二乙基(苯基硫代甲基)磷酸酯 | 38066-16-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 二乙基(苯基硫代甲基)磷酸酯
• 中文别名: 苯硫甲基磷酸二乙酯；苯硫甲基膦酸二乙酯
• 英文名称: diethyl [(phenylthio)methyl]phosphonate
• 英文别名: diethyl [(phenylsulfanyl)methyl]phosphonate；Diethyl phenylthiomethylphosphonate；diethoxyphosphorylmethylsulfanylbenzene
• CAS: 38066-16-9
• 化学式: C₁₁H₁₇O₃PS
• mdl: MFCD00015130
• 分子量: 260.294
• InChiKey: FBUXEPJJFVDUFE-UHFFFAOYSA-N

物化性质

• 沸点：
  146-148 °C (0.5 mmHg)
• 密度：
  1.17
• 闪点：
  146-148°C/0.5mm
• 溶解度：
  难溶于水
• 稳定性/保质期：
  常规情况下不会分解，也没有任何危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2931900090
• 安全说明：
  S26,S37/39
• 储存条件：
  密封、阴凉、干燥保存。

SDS

Name:	Diethyl(Phenylthiomethyl)Phosphonate Material Safety Data Sheet
Synonym:	None Known
CAS:	38066-16-9

Section 1 - Chemical Product MSDS Name:Diethyl(Phenylthiomethyl)Phosphonate Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
38066-16-9	Diethyl(Phenylthiomethyl)Phosphonate	ca. 100	253-770-7

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 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. 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 tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 38066-16-9: 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: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 146 - 148 deg C @ .50mmHg
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: 1.1740g/cm3
Molecular Formula: C11H17O3PS
Molecular Weight: 260.151

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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, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 38066-16-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Diethyl(Phenylthiomethyl)Phosphonate - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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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# 38066-16-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 38066-16-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 38066-16-9 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

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	diethyl (chloro(phenylthio)methyl)phosphonate	59664-75-4	C11H16ClO3PS	294.739
  ——	Diethyl (phenylsulfinyl)methylphosphonate	50746-65-1	C11H17O4PS	276.293
  ——	bisphenylthiomethanephosphonate	73778-53-7	C17H21O3PS2	368.458
  ——	[Diethoxyphosphoryl(methylsulfanyl)methyl]sulfanylbenzene	73778-52-6	C12H19O3PS2	306.387
  对甲苯磺酰甲基磷酸二乙酯	diethyl p-toluenesulfonylmethylphosphonate	60682-95-3	C12H19O5PS	306.32

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	phenylsulfanylmethyl-phosphonic acid monoethyl ester	747407-63-2	C9H13O3PS	232.24
  ——	diethyl (1-(phenylthio)ethyl)phosphonate	55264-89-6	C12H19O3PS	274.321
  ——	diethyl (chloro(phenylthio)methyl)phosphonate	59664-75-4	C11H16ClO3PS	294.739
  ——	Diethyl (phenylsulfinyl)methylphosphonate	50746-65-1	C11H17O4PS	276.293
  ——	(S)-diethyl (phenylsulfinyl)methylphosphonate	227952-63-8	C11H17O4PS	276.293
  ——	bisphenylthiomethanephosphonate	73778-53-7	C17H21O3PS2	368.458
  苯砜基甲基膦酸二乙酯	diethyl phenylsulfonylmethylphosphonate	56069-39-7	C11H17O5PS	292.293
  ——	Phenylmercaptomethanphosphonsaeure	89854-56-8	C7H9O3PS	204.186
  ——	diethyl α,α-difluoro-α-(phenylthio)methylphosphonate	197356-91-5	C11H15F2O3PS	296.275
  ——	ethyl phenylsufenylmethanephosphonic chloridate	114077-36-0	C9H12ClO2PS	250.686

