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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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Yaws CL.
Thermophysical Properties of Chemicals and Hydrocarbons, 280-280 (2008)
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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