6-氯-1-己烯 | 928-89-2

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类卤化物
• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 中文名称: 6-氯-1-己烯
• 中文别名: 6-氯-1-乙烯
• 英文名称: 6-chlorohexene
• 英文别名: 6-chloro-1-hexene；6-chlorohex-1-ene；5-hexenyl chloride
• CAS: 928-89-2
• 化学式: C₆H₁₁Cl
• 分子量: 118.606
• InChiKey: BLMIXWDJHNJWDT-UHFFFAOYSA-N

物化性质

• 沸点：
  135-136 °C (lit.)
• 密度：
  0.896 g/mL at 25 °C (lit.)
• 闪点：
  84 °F
• 保留指数：
  869
• 稳定性/保质期：

  常温常压下稳定，避免与强氧化剂热接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  7
• 可旋转键数：
  4
• 环数：
  0.0
• 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

• TSCA：
  Yes
• 危险等级：
  3
• 危险品标志：
  Xi
• 危险类别码：
  R10,R36/37/38
• 危险品运输编号：
  UN 3295
• 海关编码：
  2903299090
• 安全说明：
  S16,S26,S37/39
• WGK Germany：
  3
• 储存条件：
  储存于干燥的惰性气体中，并保持容器密封。将其存放在阴凉、干燥处。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 6-Chloro-1-hexene
CAS-No. : 928-89-2
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]
Flammable liquids (Category 3)
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
Flammable. Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H226 Flammable liquid and vapour.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 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)
R10 Flammable.
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S16 Keep away from sources of ignition - No smoking.
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 : C6H11Cl
Molecular Weight : 118,6 g/mol
Component Concentration
6-Chlorohex-1-ene
CAS-No. 928-89-2 -
EC-No. 213-186-5

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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
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

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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, Hydrogen chloride gas
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
Use water spray to cool unopened containers.

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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. 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.
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.

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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

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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
Impervious clothing., 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).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: liquid
Colour: colourless
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 135 - 136 °C - lit.
boiling range
g) Flash point 28,9 °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 0,896 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

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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
Heat, flames and sparks.
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
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. Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: 3295 IMDG: 3295 IATA: 3295
UN proper shipping name
ADR/RID: HYDROCARBONS, LIQUID, N.O.S.
IMDG: HYDROCARBONS, LIQUID, N.O.S.
IATA: Hydrocarbons, liquid, n.o.s.
Transport hazard class(es)
ADR/RID: 3 IMDG: 3 IATA: 3
Packaging group
ADR/RID: III IMDG: III IATA: III
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：

  6-氯-1-己烯 在 O-新戊酰羟铵三氟甲磺酸盐 、 iron(II) diacetylacetonate 、 sodium chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 以71%的产率得到2,6-Dichlorohexan-1-amine
  参考文献：
  名称：

  通过烯烃的铁催化氨基氯化有效获得未受保护的伯胺

  摘要：

  盐和铁简化了生成胺的过程 在碳化合物中添加氮通常是一个费力的过程。氮通常需要保护以防止不希望的反应性，而且保护基团之后很难去除。莱尼亚尼等人。报告了一种将羟胺衍生物中未修饰的 NH2 直接添加到双键碳中心的通用方法。一种简单的铁催化剂通过自由基机制将食盐中的氯化物控制到相邻的碳上，从而为各种进一步的功能化选择做好准备。科学，这个问题 p。434 一种简单的铁催化剂与食盐中的氯化物一起作用，将相邻的氯和氮取代基添加到 C=C 双键上。伯胺是生物活性分子的基本成分，也是药物和农用化学品合成中的多功能中间体。然而，它们从容易获得的烯烃制备仍然具有挑战性。在这里，我们报告了通过操作简单的铁催化氨基氯化反应从烯烃中获取伯胺的一般策略。稳定的羟胺衍生物和良性氯化钠分别作为氮源和氯源。反应在室温空气中进行；耐受大范围的脂肪族和共轭烯烃，包括密集功能化的底物；并且对氨基提供优异的抗马尔科夫尼科夫区域选择性

  DOI：

  10.1126/science.aat3863
• 作为产物：
  描述：

  5-己烯酸 在 草酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 6-氯-1-己烯
  参考文献：
  名称：

