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全氘代环己烷 | 1735-17-7

中文名称
全氘代环己烷
中文别名
环己烷-d12;环已烷;氘代环已烷-d12
英文名称
Cyclohexane-d12
英文别名
d12-cyclohexane;cyclohexane;1,1,2,2,3,3,4,4,5,5,6,6-dodecadeuteriocyclohexane
全氘代环己烷化学式
CAS
1735-17-7
化学式
C6H12
mdl
——
分子量
96.066
InChiKey
XDTMQSROBMDMFD-LBTWDOQPSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    6.5°C
  • 沸点:
    80.7 °C(lit.)
  • 密度:
    0.893 g/mL at 25 °C(lit.)
  • 闪点:
    −1 °F
  • 溶解度:
    55mg/l不溶物
  • 保留指数:
    661
  • 稳定性/保质期:
    在常温常压下保持稳定,应避免与氧化物接触。

计算性质

  • 辛醇/水分配系数(LogP):
    3.4
  • 重原子数:
    6
  • 可旋转键数:
    0
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    1.0
  • 拓扑面积:
    0
  • 氢给体数:
    0
  • 氢受体数:
    0

ADMET

毒理性
  • 副作用
神经毒素 - 急性溶剂综合症
Neurotoxin - Acute solvent syndrome
来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

安全信息

  • 危险等级:
    3
  • 危险品标志:
    Xn,F,N
  • 安全说明:
    S16,S25,S33,S60,S61,S62,S9
  • 危险类别码:
    R65,R50/53,R11,R38
  • WGK Germany:
    3
  • 海关编码:
    29021100
  • 包装等级:
    II
  • 危险类别:
    3
  • 危险品运输编号:
    UN 1145 3/PG 2
  • 危险标志:
    GHS02,GHS07,GHS08,GHS09
  • 危险性描述:
    H225,H304,H315,H336,H410
  • 危险性防范说明:
    P210,P261,P273,P301 + P310,P331,P501
  • 储存条件:
    请将容器密封保存,并存放在阴凉、干燥的地方。

SDS

SDS:617188706e9a9d1afa81a58e195c5dcc
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Name: Cyclohexane-D12 99.5 Atom % D Material Safety Data Sheet
Synonym: None
CAS: 1735-17-7
Section 1 - Chemical Product MSDS Name:Cyclohexane-D12 99.5 Atom % D Material Safety Data Sheet
Synonym:None

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
CAS# Chemical Name content EINECS#
1735-17-7 Cyclohexane-D12 99.5 217-077-3
Hazard Symbols: XI F
Risk Phrases: 11 36/37/38

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Highly flammable. Irritating to eyes, respiratory system and skin.The toxicological properties of this material have not been fully investigated.Hygroscopic (absorbs moisture from the air).Highly flammable.
Potential Health Effects
Eye:
May cause mild eye irritation. Causes eye irritation.
Skin:
Causes skin irritation. May be absorbed through the skin in harmful amounts. May cause irritation with burning pain, itching and redness. The toxicological properties of this material have not been fully investigated.
Ingestion:
Ingestion of large amounts may cause gastrointestinal irritation.
Causes gastrointestinal irritation with nausea, vomiting and diarrhea. May cause liver and kidney damage. May cause central nervous system depression, characterized by excitement, followed by headache, dizziness, drowsiness, and nausea. Advanced stages may cause collapse, unconsciousness, coma and possible death due to respiratory failure. May cause vascular collapse and damage. The toxicological properties of this substance have not been fully investigated. Aspiration of material into the lungs may cause chemical pneumonitis, which may be fatal.
Inhalation:
Inhalation of high concentrations may cause central nervous system effects characterized by nausea, headache, dizziness, unconsciousness and coma. Causes respiratory tract irritation. May cause respiratory tract irritation. Irritation may lead to chemical pneumonitis and pulmonary edema. May be fatal if exposed to high concentrations. May cause pulmonary edema and severe respiratory disturbances. Vapors may cause dizziness or suffocation.
Chronic:
Prolonged or repeated skin contact may cause defatting and dermatitis. May cause liver and kidney damage.

Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid. Do NOT allow victim to rub eyes or keep eyes closed.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists. Wash clothing before reuse.
Ingestion:
Do not induce vomiting. If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Possible aspiration hazard. Get medical aid immediately. 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. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
Notes to Physician:
Treat symptomatically and supportively.

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. Vapors may form an explosive mixture with air.
Vapors can travel to a source of ignition and flash back. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Extremely flammable. Material will readily ignite at room temperature. Use water spray to keep fire-exposed containers cool. Water may be ineffective. Material is lighter than water and a fire may be spread by the use of water.
Liquid will float and may reignite on the surface of water.
Flammable liquid and vapor. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
May polymerize explosively when involved in a fire. Will be easily ignited by heat, sparks or flame. Containers may explode when heated.
Containers may explode if exposed to fire.
Extinguishing Media:
For small fires, use dry chemical, carbon dioxide, water spray or alcohol-resistant foam. Water may be ineffective. Water may spread fire. This material is lighter than water and insoluble in water. The fire could easily be spread by the use of water in an area where the water cannot be contained. If water is the only media available, use in flooding amounts. For large fires, use water spray, fog or alcohol-resistant foam. Do NOT use straight streams of water. For large fires, use water spray, fog or regular foam. For small fires, use dry chemical, carbon dioxide, water spray or regular foam. Cool containers with flooding quantities of water until well after fire is out.

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. Wear a self contained breathing apparatus and appropriate personal protection. (See Exposure Controls, Personal Protection section).
Scoop up with a nonsparking tool, then place into a suitable container for disposal. Remove all sources of ignition. Provide ventilation.

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use only in a well-ventilated area. Ground and bond containers when transferring material. Use spark-proof tools and explosion proof equipment. Do not reuse this container. Avoid breathing dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Keep away from heat, sparks and flame. Do not get on skin or in eyes.
Avoid ingestion and inhalation. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.
Storage:
Keep away from heat and flame. Keep away from sources of ignition.
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
Flammables-area.

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. Use adequate general or local exhaust ventilation to keep airborne concentrations below the permissible exposure limits.
Exposure Limits CAS# 1735-17-7: 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 neoprene gloves, apron, and/or clothing. Wear nitrile-latex gloves, apron, and/or clothing. Use polyvinyl alcohol or fluorocarbon rubber (viton) gloves.
Clothing:
Wear nitrile-latex gloves, apron, and/or 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.

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: colorless
Odor: sweetish odor - chloroform-like
pH: Not available.
Vapor Pressure: 95 mm Hg
Viscosity: 1.02 cP at 63F.
Boiling Point: 80.7 deg C
Freezing/Melting Point: 6.5 deg C
Autoignition Temperature: 245 deg C ( 473.00 deg F)
Flash Point: -20 deg C ( -4.00 deg F)
Explosion Limits, lower: 1.3
Explosion Limits, upper: 8.0
Decomposition Temperature: Not available.
Solubility in water: Practically insoluble in water.
Specific Gravity/Density: 0.8 (Water=1)
Molecular Formula: CH2(CH2)4CH2
Molecular Weight: 84.084

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Mechanical shock, incompatible materials, ignition sources, excess heat, exposure to moist air or water, oxidizers.
Incompatibilities with Other Materials:
Strong oxidizing agents, nitrogen dioxide.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1735-17-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Cyclohexane-D12 - Not listed by ACGIH, IARC, or NTP.

