磷酰基乙酸 | 4408-78-0

• 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 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 中文名称: 磷酰基乙酸
• 中文别名: 膦酰基乙酸
• 英文名称: phosphonoacetic acid
• 英文别名: 2-phosphonoacetic acid
• CAS: 4408-78-0
• 化学式: C₂H₅O₅P
• mdl: MFCD00004311
• 分子量: 140.032
• InChiKey: XUYJLQHKOGNDPB-UHFFFAOYSA-N

物化性质

• 熔点：
  143-146 °C (lit.)
• 沸点：
  490.2±47.0 °C(Predicted)
• 密度：
  1.858±0.06 g/cm3(Predicted)
• 溶解度：
  水中的溶解度：100mg/mL，清澈至轻微的混浊，无色
• 物理描述：
  Solid
• 碰撞截面：
  134.5 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
• 稳定性/保质期：
  在常温常压下保持稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

ADMET

毒理性

• 副作用

Dermatotoxin - 皮肤烧伤。

Dermatotoxin - Skin burns.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

安全信息

• 危险等级：
  8
• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R22,R34
• WGK Germany：
  3
• 海关编码：
  2919900036
• RTECS号：
  AJ3278000
• 包装等级：
  III
• 危险类别：
  8
• 危险标志：
  GHS07
• 危险品运输编号：
  UN3261
• 危险性描述：
  H302
• 储存条件：
  请将药品存放在避光、通风干燥的地方，并密封保存。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Phosphonoacetic acid
CAS-No. : 4408-78-0
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Acute toxicity, Oral (Category 4)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
Precautionary statement(s) none
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R22 Harmful if swallowed.
S-phrase(s) none
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C2H5O5P
Molecular Weight : 140,03 g/mol
Component Concentration
Phosphonoacetic acid
CAS-No. 4408-78-0 -
EC-No. 224-558-1

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Oxides of phosphorus
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 143 - 146 °C - lit.
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- log Pow: -1,324
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin
May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: AJ3278000

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性

Phosphonoacetic acid (PAA) 是一种活性内源性代谢产物，具有限制 DNA biosynthesis 的潜力，并且具有抗病毒的活性。

靶点

Human Endogenous Metabolite

反应信息

• 作为反应物：
  描述：

  磷酰基乙酸 在 氯化亚砜 作用下， 生成 phosphonoacetylchloride
  参考文献：
  名称：

  Preparation of N-(phosphonoacetyl)-L-aspartic acid

  摘要：

  本文揭示了制备N-（磷酸乙酰）-L-天冬酰胺酸（PALA）的四钠盐和二钠盐的改进方法。目前的方法非常适合大量制备这些产品。这些方法的特定方面包括：（1）将PALA基团最初制备为二苯甲酯；（2）通过湍流沉淀完全去除乙酸和醋酸钠形式的杂质，从而制备出二钠PALA；以及（3）制备和纯化二苯甲酰PALA的环己胺盐，最终导致更纯净的最终产品。

  公开号：

  US04179464A1
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 在 盐酸 作用下， 以 水 为溶剂， 反应 9.0h， 以93%的产率得到磷酰基乙酸
  参考文献：
  名称：

  Applications of mesoporous titanium phosphonate functionalized with carboxylic groups

  摘要：

  通过简单的协同冷凝过程，使用磷酸乙酸和四氯化钛在酸性条件下合成了功能化的介孔钛磷酸酯，具有 –COOH 基团。所得到的介孔材料具有高比表面积和大孔体积，这些结果通过 XRD、TEM、SEM 和 N2 吸附分析得到了支持。磷酸酯基团的完整性进一步通过 FTIR 和 NMR 进行了表征。通过金属吸附-还原程序，成功地将钯纳米颗粒负载到材料上，显示出在铃木反应中具有高活性。此外，所获得的催化剂可以回收利用，且催化活性没有显著下降。

