亚磷酸三新戊酯 | 14540-52-4

• 物质功能分类: 有机原料 - 无机酸酯
• 分子结构分类: 有机化合物 - 有机磷化合物 - 亚磷酸三烷基酯
• 中文名称: 亚磷酸三新戊酯
• 英文名称: trineopentyl phosphite
• 英文别名: Trineopentylphosphit；tris(2,2-dimethylpropyl) phosphite
• CAS: 14540-52-4
• 化学式: C₁₅H₃₃O₃P
• 分子量: 292.399
• InChiKey: VEKIRWDIEAVDHT-UHFFFAOYSA-N

物化性质

• 熔点：
  55-57°C
• 沸点：
  80°C 0,15mm

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2920901900

SDS

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Section 1: Product Identification
Chemical Name: Tri-neo-pentylphosphite, min.90%
CAS Registry Number: 14540-52-4
Formula: [(CH3)3CCH2O]3P
EINECS Number: none
Chemical Family: organophosphorus compound
Synonym: Trineopentoxyphosphine, phosphorous acid, tri-neo-pentyl ester, phosphorus trineopentoxide.

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title Compound 14540-52-4 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Solid may be irritating to skin, eyes and respiratory tract. May be harmful if swallowed.
Primary Routes of Exposure: Ingestion, inhalation
Eye Contact: May cause slight to mild irritation of the eyes
Skin Contact: May cause slight to mild irritation of the skin.
Inhalation: Dust may be irritating to the nose, mucous membranes and respiratory tract.
No specific information is available on the physiological effects of ingestion. May cause vomiting and diarrhea.
Ingestion:
Acute Health Affects: May be irritating to skin, eyes and respiratory tract.
Chronic Health Affects: No information available on long-term chronic effects.
NTP: No
IARC: No
OSHA: No

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SECTION 4: First Aid Measures
Immediately flush the eyes with copious amounts of water for at least 10-15 minutes. A victim may need
Eye Exposure:
assistance in keeping their eye lids open. Get immediate medical attention.
Wash the affected area with water. Remove contaminated clothes if necessary. Seek medical assistance if
Skin Exposure:
irritation persists.
Remove the victim to fresh air. Closely monitor the victim for signs of respiratory problems, such as difficulty
Inhalation:
in breathing, coughing, wheezing, or pain. In such cases seek immediate medical assistance.
Seek medical attention immediately. Keep the victim calm. Give the victim water (only if conscious). Induce
Ingestion:
vomiting only if directed by medical personnel.

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SECTION 5: Fire Fighting Measures
Flash Point: not applicable
Autoignition Temperature: no data
Explosion Limits: no data
Extinguishing Medium: dry chemical, carbon dioxide, or foam.
Fire fighters should be equipped with a NIOSH approved positive pressure self-contained breathing apparatus
Special Fire Fighting Procedures:
and full protective clothing.
Hazardous Combustion and If involved in a fire this material may emit toxic organic fumes, carbon monoxide, and phosphorous oxides.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards.

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SECTION 6: Accidental Release Measures
Small spills can be mixed with vermiculite, sodium carbonate or other suitable non combustible adsorbent and
Spill and Leak Procedures:
swept up.

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SECTION 7: Handling and Storage
Store in a cool, dry, well-ventilated area away from heat and direct sunlight. This product may react slowly with
Handling and Storage:
air and moisture. Transfer material under an inert atmosphere of dry nitrogen or argon.

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SECTION 8: Exposure Controls and Personal Protection
Eye Protection: Always wear approved safety glasses when handling a chemical substance in the laboratory.
Skin Protection: Wear protective clothing and gloves. Consult with glove manufacturer to determine the proper type of glove.
Ventilation: Material may form a fine dust. Work with this product in a well-ventilated area, preferably a fume hood.
If ventilation is not available a respirator should be worn. The use of respirators requires a Respirator
Respirator:
Protection Program to be in compliance with 29 CFR 1910.134
Ventilation: Material may form a fine dust. Work with this product in a well-ventilated area, preferably a fume hood.
Additional Protection: No additional protection required.

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SECTION 9: Physical and Chemical Properties
Color and Form: white xtl.
Molecular Weight: 292.4
Melting Point: 55-57°
Boiling Point: 80°C /0.15 mm
Vapor Pressure: no data
Specific Gravity: no data
Odor: unpleasant odor
Solubility in Water: insoluble

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SECTION 10: Stability and Reactivity
Stability: air sensitive
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: prolonged contact with air or moisture, especially at elevated temperature.
Incompatibility: oxygen, oxidizing agents, sulfur, and halogens
Decomposition Products: carbon dioxide, carbon monoxide, organic fumes, dineopentylphosphonate, and phosphorus pentoxide.

