P-甲基-膦酸单(2-甲基丙基)酯 | 1604-38-2

• 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: P-甲基-膦酸单(2-甲基丙基)酯
• 中文别名: 甲基磷羧酸氢异丁酯
• 英文名称: isobutyl methylphosphonic acid
• 英文别名: iBMPA；2-Methylpropyl Hydrogen (R)-Methylphosphonate；methyl(2-methylpropoxy)phosphinic acid
• CAS: 1604-38-2
• 化学式: C₅H₁₃O₃P
• mdl: MFCD00603003
• 分子量: 152.13
• InChiKey: ZNGLGLXWTVMUCL-UHFFFAOYSA-N

物化性质

• 沸点：
  142-144 °C(Press: 1.5 Torr)
• 密度：
  1.0657 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2931900090

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Isobutyl hydrogen methylphosphonate
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]
Flammable liquids (Category 2)
Acute toxicity, Oral (Category 3)
Acute toxicity, Inhalation (Category 3)
Acute toxicity, Dermal (Category 3)
Specific target organ toxicity - single exposure (Category 1)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Highly flammable. Toxic by inhalation, in contact with skin and if swallowed. Toxic: danger of very serious
irreversible effects through inhalation, in contact with skin and if swallowed.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Danger
Hazard statement(s)
H225 Highly flammable liquid and vapour.
H301 + H311 + H331 Toxic if swallowed, in contact with skin or if inhaled
H370 Causes damage to organs.
Precautionary statement(s)
P210 Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P260 Do not breathe dust/ fume/ gas/ mist/ vapours/ spray.
P280 Wear protective gloves/ protective clothing.
P301 + P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/
physician.
P311 Call a POISON CENTER or doctor/ physician.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R11 Highly flammable.
R23/24/25 Toxic by inhalation, in contact with skin and if swallowed.
R39/23/24/25 Toxic: danger of very serious irreversible effects through inhalation, in
contact with skin and if swallowed.
S-phrase(s)
S7 Keep container tightly closed.
S16 Keep away from sources of ignition - No smoking.
S36/37 Wear suitable protective clothing and gloves.
S45 In case of accident or if you feel unwell, seek medical advice immediately
(show the label where possible).
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Mixtures
Component Classification Concentration
Methanol
CAS-No. 67-56-1 Flam. Liq. 2; Acute Tox. 3; 50 - 100 %
EC-No. 200-659-6 STOT SE 1; H225, H301 +
Index-No. 603-001-00-X H311 + H331, H370
Registration number 01-2119433307-44-XXXX F, T, R11 - R23/24/25 -
R39/23/24/25
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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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. Take victim immediately to hospital. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Do NOT induce vomiting. 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.
Methyl alcohol may be fatal or cause blindness if swallowed., Cannot be made non-poisonous., Effects due
to ingestion may include:, Nausea, Headache, Vomiting, Gastrointestinal disturbance, Dizziness,
Weakness, Confusion.
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
no data available
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
Use water spray to cool unopened containers.

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove
all sources of ignition. Evacuate personnel to safe areas. Beware of vapours accumulating to form
explosive concentrations. Vapours can accumulate in low areas.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Methods and materials for containment and cleaning up
Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and
place in container for disposal according to local regulations (see section 13).
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 inhalation of vapour or mist.
Keep away from sources of ignition - No smoking.Take measures to prevent the build up of electrostatic
charge.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Recommended storage temperature: -20 °C
Specific end use(s)
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
Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling
the product.
Personal protective equipment
Eye/face protection
Face shield and safety glasses 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, Flame retardant antistatic protective clothing, The type
of protective equipment must be selected according to the concentration and amount of the
dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator
with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup
to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air
respirator. 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: liquid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and 64 - 65 °C at 1,013 hPa
boiling range
g) Flash point 9,7 °C - closed cup
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower Upper explosion limit: 36 %(V)
flammability or Lower explosion limit: 6 %(V)
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density 0,791 g/cm3 at 20 °C
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition 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
Heat, flames and sparks. Extremes of temperature and direct sunlight.
Incompatible materials
Acids, Oxidizing agents, Alkali metals, Strong oxidizing agents, Strong acids, Acid chlorides, Acid
anhydrides, Reducing agents, Strong reducing agents, Phosphorus halides
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 Toxic if inhaled. May cause respiratory tract irritation.
Ingestion Toxic if swallowed.
Skin Toxic 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.
Methyl alcohol may be fatal or cause blindness if swallowed., Cannot be made non-poisonous., Effects due
to ingestion may include:, Nausea, Headache, Vomiting, Gastrointestinal disturbance, Dizziness,
Weakness, Confusion.
Additional Information
RTECS: Not available

