1,4-Diazabicyclo[2.2.2]octane 三乙烯二胺

CAS 280-57-9 MFCD00006689

化学结构图

280-57-9
SMILES: C1CN2CCN1CC2

化学属性

Mol. FormulaC6H12N2
Mol. Weight112.17
Density1.02
Flash Point62°C
TSCAYes
Boiling Point174°C at 760 mmHg
Melting Point156-159°C
SolubilitySoluble in water (460 mg/ml)
Refractive indexn20/D 1.4634(lit.)
Vapor Pressure2.9 mmHg ( 50 °C)
Appearance 无水物为可燃性白色结晶体,极易潮解。 能溶于水、乙醇、丙酮和苯。25℃时在水中的溶解度为45g/100g,在乙醇中的溶解度为77g/100g,在丙酮中的溶解度为13g/100g,在苯中的溶解度为51g/100g。
Stability易吸潮

别名和识别编码

Chemical Name1,4-Diazabicyclo[2.2.2]octane
Synonym 1,4-Diazabicyclo[2.2.2]octane {LY} 1,4-Diazabicyclo[2.2.2]octane 1,4-diazabicyclo(2.2.2)octane 1,4-diazabicyclo-octane DABCO DABCO cpd triethylenediamine triethylenediamine diacetate {} {LY} 1,4-Diazabicyclo[2.2.2]octane {} {} {LY} 1,4-Diazabicyclo[2.2.2]octane {} {} {} {LY} 1,4-Diazabicyclo[2.2.2]octane {} {} {} {} {LY} 1,4-Diazabicyclo[2.2.2]octane {} {} {} {} {} {LY} 1,4-Diazabicyclo[2.2.2]octane {} {} {} {} {} {} {LY} 1,4-Diazabicyclo[2.2.2]octane {} {} {} {} {} {} {} {LY} 1,4-Diazabicyclo[2.2.2]octane {} {} {} {} {} {} {} {} {LY} 1,4-Diazabicyclo[2.2.2]octane {} {} {} {} {} {} {} {} {} {LY} 1,4-Diazabicyclo[2.2.2]octane {} {} {} {} {} {} {} {} {} {} {LY} 1,4-Diazabicyclo[2.2.2]octane {} {} {} {} {} {} {} {} {} {} {} {LY} 1,4-Diazabicyclo[2.2.2]octane {} {} {} {} {} {} {} {} {} {} {} {} {LY} 1,4-Diazabicyclo[2.2.2]octane {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
MDL NumberMFCD00006689
CAS Number280-57-9
EC Number205-999-9
Beilstein Registry Number103618
PubChem Substance ID9237
Reaxys-RN103618
Merck Number9669
Chemical Name Translation三乙烯二胺
LabNetwork Molecule IDLN00005644
InChIInChI=1S/C6H12N2/c1-2-8-5-3-7(1)4-6-8/h1-6H2
Canonical SMILESN1(CC2)CCN2CC1
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分类

  • {SNA} Acids & Bases, Amine Monomers, Bases, Chemical Biology, Chemical Synthesis, Conjugation Chemistry: Azides, Alkynes and Other Reagents, Materials Science, Monomers, Organic Bases, Polymer Science, Staudinger Ligation, Synthetic Reagents, Tertiary Amines
  • {SNA} Acids & Bases, Amine Monomers, Bases, Chemical Biology, Chemical Synthesis, Conjugation Chemistry: Azides, Alkynes and Other Reagents, Monomers, Organic Bases, Polymer Science, Staudinger Ligation, Synthetic Reagents, Tertiary Amines,
  • {SNA} Acids & Bases,

产品应用

  • An anti-fade reagent shown to scavenge free-radicals due to flurochrome excitation.

