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1,3-ジブロモ-5,5-ジメチルヒダントイン

1,3-Dibromo-5,5-dimethylhydantoin

HCID 6479
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
77-48-5
標準SMILES
CC1(C)C(=O)N(Br)C(=O)N1Br
InChIKey
VRLDVERQJMEPIF-UHFFFAOYSA-N
分子式
C5H6Br2N2O2
平均分子量
285.92 g/mol
単同位体質量
283.87960163

概要

1,3-Dibromo-5,5-dimethylhydantoin is an organobromide compound derived from the heterocycle called dimethylhydantoin. It is widely used as a disinfectant used for drinking water purification, recreational water treatment, as a bleaching agent in pulp and paper mills, and for treating industrial/commercial water cooling systems. Bromine is a halogen element with the symbol Br and atomic number 35. Diatomic bromine does not occur naturally, but bromine salts can be found in crustal rock. (L625, L690)

名称と識別子

優先名称
1,3-Dibromo-5,5-dimethylhydantoin
IUPAC
1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione
現地名
1,3-ジブロモ-5,5-ジメチルヒダントイン
英語名
1,3-Dibromo-5,5-dimethylhydantoin
分子式
C5H6Br2N2O2
分子量
285.92

名称と別名

1,3-Dibromo-5,5-dimethylhydantoin77-48-5Dibromantin1,3-dibromo-5,5-dimethylimidazolidine-2,4-dioneDibromantineTake Charge OrangeDBDMHN,N'-Dibromodimethylhydantoin1,3-Dibromo-5,5-dimethyl-2,4-imidazolidinedione5,5-Dimethyl-1,3-dibromohydantoin2,4-Imidazolidinedione, 1,3-dibromo-5,5-dimethyl-DTXSID3035341
名称をさらに表示
1,3-ジブロモ-5,5-ジメチルヒダントイン1,3-ジブロモ-4,4-ジメチルイミダゾリジン-2,5-ジオン1,3-ジブロモジメチルヒダントインジブロマンチン1,3-ジブロモ-5,5-ジメチル-1H-イミダゾール-2,4-ジオン1,3-ジブロモ-5,5-ジメチルイミダゾリジン-2,4-ジオン1,3-ジブロモ-5,5-ジメチル-2,4-イミダゾリジンジオン1,3ジブロモ5,5ジメチルヒダントイン1,3‐ジブロモ‐5,5‐ジメチルヒダントイン1,3-ジブロモ-5,5-ジメトルヒダントインジブロモジメチルヒダントイン1,3-ジブロモ-5,5-ジメチル-1H-イミダゾール-2(3H),4(5H)-ジオン1,3-ジブロモ-4,4-ジメチルヒダントイン1,3-ジブロモ-4,4-ジメチル-2,5-イミダゾリジンジオンDBNPADDHdibromohydantoinHSC

物性

構造計算による物性

XLogP
1.5
極性表面積
40.6 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
0
重原子数
11
形式電荷
0
複雑度
229

実験および物理化学的性質

Chemical ClassesOther Uses -> Biocides/Disinfectants
Food Contact Substances · 2 件

FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications

FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications

Physical Description · 2 件

Dry Powder

Light yellow powder; [Aldrich MSDS]

物理化学的性質

融点
197 · 197-199 °C (dec.)(lit.)
沸点
250.2 · 250.2±23.0 °C(Predicted)
比重(密度)
1 g/cm3 · 1.00 g/cm3 (25℃)
屈折率
1.622 · 1.6220 (estimate)
闪点
155 °C · 155 °C
貯蔵温度
30 °C · Store below +30°C.
溶解性
1 g/リットル · 1g/リットル
外見
粉
酸解離定数(Pka)
-3.44 · -3.44±0.40(Predicted)
色
クリーム色または淡い黄色
水溶解度
アルコール、エーテル、ベンゼンに可溶。水に不溶。

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Danger

H272 (93.5%): May intensify fire; oxidizer [Danger Oxidizing liquids; Oxidizing solids]

P210, P220, P260, P264, P264+P265, P270, P273, P280, P301+P316, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P321, P330, P332+P317, P337+P317, P362+P364, P363, P370+P378, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 231 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 4 件

