metal-catalysed carbenoid chemistry can be exploited for the synthesis of diverse ranges of small molecules from α-diazo carbonyl compounds. In this paper, three synthetic approaches to α-diazo amides are described, and their scope and limitations are determined. On the basis of these synthetic studies, recommendations are provided to assist the selection of the most appropriate approach for specific classes of product. The availability of practical and efficient syntheses of diverse α-diazo acetamides is expected to facilitate the discovery of many different classes of bioactive small molecules.

Synthesis of 4-substituted-3-Hydroxyquinolin-2(1H)-ones with anticancer activity

Herein we show that the 3-hydroxyquinolin-2(1H)-one (3HQ) core is a suitable platform to develop new compounds with anticancer activity against MCF-7 (IC50 up to 4.82 μM) and NCI–H460 (IC50 up to 1.8 μM) cancer cell lines. The ring-expansion reaction of isatins with diazo esters catalysed by di-rhodium (II) complexes proved to be a simple and effective strategy to synthesize 4-carboxylate-3HQs (yields up to 92%). 4-Carboxamide-3HQs were more efficiently prepared using NHS-diazoacetate in yields up to 88%. This innovative methodology enabled the construction of “peptidic-like” 3HQs, with several amino acid substituents. Among this series, the L-leucine derivative induced the cell death of MCF-7 (IC50 of 15.1 μM) and NCI–H460 (IC50 of 2.7 μM) cancer cell lines without causing any appreciable cytotoxicity against the non-cancer cell model (CHOK1).

Engineering Boron Hot Spots for the Site-Selective Installation of Iminoboronates on Peptide Chains

Boronic acids (BAs) are a promising bioconjugation function to design dynamic materials as they can establish reversible covalent bonds with oxygen/nitrogen nucleophiles that respond to different pH, ROS, carbohydrates and glutathione levels. However, the dynamic nature of these bonds also limits the control over the stability and site-selectivity of the bioconjugation, which ultimately leads to heterogeneous conjugates with poor stability under physiological conditions. Here we disclose a new strategy to install BAs on peptide chains. In this study, a “boron hot spot“ based on the 3-hydroxyquinolin-2(1H)-one scaffold was developed and upon installation on a peptide N-terminal cysteine, enables the site-selective formation of iminoboronates with 2-formyl-phenyl boronic acids (Ka of 58128±2 m?1). The reaction is selective in the presence of competing lysine ?-amino groups, and the resulting iminoboronates, displayed improved stability in buffers solutions and a cleavable profile in the presence of glutathione. Once developed, the methodology was used to prepare cleavable fluorescent conjugates with a laminin fragment, which enabled the validation of the 67LR receptor as a target to deliver cargo to cancer HT29 cells.

Catalytic Asymmetric Epoxidation of Aldehydes with Two VANOL-Derived Chiral Borate Catalysts

A highly diastereo- and enantioselective method for the epoxidation of aldehydes with α-diazoacetamides has been developed with two different borate ester catalysts of VANOL. Both catalytic systems are general for aromatic, aliphatic, and acetylenic aldehydes, giving high yields and inductions for nearly all cases. One borate ester catalyst has two molecules of VANOL and the other only one VANOL. Catalysts generated from BINOL and VAPOL are ineffective catalysts. An application is shown for access to the side-chain of taxol.

Aromatic acid ester compound and preparation method and application thereof

The invention belongs to the technical field of medicine synthesis, and relates to an aromatic acid ester compound shown as the general formula I, and a preparation method thereof and an application to medicine preparation. It is shown in a biological exp

Synthesis toward the lindenane-type sesquiterpenoid monomer of Chlorahololide A

An investigation toward the synthesis of the lindenane-type sesquiterpenoid monomer of Chlorahololide A using a Yamamoto rearrangement, intramolecular cyclopropanation reaction, 1,3-dipolar cyclization, and an intramolecular Heck reaction gave the pivotal intermediate 20. This gives a practical synthetic route that could generate further natural products of the Chloranthaceae family. Starting from alcohol (2), and on the basis of Yamamoto rearrangement, intramolecular cyclopropanation reaction, 1,3-dipolar cyclization, and intramolecular Heck reaction, the Lindenane-type sesquiterpenoid fragement (20) of Chlorahololide A (1) has been synthesized in a linear sequence of 21 steps and an overall yield of 1.8%. The flexible synthetic route could generate further natural products of the Chloranthaceae family. Copyright

N-(diazoacetyl)oxazolidin-2-thiones as sulfur-donor reagents: Asymmetric synthesis of thiiranes from aldehydes

Sulfur tyranny: Thiiranes, instead of oxiranes, can be obtained in a highly stereoselective manner through the cycloaddition reaction of N-acyl oxazolidine tethered diazo thione compounds with aldehydes catalyzed by RhII. Thus, this reaction provides versatile adducts S functionalized at both the α and β position, with concomitant generation of two contiguous stereocenters. Copyright

Total synthesis of lathyranoic acid A

The first total synthesis of lathyranoic acid A (1) was accomplished stereoselectively in a linear sequence of 20 steps and an overall yield of 1.4%. This modular synthesis featured a cyclic, stereocontrolled Cu-catalyzed intramolecular cyclopropanation t