N-Hydroxysuccinimide (HOSu) N-羟基琥珀酰亚胺(NHS)

CAS 6066-82-6 MFCD00005516

化学结构图

6066-82-6
SMILES: O=C1CCC(=O)N1O

化学属性

Mol. FormulaC4H5NO3
Mol. Weight115.09
Density1.649
Melting Point95-98°C
TSCAYes
SolubilitySoluble in water (50 mg/ml), DMSO (100 mM), methanol, acetone (50 mg/ml), and DMF.
Stability对热、湿度敏感
Appearance 白色结晶体。熔点99-100℃。
Boiling Point262.4°C at 760 mmHg

别名和识别编码

Chemical NameN-Hydroxysuccinimide (HOSu)
CAS Number6066-82-6
Synonym N-Hydroxysuccinimide {LY} N-Hydroxysuccinimide {} {LY} N-Hydroxysuccinimide {} {} {LY} N-Hydroxysuccinimide {} {} {} {LY} N-Hydroxysuccinimide {} {} {} {} {LY} N-Hydroxysuccinimide {} {} {} {} {} {LY} N-Hydroxysuccinimide {} {} {} {} {} {} {LY} N-Hydroxysuccinimide {} {} {} {} {} {} {} {LY} N-Hydroxysuccinimide {} {} {} {} {} {} {} {} {LY} N-Hydroxysuccinimide {} {} {} {} {} {} {} {} {} {LY} N-Hydroxysuccinimide {} {} {} {} {} {} {} {} {} {} {LY} N-Hydroxysuccinimide {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} N-Hydroxysuccinimide {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {LY} N-Hydroxysuccinimide {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} N-Hydroxysuccinimide {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} N-Hydroxysuccinimide {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} N-Hydroxysuccinimide {} {} {} {} {} {}
MDL NumberMFCD00005516
EC Number228-001-3
Beilstein Registry Number21,380
PubChem Substance ID87570998
Reaxys-RN113913
Chemical Name TranslationN-羟基琥珀酰亚胺(NHS)
LabNetwork Molecule IDLN00008611
InChIInChI=1S/C4H5NO3/c6-3-1-2-4(7)5(3)8/h8H,1-2H2
Canonical SMILESO=C(N1O)CCC1=O
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分类

  • {SNA} Active Esters/Additives, Chemical Reagents, Chemical Synthesis, Coupling, Development Quantities for Research, Synthetic Reagents
  • Heterocycles
  • {SNA} Active Esters/Additives, Chemical Biology, Chemical Synthesis, Coupling, Peptide Chemistry, Peptide Coupling, Synthetic Reagents
  • Miscellaneous Reagents
  • {SNA} Chemical Reagents, Active Esters/Additives, Chemical Synthesis, Coupling, Development Quantities for Research, Synthetic Reagents

产品应用

  • Useful in the carbodiimide method for improved amidations and peptide couplings.

相关文献及参考

  • For a study of the aminolysis of N-hydroxysuccinimide esters, see: J. Org. Chem., 53, 3583 (1988).
  • Merck: 14,10330
  • Merck: 14,10330 Beilstein: 21,V,9,498
  • Reagent for the preparation of active N-hydroxysuccinimide esters for peptide coupling with minimum racemization: J. Am. Chem. Soc., 86, 1839 (1964), or as an additive in the DCC method (see N,N'-Dicyclohexyl­carbodiimide, A10973) to suppress racemization: J. Am. Chem. Soc., 89, 7151 (1967). For peptide reagents, see Appendix 6.

安全信息

Signal word Warning
GHS Symbol
WGK Germany3
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘;
  • 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;
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触;
  • 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;
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Precautionary statements
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Storage condition 2-8°C {LY} 2-8°C {} {LY} 2-8°C {} {} {LY} 2-8°C {} {} {} {LY} 2-8°C {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {}
Hazard Codes Xi

其他信息

  • 用途四:用于合成氨基酸保护剂及医药中间体。
  • 用途一:用于合成氨基酸保护剂、半合成卡那霉素及医药中间体。
  • N-羟基丁二酰亚胺价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 30104633 N-羟基丁二酰亚胺(+4℃) 10g 103.5元 2011/04/16 H0623 N-羟基琥珀酰亚胺 N-Hydroxysuccinimide 25G 260元 2011/04/16 H0623 N-羟基琥珀酰亚胺 N-Hydroxysuccinimide 500G 2970元
  • 下游产品:依那普利 --> 咪达普利 --> N-丙烯酰氧基琥珀酰亚胺 --> 阿贝卡星 --> (2S,5R,6R)-6-[(2R)-2-[(2R)-2-氨基-3-(N-甲基氨基甲酰)-丙酰胺基]-2-(4-羟基苯基)乙酰胺基]-3,3-二甲基-7-氧代-4-硫-1-氮杂双环[3.2.0]庚烷-2-羧酸三水物 --> 胍立莫司
  • MSDS 信息:1-Hydroxy-2,5-pyrrolidinedione(6066-82-6).msds
  • 海关编码:29251995
  • 检测方法:T,NMR
  • MOL 文件:6066-82-6.mol
  • 用途二:用作半合成抗菌素中间体
  • Alfa Aesar:N-羟基丁二酰亚胺,98+% N-Hydroxysuccinimide, 98+%(6066-82-6)
  • Hazard Note:Irritant
  • 方法一:将100g(1.0mol)丁二酸酐和70g(1.0mol)盐酸羟胺一起加热,使反应系统保持负压抽除生成的挥发物,迅速加热至125℃以上,1h后慢慢升至160℃。停止加热,当温度降至125℃时,将液态反应物倾入400ml乙醚中并激烈搅拌。产物固化后倾去乙醚层,固化物与400ml丁醇共热至沸,热滤,滤液迅速冷却至0℃。1h后过滤,结晶依次用丁醇、乙醚洗涤,所得粗品用乙酸乙酯重结晶,得50g成品,收率44%。
  • 敏感性:Hygroscopic
  • Sigma Aldrich:6066-82-6(sigmaaldrich)
  • N-Hydroxysuccinimide, commonly known as NHS, is a hydroxylated succinimide that is widely used in the activation of carboxylic acids to NHS-esters to promote coupling with nucleophiles. This approach is most commonly employed in activating the free acid forms of fluorophores for promoting conjugation of these fluorophores to amine residues of proteins. Use of NHS ester activation has also been described in the synthesis of N-acyl amino acids.
  • 用途三:医药中间体,用于生产半合成卡那霉素。
  • Acros Organics:N-羟基琥珀酰亚胺 N-Hydroxysuccinimide, 98+%(6066-82-6)
  • 对潮湿敏感,溶于水,易溶于丙酮、醇和乙酸乙酯;微溶于氯代烃、醚、甲苯和苯。产品易结块。
  • TCI Shanghai:N-羟基琥珀酰亚胺 N-Hydroxysuccinimide,>;98.0%(T)(6066-82-6)
  • 上游原料:盐酸羟胺 --> 丁二酸酐

系列性分类