diethyl cyanophosphonate

• ChemBase编号: 87627
• 分子式: C5H10NO3P
• 平均质量: 163.111561
• 单一同位素质量: 163.03982982
• SMILES: P(=O)(C#N)(OCC)OCC
• Canonical SMILES: CCOP(=O)(C#N)OCC
• InChI: InChI=1S/C5H10NO3P/c1-3-8-10(7,5-6)9-4-2/h3-4H2,1-2H3
• InChIKey: ZWWWLCMDTZFSOO-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: diethyl cyanophosphonate
• IUPAC传统名: diethylphosphorocyanidate
• 别名: 氰代磷酸二乙酯; 氰基膦酸二乙酯; Diethyl phosphorocyanidate; (Diethoxyphosphoryl)cyanide; Diethyl cyanophosphonate; Diethyl cyanophosphonate; diethyl phosphorocyanidate; DEPC; Diethyl phosphoryl cyanide

登记号

• CAS号: 2942-58-7
• EC号: 220-936-5
• MDL号: MFCD00010256
• Beilstein号: 1768938
• PubChem SID: 162074667; 24870809; 24857217
• PubChem CID: 76257

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 0.63806987
• LogD (pH = 7.4): 0.63806987
• Log P: 0.63806987
• 摩尔折射率: 36.9701 cm^3
• 极化性: 14.597984 Å^3
• 极化表面积: 59.32 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

• 沸点: 104-105 °C/19 mmHg(lit.); 104-105°C; 104-105°C/19mm; 104-105°C/19mm
• 闪点: 176 °F; 80 °C; 80°C; 80°C(176°F)
• 密度: 1.075; 1.075 g/mL at 25 °C(lit.); 1.091 g/ml
• 折射率: 1.4010; n20/D 1.403(lit.)

安全信息

• 保存条件: 2-8°C, Store Under Nitrogen
• 保存注意事项: Corrosive/Very Toxic/Stench/Moisture Sensitive/Store under Argon/Keep Cold; Moisture Sensitive
• RTECS编号: TD2500000
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C); 剧毒(Highly toxic) (T+); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2922; UN2922
• 德国WGK号: 3
• 联合国危险货物等级: 8
• 联合国危险货物包装类别(PG): 2; II
• 危险公开号: 26/27/28-32-34; 26/27/28-34; R:22-34
• 安全公开号: 26-28-36/37/39-45; 26-28-36/37-45; S:16-26-27/28-36/37/39-46
• TSCA收录: 否
• GHS危险品标识: GHS05; GHS06
• GHS警示词: Danger
• GHS危险声明: H300 +H310 + H330-H314; H300-H310-H330-H314-H318-H227
• GHS警示性声明: P260-P264-P280-P284-P301 + P310-P302 + P350; P280-P305+P351+P338-P302+P352-P304+P340-P309-P310
• 个人保护装置: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2922 8/PG 2
• 欧盟补充危害声明: Contact with acids liberates very toxic gas.
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥90% (GC); 90%; tech. 90%
• 级别: technical
• 线性分子式: (CH3CH2O)2P(O)CN

详细说明

MP Biomedicals - 02150888

Coupling reagent for peptide synthesis.

Sigma Aldrich - 472565

Other Notes
含磷酸三乙酯
包装
5, 25, 100 mL in glass bottle
Application
肽合成的偶联剂。1苯酚的磷酸化试剂。2羧酸荧光衍生化的活化剂，可通过 HPLC 分离活化剂。3

Sigma Aldrich - 28553

Other Notes
用于肽合成的偶联剂1,2

参考文献

• J. Am. Chem. Soc. , 97 : 7174 (1975).
• 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).
• 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):
  
• Phosphorylating agent for phenols: Synth. Commun., 27, 3035 (1997).
• Activates carboxylic acids towards nucleophiles:
• Thiol esters can be formed under similar conditions: J. Org. Chem., 39, 3302 (1974).