Chemical: 2,4-Imidazolidinedione, 1,3-dibromo-5,5-dimethyl-

2,4-Imidazolidinedione, 1,3-dibromo-5,5-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2,4-Imidazolidinedione, 1,3-dibromo-5,5-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 24-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/10089

1,3-Dibromo-5,5-dimethylhydantoin: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 件

Evidence of thyroid hypofunction in repeated dose study of rats; [RTECS] Corrosive to skin; Not sensitizing to guinea pigs; Halohydantoins: The persistent metabolites, 5,5-Dimethylhydantoin (DMH) and 5-Ethyl-5-methylhydantoin (EMH), are used for developing toxicity data for this group of compounds; Quickly decomposed by water forming hypochlorous or hypobromous acid (the true biocidal agents) and DMH or EMH; DMH/EMH: Sub-chronic, developmental, reproductive, and chronic toxicity animal studies have shown non-specific toxicity at high doses (no evidence of carcinogenicity, reproductive or developmental toxicity, and limited evidence of mutagenicity); [Reference #1] An oxidizer that can intensify fire; Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Toxic by ingestion; [Aldrich MSDS] See 1,3-Dichloro-5,5-dimethylhydantoin.

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

Bromine is mainly absorbed via inhalation, but may also enter the body through dermal contact. Bromine salts can be ingested. Due to its reactivity, bromine quickly forms bromide and may be deposited in the tissues, displacing other halogens. (L626)

用途と製造

Uses · 3 件

Halohydantoins: Used as disinfectants in swimming pools, hot tubs, toilet bowls, and industrial systems (cooling water, pulp and paper, wastewater, and sewage); Also used as slimicide for paper/paperboard for food contact; [Reference #1]

Pulp and Paper Processing [Category: Industry]

1,3-Dibromo-5,5-dimethylhydantoin is an organobromide compound derived from the heterocycle called dimethylhydantoin. It is widely used as a disinfectant used for drinking water purification, recreational water treatment, as a bleaching agent in pulp and paper mills, and for treating industrial/commercial water cooling systems. Diatomic bromine does not occur naturally, but bromine salts can be found in crustal rock.

U.S. Production2023: <75,000 lb
Industry UsesIntermediate
General Manufacturing Information · 2 件

Photographic Film, Paper, Plate, and Chemical Manufacturing

2,4-Imidazolidinedione, 1,3-dibromo-5,5-dimethyl-: ACTIVE

応用分野 · 4 件

用途有機合成用試薬。

説明1,3-Dibromo-5,5-dimethylhydantoin is an important chemical product and has been widely applied in chemical, pharmaceutical and agricultural industries with various kinds of advantages including excellent stability, high content of bromine and high reactive activity.

使用Brominating agent. Analytical reagent for determination of iodide and organic iodine, and for identification tests.

関連反応

408 件
反応記録を作成
HRID 5774 の反応式
HRID 5774反応物としてuspto-grants-1993_09
HRID 6465 の反応式
HRID 6465反応物としてuspto-grants-1993_09
HRID 6466 の反応式
HRID 6466反応物としてuspto-grants-1993_09
HRID 37516 の反応式
HRID 37516反応物としてuspto-grants-1995_05
HRID 59580 の反応式
HRID 59580反応物としてuspto-grants-2016_09
HRID 60222 の反応式
HRID 60222反応物としてuspto-grants-2016_09
HRID 60230 の反応式
HRID 60230反応物としてuspto-grants-2016_09
HRID 60392 の反応式
HRID 60392反応物としてuspto-grants-2016_09
1 / 51 ページ

化合物ノート

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その他の操作
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DIBROMATIN
V9R5F9I7MZHYDANTOIN, 1,3-DIBROMO-5,5-DIMETHYL-NSC-33305DTXCID1015341DisinfectantTabletsDisinfectant TabletsRefChem:536271,3-dibromo 5,5-dimethylhydantoin

