顺式-3-己烯醛 | 6789-80-6

• 物质功能分类: 有机原料 - 醛类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 顺式-3-己烯醛
• 中文别名: (Z)-3-己烯醛；顺-3-己烯醛
• 英文名称: (3Z)-hexenal
• 英文别名: (Z)-3-hexenal；cis-3-hexenal；(Z)-hex-3-enal；(3Z)-hex-3-enal；(Z)-3-hexen-1-al
• CAS: 6789-80-6
• 化学式: C₆H₁₀O
• 分子量: 98.1448
• InChiKey: GXANMBISFKBPEX-ARJAWSKDSA-N

物化性质

• 熔点：
  -78°C (estimate)
• 沸点：
  20 °C0.2 mm Hg
• 密度：
  0.982 g/mL at 25 °C
• 闪点：
  140 °F
• 溶解度：
  可溶于氯仿、甲醇
• LogP：
  1.73
• 物理描述：
  colourless liquid
• 折光率：
  1.427-1.436
• 保留指数：
  778;775;764;834;829;773;770;770;766;769;765;769;834;779;764;769
• 稳定性/保质期：
  存在于烟叶中。

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 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：
  R22
• 危险品运输编号：
  UN 1207 3
• WGK Germany：
  1
• 储存条件：
  -20°C

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : cis-3-Hexenal solution
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
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
Flammable liquids (Category 3), H226
Eye irritation (Category 2), H319
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xn Harmful R22
Xi Irritant R36
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H226 Flammable liquid and vapour.
H319 Causes serious eye irritation.
Precautionary statement(s)
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) Xn Harmful
R-phrase(s)
R22 Harmful if swallowed.
R36 Irritating to eyes.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
Other hazards - none

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SECTION 3: Composition/information on ingredients
Mixtures
Formula : C6H10O
Molecular Weight : 98,14 g/mol
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
(Z)-Hex-3-enal
CAS-No. 6789-80-6 Acute Tox. 4; Eye Irrit. 2; 50 - 100 %
EC-No. 229-854-4 H302, H319
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
(Z)-Hex-3-enal
CAS-No. 6789-80-6 Xn, R22 - R36 50 - 100 %
EC-No. 229-854-4
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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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
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
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
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 vapours, 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.
For personal protection see section 8.
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.

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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.
For precautions see section 2.2.
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.
Recommended storage temperature: -20 °C
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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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, 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).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into
the environment must be avoided.

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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 20 °C at 0,3 hPa
boiling range
g) Flash point 60 °C - closed cup
h) Evapouration 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 0,976 g/cm3
n) Water solubility slightly soluble
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
Stable under recommended storage conditions.
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
In the event of fire: see section 5

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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 sensitisation
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
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
Toxic to aquatic life.

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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.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: 1207 IMDG: 1207 IATA: 1207
UN proper shipping name
ADR/RID: HEXALDEHYDE, SOLUTION
IMDG: HEXALDEHYDE, SOLUTION
IATA: Hexaldehyde, SOLUTION, SOLUTION
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
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
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Acute Tox. Acute toxicity
Eye Irrit. Eye irritation
H226 Flammable liquid and vapour.
H302 Harmful if swallowed.
H319 Causes serious eye irritation.
Full text of R-phrases referred to under sections 2 and 3
Xn Harmful
R22 Harmful if swallowed.
R36 Irritating to eyes.
Further information
Copyright 2014 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：

  顺式-3-己烯醛 在 Lindlar's catalyst 吡啶 、 咪唑 、 titanium(IV) isopropylate 、 甲醇 、 叔丁基过氧化氢 、 sodium chlorite 、 sodium dihydrogenphosphate 、 正丁基锂 、 calcium hydride 、 2-甲基-2-丁烯 、 L-(+)-酒石酸二异丙酯 、 3 A molecular sieve 、 四丁基氟化铵 、 氢气 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 生成 (11S,12S,13S)-(9Z,15Z)-11-Hydroxy-12,13-epoxyoctadeca-9,15-dienoic acid methyl ester
  参考文献：
  名称：

  Enantiocontrolled Synthesis of (11S,12S,13S)-(9Z,15Z)- and (11R,12S,13S)-(9Z,15Z)-11-Hydroxy-12,13-epoxy Octadecadienoic Acids by Means of the Sharpless Asymmetric Epoxidation of the Unsymmetrical Divinylcarbinol

  摘要：

  (11S,12S,13S)-(9Z,15Z)-和(11R,12S,13S)-(9Z,15Z)-11-羟基-12,13-环氧十八碳二烯酸是一种防御稻瘟病的自卫物质，通过利用Sharpless不对称环氧化反应处理不对称二烯丙基醇作为关键步骤，实现了具有对映选择性地合成。

