二(2-氯乙基)氯磷酸酯 | 6087-94-1

• 物质功能分类: 化学试剂 - 有机试剂 - 膦酸酯/膦酸盐
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 中文名称: 二(2-氯乙基)氯磷酸酯
• 英文名称: bis(2-chloroethyl) chlorophosphate
• 英文别名: bis(2-chloroethyl)chlorophosphonate；phosphorochloridic acid bis-(2-chloro-ethyl) ester；chlorophosphoric acid bis-(2-chloro-ethyl ester)；Chlorophosphorsaeure-bis-(2-chlor-aethylester)；Phosphorsaeure-bis-(2-chlor-aethylester)-chlorid；bis(2-chloroethyl) phosphorochloridate；1-chloro-2-[chloro(2-chloroethoxy)phosphoryl]oxyethane
• CAS: 6087-94-1
• 化学式: C₄H₈Cl₃O₃P
• 分子量: 241.438
• InChiKey: XETKNKZXWYEULP-UHFFFAOYSA-N

物化性质

• 熔点：
  124-126 °C
• 沸点：
  137-139 °C(Press: 5 Torr)
• 密度：
  1.4623 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  二(2-氯乙基)氯磷酸酯 在 乙醚 、 水 、 三乙胺 作用下， 生成 焦磷酸四(2-氯乙基)酯
  参考文献：
  名称：

  Nikonorow et al., 1955, p. 223,228,230

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯乙醇 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 生成 二(2-氯乙基)氯磷酸酯
  参考文献：
  名称：

  Ethyl Octylphosphonofluoridate and Analogs: Optimized Inhibitors of Neuropathy Target Esterase

  摘要：

  The relation between organophosphorus-induced delayed neuropathy (OPIDN) and brain neuropathy target esterase (NTE) inhibition is further examined in hens by structure-activity studies leading to the most potent in vitro NTE inhibitors known, which are then examined for their neuropathic effects in vivo in hens. The principal compounds studied are alkyl alkylphosphonofluoridates and dialkyl phosphorofluoridates. Potencies that exceed those of any previous inhibitors under the standard in vitro NTE assay condition are achieved with alkyl octylphosphonofluoridates (ethyl, isopropyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, and 3-iodopropyl), 2-iodoethyl hexylphosphonofluoridate, and dialkyl phosphorofluoridates [ethyl, nonyl; di(2-iodoethyl); di(3-iodopropyl); dipentyl]. The concentration for 50% NTE inhibition (I-50) Of these compounds is 0.04-0.14 nM. Thirty-eight less active analogs including aryl phosphonates and aryl phosphates give I(50)s of 0.27-4730 nM. For highest potency the summation of length of the alkyl and alkoxy groups on phosphorus should be 12-16 atoms (carbons, oxygens, and phosphorus) (a terminal iodo substituent in this relationship is equivalent to a propyl group). In general, the phosphonofluoridates and phosphorofluoridates are more active than analogs with leaving groups other than fluorine, i.e., phenoxy, 4-nitrophenoxy, 4-cyanophenoxy, 3,4-dichlorophenoxy, and 4H-1,3,2-benzodioxaphosphorin. Considering the exceptional potencies of ethyl and 2-iodoethyl octylphosphonofluoridates (I50S of 0.04 and 0.09 nM, respectively), it is not surprising that at ip doses of 10-30 mg/kg they inhibit brain NTE by 82-97% 48 h after treatment. However, unexpectedly, only the ethyl but not the 2-iodoethyl compound induces OPIDN, possibly associated with the greater ease of aging for NTE inhibited with the ethyl than the 2-iodoethyl compound (as observed in vitro both spontaneously and on induction by potassium fluoride). The high potency of ethyl octylphosphonofluoridate and several analogs as NTE inhibitors suggests that they are useful probes in determining the toxicological features of this secondary lesion for organophosphorus poisoning.

