环己烯-D10 - CAS号 1603-55-0

物化性质

熔点：

-104 °C (lit.)
沸点：

83 °C (lit.)
密度：

0.908 g/mL at 25 °C
闪点：

10 °F
溶解度：

氯仿（微溶）、己烷（微溶）

计算性质

辛醇/水分配系数(LogP)：

2.9
重原子数：

6
可旋转键数：

0
环数：

1.0
sp3杂化的碳原子比例：

0.67
拓扑面积：

0
氢给体数：

0
氢受体数：

0

安全信息

WGK Germany：

2
危险品标志：

F,Xi
安全说明：

S16,S26,S36/37/39
危险类别码：

R11,R36/37/38
危险品运输编号：

UN 2256 3/PG 2
储存条件：

室温

SDS

SDS：54ef96933bd13845469b110d92b4924d

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Cyclohexene-d10
CAS-No. : 16035-50-0
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]
Flammable liquids (Category 2)
Acute toxicity, Oral (Category 4)
Acute toxicity, Dermal (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Highly flammable. Harmful in contact with skin and if swallowed.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Danger
Hazard statement(s)
H225 Highly flammable liquid and vapour.
H302 Harmful if swallowed.
H311 Toxic in contact with skin.
Precautionary statement(s)
P210 Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P280 Wear protective gloves/ protective clothing.
P312 Call a POISON CENTER or doctor/ physician if you feel unwell.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R11 Highly flammable.
R21/22 Harmful in contact with skin and if swallowed.
S-phrase(s)
S16 Keep away from sources of ignition - No smoking.
S29 Do not empty into drains.
S33 Take precautionary measures against static discharges.
S36/37 Wear suitable protective clothing and gloves.
Other hazards - none

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C6D10
Molecular Weight : 92,21 g/mol
Component Concentration
Cyclohexene-d10
CAS-No. 16035-50-0 -

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. Take victim immediately to hospital. 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
Exposure to high airborne concentrations can cause anesthetic effects., Nausea, Dizziness, Headache,
Central nervous system depression
Indication of any immediate medical attention and special treatment needed
no data available

Section 5. FIRE-FIGHTING 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
no data available
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
Wear respiratory protection. 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. Discharge into the
environment must be avoided.
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).
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.
Store under inert gas. hygroscopic
Specific end uses
no data available

Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the
product.
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, Flame retardant antistatic protective 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).

Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: liquid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: -104 °C - lit.
point
f) Initial boiling point and 83 °C - lit.
boiling range
g) Flash point -12 °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 0,908 g/mL at 25 °C0,908 g/cm3 at 25 °C
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 3,27
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

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. Extremes of temperature and direct sunlight.
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
LD50 Oral - rat - 1.940 mg/kg
LD50 Oral - rat - 1.944 mg/kg
Remarks: Behavioral:Somnolence (general depressed activity). Behavioral:Tremor. Behavioral:Ataxia.
LD50 Oral - mouse - > 2.592 mg/kg
Remarks: Behavioral:Altered sleep time (including change in righting reflex). Behavioral:Ataxia.
Behavioral:Somnolence (general depressed activity).
LD50 Dermal - rabbit - > 200 mg/kg
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 May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin Toxic if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Signs and Symptoms of Exposure
Exposure to high airborne concentrations can cause anesthetic effects., Nausea, Dizziness, Headache,
Central nervous system depression
Additional Information
RTECS: Not available

Section 12. ECOLOGICAL INFORMATION
Toxicity
Toxicity to fish LC50 - Poecilia reticulata (guppy) - 7,1 mg/l - 96 h
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
Toxic to aquatic life.

Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as
this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal
company.
Contaminated packaging
Dispose of as unused product.

Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: 2256 IMDG: 2256 IATA: 2256
UN proper shipping name
ADR/RID: CYCLOHEXENE
IMDG: CYCLOHEXENE
IATA: Cyclohexene
Transport hazard class(es)
ADR/RID: 3 IMDG: 3 IATA: 3
Packaging group
ADR/RID: II IMDG: II IATA: II
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 2011 Co. 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. Co., shall not be held liable for any damage
resulting from handling or from contact with the above product. See 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：

环己烯-D10 在甲基三氧化铼(VII) 双氧水作用下，以 various solvent(s) 为溶剂，生成 C₆H₂⁽²⁾H₁₀O₂

参考文献：

名称：

环境温度离子液体中MTO催化烯烃环氧化的动力学：UV / Vis和2H NMR研究。

摘要：

研究了从离子液体中甲基三氧杂or（MTO）的过氧配合物到烯烃的氧原子转移动力学。在360 nm处通过UV / Vis监测烯烃到环氧化物的非催化转化，单过氧or（mpRe）和二过氧or（dpRe）络合物在其中吸收。通过MTO和尿素过氧化氢（UHP）在无水THF中的反应原位制备无水和无过氧化物的dpRe。观察到的双指数时间曲线与动力学模型相结合，可以将快速步骤分配给烯烃与dpRe（k4）的反应，将缓慢步骤分配给与mpRe（k3）的类似反应。在大多数的离子液体中，k4约为5 x k3。在非稳态条件下用[D3] dpRe进行的2H NMR实验证实了离子液体中催化体系的形态，并证明了UV / Vis动力学的有效性。用氘代烯烃通过2 H NMR光谱研究烯烃的催化环氧化和二羟基化。在几种离子液体中，α-甲基苯乙烯的k4值比乙腈中的k4值高一个数量级。尽管烯烃环氧化的速率不受离子液体阳离子的性质影响，但观

DOI：

10.1002/1521-3765(20020703)8:13<3053::aid-chem3053>3.0.co;2-g
作为产物：

描述：

环己烯在 tris(triphenylphosphine)ruthenium(II) chloride 、重水作用下，反应 1.0h，生成环己烯-D10

参考文献：

名称：

Pd-η³-C₆H₉ complexes of the Trost modular ligand: high nuclearity columnar aggregation controlled by concentration, solvent and counterion

摘要：

Pd-η³-C₆H₉ 阳离子与Trost配体（2）发生两阶段齐聚-聚集，形成高核聚集物（最多56个Pd中心），聚集过程受到浓度、溶剂和反离子的强烈调控。

DOI：

10.1039/c5sc01181g
作为试剂：

描述：

(E)-3-phenylbut-2-en-1-ol 在环己烯-D10 、 C₂₇H₄₇ClP₂Pd 、四(3,5-二(三氟甲基)苯基)硼酸钠作用下，以 1,2-二氯乙烷为溶剂，反应 24.0h，生成

参考文献：

名称：

钯催化高度取代的烯丙醇、高烯丙醇和烯基醇异构化的范围和机制

摘要：

在此，我们报告了通过单一催化体系钯催化的高度取代的烯丙醇和链烯醇的异构化。操作简单的反应方案适用于广泛的底物，并显示出广泛的官能团耐受性，并且产物通常以高化学产率分离。实验和计算机制研究为由重复迁移插入/β-H 消除序列组成的链行走过程提供了补充和收敛的证据。有趣的是，在烯丙醇异构化过程中，催化剂不会从底物上解离，而当烷基链上存在额外的取代基时，它会在烯醇异构化过程中脱离。

DOI：

10.1021/ja508736u

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文献信息

Mn(III)-Iodosylarene Porphyrins as an Active Oxidant in Oxidation Reactions: Synthesis, Characterization, and Reactivity Studies

作者：Mian Guo、Yong-Min Lee、Mi Sook Seo、Yong-Ju Kwon、Xiao-Xi Li、Takehiro Ohta、Won-Suk Kim、Ritimukta Sarangi、Shunichi Fukuzumi、Wonwoo Nam

DOI：10.1021/acs.inorgchem.8b01426

日期：2018.8.20

+ species were then investigated in the epoxidation of olefins under stoichiometric conditions. In the epoxidation of olefins by the Mn(III)-iodosylarene porphyrin species, epoxide was formed as the sole product with high chemoselectivities and stereoselectivities. For example, cyclohexene oxide was formed exclusively with trace amounts of allylic oxidation products; cis- and trans-stilbenes were oxidized