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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
Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting
as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal
company.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: 1230 IMDG: 1230 IATA: 1230
UN proper shipping name
ADR/RID: METHANOL, SOLUTION
IMDG: METHANOL, SOLUTION
IATA: Methanol, SOLUTION
Transport hazard class(es)
ADR/RID: 3 (6.1) IMDG: 3 (6.1) IATA: 3 (6.1)
Packaging group
ADR/RID: II IMDG: II IATA: II
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
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

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Section 16. OTHER INFORMATION
Text of H-code(s) and R-phrase(s) mentioned in Section 3
Acute Tox. Acute toxicity
Flam. Liq. Flammable liquids
H225 Highly flammable liquid and vapour.
H301 + H311 + Toxic if swallowed, in contact with skin or if inhaled
H331
H370 Causes damage to organs.
STOT SE Specific target organ toxicity - single exposure
F Highly flammable
T Toxic
R11 Highly flammable.
R23/24/25 Toxic by inhalation, in contact with skin and if swallowed.
R39/23/24/25 Toxic: danger of very serious irreversible effects through inhalation, in contact with
skin and if swallowed.
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  P-甲基-膦酸单(2-甲基丙基)酯 、 o-Butyl isopropylphosphonochloridate 在 aluminum oxide 作用下， 反应 0.08h， 以91.5%的产率得到O-butyl-O'-isobutyl-P-isopropyl-P'-methyl pyrophosphonate
  参考文献：
  名称：

  Surface Mediated Synthesis of Unsymmetrical O,O-dialkyl Alkyl Pyrophosphonates using Neutral Alumina: Potential Chemical Weapons Convention Related Compounds

  摘要：

  介绍了以 O-烷基烷基膦酸为原料，通过表面介导合成非对称 O,O'-二烷基烷基焦磷酸盐的方法。这些焦磷酸盐被列入《化学武器公约》（CWC）附表 2B4。此外，还研究了色谱级 Al2O3 的存在对一系列烷基膦酸磷化的影响。对于具有不同烷基的膦酸，观察到在 Al2O3 的存在下形成的受阻程度较高的焦磷酸盐的产率较高。与传统方法相比，该方法具有操作简便、反应时间短和产率高等优点。

  DOI：

  10.3184/030823408x318316
• 作为产物：
  描述：

  isobutyl methyl methylphosphonate 在 甲醇 作用下， 以 氯仿 为溶剂， 反应 12.0h， 生成 P-甲基-膦酸单(2-甲基丙基)酯
  参考文献：
  名称：

  有机磷化学。第1部分。烷基甲基膦酸的合成

  摘要：

  通过三步路线合成了结构RO（HO）P（O）Me的几种烷基氢甲基膦酸酯[R =  i -Pr，n -Bu，我-Bu，s -Bu，pinacolyl Me 3 C-CH（Me）-，环戊基 和 环己基]。 亚磷酸三甲酯 被酯交换 酒类 在钠存在下 催化剂得到6–64％的混合亚磷酸酯（MeO）2 POR。用这些治疗甲基碘以66–95％的收率得到烷基甲基甲基膦酸酯RO（MeO）P​​（O）Me。可选择的脱甲基 这些化合物的 溴三甲基硅烷， 其次是 甲醇分解甲硅烷基磷酯RO（Me 3 SiO）P（O）Me生成氢膦酸酯 收率为60–97％。

  DOI：

  10.1039/b007077g

文献信息

• Molecular Engineering of Organophosphate Hydrolysis Activity from a Weak Promiscuous Lactonase Template
  作者：Monika M. Meier、Chitra Rajendran、Christoph Malisi、Nicholas G. Fox、Chengfu Xu、Sandra Schlee、David P. Barondeau、Birte Höcker、Reinhard Sterner、Frank M. Raushel

