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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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$52.52
1 KG
$98.03

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250 G
$52.52
1 KG
$98.03

About This Item

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

$52.52

List Price$65.90Save 20%

In StockDetails

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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

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Application

1,3-Dichloro-5,5-dimethylhydantoin was used:
  • in reaction of chlorination of cytosine base[1]
  • in the synthesis of α-chloroacetophenones[2]
  • as an effective oxidizing agent for the oxidation of urazoles and bis-urazoles to their corresponding triazolinediones[3]
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

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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_germany

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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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
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)
[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)
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)
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Questions

1–2 of 2 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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