1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) 1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)

CAS 6674-22-2 MFCD00006930

化学结构图

6674-22-2
SMILES: C1CCC2=NCCCN2CC1

化学属性

Mol. FormulaC9H16N2
Mol. Weight152.24
Density0.908
Refractive index1.5200 to 1.5240
Boiling Point274.6°C at 760 mmHg
Flash Point116°C
TSCAT
Melting Point-70°C
Vapor Pressure5.3 mmHg ( 37.7 °C)
Solubility可溶
Stability对空气敏感
Appearance 无色或微黄色油状液体。
Danger-Level乙类

别名和识别编码

Chemical Name1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)
CAS Number6674-22-2
Alfabeta NameDIAZABICYCLOUNDECENE 185407..[]---,
MDL NumberMFCD00006930
EC Number205-500-4
Beilstein Registry Number508906
Synonym DBU {LY} DBU {} {LY} DBU {} {} {LY} DBU {} {} {} {LY} DBU {} {} {} {} {LY} DBU {} {} {} {} {} {LY} DBU {} {} {} {} {} {} {LY} DBU {} {} {} {} {} {} {} {LY} DBU {} {} {} {} {} {} {} {} {LY} DBU {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} DBU {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} DBU {} {} {} {} {} {} {} {} {} {} {} {LY} DBU {} {} {} {} {} {} {} {} {} {} {} {} {LY} DBU {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} DBU {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} DBU {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} DBU {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} DBU {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} DBU {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} DBU {} {} {} {} {} {} {} {} {} {} {} {}
PubChem Substance ID81184
Chemical Name Translation1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)
Reaxys-RN508906
LabNetwork Molecule IDLN00174463
InChIInChI=1S/C9H16N2/c1-2-5-9-10-6-4-8-11(9)7-3-1/h1-8H2
Canonical SMILESN12C(CCCCC2)=NCCC1
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分类

  • {SNA} Chemical Synthesis, Organic Bases, Synthetic Reagents
  • {SNA} Acids & Bases, Bases, Chemical Reagents, Chemical Synthesis, Development Quantities for Research, Organic Bases, Synthetic Reagents
  • {SNA} Chemical Reagents, Acids & Bases, Bases, Chemical Synthesis, Development Quantities for Research, Organic Bases, Synthetic Reagents
  • {SNA} Acids & Bases, Bases, Chemical Synthesis, Organic Bases, Synthetic Reagents

产品应用

  • 用于聚氨基甲醇乙酯及其他化学制品生产的催化剂，如氨和二氯乙烷在它的存在下反应生成哌嗪，是一种优良的脱水剂，环氧树脂硬化剂，防锈剂，还可配制高级缓蚀剂。当前广泛用于头孢半合成抗生素药的生产。还用于有机合成反应和半合成抗菌素。

相关文献及参考

  • Merck: 14,10412 Beilstein: 23,V,5,271
  • For a review of the chemistry of DBU and other pyrimidoazepines, see: Adv. Heterocycl. Chem., 42, 84 (1987).
  • In combination with NBS in MeOH, promotes the Hofmann rearrangement of amides to give methyl carbamates under mild conditions: J. Org. Chem., 62, 7495 (1997).
  • DBU forms hydrogen-bonded complexes with carboxylic acids, which can be alkylated in good yield by alkyl bromides or iodides, in a simple esterification procedure: Bull. Chem. Soc. Jpn., 51, 2401 (1978).
  • Used in the Wittig reaction to generate ylides stabilized by aryl or electron-withdrawing groups, see: Chem. Ber., 99, 2012 (1966).
  • For use in the enantioselective conversion of benzylic alcohols to azides, see Diphenyl­phosphonic azide, A12124.
  • Widely used as a base in elimination reactions, cf 1,5-Diazabicyclo[4.3.0]non-5-ene, A13437. For use in dehydrohalogenation, see, e.g. Org. Synth. Coll., 9, 247, 663 (1998).
  • Promotes the epoxidation of ɑß-unsaturated δ-lactones and other enones by t-butyl hydroperoxide, where other bases fail: Tetrahedron, 51, 8573 (1995).
  • Merck: 14,10412
  • Reportedly superior to imidazole for the preparation of TBDMS derivatives of, e.g. amines, thiols and carboxylic acids: Tetrahedron Lett., 26, 475 (1985).

