反式-2-壬烯醛 | 18829-56-6

• 物质功能分类: 化学试剂 - 有机试剂 - 脂肪醛（含缩醛，半缩醛）
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 反式-2-壬烯醛
• 中文别名: 反-2-壬烯醛；反式-2-壬醛
• 英文名称: (2E)-nonenal
• 英文别名: (E)-2-Nonenal；trans-2-nonenal；(2E)-non-2-enal；(E)-non-2-enal；(2E)-nonen-1-al；2-Nonenal
• CAS: 18829-56-6
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: BSAIUMLZVGUGKX-BQYQJAHWSA-N

物化性质

• 熔点：
  -28°C (estimate)
• 沸点：
  88-90 °C12 mm Hg(lit.)
• 密度：
  0.846 g/mL at 25 °C(lit.)
• 蒸气密度：
  >1 (vs air)
• 闪点：
  184 °F
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• LogP：
  3.17
• 物理描述：
  White to slightly yellow liquid; Powerful, penetrating fatty, violet aroma
• 折光率：
  1.454-1.460
• 保留指数：
  1133.3;1133.3;1137;1139;1139;1130;1132;1137;1135;1132.7;1134;1134;1130;1136;1136;1145;1149;1136;1134;1142;1136;1133;1134;1142;1142;1133;1135;1130;1130;1114;1140;1124;1133;1133;1147;1131;1129;1138;1135;1147;1147;1128;1128;1123;1146;1135.3;1132;1123;1142;1146;1180;1150;1130;1126;1130;1130;1133;1136;1133;1133;1135;1133;1138;1142;1140;1141;1146;1132;1135
• 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)：
  3.1
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• TSCA：
  Yes
• 危险等级：
  3
• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  2,3
• 海关编码：
  2912190090
• 危险品运输编号：
  NA 1993 / PGIII
• RTECS号：
  RA8509050
• 包装等级：
  II
• 危险类别：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  常温下应密闭避光保存，并保持通风和干燥。

SDS

Name:	Trans-2-Nonenal 95% Material Safety Data Sheet
Synonym:	None
CAS:	18829-56-6

Section 1 - Chemical Product MSDS Name:Trans-2-Nonenal 95% Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
18829-56-6	Trans-2-Nonenal	95	242-609-6

Hazard Symbols: XI
Risk Phrases: 38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to skin.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. The toxicological properties of this material have not been fully investigated.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or 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.
Notes to Physician:

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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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Use water spray to keep fire-exposed containers cool. Combustible liquid.
Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Containers may explode when heated.
Extinguishing Media:
Use water spray to cool fire-exposed containers. Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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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. Remove all sources of ignition. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and 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. 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, sparks, 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. Keep refrigerated. (Store below 4C/39F.)

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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.
Exposure Limits CAS# 18829-56-6: 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 appropriate protective gloves to prevent skin exposure.
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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear, colorless
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 55 - 60 deg C @ .30mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: 79 deg C ( 174.20 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: insoluble
Specific Gravity/Density: .8400g/cm3
Molecular Formula: C9H16O
Molecular Weight: 140.23

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, ignition sources, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 18829-56-6: RA8509050 LD50/LC50:
Not available.
Carcinogenicity:
Trans-2-Nonenal - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION

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

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 38 Irritating to skin.
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
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# 18829-56-6: No information available.
Canada
CAS# 18829-56-6 is listed on Canada's DSL List.
CAS# 18829-56-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 18829-56-6 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

应用领域

反式-2-壬烯醛是一种2-烯醛衍生物，又称α,β-不饱和醛衍生物，是一类具有生物化学活性的化合物。它不仅是重要的工业产品及生产原料，在合成化学中扮演着重要角色，如与共轭二烯发生Diels-Alder反应可生成一系列脂环族烯烃化合物；在碱性催化剂的作用下，还能进行亲核加成的Michael反应，生成多种有用的化合物。