  Mo-或W-基单芳基氧化物吡咯烷(MAP)配合物催化的闭环复分解(RCM)反应有效和选择性地形成大环双取代Z烯烃：在表拉烯、柚子内酯、Ambrettolide、埃坡霉素C和Nakadomarin全合成中的应用一种

  摘要：

  描述了通过催化闭环复分解 (RCM)高效Z选择性形成大环双取代烯烃的第一套广泛适用的方案。在 22 °C 下，使用 1.2–7.5 mol% 的 Mo 或 W 基单芳基氧化物吡咯烷 (MAP) 络合物进行环化，通常在两小时内完成转化。代表性的大环烯烃的合成证明了实用性，例如天然产物柚子内酯（13 元环：73 % Z）表漆烯（15 元环：91 % Z）、Ambrettolide（17 元环：91 % Z）、埃坡霉素 C 和 A（16 元环：高达 97 % Z）和 nakadomarin A（15 元环：高达97 % Z）的高级前体Z )。我们表明，催化Z选择性环化可以在克级有效地进行，复杂的分子起始材料和催化剂可以在空气中处理。我们阐明了催化协议的几个关键原则：1) Mo 催化剂的互补性质，提供高活性，但更容易产生 RCM 后立体异构化，而 W 变体提供较低的活性但不太倾向于导致失去动力学Z选择性。2)

  DOI：

  10.1002/chem.201204045
• 作为试剂：
  描述：

  氯丙烯镁 、 1,2-二溴乙烷 、 茚 在 6-氯-1-己烯 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 50.0h， 以25%的产率得到3-(4-penten-1-yl)-1H-indene
  参考文献：
  名称：

  [EN] HIGH ACTIVITY CATALYST COMPOSITIONS CONTAINING SILICON-BRIDGED METALLOCENES WITH BULKY SUBSTITUENTS
  [FR] COMPOSITIONS DE CATALYSEUR TRÈS ACTIVES CONTENANT DES MÉTALLOCÈNES À PONT SILICIUM POSSÉDANT DES SUBSTITUANTS VOLUMINEUX

  摘要：

  本发明揭示了采用具有庞大取代基的硅桥联茂金属化合物的催化剂组合物。还提供了制备这些硅桥联茂金属化合物以及在用于聚合烯烃的催化剂组合物中使用这些化合物的方法。

  公开号：

  WO2013019769A1

文献信息

• Chiral Pincer Carbodicarbene Ligands for Enantioselective Rhodium-Catalyzed Hydroarylation of Terminal and Internal 1,3-Dienes with Indoles
  作者：Justin S. Marcum、Courtney C. Roberts、Rajith S. Manan、Tia N. Cervarich、Simon J. Meek

  DOI：10.1021/jacs.7b08575

  日期：2017.11.8

  Catalytic enantioselective addition of N-heteroarenes to terminal and internal 1,3-dienes is reported. Reactions are promoted by 5 mol % of Rh catalyst supported by a new chiral pincer carbodicarbene ligand that delivers allylic substituted arenes in up to 95% yield and up to 98:2 er. Mechanistic and X-ray evidence is presented that supports that the reaction proceeds via a Rh(III)-η3-allyl.

  据报道N-杂芳烃向末端和内部1，3-二烯的催化对映选择性加成。5 mol％的Rh催化剂促进了反应，该催化剂由新型手性钳碳二碳烯配体支撑，该配体可提供高达95％的收率和高达98：2 er的烯丙基取代的芳烃。机械和透视证据呈现支持经由铑（III）-η反应进行3 -烯丙基。
• Iron-Catalyzed Highly Enantioselective Hydrosilylation of Unactivated Terminal Alkenes
  作者：Biao Cheng、Wenbo Liu、Zhan Lu

  DOI：10.1021/jacs.8b01638

  日期：2018.4.18

  The iron-catalyzed highly Markovnikov-type selective and enantioselective hydrosilylation of terminal aliphatic alkenes with good functional group tolerance is developed. This operationally simple protocol uses earth-abundant transition metal catalyst, readily available aliphatic alkenes and hydrosilanes to construct valuable chiral organosilanes with better than 99% ee in most cases. The chiral aliphatic