Mn（III）-碘亚芳基卟啉加合物[Mn（III）（ArIO）（Porp）] +通过使缺电子的Mn（III）卟啉配合物与碘亚芳基（ArIO）在-60°C下反应而合成光谱方法。然后在化学计量条件下在烯烃的环氧化中研究了[Mn（III）（ArIO）（Porp）] +物质。在Mn（III）-碘亚芳基卟啉物种对烯烃的环氧化中，形成环氧化物作为具有高化学选择性和立体选择性的唯一产物。例如，环己烯氧化物仅与痕量的烯丙基氧化产物形成；顺式-和反式-斯蒂尔苯被氧化成相应的顺式和反式-二苯乙烯氧化物。缺电子的Mn（III）卟啉配合物和s在环己烯的催化环氧化中在低温（例如-60°C）下的PhIO中，Mn（III）-碘亚芳基卟啉物种被证明是一种有效的氧化剂，可影响烯烃的环氧化以提供环氧化物作为产物。但是，在高温（例如0°C）下或在使用富电子的锰（III）卟啉催化剂的情况下，会生成烯丙基氧化产物以及环己烯氧化物，
Formation of cobalt–oxygen intermediates by dioxygen activation at a mononuclear nonheme cobalt(<scp>ii</scp>) center

作者：Deesha D. Malik、Anirban Chandra、Mi Sook Seo、Yong-Min Lee、Erik R. Farquhar、Stefan Mebs、Holger Dau、Kallol Ray、Wonwoo Nam

DOI：10.1039/d1dt01996a

日期：——

[(TMG3tren)CoII(OTf)](OTf) (1), activates dioxygen in the presence of hydrogen atom donor substrates, such as tetrahydrofuran and cyclohexene, resulting in the generation of a cobalt(II)-alkylperoxide intermediate (2), which then converts to the previously reported cobalt(IV)-oxo complex, [(TMG3tren)CoIV(O)]2+-(Sc(OTf)3)n (3), in >90% yield upon addition of a redox-inactive metal ion, Sc(OTf)3. Intermediates

单核非血红素钴 ( II ) 络合物 [(TMG 3 tren)Co II (OTf)](OTf) ( 1 ) 在氢原子供体底物（例如四氢呋喃和环己烯）存在下活化双氧，从而生成钴( II )-烷基过氧化物中间体 ( 2 )，然后转化为先前报道的钴( IV )-氧代络合物，[(TMG 3 tren)Co IV (O)] 2+ -(Sc(OTf) 3 ) n ( 3 )，添加氧化还原惰性金属离子Sc(OTf) 3后产率>90% 。中间体2和3代表所提出的铁( II )-烷基过氧化物前体的钴类似物，其在蝶呤依赖性非血红素铁加氧酶中通过O-O键杂解转化为铁( IV )-氧代中间体。在反应性研究中，2在亲电和亲核反应中显示出两性反应性，而3是亲电氧化剂。据我们所知，本研究报道了第一个例子，显示通过激活钴（II）中心的分子氧生成钴-氧中间体，以及钴-氧中间体在氧化反应中的反应性。
Mononuclear Nonheme High-Spin Iron(III)-Acylperoxo Complexes in Olefin Epoxidation and Alkane Hydroxylation Reactions

作者：Bin Wang、Yong-Min Lee、Martin Clémancey、Mi Sook Seo、Ritimukta Sarangi、Jean-Marc Latour、Wonwoo Nam

DOI：10.1021/jacs.5b13500

日期：2016.2.24

and trans-stilbene oxides, respectively. In the epoxidation of cyclohexene, cyclohexene oxide was formed as the major product with a kinetic isotope effect (KIE) value of 1.0, indicating that nonheme iron(III)-acylperoxo complexes prefer C═C epoxidation to allylic C-H bond activation. Olefin epoxidation by chiral iron(III)-acylperoxo complexes afforded epoxides with high enantioselectivity, suggesting

