4-METHYL-1,2,4-TRIAZOLINE-3,5-DIONE

Base Information

• Chemical Name: 4-METHYL-1,2,4-TRIAZOLINE-3,5-DIONE
• CAS No.: 13274-43-6
• Molecular Formula: C3H3N3O2
• Molecular Weight: 113.076
• Mol file: 13274-43-6.mol

Synonyms:4-Methyl-1,2,4-triazoline-3,5-dione;4-Methyl-1,2,4-triazolinedione;4-Methyl-3H-1,2,4-triazole-3,5(4H)-dione;4-Methyl-4H-1,2,4-triazole-3,5-dione;N-Methyl-1,2,4-triazoline-3,5-dione;N-Methyl-1,3,4-triazoline-2,5-dione;

Chemical Property of 4-METHYL-1,2,4-TRIAZOLINE-3,5-DIONE

Chemical Property:

• Vapor Pressure: 7.04mmHg at 25°C
• Melting Point: 107-109 °C (lit.)
• Refractive Index: 1.697
• Boiling Point: 137.5 °C at 760 mmHg
• PKA: -3.61±0.20(Predicted)
• Flash Point: 36.9 °C
• PSA: 62.10000
• Density: 1.71 g/cm³
• LogP: -0.56690
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly), Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol

Purity/Quality:

98%Min ^*data from raw suppliers

N-Methyl-1,2,4-triazolinedione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-METHYL-1,2,4-TRIAZOLINE-3,5-DIONE is a dienophile used in the partial elucidation of Trichogramma putative sex pheromone at trace levels.

Technology Process of 4-METHYL-1,2,4-TRIAZOLINE-3,5-DIONE

There total 17 articles about 4-METHYL-1,2,4-TRIAZOLINE-3,5-DIONE 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: 100.0%

4-methylurazole (16312-79-1) → 4-methyl-1,2,4-triazoline-3,5-dione (13274-43-6)

Guidance literature:

With silica gel; periodic acid; sodium nitrite; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1081/SCC-100104412

Reference yield: 73.0%

ethyl 2-(methylcarbamoyl)hydrazine-1-carboxylate (13482-66-1) → 4-methyl-1,2,4-triazoline-3,5-dione (13274-43-6)

Guidance literature:

ethyl 2-(methylcarbamoyl)hydrazine-1-carboxylate; With methanol; potassium carbonate; at 65 ℃; for 2h; Inert atmosphere;

With water; at 65 ℃; for 12h;

With tert-butylhypochlorite; In ethyl acetate; Darkness; Inert atmosphere;

DOI:10.1021/acs.oprd.0c00470

Reference yield:

4-methylurazole → 4-methyl-1,2,4-triazoline-3,5-dione (13274-43-6)

Guidance literature:

With tert-butylhypochlorite; In ethyl acetate; for 0.666667h; Ambient temperature;

DOI:10.1016/0040-4039(95)01633-S

upstream raw materials:

4-methylurazole

C₂₃H₃₁N₃O₂

8,9-benzo-4-methyl-2,4,6-triazatricyclo<5.2.2.0^2.6>undeca-8,10-diene-3,5-dione

C₁₄H₁₃N₃O₂

Downstream raw materials:

2,10,11-trimethyl-7t-phenyl-7c-phenylacetyl-dihydro-5r,8c-etheno-[1,2,4]triazolo[1,2-c][1,3,4]thiadiazine-1,3-dione

2,10,11-trimethyl-7c-phenyl-7t-phenylacetyl-dihydro-5r,8c-etheno-[1,2,4]triazolo[1,2-c][1,3,4]thiadiazine-1,3-dione

2,9-diphenyl-5r,13c;6t,12t-dietheno-5ac,12ac-[1,3]dioxapropano-[1,2,4]triazolo[1,2-a][1,2,4]triazolo[1',2':1,2]pyridazino[4,5-d]pyridazine-1,3,8,10,18-pentaone

2,6,7-trimethyl-10ξ-phenyl-10ξ-thioxo-5,8-dihydro-5r,8c-epiphosphano-[1,2,4]triazolo[1,2-a]pyridazine-1,3-dione

Refernces

• 1、 Karami, Bahador,Mallakpour, Shadpour,Farahi, Mahnaz. "Silica-supported ICI as a novel heterogeneous system for the rapid oxidation of urazoles to triazolinediones". . p. 389 - 393. Retrieved 2008.
• 2、 Liang, Xifu,Bols, Mikael. "Chemoenzymatic synthesis of enantiopure 1-azafagomine". . p. 8485 - 8488. Retrieved 1999.
• 3、 Siddiqi, Zohaib R.,Ungarean, Chad N.,Bingham, Tanner W.,Sarlah, David. "Development of a Scalable and Sublimation-Free Route to MTAD". . p. 2953 - 2959. Retrieved 2020.
• 4、 Zolfigol, Mohammad Ali,Zebarjadian, Mohammad Hassan,Chehardoli, Gholamabbas,Mallakpour, Shadpour E,Shamsipur, Mojtaba. "An efficient method for the oxidation of urazoles with [NO+·crown· H(NO3)2-]". . p. 1627 - 1629. Retrieved 2001.
• 5、 Zolfigol, Mohammad Ali,Mallakpour, Shadpour E.. "A convenient method for the oxidation of urazoles to their corresponding triazolinediones under mild and heterogeneous conditions with sodium nitrate and oxalic dihydrate". . p. 4061 - 4069. Retrieved 1999.
• 6、 Zolfigol, Mohammad Ali,Borazjani, Maryam Kiany,Mallakpour, Shadpour E.,Nasr-Isfahani, Hossein. "An efficient method for the oxidation of urazoles under mild and heterogeneous conditions". . p. 2573 - 2585. Retrieved 2000.
• 7、 Zolfigol, Mohammad Ali,Salehi, Peyman,Mallakpour, Shadpour E.,Torabi, Mehdi. "1,4-Diazabicyclo[2.2.2]octane 1,4-bis(oxide)-bis(hydrogen peroxide)/MClx as a novel heterogeneous system for the oxidation of urazoles under mild conditions". . p. 1673 - 1674. Retrieved 2003.
• 8、 Nelsen, Stephen F.,Petillo, Peter A.,Chang, Hao,Frigo, Timothy B.,Dougherty, Dennis A.,Kaftory, Menahem. "Effects of CNN Bond Angle Restriction in 2,3-Diazabicyclohexane Derivatives on Nitrogen Inversion Barrier, Ease of Oxidation, and Acidity". . p. 613 - 618. Retrieved 1991.
• 9、 -. "Preparation of 2-(alkylcarbamoyl)hydrazine-1-carboxylic acid alkyl ester or its corresponding urazole salt". Paragraph 0155-0157. . Retrieved 2021/06/23.