Diethyl phosphorocyanidate 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 phosphorocyanidate
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°C,
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

  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Phosphorus Compounds 磷化合物
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Phosphorus Compounds 磷化合物
  5. Phosphonates/Phosphinates - Phosphorus Compounds
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Phosphorus Compounds 磷化合物
  5. Phosphonates/Phosphinates - Phosphorus Compounds
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Phosphorus Compounds 磷化合物
  5. Others
  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Condensation & Active Esterification
  1. Functional Group 官能团索引
  2. phosphonic acid derivative
  1. Functional Group 官能团索引
  2. phosphonic acid ester
  1. Life Science 生命科学
  2. Biochemistry / Glyco-Chemistry
  3. Peptide Synthesis

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