2,4,6-环庚三烯-1-甲腈 | 13612-59-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2,4,6-环庚三烯-1-甲腈
• 中文别名: 7-氰基环庚三烯
• 英文名称: cyclohepta-2,4,6-triene-1-carbonitrile
• 英文别名: 7-cyanocycloheptatriene；7-cyano-1,3,5-cycloheptatriene；7-Cyanocycloheptatrien；cyclohepta-2,4,6-trienecarbonitrile；7-Cyan-cycloheptatrien；2,4,6-Cycloheptatriene-1-carbonitrile
• CAS: 13612-59-4
• 化学式: C₈H₇N
• mdl: MFCD00191965
• 分子量: 117.15
• InChiKey: LADCKIXFXIKHQM-UHFFFAOYSA-N

物化性质

• 沸点：
  51-53 °C/1.5 mmHg (lit.)
• 密度：
  1.017 g/mL at 25 °C (lit.)
• 闪点：
  185 °F

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R20/21/22
• 危险品运输编号：
  NA 1993 / PGIII
• WGK Germany：
  3
• 海关编码：
  2926909090
• 安全说明：
  S36
• 储存条件：
  2-8°C，干燥密封保存。

SDS

---

Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 2,4,6-Cycloheptatriene-1-carbonitrile
CAS-No. : 13612-59-4
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

---

Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Acute toxicity, Inhalation (Category 4)
Acute toxicity, Dermal (Category 4)
Acute toxicity, Oral (Category 4)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful by inhalation, in contact with skin and if swallowed.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
H312 Harmful in contact with skin.
H332 Harmful if inhaled.
Precautionary statement(s)
P280 Wear protective gloves/ protective clothing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R20/21/22 Harmful by inhalation, in contact with skin and if swallowed.
S-phrase(s)
S36 Wear suitable protective clothing.
Other hazards - none

---

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C8H7N
Molecular Weight : 117,15 g/mol
Component Concentration
2,4,6-Cycloheptatriene-1-carbonitrile
CAS-No. 13612-59-4 -

---

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
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

---

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, nitrogen oxides (NOx), Hydrogen cyanide (hydrocyanic acid)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
Use water spray to cool unopened containers.

---

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. 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.

---

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.
Specific end use(s)
no data available

---

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
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).

---

Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: liquid
Colour: light yellow
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 51 - 53 °C at 2,0 hPa - lit.
boiling range
g) Flash point 85 °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 1,017 g/cm3 at 25 °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

---

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

---

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 Harmful if inhaled. May cause respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin 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

---

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

---

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.

---

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

---

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

---

Section 16. OTHER INFORMATION
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：

  2,4,6-环庚三烯-1-甲腈 在 盐酸 、 sodium hydroxide 、 sodium hypochlorite 、 氯化亚砜 作用下， 以 叔丁醇 为溶剂， 反应 35.0h， 生成 8-甲基-8-氮杂二环[3.2.1]辛烷-2-酮
  参考文献：
  名称：

  氮杂双环化合物的溶剂化重排。第2部分。动力学

  摘要：

  已经研究了三种2- exo - chloroazabicyclocycloanes在乙醇水溶液和二恶烷水溶液中的溶剂分解速率，并得出了一级速率常数，并将其与类似化合物的公开值进行了比较。在这些重排的速率控制步骤中，桥N原子的邻氨基苯甲酸酯辅助显然并不重要，尽管在2 - exo -chloro-7-甲基-7-azanorbornane的情况下可能很小。还报道了在乙醇水溶液和丙酮水溶液混合物中的tropan-2β-甲苯基对磺酸盐的溶剂化结果，并将其与碳双环和氧双环类似物的文献数据进行了比较。