Section 12 - ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: Fathead Minnow: LC50 = 117.0 mg/L; 96 Hr.; Static conditionsFish: Bluegill/Sunfish: LC50 = 34.72 mg/L; 96 Hr.; 25 degrees CWater flea Daphnia: EC50 = 400.00 mg/L; 48 Hr.; UnspecifiedBacteria: Phytobacterium phosphoreum: EC50 = 227.00 mg/L; 5, 30 minutes; Microtox test

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: CYCLOHEXANE
Hazard Class: 3
UN Number: 1145
Packing Group: II
IMO
Shipping Name: CYCLOHEXANE
Hazard Class: 3.1
UN Number: 1145
Packing Group: II
RID/ADR
Shipping Name: CYCLOHEXANE
Hazard Class: 3
UN Number: 1145
Packing group: II

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI F
Risk Phrases:
R 11 Highly flammable.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 9 Keep container in a well-ventilated place.
S 16 Keep away from sources of ignition - No
smoking.
S 28A After contact with skin, wash immediately with
plenty of water.
S 33 Take precautionary measures against static
discharges.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 1735-17-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1735-17-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1735-17-7 is not listed on the TSCA inventory.
It is for research and development use only.


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
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    全氘代环己烷 在 meso-tetrakis(pentafluorophenyl)porphirinato Fe(IV) nitrate 、 双氧水重氧水 作用下, 以 二氯甲烷乙腈 为溶剂, 反应 0.08h, 以20%的产率得到18O-cyclohexanol
    参考文献:
    名称:
    Remarkable Anionic Axial Ligand Effects of Iron(III) Porphyrin Complexes on the Catalytic Oxygenations of Hydrocarbons by H2O2 and the Formation of Oxoiron(IV) Porphyrin Intermediates bym-Chloroperoxybenzoic Acid
    摘要:
    DOI:
    10.1002/1521-3773(20001016)39:20<3646::aid-anie3646>3.0.co;2-q
  • 作为产物:
    描述:
    氘代苯 作用下, 生成 全氘代环己烷
    参考文献:
    名称:
    超高真空条件下钯表面的催化化学
    摘要:
    钯的独特催化能力(在超高真空下)已被证明用于多种化学反应。吡啶 (C/sub 5/H/sub 5/N) 由乙炔和氰化氢在 Pd(111) 上形成,产率约为 10%。乙炔和氰化氢在-110 /sup 0 / C共吸附,然后加热晶体。吡啶在 100/sup 0/C 下解吸,这是 Pd-NC/sub 5/H/sub 5/ 的特征解吸温度。在该表面上氢化吡啶的尝试没有成功。已在 Pd 上证明了以下加氢反应:乙炔生成乙烯 (50%)、乙烯生成乙烷 (25%)、苯生成环己烷 (5%) 和降冰片二烯生成降冰片烷 (5% 到 10%) 以及烯烃生成丙炔、2-丁炔和2-戊炔。典型的实验包括氢的吸附,然后在 -130/sup 0/C 下吸附烃,以及在 25/sup 0/C/s 下进行热解吸。氢化产物的出现发生在大约 0/sup 0/至 25/sup 0/C。乙腈氢化成乙胺也被证实。
    DOI:
    10.1021/ja00360a063
  • 作为试剂:
    描述:
    β-氯代丁酮 、 在 全氘代环己烷 作用下, 反应 0.25h, 以34%的产率得到
    参考文献:
    名称:
    酮和酯存在下Tp'Rh(CNneopentyl)(PhNCNneopentyl)的光解:活化不同脂肪族C–H键的动力学和热力学选择性† ‡
    摘要:
    由前体Tp'Rh(CNneopentyl)(PhN CNneopentyl)生成的活性片段[Tp'Rh(CNneopentyl)]经过氧化加成取代的酮和酯后生成Tp'Rh(CNneopentyl)(R)(H)络合物(Tp'=三-(3,5-二甲基吡唑基)硼酸酯)。这些C–H活化的复合物在C 6 D 6或C 6 D 12中的不同温度(24–70°C)下进行了还原消除。使用先前建立的动力学技术,计算了相对的Rh–C键强度。相对Rh–C结合强度与C–H结合强度的分析显示与斜率R M–C / C–H呈线性关系= 1.22(12)。通常,与被破坏的C–H键相比,α取代基会增加相对的Rh–C键强度。
    DOI:
    10.1039/c9dt01802f
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文献信息

