Diethyl Cyanophosphonate 氰基磷酸二乙酯

CAS 2942-58-7 MFCD00010256

化学结构图

2942-58-7
SMILES: CCOP(=O)(C#N)OCC

化学属性

Mol. FormulaC5H10NO3P
Mol. Weight163.11
Refractive index1.4010 to 1.4030
Boiling Point104-105 °C at 19 mmHg
Density1.07
Flash Point81°C(lit.)
TSCANo
Solubility分解
Appearance 无色液体。沸点104-105℃(2.53kPa),相对密度1.075,折光率1.4010。
Stability对湿度敏感

别名和识别编码

Chemical NameDiethyl Cyanophosphonate
Synonym Diethyl phosphorocyanidate {LY} Diethyl phosphorocyanidate {} {LY} Diethyl phosphorocyanidate {} {} {LY} Diethyl phosphorocyanidate {} {} {} {LY} Diethyl phosphorocyanidate {} {} {} {} {LY} Diethyl phosphorocyanidate {} {} {} {} {} {LY} Diethyl phosphorocyanidate {} {} {} {} {} {} {LY} Diethyl phosphorocyanidate {} {} {} {} {} {} {} {LY} Diethyl phosphorocyanidate {} {} {} {} {} {} {} {} {LY} Diethyl phosphorocyanidate {} {} {} {} {} {} {} {} {} {LY} Diethyl phosphorocyanidate {} {} {} {} {} {} {} {} {} {} {LY} Diethyl phosphorocyanidate {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Diethyl phosphorocyanidate {} {} {} {} {} {} {} {} {} {} {} {} {LY} Diethyl phosphorocyanidate {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Diethyl phosphorocyanidate {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Diethyl phosphorocyanidate {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
CAS Number2942-58-7
PubChem Substance ID87566263
EC Number220-936-5
Beilstein Registry Number1768938
MDL NumberMFCD00010256
Reaxys-RN1768938
Chemical Name Translation氰基磷酸二乙酯
InChIKeyZWWWLCMDTZFSOO-UHFFFAOYSA-N
Wiswesser Line NotationNCPO&O2&O2
LabNetwork Molecule IDLN00848328
InChIInChI=1S/C5H10NO3P/c1-3-8-10(7,5-6)9-4-2/h3-4H2,1-2H3
Canonical SMILESO=P(OCC)(C#N)OCC
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分类

  • {SNA} Building Blocks, Chemical Synthesis, Organic Building Blocks, Phosphonates/Phosphinates, Phosphorus Compounds

产品应用

  • 常用作肽合成的偶联剂、苯酚的磷酸化试剂;还可用于羧酸荧光衍生化的活化剂,可通过 HPLC 分离活化剂。

相关文献及参考

  • Strecker reaction with aldehydes or ketones in the presence of amines or ammonia gives goodyields ofɑ-amino nitriles: Tetrahedron Lett., 4663 (1979). Pre-formed enamines give the same products: Synthesis, 716 (1979).
  • Phosphorylating agent for phenols: Synth. Commun., 27, 3035 (1997).
  • Activates carboxylic acids towards nucleophiles:
  • Beil. 3 ,IV,260
  • Thiol esters can be formed under similar conditions: J. Org. Chem., 39, 3302 (1974).
  • Beilstein: 3,IV,260
  • Promotes the formation of amides and esters from amines or alcohols in the presence of, e.g. triethylamine : Tetrahedron, 32, 2211 (1976). The reaction is applicable to peptide synthesis, since little racemization has been observed: J. Am. Chem. Soc., 97, 7174 (1975). The extent of racemization in comparison with other methods has been studied: Chem. Pharm. Bull., 30, 3147 (1982). See Appendix 6. With 2 equivalents of reagent in the absence of a nucleophile, an intermediate 1-(1,1-dicyano)phosphate is formed, leading, on treatment with acid, to the homologated ɑ-hydroxy acid: Tetrahedron Lett., 39, 9209 (1998).
  • Can also be used to activate carboxylic acids for the C-acylation of active methylene compounds: J. Org. Chem., 43, 3631 (1978). In the presence of Lewis acids, active methylene compounds such as dimethyl malonate react with the cyanophosphonate itself. The product can be converted to a uracil derivative by reaction with phenyl isocyanate: Chem. Pharm. Bull., 42, 1919 (1994):