  DOI：

  10.1039/c4ra06952h
• 作为试剂：
  描述：

  N-cyclohexyl-N-ethylacrylamide 、 2,3-二氨基甲苯 在 磷酰基乙酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  发现强壁壁chochochoic acid早期抑制剂。

  摘要：

  耐甲氧西林的金黄色葡萄球菌（MRSA）的广泛出现极大地侵蚀了目前的β-内酰胺类抗生素的功效，并迫切需要新的治疗选择。使用金黄色葡萄球菌表型筛选策略，我们已经确定了预测与β-内酰胺在化学上协同作用的小分子早期壁壁胆酸（WTA）途径特异性抑制剂。这些先前公开的抑制剂，称为塔罗霉素，通过遗传和生化手段证明了抑制WTA生物合成第一步中的TarO。Tarocins在耐甲氧西林葡萄球菌的各种临床分离株中与广谱β-内酰胺类抗生素结合显示出强大的杀菌协同作用。将详细介绍他他霉素系列的合成和构效关系（SAR）。

  DOI：

  10.1016/j.bmcl.2016.06.090

文献信息

• Combining a Solution-Phase Derived Library with In-Situ Cellular Bioassay: Prompt Screening of Amide-Forming Minilibraries Using MTT Assay
  作者：Li-Wu Chiang、Kai Pei、Shao-Wei Chen、Ho-Lien Huang、Kun-Ju Lin、Tzu-Chen Yen、Chung-Shan Yu

  DOI：10.1248/cpb.57.714

  日期：——

  We constructed a minilibrary using a solution-phase synthesis through coupling of three core amino compounds (5′-amino-5′-deoxy uridine, 5′-amino-2′,5′-di-deoxy arabinosyl uridine, and butan-1-amine) with 30 carboxylic acids via amide bond formation. The simplified structural core compound butan-1-amine was selectively coupled with 9 carboxylic acids as control. 3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide assay of the crude mixtures showed that analogues derived from fenbufen, butylfenbufen C15; ethacrynic acid, butyl ethacrynic amide C18; and sphingosines, Sph-1, Sph-2 and U27 had an increased cytotoxicity against MCF-7 cells as well as A549 cells. Structural elucidation with molecular docking suggested that cytotoxicity of these compounds is mainly due to the inhibition of enzymes regulating cellular apoptosis.

  我们通过三种核心氨基酸化合物（5'-氨基-5'-脱氧尿苷、5'-氨基-2',5'-二脱氧阿糖尿苷和丁胺）与30种羧酸通过酰胺键形成，采用溶液相合成方法构建了一个微型库。简化的结构核心化合物丁胺选择性地与9种羧酸进行了耦合作为对照。对粗混合物的3-(4,5-二甲基-2-噻唑基)-2,5-二苯基-2H-四唑溴盐检测显示，来自非诺洛芬、丁基非诺洛芬C15；依他尼酸、丁基依他尼酸酰胺C18；以及鞘氨醇、Sph-1、Sph-2和U27的类似物对MCF-7细胞以及A549细胞表现出增强的细胞毒性。通过分子对接进行结构阐明表明，这些化合物的细胞毒性主要由于抑制调控细胞凋亡的酶。
• NGCYCLOARTANONE DERIVATIVES WITH ANTICANCER ACTIVITY
  申请人：Long Christophe

  公开号：US20120077777A1

  公开（公告）日：2012-03-29

  The present invention relates to a compound of following formula (I): or to a pharmaceutically acceptable salt thereof, as well as to pharmaceutical compositions including same and to the use thereof as a drug, in particular for treating a proliferative disease such as cancer.