データベース識別子

CAS
77-48-5
PubChem CID
6479
DTXSID
DTXSID3035341
ChEMBL
CHEMBL3184055
UNII
V9R5F9I7MZ
EC Number
201-030-9
Nikkaji
J25.319G
Decomposition
197 · 197-199 ºC
Merck
14 · 14,3017
BRN
146024 · 146024
InChI
1S/C5H6Br2N2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3
InChIKey
VRLDVERQJMEPIF-UHFFFAOYSA-N
SMILES
CC1(C)N(Br)C(=O)N(Br)C1=O
CAS データベース
77 · 77-48-5(CAS DataBase Reference)
EPAの化学物質情報
1 · 1,3-Dibromo-5,5-dimethylhydantoin (77-48-5)

化学的性質

化学的特性solid

Hazard Classes and CategoriesOx. Sol. 3 (93.5%)

毒性情報

Treatment · 1 件

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Health Effects · 1 件

Bromine vapour causes irritation and direct damage to the mucous membranes. Elemental bromine also burns the skin. The bromide ion is a central nervous system depressant and chronic exposure produces neuronal effects. This is called bromism and can result in central reactions reaching from somnolence to coma, cachexia, exicosis, loss of reflexes or pathologic reflexes, clonic seizures, tremor, ataxia, loss of neural sensitivity, paresis, papillar edema of the eyes, abnormal speech, cerebral edema, delirium, aggressiveness, and psychoses. (L625, L626, L627)

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesOral (L626) ; inhalation (L626) ; dermal (L626)
Toxicity Summary · 1 件

Bromine is a powerful oxidizing agent and is able to release oxygen free radicals from the water in mucous membranes. These free radicals are also potent oxidizers and produce tissue damage. In additon, the formation of hydrobromic and bromic acids will result in secondary irritation. The bromide ion is also known to affect the central nervous system, causing bromism. This is believed to be a result of bromide ions substituting for chloride ions in the in actions of neurotransmitters and transport systems, thus affecting numerous synaptic processes. (L626, L627, A543)

Signs and Symptoms · 1 件

Bromine vapour causes irritation and direct damage to the mucous membranes. Symptoms include lacrimation, rhinorrhoea, eye irritation with mucous secretions from the oropharyngeal and upper airways, coughing, dyspnoea, choking, wheezing, epistaxis, and headache. The bromide ion is a central nervous system depressant producing ataxia, slurred speech, tremor, nausea, vomiting, lethargy, dizziness, visual disturbances, unsteadiness, headaches, impaired memory and concentration, disorientation and hallucinations. This is called bromism. (L626, L627)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Toxicity DataLC50 (rat) = 510 - 2,020 mg/m3

安全データ

wgk
3
tsca
TSCA listed
rtecs
MU0686000
ridadr
UN 3087 5.1/PG 2
hs_code
29332100
risk_code
8-22-35-50/53-50-34
化審法
(9)-627
hazard_code
O,C,N,Xi
hazard_note
Harmful/Irritant
safety_code
17-26-36/37/39-45-60-61
hazard_class
5.1
packing_group
II
自然発火温度
550°C
Hazard Classifications
Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Ox. Sol. 3Skin Corr. 1BSkin Sens. 1
ストレージクラス
5.1B - Oxidizing hazardous materials

一般的な説明Currently, the combined formulation between 1,3-Dibromo-5,5-dimethylhydantoin(DBDMH) and other halogenated hydantoin for application has become a hotspot in recent years such as the combined application of BCDMH and DBDMH as well as the combined application of DCDMH and DBDMH. For the combined formulation of DBDMH and other halogenated hydantoin, one critical factor is the ratio between effective chlorine and effective bromine.

調製方法

純化方法Recrystallise it from H2O. Its solubility in CCl4 is 0.003 mol/L at 25o and 0.024 mol/L at 76.5o. [Beilstein 24 III/IV 1101.]

上流・下流製品情報

上流原料

次亜塩素酸ナトリウム5,5-ジメチルヒダントイン塩酸1,3-ジクロロ-5,5-ジメチルヒダントインシアン化ナトリウム水酸化ナトリウム

下流製品

1-フルオロ-4-(トリフルオロメチルチオ)ベンゼン5-ブロモ-2-(ジメチルアミノ)ピリミジン 臭化物1,6-ジブロモピレン1-(ブロモメチル)-3-フェノキシベンゼン