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SECTION 11: Toxicological Information
RTECS Data: No information available in the RTECS files.
Carcinogenic Effects: No data available
Mutagenic Effects: No data available
Tetratogenic Effects: No data available

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SECTION 12: Ecological Information
Ecological Information: No information available

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SECTION 13: Disposal Considerations
Disposal: Dispose of according to federal, state, and local regulations.

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SECTION 14: Transportation
Shipping Name (CFR): Non-hazardous
Hazard Class (CFR): NA
Additional Hazard Class (CFR): NA
Packaging Group (CFR): NA
UN ID Number (CFR): NA
Shipping Name (IATA): Non-hazardous
Hazard Class (IATA): NA
Additional Hazard Class (IATA): NA
Packaging Group (IATA): NA
UN ID Number (IATA): NA

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SECTION 15: Regulatory Information
TSCA: Not listed in the TSCA inventory.
SARA (Title 313): Title compound not listed.
Second Ingredient: none

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  亚磷酸三新戊酯 在 碘 作用下， 以 various solvent(s) 为溶剂， 生成 iodo-neopentoxyphosphonium salt
  参考文献：
  名称：

  Michalski, Jan; Pakulski, Marek; Skowronska, Aleksandra, Journal of the Chemical Society. Perkin transactions I, 1980, p. 833 - 836

  摘要：

  DOI：
• 作为产物：
  描述：

  新戊醇 在 吡啶 、 三氯化磷 作用下， 以 Petroleum ether 为溶剂， 反应 0.67h， 以76%的产率得到亚磷酸三新戊酯
  参考文献：
  名称：

  有机膦离子均裂水解过程中碳氢化合物和磷酸三酯的形成：有机膦酸盐生物降解的替代模型

  摘要：

  用碱和有机过氧化物处理有机三五氧鏻三氟甲磺酸盐会导致碳磷 (CP) 键断裂。均裂水解的产物是碳氢化合物和磷酸三新戊酯。有机鏻离子仅与碱反应导致氧至磷 (OP) 键断裂，而完全没有 CP 键断裂。在均裂水解过程中五共价膦酰基自由基的可能中间体为在有机膦酸盐生物降解过程中观察到的 CP 键裂解的替代机械配方提供了基础。该配方的独特之处在于它预测无机磷酸盐是微生物介导的 CP 键裂解的直接含磷产物

  DOI：

  10.1021/ja00006a049
• 作为试剂：
  描述：

  三丁基,三丁酯 、 bis(diethylphosphoryl)disulfide 在 亚磷酸三新戊酯 作用下， 以 二氯甲烷 为溶剂， 生成 硫代焦磷酸四乙酯 、 治螟磷 、 硫代磷酸,S-(1,1-二甲基乙基)O,O-二乙酯 、
  参考文献：
  名称：

  Krawczyk, Ewa; Skowronska, Aleksandra; Michalski, Jan, Journal of the Chemical Society. Perkin transactions I, 1994, # 1, p. 89 - 100

  摘要：

  DOI：

文献信息

• Studies on the interaction of phosphine selenides and their structural analogues wth dihalogens and sulfuryl chloride
  作者：Ewa Krawczyk、Aleksandra Skowrońska、Jan Michalski

  DOI：10.1039/b207019g

  日期：——

  tris(dimethylamino)phosphine selenide, esters of selenophosphoric acid, and esters of selenophosphonic acid react with dihalogens and sulfuryl chloride to form halogenoselenophosphonium salts (P–SeX)+X−. The latter undergo deselenization via ligand exchange to form phosphonium salts (P–X)+X− and elemental selenium. The stability of these salts depends on the substituents at the phosphorus atom and the type of counter

  膦硒化物， 三（二甲氨基）膦硒化物， 酯类 的 硒磷酸， 和 酯类 的 硒代膦酸 与二卤素反应并 硫酰氯到形式halogenoselenophosphonium盐（P-性别）+ X - 。后者通过 配体交换形式鏻盐（P-X）+ X -和元素硒。这些盐的稳定性取决于磷原子上的取代基和抗衡离子的类型。salts盐可能与相应的equilibrium盐处于平衡状态磷烷，这证明了 酯类含有邻亚苯基配体。salts盐的结构，磷烷 和其他磷化合物的支持 31 P NMR光谱数据和电导率。其他证据来自卤代硒代phosph盐与环己烯。
• Quasiphosphonium intermediates. Part 3. Preparation, structure, and reactivity of alkoxyphosphonium halides in the reactions of neopentyl diphenylphosphinite, dineopentyl phenylphosphonite, and trineopentyl phosphite with halogenomethanes and the effect of phenoxy-substituents on the mechanism of alkyl–oxygen fission in Michaelis–Arbuzov reactions
  作者：Harry R. Hudson、Aloysius Kow、John C. Roberts

