| Identification | More | [Name]
1,3-Dichloro-5,5-dimethylhydantoin | [CAS]
118-52-5 | [Synonyms]
1,3-DICHLORO-5,5-DIMETHYL-2,4-IMIDAZOLIDINEDIONE
1,3-DICHLORO-5,5-DIMETHYLHYDANTOIN
1,3-DICHLORO-5,5-DIMETHYLHYDANTOINE
DACTIN
DANTOIN
DCDMH
DICHLORO-DIMETHYL-HYDANTOINE
1,3-dichloro-5,5’-methylhydantoin
1,3-dichloro-5,5-dimethyl-4-imidazolidinedione
1,3-dichloro-5,5-dimethyl-hydantoi
1,3-dwuchloro-5,5-dwumetylohydantoina
4-Imidazolidinedione,1,3-dichloro-5,5-dimethyl-2
daktin
dichlorantin
dichloro-5,5-dimethylhydantoin
dichlorodimethyl-hydantoi
dichlorodimethylhydantoin
dwuchlorantyny
halane
hydan | [EINECS(EC#)]
204-258-7 | [Molecular Formula]
C5H6Cl2N2O2 | [MDL Number]
MFCD00003190 | [Molecular Weight]
197.02 | [MOL File]
118-52-5.mol |
| Chemical Properties | Back Directory | [Definition]
Methionine hydroxy analog c. 90%. | [Appearance]
Powder | [Melting point ]
132-134 °C (lit.) | [Boiling point ]
214.7±23.0 °C(Predicted) | [density ]
1,5 g/cm3 | [vapor pressure ]
0.003Pa | [refractive index ]
1.5720 (estimate) | [Fp ]
171 °C
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
water: soluble0.21% at 25°C(lit.) | [form ]
Crystalline Powder | [pka]
-3.44±0.40(Predicted) | [color ]
White | [PH]
4.4 (H2O)(HSDB) | [Stability:]
Stable, but a strong oxidizer-contact with combustible material may lead to fire. Incompatible with reducing agents, acids, strong bases. Moisture sensitive. | [Water Solubility ]
0.21 g/100 mL (25 ºC) | [Sensitive ]
Moisture Sensitive | [Usage]
Dantoin(R) DCDMH LD (low dust) is an industrial bleaching agent based on dimethyl hydantoin. This product finds application wherever solid bleach is desired. | [Merck ]
14,3065 | [Sublimation ]
100 ºC | [BRN ]
146013 | [Henry's Law Constant]
9.9×100 mol/(m3Pa) at 25℃, HSDB (2015) | [Exposure limits]
NIOSH REL: TWA 0.2, STEL 0.4, IDLH 5; OSHA PEL: TWA 0.2,
STEL/C 0.4 (adopted). | [InChI]
1S/C5H6Cl2N2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3 | [InChIKey]
KEQGZUUPPQEDPF-UHFFFAOYSA-N | [SMILES]
CC1(C)N(Cl)C(=O)N(Cl)C1=O | [LogP]
-0.94 | [CAS DataBase Reference]
118-52-5(CAS DataBase Reference) | [EPA Substance Registry System]
118-52-5(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
  
GHS03,GHS07,GHS09 | [Signal word ]
Danger | [Hazard statements ]
H272-H302-H315-H317-H410 | [Precautionary statements ]
P210-P220-P273-P280-P301+P312-P302+P352 | [Hazard Codes ]
Xn,C,O,N | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R34:Causes burns.
R8:Contact with combustible material may cause fire.
R50:Very Toxic to aquatic organisms.
R43:May cause sensitization by skin contact.