  DOI：

  10.1039/p19810001346
• 作为产物：
  描述：

  (1S,2S,3S,6S)-7-cyano-2-hydroxybicyclo[4.1.0]hept-4-en-3-yl carbamimidothioate sulfate 在 pH₈ buffer solution 作用下， 生成 2,4,6-环庚三烯-1-甲腈
  参考文献：
  名称：

  cis- Aza-/Oxa- bis-σ-homobenzenes - dihydroazocines / hydrooxocins

  摘要：

  DOI：

  10.1016/s0040-4039(00)95455-8

文献信息

• Synthetic Studies on Cyathin Terpenoids: Enantioselective Synthesis of the Tricyclic Core of Cyathin through Intramolecular Heck Cyclisation
  作者：Emmanuelle Drège、Cyrille Tominiaux、Georges Morgant、Didier Desmaële

  DOI：10.1002/ejoc.200600429

  日期：2006.11

  An enantioselective synthesis of the tricyclic ketone (+)-5, which displays the carbon core of NGF-inducing cyathane diterpenes, has been completed according to a strategy in which the key step was the intramolecular Heck reaction of the AC subunit 49 establishing the crucial anti stereochemical relationship between the two angular substituents. The C-9 quaternary centre was set up by taking advantage

  三环酮 (+)-5 的对映选择性合成，显示了 NGF 诱导的氰基二萜的碳核心，已根据一种策略完成，其中关键步骤是 AC 亚基 49 的分子内 Heck 反应建立关键的两个角取代基之间的反立体化学关系。C-9 四元中心是通过利用涉及手性亚胺的对映选择性迈克尔加成建立的，提供 91% ee 的酮酯 (R)-10。在丙酸酯侧链引入异丙基和碘脱羧基后，碘酮 39 与二氢苯甲酸甲酯的烯醇锂缩合得到 AC 亚基 43，该亚基进一步细化为三氟甲磺酸酯 (-)-22。虽然 22 的直接 Heck 环化是无效的，1,4-环己二烯部分的双（烯丙基）位置的氧化增强了反应性，允许立体选择性地形成六氢-环戊二烯（+）-50a。该结构的一个关键要素是最终的 C 环扩大，涉及三甲基铝促进酮 52 与三甲基甲硅烷基重氮甲烷的单碳膨胀，提供三环酮 (+)-5。此外，三烯酮 (+)-50a 的环氧化反应仅发生在 β 面上，产生
• Synthesis of new <scp>Schiff</scp> bases; Investigation of their in situ catalytic activity for Suzuki <scp>CC</scp> coupling reactions and antioxidant activities
  作者：Özgür Yılmaz

  DOI：10.1002/jccs.202000433

  日期：2021.5

  obtained in Et3N and EtOH. In addition to catalytic investigations, antioxidant activities of all synthesized Schiff bases were examined using DPPH and Iron (Fe2+) chelation methods, and IC50 values were calculated. While many molecules show various amounts of antioxidant activity, especially molecules 8e and 8g showed the best activity compared to butylated hydroxytoluene (BHT) and butylated hydroxyanisole

  通过环庚2,4,6-三烯-1-基甲胺与不同醛的反应合成了一系列新的席夫碱，并通过1 H NMR，13 C NMR，FTIR光谱和GC-MS对其进行了表征。成功合成后，已使用苯基硼酸，芳基溴化物和PdCl 2作为催化剂，检查了所有Schiff碱在SuzukiCC交叉偶联反应中的原位催化活性。在开始这些研究之前，使用不同的碱和溶剂优化反应条件。在这些反应结束时，在Et 3中获得了最佳效率N和EtOH。除了进行催化研究外，还使用DPPH和铁（Fe 2+）螯合方法检查了所有合成的席夫碱的抗氧化活性，并计算了IC 50值。尽管许多分子显示出不同程度的抗氧化活性，但与分别用作DPPH和铁螯合方法的阳性对照的丁基化羟基甲苯（BHT）和丁基化羟基茴香醚（BHA）相比，分子8e和8g表现出最佳的活性。
• PIPERIDINE DERIVATIVE, LIQUID CRYSTAL COMPOSITION AND LIQUID CRYSTAL DISPLAY DEVICE
  申请人：JNC CORPORATION