  DOI：10.1039/p29830001363

  日期：——

  of the phosphonium halide ion-pair with SN2-type fission of the alkyl–oxygen bond. Rates for chloride, bromide, and iodide are similar. In a more ionising medium (deuterioacetonitrile) dissociation leads to stabilisation of the intermediates and to deviation from first-order decomposition. Previously determined X-ray diffraction data for the bromides, together with relative rates of decomposition in

  新戊基二苯基次膦酸酯与氯甲烷，溴甲烷或碘甲烷的反应以及二戊基苯基次膦酸酯与溴甲烷或碘甲烷的反应产生结晶的烷氧基phosph卤化物。在氘代氯仿中，这些中间体通过一阶过程分解，该过程涉及速率确定卤化phospho离子对的崩溃以及烷基-氧键的S N 2型裂变。氯化物，溴化物和碘化物的比率相似。在离子化程度更高的介质（氘代乙腈）中，离解可导致中间体稳定并偏离一级分解。先前确定的溴化物X射线衍射数据，以及一系列Ph中间体的氘代氯仿中的相对分解速率n（RO） 3– n [MeX] -（n= 0、1或2）表明，烷氧基phosph中间体的稳定性和反应性很大程度上取决于配体的诱导效应而不是介晶效应。在某些情况下，磷上苯氧基取代基的存在可能导致烷基-氧键发生S N 1型裂变。
• Phosphonium ion fragmentation relevant to organophosphonate biodegradation
  作者：L. Z. Avila、J. W. Frost

  DOI：10.1021/ja00206a058

  日期：1989.11

  degradation of organophosphonates 1 via carbon to phosphorus (C-P) bond cleavage has prompted a rapid expansion in chemical literature relevant to the biodegradation. However, the chemistry of organophosphonates under reducing conditions, particularly in regard to C-P bond cleavage, is still largely unknown. This report examines the single-electron and hydride reduction of organophosphonates and organot

  通过碳到磷 (CP) 键裂解对有机膦酸酯 1 的微生物降解促使与生物降解相关的化学文献迅速扩展。然而，有机膦酸酯在还原条件下的化学性质，特别是关于 CP 键的裂解，仍然很大程度上未知。本报告研究了在结构上与有机膦离子 2（方案 1）相关的有机膦酸盐和有机三五氧鏻三氟甲磺酸盐 4a-e（表 1）的单电子和氢化物还原。
• Process for preparing unsymmetrical biaryls and alkylated aromatic compounds from arylnitriles
  申请人：DSM N.V.

  公开号：US20030100760A1

  公开（公告）日：2003-05-29

  Methods are provided for the construction of unsymmetrical biaryl compounds and alkylated aromatic compounds from arylnitriles using a nickel or palladium catalyzed coupling in which the catalyst has at least one phosphine or phosphite ligand.

  提供了一种方法，可以利用镍或钯催化的偶联反应，从芳基腈中构建非对称联苯化合物和烷基化芳香化合物，其中催化剂至少具有一个膦或膦酯配体。
• Phase-Programmed Nanofabrication: Effect of Organophosphite Precursor Reactivity on the Evolution of Nickel and Nickel Phosphide Nanocrystals
  作者：Himashi P. Andaraarachchi、Michelle J. Thompson、Miles A. White、Hua-Jun Fan、Javier Vela

  DOI：10.1021/acs.chemmater.5b03506

  日期：2015.12.8

  chloride or acetate to form nickel phosphides increases in the order P(OMe)3 < P(OEt)3 < P(OnBu)3 < P(OCH2tBu)3 < P(OiPr)3 < P(OPh)3. Some organophosphites, such as P(OMe)3 or P(OiPr)3, transiently form zerovalent, metallic nickel, while this is the only persistent product observed with the bulky organophosphite P(O-2,4-tBu2C6H4)3. We expect that these results will alleviate the need for time-consuming

  更好地理解分子前体的化学性质对于获得更可预测和可重现的纳米晶体制剂很有用。最近，引入了一种有效的方法，该方法包括微调所用合成分子前体的化学反应性，同时保持所有其他反应条件不变。使用磷化镍作为研究平台，我们研究了一系列可商购获得的有机亚磷酸酯前体（P（OR）3）的化学结构和反应性，R ＝烷基或芳基）改变金属和金属磷化物纳米晶体的制备。有机亚磷酸酯是Pnictide合成工具箱的多功能补充品，很好地补充了其他可用的前体，例如元素磷或三辛基膦（TOP）。实验和计算数据表明，不同的有机亚磷酸酯前体有选择地产生Ni，Ni 12 P 5和Ni 2P和这些阶段随着时间的流逝通过不同的机械途径发展。根据我们的观察，我们建议形成磷化镍需要将有机亚磷酸酯与镍前体进行配位，然后进行分子内重排。我们还提出，金属镍的形成涉及通过不配位的有机亚磷酸酯还原外球。这两个独立的途径得到了以下事实的支持：预先形成的Ni纳米晶体