4-膦酰丁酸三乙酯 | 2327-69-7

• 物质功能分类: 有机原料 - 有机膦化合物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 4-膦酰丁酸三乙酯
• 中文别名: 4-膦酰丁酸三乙脂
• 英文名称: ethyl 4-(diethoxyphosphoryl)butanoate
• 英文别名: ethyl 4-(diethoxyphosphoryl)butyrate；triethyl 4-(phosphono)butyrate；triethyl 4-phosphonobutyrate；4-diethoxyphosphoryl-butyric acid ethyl ester；4-Diaethoxyphosphoryl-buttersaeure-aethylester；4-(diethoxyphosphinyl)-butanoic acid, ethyl ester；ethyl 4-diethoxyphosphorylbutanoate
• CAS: 2327-69-7
• 化学式: C₁₀H₂₁O₅P
• mdl: MFCD00015168
• 分子量: 252.247
• InChiKey: FYESTJSRASJZOY-UHFFFAOYSA-N

物化性质

• 沸点：
  133-135 °C (0.4 mmHg)
• 密度：
  1.1069 g/cm3
• 闪点：
  117-119°C/0.4mm
• 稳定性/保质期：
  避免让氧化物直接接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2931900090
• 危险性防范说明：
  P280,P302+P352,P305+P351+P338,P321,P332+P313,P362
• 危险性描述：
  H315,H319
• 储存条件：
  请将容器密封后存放在干燥、阴凉的地方，并使用紧闭的容器储存。

SDS

Name:	Triethyl 4-Phosphonobutyrate Material Safety Data Sheet
Synonym:	Diethyl 3-(Ethoxycarbonyl)Propylphosphonate
CAS:	2327-69-7

Section 1 - Chemical Product MSDS Name:Triethyl 4-Phosphonobutyrate Material Safety Data Sheet
Synonym:Diethyl 3-(Ethoxycarbonyl)Propylphosphonate

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2327-69-7	Triethyl 4-Phosphonobutyrate	ca. 100	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.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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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.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. 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. Do NOT use mouth-to-mouth resuscitation.
Notes to Physician:
Treat symptomatically and supportively.

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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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use extinguishing media most appropriate for the surrounding fire.

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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. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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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# 2327-69-7: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 133 - 135 deg C @ .40mmHg
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:
Molecular Formula: C10H21O5P
Molecular Weight: 252.24

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of phosphorus, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2327-69-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Triethyl 4-Phosphonobutyrate - 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
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 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 2327-69-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 2327-69-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2327-69-7 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

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  4-(二乙基膦)丁酸	γ-diethoxyphosphorylbutyric acid	38694-48-3	C8H17O5P	224.194
  ——	ethyl 4-(P-chloro-P-ethoxyphosphinoyl)butanoate	93938-97-7	C8H16ClO4P	242.639
  ——	diethyl {3-[3-(bis{3-[4-(diethyloxyphosphoryl)butyrylamino]propyl}amino)propylcarbamoyl]propyl}phosphonate	331463-37-7	C33H69N4O12P3	806.852
  ——	diethyl {3-[2-(bis{2-[4-(diethyloxyphosphoryl)butyrylamino]ethyl}amino)ethylcarbamoyl]propyl}phosphonate	331463-35-5	C30H63N4O12P3	764.771

反应信息

• 作为反应物：
  描述：

  4-膦酰丁酸三乙酯 在 sodium hydroxide 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (+/-)-Diethyl 3-(carboxy)pentadecylphosphonate
  参考文献：
  名称：

  The discovery of 3-(N-alkyl)aminopropylphosphonic acids as potent S1P receptor agonists

  摘要：

  3-(N-Alkyl)aminopropylphosphonic acids are potent agonists of four of the five known sphingosine-1-phosphate (S1P) receptor subtypes. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.069
• 作为产物：
  描述：

  4-溴丁酸乙酯 、 亚磷酸二乙酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 4-膦酰丁酸三乙酯
  参考文献：
  名称：

  作为抗疟药和抗菌剂的磷霉素替代物的酰氧基甲基和烷氧基羰基氧基甲基前药

  摘要：

  Fosmidomycin 是一种天然抗生素，具有有效的 IspC（DXR，1-脱氧-d-木酮糖-5-磷酸还原异构酶）抑制活性。这种酶催化非甲羟戊酸类异戊二烯生物合成途径的第一个关键步骤，这在大多数细菌（包括鲍曼不动杆菌和结核分枝杆菌）和顶复门寄生虫（包括疟原虫寄生虫）中必不可少。主要由于其高极性，磷米霉素表现出次优的药代动力学特性。此外，fosmidomycin 对鲍曼不动杆菌和结核分枝杆菌无活性由于其无法穿透细菌细胞壁。暂时将膦酸酯部分作为前药进行掩蔽有可能解决这两个问题。我们报告了磷胺霉素替代物的酰氧基甲基和烷氧基羰基氧基甲基膦酸酯前药系列的扩展。前药前体是根据电子、亲脂性和铁载体特性设计的。该研究导致发现了分别具有两位数纳摩尔和亚微摩尔 IC 50值的衍生物，用于对抗恶性疟原虫和鲍曼不动杆菌。

