5-Chloro-1-oxo-2,3-dihydro-2-hydroxy-1H-indene-2-carboxylic acid methyl ester

Base Information

• Chemical Name: 5-Chloro-1-oxo-2,3-dihydro-2-hydroxy-1H-indene-2-carboxylic acid methyl ester
• CAS No.: 144172-26-9
• Molecular Formula: C₁₁H₁₁ClN₂O₃
• Molecular Weight: 254.673
• Hs Code.: 2928000090
• Mol file: 144172-26-9.mol

Synonyms:1H-Indene-2-carboxylicacid, 5-chloro-1-hydrazono-2,3-dihydro-2-hydroxy-, methyl ester (9CI);

Chemical Property of 5-Chloro-1-oxo-2,3-dihydro-2-hydroxy-1H-indene-2-carboxylic acid methyl ester

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

Purity/Quality:

98%Min ^*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:

• 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 5-Chloro-1-oxo-2,3-dihydro-2-hydroxy-1H-indene-2-carboxylic acid methyl ester

There total 9 articles about 5-Chloro-1-oxo-2,3-dihydro-2-hydroxy-1H-indene-2-carboxylic acid methyl ester 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

Refernces

• 1、 Zhang, Jianqiang,Hao, Wenbo,Zhorov, Boris S.,Dong, Ke,Jiang, Dingxin. "Discovery of a Novel Series of Tricyclic Oxadiazine 4a-Methyl Esters Based on Indoxacarb as Potential Sodium Channel Blocker/Modulator Insecticides". . p. 7793 - 7809. Retrieved 2019/08/01.
• 2、 -. "Oxadiazine derivative, and preparation method and application thereof". Paragraph 0098. . Retrieved 2018/04/01.