118-52-5

Basic information

• Product Name: 1,3-Dichloro-5,5-dimethylhydantoin
• Synonyms: DCDMH;DANTOIN;DACTIN;DICHLORO-DIMETHYL-HYDANTOINE;1,3-DICHLORO-5,5-DIMETHYL-2,4-IMIDAZOLIDINEDIONE;1,3-DICHLORO-5,5-DIMETHYLHYDANTOIN;1,3-DICHLORO-5,5-DIMETHYLHYDANTOINE;1,3-dichloro-5,5’-methylhydantoin
• CAS NO: 118-52-5
• Molecular Formula: C₅H₆Cl₂N₂O₂
• Molecular Weight: 197.02
• EINECS: 204-258-7
• Product Categories: Miscellaneous;Water treatment chemicals;Water Ttreatment Chemicals;Imidazolines/ImidazolidinesBuilding Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Imidazolines/Imidazolidines;water treatment;Pyridines
• Mol File: 118-52-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 132-134 °C(lit.)
• Boiling Point: 214.7 °C at 760 mmHg
• Flash Point: 171 °C
• Appearance: White/Crystalline Powder
• Density: 1,5 g/cm3
• Vapor Pressure: 0.153mmHg at 25°C
• Refractive Index: 1.5720 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: water: soluble0.21% at 25°C(lit.)
• PKA: -3.44±0.40(Predicted)
• Water Solubility: 0.21 g/100 mL (25 ºC)
• Sensitive: Moisture Sensitive
• Stability: Stable, but a strong oxidizer - contact with combustible material may lead to fire. Incompatible with reducing agents, acids, st
• Merck: 14,3065
• BRN: 146013
• CAS DataBase Reference: 1,3-Dichloro-5,5-dimethylhydantoin(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dichloro-5,5-dimethylhydantoin(118-52-5)
• EPA Substance Registry System: 1,3-Dichloro-5,5-dimethylhydantoin(118-52-5)

Safety Data

• Hazard Codes: Xn,C,O,N
• Statements: 22-36/37/38-34-8-50-43-31-20/21/22
• Safety Statements: 26-36-45-36/37/39-17-61
• RIDADR: UN 1479 5.1/PG 2
• WGK Germany: 3
• RTECS: MU0700000
• TSCA: Yes
• HazardClass: 5.1
• PackingGroup: II
• Hazardous Substances Data: 118-52-5(Hazardous Substances Data)

Usage

Chemical Properties

DCDMH is a combustible, white powder. Chlorine-like odor.

Physical properties

White powder or four-sided crystals from chloroform with a chlorine-like odor. Aqueous solutions are acidic.

Uses

Different sources of media describe the Uses of 118-52-5 differently. You can refer to the following data:
1. Chlorinating agent; disinfectant; laundry bleach; in water treatment; intermediate for drugs; insecticides; polymerization catalyst
2. Dantoin(R) DCDMH is an industrial bleaching agent based on dimethyl hydantoin. This product finds application wherever solid bleach is desired.
3. Dantoin(R) DCDMH LD (low dust) is an industrial bleaching agent based on dimethyl hydantoin. This product finds application wherever solid bleach is desired.

Definition

Methionine hydroxy analog c. 90%.

General Description

White powder with a weak chlorine odor. Conflagrates at 414°F (turns brown). Chlorine gas evolves > 410°F.

Air & Water Reactions

Sensitive to exposure to light, air, and moisture. Reacts with water or steam to produce toxic and corrosive fumes.

Reactivity Profile

1,3-Dichloro-5,5-dimethylhydantoin reacts violently with xylene. 1,3-Dichloro-5,5-dimethylhydantoin is incompatible with strong acids, easily oxidized materials, ammonia salts and sulfides. 1,3-Dichloro-5,5-dimethylhydantoin will react with water or steam to produce toxic and corrosive fumes. At a pH of 9, 1,3-Dichloro-5,5-dimethylhydantoin decomposes completely.

Health Hazard

1,3-Dichloro-5,5-dimethylhydantoin powder in contact with water yields hypochlorous acid, which is an irritant of the eyes and mucous membranes.

Fire Hazard

Flash point data for 1,3-Dichloro-5,5-dimethylhydantoin are not available. 1,3-Dichloro-5,5-dimethylhydantoin is probably combustible.

Safety Profile

Moderately toxic by ingestion. Mildly toxic by inhalation. A severe slun irritant. Mutation data reported. Avoid excessive contact because of effects of active chlorine on skin. Some of the hydantoins are central nervous system depressants. Mixtures with xylene may explode. Wdl react with water or steam to produce toxic and corrosive fumes. When heated to decomposition it emits toxic fumes of Cl and NOx. See also CHLORIDES.