合成、光谱表征和烯烃环氧化和烷烃羟基化反应中的单核非血红素高自旋铁 (III)-acylperoxo 配合物的 N-甲基化环烷烃配体。在烯烃的环氧化中，主要产物环氧化物具有较高的立体选择性、化学选择性和对映选择性；顺式和反式二苯乙烯分别被氧化成顺式和反式二苯乙烯氧化物。在环己烯的环氧化中，氧化环己烯作为主要产物形成，动力学同位素效应 (KIE) 值为 1.0，表明非血红素铁 (III)-酰基过氧配合物更喜欢 C=C 环氧化而不是烯丙基 CH 键活化。手性铁（III）-酰基过氧配合物对烯烃的环氧化反应提供了具有高对映选择性的环氧化物，表明铁（III）-酰基过氧物种，不是高价铁氧物种，是环氧化剂。在烷烃羟基化反应中，铁（III）-酰基过氧化合物与环己烷中的 CH 键在 -40 °C 时的强度一样强，其中（a）醇作为主要产物产生，具有高区域选择性和立体选择性，（b）活化铁（III）-酰基过氧物种的
Mononuclear Nonheme High-Spin (S =2) versus Intermediate-Spin (S =1) Iron(IV)-Oxo Complexes in Oxidation Reactions

作者：Seong Hee Bae、Mi Sook Seo、Yong-Min Lee、Kyung-Bin Cho、Won-Suk Kim、Wonwoo Nam

DOI：10.1002/anie.201603978

日期：2016.7.4

nonheme intermediate (S=1) iron(IV)–oxo complexes. We also report that C−H bond activation is preferred over C=C epoxidation in the oxidation of cyclohexene by the nonheme high‐spin (HS) and intermediate‐spin (IS) iron(IV)–oxo complexes, whereas the C=C double bond epoxidation becomes a preferred pathway in the oxidation of deuterated cyclohexene by the nonheme HS and IS iron(IV)–oxo complexes. In the

单核非血红素高自旋（S = 2）铁（IV）-氧代已被确定为负责非血红素铁酶促反应中有机底物C-H键活化的关键中间体。本文中，我们报道了合成的单核非血红素高旋压（S = 2）铁（IV）-氧代复合物通过碳的非反弹机理发生的碳氢键活化反应，如先前在碳氢键中所证明的那样。活化非血红素中间体（小号= 1）铁（IV）-氧杂配合物。我们还报告说，通过非血红素高自旋（HS）和中自旋（IS）铁（IV）-氧代络合物氧化环己烯时，在C = C环氧化反应中C–H键活化比C = C环氧化更可取，而C = C双键环氧化成为非血红素HS和IS铁（IV）-氧代配合物氧化氘代环己烯的优选途径。在苯乙烯衍生物的环氧化中，发现HS和IS铁（IV）氧配合物具有相似的亲电子特性。
Structure-Based Rationale for Selectivity in the Asymmetric Allylic Alkylation of Cycloalkenyl Esters Employing the Trost ‘Standard Ligand’ (TSL): Isolation, Analysis and Alkylation of the Monomeric form of the Cationic η3-Cyclohexenyl Complex [(η3-c-C6H9)Pd(TSL)]+

作者：Craig P. Butts、Emane Filali、Guy C. Lloyd-Jones、Per-Ola Norrby、David A. Sale、York Schramm

DOI：10.1021/ja8099757

日期：2009.7.29

explored computationally. The concave orientated amide N-H is able to activate the leaving group of the allylic ester by hydrogen bonding to its carbonyl group. However, this interaction is only feasible for the (S)-enantiomer of substrate, leading to the prediction of a powerful kinetic resolution (k(S) >> k(R)), as is found experimentally. This new model involving two regiochemically distinct (NH)

阳离子 Pd-eta(3)-烯丙基和 Pd-eta(3)-环己烯基配合物 [Pd(R,R)-1(eta(3)-C(3)H) 单体形式的溶液相结构(5))](+) (7(+)) 和 [Pd(R,R)-1(eta(3)-C(6)H(9))](+) (8(+)) 轴承已通过核磁共振、同位素标记和计算阐明了基于反式环己二胺的 Trost '标准配体' (R,R)-1。在这两种复合物中，(R,R)-1 被发现采用 C(1) 对称构象，导致 13 元螯合物中的凹形，其中手性支架中的一个酰胺基团将其 NH 单元伸出靠近一个烯丙基末端的凹面。相邻的酰胺具有相反的取向，并将其羰基突出到相对烯丙基末端附近的凹面之外。MCHE(2) 对 [8(+)][X(-)] 的化学计量和催化不对称烷基化（E = 酯，M = '护送'反离子，X = Pd 烯丙基反离子）显示出与原位生成催化剂相同的选择性和趋势，并且已经通过计

环己烯-D10 | 1603-55-0

分子结构分类

物化性质

计算性质

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