三甲硅基甲基膦酸二甲酯 | 13433-42-6

• 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: 三甲硅基甲基膦酸二甲酯
• 中文别名: 三甲基硅烷甲基膦酸二甲酯
• 英文名称: dimethyl (trimethylsilyl)methylphosphonate
• 英文别名: Trimethylsilylmethyl-phosphonsaeure-dimethylester；Dimethyl trimethylsilylmethylphosphonate；dimethoxyphosphorylmethyl(trimethyl)silane
• CAS: 13433-42-6
• 化学式: C₆H₁₇O₃PSi
• mdl: MFCD00042921
• 分子量: 196.258
• InChiKey: QBHFBIHXALNDCB-UHFFFAOYSA-N

物化性质

• 沸点：
  111-114 °C21.5 mm Hg(lit.)
• 密度：
  1.024 g/mL at 25 °C(lit.)
• 闪点：
  160 °F
• 稳定性/保质期：
  常温常压下稳定，避免与水分、潮湿和氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2931900090
• 安全说明：
  S26
• 储存条件：
  常温密闭保存，需置于阴凉、通风、干燥的惰性气体环境中。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Dimethyl trimethylsilylmethylphosphonate
CAS-No. : 13433-42-6
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]
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36 Wear suitable protective clothing.
Caution - substance not yet tested completely.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C6H17O3PSi
Molecular Weight : 196,26 g/mol
Component Concentration
Dimethyl trimethylsilylmethylphosphonate
CAS-No. 13433-42-6 -

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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
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
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.
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
For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large
fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or
spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of
water.
Special hazards arising from the substance or mixture
Carbon oxides, Oxides of phosphorus, silicon oxides
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
Use personal protective equipment. 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). 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 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.
Exposure to moisture.
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
impervious 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: clear, liquid
Colour: colourless
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 111 - 114 °C at 28,7 hPa
boiling range
g) Flash point 71 °C - closed cup
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 1,024 g/mL at 25 °C
n) Water solubility no data available
o) Partition coefficient: n- no data available
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
Heat, flames and sparks.
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
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious 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: 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
This combustible material may be burned in a chemical incinerator equipped with an afterburner and
scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material.
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

反应信息

• 作为反应物：
  描述：

  三甲硅基甲基膦酸二甲酯 在 二苯甲酮 作用下， 生成 Dimethyl trimethylsilyl phosphite
  参考文献：
  名称：

  通过二甲基三甲基甲硅烷基甲基膦酸酯的 1,3-甲硅烷基迁移形成磷叶立德。磷酸盐在 WITTIG 反应中的应用

  摘要：

  羰基化合物与三甲基甲硅烷基甲基膦酸二甲酯的反应得到末端烯烃、甲基膦酸二甲酯、甲基三甲基甲硅烷基甲基膦酸酯和磷酸三甲基甲硅烷基二甲酯。末端烯烃可以通过羰基化合物与通过三甲基甲硅烷基甲基膦酸二甲酯的 1,3-甲硅烷基迁移产生的磷叶立德的 Wittig 型反应形成。

  DOI：

  10.1246/cl.1978.1385
• 作为产物：
  描述：

  dimethyl lithium(trimethylsilyl)methylphosphonate 在 盐酸 作用下， 生成 三甲硅基甲基膦酸二甲酯
  参考文献：
  名称：

  A One Step Generation of α-Lithiotrimethylsilylalkanephosphonates. A New Preparative Route to Dialkyl 1-(Trimethylsilyl)alkanephosphonates and Vinylphosphonates

  摘要：

  DOI：

  10.1055/s-1986-31828

文献信息

• Total Synthesis and Structural Revision of Chaetoviridins A
  作者：Mehdi Makrerougras、Romain Coffinier、Samuel Oger、Arnaud Chevalier、Cyrille Sabot、Xavier Franck

  DOI：10.1021/acs.orglett.7b02053

  日期：2017.8.4

  The first synthesis of the proposed structures of chaetoviridins A 1–4 has been achieved in 10 steps by controlling the syn- or anti-aldol side chain. The angular lactone has been regioselectively introduced by condensation of a chiral dioxin-4-one to cazisochromene. Comparison of the NMR and circular dichroism data of the synthesized and reported natural products led to the complete reassignment and

  chaetoviridins A的提出的结构的第一合成1 - 4已经通过控制在10个步骤实现顺式或-抗-aldol侧链。角内酯是通过手性二恶英-4-酮缩合至卡异异戊烯而选择性地引入的。合成和报告的天然产物的NMR和圆二色性数据的比较导致chaetoviridins的完全重新分配和重命名。
• Convenient Synthesis of 1-(Trimethylsilyl)- and 1-(Trimethylstannyl)vinylphosphonates
  作者：Yoshiharu Okada、Tomohiro Maruyama、Shin-ichi Tamura、Hirohito Kameoka、Satoshi Masuda、Yuichiro Tokuda、Junya Sakai、Masato Nomura