R31:Contact with acids liberates toxic gas.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S17:Keep away from combustible material .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [OEB]
C | [OEL]
TWA: 0.2 mg/m3, STEL: 0.4 mg/m3 | [RIDADR ]
UN 1479 5.1/PG 2
| [WGK Germany ]
3
| [RTECS ]
MU0700000
| [TSCA ]
Yes | [REACH Registrations]
Active | [HazardClass ]
5.1 | [PackingGroup ]
II | [HS Code ]
29332100 | [Storage Class]
5.1B - Oxidizing hazardous materials | [Hazard Classifications]
Acute Tox. 4 Oral
Aquatic Acute 1
Aquatic Chronic 1
Ox. Sol. 2
Skin Irrit. 2
Skin Sens. 1 | [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. | [Hazardous Substances Data]
118-52-5(Hazardous Substances Data) | [Toxicity]
LD50 oral in rabbit: 1520mg/kg | [IDLA]
5 mg/m3 |
| Hazard Information | Back Directory | [General Description]
White powder with a weak chlorine odor. Conflagrates at 414°F (turns brown). Chlorine gas evolves > 410°F. | [Reactivity Profile]
1,3-DICHLORO-5,5-DIMETHYLHYDANTOIN(118-52-5) reacts violently with xylene. 1,3-DICHLORO-5,5-DIMETHYLHYDANTOIN(118-52-5) is incompatible with strong acids, easily oxidized materials, ammonia salts and sulfides. 1,3-DICHLORO-5,5-DIMETHYLHYDANTOIN(118-52-5) will react with water or steam to produce toxic and corrosive fumes. At a pH of 9, 1,3-DICHLORO-5,5-DIMETHYLHYDANTOIN(118-52-5) decomposes completely. | [Air & Water Reactions]
Sensitive to exposure to light, air, and moisture. Reacts with water or steam to produce toxic and corrosive fumes. | [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. | [Fire Hazard]
Flash point data for this chemical are not available. 1,3-DICHLORO-5,5-DIMETHYLHYDANTOIN is probably combustible. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.
Medical observation is recommended for 24 to 48 hours
after breathing overexposure, as pulmonary edema may be
delayed. As first aid for pulmonary edema, a doctor or
authorized paramedic may consider administering a drug or
other inhalation therapy. | [Shipping]
UN1479 Oxidizing solid, n.o.s., Hazard Class:
5.1; Labels: 5.1-Oxidizer, Technical Name Required | [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) | [Description]
DCDMH is a combustible, white powder witha chlorine-like odor. Molecular weight=197.03; Freezing/Melting point=130℃; Flash point=175℃. HazardIdentification (based on NFPA-704 M Rating System):Health 3, Flammability 1, Reactivity 0 Oxidizer, . Waterreactive; slightly soluble; solubility=0.2%. | [Chemical Properties]
DCDMH is a combustible, white powder.
Chlorine-like odor. | [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 | [Physical properties]
White powder or four-sided crystals from chloroform with a chlorine-like odor. Aqueous solutions
are acidic. | [Uses]
Chlorinating agent; disinfectant;
laundry bleach; in water treatment; intermediate
for drugs; insecticides; polymerization
catalyst | [Uses]
Dantoin(R) DCDMH is an industrial bleaching agent based on dimethyl hydantoin. This product finds application wherever solid bleach is desired. | [Uses]
Dantoin(R) DCDMH LD (low dust) is an industrial bleaching agent based on dimethyl hydantoin. This product finds application wherever solid bleach is desired. | [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. | [Synthesis]