  开发了铁催化的具有良好官能团耐受性的末端脂肪族烯烃的高度马尔可夫尼科夫型选择性和对映选择性氢化硅烷化。这种操作简单的方案使用地球上丰富的过渡金属催化剂、容易获得的脂肪族烯烃和氢硅烷来构建有价值的手性有机硅烷，在大多数情况下，ee 优于 99%。手性脂肪族链烷-2-醇和手性二羟基硅烷作为酮的类似物可以通过手性有机硅烷的进一步衍生化而有效合成，无需任何外消旋化。
• Palladium-Catalyzed Aerobic Anti-Markovnikov Oxidation of Aliphatic Alkenes to Terminal Acetals
  作者：Saki Komori、Yoshiko Yamaguchi、Yasutaka Kataoka、Yasuyuki Ura

  DOI：10.1021/acs.joc.8b02919

  日期：2019.3.15

  Terminal acetals were selectively synthesized from various unbiased aliphatic terminal alkenes and 1,2-, 1,3-, or 1,4-diols using a PdCl2(MeCN)2/CuCl catalyst system in the presence of p-toluquinone under 1 atm of O2 and mild reaction conditions. The slow addition of terminal alkenes suppressed the isomerization to internal alkenes successfully. Electron-deficient cyclic alkenes, such as p-toluquinone

  在1 atm下在对甲苯醌存在下，使用PdCl 2（MeCN）2 / CuCl催化剂体系，由各种无偏的脂族末端烯烃和1,2-，1,3-或1,4-二醇选择性合成末端缩醛。O 2和温和的反应条件。末端烯烃的缓慢添加成功地抑制了异构化为内部烯烃。缺电子的环状烯烃，例如对甲苯醌，是增强催化活性和抗马尔科夫尼科夫选择性的关键添加剂。发现烯烃中的卤素基团起导向基团的作用，抑制了异构化并有效地提高了选择性。
• Formal hydration of non-activated terminal olefins using tandem catalysts
  作者：Yongsheng Yang、Jiayi Guo、Huimin Ng、Zhiyong Chen、Peili Teo

  DOI：10.1039/c3cc48810a

  日期：——

  The hydration of terminal olefins to secondary alcohols has been achieved using a Pd(II)/Ru(II) catalyst combination with high regioselectivity and yields. Both vinyl arenes and aliphatic olefins can be hydrated easily with the tandem catalyst system using a low catalyst loading of 1 mol%.

  使用Pd(II)/Ru(II)催化剂组合，成功实现了端烯向仲醇的高区域选择性和产率的水合反应。不论是乙烯基芳烃还是脂肪族烯烃，都能在低催化剂负载量（1 mol%）下，利用这种串联催化体系轻松进行水合反应。
• Generation and Reactivity of Amidyl Radicals: Manganese‐Mediated Atom‐Transfer Reaction
  作者：Run‐Zhou Liu、Jinxia Li、Jun Sun、Xian‐Guan Liu、Shuanglin Qu、Ping Li、Bo Zhang

  DOI：10.1002/anie.201913042

  日期：2020.3.9

  been developed. This approach employs an earth-abundant and inexpensive manganese complex, Mn2 (CO)10 , as the catalyst and visible light as the energy input. Using this strategy, site-selective chlorination of unactivated C(sp3 )-H bonds of aliphatic amines and intramolecular/intermolecular chloroaminations of unactivated alkenes were readily realized under mild reaction conditions, thus providing efficient

  已经开发了一种简单有效的方案，可通过锰介导的原子转移反应从胺官能团生成酰胺基。该方法采用了一种富含地球和廉价的锰络合物Mn2（CO）10作为催化剂，并使用了可见光作为能量输入。使用这种策略，脂肪族胺的未活化C（sp3）-H键和未活化烯烃的分子内/分子间氯胺的定点氯化很容易在温和的反应条件下实现，因此可以有效地获得一系列有价值的，氯化的烷基氯化物。吡咯烷和邻氯胺衍生物。这些实际反应显示出广泛的底物范围，并能耐受各种官能团以及包括各种市售药物衍生物在内的复杂分子。