  DOI：

  10.1016/j.ejmech.2022.114924

文献信息

• [EN] NOVEL CYCLIC BENZIMIDAZOLE DERIVATIVES USEFUL ANTI-DIABETIC AGENTS<br/>[FR] NOUVEAUX AGENTS ANTIDIABÉTIQUES UTILES AVEC DES DÉRIVÉS DE BENZIMIDAZOLE CYCLIQUES
  申请人：MERCK SHARP & DOHME

  公开号：WO2010051206A1

  公开（公告）日：2010-05-06

  Novel compounds of the structural formula (I) are activators of AMP-protein kinase and are useful in the treatment, prevention and suppression of diseases mediated by the AMPK- activated protein kinase. The compounds of the present invention are useful in the treatment of Type 2 diabetes, hyperglycemia, metabolic syndrome, obesity, hypercholesterolemia, and hypertension.

  结构式（I）的新化合物是AMP-蛋白激酶的激活剂，并且在治疗、预防和抑制由AMPK激活的蛋白激酶介导的疾病方面非常有用。本发明的化合物在治疗2型糖尿病、高血糖、代谢综合征、肥胖、高胆固醇血症和高血压方面非常有用。
• HYDROXYL PURINE COMPOUNDS AND USE THEREOF
  申请人：GUANGDONG ZHONGSHENG PHARMACEUTICAL CO., LTD

  公开号：US20180148451A1

  公开（公告）日：2018-05-31

  Disclosed are a series of hydroxyl purine compounds and the use thereof as PDE2 or TNFα inhibitors, in particular, the compounds as shown in formula (I), or tautomers or pharmaceutically acceptable salts thereof.

  揭示了一系列的羟基嘌呤化合物及其作为PDE2或TNFα抑制剂的用途，特别是如公式(I)所示的化合物，或其互变异构体或药用可接受的盐。
• Cyclohexylene Reactive Mesogens and Their Applications
  申请人：Farrand Louise Diane

  公开号：US20100103366A1

  公开（公告）日：2010-04-29

  The invention relates to new cyclohexylene reactive mesogens (RM), polymers derived thereof, liquid crystal (LC) media comprising them, and the use of the compounds, polymers and liquid crystalline media in optical, electrooptical, electronic, semiconducting or luminescent components or devices, in decorative, security, cosmetic or diagnostic applications, especially in the polymer stabilised blue phase.

  该发明涉及新的环己烯基反应性向列体（RM），由此衍生的聚合物，包含它们的液晶（LC）介质，以及在光学、电光学、电子、半导体或发光元件或设备中使用这些化合物、聚合物和液晶介质，在装饰、安全、化妆品或诊断应用中的使用，特别是在聚合物稳定的蓝相中的使用。
• Phosphate derivatives as immunoregulatory agents
  申请人：——

  公开号：US20020091105A1

  公开（公告）日：2002-07-11

  Immunoregulatory compounds are disclosed of the formula: 1 and 2 as well as the pharmaceutically acceptable salts and hydrates thereof, are disclosed. The compounds are useful for treating immune mediated diseases and conditions, such as bone marrow, organ and tissue transplant rejection. Pharmaceutical compositions and methods of use are included.

  揭示了具有以下式子的免疫调节化合物：1和2以及其药用盐和水合物。这些化合物可用于治疗免疫介导的疾病和状况，如骨髓、器官和组织移植排斥。包括药物组成和使用方法。
• Double prodrugs of a fosmidomycin surrogate as antimalarial and antitubercular agents
  作者：Charlotte Courtens、Martijn Risseeuw、Guy Caljon、Louis Maes、Paul Cos、Anandi Martin、Serge Van Calenbergh

  DOI：10.1016/j.bmcl.2019.03.009

  日期：2019.5

  A series of eleven double prodrug derivatives of a fosmidomycin surrogate were synthesized and investigated for their ability to inhibit in vitro growth of P. falciparum and M. tuberculosis. A pivaloyloxymethyl (POM) phosphonate prodrug modification was combined with various prodrug derivatisations of the hydroxamate moiety. The majority of compounds showed activity comparable with or inferior to fosmidomycin

  合成了一系列11种磷霉素替代物的双前药衍生物，并研究了它们抑制恶性疟原虫和结核分枝杆菌的体外生长的能力。将新戊酰氧基甲基（POM）膦酸酯前药修饰物与异羟肟酸酯部分的各种前药衍生化反应相结合。大多数化合物对恶性疟原虫的活性与磷霉素相近或逊于磷霉素。N-苄基取代的氨基甲酸酯前药6f是最具活性的抗疟疾类似物，IC50值为0.64 µM。与磷霉素和母体POM前药5相反，2-硝基呋喃和2-硝基噻吩前药6i和6j显示出有希望的抗结核活性。

表征谱图