反应信息

• 作为反应物：
  描述：

  二乙基(苯基硫代甲基)磷酸酯 在 三氟化硼乙醚 、 1-(过氧化叔丁基)-1,2-苯碘酰-3(H)-酮 作用下， 以 水 、 乙腈 为溶剂， 反应 38.0h， 以82%的产率得到Diethyl (phenylsulfinyl)methylphosphonate
  参考文献：
  名称：

  用高价（叔丁基过氧）碘将硫化物氧化成亚砜。

  摘要：

  在乙腈-水中或二氯甲烷中，用结晶的（烷基过氧）碘化物，1-（叔丁基过氧）-1,2-苯并三恶唑-3（1H）-酮2a和2b氧化硫化物，可高产率提供亚砜。在乙腈水中测量一系列环取代的硫代苯甲醚3b（p-MeO），3c（p-Me）和3d（p-Cl）的相对氧化速率表明，电子释放基团（例如p- MeO和p-Me基团增加了氧化速率，相对速率因子与取代基常数的Hammett相关性提供了BF（3）的反应常数rho（+）= -2.23（sigma（+），r = 0.98）催化氧化，对于未催化氧化，rho = -3.32（sigma，r = 0.98）。检查了自由基清除剂加尔维诺尔的作用。对于存在和不存在BF（3）的乙腈水中的氧化，提出了一种机制，该机制涉及通过硫化物对2的碘（III）原子的亲核攻击而中间形成formation物种11。Et（2）O。另一方面，二氯甲烷中亚砜的氧化可能是通过自由基过程进行的，该过

  DOI：

  10.1021/jo970081q
• 作为产物：
  描述：

  氯甲基苯硫醚 在 亚磷酸三乙酯 作用下， 以61.1 grams (93.1%)的产率得到二乙基(苯基硫代甲基)磷酸酯
  参考文献：
  名称：

  Arylthiovinylcyclopropanecarboxylate insecticides

  摘要：

  揭示了具有一般公式##STR1##的芳基硫乙烯基环丙烷羧酸酯。还描述和举例了这些化合物及其新颖中间体的杀虫效果和制备方法。

  公开号：

  US04200644A1

文献信息

• Isomerisation of Vinyl Sulfones for the Stereoselective Synthesis of Vinyl Azides
  作者：Niall Collins、Robert Connon、Goar Sánchez‐Sanz、Paul Evans

  DOI：10.1002/ejoc.202001065

  日期：2020.10.22

  The efficient isomerisation of a range of γ‐azido substituted vinyl sulfones is reported. The corresponding vinyl azides are typically obtained with high levels of Z‐stereochemistry. An exception is when R is an α‐methyl substituent is present when the E‐vinyl azide was preferred.

  据报道，一系列γ-叠氮基取代的乙烯基砜得到了有效的异构化。相应的乙烯基叠氮化物通常以较高的Z立体化学含量获得。一个例外是，当优先使用E-乙烯基叠氮化物时，当R是一个α-甲基取代基时。
• Chemical introduction of the green fluorescence: imaging of cysteine cathepsins by an irreversibly locked GFP fluorophore
  作者：Maxim Frizler、Ilia V. Yampolsky、Mikhail S. Baranov、Marit Stirnberg、Michael Gütschow

  DOI：10.1039/c3ob41341a

  日期：——

  An activity-based probe, containing an irreversibly locked GFP-like fluorophore, was synthesized and evaluated as an inhibitor of human cathepsins and, as exemplified with cathepsin K, it proved to be suitable for ex vivo imaging and quantification of cysteine cathepsins by SDS-PAGE.