  DOI：10.1021/ja405911h

  日期：2013.8.7

  lactonase (PLL) family that show promiscuous organophosphate-degrading activity. Starting from a weakly promiscuous PLL scaffold (Dr0930 from Deinococcus radiodurans ), we designed an extremely efficient organophosphate hydrolase (OPH) with broad substrate specificity using rational and random mutagenesis in combination with in vitro activity screening. The OPH activity for seven organophosphate substrates

  酶的快速进化为蛋白质非凡的适应性提供了独特的分子见解，并有助于阐明氨基酸序列、结构和功能之间的关系。我们研究了来自 Pseudomonas diminuta (PdPTE) 的磷酸三酯酶的进化，该酶以显着的催化效率水解合成有机磷酸酯。PTE 被认为是一种进化上“年轻”的酶，据推测它是从磷酸三酯酶样内酯酶 (PLL) 家族的成员进化而来的，这些成员表现出混杂的有机磷降解活性。从弱混杂的 PLL 支架（来自耐辐射奇异球菌的 Dr0930）开始，我们使用合理和随机诱变结合体外活性筛选设计了一种具有广泛底物特异性的极其有效的有机磷酸酯水解酶 (OPH)。七个有机磷底物的 OPH 活性同时增强了多达 5 个数量级，实现了高达 10(6) M(-1) s(-1) 的催化效率的绝对值。结构和计算分析确定了工程化 PLL 变体增强 OPH 活性的分子基础，并证明 PdPTE 和工程化 PLL 中的 OPH
• [EN] VARIANTS OF PHOSPHOTRIESTERASE FOR THE HYDROLYSIS AND DETOXIFICATION OF NERVE AGENTS<br/>[FR] VARIANTS DE PHOSPHOTRIESTERASE POUR L'HYDROLYSE ET LE DETOXIFICATION D'AGENTS NEUROTOXIQUES
  申请人：RAUSHEL FRANK M

  公开号：WO2015196106A1

  公开（公告）日：2015-12-23

  Variants of phosphotriesterase have been created that exhibit enhanced hydrolysis of V-type and G-type nerve agents over wild-type phosphotriesterase. V- and G-type nerve agents have an SP and RP enantiomer. The SP enantiomers are more toxic. V-type nerve agents are among the most toxic substances known. Variants of phosphotriesterase can prefer to hydrolyze one enantiomer of VX over the other enantiomer.

  已经创造出的磷酸三酯酶变体表现出对野生型磷酸三酯酶更强的水解作用，可以加速对V型和G型神经毒剂的水解。V型和G型神经毒剂有SP和RP对映体。SP对映体更具毒性。V型神经毒剂是已知最具毒性的物质之一。磷酸三酯酶的变体可以更倾向于水解VX的一个对映体而不是另一个对映体。
• Dimethoxytriadinylation LC–MS/MS of Novichok A-Series Degradation Products in Human Urine
  作者：Akinori Yamaguchi、Hajime Miyaguchi、Manabu Tokeshi

  DOI：10.1021/acs.analchem.1c04634

  日期：2022.3.22

  Novichok A-series compounds, novel nerve agents, pose an increasing threat to citizens worldwide; however, no analytical methods have been reported for detecting their hydrolysis products. Herein, a screening method was developed to detect and identify Novichok A-series degradation products (hydrolysates of A230, A232, A234, A262, and one related compound) and alkyl methylphosphonic acids (RMPAs, conventional nerve agent hydrolysates) using liquid chromatography–tandem mass spectrometry (LC–MS/MS). We identified a suitable derivatization reagent, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM), and optimized the reaction conditions. The derivatized esters of Novichok A-series degradation products were stable and easily detected. We used this derivatization to achieve the first analytical method for Novichok hydrolysis products in urine (0.40–4.0 ng/mL). The detection limits of the RMPAs (0.1–0.4 ng/mL) were comparable to those presented in previous reports involving pentafluorobenzylation or direct LC–MS/MS. The applicability of the newly developed method was evaluated by analyzing urine samples from the OPCW Fifth Biomedical Proficiency Test.

