Drazoxolon

Base Information

• Chemical Name: Drazoxolon
• CAS No.: 5707-69-7
• Molecular Formula: C10H8 Cl N3 O2
• Molecular Weight: 237.645
• Hs Code.: 29349990
• European Community (EC) Number: 227-197-8
• UNII: 8B76Z92B5M
• DSSTox Substance ID: DTXSID3041908,DTXSID10859925
• Nikkaji Number: J31.843D
• Wikidata: Q27155725
• Mol file: 5707-69-7.mol

Synonyms:DRAZOXOLON;5707-69-7;Drazoxolone;Ganocide;Sopracol;Saisan;Mil-col;Sopracol 781;Caswell No. 207C;Milcol;Drazoxolon [BSI:ISO];4,5-Isoxazoledione, 3-methyl-, 4-[(2-chlorophenyl)hydrazone];PP781;EINECS 227-197-8;EPA Pesticide Chemical Code 207400;3-Methyl-4-(o-chlorophenylhydrazono)-5-isoxazolone;4-(2-Chlorophenylhydrazone)-3-methyl-5-isoxazolone;4-(2-Chlorophenylhydrazono)-3-methyl-5(4H)-isoxazolone;UNII-8B76Z92B5M;3-Methyl-4,5-isoxazoledione 4-((2-chlorophenyl)hydrazone);3-Methyl-4-((o-chlorophenyl)hydrazone)-4,5-isoxazoledione;8B76Z92B5M;4-((o-Chlorophenyl)hydrazono)-3-methyl-2-isoxazolin-5-one;(Z)-4-(2-(2-chlorophenyl)hydrazono)-3-methylisoxazol-5(4H)-one;3-Methyl-2-isoxazoline-4,5-dione 4-((2-chlorophenyl)hydrazone);3-Methyl-4,5-isoxazoledione 4-((o-chlorophenyl)hydrazone);4,5-Isoxazoledione, 3-methyl-, 4-((o-chlorophenyl)hydrazone);4,5-Isoxazoledione, 3-methyl-, 4-[(o-chlorophenyl)hydrazone];Drazoxolan;4,5-Isoxazoledione, 3-methyl-, 4-((2-chlorophenyl)hydrazone);HYDRAZOLON;Mil-Col (pesticide);DRAZOXOLON [MI];DRAZOXOLON [ISO];SCHEMBL55516;SCHEMBL162884;DTXSID3041908;CHEBI:82071;DTXSID10859925;PP 781;STK329720;AKOS005439133;AKOS015902985;AKOS040744711;JF 1633;JF 2067;JF-1633;LS-86683;FT-0771219;Drazoxolon, PESTANAL(R), analytical standard;C18929;R 22395;R-22395;Q27155725;3-Methyl-4-[(2-chlorophenyl)hydrazone]-4,5-isoxazoledione;4-[(2-chlorophenyl)diazenyl]-3-methyl-2H-1,2-oxazol-5-one;(ez)-4-(2-chlorophenylhydrazono)-3-methyl-1,2-oxazol-5(4h)-one;3-Methyl-4,5-isoxazoledione 4-((o-chlorophenyl)hydrazone) (8CI);3-METHYL-4-(2-CHLOROPHENYLHYDRAZONO)-2-ISOXAZOLIN-5-ONE;4,5-ISOXAZOLEDIONE, 3-METHYL-, 4-(2-(2-CHLOROPHENYL)HYDRAZONE);4-[2-(2-chlorophenyl)diazen-1-yl]-3-methyl-2,5-dihydro-1,2-oxazol-5-one;4-[2-(2-Chlorophenyl)hydrazinylidene]-3-methyl-1,2-oxazol-5(4H)-one;(4E)-4-[2-(2-chlorophenyl)hydrazinylidene]-3-methyl-1,2-oxazol-5(4H)-one;1005512-62-8

Chemical Property of Drazoxolon

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.000292mmHg at 25°C
• Melting Point: 168℃
• Refractive Index: 1.5790 (estimate)
• Boiling Point: 321.8°Cat760mmHg
• PKA: 9.13±0.40(Predicted)
• Flash Point: 148.4°C
• PSA: 63.05000
• Density: 1.45g/cm³
• LogP: 1.54920
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 237.0305042
• Heavy Atom Count: 16
• Complexity: 354

Purity/Quality:

99.9% ^*data from raw suppliers

Drazoxolon ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Toxic by ingestion.
• Hazard Codes: T,N
• Statements: 25-50/53
• Safety Statements: 22-24-36/37-45-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)ON1)N=NC2=CC=CC=C2Cl
• Uses: Fungicide.

Technology Process of Drazoxolon

There total 5 articles about Drazoxolon 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: 85.6%

ethyl 2-(2-(2-chlorophenyl)hydrazono)-3-oxobutanoate (21836-30-6) → 4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone (5707-69-7)

Guidance literature:

With hydroxylamine hydrochloride; acetic acid; In ethanol; for 18h; Reflux; Inert atmosphere;

DOI:10.1039/c5nj02604k

Reference yield: 34.7%

α-(2-Chlor-benzolazo)-acetessigsaeure-ethylester (33165-52-5) → 4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone (5707-69-7)

Guidance literature:

With hydroxylamine hydrochloride; sodium acetate; In ethanol; water; Heating;

DOI:10.1248/cpb.32.3291

Reference yield:

o-chloroaniline (95-51-2) → 4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone (5707-69-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) HCl, NaNO₂; 2.) NaOAc / 1.) H₂O, 0 deg C; 2.) EtOH, H₂O

2: 34.7 percent / NH₂OH*HCl, NaOAc / ethanol; H₂O / Heating

With hydrogenchloride; hydroxylamine hydrochloride; sodium acetate; sodium nitrite; In ethanol; water;

DOI:10.1248/cpb.32.3291

upstream raw materials:

α-(2-Chlor-benzolazo)-acetessigsaeure-ethylester

o-chloroaniline

ethyl 2-(2-(2-chlorophenyl)hydrazono)-3-oxobutanoate

Downstream raw materials:

2-but-2-enoyl-4-(2-chloro-phenylazo)-3-methyl-2H-isoxazol-5-one

2,3-dimethyl-4-(o-chlorophenylazo)isoxazol-5-one

4-(N-methyl-o-chlorophenylhydrazono)-3-methylisoxazol-5-one

2-acetyl-4-(2-chloro-phenylazo)-3-methyl-2H-isoxazol-5-one

Refernces

• 1、 Tanaka,Matsuo,Nakanishi,Jo,Shiota,Yamaguchi,Yoshino,Kawaguchi. "Syntheses and antimicrobial activities of five-membered heterocycles having a phenylazo substituent". . p. 3291 - 3298. Retrieved 2007/10/02.
• 2、 -. "Thiolphosphoric acid-S-4-nitro-2-trichloromethylphenyl esters as fungicides". . . Retrieved 2008/06/13.