N-[(2-氰乙基)硫代]邻苯二甲酰亚胺 | 88683-57-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: N-[(2-氰乙基)硫代]邻苯二甲酰亚胺
• 中文别名: N-(2-氰基硫代)邻苯二甲酰胺
• 英文名称: N-[(2-cyanoethyl)sulfanyl]phthalimide
• 英文别名: N-[2-(cyanoethyl)thio]phthalimide；S-(2-cyanoethyl)phthalimide；N-(2-cyanoethylmercapto)phthalimide；N-[(2-Cyanoethyl)thio]phthalimide；3-(1,3-dioxoisoindol-2-yl)sulfanylpropanenitrile
• CAS: 88683-57-2
• 化学式: C₁₁H₈N₂O₂S
• mdl: MFCD01863529
• 分子量: 232.263
• InChiKey: MVZDBGUIRMGSOY-UHFFFAOYSA-N

物化性质

• 熔点：
  156-160 °C(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  86.5
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2930909090

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : N-[(2-Cyanoethyl)thio]phthalimide
CAS-No. : 88683-57-2

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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)
Causes skin irritation.
Causes serious eye irritation.
May cause respiratory irritation.
Precautionary statement(s)
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.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C11H8N2O2S
Molecular Weight : 232,26 g/mol
Component Concentration
N-[(2-Cyanoethyl)thio]phthalimide
CAS-No. 88683-57-2 -

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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
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, nitrogen oxides (NOx), Sulphur oxides, Hydrogen cyanide (hydrocyanic acid)
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. Evacuate personnel to safe areas. 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 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
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
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: Needles
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 156 - 160 °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- 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
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
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
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
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

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N-[(2-氰乙基)硫代]邻苯二甲酰亚胺 在 ammonium hypophosphite 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以81%的产率得到ammonium bis-S-(2-cyanoethyl) phosphorodithioate
  参考文献：
  名称：

  进一步的研究与腺苷5 ' -dithiophosphoromorpholidate。通过“三酯”方法方便地制备核苷二硫代磷酸酯

  摘要：

  腺苷5 ' -dithiophosphoromorpholidate 1c中发生反应以正磷酸盐，得到腺苷5 ' -（α，α-二硫代）二磷酸3c中但不转化为腺苷5 ' -phosphorodithioate 2c中通过酸性水解。描述了一种合成核苷二硫代磷酸酯的新方法。

  DOI：

  10.1016/j.tetlet.2004.01.135
• 作为产物：
  描述：

  邻苯二甲酸亚胺 、 2-氰基乙硫醇 在 溴 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 2.0h， 以90%的产率得到N-[(2-氰乙基)硫代]邻苯二甲酰亚胺
  参考文献：
  名称：

  2-（2-氰基乙基）硫烷基-1 H-异吲哚-1,3-（2 H）-二酮的制备及相关的硫转移剂

  摘要：

  标题化合物3和4-[（2-氰基乙基）硫烷基]吗啉-3,5-二酮12都可以方便地由2-氰基乙基二硫化物以高收率制备，其本身可以很容易地由S-（2-氰乙基）异硫脲氯化铵4。同样，二甲基和二苯基二硫化物也分别以良好的产率转化成2-甲基硫烷基-和2-苯基硫烷基-1 H-异吲哚-1,3-（2 H）-二酮8a和8b。

  DOI：

  10.1016/s0040-4020(97)00924-1

文献信息

• 2-5A ANALOGS AND THEIR METHODS OF USE
  申请人：Beigelman Leonid

  公开号：US20100331397A1

  公开（公告）日：2010-12-30

  Disclosed herein are compounds that activate RNaseL, methods of synthesizing compounds that activate RNaseL and the use of compounds that activate RNaseL for treating and/or ameliorating a disease or a condition, such as a viral infection, a bacterial infection, cancer and/or parasitic disease.

  本文披露了激活RNaseL的化合物，合成激活RNaseL的化合物的方法，以及利用激活RNaseL的化合物治疗和/或改善疾病或状况的用途，例如病毒感染、细菌感染、癌症和/或寄生虫病。
• Mechanochemical Synthesis of Short DNA Fragments
  作者：James D. Thorpe、Daniel O'Reilly、Tomislav Friščić、Masad J. Damha

  DOI：10.1002/chem.202001193

  日期：2020.7.22

  We demonstrate the first mechanochemical synthesis of DNA fragments by ball milling, enabling the synthesis of oligomers of controllable sequence and length using multi‐step, one‐pot reactions, without bulk solvent or the need to isolate intermediates. Mechanochemistry allowed for coupling of phosphoramidite monomers to the 5′‐hydroxyl group of nucleosides, iodine/water oxidation of the resulting phosphite

