1,1'-Carbonyldiimidazole 1,1-羰基二咪唑(CDI)

CAS 530-62-1 MFCD00005286

化学结构图

530-62-1
SMILES: O=C(n1ccnc1)n1ccnc1

化学属性

Mol. FormulaC7H6N4O
Mol. Weight162.15
Melting Point117-122°C
TSCAT
Density1.303 g/mL at 25 °C
Refractive indexn20/D 1.434
Stability易吸潮
Appearance 白色晶体。熔点115.5-116℃，不溶于水，溶于醇、醚。
Solubility溶于二甲基甲酰胺（DMF）和水（与水反应）。
Boiling Point394.6°C at 760 mmHg

别名和识别编码

Chemical Name1,1'-Carbonyldiimidazole, >90%
CAS Number530-62-1
Alfabeta NameCARBONYLDIIMIDAZOLE NN-,'
MDL NumberMFCD00005286
Synonym N,N'-Carbonyldiimidazole {LY} N,N'-Carbonyldiimidazole N,N'-carbonyldiimidazole N,N-carbonyldiimidazole {} {LY} N,N'-Carbonyldiimidazole {} {} {LY} N,N'-Carbonyldiimidazole {} {} {} {LY} N,N'-Carbonyldiimidazole {} {} {} {} {LY} N,N'-Carbonyldiimidazole {} {} {} {} {} {LY} N,N'-Carbonyldiimidazole {} {} {} {} {} {} {LY} N,N'-Carbonyldiimidazole {} {} {} {} {} {} {} {LY} N,N'-Carbonyldiimidazole {} {} {} {} {} {} {} {} {LY} N,N'-Carbonyldiimidazole {} {} {} {} {} {} {} {} {} {LY} N,N'-Carbonyldiimidazole {} {} {} {} {} {} {} {} {} {} {LY} N,N'-Carbonyldiimidazole {} {} {} {} {} {} {} {} {} {} {} {LY} N,N'-Carbonyldiimidazole {} {} {} {} {} {} {} {} {} {} {} {} {LY} N,N'-Carbonyldiimidazole {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} N,N'-Carbonyldiimidazole {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} N,N'-Carbonyldiimidazole {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} N,N'-Carbonyldiimi
PubChem Substance ID68263
EC Number208-488-9
Beilstein Registry Number6826
Reaxys-RN6826
Merck Number1819
Chemical Name Translation1,1-羰基二咪唑(CDI)
LabNetwork Molecule IDLN00121303
InChIInChI=1S/C7H6N4O/c12-7(10-3-1-8-5-10)11-4-2-9-6-11/h1-6H
Canonical SMILESO=C(N1C=NC=C1)N2C=NC=C2
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分类

  • Intermediates
  • Heterocycles
  • {SNA} Carbonyldiimidazole Derivatives, Chemical Biology, Chemical Synthesis, Coupling, Peptide Chemistry, Peptide Coupling, Synthetic Reagents
  • {SNA} Carbonyldiimidazole Derivatives, Chemical Synthesis, Coupling, Synthetic Reagents

产品应用

  • 多肽试剂，用于生化合成基团保护及蛋白质肽链的连接。作为合成三磷核苷、肽、和酯类的缩合剂；以及是合成酰基咪唑和吡藜酰胺的重要中间体。

相关文献及参考

  • Merck:14,1819
  • ɑß-Dihydroxyketones are converted toɑ-diketones: Synth. Commun., 23, 2219 (1993).
  • Dehydrates aldoximes, including chiral oximes, to nitriles in high yield: J. Chem. Soc., Chem. Commun., 628 (1973); Synth. Commun., 12, 25 (1982). Ketoximes can be converted to amides by the spontaneous Beckmann rearrangement of imidazolium salts: Chem. Pharm. Bull., 32, 2560 (1984):
  • Acylimidazolides can also be reduced to aldehydes by DIBAL-H. This reaction has been applied to N-protected amino acids: J. Chem. Soc., Chem. Commun., 79 (1979).
  • Merck:14,1819 Beilstein:23(3/4)575
  • Pierschbacher, M., et al.: Nature, 309, 30
  • ß-Hydroxy amino acids are dehydrated to dehydroamino acids: Synthesis, 968 (1982).
  • One-pot esterification of a carboxylic acid with t-BuOH occurs in the presence of DBU: Synthesis, 833 (1982). The reactivity of acyl imidazolides can be increased by N-alkylation: Chem. Pharm. Bull., 32, 5044 (1984).
  • Reagent for peptide coupling via the acylimidazolide: Liebigs Ann. Chem., 609, 75 (1957); J. Am. Chem. Soc., 80, 4423 (1958); 82, 4596 (1960): J. Org. Chem., 27, 2094 (1962). For peptide reagents, see Appendix 6.

