N,N'-Dimethylparabanic acid

Base Information

• Chemical Name: N,N'-Dimethylparabanic acid
• CAS No.: 5176-82-9
• Molecular Formula: C5H6 N2 O3
• Molecular Weight: 142.114
• Hs Code.: 2933990090
• European Community (EC) Number: 823-921-7
• UNII: 0HX0078PZH
• DSSTox Substance ID: DTXSID70966068
• Nikkaji Number: J8.817J
• Wikidata: Q27236792
• Mol file: 5176-82-9.mol

Synonyms:N,N'-dimethylparabanic acid;N,N'-DMPA

Chemical Property of N,N'-Dimethylparabanic acid

Chemical Property:

• Vapor Pressure: 0.00493mmHg at 25°C
• Boiling Point: 276°Cat760mmHg
• Flash Point: 133.6°C
• PSA: 57.69000
• Density: 1.416g/cm³
• LogP: -1.08740
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 142.03784206
• Heavy Atom Count: 10
• Complexity: 201

Purity/Quality:

99% ^*data from raw suppliers

1,3-DimethylparabanicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=O)C(=O)N(C1=O)C
• Uses: Chronic exposure to 1,3-Dimethylparabanic Acid can cause inhibition of growth population on rotifers while algae seems to be unaffected. Furthermore, 1,3-Dimethylparabanic Acid is a derivative of Caffeine (C080100). Caffeine is a bitter, white crystalline xanthine alkaloid that acts as a stimulant drug and a reversible acetylcholinesterase inhibitor. Caffeine is found in varying quantities in the seeds, leaves, and fruit of some plants, where it acts as a natural pesticide that paralyzes and kills certain insects feeding on the plants. In humans, caffeine acts as a central nervous system stimulant, temporarily warding off drowsiness and restoring alertness. Caffeine is a cardiac and respiratory stimulant; diuretic. Caffeine is toxic at sufficiently high doses.A study at Johns Hopkins U

Technology Process of N,N'-Dimethylparabanic acid

There total 26 articles about N,N'-Dimethylparabanic acid 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: 85.0%

N,N'-Dimethylurea (96-31-1) + oxalic acid diethyl ester (95-92-1) → 1,3-dimethylparabanic acid (5176-82-9) + Ethyl N-methylcarbamate (105-40-8) + ethyl N-methyloxamate (18522-95-7)

Guidance literature:

With di(n-butyl)tin oxide; at 140 ℃; for 12h; Inert atmosphere;

DOI:10.1002/aoc.1629

Reference yield: 73.0%

Dimethyl oxalate (553-90-2) + N,N'-Dimethylurea (96-31-1) → 1,3-dimethylparabanic acid (5176-82-9) + methyl N-methylcarbamate (6642-30-4) + methyl 2-(methylamino)-2-oxoacetate (54154-11-9)

Guidance literature:

With di(n-butyl)tin oxide; at 140 ℃; for 12h; Inert atmosphere;

DOI:10.1002/aoc.1629

Reference yield: 41.0%

1,3-dimethyluracil (874-14-6,156398-76-4) → 1,3-dimethylparabanic acid (5176-82-9) + 1,3-dimethyl-5-hydroxyuracil (20406-86-4) + 6-hydroxy-1,3-dimethyluracil (41949-07-9)

Guidance literature:

With Oxone<*>; In acetone; for 57.6h; Product distribution; Ambient temperature; with or without solvent, with or without camphor;

upstream raw materials:

4-hydroxy-1,3-dimethyl-2,5-dioxo-imidazolidine-4-carboxylic acid methylamide

1,3-dimethyluracil

3-chloro-benzenecarboperoxoic acid

1,3-dimethylthymine

Downstream raw materials:

N,N'-dimethyl-5-hydroxy-5-(3-hydroxy-1,1-diphenylpropyl)hydantoin

N,N'-dimethyl-5-hydroxy-5-(2-methoxy-1,1-diphenylethyl)hydantoin

N,N'-dimethyl-5-hydroxy-5-(3-hydroxy-1,1-diphenylbutyl)hydantoin

spiro

Refernces

• 1、 Kunde, Lalita B.,Kalyani, Vishwanath S.,Gupte, Sunil P.. "Dibutyltin oxide catalyzed aminolysis of oxalate to carbamate, oxamate and derivatives of imidazolidine trione". experimental part. p. 402 - 407. Retrieved 2010/08/06.
• 2、 Hong, Yongrae,Chang, Soonjae,Hahn, Bosup,Toda, Fumio. "Oxidation of 1,3-dimethylthymine and 1,3-dimethyluracil with oxone in the solid to solid state". . p. 1455 - 1459. Retrieved 2007/10/03.