1,3-Dibromo-5,5-Dimethylhydantoin 1,3-二溴-5,5-二甲基海因

CAS 77-48-5 MFCD00003189

化学结构图

77-48-5
SMILES: CC1(C)C(=O)N(Br)C(=O)N1Br

化学属性

Mol. FormulaC5H6Br2N2O2
Mol. Weight285.92
Melting Point197-199°C
Density2.183
Flash Point155°(311°F)
TSCAYes
Stability对湿度敏感
Appearance 白色或淡黄色结晶粉末
Solubility>溶解性:微溶于水,溶于氯仿、乙醇等有机溶剂
Boiling Point250.2±23.0 °C at 760 mmHg

别名和识别编码

Chemical Name1,3-Dibromo-5,5-Dimethylhydantoin
CAS Number77-48-5
Alfabeta NameDIBROMODIMETHYLHYDANTOIN 1355---,,
MDL NumberMFCD00003189
Synonym 1,3-Dibromo-5,5-dimethylhydantoin {LY} 1,3-Dibromo-5,5-dimethylhydantoin {} {LY} 1,3-Dibromo-5,5-dimethylhydantoin {} {} {LY} 1,3-Dibromo-5,5-dimethylhydantoin {} {} {} {LY} 1,3-Dibromo-5,5-dimethylhydantoin {} {} {} {} { {} {} {} {} {LY} 1,3-Dibromo-5,5-dimethylhydantoin {} {} {} {} {} {LY} 1,3-Dibromo-5,5-dimethylhydantoin {} {} {} {} {} {} {LY} 1,3-Dibromo-5,5-dimethylhydantoin {} {} {} {} {} {} {} {LY} 1,3-Dibromo-5,5-dimethylhydantoin {} {} {} {} {} {} {} {} {LY} 1,3-Dibromo-5,5-dimethylhydantoin {} {} {} {} {} {} {} {} {} {LY} 1,3-Dibromo-5,5-dimethylhydantoin {} {} {} {} {} {} {} {} {} {} {LY} 1,3-Dibromo-5,5-dimethylhydantoin {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {LY} 1,3-Dibromo-5,5-dimethylhydantoin {} {} {} {} {} {} {} {} {} {} {} {} {LY} 1,3-Dibromo-5,5-dimethylhydantoin {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 1,3-Dibromo-5,5-dimethylhydantoin {} {} {} {} {} {} {} {} {} {} {}
EC Number201-030-9
Beilstein Registry Number146024
PubChem Substance ID6479
Chemical Name Translation1,3-二溴-5,5-二甲基海因
Merck Number3017
Reaxys-RN146024
InChIKeyVRLDVERQJMEPIF-UHFFFAOYSA-N
Wiswesser Line NotationT5NVNV EHJ AE CE E1 E1
LabNetwork Molecule IDLN00173784
InChIInChI=1S/C5H6Br2N2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3
Canonical SMILESO=C1N(Br)C(C(C)(C)N1Br)=O
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分类

  • {SNA} Bromination, C-X Bond Formation (Halogen), Chemical Synthesis, Synthetic Reagents

产品应用

  • 用于烷氧基苯甲酸的芳香溴化以及烯烃的溴氟化。

相关文献及参考

  • Free-radical brominating agent: J. Chem. Soc., 4678 (1962), alternative to N-Bromosuccinimide, A15922, in many large-scale brominations. Superior to NBS for the regioselective free-radical 2-bromination of pyrrole: J. Org. Chem., 46, 2221 (1981); Org. Synth. Coll., 9, 121 (1998).
  • Also behaves as a source of positive bromine. Electron-rich aromatic compounds undergo uncatalyzed ring-bromination: Tetrahedron Lett., 38, 4415 (1997). The bromination of less active substrates can be catalyzed by TMS triflate. Bromination of aromatic rings, including those with electron-withdrawing substituents, also occurs in the presence of strong acids: Bull. Chem. Soc. Jpn., 67, 1918 (1994). Has also been used as an alternative to NBS for the ring bromination of activated benzoic acids in the presence of aqueous NaOH: Tetrahedron Lett., 34, 931 (1993).
  • For use in combination with AgF as a reagent for the trans-fluorobromination of alkenes, see: Chem. Lett., 1877 (1988).