相关文献及参考

  • Short: II/25D
  • Merck: 14,9669
  • Merck: 14,9669 Beilstein: 23,V,3,487
  • In conjunction with palladium acetate and PEG-400 provides a reusable catalyst system for the Suzuki-Miyaura cross-coupling reaction of boronic acids: J. Org. Chem., 70, 5409 (2005).
  • Forms a stable crystalline complex with H2O2, useful as an equivalent to "anhydrous" H2O2: reaction with TMS chloride gives bis(TMS) peroxide, a useful OH+-equivalent, e.g. in the conversion of aryllithiums to phenols: Synthesis, 633 (1986).
  • Forms crystalline complexes with organolithium compounds: J. Am. Chem. Soc., 87, 3276 (1965), which show enhanced reactivity, e.g. in the high yield ɑ-metallation of thioanisole by n-BuLi: J. Org. Chem., 31, 4097 (1966).
  • Dabco is a registered trademark of Air Products and Chemicals Inc.
  • For further illustrative example, see: Org. Synth., 75, 106 (1997). Complete reaction often takes several days at ambient temperature, while heating causes lower yields. However, it is greatly accelerated by microwave irradiation: Synlett, 444 (1994). Superior results with reduced reaction times can be achieved in aqueous medium: J. Org. Chem., 66, 5413 (2001). The use as reaction medium of tetramethylene sulfone: Tetrahedron Lett., 45, 1183 (2004), or PEG-400: Tetrahedron Lett., 45, 5865 (2004) has also been advocated. Lithium perchlorate was found to increase the reaction rate dramatically: Tetrahedron Lett., 40, 1539 (1999), as was a catalytic amount of a metal triflate, particularly La or Sm; conventional Lewis acids were ineffective: J. Org Chem., 63, 7183 (1998). For asymmetric Baylis-Hillman reaction using (1S,2R)-(-)-10,2-Camphorsultam, A15897, as chiral auxiliary, see: J. Am. Chem. Soc., 119. 4317 (1997). See also 3-Quinuclidinol, B21503. For more recent discussion and comparison of different catalysts, see: J. Org. Chem., 692 (2003). In a reinterpretaion of the mechanism, a hemiacetal interemediate has been proposed: J.
  • {uni_ha

安全信息

Signal word Danger
GHS Symbol
WGK Germany1
Safety Statements
  • S16 Keep away from sources of ignition - No smoking 远离火源,禁止吸烟;
  • 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;
  • S3 Keep in a cool place 保存在阴凉处;
  • 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;
  • S37/39 Wear suitable gloves and eye/face protection 穿戴适当的手套和眼睛/面保护;
  • 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
  • R11 Highly flammable 非常易燃
  • R22 Harmful if swallowed 吞咽有害
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R52/53
Precautionary statements
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前,切勿操作。
  • P203
  • 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。
  • P240 Ground/bond container and receiving equipment. 与地面接触/连接集装箱和接受设备。
  • P241 Use explosion-proof electrical/ventilating/lighting/…/equipment. 使用防爆电气/通风/照明/ .../设备。
  • 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。
  • P264+P265
  • 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。
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • 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。
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • P301+P312
  • P301+P317
  • P301+P330+P331+P310
  • P302+P352
  • P303+P361+P353+P310+P363
  • P304+P340
  • P304+P340+P310
  • P305+P351+P338
  • P305+P351+P338+P310
  • P305+P354+P338
  • P308+P313
  • P308+P316
  • P309+P311
  • P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或医生/医师。
  • P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感觉不适,呼叫解毒中心或医生/医师。
  • P314 Get medical advice/attention if you feel unwell. 获取医疗咨询/就医,如果你觉得不舒服
  • P317
  • P318
  • P319
  • P321 Specific treatment (see … on this label). 具体治疗(见本标签上的)。
  • P330 Rinse mouth. 漱口
  • P332+P313
  • P332+P317
  • P337+P313
  • P337+P317
  • 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
  • P362+P364
  • P370+P378
  • P403+P233
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H228 Flammable solid 易燃固体
  • H302 Harmful if swallowed 吞食有害
  • H315 Causes skin irritation 会刺激皮肤
  • H318 Causes serious eye damage 严重伤害眼睛
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H412 Harmfutoaquaticlifewithlonglastingeffects 对水生生物有害并具有长期影响。
Hazard Codes 4.1 F,Xn
Personal Protective Equipment Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
RTECSHM0354200
UN Number 1325 3263 UN1325
Storage condition 2-8°C, protect from light, stored under nitrogen {LY} 2-8°C, protect from light, stored under nitrogen Hygroscopic {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light
Packing GroupII
Hazard Class8
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - guinea pig
DOSE/DURATION           : 2250 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Behavioral - muscle weakness
   Behavioral - muscle contraction or spasticity
REFERENCE :
   GISAAA Gigiena i Sanitariya.  For English translation, see HYSAAV.  (V/O
   Mezhdunarodnaya Kniga, 113095 Moscow, USSR)  V.1-    1936-
   Volume(issue)/page/year: 45(5),67,1980