  公开号：US20170158961A1

  公开（公告）日：2017-06-08

  Provided is a compound having an effect on preventing photolysis of a liquid crystal composition and having a high solubility in the liquid crystal composition, a liquid crystal composition containing the compound and a liquid crystal display device including the composition. The compound is represented by formula (1), the liquid crystal composition contains the compound, and the liquid crystal display device uses the composition. In formula (1), R 1 , R 2 , R 3 and R 4 are independently hydrogen or alkyl having 1 to 4 carbons; R 5 is hydrogen, hydroxy, oxy radical, alkyl having 1 to 10 carbons or alkoxy having 1 to 10 carbons; ring A 1 is 1,4-cyclohexylene, 1,4-cyclohexenylene or the like; Z 1 and Z 2 are independently a single bond or alkylene having 1 to 10 carbons; and a is 0, 1, 2 or 3.

  提供一种对防止液晶组合物的光解具有影响并且在液晶组合物中具有高溶解度的化合物，一种含有该化合物的液晶组合物以及包括该组合物的液晶显示装置。该化合物由公式（1）表示，液晶组合物含有该化合物，液晶显示装置使用该组合物。在公式（1）中，R1、R2、R3和R4独立地为氢或具有1至4个碳原子的烷基；R5为氢、羟基、氧自由基、具有1至10个碳原子的烷基或具有1至10个碳原子的烷氧基；环A1为1,4-环己基、1,4-环己烯基或类似物；Z1和Z2独立地为单键或具有1至10个碳原子的烷基；a为0、1、2或3。
• Base-catalyzed 1-3 Prototropic Isomerization of Cycloheptatrienes
  作者：Kazuko Takahashi、Hiroshi Yamamoto、Tetsuo Nozoe

  DOI：10.1246/bcsj.43.200

  日期：1970.1

  resulting carbanion to the allylic position (the rate-determining step), and iii) the recovery of a proton from the solvent. The kinetic study of the isomerization of 7-carboxycycloheptatriene (Ia) discloses the rate of the isomerization (k[the cycloheptatriene][base]) and the parameters (Ea=22.6 kcal/mol, ΔH\eweq=22.0 kcal/mol, ΔS\eweq=−15.4 e.u. at 60°). The structure of the cycloheptatrienyl anions formed

  在氢氧化钠水溶液或氢氧化钾水溶液介质中研究了带有吸电子基团的环庚三烯的碱催化质子迁移（从 7 位到 2 位）和质子交换（在 7 位）。各种取代基对相对速率的影响顺序约为：CN>CONH2>COO-，Ph。碱催化的质子异构化通过以下方式进行：i) 碱对 7 位质子的提取， ii) 生成的碳负离子迁移到烯丙基位置（速率决定步骤），以及 iii) 从溶剂中回收质子。7-羧基环庚三烯（Ia）异构化的动力学研究公开了异构化速率（k[环庚三烯][碱]）和参数（Ea=22.6 kcal/mol，ΔH\eweq=22.0 kcal/mol，ΔS\eweq=−15.4 eu 在 60°）。讨论了作为中间体形成的环庚三烯基阴离子的结构。
• Cycloheptatriene and tropylium metal complexes. Part V. 7-endo-Substituted tricarbonylcycloheptatrienechromiums
  作者：P. L. Pauson、G. H. Smith、J. H. Valentine

  DOI：10.1039/j39670001061

  日期：——

  Reaction of 7-substituted cycloheptatrienes with either hexacarbonylchromium or with tricarbonyltripyridine-chromium leads to the corresponding 7-endo-substituted tricarbonylcycloheptatrienechromiums, either exclusively or, in only two of the cases studied, mixed with the exo-isomer. Some new observations on the ring-contraction of such complexes are reported.

  7-取代的环庚烯与六羰基铬或与三羰基三吡啶-铬的反应导致相应的7-内取代的三羰基环庚三烯铬单独地或仅在所研究的两种情况下与外消旋异构体混合。据报道有关这种配合物的环收缩的一些新观察。

表征谱图