安全信息

Warnings MOISTURE SENSITIVE, KEEP COLD, CORROSIVE, STORED UNDER ARGON
GHS Symbol
WGK Germany2
Hazard Codes 8 C
Hazard statements
  • 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
  • H318 Causes serious eye damage 严重伤害眼睛
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H351 Suspected of causing cancer 怀疑致癌
  • H360 May damage fertility or the unborn child 可能对生育能力或未出生婴儿造成伤害
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 Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
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
  • 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。
  • 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
  • P301+P330+P331+P310
  • P302+P352
  • P302+P361+P354
  • P303+P361+P353
  • P303+P361+P353+P310+P363
  • P304+P340
  • P304+P340+P310
  • P305+P351+P338
  • P305+P351+P338+P310
  • P305+P354+P338
  • P308+P313
  • P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或医生/医师。
  • P316
  • P317
  • P318
  • 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
  • P363 Wash contaminated clothing before reuse. 被污染的衣服洗净后方可重新使用。
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Signal word Danger
UN Number 1759 3263 UN 3263 8/PG 2 UN3263
Storage condition RT, protect from light, stored under nitrogen {LY} RT, protect from light, stored under nitrogen {} {LY} RT, protect from light, stored under nitrogen {} {} {LY} RT, protect from light, stored under nitrogen {} {} {} {LY} RT, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {LY} RT, protect from light, stored under nitrogen {} {} {} {} {} {LY} RT, protect from light, stored under nitrogen {} {} {} {} {} {} {LY} RT, protect from light, stored under nitrogen {} {} {} {} {} {} {} {LY} RT, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {LY} RT, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} RT, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {LY} RT, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} RT, protect from light, stored under nitrogen {} {} {} {} {} {} {} {
Safety Statements
  • 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）；
Risk Statements
  • R22 Harmful if swallowed 吞咽有害
  • R34 Causes burns 会导致灼伤
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R36/38 Irritating to eyes and skin 对眼睛和皮肤有刺激性
  • R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
Packing GroupII
Hazard Class8

其他信息

  • MSDS 信息:1,1'-Carbonyldiimidazole(530-62-1).msds
  • 存储注意事项:氮气保护;湿度敏感
  • Sigma Aldrich:530-62-1(sigmaaldrich)
  • Acros Organics:1,1'-羰基二咪唑 1,1'-Carbonyldiimidazole, 97%(530-62-1)
  • Hazard Note:Harmful/Corrosive/Moisture Sensitive
  • 用途二:用于有机合成。
  • 上游原料:咪唑
  • Alfa Aesar:N,N'-羰基二咪唑,97% 1,1'-Carbonyldiimidazole, 97%(530-62-1)
  • 接触空气易变质，遇水在几分钟内即水解，并释放出CO2。不溶于水，溶于乙醇、醚等有机溶剂,中度溶于THF.
  • 方法一:将咪唑与溶于苯的光气反应，滤除反应物中的咪唑盐酸盐，滤液浓缩至干，得1,1'-羰基二咪唑，产率91%。
  • F:10-21
  • 图谱信息:N,N'-羰基二咪唑(530-62-1)红外图谱(IR1) N,N'-羰基二咪唑(530-62-1)质谱(MS) N,N'-羰基二咪唑(530-62-1)核磁图( 13 CNMR) N,N'-羰基二咪唑(530-62-1)核磁图( 1 HNMR)
  • 海关编码:29332990
  • TSCA:T
  • 用途三:多肽试剂，用于生化合成基团保护及蛋白质肽链的连接。作为合成三磷核苷、肽、和酯类的缩合剂；以及是合成酰基咪唑和吡藜酰胺的重要中间体。
  • 检测方法:HPLC
  • 下游产品:1-叔丁氧羰基-4-氨甲基哌啶 --> 2-乙基哌嗪 --> 4-叔丁氧羰基氨基哌啶 --> 5-溴-2-苯并恶唑酮 --> 帕珠沙星 --> 6-氯-3-氰基吡啶 --> 4-氰基哌啶 --> 1,3-噻唑烷-2-酮 --> 2-氨基-5-溴苯甲酰胺 --> 吲哚-3-丙胺 --> 3-溴噻吩-2-羰基胺 --> DAN --> N-1-Boc-2-甲基哌嗪 --> 3-氰基-5-氨基吡啶 --> 5-(吡啶-3-基)-1H-吡唑-3-甲酰胺 --> 2-(叔丁氧羰基氨基甲基)-哌啶 --> 4-Boc-氨甲基哌啶 --> 1,4-二乙酰基哌啶 --> 普罗加比 --> 3-噻吩乙腈 --> N-七氟丁酰基咪唑
  • MOL 文件:530-62-1.mol
  • N,N'-羰基二咪唑价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 xw020051 N,N’-羰基二咪唑 (CDI)（2-8℃） 100g 158元 2011/08/23 xw020073 N,N’-羰基二咪唑 (CDI)（2-8℃） 500g 480元 2011/04/16 C0119 1,1'-羰基二咪唑[用于肽合成的偶联剂] 1,1'-Carbonyldiimidazole [Coupling Agent for Peptides Synthesis] 250G 3560元
  • 敏感性:Moisture Sensitive
  • TCI Shanghai:N,N'-羰基二咪唑[用于肽合成的偶联剂] 1,1'-Carbonyldiimidazole [Coupling Agent for Peptides Synthesis],>;95.0%(W)(530-62-1)
  • 用途一:用作农药、医药中间体

系列性分类

  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. Imidazoles 咪唑
  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Coupling - Synthetic Reagents
  4. Carbodiimides - Coupling
  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Coupling - Synthetic Reagents
  4. Carbonyldiimidazole Derivatives - Coupling
  1. Chemical Synthesis 化学合成
  2. Chemical Biology 生物化学
  3. Peptide Chemistry 多肽化学
  4. Peptide Coupling - Peptide Chemistry
  5. Carbonyldiimidazole Derivatives - Peptide Coupling
  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Condensation & Active Esterification
  1. Life Science 生命科学
  2. Biochemistry / Glyco-Chemistry
  3. Peptide Synthesis