  DOI：

  10.1021/tx00050a011

文献信息

• Reactivity of an electrophilic hypervalent iodine trifluoromethylation reagent with hydrogen phosphates—A mechanistic study
  作者：Nico Santschi、Patrik Geissbühler、Antonio Togni

  DOI：10.1016/j.jfluchem.2011.08.014

  日期：2012.3

  The electrophilic trifluoromethylation of hydrogen phosphates with the reagent trifluoromethyl-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole (1) was studied by means of initial rates determined for pseudo first order setups and subsequent Taft analysis of the calculated relative rates. A positive polar sensitivity factor, indicative of a negative charge forming during the rate-determining step, was found

  用拟一级装置确定的初始速率和随后的塔夫脱（Taft）分析法研究了用试剂三氟甲基-1,3-二氢-3，3-二甲基-1,2-苯并恶唑（1）对磷酸氢的亲电三氟甲基化反应。计算的相对比率。对于整个数据集，发现了一个正极性灵敏度因子，表明在速率确定步骤中形成了负电荷。
• Arbeiten über Phosphorsäure- und Thiophosphorsäure-ester mit einem heterocyclischen Substituenten. 6. Mitteilung. 3-Acyl-thio- und -dithio-carbazinsäure-alkylester und 2′-(Dialkoxy-phosphinothioyl)-carbonsäurehydrazide sowie deren Ringschluss zu 3-Acyl-5-
  作者：Kurt Rüfenacht

  DOI：10.1002/hlca.19730560108

  日期：1973.1.31

  Thio- and dithio-carbazic acid alkyl esters, acylated in position 3 by radicals of carboxylic, sulfonic, phosphoric, thiophosphoric or thiophosphonic acids, undergo spontaneous ring closure with phosgene, in absence of any acid binding agent, to form the corresponding 3-acyl-5-alkoxy- and -5-alkylthio-l,3,4-thiadiazol-2(3H)-ones. Similarly 3-thiophosphorylated 5-substituted 1,3,4-oxadiazol-2(3H)-ones

  在3位上被羧酸，磺酸，磷酸，硫代磷酸或硫代膦酸的自由基酰化的硫代和二硫代氨基甲酸烷基酯，在没有任何酸结合剂的情况下，用光气自发地闭环，形成相应的3-酰基-5-烷氧基-和-5-烷硫基-1,3,4-噻二唑-2（3 H）-。类似地，可以由被硫代磷酸基团酰化的羧酸酰肼制备3-硫代磷酸化的5-取代的1,3,4-恶二唑-2（3H）-。然而，在后一种情况下，需要化学计量的吡啶以避免PN键的断裂。
• 一种单磷酸阿糖腺苷的生产工艺
  申请人：海南卓科制药有限公司

  公开号：CN109134569B

  公开（公告）日：2019-07-05

  本发明属于单磷酸阿糖腺苷制备技术领域，具体涉及一种单磷酸阿糖腺苷的生产工艺，该工艺包括如下步骤：S1将阿糖腺苷溶解于有机溶剂中，降温；S2加入磷酰氯，保温反应至阿糖腺苷剩余量不超过加入量的3％时停止；S3加入钯催化剂催化还原后过滤，将所得滤液除去溶剂即得单磷酸阿糖腺苷粗品；S4将步骤S3得到的单磷酸阿糖腺苷粗品重结晶纯化。利用本发明提供的单磷酸阿糖腺苷的生产工艺引用反应活性相对较低的磷酰氯与原料阿糖腺苷反应，反应温和，易控制，从反应源头减少了副产物的生成数量；而且利用新颖的钯催化剂选择性的对引入的醚基进行还原，纯化工艺简单，目标产品产率和纯度高。
• 1-Phosphorosemicarbazides
  申请人：Olin Corporation

  公开号：US03992488A1

  公开（公告）日：1976-11-16

  1-Phosphorosemicarbazides having the formula ##EQU1## are effective and durable additives for reducing the combustibility of cotton fabrics to which they are applied.

  具有以下公式的1-磷酸半脲类物质##EQU1## 是有效和耐久的添加剂，可降低应用于棉织物上的燃烧性。
• Process for preparing bis(2-haloalkyl) phosphoro-halidates
  申请人：Olin Corporation

  公开号：US03987129A1

  公开（公告）日：1976-10-19

  An improved process is disclosed for the preparation of bis(2-haloalkyl) phosphorohalidates. This process comprises the steps of reacting phosphorus trihalide with a stoichiometric excess of alkylene oxide to form tris(2-haloalkyl) phosphite, substantially eliminating the presence of unreacted alkylene oxide in the tris(2-haloalkyl) phosphite, and finally converting it to bis(2-haloalkyl) phosphorohalidate by reaction with halogen.

  本发明公开了一种改进的制备双(2-卤代烷基)磷酸卤酯的方法。该方法包括以下步骤：将三卤代磷与过量的烷氧基化合物反应，形成三(2-卤代烷基)磷酸酯，从三(2-卤代烷基)磷酸酯中实质性地消除未反应的烷氧基化合物的存在，最后通过与卤素反应将其转化为双(2-卤代烷基)磷酸卤酯。