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 1700 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   ZHYGAM Zeitschrift fuer die Gesamte Hygiene und Ihre Grenzgebiete.  (VEB
   Verlag Volk und Gesundheit, Neue Gruenstr. 18, Berlin DDR-1020, Ger. Dem.
   Rep.)  V.1-    1955-  Volume(issue)/page/year: 20,393,1974

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : 1100 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Behavioral - muscle weakness
   Behavioral - muscle contraction or spasticity
REFERENCE :
   GISAAA Gigiena i Sanitariya.  For English translation, see HYSAAV.  (V/O
   Mezhdunarodnaya Kniga, 113095 Moscow, USSR)  V.1-    1936-
   Volume(issue)/page/year: 45(5),67,1980

其他信息

  • 易溶于水,水中溶解度: 46 g/100ml (26 C), 溶于丙酮、苯及乙醇等常规有机溶剂,溶于戊烷、已烷、庚烷等直链烃类;暴露在空气中易吸湿潮解并结块,能吸收空气中的CO2 并发黄。
  • 用途三:主要用作聚氨酯发泡(硬泡、软泡)催化剂。可以直接使用,也可以配成A―33后使用。还有用作农药生产的引发剂(如六氨吡啶的引发剂),以及无氰电镀添加剂。该产品呈强碱性、低毒,有刺激性,使用时应穿戴防护用品。
  • 方法一:将1,2-二氯乙烷和氨水送入管式反应器中,于150-250℃、392kPa压力下进和热压氨化反应。反应液以碱中和得到混合游离胺,经浓缩除去氯化钠,然后将粗吕减压蒸馏,收集不同馏分进行分离。在获得该品同时,并联产乙二胺、二亚乙基三胺、三亚乙基四胺、四亚乙基五胺和多亚乙基多胺。从生产六水哌嗪的母液中经分馏可得该品,第生产100t六水哌嗪可得六水三亚乙基二胺约3-4t。
  • 三乙烯二胺价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 30184062 三乙烯二胺 250g 79.6元 2011/04/16 D0134 1,4-二氮杂二环[2.2.2]辛烷 1,4-Diazabicyclo[2.2.2]octane 25G 190元 2011/04/16 D0134 1,4-二氮杂二环[2.2.2]辛烷 1,4-Diazabicyclo[2.2.2]octane 500G 1320元
  • MSDS 信息:1,4-Diazabicyclo[2.2.2]octane(280-57-9).msds
  • TCI Shanghai:1,4-二氮杂二环[2.2.2]辛烷 1,4-Diazabicyclo[2.2.2]octane,>;98.0%(T)(280-57-9)
  • MOL 文件:280-57-9.mol
  • 上游原料:乙二胺 --> 氯乙烷 --> 二乙烯三胺 --> 哌嗪(六水) --> 三乙烯四胺 --> 多乙烯多胺 --> 四亚乙基五胺
  • 用途二:用于制取聚氨酯类泡沫塑料的催化剂和石油添加剂。
  • Alfa Aesar:1,4-二偶氮双环[2.2.2]辛烷,98% 1,4-Diazabicyclo[2.2.2]octane, 98%(280-57-9)
  • 下游产品:双二苯基磷酰联萘 --> 5-溴嘧啶-2-羧酸 --> 苯磺隆 --> 1,1'-联萘-2,2'-双二苯膦 --> 双二苯基磷酰联萘 --> 脱氢乙酸 --> S-(-)-1,1'-联萘-2,2'-双二苯膦 --> R-(+)-1,1'-联萘-2,2'-双二苯膦 --> 2-溴甲基丙烯酸乙酯 --> 2-氯-3-氟异烟酸 --> 3-氟吡啶-2-羧酸 --> 5-溴-2-氰基嘧啶
  • Sigma Aldrich:280-57-9(sigmaaldrich)
  • 蒸气压:2.9 mm Hg ( 50 °C)
  • F:3
  • Acros Organics:1,4-二叠氮双环[2.2.2]辛烷/三乙烯二胺 1,4-Diazabicyclo[2.2.2]octane, 97%(280-57-9)
  • 用途一:可用于聚氨酯泡沫体、弹性体及涂料等多种制品的生产
  • 海关编码:29335920
  • 敏感性:Hygroscopic

系列性分类


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