异腈甲基磷酸二乙酯 | 41003-94-5

• 物质功能分类: 化学试剂 - 有机试剂 - 氰酸酯/异氰酸酯
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 中文名称: 异腈甲基磷酸二乙酯
• 中文别名: 异腈甲基膦酸二乙酯
• 英文名称: diethyl isocyanomethylphosphonate
• 英文别名: diethyl α-isocyanomethylphosphonate；1-[ethoxy(isocyanomethyl)phosphoryl]oxyethane
• CAS: 41003-94-5
• 化学式: C₆H₁₂NO₃P
• mdl: MFCD00042951
• 分子量: 177.14
• InChiKey: ICURVXBGGDVHDT-UHFFFAOYSA-N

物化性质

• 沸点：
  84-87 °C0.1 mm Hg(lit.)
• 密度：
  1.105 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2931900090
• 危险标志：
  GHS07
• 危险性描述：
  H302 + H312 + H332,H315,H319,H335
• 危险性防范说明：
  P261,P280,P305 + P351 + P338
• 储存条件：
  请将密封存储在阴凉干燥的环境中。

SDS

Name:	Diethyl isocyanomethylphosphonate Material Safety Data Sheet
Synonym:	Isocyanomethylphosphononic acid diethyleste
CAS:	41003-94-5

Section 1 - Chemical Product MSDS Name:Diethyl isocyanomethylphosphonate Material Safety Data Sheet
Synonym:Isocyanomethylphosphononic acid diethyleste

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
41003-94-5	Diethyl isocyanomethylphosphonate		unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.Light sensitive.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
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 water spray, dry chemical, carbon dioxide, or chemical foam.

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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:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Keep refrigerated. (Store below 4C/39F.) Store in a tightly closed container. Store in a dry area.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 41003-94-5: 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: colorless to light yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 84 - 87 deg C @0.1mmHg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: > 110 deg C (> 230.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.105
Molecular Formula: C6H12NO3P
Molecular Weight: 177.14

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, light.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, phosphine, carbon monoxide, oxides of phosphorus, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 41003-94-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Diethyl isocyanomethylphosphonate - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Other No information available.

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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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37 Wear suitable protective clothing and
gloves.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 41003-94-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 41003-94-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 41003-94-5 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：

  异腈甲基磷酸二乙酯 在 potassium tert-butylate 、 二异丙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-3β-Acetoxy-17-<(diethylphosphono)isocyanomethylene>androst-5-ene
  参考文献：
  名称：

  Chemistry of N,P-acetals: application to the synthesis of 20-ketosteroids

  摘要：

  A series of new derivatives of alpha-(isocyanomethyl)phosphonates (6a,b,c and 9) is described, which are formed by methylation of (E)-17-[(diethylphosphono)isocyanomethylene] steroids 5a,b,c and 17-beta-[(diethylphosphono)isocyanomethyl] steroid 8. It proved possible to hydrolyze these compounds under relatively mild conditions to 20-ketosteroids 7a,b,c and 10, showing for the first time that geminal N- and P-substituted carbon compounds do react as N,P-acetals.

  DOI：

  10.1021/jo00034a012
• 作为产物：
  描述：

  二乙基(甲酰氨基甲基)膦酸酯 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 生成 异腈甲基磷酸二乙酯
  参考文献：
  名称：

  1,5-二取代四唑作为 PD-1/PD-L1 拮抗剂

  摘要：

  通过单克隆抗体（例如pembrolizumab (Keytruda)）靶向抑制性免疫检查点蛋白 PD-1/PD-L1 复合物的创新方法，癌症生存和治疗的进展发生了显着的转变。虽然到 2021 年将产生 172 亿美元的收入，但这些发展的真正意义在于它们能够改善癌症患者的治疗效果。尽管单克隆抗体在抑制 PD-1/PD-L1 信号通路方面已被证明有效，但它们面临着重大挑战，包括有限的响应率、高生产成本、缺乏口服生物利用度以及可能导致免疫相关不良反应的半衰期延长。影响。一种有前途的替代方法涉及使用小分子作为 PD-1/PD-L1 拮抗剂来刺激 PD-L1 二聚化。然而，这些分子的确切作用机制仍不完全清楚，这给它们的发展带来了挑战。在此背景下，我们的研究重点是创建基于Ugi四唑四组分反应（UT-4CR）的新型支架，以开发PD-L1的低分子量抑制剂。采用基于结构的方法，我们使用联苯乙烯基异氰化物合成了一系列小化合物，从而发现了

  DOI：

  10.1039/d3md00746d

文献信息

• SULFONAMIDE, SULFAMATE, AND SULFAMOTHIOATE DERIVATIVES
  申请人：Wang Zhong

  公开号：US20120077814A1

  公开（公告）日：2012-03-29

  The disclosure provides biologically active compounds of formula (I): and pharmaceutically acceptable salts thereof, compositions containing these compounds, and methods of using these compounds in a variety applications, such as treatment of diseases or disorders associated with E1 type activating enzymes, and with Nedd8 activating enzyme (NAE) in particular.