安全信息

Warnings IRRITANT
Signal word Danger
GHS Symbol
WGK Germany2
Safety Statements
  • S16 Keep away from sources of ignition - No smoking 远离火源，禁止吸烟；
  • S20 When using do not eat or drink 使用时，不得进食，饮水；
  • S23 Do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer) 不要吸入气体/烟雾/蒸汽/喷雾；
  • 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；
  • S33 Take precautionary measures against static discharges 对静电采取预防措施；
  • 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）；
  • 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
  • R19 May form explosive peroxides 可能生成易爆的过氧化物质
  • 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
  • R37 Irritating to respiratory system 刺激呼吸道
  • R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
  • R52/53
  • R67 Vapours may cause drowsiness and dizziness 蒸汽可能导致嗜睡和昏厥
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。
  • P234 Keep only in original container. 只保留在原来的容器中。
  • 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。
  • 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+P316
  • P301+P317
  • P301+P330+P331
  • P301+P330+P331+P310
  • P302+P352
  • P302+P361+P354
  • P303+P361+P353
  • P303+P361+P353+P310+P363
  • P304+P340
  • P305+P351+P338
  • P305+P354+P338
  • 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。
  • P316
  • P317
  • P321 Specific treatment (see … on this label). 具体治疗（见本标签上的）。
  • P322 Specific measures (see …on this label). 具体治疗（见本标签上的）。
  • P330 Rinse mouth. 漱口
  • P362+P364
  • P363 Wash contaminated clothing before reuse. 被污染的衣服洗净后方可重新使用。
  • P370+P378
  • P390 Absorb spillage to prevent material damage. 吸收溢出物，防止重大损害。
  • P403+P235
  • P404 Store in a closed container. 贮存于密闭容器中。
  • P405 Store locked up. 上锁保管。
  • P406 Store in corrosive resistant/… container with a resistant inner liner. 存放在耐腐蚀/具有耐性的内衬容器。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
  • H290 May be corrosive to metals 可能腐蚀金属。
  • H301 Toxic if swallowed 吞食有毒
  • H302 Harmful if swallowed 吞食有害
  • H302+H312
  • H312 Harmful in contact with skin 皮肤接触有害
  • H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
  • H318 Causes serious eye damage 严重伤害眼睛
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H336 May cause drowsiness or dizziness 肯能导致嗜睡或头晕
  • H351 Suspected of causing cancer 怀疑致癌
  • H412 Harmfutoaquaticlifewithlonglastingeffects 对水生生物有害并具有长期影响。
Personal Protective Equipment Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
Packing GroupII
UN Number 1173 2924 3267
Storage condition 2-8°C {LY} 2-8°C Air Sensitive Store at R.T. {} {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 {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-
Hazard Codes 3 8 C
Hazard Class8

其他信息

  • F:34
  • 存储注意事项:空气敏感
  • 溶于水。
  • Acros Organics:1,8-二偶氮杂双螺环[5.4.0]十一-7-烯 1,8-Diazabicyclo[5.4.0]undec-7-ene, 98%(6674-22-2)
  • 用途二:该产品用于聚氨基甲醇乙酯及其他化学制品生产的催化剂，如氨和二氯乙烷在它的存在下反应生成哌嗪，是一种优良的脱水剂，环氧树脂硬化剂，防锈剂，还可配制高级缓蚀剂。当前广泛用于头孢半合成抗生素药的生产。还用于有机合成反应和半合成抗菌素。
  • 敏感性:Air Sensitive
  • Sigma Aldrich:6674-22-2(sigmaaldrich)
  • Alfa Aesar:1,8-二氮双环［5.4.0］十一烯,99% 1,8-Diazabicyclo[5.4.0]undec-7-ene, 99%(6674-22-2)
  • 海关编码:29339930
  • MSDS 信息:1,8-Diazabicyclo[5.4.0]undec-7-ene(6674-22-2).msds
  • TCI Shanghai:1,8-二氮杂双环[5.4.0]十一碳-7-烯 1,8-Diazabicyclo[5.4.0]-7-undecene,>;98.0%(GC)(6674-22-2)
  • 用途一:用于头孢半合成抗生素药物的制造，也用于配制脱酸剂、防锈剂、高级缓蚀剂等
  • 1,8-二氮杂双环[5.4.0]十一碳-7-烯价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 D1270 1,8-二氮杂双环[5.4.0]-7-十一碳烯 1,8-Diazabicyclo[5.4.0]-7-undecene 25G 92元 2014/06/02 D1270 1,8-二氮杂双环[5.4.0]-7-十一碳烯 1,8-Diazabicyclo[5.4.0]-7-undecene 500G 589元 2010/06/21 160610250 1,8-二氮杂双环[5.4.0]十一碳-7-烯 1,8-Diazabicyclo[5.4.0]undec-7-ene 98% 25 GR 282元
  • 用途三:用于聚氨基甲醇乙酯及其他化学制品生产的催化剂，如氨和二氯乙烷在它的存在下反应生成哌嗪，是一种优良的脱水剂，环氧树脂硬化剂，防锈剂，还可配制高级缓蚀剂。当前广泛用于头孢半合成抗生素药的生产。还用于有机合成反应和半合成抗菌素。
  • 图谱信息:1,8-二氮杂双环[5.4.0]十一碳-7-烯(6674-22-2)红外图谱(IR1) 1,8-二氮杂双环[5.4.0]十一碳-7-烯(6674-22-2)质谱(MS) 1,8-二氮杂双环[5.4.0]十一碳-7-烯(6674-22-2)核磁图( 1 HNMR) 1,8-二氮杂双环[5.4.0]十一碳-7-烯(6674-22-2)核磁图( 13 CNMR) 1,8-二氮杂双环[5.4.0]十一碳-7-烯(6674-22-2)Raman光谱
  • 蒸气压:5.3 mm Hg ( 37.7 °C)
  • 下游产品:二碳酸二叔丁酯 --> (1R,2R)-N-BOC-1-氨基-2-苯基环丙羧酸 --> 3-(4-甲氧基-6-甲基-1,3,5-三嗪-2-基)-1-(2-甲氧基甲酰基苯基)磺酰脲 --> 9-乙烯基蒽 --> 5-苯基-1,3-氧唑-4-羰酰氯 --> 4-氰基苯乙烯 --> beta-丙内酯 --> [2-[2-(Fmoc-氨基)乙氧基]乙氧基]乙酸 --> 4-硝基苯乙烯 --> 5-苯基-1,3-恶唑-4-羧酸 --> 6-氨基吲哚 --> 6-硝基吲哚 --> 1-氰基异喹啉
  • 检测方法:GC,NMR
  • MOL 文件:6674-22-2.mol

系列性分类

  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Organic Acids - Synthetic Reagents
  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Organic Bases - Synthetic Reagents
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Pyrimidines 嘧啶
  1. Functional Group 官能团索引
  2. carboxylic acid amidine