General procedure for the synthesis of 1,3-dichloro-5,5-dimethylimidazoline-2,4-dione from 5,5-dimethylhydantoin: Preparation of ethyl acetate, tetrahydrofuran and liquid chlorine in the ratio of 1:1:0.7 by volume, as well as 5,5-dimethylglycolide urea, anhydrous sodium carbonate and lanthanum-modified nanoscale Ga/Al composite solid bases in the ratio of 1:1.2:0.15 by mass. The specific dosage was as follows 30 mL of ethyl acetate, 30 mL of tetrahydrofuran, 21 mL of liquid chlorine, 7 g of 5,5-dimethylglycolide, 8.4 g of anhydrous sodium carbonate and 1.05 g of lanthanum-modified nanoscale Ga/Al composite solid base. (1) 7 g of 5,5-dimethylglycolide urea and 8.4 g of anhydrous sodium carbonate were added to a reaction vessel equipped with a spherical condenser tube, magnetically stirred, and reacted for 6 h at room temperature; (2) 1.05 g of lanthanum-modified nanoscale Ga/Al composite solid bases, 30 mL of ethyl acetate, and 30 mL of tetrahydrofuran were added sequentially to the mixture of step (1). Then 21 mL of liquid chlorine was added dropwise at a rate of 60 drops per minute, magnetic stirring was turned on, and the reaction was heated at 100 °C for 2 h. (3) The heated mixture from step (2) was transferred to a microwave reactor for 5 h. The mixture was then heated for 2 h. The mixture was then heated for 2 h. The reaction was then transferred to a microwave reactor for 5 h. After the reaction was completed, the mixture was cooled, filtration was performed, and the filter cake was washed with tetrahydrofuran. The filtrate was rotary evaporated to recover part of ethyl acetate, tetrahydrofuran and lanthanum-modified nanoscale Ga/Al composite solid bases; (4) the residual filtrate from step (3) was poured into pure water under continuous stirring to precipitate the product sufficiently, and pumped and filtered to obtain the crude product. The crude product was successively recrystallized with ethanol and pure water, and then recrystallized with toluene for the second time, and the target product 1,3-dichloro-5,5-dimethylimidazoline-2,4-dione was finally obtained. | [Environmental Fate]
Chemical/Physical. Reacts with water (pH 7.0) releasing hypochlorous acid. At pH 9, nitrogen
chloride is formed (Windholz et al., 1983). | [storage]
(1) Color Code—Yellow: Reactive Hazard; Storein a location separate from other materials, especially flammables and combustibles. (2) Color Code—White:Corrosive or Contact Hazard; Store separately in a corrosion-resistant location. Prior to working with this chemicalyou should be trained on its proper handling and storage.1,3-Dichloro-5,5-dimethyl-hydantoin must be stored toavoid contact with strong acids (such as sulfuric acid, nitricacid, or hydrochloric acid) and easily oxidized materials(such as ammonium salts and sulfides) since violent reactions occur and poisonous gases can be produced. Store intightly closed containers in a cool, well-ventilated area awayfrom water or steam. 1,3-Dichloro-5,5-dimethyl-hydantoindecomposes with formation of poisonous gases at201-210℃. If 1,3-dichloro-5,5-dimethyl-hydantoin contacts water or steam, it decomposes at lower temperaturesand produces poisonous gases, including chlorine. Sourcesof ignition, such as smoking and open flames, are prohibitedwhere 1,3-dichloro-5,5-dimethyl-hydantoin is used, handled,or stored in a manner that could create a potential fire orexplosion hazard. | [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.] | [Toxics Screening Level]
The initial threshold screening level (ITSL) for the following bromo- and chloro dimethylhydantoins is 2 μg/m3, based on an 8-hour averaging time. | [References]
[1] Patent: CN108484506, 2018, A. Location in patent: Paragraph 0016; 0018-0036
[2] Tetrahedron Letters, 2009, vol. 50, # 6, p. 656 - 658
[3] Journal fuer Praktische Chemie (Leipzig), 1926, vol. <2>113, p. 263 Anm.4 |
| Spectrum Detail | Back Directory | [Spectrum Detail]
1,3-Dichloro-5,5-dimethylhydantoin(118-52-5)MS
1,3-Dichloro-5,5-dimethylhydantoin(118-52-5)1HNMR
1,3-Dichloro-5,5-dimethylhydantoin(118-52-5)13CNMR
1,3-Dichloro-5,5-dimethylhydantoin(118-52-5)IR1
1,3-Dichloro-5,5-dimethylhydantoin(118-52-5)IR2
1,3-Dichloro-5,5-dimethylhydantoin(118-52-5)Raman
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