  DOI：

  10.3987/com-97-s48
• 作为产物：
  描述：

  1-Methoxy-hexen-(1)-in-(3). 在 Lindlar's catalyst 氢气 、 sodium methylate 、 草酸 、 邻苯二酚 作用下， 以 正己烷 、 水 、 丙酮 为溶剂， 反应 24.0h， 生成 顺式-3-己烯醛
  参考文献：
  名称：

  气味和成分二十一。顺式β-乙烯醛的合成。II

  摘要：

  AbstractThe authors describe a new general synthesis of cis‐β‐ethylene aldehydes: the alkylation of 1‐methoxy‐1‐buten‐3‐yne to 1‐methoxy‐1‐alken‐3‐ynes followed by addition of methanol produces 1,1‐dimethoxy‐3‐alkynes. The catalytical reduction of these compounds to 1,1‐dimethoxy‐3‐alkenes followed by mild acidic hydrolysis yields cis‐β‐ethylene aldehydes.

  DOI：

  10.1002/hlca.19630460541

文献信息

• Absolute configuration of octanol derivatives in apple fruits
  作者：Till Beuerle、Peter Schreier、Pascal Brunerie、Carlo Bicchi、Wilfried Schwab

  DOI：10.1016/0031-9422(96)00215-4

  日期：1996.9

  synthesized optically-enriched reference compounds with isolated diols and hydroxyesters, revealed the (R)-configuration for the free diols in cvs. Renao, Bedan, Peau de Chien and Noel des Champs and the (R)-configuration for the bound diols in cvs Bedan, Peau de Chien and Noel des Champs, exhibiting enantiomeric excesses (ees) greater than 99%. (R)-hydroxyesters (ee > 99%) were detected in cvs. Noel des Champs

  在五个苹果品种（Renao；Bedan；Peau de Chien；Noel des Champs；Red Delicious）通过液-液萃取和酶水解获得的提取物中，游离和糖苷键合的辛烷-1,3-二醇和 5( Z)-octene-1,3-diol，以及 3-羟基辛酸乙酯和 5(Z)-3-羟基辛酸乙酯，通过多维气相色谱 (MDGC) 进行分析，将极性非手性柱 (DB-Wax) 与手性主柱（2,3-二-O-乙酰基-6-O-叔丁基二甲基甲硅烷基-β-环糊精/OV 1701）。比较合成的光学富集参考化合物与分离的二醇和羟基酯的保留时间，揭示了 cvs 中游离二醇的 (R)-构型。Renao、Bedan、Peau de Chien 和 Noel des Champs 以及 cvs Bedan、Peau de Chien 和 Noel des Champs 中结合二醇的 (R)-构型，表现出大于 99%
• 含希夫碱结构的阻燃相变材料及其制备方法和应用
  申请人：四川大学

  公开号：CN112592291B

  公开（公告）日：2022-11-25

  本发明公开的含希夫碱结构的阻燃相变材料的结构通式为：且其的相变温度为33～101℃，相变焓高达117.9‑183.4J/g，残碳率为3.4～23.8％；结构通式[Ⅰ]、[Ⅱ]表示的阻燃相变材料初始分解温度可分别提高19.3～42.7％和34.9～38.8％。本发明还公开了其制备方法和应用。因本发明相变材料中含有具有高温交联成炭的作用的C＝N基团，不仅生成的炭层隔热隔氧效果好，还可改变材料的热失重行为，并具有较高的相变储能性，在未外加阻燃剂，就能赋予其优良的阻燃性，并避免外加阻燃剂所带来的储能密度的减小以及相容性问题；所制备的阻燃相变材料在加工及反应过程中不会发生交联，因而保留了其良好的加工性；且制备方法简单，成本较低，有利于规模化推广。
• Pheromone synthesis. Part 257: Synthesis of methyl (2E,4Z,7Z)-2,4,7-decatrienoate and methyl (E)-2,4,5-tetradecatrienoate, the pheromone components of the male dried bean beetle, Acanthoscelides obtectus (Say)
  作者：Kenji Mori

  DOI：10.1016/j.tet.2015.06.051

  日期：2015.8

  oxidation/Wittig reaction of (2Z,5Z)-2,5-octadien-1-ol yielded methyl (2E,4Z,7Z)-2,4,7-decatrienoate, a newly discovered pheromone component of the male dried bean beetle, while that of (±)-2,3-dodecadien-1-ol gave (±)-methyl (E)-2,4,5-tetradecatrienoate, the racemate of the known and major pheromone component. Methyl (2E,4E,7Z)-2,4,7-decatrienoate was also synthesized, which is the methyl ester of an acid metabolite