  该披露提供了化学式(I)的生物活性化合物及其药用盐，含有这些化合物的组合物，以及在各种应用中使用这些化合物的方法，例如用于治疗与E1型激活酶相关的疾病或紊乱，特别是与Nedd8激活酶(NAE)相关的疾病或紊乱。
• Efficient Assembly of Iminodicarboxamides by a “Truly” Four-Component Reaction
  作者：Kareem Khoury、Mantosh K. Sinha、Tadamichi Nagashima、Eberhardt Herdtweck、Alexander Dömling

  DOI：10.1002/anie.201205366

  日期：2012.10.8

  Mix and match: Similar to a galaxy consisting of millions of stars, a multicomponent reaction (MCR) system can result in millions of compounds. The MCR of α‐amino acids, oxo components, isocyanides, and amines leads to numerous and diverse compounds, thus having enormous potential for drug discovery or catalyst screening.

  混合搭配：类似于由数百万颗恒星组成的星系，多组分反应 (MCR) 系统可以产生数百万种化合物。α-氨基酸、含氧组分、异氰化物和胺的 MCR 导致产生大量不同的化合物，因此在药物发现或催化剂筛选方面具有巨大的潜力。
• Antiaromatische Verbindungen; 28.¹Eine Synthese von Pyrrol-Derivaten aus Tri-<i>tert</i>-butylazet und Isonitrilen oder Kohlenmonoxid
  作者：Udo Hees、Jürgen Schneider、Oliver Wagner、Manfred Regitz

  DOI：10.1055/s-1990-27029

  日期：——

  Antiaromatic Compounds; 28.1. A Synthesis of Pyrrole Derivatives from Tri-tert-butylazete and Isonitriles or Carbon Monoxide The kinetically stabilized azete 4 reacts with isonitriles 5 in a sequence of [4 + 1] cycloaddition and ring-opening steps to yield 2- and 3-imino substituted 2H- and 3H-pyrrole derivatives 8,9. The α-methylene isonitriles 10 react analogously, but the formation of 2- and 3-iminopyrroles is still followed by an [1,5]-shift which leads to 2- and 3-aminopyrroles 13,14. With carbon monoxide the azete 4 is transformed into the 2H-pyrrole-2-one and 3H-pyrrole-3-one 18 and 19.

  反芳香性化合物；28.1. 从三叔丁基叠氮和异氰或一氧化碳合成吡咯衍生物 动力学稳定的叠氮4与异氰5在[4 + 1]环加成和环开环步骤序列中反应，产生2-和3-亚氨基取代的2H-和3H-吡咯衍生物8,9。α-甲基异氰10以类似的方式反应，但2-和3-亚氨基吡咯的形成之后仍会通过[1,5]迁移，导致生成2-和3-氨基吡咯13,14。叠氮4与一氧化碳反应，转化为2H-吡咯-2-酮和3H-吡咯-3-酮18和19。
• Synthesis and Biological Activities of the Antibiotic B 371 and its Analogs
  作者：Inga Hoppe、Ulrich Schöllkopf

  DOI：10.1002/jlac.198419840317

  日期：1984.3.12

  is described as well as the syntheses of a series of structural analogs of type 4. The antimicrobial in vitro activity of these vinyl isocyanides, substituted in β-position either by an indole derivative or by an aryl or 2-thienyl group, was tested against Escherichia Coli, Bacillus subtilis, and Mucor muhei TÜ 284 (Table 1). Some of the compounds 4 display higher activity than the naturally occurring

  描述了标题化合物1的合成以及一系列类型4的结构类似物的合成。测试了这些乙烯基异氰酸酯在β位置被吲哚衍生物或芳基或2-噻吩基取代后的体外抗菌活性，针对大肠杆菌，枯草芽孢杆菌和Mucor muheiTÜ284（表1）进行了测试。一些化合物4显示出比天然存在的母体化合物1更高的活性。-各种5型的2-异氰基丙烯酸烷基酯被包括在生物学测试中。其中一些显示出极高的抗菌活性（表2）。将异氰基转化为甲酰胺基（4 6）后，其生物学活性丧失。
• Intramolecular Imidoylative Heck Reaction: Synthesis of Cyclic Ketoimines from Functionalized Isocyanide
  作者：Jian Wang、Shi Tang、Qiang Zhu

  DOI：10.1021/acs.orglett.6b01174

  日期：2016.7.1

  Efficient access to five- to seven-membered cyclic ketoimines, through palladium-catalyzed intramolecular imidoylative Heck reaction of alkene-containing isocyanides, has been developed. Consecutive isocyanide and alkene insertion into aryl or alkyl Pd(II) intermediates takes place in this process. No byproduct derived from monoinsertion or reversed sequence is detected.

  已经开发出通过钯催化含烯烃异氰酸酯的分子内酰亚胺化Heck反应，可以有效地获得五元至七元环状酮亚胺。在此过程中，异氰酸酯和烯烃连续插入芳基或烷基Pd（II）中间体中。没有检测到源自单插入或反向序列的副产物。

表征谱图