  合成了一种基于活性探针的不可逆锁定GFP样荧光团，并评估其作为人类半胱氨酸酶的抑制剂。以半胱氨酸酶K为例，该探针被证明适用于通过SDS-PAGE进行体外成像和定量分析半胱氨酸酶。
• Peptidyl allyl sulfones: a new class of inhibitors for clan CA cysteine proteases
  作者：Marion G. Götz、Conor R. Caffrey、Elizabeth Hansell、James H. McKerrow、James C. Powers

  DOI：10.1016/j.bmc.2004.07.016

  日期：2004.10

  series of peptidyl allyl sulfone inhibitors was discovered while trying to synthesize epoxy sulfone inhibitors from vinyl sulfones using basic oxidizing conditions. The various dipeptidyl allyl sulfones were evaluated with calpain I, papain, cathepsins B and L, cruzain and rhodesain and found to be potent inhibitors. In comparison to the previously developed class of vinyl sulfone inhibitors, the novel

  在尝试使用碱性氧化条件从乙烯基砜合成环氧砜抑制剂时，发现了一系列新的肽基烯丙基砜抑制剂。用钙蛋白酶I，木瓜蛋白酶，组织蛋白酶B和L，克鲁萨因和罗氏蛋白酶对各种二肽基烯丙基砜进行了评估，发现它们是有效的抑制剂。与先前开发的一类乙烯基砜抑制剂相比，新型二肽基烯丙基砜比相应的二肽基乙烯基砜更有效。观察到乙烯基砜前体的立体化学在二肽基烯丙基砜抑制剂的效力中起作用。
• Stereoselective Synthesis of 2-Deoxy-2-iodo-glycosides from Furanoses. A New Route to 2-Deoxy-glycosides and 2-Deoxy-oligosaccharides of <i>r</i><i>ibo </i>and <i>x</i><i>ylo</i> Configuration
  作者：Miguel Ángel Rodríguez、Omar Boutureira、Xavier Arnés、M. Isabel Matheu、Yolanda Díaz、Sergio Castillón

  DOI：10.1021/jo051461b

  日期：2005.12.1

  procedure involves three reactions: Wittig−Horner olefination to give alkenyl sulfanyl derivatives, electrophilic iodine-induced cyclization to give phenyl 2-deoxy-2-iodo-1-thio-hexo-glycosides, and glycosylation. Protected furanoses 1, 3, and 6−11, which include examples of the four possible isomeric configurations of furanoses, were reacted with diphenyl phenylsulfanylmethyl phosphine oxide to give the

  据报道从呋喃糖酶立体选择性合成2-脱氧-2-碘-己-和-庚-吡喃糖基糖苷的一般方法。拟议的方法提供了一种获取2-脱氧寡糖的新途径。该程序涉及三个反应：Wittig-Horner烯化生成链烯基硫烷基衍生物，亲电碘诱导的环化生成苯基2-脱氧-2-碘-1-硫代-己糖苷，以及糖基化。保护呋喃糖1，3，和6 - 11，其包括呋喃糖的四种可能的异构体构型的实施例中，与碳酸二苯苯基硫基甲基氧化膦，得到链烯基硫烷基衍生物进行反应2，4，和12− 16。这些化合物，得到苯基2-脱氧-2-碘-1-硫代糖苷的碘诱导的环化18，20，和22 - 27具有实际上完全区域选择性和立体选择性。6-产品内的环化，其中在C-2中的碘是一个顺式在C-3与烷氧基的关系，进行了几乎全部产生。具有核糖或木糖构型的化合物比具有其他构型的化合物获得更好的产率。化合物18，20，和22 - 27已发现在胆固醇和吡喃葡萄糖苷29a的糖基化
• Peptidyl allyl sulfones
  申请人：Powers C. James

  公开号：US20060241057A1

  公开（公告）日：2006-10-26

  The present disclosure provides compositions for inhibiting proteases, methods for synthesizing the compositions, and methods of using the disclosed protease inhibitors. Aspects of the disclosure include peptidyl allyl sulfone compositions that inhibit proteases, for example cysteine proteases, either in vivo or in vitro.

  本公开提供了用于抑制蛋白酶的组合物、合成这些组合物的方法，以及使用所披露的蛋白酶抑制剂的方法。公开内容的方面包括抑制蛋白酶的肽基烯丙基砜组合物，例如在体内或体外抑制半胱氨酸蛋白酶。

表征谱图