安全信息

GHS Symbol
WGK Germany3
Hazard statements
  • H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
  • H300+H310+H330
  • H227 Combustible liquid 可燃液体
Personal Protective Equipment Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
Hazard Codes C,Xi,T+ T+,C C T+;C
RTECSTD2500000
Precautionary statements
  • 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。
  • P305+P351+P338+P310
  • P303+P361+P353
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • 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。
  • 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
  • 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。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P303+P361+P353+P310+P363
  • P370+P378
  • P405 Store locked up. 上锁保管。
  • P304+P340
  • P302+P350
  • P301+P330+P331
  • 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
  • P301+P330+P331+P310
  • P403+P233
  • 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。
Signal word
UN Number 2922
Risk Statements
  • R26/27/28 Very toxic by inhalation, in contact with skin and if swallowed 吸入,皮肤接触及吞食都有剧毒
  • R34 Causes burns 会导致灼伤
  • R32 Contact with acids liberates very toxic gas 与酸接触释放出毒性很高的气体
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
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;
  • S28 After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) 皮肤接触后,立即用大量…(由生产厂家指定)冲洗;
  • 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);
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套;
Storage condition 2-8°C, stored under nitrogen {LY} 2-8°C, stored under nitrogen Moisture Sensitive {} {LY} 2-8°C, stored under nitrogen {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°
Packing GroupIII
Hazard Class8/6.1
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : 4 mg/kg
TOXIC EFFECTS :
   Lungs, Thorax, or Respiration - other changes
REFERENCE :
   JCSOA9 Journal of the Chemical Society.  (London, UK)  1926-65.  For
   publisher information, see JCPRB4.  Volume(issue)/page/year: -,699,1948

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 25 mg/kg
TOXIC EFFECTS :
   Lungs, Thorax, or Respiration - other changes
REFERENCE :
   JCSOA9 Journal of the Chemical Society.  (London, UK)  1926-65.  For
   publisher information, see JCPRB4.  Volume(issue)/page/year: -,699,1948

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1400 ug/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   PAREAQ Pharmacological Reviews.  (Williams & Wilkins, 428 E. Preston St.,
   Baltimore, MD 21202) V.1-    1949-  Volume(issue)/page/year: 11,636,1959

其他信息

  • 图谱信息:氰基磷酸二乙酯(2942-58-7)质谱(MS) 氰基磷酸二乙酯(2942-58-7)红外图谱(IR1)
  • 下游产品:膦甲酸钠
  • 用途二:多肽缩合剂[1],酚羟基磷酸化试剂[2],含羧基化合物进行HPLC分析时制备荧光衍生物时的活化剂。
  • Acros Organics:氰基磷酸二乙酯 Diethyl cyanophosphonate, 93%(2942-58-7)
  • Sigma Aldrich:2942-58-7(sigmaaldrich)
  • Hazard Note:Irritant
  • 用途一:有机合成中间体。
  • 上游原料:溴氰 --> 磷酸二乙酯
  • 氰基磷酸二乙酯价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 C1242 氰基磷酸二乙酯 Diethyl Cyanophosphonate 25G 1350元 2014/06/02 C1242 氰基磷酸二乙酯 Diethyl Cyanophosphonate 5G 404元 2010/06/21 224290050 氰基磷酸二乙酯 Diethyl cyanophosphonate 93% 5 GR 450元
  • TCI Shanghai:氰基磷酸二乙酯 Diethyl Cyanophosphonate,>;93.0%(GC)(2942-58-7)
  • F:10-13-21
  • 方法一:将过量的溴化氰滴入磷酸二乙酯中,反应液逐渐变热。反应毕,减压蒸馏,收集104-105℃(2.53kPa)馏分,得氰基磷酸二乙酯。收率65%。
  • Alfa Aesar:腈基磷酸二乙酯,tech.90% Diethyl cyanophosphonate, tech. 90%(2942-58-7)
  • MSDS 信息:DEPC(2942-58-7).msds
  • 敏感性:Moisture Sensitive
  • MOL 文件:2942-58-7.mol

系列性分类


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