此外，多种2-烯醛，包括(E)-2-戊烯醛、(E)-2-己烯醛、(E)-2-庚烯醛、(E)-2-辛烯醛、(E)-2-壬烯醛、(E)-2-癸烯醛、(E)-2-十一烯醛和(E)-2-十二烯醛、(E)-2-十三烯醛，常被用作食用香料。

在药学领域，2-烯醛衍生物也有广泛应用。例如，(E)-2-己烯醛对革兰氏阳性菌和革兰氏阴性菌具有显著抑制作用；而(E)-2-己烯醛、(E)-2-庚烯醛、(E)-2-辛烯醛和(E)-2-壬烯醛能有效抑制黄曲霉菌（Aspergillus flavus）的菌丝生长。此外，(E)-2-己烯醛还能显著抑制玉米储存过程中产生的串珠镰刀菌（Fusarium verticillioides）。

制备 1. α-苯硫基壬醛的合成

取正壬炔（0.12克，1 mmol）、苯硫酚(2a)（0.33克，3 mmol），溶于氯仿中，在20℃下反应。通过TLC跟踪至完全结束，得到粗产物后经过柱层析分离（石油醚∶乙酸乙酯=10∶1），最终得到目标产物（产率84%）。

2. 目标产物 (E)-2-壬烯醛的合成

称取α-苯硫基壬醛(3f)（0.25克，1 mmol），溶于10 mL二氯甲烷中，在0℃下逐滴加入过氧化氢水溶液（0.22 克，2 mmol, 30%）。继续搅拌3小时后，再加10毫升水并保持在30℃下搅拌反应。通过TLC跟踪直至完全结束。反应结束后，将产物倒入碳酸氢钠的饱和溶液中，分离水相，并用二氯甲烷萃取，合并有机层后依次加入碳酸氢钠的饱和溶液洗涤、无水硫酸镁干燥和浓缩。粗产品经过柱层析分离（石油醚∶乙酸乙酯=10∶1），最终得到目标产物 (E)-2-壬烯醛（产率83%）。

反应信息

• 作为反应物：
  描述：

  反式-2-壬烯醛 在 氢氧化钾 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 2E,8Z-Undecadienoic acid
  参考文献：
  名称：

  Reaction Principles and Crystal Structure Design for the Topochemical Polymerization of 1,3-Dienes

  摘要：

  DOI：

  10.1002/1521-3773(20020715)41:14<2502::aid-anie2502>3.0.co;2-9
• 作为产物：
  描述：

  (Z)-N-(n-heptylidene)methylamine N-oxide 在 氢氟酸 作用下， 以 乙腈 、 苯 为溶剂， 反应 0.5h， 生成 反式-2-壬烯醛
  参考文献：
  名称：

  Nitrone cycloadditions. An efficient method for the homologation of aldehydes to .alpha.,.beta.-unsaturated aldehydes

  摘要：

  DOI：

  10.1021/jo00192a047

文献信息

• New Phosphonate Reagents for Aldehyde Homologation
  作者：Richard J. Petroski

  DOI：10.1080/00397910701569114

  日期：2007.10.1

  Abstract New phosphonate reagents were developed for the two‐carbon homologation of aldehydes to unbranched or methyl‐branched unsaturated aldehydes. The phosphonate reagents, diethyl methylformylphosphonate dimethylhydrazone and diethyl ethylformyl‐2‐phosphonate dimethylhydrazone, contained a protected aldehyde group instead of the usual ester group. A homologation cycle entailed condensation of the

  摘要 开发了新的膦酸酯试剂，用于醛与直链或甲基支链不饱和醛的双碳同系化。膦酸酯试剂，二乙基甲基甲酰基膦酸酯二甲基腙和二乙基乙基甲酰基-2-膦酸酯二甲基腙，含有受保护的醛基而不是通常的酯基。同系化循环需要将试剂与起始醛缩合，然后用 1 M HCl 和石油醚的双相混合物去除二甲基腙保护基团。这种稳健的两步法适用于脂肪族醛、α,β-不饱和醛和芳香醛。缩合步骤的分离产率范围为 77% 至 89%，脱保护步骤的产率范围为 81% 至 96%。
• [EN] ENCAPSULATES<br/>[FR] PRODUITS ENCAPSULÉS
  申请人：PROCTER & GAMBLE

