(3,5,5-三甲基环己-2-烯亚基)丙二腈 | 23051-44-7

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 芳香烃
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (3,5,5-三甲基环己-2-烯亚基)丙二腈
• 英文名称: 3-dicyanomethylidene-1,5,5-trimethylcyclohexene
• 英文别名: 2-(3,5,5-trimethylcyclohex-2-enylidene)malononitrile；(3,5,5-trimethylcyclohex-2-enylidene)malononitrile；2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile；dicyanoisophorone；2-(3,5,5-trimethyl-2-cyclohexen-1-ylidene)-propanedinitrile；2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)propanedinitrile；2-(3,5,5-trimethyl-2-cyclohexenylidene)malononitrile；2-(3,5,5-trimethylcyclohex-2-en-1-yl)malononitrile；3-dicyanomethylene-1,5,5-trimethylcyclohexene；Propanedinitrile, (3,5,5-trimethyl-2-cyclohexen-1-ylidene)-
• CAS: 23051-44-7
• 化学式: C₁₂H₁₄N₂
• mdl: MFCD00228058
• 分子量: 186.257
• InChiKey: QTUUBOZSGQFLRZ-UHFFFAOYSA-N

物化性质

• 熔点：
  73-77 °C (lit.)
• 沸点：
  175-176 °C(Press: 19 Torr)
• 密度：
  1.007±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  如果按照规定使用和储存，则不会分解，且未有已知危险发生。 应避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S36/37
• 危险类别码：
  R22,R43
• WGK Germany：
  3
• 危险品运输编号：
  NONH for all modes of transport
• 海关编码：
  2926909090
• 危险标志：
  GHS07
• 危险性描述：
  H317
• 危险性防范说明：
  P280
• 储存条件：
  请将药品存放在密闭、阴凉干燥的地方，并保持良好通风。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : (3,5,5-Trimethylcyclohex-2-enylidene)malononitrile
CAS-No. : 23051-44-7
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 sensitization (Category 1)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed. May cause sensitization by skin contact.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H317 May cause an allergic skin reaction.
Precautionary statement(s)
P280 Wear protective gloves.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R22 Harmful if swallowed.
R43 May cause sensitization by skin contact.
S-phrase(s)
S36/37 Wear suitable protective clothing and gloves.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C12H14N2
Molecular Weight : 186,25 g/mol
Component Concentration
(3,5,5-Trimethylcyclohex-2-enylidene)malononitrile
CAS-No. 23051-44-7 -

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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, nitrogen oxides (NOx)
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
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, 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: 73 - 77 °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) 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
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
LD50 Oral - mouse - 6.500 mg/kg
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
May cause allergic skin reaction.
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 May be 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: 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
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (3,5,5-三甲基环己-2-烯亚基)丙二腈 在 哌啶 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 8.0h， 生成 [Ag((E)-2-(3-(4-(1H-imidazol-1-yl)styryl)-5,5-dimethylcyclohex-2-enylidene)malononitrile)2(CF3CO2)]*C6H6
  参考文献：
  名称：

  由基于异佛尔酮的配体生成的 银（i）超分子络合物：晶体结构和通过金属络合增强的非线性光学性质†

  摘要：

  通过（E）-2-（3-（4-（1 H-咪唑-1-基）苯乙烯基）-5,5-二甲基环己-2-烯叉基）丙二腈（L 1）和（E）-的自组装2-（3-（4-（1 H -1,2,4-三唑-1-基）苯乙烯基）-5,5-二甲基环己-2-烯叉基）丙二腈（L 2）与银（I）盐，八新的配合物，即AgL 1 2 ClO 4（1），AgL 1 2 NO 3（2），[AgL 1 2 NO 3 ]·C 6 H 6（3），[AgL1 2 OOCCF 3 ]·C 6 H 6（ 4），[AgL 1 2 PF 6 ]·C 6 H 6（ 5），AgL 2 2 NO 3（ 6），[AgL 2 OOCCF 3 ] 2（ 7）和AgL 2 2 PF 6（ 8），以及对其结构特征的分析。通过配位键，Agbondsπ，Ag⋯F（或O），氢键和π，π堆积相互作用的组合来构建结构，以生成新的超分子体系结构。我们观察到复杂7的二维配位聚合物的形

