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232807

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24853931
EC Number:
204-258-7
Beilstein/REAXYS Number:
146013
MDL number:
MFCD00003190
Form:
powder
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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

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

signalword

Danger

Hazard Classifications

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

supp_hazards

EUH031

Storage Class

5.1B - Oxidizing hazardous materials

wgk

WGK 2

flash_point_f

345.2 °F

flash_point_c

174 °C

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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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)
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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Global Trade Item Number

SKUGTIN
232807-1KG04061838347558
232807-250G04061838783783