Potential Exposure

It is used as a chlorinating agent, disinfectant, biocide, and laundry bleach. It is also used as a polymerization catalyst in making vinyl chloride; and in drug and pesticide synthesis.

Environmental fate

Chemical/Physical. Reacts with water (pH 7.0) releasing hypochlorous acid. At pH 9, nitrogen chloride is formed (Windholz et al., 1983).

Shipping

UN1479 Oxidizing solid, n.o.s., Hazard Class: 5.1; Labels: 5.1-Oxidizer, Technical Name Required

Purification Methods

Purify it by dissolving in conc H2SO4 and diluting with ice H2O, collect the solid, dry it in a vacuum and recrystallise it from CHCl3. It sublimes at 100o in a vacuum. It exhibits time-dependent hydrolysis at pH 9. [Petterson & Grzeskowiak J Org Chem 24 1414 1959, Beilstein 24 III/IV 1100.]

Incompatibilities

A strong oxidizer. Contact with water forms poisonous and corrosive gases. Mixtures with xylene may explode. Not compatible with moisture (especially hot water, steam), strong acids; easily oxidized materials (such as ammonia salts; sulfides, etc.); reducing agents; strong bases; ammonium salts; sulfides. Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides (releasing heat, toxic and possibly flammable gases), thiosulfates and dithionites (releasing hydrogen sulfate and oxides of sulfur)

Waste Disposal

Incineration (815.5C/816C, 0.5 second for primary combustion; 104.4C/220F, 1.0 second for secondary combustion). The formation of elemental chlorine can be prevented by injection of steam or methane into the combustion process. Any nitrogen oxides may be abated by the use of thermal or catalytic devices

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

Synthetic route

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) → 1,3-dichloro-5,5-dimethylhydantoin (118-52-5)

Conditions	Yield
Stage #1: 5,5-dimethyl-imidazolidine-2,4-dione With sodium carbonate at 20℃; for 6h; Stage #2: With chlorine In tetrahydrofuran; ethyl acetate at 100℃; for 7h; Concentration; Microwave irradiation;	98.72%
With trichloroisocyanuric acid In acetonitrile at 20℃; for 0.5h;	87%
With water; chlorine at 8 - 10℃;

sodium cyanide (143-33-9) + acetone (67-64-1) + 2CO3 → 1,3-dichloro-5,5-dimethylhydantoin (118-52-5)

Conditions	Yield
With water anschliessend mit wss. NaOH und Chlor;
With water anschliessend mit wss. KOH und Chlor;

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + aqueous Na2CO3 → 1,3-dichloro-5,5-dimethylhydantoin (118-52-5)

Conditions	Yield
With chlorine

(1-Cyan-1-methylethyl)harnstoff (79662-84-3) → 1,3-dichloro-5,5-dimethylhydantoin (118-52-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrochloric acid 2: water; chlorine / 8 - 10 °C View Scheme

isoquinoline (119-65-3) + 1,3-dichloro-5,5-dimethylhydantoin (118-52-5) → 5,8-dichloroisoquinoline (73075-59-9)

Conditions	Yield
Stage #1: isoquinoline With sulfuric acid at 2 - 21℃; for 0.25h; Stage #2: 1,3-dichloro-5,5-dimethylhydantoin at 10 - 55℃; for 18.5h; regioselective reaction;	98%

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) → 1,3-di(chlorothio)-5,5-dimethylhydantoin (104867-38-1)

Conditions	Yield
With tetraethylammonium bromide; sulfur In 1,2-dichloro-ethane 1.) 50 deg C, 1 hr., 2.) 80 deg C, 30 min.;	92%

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + 2-Ethylhexyl alcohol (104-76-7) → benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid (1390661-72-9)

Conditions	Yield
With triethylamine	84%

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + methyl 3-(benzylthio)-4-cyclopropylbenzoate → methyl 3-(chlorosulfonyl)-4-cyclopropylbenzoate

Conditions	Yield
With acetic acid In water; acetonitrile at -10℃; for 3h;	80%

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + 4-amino-5-fluoro-6-(4-fluorobenzyl)picolinaldehyde (1613459-80-5) → 4-amino-3-chloro-5-fluoro-6-(4-fluorobenzyl)picolinaldehyde (1613459-88-3)

Conditions	Yield
In acetonitrile	73.7%

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + 4-amino-6-(tert-butyl)-5-fluoropicolinaldehyde (1613459-77-0) → 4-amino-6-(tert-butyl)-3-chloro-5-fluoropicolinaldehyde (1652602-09-9)