  • Rapid and Direct Photocatalytic C(sp <sup>3</sup> )−H Acylation and Arylation in Flow
    作者:Daniele Mazzarella、Antonio Pulcinella、Loïc Bovy、Rémy Broersma、Timothy Noël
    DOI:10.1002/anie.202108987
    日期:2021.9.20
    photocatalytic procedure that enables the acylation/arylation of unfunctionalized alkyl derivatives in flow. The method exploits the ability of the decatungstate anion to act as a hydrogen atom abstractor and produce nucleophilic carbon-centered radicals that are intercepted by a nickel catalyst to ultimately forge C(sp3)−C(sp2) bonds. Owing to the intensified conditions in flow, the reaction time can be reduced
    在此,我们报告了一种光催化程序,该程序可以使未官能化的烷基衍生物在流动中酰化/芳基化。该方法利用十钨酸盐阴离子作为氢原子提取物并产生亲核碳中心自由基的能力,这些自由基被镍催化剂拦截以最终形成 C(sp 3 )-C(sp 2 ) 键。由于流动条件的强化,反应时间可以从 12-48 小时减少到仅 5-15 分钟。最后,动力学测量强调了强化条件如何不改变反应机制,而是可靠地加速整个过程。
  • Mechanism of Ni-Catalyzed Oxidations of Unactivated C(sp<sup>3</sup>)–H Bonds
    作者:Yehao Qiu、John F. Hartwig
    DOI:10.1021/jacs.0c09157
    日期:2020.11.11
    of ligands, the formation of carbon-centered radicals with long lifetimes, and the decomposition of mCPBA in the presence of Ni complexes suggest that the reaction occurs through free alkyl radicals. Selectivity on model substrates and deuterium-labeling experiments imply that the m-chlorobenzoyloxy radical derived from mCPBA cleaves C-H bonds in the alkane to form an alkyl radical, which subsequently
    在温和的条件下,间氯过苯甲酸 (mCPBA) 对未活化烷烃的镍催化氧化,包括聚乙烯的氧化,周转率很高,但这种转变的机制一直是一个争论的话题。已提出推定的高价镍-氧代或镍-氧基中间体来裂解 C-H 键,但对此类复合物的几项研究并未提供强有力的证据来支持对未活化的 C(sp3)-H 键的这种反应性。我们报道了 mCPBA 对 Ni 催化的未活化 C-H 键氧化的机理研究。缺乏配体的作用,形成具有长寿命的碳中心自由基,以及在 Ni 配合物存在下 mCPBA 的分解,表明该反应是通过游离烷基自由基发生的。对模型底物和氘标记实验的选择性意味着,源自 mCPBA 的间氯苯甲酰氧基自由基裂解烷烃中的 C-H 键以形成烷基自由基,随后与 mCPBA 反应以获得醇产物并再生芳氧基自由基。这种自由基链机制表明 Ni 不会像以前提出的那样裂解 C(sp3)-H 键;相反,它催化 mCPBA 分解形成芳基自由基。
  • High Catalytic Activity of Vanadium Complexes in Alkane Oxidations with Hydrogen Peroxide: An Effect of 8-Hydroxyquinoline Derivatives as Noninnocent Ligands
    作者:Izabela Gryca、Katarzyna Czerwińska、Barbara Machura、Anna Chrobok、Lidia S. Shul’pina、Maxim L. Kuznetsov、Dmytro S. Nesterov、Yuriy N. Kozlov、Armando J. L. Pombeiro、Ivetta A. Varyan、Georgiy B. Shul’pin
    DOI:10.1021/acs.inorgchem.7b02684
    日期:2018.2.19
    Five monomeric oxovanadium(V) complexes [VO(OMe)(N∩O)2] with the nitro or halogen substituted quinolin-8-olate ligands were synthesized and characterized using Fourier transform infrared, 1H and 13C NMR, high-resolution mass spectrometry–electrospray ionization as well as X-ray diffraction and UV–vis spectroscopy. These complexes exhibit high catalytic activity toward oxidation of inert alkanes to