  Novichok A系列化合物，这些新型神经毒剂，对全球公民构成日益严重的威胁；然而，目前尚未报告检测其水解产物的分析方法。在此，我们开发了一种筛选方法，通过液相色谱–串联质谱（LC–MS/MS）检测和鉴定Novichok A系列降解产物（A230、A232、A234、A262及一种相关化合物的水解产物）和烷基甲基膦酸（RMPAs，即传统神经毒剂的水解产物）。我们确定了一种合适的衍生化试剂，4-(4,6-二甲氧基-1,3,5-三嗪-2-基)-4-甲基吗啉氯化物（DMTMM），并优化了反应条件。Novichok A系列降解产物的衍生化酯稳定且易于检测。我们利用这一衍生化方法首次实现了对尿液中Novichok水解产物的分析（0.40–4.0 ng/mL）。RMPAs的检测限（0.1–0.4 ng/mL）可与之前报告的五氟苯基化或直接LC–MS/MS的结果媲美。通过分析来自OPCW第五届生物医学能力测试的尿液样本，评估了新开发方法的适用性。
• Structural determination of nerve agent markers using gas chromatography mass spectrometry after derivatization with 3-pyridyldiazomethane
  作者：Jenny Rattfelt Nyholm、Tomas Gustafsson、Anders Östin

  DOI：10.1002/jms.3225

  日期：2013.7

  very similar spectra for many alkyl phosphonic acid isomers, which complicates the identification process. We present a new reagent, 3‐pyridyldiazomethane, for preparing picolinyl ester derivatives of alkyl methylphosphonic acids facilitating the determination of their structure by enhancing predictable fragmentation of the O‐alkyl chain. This fragmentation is directed by the nitrogen nucleus of the pyridyl

  神经制剂是《化学武器公约》所禁止的一类有机磷化学品。他们的降解产物膦酸被分析为神经毒剂污染和使用的标志。由于膦酸是非挥发性的且极性很大，因此在分析之前，通过GC-MS对其进行鉴定需要进行衍生化步骤。气相色谱电子碰撞质谱分析的标准衍生化方法可提供许多烷基膦酸异构体非常相似的光谱，这使鉴定过程复杂化。我们提出了一种新的试剂3-吡啶基重氮甲烷，用于制备烷基甲基膦酸的吡啶甲酸酯衍生物，通过增强O的可预测片段化来促进其结构的确定烷基链。这种断裂是由吡啶基部分的氮核控制的，吡啶基部分的氮核从O烷基链中提取氢，诱导碳-碳键的自由基断裂，从而引起大量断裂，可用于详细阐明O的结构。烷基部分。通过比较由十二种己基甲基膦酸异构体形成的吡啶甲基酯的光谱，测试了相关异构体的可分离性。光谱库匹配和主成分分析表明，与标准操作程序中使用的相应三甲基甲硅烷基衍生物相比，吡啶甲酸酯的分离效果更高。建议的方法将改善膦酸的明确结构测定过程。版权所有©2013
• Alkyl methylphosphonic acids, the degradation products of organophosphorous CWA — preparation and direct quantitative GC-FID analysis
  作者：Iwona Połeć、Anna Kiełczewska、Leszek Konopski、Grażyna Oleksa、Hanna Krukowska、Jan Legocki

  DOI：10.2478/s11532-010-0102-3

  日期：2010.12.1

  Seven alkyl methylphosphonic acids, products of hydrolytic degradation of organophosphorus chemical warfare agents, were obtained with a high purity (mostly above 98%), with the aim of being applyed as future certified reference materials. Ethyl (EMPA), isopropyl (IMPA), pinacolyl (PMPA), butyl (BUMPA), isobutyl (IBUMPA), cyclohexyl (CHMPA) and 2-ethylhexyl (EHMPA) monoesters of MPA were synthesized

  获得了七种烷基甲基膦酸，它们是有机磷化学战剂的水解降解产物，具有很高的纯度（大多高于98％），目的是用作将来认证的参考材料。合成了MPA的乙基（EMPA），异丙基（IMPA），频哪醇（PMPA），丁基（BUMPA），异丁基（IBUMPA），环己基（CHMPA）和2-乙基己基（EHMPA）单酯，并通过MS EI，FTIR和NMR进行了表征（1 H，13 C，31P），TLC以及衍生化后的GC和GC-MS。建立了在非衍生化烷基甲基膦酸的CP-FFAP CB柱上直接定量GC FID分析的条件。这是对游离烷基膦酸进行定向GC分析的首次成功尝试。确定了它们的化学纯度，并用GC-FID方法评估了其中一些的定量极限（LOQ）值。