Conditions	Yield
In acetonitrile	70.5%

N-Methylpyrrole (96-54-8) + 1,3-dichloro-5,5-dimethylhydantoin (118-52-5) → 3-(1-methyl-1H-pyrrol-2-yl)-5,5-dimethylhydantoin + 1,3-di-(1-methyl-1H-pyrrol-2-yl)-5,5-dimethylhydantoin

Conditions	Yield
With sodium hydrogencarbonate In chloroform for 57h;	A 70% B 28%

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + benzaldehyde (100-52-7) → 3-benzoyl-5,5-dimethylimidazolidine-2,4-dione (1886-18-6)

Conditions	Yield
With iron(III) chloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate In water; acetonitrile at 35℃; for 2.5h; Sealed tube; Inert atmosphere;	70%

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + 4-amino-3-fluoro-6'-(trifluoromethyl)-[2,3'-bipyridine]-6-carbaldehyde (1613459-81-6) → 4-amino-5-chloro-3-fluoro-6'-(trifluoromethyl)-[2,3'-bipyridine]-6-carbaldehyde (1613459-89-4)

Conditions	Yield
In acetonitrile	69.8%

4-Methoxystyrene (637-69-4) + 1,3-dichloro-5,5-dimethylhydantoin (118-52-5) → (+/-)-1-chloro-2-hydroxy-2-(p-methoxyphenyl)ethane (4973-18-6) + 1-chloro-3-(2-chloro-1-(4-methoxyphenyl)ethyl)-5,5-dimethylimidazolidine-2,4-dione (1332928-55-8)

Conditions	Yield
With (2S,3S)-3-hydroxy-2-(4-methylphenylsulfonamido)butanoic acid; water In acetone at 20℃; for 1h; regioselective reaction;	A 62% B 23%

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + benzyl alcohol (100-51-6) → benzaldehyde (100-52-7) + 3-benzoyl-5,5-dimethylimidazolidine-2,4-dione (1886-18-6)

Conditions	Yield
With iron(III) chloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate In water; acetonitrile at 35℃; for 1h; Reagent/catalyst; Sealed tube; Inert atmosphere;	A 35% B 62%
With iron(III) chloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate In water; acetonitrile at 35℃; for 1h; Sealed tube; Inert atmosphere;	A 52% B 44%

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + 4-amino-6-cyclobutyl-5-fluoropicolinaldehyde (1613459-79-2) → 4-amino-3-chloro-6-cyclobutyl-5-fluoropicolinaldehyde (1652602-11-3)

Conditions	Yield
In acetonitrile	45.7%

3-(3,5-di-t-butyl-4-hydroxybenzoyl)pyrrole (116689-10-2) + 1,3-dichloro-5,5-dimethylhydantoin (118-52-5) → 2-chloro-4-(3,5-di-t-butyl-4-hydroxybenzoyl)pyrrole

Conditions	Yield
In hexane; dichloromethane; ethyl acetate; acetone	43%

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + N,N-bis(p-methoxybenzyl)amine (17061-62-0) + 2-(3-(benzylthio)-4-fluorophenyl)ethanol → 2-fluoro-5-(2-hydroxyethyl)-N,N-bis(4-methoxybenzyl)benzenesulfonamide

Conditions	Yield
Stage #1: 1,3-dichloro-5,5-dimethylhydantoin; 2-(3-(benzylthio)-4-fluorophenyl)ethanol With acetic acid In water at -10℃; for 4h; Stage #2: N,N-bis(p-methoxybenzyl)amine With triethylamine In dichloromethane at 0 - 20℃; for 18h;	32%

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + 2,5-dioxopyrrolidin-1-yl (2S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate (3496-11-5) + tert-butyl carbamate (4248-19-5) + C15H19NO4 → C18H25N3O5

Conditions

Yield

Stage #1: 1,3-dichloro-5,5-dimethylhydantoin; tert-butyl carbazate; C15H19NO4 With potassium osmate(VI) dihydrate; water; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; sodium hydroxide; potassium hexacyanoferrate(III) In propan-1-ol at 20 - 25℃; for 16h; Stage #2: With palladium 10% on activated carbon; hydrogen In ethyl acetate at 40℃; under 2068.65 Torr; for 2h; Stage #3: 2,5-dioxopyrrolidin-1-yl (2S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate Further stages;