  本发明涉及以下式（I）的化合物： 或其药学上可接受的盐，以及包括相同的药物组合物和将其用作药物的用途，特别是用于治疗增殖性疾病如癌症。
• 31P NMR—structure correlations for phosphonocarboxylic acids and esters
  作者：Sabine Olagnon-Bourgeot、Francine Chastrette、Didier Wilhelm

  DOI：10.1002/mrc.1260331205

  日期：1995.12

  31P chemical shift‐structure correlations were established from methyl and ethyl esters of simple phosphonocarboxylic acids. The influence of solvent, acidity, function and neighbourhood of phosphorus was studied. The correlations could be extended and led to the identification of esters obtained when a series of phosphonocarboxylic acids were reacted with alcohols—reactions which were designed as

  31P 化学位移-结构关联是从简单膦酰基羧酸的甲酯和乙酯中建立的。研究了溶剂、酸度、磷的作用和邻域对磷的影响。当一系列膦酰基羧酸与醇反应时，可以扩展相关性并导致对酯的鉴定 - 这些反应被设计为这些酸的纤维素交联模型。
• A supramolecular approach towards the construction of molecular salts using phosphonic acid and pyrazole
  作者：Udai P. Singh、Shikha Narang

  DOI：10.1039/c4ce00484a

  日期：——

  formation of distinct supramolecular organic frameworks (SOFs) with an array of reliable synthons. Structural analyses revealed that both compounds 1 and 2 exhibited a layered structure but the parallel stacked sheets are displaced in the former salt as compared to the latter. Salts 4 and 5 exhibited a three-dimensional (3D) hydrogen bonded supramolecular network and 2D porous supramolecular network, respectively

  吡唑类似物与各种膦酸的系统共结晶导致膦酸和吡唑之间稳固的超分子合成子，负责固态设计。一系列膦酸和亚甲基双（3,5-二甲基吡唑）（MBPz）产生了六种分子盐，即。[HPPA - ·H 2 PPA·HMBPz + ·MBPz]（1），[（H吨BPA -）2 ·H 2 MBPz 2+ ·乙醇]（2），[HPAA - ·HMBPz + ·MBPz·MeOH中] （3），[HPPRA - ·HMBPz + ]（4），[H 2 EA 2- ·H 2 MBPz 2+ ·S]（5）和[H 3 DPA - ·（H 2 DPA 2-）0.5 ·H 2 MBPz 2+ ·（H 2 O）0.4 ] （6）其中H 2 PPA =苯基膦酸，H 2 PAA =膦酰基乙酸，H 2 PPRA = 3-膦酰基丙酸，H 2 t BPA =叔丁基膦酸，H 4 EA =乙二膦酸，H 4DPA ＝ [1，4-亚苯基双（亚甲基）]二膦酸，S
• Synthesis and anti-herpes simplex activity of analogs of phosphonoacetic acid
  作者：Thomas R. Herrin、John S. Fairgrieve、Robert R. Bower、Nathan L. Shipkowitz、James C. H. Mao

  DOI：10.1021/jm00215a008

  日期：1977.5

  The synthesis of monoesters (P and C) of phosphonoacetic acid (PA) is given. The carboxyl esters were prepared by two methods: the reaction of chloroacetates with tris(trimethylsilyl) phosphite, followed by hydrolysis; and by the acid-catalyzed esterification of PA with the appropriate alcohol. P-Monoesters of PA were prepared either by the reaction of alkyl[bis(trimethylsilyl)] phosphite with benzyl

  给出了膦酰乙酸（PA）的单酯（P和C）的合成。羧基酯是通过两种方法制备的：氯乙酸酯与亚磷酸三（三甲基甲硅烷基）酯的反应，然后水解。以及通过PA与适当的醇进行酸催化的酯化反应。通过烷基[双（三甲基甲硅烷基）]亚磷酸酯与氯乙酸苄酯的反应，然后脱保护，或使亚磷酸二甲基苯基酯与溴乙酸苄酯的反应，然后进行氢解，可以制备PA的P-单酯。报道了三种芳基-（烷基-）次膦酸衍生物。评价上述化合物对HSV诱导的DNA聚合酶和感染疱疹性皮炎的动物的抗疱疹活性。

表征谱图