1,5,5-Trimethylhydantoin - 10mM in DMSO , CAS No.6851-81-6

CAS: 6851-81-6 Cat. No.: T425454 Molecular Weight: 142.16 Beilstein Registry Number: 24(5)5,352 EC Number: 229-945-9 PubChem CID: 81295

GRADE & PURITY 10mM in DMSO

Synonyms

DTXSID40218642 | T1739 | HMS1720F02 | 1,5,5 trimethylhydantoin | D92516 | 6HQ | 1,5,5-Trimethylhydantoin; LC-tDDA; CE10 | (S)-UH-301 | HY-W012606 | W-104663 | (2,5-dioxopyrrolidin-1-yl) 4-azidobenzoate | MFCD00040439 | 1,5,5-Trimethylimidazolidine-2,4-dio

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

General description：

1,5,5-Trimethylhydantoin (TMH) is a 1,5,5-trisubstituted hydantoin. Its mass spectrum has been recorded and analyzed. The density of TMH is 1.1318g/ml at 25°C.

application：

1,5,5-Trimethylhydantoin (1,5,5-Trimethyl-imidazolidine-2,4-dione) may be used to synthesize 3-bromomethyl-1,5,5-trimethylimidazolid-ine-2,4-dione.

Reactant for:

Z-selective hydroamidation of terminal alkynes with secondary amides and imides

Selective inhibitors of hepatitis C virus NS3 serine protease

Stereoselective addition of imides to alkynes

Reactant for synthesis of:

Selective angiotensin II AT2 receptor agonists with reduced CYP 450 inhibition

N-chlorohydantoins

P2X7 receptor antagonists

Specifications

Synonyms

DTXSID40218642 | T1739 | HMS1720F02 | 1, 5, 5 trimethylhydantoin | D92516 | 6HQ | 1, 5, 5-Trimethylhydantoin; LC-tDDA; CE10 | (S)-UH-301 | HY-W012606 | W-104663 | (2, 5-dioxopyrrolidin-1-yl) 4-azidobenzoate | MFCD00040439 | 1, 5, 5-Trimethylimidazolidine-2, 4-dio

Specifications & Purity

10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Canonical Smiles: CC1(C(=O)NC(=O)N1C)C
• IUPAC Name: 1,5,5-trimethylimidazolidine-2,4-dione
• InChIKey: ZNYIPTYJBRGSSL-UHFFFAOYSA-N
• INCHI: 1S/C6H10N2O2/c1-6(2)4(9)7-5(10)8(6)3/h1-3H3,(H,7,9,10)
• Isomeric SMILES: CC1(C(=O)NC(=O)N1C)C
• WGK Germany: 3
• PubChem CID: 81295
• Molecular Weight: 142.16
• Beilstein: 24(5)5,352
• Reaxy-Rn: 120651

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Azolidines
      • Subclass Imidazolidines
        • Level5 Imidazolidinones
          • Level6 Imidazolidinediones
            • Level7 Hydantoins

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Azolidines
• Subclass: Imidazolidines
• Intermediate Tree Nodes: Imidazolidinones - Imidazolidinediones
• Direct Parent: Hydantoins
• Alternative Parents: Alpha amino acids and derivatives N-acyl ureas Dicarboximides Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Hydantoin - Alpha-amino acid or derivatives - N-acyl urea - Ureide - Dicarboximide - Urea - Carbonic acid derivative - Carboxylic acid derivative - Azacycle - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Melt Point(°C): 161-164°C
• Molecular Weight: 142.160 g/mol
• XLogP3: -0.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 142.074 Da
• Monoisotopic Mass: 142.074 Da
• Topological Polar Surface Area: 49.400 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 198.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Jing Wang, Haijun Bi, Mengru Li, Hui Wang, Manman Xue, Jieyao Yu, Chi-Tang Ho, Liang Zhang, Qinglin Zhuo, Jiadao Jiang, Xiaochun Wan, Xiaoting Zhai.  (2023)  Contribution of theanine to the temperature-induced changes in aroma profile of Wuyi rock tea.  FOOD RESEARCH INTERNATIONAL,      [PMID:37254434] [10.1016/j.foodres.2023.112860]

2. Xiao Tu, Jiaxin Hu, Jinghao Peng, Qihan Chen, Yangle Zhao, Zemao Gu.  (2025)  Discovery of thymoquinone analogues with high anthelmintic activity against monogenean infections in goldfish (Carassius auratus).  VETERINARY PARASITOLOGY,      [PMID:39837239] [10.1016/j.vetpar.2025.110401]