31%

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + 4-amino-6-(cyclopropylmethyl)-5-fluoropicolinaldehyde (1613459-78-1) → 4-amino-3-chloro-6-(cyclopropylmethyl)-5-fluoropicolinaldehyde (1613459-87-2)

Conditions	Yield
In acetonitrile	23.44%

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + 4-amino-5-fluoro-6-(tetrahydrofuran-2-yl)picolinaldehyde (1613459-83-8) → 4-amino-3-chloro-5-fluoro-6-(tetrahydrofuran-2-yl)picolinaldehyde (1613459-90-7)

Conditions	Yield
In acetonitrile	10.14%

tetrachloromethane (56-23-5) + 1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + antipyrine (60-80-0) + dibenzoyl peroxide (94-36-0) → 4-chloro-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one (43068-92-4)

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + antipyrine (60-80-0) → 4-chloro-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one (43068-92-4)

Conditions	Yield
With tetrachloromethane; dibenzoyl peroxide

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + 2-Methoxynaphthalene (93-04-9) → 1-chloro-2-methoxynaphthalene (13101-92-3)

Conditions	Yield
With tetrachloromethane

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + 2-ethoxynaphthalene (93-18-5) → ethyl-(1-chloro-[2]naphthyl)-ether (85972-71-0)

Conditions	Yield
With tetrachloromethane

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + 2,5-dimethoxy toluene (24599-58-4) → 2,5-dimethoxybenzyl chloride (3840-27-5) + 2-Chloro-5-methyl-1,4-dimethoxybenzene (2675-78-7)

Conditions	Yield
With tetrachloromethane; dibenzoyl peroxide

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + 1-acetamidonaphthalene (575-36-0) → N-(4-chloro-[1]naphthyl)-acetamide (105789-74-0)

Conditions	Yield
With chloroform

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + 2-acetylaminonaphthalene (581-97-5) → 1-chloro-2-acetylaminonaphthalene (105789-95-5)

Conditions	Yield
With chloroform

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + pregna-4,9(11)-diene-3,20-dione-17-hydroxy-21-methyl (34184-82-2) → 9-chloro-11β,17-dihydroxy-pregn-4-ene-3,20-dione (24916-89-0)

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + 16α-acetoxy-17-hydroxy-pregna-4,9(11)-diene-3,20-dione (96709-11-4) → 16α-acetoxy-9-chloro-11β,17-dihydroxy-pregn-4-ene-3,20-dione (96674-82-7)

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + 1-chloro-2,2-bis(p-chlorophenyl)ethylene (1022-22-6) + acetic acid (64-19-7) → 1-acetoxy-2,2-dichloro-1,1-bis-(4-chloro-phenyl)-ethane (79133-04-3)

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + methoxybenzene (100-66-3) → 4-chloromethoxybenzene (623-12-1)

1,3-dichloro-5,5-dimethylhydantoin (118-52-5) + naphthalen-2-ylamine (91-59-8) → 1-chloro-2-aminonaphthalene (16452-11-2)

Conditions	Yield
With tetrachloromethane

Upstream product

• 79662-84-3 (1-Cyan-1-methylethyl)harnstoff 
• 77-71-4 5,5-dimethyl-imidazolidine-2,4-dione 
• 143-33-9 sodium cyanide 
• 67-64-1 acetone 

Downstream Products

• 6921-17-1 1-chloro-5,5-dimethylhydantoin 
• 77-48-5 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione 
• 123-11-5 4-methoxy-benzaldehyde 
• 1390661-72-9 benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid 
• 72-80-0 chloroquinaldol 

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Chemiluminescence flow injection analysis of 1,3-Dichloro-5,5-dimethylhydantoin (cas 118-52-5) in swimming pool water08/28/2019

A new chemiluminescence (CL) flow-injection method is proposed for the determination of 1,3-dichloro-5,5-dimethylhydantoin (DDH). The method is based on the chemiluminescent reaction of DDH and luminol–H2O2 in an alkaline medium (pH 12.0–12.5). The concentration of the analyte shows a good lin...detailed

Silica-supported 1,3-Dichloro-5,5-dimethylhydantoin (cas 118-52-5) (DCH) as a useful reagent for microwave-assisted aromatization of 1,3,5-trisubstituted pyrazolines under solvent-free conditions08/27/2019

1,3,5-Trisubstituted pyrazolines are rapidly and conveniently oxidized to their corresponding pyrazoles by 1,3-dichloro-5,5-dimethylhydantoin (DCH) in solution and solvent-free conditions under microwave irradiation. The presence of silica gel as a supporting agent is shown to be effective in re...detailed

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