  我们展示了通过球磨进行的DNA片段的第一个机械化学合成，它可以使用多步单罐反应合成可控制序列和长度的寡聚体，而无需大量溶剂或无需分离中间体。机械化学作用使亚磷酰胺单体与核苷的5'-羟基偶联，碘/水氧化所得的亚磷酸三酯键，并就地去除了5'-二甲氧基三苯甲基（DMTr）保护基，收率高（可达60在三个步骤中的百分比）以单罐方式产生DNA二聚体。铣削条件下的H-膦酸酯化学成分可实现H的偶联和保护-膦酸酯键连接以及原位去除5'-DMTr保护基，可实现单锅法且收率高（三步产率高达65％，或每步约87％）。使用元素硫（S8）或硫转移试剂可以实现核苷酸间键的硫化，从而以良好的收率产生目标DNA硫代磷酸酯二聚体（分两步收率高达80％）。这项工作为创建用于DNA和RNA治疗剂的无溶剂合成方法打开了大门。
• Process for the preparation of phosphorothioate triesters
  申请人：——

  公开号：US20030099981A1

  公开（公告）日：2003-05-29

  A process for the synthesis of a phosphorothioate triester is provided. The process comprises the coupling of an H-phosphonate with an alcohol in the presence of a solution comprising both a coupling agent and a sulfur transfer agent. Preferably, the H-phosphorate and alcohol are protected nucleosides or oligonucleotides.

  提供一种合成磷酸硫酯三酯的过程。该过程包括在存在耦合剂和硫转移剂的溶液中，将H-膦酸酯与醇耦合。最好，H-膦酸酯和醇是受保护的核苷酸或寡核苷酸。
• Nucleoside phosphorothioate derivatives, synthesis and use thereof
  申请人：King's College London

  公开号：US05708161A1

  公开（公告）日：1998-01-13

  Inter alia, a process for the production of a nucleoside phosphorothioate derivative corresponding to the following general formula (I): ##STR1## characterized in that it comprises reacting a salt of a nucleoside H-phosphonate corresponding to the following general formula (II): ##STR2## with a thiol transfer agent corresponding to the following general formula (III): R.sup.2 --S--X (III) in the presence of a silylating agent and a base in a suitable solvent; and working-up the reaction mixture to isolate the desired product and change the counter-cation as desired; wherein M.sup.+ represents a suitable counter-cation; R.sup.1 represents an appropriate nucleoside or nucleoside analogue; R.sup.2 represents a desired protecting group, which may ultimately be removable by cleavage of its bond to the sulfur atom; and X represents a leaving group, is disclosed.

  其中，揭示了一种制备与下列通式（I）相对应的核苷酸磷酸硫酯衍生物的过程：##STR1## 其特征在于，在适当的溶剂中，在硅化试剂和碱的存在下，将下列通式（II）所对应的核苷酸H-膦酸盐与下列通式（III）所对应的硫醇转移试剂反应，并处理反应混合物以分离所需的产物并根据需要更改计数器阳离子；其中M.sup.+代表适当的计数器阳离子；R.sup.1代表适当的核苷酸或核苷酸类似物；R.sup.2代表所需的保护基，最终可以通过断裂与硫原子的键而去除；X代表离去基团。
• Synthesis of oligonucleotides
  申请人：Avecia Limited

  公开号：EP1325927A2

  公开（公告）日：2003-07-09

  A process for the synthesis in solution phase of a phosphorothioate triester is provided. The process comprises the solution phase coupling of an H-phosphonate with an alcohol in the presence of a coupling agent to form an H-phosphonate diester. The H-phosphonate diester is oxidised in situ with a sulfur transfer agent to produce the phosphorothioate triester. Preferably, the H-phosphonate and alcohol are protected nucleosides or oligonucleotides. Oligonucleotide H-phosphonates which can be used in the formation of phosphorothioate triesters are also provided.

  本发明提供了一种在溶液相中合成硫代磷酸酯三酯的工艺。该工艺包括在偶联剂存在下，将 H-膦酸盐与醇进行溶液相偶联，形成 H-膦酸盐二酯。H-phosphonate 二酯与硫转移剂原位氧化，生成硫代磷酸酯三酯。H-phosphonate 和醇最好是受保护的核苷或寡核苷酸。还提供了可用于形成硫代磷酸三酯的寡核苷酸 H-膦酸盐。