  DOI：

  10.1039/c3dt52364k
• 作为产物：
  描述：

  异佛尔酮 、 丙二腈 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以94%的产率得到(3,5,5-三甲基环己-2-烯亚基)丙二腈
  参考文献：
  名称：

  一种新型的基于双氰基异佛尔酮的比例荧光探针，用于半胱氨酸的选择性检测及其在活细胞中的生物成像应用。

  摘要：

  通过使用新型的基于双氰基异佛尔酮的衍生物和丙烯酸酯部分，设计并合成了选择性和比例开启荧光探针。与高半胱氨酸（Hcy）和谷胱甘肽（GSH）相比，该探针显示出高稳定性和对半胱氨酸（Cys）的良好选择性。它还在180 s内对Cys表现出快速反应。最重要的是，590和525 nm处的荧光强度比（I590 / I525）与Cys浓度线性相关，范围为0至40μM，计算出的检出限为0.48μM。该探针还用于低细胞毒性的活HeLa细胞中细胞内半胱氨酸的生物成像。

  DOI：

  10.3390/molecules23020475
• 作为试剂：
  描述：

  2-(吡啶-4-基)乙腈 、 在 哌啶 、 (3,5,5-三甲基环己-2-烯亚基)丙二腈 作用下， 以 乙醇 为溶剂， 以85 %的产率得到
  参考文献：
  名称：

  一种烷氧基噻吩类粘度荧光探针及其制备方法和应用

  摘要：

  本发明属于荧光探针领域领域，涉及用于溶酶体靶向癌细胞的红色荧光成像探针，特别是指一种粘度敏感的荧光探针的制备方法及应用。具有式(I)结构：#imgabs0#，本发明的烷氧基噻吩类粘度荧光探针应用于多细胞生物成像以及区分正常细胞和癌细胞，对于癌症检测具有重要意义。

  公开号：

  CN116813601A

文献信息

• Substituent Group Variations Directing the Molecular Packing, Electronic Structure, and Aggregation-Induced Emission Property of Isophorone Derivatives
  作者：Zheng Zheng、Zhipeng Yu、Mingdi Yang、Feng Jin、Qiong Zhang、Hongping Zhou、Jieying Wu、Yupeng Tian

  DOI：10.1021/jo400116j

  日期：2013.4.5

  ring or aza-crown-ether group, with large Stokes shifts (>140 nm), have been synthesized and characterized. 1–4 display aggregation-induced emission behaviors, while dye 5 is highly emissive in solution but quenched in the solid state. It was found that the tuning of emission color of the isophorone-based compounds in the solid state could be conveniently accomplished by changing the terminal substituent

  一系列新的异佛尔酮衍生物（的1 - 5），收纳该杂环或氮杂冠醚基团，具有大的斯托克斯位移（> 140纳米），已经合成和表征。1 - 4显示聚集诱导的发射行为，而染料5在溶液中高发射性，但在固体状态下猝灭。已经发现，通过改变末端取代基可以方便地实现固态的基于异佛尔酮的化合物的发射颜色的调节。对溶液，水悬浮液和晶态的光物理性质及其关系进行了比较研究。的晶体学数据1 - 4指示相邻分子之间的多个分子间氢键键合相互作用的存在限制了分子内振动和旋转，使化合物1 - 4在固态强烈发射。使用扫描电子显微镜研究了不同水含量的颗粒的大小和生长过程，表明水悬浮液中较小的球形纳米颗粒有利于荧光发射。以上结果表明，取代基对它们的分子堆积，电子结构和聚集诱导的发射性质有很大的影响。此外，荧光细胞成像实验证明了5的潜在应用。
• An Endoplasmic Reticulum-Targeted Ratiometric Fluorescent Probe for the Sensing of Hydrogen Sulfide in Living Cells and Zebrafish
  作者：Wei Shu、Shunping Zang、Chong Wang、Mengxu Gao、Jing Jing、Xiaoling Zhang

  DOI：10.1021/acs.analchem.0c01623

  日期：2020.7.21

  investigations indicated that H2S plays a cytoprotective effect under endoplasmic reticulum stress. Currently, it is still a challenge to design effective methods for ratio detection of endoplasmic reticulum H2S. Herein we are the first to construct a ratiometric near-infrared fluorescent probe (M-H2S) for sensing H2S in the endoplasmic reticulum. M-H2S has high selectivity and sensitivity toward H2S (LOD =

