N-Chlorosuccinimide N-氯代丁二酰亚胺

CAS 128-09-6 MFCD00005511

化学结构图

128-09-6
SMILES: O=C1CCC(=O)N1Cl

化学属性

Mol. FormulaC4H4ClNO2
Mol. Weight133.53
Density1.5
Melting Point148-150°C
TSCAYes
Stability对热、光和湿度敏感
Solubility溶于水和醇类。
RedoxOxidation
Boiling Point216.5 °C at 760 mmHg

别名和识别编码

Chemical NameN-Chlorosuccinimide
Synonym N-Chlorosuccinimide {LY} N-Chlorosuccinimide {} {LY} N-Chlorosuccinimide {} {} {LY} N-Chlorosuccinimide {} {} {} {LY} N-Chlorosuccinimide {} {} {} {} {LY} N-Chlorosuccinimide {} {} {} {} {} {LY} N-Chlorosuccinimide {} {} {} {} {} {} {LY} N-Chlorosuccinimide {} {} {} {} {} {} {} {LY} N-Chlorosuccinimide {} {} {} {} {} {} {} {} {LY} N-Chlorosuccinimide {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} N-Chlorosuccinimide {} {} {} {} {} {} {} {} {} {} {LY} N-Chlorosuccinimide {} {} {} {} {} {} {} {} {} {} {} {LY} N-Chlorosuccinimide {} {} {} {} {} {} {} {} {} {} {} {} {LY} N-Chlorosuccinimide {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} N-Chlorosuccinimide {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} N-Chlorosuccinimide {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} N-Chlorosuccinimide {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
MDL NumberMFCD00005511
CAS Number128-09-6
EC Number204-878-8
Beilstein Registry Number21,380
PubChem Substance ID31398
Merck Number2164
Reaxys-RN113915
Chemical Name TranslationN-氯代丁二酰亚胺
Wiswesser Line NotationT5VNVTJ BG
LabNetwork Molecule IDLN00196334
InChIInChI=1S/C4H4ClNO2/c5-6-3(7)1-2-4(6)8/h1-2H2
Canonical SMILESO=C(CC1)N(Cl)C1=O
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分类

  • {SNA} C-X Bond Formation (Halogen), Chemical Synthesis, Chlorination, Synthetic Reagents
  • {uni_hamburg} no charge; nitrogen heterocycle; alicycle; 5ring; amide; lactame; 1fragment

产品应用

  • 有机合成中作氯化剂,抗菌素药物的中间体。

相关文献及参考

  • Short: II/27C
  • Source of positive chlorine in chlorination and oxidation reactions.
  • Short: III/20a
  • With dimethyl sulfide, forms the Corey-Kim reagent, a mild, selective oxidant for alcohols. For a review, see: Synthesis, 857 (1990); for tabulated examples, see: Org. Synth. Coll., 6, 220 (1988).
  • Methyl ketones may be monochlorinated via their Li enolates: J. Org. Chem., 49, 1286 (1984). For the ɑ-chlorination of acid chlorides formed in situ, see: Tetrahedron Lett., 3235 (1974). For chlorination of deactivated anilines, see: Synthesis, 669 (1985).
  • Merck: 14,2164 Beilstein:21,380
  • Short: III/20c
  • NCS in ether is a convenient alternative to hypochlorite for the conversion of amines to N-chloroamines, for use, e.g. in the Hofmann-Loeffler reaction, see: Chem. Ber., 88, 883 (1955).
  • Primary alcohols are oxidized cleanly to aldehydes using NCS and a catalytic amount of TEMPO, A12733 under phase-transfer conditions: J. Org. Chem., 61, 7452 (1996).
  • Merck: 14,2164
  • In the presence of triphenylphosphine or triphenyl phosphite, converts alcohols to alkyl chlorides stereospecifically with inversion: Tetrahedron Lett., 3937 (1973). For a review, see: Org. React., 29, 1 (1983). Amides have been prepared by treatment of a carboxylic acid with NCS/PPh3 followed by an amine: Synth. Commun., 25, 959 (1995).

安全信息

Signal word Danger
GHS Symbol
WGK Germany3
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);
  • S37/39 Wear suitable gloves and eye/face protection 穿戴适当的手套和眼睛/面保护;
Risk Statements
  • R34 Causes burns 会导致灼伤
  • 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
Precautionary statements
  • P303+P361+P353+P310+P363
  • P390 Absorb spillage to prevent material damage. 吸收溢出物,防止重大损害。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P305+P351+P338
  • 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+P330+P331
  • P405 Store locked up. 上锁保管。
  • P234 Keep only in original container. 只保留在原来的容器中。
  • 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。
  • 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。
  • P304+P340+P310
Hazard statements
  • H290 May be corrosive to metals 可能腐蚀金属。
  • H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
  • H302 Harmful if swallowed 吞食有害
RTECSUY1013500
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
Packing GroupII
UN Number UN 3261 8/PG 2 3261
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 {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {}
Hazard Codes C C,Xi 8
Hazard Class8
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 840 mg/kg/70W-I
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Tumorigenic - tumors at site of application
REFERENCE :
   JNCIAM Journal of the National Cancer Institute.  (Washington, DC)  V.1-60,
   1940-78.  For publisher information, see JJIND8.  Volume(issue)/page/year:
   53,695,1974

