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479403

Sigma-Aldrich

1,5,5-Trimethylhydantoin

98%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C6H10N2O2
CAS Number:
6851-81-6
Molecular Weight:
142.16
EC Number:
229-945-9
MDL number:
MFCD00040439
UNSPSC Code:
12352100
PubChem Substance ID:
24871615
NACRES:
NA.22

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

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Yaws CL.
Thermophysical Properties of Chemicals and Hydrocarbons, 280-280 (2008)
Mass spectrometric analysis and theoretical calculations of the occurrence of tautomeric structures of hydantoins.
Allegretti PE, et al.
Afinidad, 57(485), 41-49 (2000)
Use of the cascade α-oxo-amidoalkylation/transposition/Π-cationic cyclization of N-acyliminium ions in the synthesis of novel fused heterocyclic N,O-acetals.
Pesquet A, et al.
ARKIVOC (Gainesville, FL, United States), 8, 27-40 (2010)
Zi-Ao Huang et al.
Electrophoresis, 41(3-4), 183-193 (2019-12-19)
In this paper, the development of a simple dilute-and-shoot method for quantifying urinary creatinine by CE-ESI-MS was described. The creatinine analysis time was about 7 min/sample by conventional single injection (SI) method and can be significantly reduced to less than 2 min/sample

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