双(二乙基胺基)磷酰氯 | 1794-24-7

• 物质功能分类: 化学试剂 - 有机试剂 - 酰卤
• 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: 双(二乙基胺基)磷酰氯
• 中文别名: 双(二乙基氨基)氯酸偶膦；双(N,N-二乙基氨基)膦酰氯
• 英文名称: tetraethyldiamidochlorophosphate
• 英文别名: Bis(diethylamino)phosphoryl chloride；N-[chloro(diethylamino)phosphoryl]-N-ethylethanamine
• CAS: 1794-24-7
• 化学式: C₈H₂₀ClN₂OP
• mdl: MFCD00137958
• 分子量: 226.686
• InChiKey: HKKBJRUSFKTHSU-UHFFFAOYSA-N

物化性质

• 沸点：
  101 °C (0.3 mmHg)
• 密度：
  1.07
• 闪点：
  101°C/0.3mm
• 稳定性/保质期：
  对湿气敏感，可能与氧化剂和碱发生反应。

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 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：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  8
• 危险品标志：
  C
• 危险类别码：
  R34
• 危险品运输编号：
  UN 1759
• 包装等级：
  II
• 危险类别：
  8
• 安全说明：
  S36/37/39,S45
• 储存条件：
  在干燥且惰性气体保护的环境中密封保存，并存放在阴凉干燥处。避免与湿气和水源接触。

SDS

Name:	Bis(diethylamino)phosphochloridate 99% Material Safety Data Sheet
Synonym:
CAS:	1794-24-7

Section 1 - Chemical Product MSDS Name:Bis(diethylamino)phosphochloridate 99% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1794-24-7	Bis(diethylamino)phosphochloridate	99%	217-262-9

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.Moisture sensitive.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
Causes chemical burns to the respiratory tract. Inhalation may be fatal as a result of spasm, inflammation, edema of the larynx and bronchi, chemical pneumonitis and pulmonary edema.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do not induce vomiting. If victim is conscious and alert, give 2-4 cupfuls of milk or water. Get medical aid immediately.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.

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Section 7 - HANDLING and STORAGE
Handling:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use and store under nitrogen. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area. Keep refrigerated. (Store below 4C/39F.)

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1794-24-7: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: Not available.
Odor: pungent odor
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 101 deg C @ .30mm H
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.0700g/cm3
Molecular Formula:
Molecular Weight: 226.58

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong bases, amines, alcohols.
Hazardous Decomposition Products:
Hydrogen chloride, phosphine, carbon monoxide, oxides of nitrogen, oxides of phosphorus, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1794-24-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Bis(diethylamino)phosphochloridate - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: CORROSIVE LIQUID, N.O.S.*
Hazard Class: 8
UN Number: 1760
Packing Group: II
IMO
Shipping Name: CORROSIVE LIQUID, N.O.S.
Hazard Class: 8
UN Number: 1760
Packing Group: II
RID/ADR
Shipping Name: CORROSIVE LIQUID, N.O.S.
Hazard Class: 8
UN Number: 1760
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 1794-24-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1794-24-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1794-24-7 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  双(二乙基胺基)磷酰氯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.18h， 以35%的产率得到WM-IV-isobu-OP(O)(OEt2)2
  参考文献：
  名称：

  WO2007/67333

  摘要：

  公开号：
• 作为产物：
  描述：

  ethyl N,N'-tetraethyldiamidophosphite 在 氯乙酸乙酯 作用下， 反应 1.5h， 以82%的产率得到双(二乙基胺基)磷酰氯
  参考文献：
  名称：

  摘要：

  Reactions of ethyl and tert-butyl phosphorodiamidites with chloroacetone, bromoacetone, and alpha-chloroethyl acetate were studied. The reaction pathway is determined by the structure of the intermediate quasiphosphonium compound responsible for the formation of the Arbuzov product as well as for the occurrence of the amonalous reaction yielding vinyl phosphate.

  DOI：

  10.1023/a:1023397330794

文献信息

• CHEMISTRY OF N-PHOSPHORYLATED NITROGEN MUSTARDS: THE EFFECT OF A SECOND NITROGEN SUBSTITUENT AT PHOSPHORUS ON THE STABILITY OF THE SYSTEM
  作者：Huijie Wan、Tomasz A. Modro

  DOI：10.1080/10426509608029648

  日期：1996.1.1

  Abstract Methyl N,N-diethyl-N'N'-bis(2-chloroethyl)phosphoramidate was prepared as a precursor for the corresponding phosphordiamidate anion, a model for the phosphoramidate mustard, biologically active degradation product of cyclophosphamide drug. Demethylation of the precursor led to a highly unstable ion which underwent spontaneous fragmentation. In the absence of an external nucleophile, the ion

  摘要 制备了 N,N-二乙基-N'N'-双（2-氯乙基）磷酰胺酸甲酯作为相应的二酰胺磷阴离子的前体，氨基磷酸芥的模型，环磷酰胺药物的生物活性降解产物。前体的去甲基化导致高度不稳定的离子发生自发分裂。在没有外部亲核试剂的情况下，离子分解产生偏氨基磷酸酯和 N-取代的乙烯亚胺作为主要中间体。在吡啶的存在下，两个吡啶发生双烷基化，产生双 [2-(N-吡啶并)乙基]胺二甲基化，此外还有一些 1,3,2-氧氮杂膦衍生物，通过竞争性 1,5-去甲基化阴离子的环化。在苯硫酚/三乙胺存在下孵育前体导致两个平行的亲核置换：(i) O-去甲基化，然后是两个苯硫酚分子的双烷基化，以及一些 1,5-环化；(ii) 初始直接分配...
• Tetrabutylammonium tetra (tert-butyl alcohol) coordinated fluoride-an efficient reagent for the synthesis of fluorine derivatives of phosphorus(V) compounds
  作者：Hemendra K. Gupta、Deepak Pardasani、Avik Mazumder、Ajay Kumar Purohit、Devendra K. Dubey

