Methyl 5-chloro-1-hydrazono-2-hydroxy-2,3-dihydro-1H-indene-2-carboxylate

Base Information

• Chemical Name: Methyl 5-chloro-1-hydrazono-2-hydroxy-2,3-dihydro-1H-indene-2-carboxylate
• CAS No.: 144172-26-9
• Molecular Formula: C₁₁H₁₁ClN₂O₃
• Molecular Weight: 254.673
• Hs Code.: 2928000090
• DSSTox Substance ID: DTXSID50571790
• Mol file: 144172-26-9.mol

Synonyms:144172-26-9;Methyl 5-chloro-1-hydrazono-2-hydroxy-2,3-dihydro-1H-indene-2-carboxylate;SCHEMBL8434650;DTXSID50571790

Chemical Property of Methyl 5-chloro-1-hydrazono-2-hydroxy-2,3-dihydro-1H-indene-2-carboxylate

Chemical Property:

• Boiling Point: 376.316 °C at 760 mmHg
• PKA: 10.48±0.20(Predicted)
• Flash Point: 181.39 °C
• PSA: 84.91000
• Density: 1.504 g/cm³
• LogP: 1.16330
• Storage Temp.: 2-8°C
• Solubility.: Dichloromethane; DMSO; Ethyl Acetate; Methanol
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 254.0458199
• Heavy Atom Count: 17
• Complexity: 361

Purity/Quality:

97% ^*data from raw suppliers

Methyl5-chloro-1-hydrazono-2-hydroxy-2,3-dihydro-1H-indene-2-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1(CC2=C(C1=NN)C=CC(=C2)Cl)O
• Isomeric SMILES: COC(=O)C\1(CC2=C(/C1=N/N)C=CC(=C2)Cl)O
• Uses: (Z)-Methyl 5-Chloro-1-hydrazono-2-hydroxy-2,3-dihydro-1H-indene-2-carboxylate is an intermediate in the synthesis of IN-KG 433 (I627995) which is an impurity of Indoxacarb (I654000), an oxadiazine pesticide that acts against lepidopteran larvae and is the active ingredient in a number of household insecticides including cockroach baits.

Technology Process of Methyl 5-chloro-1-hydrazono-2-hydroxy-2,3-dihydro-1H-indene-2-carboxylate

There total 9 articles about Methyl 5-chloro-1-hydrazono-2-hydroxy-2,3-dihydro-1H-indene-2-carboxylate 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:

methyl 5-chloro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate (65738-56-9) → 5-chloro-hydrazono-2-hydroxy-2,3-dihydro-1H-indene-2-carboxylic acid methyl ester (144172-26-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Cinchonin; tert.-butylhydroperoxide / toluene / 24 h / 20 °C / Inert atmosphere

2: hydrazine hydrate; acetic acid / methanol / 3.5 h / 90 °C / Cooling with ice

With tert.-butylhydroperoxide; hydrazine hydrate; acetic acid; Cinchonin; In methanol; toluene;

Reference yield:

methyl 5-chloro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate (65738-56-9) → 5-chloro-1-hydrazono-2-hydroxy-indan-2-carboxylic acid methyl ester (144172-26-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / MCPBA / CH₂Cl₂

2: H₂NNH₂; AcOH / methanol / 65 °C

With acetic acid; 3-chloro-benzenecarboperoxoic acid; hydrazine; In methanol; dichloromethane;

DOI:10.1002/1526-4998(200102)57:2<153::AID-PS288>3.0.CO;2-O

Reference yield:

(R,S)‐5‐chloro‐1‐oxo‐2,3‐dihydro‐2‐hydroxy‐1H‐indene‐2‐carboxylic acid methyl ester (144172-24-7) → 5-chloro-hydrazono-2-hydroxy-2,3-dihydro-1H-indene-2-carboxylic acid methyl ester (144172-26-9)

Guidance literature:

With hydrazine hydrate; acetic acid; In methanol; for 4h; Reflux;

DOI:10.1016/j.bmcl.2015.08.058

upstream raw materials:

(R,S)‐5‐chloro‐1‐oxo‐2,3‐dihydro‐2‐hydroxy‐1H‐indene‐2‐carboxylic acid methyl ester

methyl 5-chloro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate

5-chloro-1-indanone

3-chlorocinnamic acid

Downstream raw materials:

(R,S)‐5‐chloro‐1‐oxo‐2,3‐dihydro‐2‐hydroxy‐1H‐indene‐2‐carboxylic acid methyl ester

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