安全信息

Warnings MOISTURE SENSITIVE, CORROSIVE, OXIDIZER
Signal word Danger
GHS Symbol
WGK Germany3
Safety Statements
  • S17 Keep away from combustible material 远离可燃物料;
  • S20 When using do not eat or drink 使用时,不得进食,饮水;
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时,立即求医(可能时出示标签);
  • S57 Use appropriate containment to avoid environmental contamination 使用适当容器避免环境污染;
  • S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置;
  • S61 Avoid release to the environment. Refer to special instructions/safety data sheet 避免释放到环境中,参考特别指示/安全收据说明书;
Risk Statements
  • R22 Harmful if swallowed 吞咽有害
  • R34 Causes burns 会导致灼伤
  • R35 Causes severe burns 会导致严重灼伤
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R50 Very toxic to aquatic organisms 对水生生物极毒
  • R50/53
  • R8 Contact with combustible material may cause fire 遇到易燃物会导致起火
Precautionary statements
  • P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking. 远离热源/火花/明火/热的表面。——禁止吸烟。
  • P220 Keep/Store away from clothing/…/combustible materials. 保持远离/贮存远离服装/....../可燃材料。
  • P221 Take any precaution to avoid mixing with combustibles/… 采取一切防范措施,避免与可燃物混合/...
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
  • P272 Contaminated work clothing should not be allowed out of the workplace. 污染的工作服不得带出工作场所。
  • P273 Avoid release to the environment. 避免释放到环境中。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P301+P310
  • P301+P312
  • P301+P330+P331
  • P301+P330+P331+P310
  • P302+P352
  • P303+P361+P353
  • P303+P361+P353+P310+P363
  • P304+P340
  • P304+P340+P310
  • P305+P351+P338
  • P305+P351+P338+P310
  • P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或医生/医师。
  • P321 Specific treatment (see … on this label). 具体治疗(见本标签上的)。
  • P330 Rinse mouth. 漱口
  • P332+P313
  • P333+P313
  • P337+P313
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服,清洗后方可重新使用
  • P363 Wash contaminated clothing before reuse. 被污染的衣服洗净后方可重新使用。
  • P370+P378
  • P391 Collect spillage. Hazardous to the aquatic environment 收集对水环境有危害的泄漏物。
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H272 May intensify fire; oxidizer 可能加剧火势;氧化剂。
  • H301 Toxic if swallowed 吞食有毒
  • H302 Harmful if swallowed 吞食有害
  • H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
  • H315 Causes skin irritation 会刺激皮肤
  • H317 May cause an allergic skin reaction 可能导致皮肤过敏
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H400 Verytoxictoaquaticlife 对水生生物毒性非常大。
  • H410 Verytoxictoaquaticlifewithlonglastingeffects 对水生生物毒性非常大并具有长期影响。
Personal Protective Equipment Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
RTECSMU0686000
Packing GroupII
UN Number 3087 UN3085
Storage condition 2-8°C {LY} 2-8°C Moisture Sensitive {} {LY} 2-8°C {} {} {LY} 2-8°C {} {} {} {LY} 2-8°C {} {} {} {} {LY} 2-8°C {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {
Hazard Codes 5.1 O,C,N
Hazard Class5.1/6.1
TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Administration onto the skin
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : 20 gm/kg
TOXIC EFFECTS :
   Sense Organs and Special Senses (Olfaction) - effect, not otherwise
   specified
   Behavioral - somnolence (general depressed activity)
   Skin and Appendages - hair
REFERENCE :
   EPASR* United States Environmental Protection Agency, Office of Pesticides
   and Toxic Substances. (U.S. Environmental Protection Agency, 401 M St., SW,
   Washington, DC 20460)  History unknown.  Volume(issue)/page/year:
   8EHQ-0581-0382

TYPE OF TEST            : LCLo - Lowest published lethal concentration
ROUTE OF EXPOSURE       : Inhalation
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 29 gm/m3/1H
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   EPASR* United States Environmental Protection Agency, Office of Pesticides
   and Toxic Substances. (U.S. Environmental Protection Agency, 401 M St., SW,
   Washington, DC 20460)  History unknown.  Volume(issue)/page/year:
   8EHQ-0281-0382

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 250 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   GISAAA Gigiena i Sanitariya.  For English translation, see HYSAAV.  (V/O
   Mezhdunarodnaya Kniga, 113095 Moscow, USSR)  V.1-    1936-
   Volume(issue)/page/year: 36(10),108,1971