  DOI：10.1016/j.tetlet.2009.03.151

  日期：2009.6

  Direct conversion of phosphorus(V) chlorides to the corresponding phosphorus(V) fluorides was achieved using a solid reagent, tetrabutylammonium tetra (tert-butyl alcohol) coordinated fluoride. The phosphorus(V) fluorides were directly synthesized and efficiently isolated in very good yields.

  使用固体试剂四（叔丁醇）配位的四丁基铵可实现氯化磷（V）直接转化为相应的氟化磷（V）。直接合成了氟（V）氟化物，并以非常高的收率有效地进行了分离。
• The Hydrolysis of Disubstituted Alkyl Phosphorochloridates and <i>N</i>,<i>N</i>,<i>N</i>′,<i>N</i>′-Tetra-stibstituted Phosphorodiamidic Chlorides in Water and Deuterium Oxide: Heat Capacity of Activation and Kinetic Solvent Isotope Effects
  作者：E. C. F. Ko、R. E. Robertson

  DOI：10.1139/v73-090

  日期：1973.2.15

  alkyl-phosphorochloridates, where the alkyl group is ethylisopropyl and n-propyl; for tetra-methyl and tetra-ethyl phosphorodiamidic chlorides; the di-n-propyl and di-isopropyl analog, the di(isopropylmethylcarbinyl)phosphorochloridate and the tetra-ethylthiophosphorodiamidic chloride. These compounds have a potential relationship to compounds used as insecticides and as polymers. The mechanism of reaction

  已经确定了三种烷基-磷酰氯的拟热力学参数ΔH≠、ΔS≠和ΔCp≠以及动力学溶剂同位素效应，其中烷基为乙基异丙基和正丙基；四甲基和四乙基磷酰二胺氯化物；二正丙基和二异丙基类似物、二(异丙基甲基羰基)磷酰氯和四乙基硫代磷酰二酰氯。这些化合物与用作杀虫剂和聚合物的化合物有潜在关系。在这些数据的基础上讨论了反应机理。
• The Reaction of Alcohols with Hexamethylphosphoric Triamide
  作者：Seiji Arimatsu、Ryohei Yamaguchi、Mituyosi Kawanisi

  DOI：10.1246/bcsj.47.1693

  日期：1974.7

  The thermal treatment of 4-homoadamantanol and bicyclo[3.3.1]nonanols with hexamethylphosphoric triamide (HMPT) gave the corresponding olefins in moderate yields. The application of this dehydration method to a system in which olefin formation was regarded as difficult or impossible stereochemically led to various types of reactions, i.e., reduction, substitution, and phosphorodiamidation. Upon being

  4-高金刚烷醇和双环[3.3.1]壬醇与六甲基磷酰三胺（HMPT）的热处理以中等产率得到相应的烯烃。将该脱水方法应用于其中烯烃形成被认为在立体化学上困难或不可能的体系中导致了各种类型的反应，即还原、取代和磷酸二酰胺化。在 HMPT 中加热后，2-金刚烷醇得到 2-金刚烷基四甲基磷二酰胺，而 1-金刚烷醇通过 1-金刚烷基四甲基磷二酰胺转化为金刚烷。在烯丙醇或苄醇的情况下，获得二甲氨基取代的化合物。HMPT 量的减少促进了醚的形成，而二二苯甲醚仅由二苯甲醇产生。
• Concerted Pathway to the Mechanism of the Anilinolysis of Bis(N,N-diethylamino)phosphinic Chloride in Acetonitrile
  作者：Hasi Rani Barai

  DOI：10.1071/ch16202

  日期：——

  The kinetics of the nucleophilic substitution reactions of bis(N,N-diethylamino)phosphinic chloride with substituted anilines (XC6H4NH2) and deuterated anilines (XC6H4ND2) are investigated in MeCN at 65.0°C. The deuterium kinetic isotope effects (DKIEs) are secondary inverse (kH/kD < 1: 0.706–0.947) and the magnitudes of the secondary inverse DKIEs (kH/kD) increase constantly as the nucleophiles are

  在65.0°C的MeCN中研究了双（N，N-二乙氨基）次膦酰氯与取代的苯胺（XC 6 H 4 NH 2）和氘代苯胺（XC 6 H 4 ND 2）的亲核取代反应的动力学。氘的动力学同位素效应（DKIEs）是次要的逆（k H / k D  <1：0.706-0.947），并且随着亲核试剂从弱碱性变成弱的，次要的逆DKIEs（k H / k D）的大小不断增加。强烈的基本苯胺。选择性参数的大小为ρX（H）  = -6.34，和β X（H）  = 2.24与取代的苯胺和ρ X（d）  = -6.13和β X（d）  = 2.17用氘代苯胺。基于具有取代基X的k H / k D值，提出了一种涉及主要的背面攻击的协同S N 2机制。