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479403 Sigma-Aldrich

1,5,5-Trimethylhydantoin

98%

Synonym: 1,5,5-Trimethyl-2,4-imidazolidinedione, 3,4,4-Trimethyl-2,5-dioxoimidazolidine

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Properties

Related Categories Building Blocks, Chemical Synthesis, Heterocyclic Building Blocks, Imidazolines/Imidazolidines
Quality Level   200
assay   98%
mp   161-164 °C (lit.)
SMILES string   CN1C(=O)NC(=O)C1(C)C
InChI   1S/C6H10N2O2/c1-6(2)4(9)7-5(10)8(6)3/h1-3H3,(H,7,9,10)
InChI key   ZNYIPTYJBRGSSL-UHFFFAOYSA-N

Description

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

Packaging

10 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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