  硫化氢（H 2 S）是许多生理过程中的内源性气态信号分子。相关研究表明，H 2 S在内质网应激下起细胞保护作用。目前，它仍然是设计为比检测面内质网H的有效方法的挑战2 S.这里我们是第一个构建比例近红外荧光探针（MH 2 S），用于感测ħ 2的内质网S上。MH 2 S具有高的选择性和灵敏度朝向ħ 2 S（LOD = 39.1纳米）。另外，MH 2 S具有优异的内质网靶向能力。而且，MH2 S为成功地利用可视化的外源性/内源性ħ 2 S IN HeLa细胞和斑马鱼。特别重要的，内源性产生的ħ 2 S为通过衣霉素诱导的内质网应激下观察。
• 2-(2′-Hydroxyphenyl)benzothiazole derivatives: Emission and color tuning
  作者：Ishpreet Kaur、Shivani、Paramjit Kaur、Kamaljit Singh

  DOI：10.1016/j.dyepig.2020.108198

  日期：2020.5

  Benzothiazole based molecular species are among the important heterocyclic compounds which are usually characterised by fluorescence that covers a wide spectral range. Herein, we present synthesis and luminescent behaviour of benzothiazole based derivatives and their rigidified boron(III) NˆO chelates. Significant tuning of emission and absorption behaviour of the compounds led us to identify compositions

  基于苯并噻唑的分子物质是重要的杂环化合物之一，通常以覆盖宽光谱范围的荧光为特征。在本文中，我们介绍了苯并噻唑基衍生物及其刚性化的硼ˆⅢˆ ＝螯合物的合成和发光行为。化合物的发射和吸收行为的显着调整使我们能够鉴定出这些分子种类在溶液（CIE坐标：x = 0.35753，y = 0.3315）和固体中（CIE坐标：x）发出的互补色的组成＝ 0.34753，y ＝ 0.32062）状态提供近乎白光的发射。这项工作涉及结构简单且易于合成的，具有不同发射特性（尤其是固态）的分子物种，
• 一种单波长激发区分检测GSH和多硫化氢的荧光探针
  申请人：郑州大学

  公开号：CN111635386B

  公开（公告）日：2022-05-10

  本发明公布了一种单激发区分检测GSH和H2Sn(n>1)的荧光探针，属于化学分析检测技术领域，其分子结构式如下：该探针与GSH反应后发出绿色荧光，与H2Sn反应后发出红色荧光。该探针在单波长激发下即可实现对GSH和H2Sn(n>1)的同时区分检测，而且具有较好的选择性、高灵敏度、较宽的pH工作范围等特点。同时，在检测过程中该探针能发射出红色荧光。这些优良的性能表明该荧光探针在环境及生物等领域具有重要的应用价值。
• Effect of substitution on the solid-state fluorescence properties of styrylbenzoxazole derivatives with terminal dicyanomethylene group
  作者：Emma Bremond、Nadine Leygue、Thomas Jaouhari、Nathalie Saffon-Merceron、Arnaud Erriguible、Suzanne Fery-Forgues

  DOI：10.1016/j.jphotochem.2020.112857

  日期：2021.1

  styrylbenzoxazole derivatives with terminal dicyanomethylene group were studied in order to understand how minor modifications brought to the benzoxazole ring influence the photoluminescence (PL) properties. The three compounds, in which several molecular motions are allowed, were weakly fluorescent in organic solution. Remarkably, the unsubstituted (1) and methoxy (2) derivatives showed clear solid-state

  为了了解带有苯并恶唑环的微小修饰如何影响光致发光（PL）性能，对三种带有末端二氰基亚甲基的苯乙烯基苯并恶唑衍生物进行了研究。允许几种分子运动的这三种化合物在有机溶液中的荧光较弱。值得注意的是，未取代的（1）和甲氧基（2）衍生物显示出明显的固态发光增强（SLE）。由于扫描电子显微镜，不同的发射特性归因于非晶和结晶颗粒的形成。这两种化合物也以微晶粉末的形式强烈发光。化合物1根据X射线衍射分析，以人字形构型结晶的是比甲氧基衍生物2更好的发射体，后者之间的分子间相互作用更多。相反，化合物3实际上是不发光的，证实了在这一系列染料中，羟基的存在对PL发射有害，这在SLE活性荧光团中很少见到。