  公开号：WO2013022949A1

  公开（公告）日：2013-02-14

  The present application relates to encapsulates, compositions, products comprising such encapsulates, and processes for making and using such encapsulates. Such encapsulates comprise a core comprising a perfume and a shell that encapsulates said core, such encapsulates may optionally comprise a parametric balancing agent, such shell comprising one or more azobenzene moieties.

  本申请涉及封装体、组合物、包含这种封装体的产品，以及制备和使用这种封装体的方法。这种封装体包括一个包含香水的核心和封装该核心的壳，这种封装体可以选择性地包含一个参数平衡剂，该壳包括一个或多个偶氮苯基团。
• Lithium triethylborohydride as catalyst for solvent-free hydroboration of aldehydes and ketones
  作者：Krzysztof Kuciński、Grzegorz Hreczycho

  DOI：10.1039/c9gc00216b

  日期：——

  Commercially available and inexpensive lithium triethylborohydride (LiHBEt3) acts as efficient catalyst for the solvent-free hydroboration of a wide range of aldehydes and ketones, which were subsequently transformed to corresponding 1° and 2° alcohols in one-pot procedure at room temperature (rt).

  市售和廉价的三乙基硼氢化锂（LiHBEt 3）可以用作多种醛和酮的无溶剂氢硼化的有效催化剂，随后在室温下通过一锅法将其转化为相应的1°和2°醇（ rt）。
• Bridging the Final Gap in Stereocontrolled Wittig Reactions: Methoxymethoxy-Armed Allylic Phosphorus Ylides Affording Conjugated Dienes with Highcis Selectivity
  作者：Qian Wang、Mirella El Khoury、Manfred Schlosser

  DOI：10.1002/(sici)1521-3765(20000204)6:3<420::aid-chem420>3.0.co;2-h

  日期：2000.2.4

  sodium amide), 2-alkenyltris(2-methoxymethoxyphenyl)phosphonium salts carrying an allyl, crotyl, or prenyl (3-methyl-2-butenyl) side chain condense with saturated or unsaturated aldehydes to give conjugated dienes with Z/E ratios ranging from 90:10 to > 99:1 and averaging 96:4. Owing to steric congestion, yields are only moderate (on average 41%; extremes 10-79%). The nonvolatile tris(2-methoxymethoxyphenyl)phosphine

  用适当的碱（丁基锂或氨基钠）处理后，带有烯丙基，巴豆基或异戊烯基（3-甲基-2-丁烯基）侧链的2-烯基三（2-甲氧基甲氧基苯基）phosph盐与饱和或不饱和醛缩合，生成Z / E比为90:10至> 99：1，平均为96：4的共轭二烯。由于空间拥堵，单产仅为中等水平（平均41％；极端水平为10-79％）。非挥发性三（2-甲氧基甲氧基苯基）氧化膦副产物可以容易地分离和还原以回收膦原料，或者可以将其水解为水溶性三（2-羟苯基）氧化膦。
• A new synthesis of α,β-unsaturated aldehydes
  作者：Jean-Marc Nuzillard、Ahcene Boumendjel、Georges Massiot

  DOI：10.1016/s0040-4039(01)80653-5

  日期：1989.1

  The two carbon homologation of carbonyl compounds to α,β-unsaturated aldehydes is achieved by the Wittig-Horner reaction with N-methoxy N-methyl diethylphosphonoacetamide followed by lithium aluminum hydride reduction.

  羰基化合物与α，β-不饱和醛的两个碳同系物是通过Wittig-Horner反应与N-甲氧基N-甲基二乙基膦酰基乙酰胺，然后氢化铝锂还原而实现的。

表征谱图