    的五个单体氧钒(V)配合物[VO(OME)(N ∩ O)2 ]与硝基或卤素取代的喹啉-8-羟基钠盐配体合成,并使用傅立叶其特征变换红外,1 H和13 C NMR,高分辨率质谱–电喷雾电离以及X射线衍射和UV-可见光谱。这些络合物在乙腈水溶液中对H 2 O 2将惰性烷烃氧化为烷基氢过氧化物具有很高的催化活性,含氧化合物的收率高达39%,周转数1780。实验动力学研究中,C 6 D 12和18 O 2标记实验和密度泛函理论(DFT)计算允许提出反应机理,其中包括形成HO·自由基作为活性氧化物质。HO·形成的机理似乎不同于通常被芬顿或类芬顿体系接受的机制。H 2 O 2向均质的活化发生在过氧化氢与催化剂分子的金属中心简单配位时,不需要改变金属氧化态和形成HOO·自由基。这种活化与喹啉8-油酸酯配体的氧化还原活性性质有关。实验确定的用于活化[VO(OCH 3)(5-Cl-quin)配合物的环己烷的活化能2
  • Efficient Benzylic and Aliphatic C–H Oxidation with Selectivity for Methylenic Sites Catalyzed by a Bioinspired Manganese Complex
    作者:Duyi Shen、Chengxia Miao、Shoufeng Wang、Chungu Xia、Wei Sun
    DOI:10.1021/ol4037083
    日期:2014.2.21
    A benzimidazole-based nonheme manganese complex efficiently catalyzes benzylic, aliphatic C–H as well as tertiary C–H oxidation with hydrogen peroxide as the oxidant in the presence of acetic acid as additive. 18O labeling experiments suggest the reaction may proceed via a high-valent manganese-oxo intermediate.
    苯并咪唑基非血红素锰络合物在乙酸作为添加剂的情况下,以过氧化氢为氧化剂,可有效催化苄基,脂肪族CH–H以及叔CH–H氧化。18 O标记实验表明该反应可能通过高价锰-氧代中间体进行。
  • An Iron(III)-Monoamidate Complex Catalyst for Selective Hydroxylation of Alkane CH Bonds with Hydrogen Peroxide
    作者:Yutaka Hitomi、Kengo Arakawa、Takuzo Funabiki、Masahito Kodera
    DOI:10.1002/anie.201108933
    日期:2012.4.2
    Selective oxidation: The success of the title reaction (see scheme) is caused by the strong electron donation from the amidate moiety of the dpaq ligand to the iron center (dpaq=2‐[bis(pyridin‐2‐ylmethyl)]amino‐N‐quinolin‐8‐yl‐acetamidate). This process facilitates the OO bond heterolysis of the intermediate FeIIIOOH species to generate a selective oxidant without forming highly reactive hydroxyl
    选择性氧化:标题反应的成功(参见方案)是由dpaq配体的mid酰胺部分向铁中心的强电子给予(dpaq = 2- [双(吡啶-2-基甲基)]氨基-N引起的-喹啉-8-乙酰氨基乙酸)。此过程促进中间Fe III OOH物种的OO键杂化反应,生成选择性氧化剂,而不会形成高反应性羟基。
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表征谱图

  • 氢谱
    1HNMR
  • 质谱
    MS
  • 碳谱
    13CNMR
  • 红外
    IR
  • 拉曼
    Raman
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mass
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  • 峰位数据
  • 峰位匹配
  • 表征信息
Shift(ppm)
Intensity
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Assign
Shift(ppm)
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测试频率
样品用量
溶剂
溶剂用量
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