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232807

Sigma-Aldrich

1,3-Dichloro-5,5-dimethylhydantoin

available chlorine 68 %

Synonym(s):
1,3-Dichloro-5,5-dimethyl-2,4-imidazolidinedione, DCDMH, NSC 33307, NSC 38630
Empirical Formula (Hill Notation):
C5H6Cl2N2O2
CAS Number:
Molecular Weight:
197.02
Beilstein:
146013
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

powder

Quality Level

composition

available chlorine, 68%

mp

132-134 °C (lit.)

solubility

water: soluble 0.21% at 25 °C(lit.)
carbon tetrachloride: freely soluble 12.5%(lit.)
chloroform: freely soluble 14%(lit.)
methylene chloride: freely soluble 30%(lit.)
benzene: freely soluble 9.2%(lit.)
chlorinated solvents: freely soluble at 25 °C(lit.)

SMILES string

CC1(C)N(Cl)C(=O)N(Cl)C1=O

InChI

1S/C5H6Cl2N2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3

InChI key

KEQGZUUPPQEDPF-UHFFFAOYSA-N

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Application

1,3-Dichloro-5,5-dimethylhydantoin was used:
  • in reaction of chlorination of cytosine base
  • in the synthesis of α-chloroacetophenones
  • as an effective oxidizing agent for the oxidation of urazoles and bis-urazoles to their corresponding triazolinediones
Reagent involved in:
  • Microwave-assisted aromatization of trisubstituted pyrazolines
  • Asymmetric chlorolactonization chlorenium source
  • Oxidative chlorination for the synthesis of arenesulfonyl chlorides
  • Selective halogenation for the synthesis of halo ketones
  • Chlorination reactions

Packaging

250 g in glass bottle
1 kg in glass bottle

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Ox. Sol. 2 - Skin Irrit. 2 - Skin Sens. 1

Supplementary Hazards

Storage Class Code

5.1B - Oxidizing hazardous materials

WGK

WGK 2

Flash Point(F)

345.2 °F

Flash Point(C)

174 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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