  DOI：10.1080/10426507.2013.855765

  日期：2014.6.3

  Abstract Dimethyl 1,1-bis(trimethylsilyl)methylphosphonate and dimethyl 1-(trimethylsilyl)-1-(trimethylstannyl)methylphosphonate were succeeded to react with aromatic aldehydes in the presence of methyl benzoate as additive to give the corresponding vinylphosphonates in moderate yields. GRAPHICAL ABSTRACT

  摘要 在苯甲酸甲酯作为添加剂存在下，1,1-双（三甲基甲硅烷基）甲基膦酸二甲酯和1-（三甲基甲硅烷基）-1-（三甲基甲锡基）甲基膦酸二甲酯与芳香醛反应，得到相应的乙烯基膦酸酯，收率适中。图形概要
• Novel One-pot Three-component Coupling Reaction with Trimethylsilylmethyl-phosphonate, Acyl Fluoride, and Aldehyde through the Horner–Wadsworth–Emmons Reaction
  作者：Taiki Umezawa、Tomoya Seino、Fuyuhiko Matsuda

  DOI：10.1021/ol301879a

  日期：2012.8.17

  A novel three-component coupling between trimethylsilylmethylphosphonate, acyl fluoride, and aldehyde has been developed. A sequential nucleophilic addition of lithio-trimethylsilylmethylphosphonate to the acyl fluoride and Horner–Wadsworth–Emmons reaction of an aldehyde with the lithio-β-ketophosphonate generated in situ by desilylation at the α-position of the α-silyl-β-ketophosphonate by fluoride

  已经开发了三甲基甲硅烷基甲基膦酸酯，酰基氟和醛之间的新型三组分偶联。硫代三甲基甲硅烷基甲基膦酸酯的顺序亲核加成反应，以及醛与氟在α-甲硅烷基-β-酮膦酸酯的α-位上被甲硅烷基化而就地产生的硫代-β-酮膦酸酯与醛的霍纳-沃兹沃思-埃蒙斯反应一锅操作干净利落地进行了。通过这种一锅法，以高收率和高立体选择性获得了各种E-和Z-烯酮。
• Fluoride Ion-Induced Horner–Emmons Reaction of α-Silylalkylphosphonic Derivatives with Carbonyl Compounds
  作者：Takayuki Kawashima、Takafumi Ishii、Naoki Inamoto

  DOI：10.1246/bcsj.60.1831

  日期：1987.5

  Dimethyl α-trimethylsilylbenzylphosphonate was allowed to react with carbonyl compounds in the presence of fluoride ion to give the corresponding olefins in fairly good yields. Use of CsF in tetrahydrofuran gave the best result. On the other hand, dimethyl trimethylsilylmethylphosphonate was allowed to react similarly with benzophenone to afford 1,1-diphenylethylene, dimethyl methylphosphonate, and

  在氟离子存在下，使α-三甲基甲硅烷基苄基膦酸二甲酯与羰基化合物反应，以相当好的收率得到相应的烯烃。在四氢呋喃中使用 CsF 给出了最好的结果。另一方面，使三甲基甲硅烷基甲基膦酸二甲酯与二苯甲酮类似地反应，得到1,1-二苯基乙烯、甲基膦酸二甲酯和2,2-二苯基乙烯基膦酸二甲酯。通过使用 O,O-二乙基三甲基甲硅烷基甲基硫代膦酸酯获得了类似的结果。但是，三甲基甲硅烷基甲基膦酸双（二乙酰胺）的反应仅提供原脱甲硅烷化产物。
• Chemoselective Synthesis of β-Ketophosphonates Using Lithiated α-(Trimethylsilyl)methylphosphonate
  作者：Simon Specklin、Janine Cossy

  DOI：10.1021/acs.joc.5b00039

  日期：2015.3.20

  A highly chemoselective synthesis of beta-ketophosphonates from pentafluorophenyl esters and lithiated methyl alpha-(trimethylsilyl)methylphosphonate has been developed. This mild lithiated phosphonate reagent allows the synthesis of functionalized beta-ketophosphonates in the presence of unactivated esters with high yields. This method has been compared with the standard lithiated methylphosphonate reagent.