  （2 Z，5 Z）-2,5-辛二烯-1-醇的串联Dess-Martin氧化/维蒂希反应产生了新发现的（2 E，4 Z，7 Z）-2,4,7-癸三烯酸甲酯雄性干豆甲虫的信息素成分，而（±）-2,3-dodecadien-1-ol的信息素成分产生（±）-甲基（E）-2,4,5-十四碳三烯酸酯，是已知和主要的外消旋体信息素成分。还合成了（2 E，4 E，7 Z）-2,4,7-十碳三烯酸甲酯，它是绿藻酸代谢产物的甲酯。用Zn-Cu / EtOH还原2,5-辛二炔-1-醇可干净地得到（2 Z，5 Z）-2,5-辛二烯-1-醇。
• Characterization of Aroma-Active Compounds in Italian Tomatoes with Emphasis on New Odorants
  作者：Johanna Kreissl、Peter Schieberle

  DOI：10.1021/acs.jafc.7b01108

  日期：2017.6.28

  5-dimethyl-3(2H)-furanone. Of the further odorants, 13 compounds have previously not been reported as tomato odorants. Although most of these showed lower FD-factors, in particular, the coconut/dill-like smelling wine lactone ((3S,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one) appeared with a quite high FD factor. In addition, a fruity, almond-like odorant (6) with an FD factor of 1024 was

  通过溶剂萃取和随后的SAFE蒸馏，从意大利葡萄番茄中制得香气馏出物，产生强烈的总体香气。gc /嗅觉测定法和香气提取物稀释分析的应用揭示了44种气味活性化合物，其中42种可以被识别。对绿色，草绿色（Z）-3-己烯醛，金属味反式-4,5-环氧-（E）-2-癸烯，马铃薯样3-（甲硫基）确立了最高的气味活性值2048丙醛和焦糖状的4-羟基-2,5-二甲基-3（2 H）-呋喃酮。在其他增香剂中，以前没有13种化合物被报道为番茄增香剂。尽管其中大多数显示出较低的FD因子，尤其是椰子/莳萝味的葡萄酒内酯（（3S，3a S，7a R）-3a，4,5,7a-四氢-3,6-二甲基苯并呋喃-2（3 H）-one）的FD系数很高。此外，还检测到FD系数为1024的果味杏仁状增香剂（6）。通过应用高分辨率质谱法和极性考虑因素，提出了甲基-2-乙氧基四氢吡喃异构体的结构用于6。合成了五个可能的异构体中的四个，即3-
• The atmospheric photolysis of E-2-hexenal, Z-3-hexenal and E,E-2,4-hexadienal
  作者：Margaret P. O’Connor、John C. Wenger、Abdelwahid Mellouki、Klaus Wirtz、Amalia Muñoz

  DOI：10.1039/b611344c

  日期：——

  at the large outdoor European Photoreactor (EUPHORE) in Valencia, Spain. E-2-Hexenal and E,E-2,4-hexadienal were found to undergo rapid isomerization to produce Z-2-hexenal and a ketene-type compound (probably E-hexa-1,3-dien-1-one), respectively. Both isomerization processes were reversible with formation of the reactant slightly favoured. Values of j(E-2-hexenal)/j(NO(2)) = (1.80 +/- 0.18) x 10(-2)

  在西班牙瓦伦西亚的大型室外欧洲光反应器（EUPHORE）上研究了E-2-己烯，Z-3-己烯和E，E-2,4-己二烯的大气光解作用。发现E-2-己烯醛和E，E-2,4-己二烯经过快速异构化生成Z-2-己烯酮和烯酮型化合物（可能是E-hexa-1,3-dien-1-one） ， 分别。两种异构化过程都是可逆的，反应物的形成略有偏爱。j（E-2-hexenal）/ j（NO（2））=（1.80 +/- 0.18）x 10（-2）和j（E，E-2,4-hexadienal）/ j（NO（ 2））=（2.60 +/- 0.26）x 10（-2）被确定。测量了E-2-己烯和E，E-2,4-己二烯的气相紫外吸收截面，并得出E-2-己烯和0.32 +的光异构化的有效量子产率为0.36 +/- 0.04。对于E，E-2，4-己二醛为-/ 0.03。尽管光解似乎是E-2-己烯和E，E-2,4-己二烯的重要大气

表征谱图