其他信息

  • 图谱信息:1,3-二溴-5,5-二甲基海因(77-48-5)质谱(MS) 1,3-二溴-5,5-二甲基海因(77-48-5)红外图谱(IR1) 1,3-二溴-5,5-二甲基海因(77-48-5)红外图谱(IR2)
  • 二溴海因价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 D1265 1,3-二溴-5,5-二甲基乙内酰脲 1,3-Dibromo-5,5-dimethylhydantoin 500G 604元 2014/06/02 D1265 1,3-二溴-5,5-二甲基乙内酰脲 1,3-Dibromo-5,5-dimethylhydantoin 25G 150元 2010/06/21 169540250 1,3-二溴-5,5-二甲基海因 1,3-Dibromo-5,5-dimethylhydantoin 98% 25 GR 212元
  • 理化性质:二溴海因英文简称DBDMH,纯品为白色固体,熔点196~198℃,工业品为淡黄色固体,熔点194~197℃;溶于氯仿、乙醇、丙酮等有机溶剂,微溶于水,20℃时1L水溶解2.2g二溴海因,0.1%水溶液的pH值为2.6;在强酸或强碱中易分解;干燥时稳定,容易吸潮,吸潮后部分水解;有轻微刺激性气味;活性溴含量为54%~55%。
  • 类别:农药
  • MSDS 信息:1,3-Dibromo-5,5-dimethyl-2,4-imidazolidinedione(77-48-5).msds
  • 杀菌作用机理:二溴海因在水中水解主要形成次溴酸,以次溴酸的形式释放出溴。二溴海因释放溴的反应很快,在水中能够不断地释放出Br-离子,起到杀菌效果。而其他卤化海因,如二氯海因或溴氯海因释放氯的反应很慢,在水中形成杀菌高峰的时间要相对滞后,所以二溴海因在需要相对快速杀菌的条件下拥有比其他卤化海因更高的效率。
  • 工业用溴化剂和杀菌消毒剂:二溴海因主要作为工业用溴化剂和杀菌消毒剂。它是十分有用的溴化剂,与N-溴代乙酰胺、N-溴代丁二酰亚胺等溴化剂相比具有活性溴含量高、贮存稳定性好、使用经济等优点,广泛用于化工、制药工业中的烯丙基及苄基化合物和活性芳环上的溴化,双键上的溴或溴化氢加成以及仲醇的选择性氧化反应;另外,二溴海因也是一种高效、安全的杀菌消毒剂,具有强烈杀灭真菌、细菌及病毒的效果,且有杀灭水体不良藻
  • 应用领域:二溴海因是一种重要的化工产品,应用于化工、医药和农业等行业,具有稳定性好、含溴量高和反应活性高等优点。目前,关于二溴海因和其他卤代海因之间加以复配后应用,已成为近年来的研究热点,如溴氯海因与二溴海因的复合应用、二氯海因与二溴海因的复合应用等。二溴海因与其他卤化海因复配时有效溴与有效氯的比值是至关重要的因素,在pH为7.1 的条件下,投加相同剂量的溴氯海因与二溴海因的复合制剂,其杀生效率明显高于单独使用二溴海因或溴氯海因。国内外许多专家认为在氧化型杀菌剂中最有意义的是溴氯海因和二溴海因配伍后的复合卤化海因。在农业中,二
  • 可燃性危险特性:可燃, 火场排出氮氧化物和溴化物辛辣刺激烟雾
  • Sigma Aldrich:77-48-5(sigmaaldrich)
  • 用途二:用作工业溴化剂和消毒杀菌剂
  • Acros Organics:1,3-二溴-5,5-二甲基海因 1,3-Dibromo-5,5-dimethylhydantoin, 98%(77-48-5)
  • Alfa Aesar:1,3-二溴-5,5-二甲基乙内酰脲,98% 1,3-Dibromo-5,5-dimethylhydantoin, 98%(77-48-5)
  • Hazard Note:Harmful/Irritant
  • 灭火剂:水, 二氧化碳, 干粉, 砂土
  • 下游产品:1-氟-4-(三氟甲基硫代)苯 --> 5-溴-2-(二甲基氨基)嘧啶
  • 海关编码:29332100
  • Decomposition:197-199 °C
  • 急性毒性:口服-大鼠 LD50: 250 毫克/公斤
  • 用途三:有机合成中间体。

系列性分类


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