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 200 mg/kg
TOXIC EFFECTS :
   Lungs, Thorax, or Respiration - chronic pulmonary edema
   Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
   PHRPA6 Public Health Reports.  (U.S. Government Printing Office, Supt. of
   Documents, Washington, DC 20402)  V.1-    1878-  Volume(issue)/page/year:
   59,541,1944

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 1 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   PHRPA6 Public Health Reports.  (U.S. Government Printing Office, Supt. of
   Documents, Washington, DC 20402)  V.1-    1878-  Volume(issue)/page/year:
   59,541,1944

其他信息

  • Hazard Note:Irritant
  • N-氯代丁二酰亚胺价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 30196627 氯代丁二酰亚胺 250g 199.01元 2011/04/16 C0291 N-氯丁二酰亚胺 N-Chlorosuccinimide 500G 1240元 2011/04/16 C0291 N-氯丁二酰亚胺 N-Chlorosuccinimide 25G 160元
  • 外观:浅黄至白色晶体.
  • Sigma Aldrich:128-09-6(sigmaaldrich)
  • TCI Shanghai:N-氯代丁二酰亚胺 N-Chlorosuccinimide,>;98.0%(T)(128-09-6)
  • Acros Organics:N-氯化琥珀酰亚胺 N-Chlorosuccinimide, 97%(128-09-6)
  • 溶解度:14 g/L水 (20°C)、1g/150ml 乙醇 和1g/50ml 苯,,稍溶于醚、氯仿和四氯化碳,溶于丙酮。1:50水溶液对石蕊呈酸性。有氯的气味
  • 上游原料:氨 --> 氯 --> 次氯酸钠 --> 氯酸钠 --> 丁二酸 --> 次氯酸 --> 丁二酰亚胺
  • 海关编码:29251995
  • 用途三:主要应用在普通有机合成如制药,芳香剂合成,农化品中,也用于合成炔诺酮生物制药等有机合成中。N-氯代丁二酰亚胺(128-09-6)也可作为一种表面处理剂,改善有机合成纤维的性能,并使之不易褪色。
  • 方法一:由丁二酸经氨化、氯化而得。将丁二酸加入的反应锅,滴加氨水,搅拌加热,在102℃蒸去水分。真空蒸馏,收集180℃以后馏分,得丁二酰亚胺。将熔化的丁二酰亚胺加至乙酸水溶液中,搅拌冷却至0-5℃,滴加次氯酸钠,控制在8℃以下反应(否则有爆炸危险)。反应液澄清时即达终点,离心,滤饼用水洗至中性,甩干,干燥,得成品。
  • 存储注意事项:光敏感;湿度敏感
  • 检测方法:T,NMR
  • 企业检测指标参考:有效氯≥26 熔点148-153(℃) 干燥失重≤1 硫分最高0.2% 自由酸最高0.02%
  • 用途二:有机合成中作氯化剂,抗菌素药物的中间体。
  • MOL 文件:128-09-6.mol
  • F:21
  • Alfa Aesar:N-氯丁二酰胺,99% N-Chlorosuccinimide, 98%(128-09-6)
  • 用途一:用作医药中间体、有机合成氯化剂,也可用于制备橡胶助剂
  • MSDS 信息:Chlorosuccinimide(128-09-6).msds
  • 下游产品:2-氯喹啉 --> 3-氨基-4-羟基吡啶盐酸盐 --> (+/-)-5-苯甲酰基-2,3-二氢-1H-吡咯并吡咯烷-1-甲酸 --> 头孢克洛(一水物) --> 2-氯-4-氨基苯胺 --> 4'-溴-3'-氟乙酰苯胺 --> 2-氯-4-(三氟甲基)苯磺酰氯 --> 5-氨基-2,3-二氯吡啶 --> 5-甲基呋喃-2-硼酸 --> 3-(2,6-二氯苯基)-5-甲基异恶唑-4-甲醛 --> 5-甲基-3-苯基异恶唑-4-羧酸 --> 2-氨基-5-氯苯腈 --> 2-乙基环己酮 --> 5-硝基-2,3-二氯吡啶 --> 氟胺氰菊酯 --> 2-正丁基-4(5)-氯-5(4)-甲酰基咪唑 --> 2-氨基-4-苯基-5-噻唑甲酸乙酯 --> 5-硝基-2-羟基-3-氯吡啶
  • 敏感性:Moisture Sensitive

系列性分类