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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

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About This Item

Empirical Formula (Hill Notation):
C5H6Cl2N2O2
CAS Number:
118-52-5
Molecular Weight:
197.02
Beilstein:
146013
EC Number:
204-258-7
MDL number:
MFCD00003190
UNSPSC Code:
12352100
PubChem Substance ID:
24853931
NACRES:
NA.22

form

powder

Quality Level

200

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

Signal Word

Danger

Hazard Statements

H272,H302,H315,H317,H410

Hazard Classifications

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

Supplementary Hazards

EUH031

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS9284
MKCR2638
MKCM7829
MKCG5830
MKBK2690V

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Radovan Buffa et al.
Carbohydrate polymers, 250, 116928-116928 (2020-10-15)
Electron-deficient chlorine covalently immobilised on an amido group of hyaluronic acid (HA) can be potentially exceptional for applications requiring biodegradable and biocompatible polymers with enhanced antibacterial or antiviral activity. This expectation is supported by the assumption that a small amount
a-Chlorination of Acetophenones Using 1, 3-Dichloro-5, 5-Dimethylhydantoin.
Xu Z, et al.
Synthetic Communications, 36(2), 255-258 (2006)
Oxidation of urazoles with 1, 3-dihalo-5, 5-dimethylhydantoin, both in solution and under solvent-free conditions.
Zolfigol MA, et al.
Synlett, 5, 761-764 (2005)
[Hygienic evaluation of the possible use of 1,3-dichloro-5,5-dimethylhydantoin for the purpose of drinking water decontamination].
A A Semenova et al.
Gigiena i sanitariia, (3)(3), 11-13 (1982-03-01)
Akihiro Ohkubo et al.
The Journal of organic chemistry, 74(7), 2817-2823 (2009-03-03)
New 3'-terminal deoxyribonucleoside-loading reagents having a silyl-type linker were developed. They were effectively introduced into polymer supports under the conditions of Huisgen [3 + 2] cycloaddition without base protection. Moreover, four unmodified DNA oligomers d[TACCTAAATCCAX] (X = T, A, C
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