反式-2-癸醛 | 3913-71-1

• 物质功能分类: 香精与香料 - 合成香料 - 醛类香料
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 反式-2-癸醛
• 中文别名: 2-癸烯醛
• 英文名称: 2-decenal
• 英文别名: decenal；dec-2-enal
• CAS: 3913-71-1
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: MMFCJPPRCYDLLZ-UHFFFAOYSA-N

物化性质

• 熔点：
  -16°C (estimate)
• 沸点：
  78-80 °C3 mm Hg(lit.)
• 密度：
  0.841 g/mL at 25 °C(lit.)
• 闪点：
  205 °F
• LogP：
  3.828 (est)
• 物理描述：
  Colourless to slightly yellow liquid; Powerful waxy, orange aroma
• 溶解度：
  Soluble in most fixed oils; Insoluble in water
• 折光率：
  1.452-1.458
• 保留指数：
  1235;1272;1239;1236.9;1242;1238;1238;1240;1242;1239.9

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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：
  Xi,N
• 安全说明：
  S26,S36/37,S60,S61
• 危险类别码：
  R50/53,R41,R43
• WGK Germany：
  3
• 危险品运输编号：
  UN 3082 9/PG 3

SDS

Name:	trans-2-Decenal Material Safety Data Sheet
Synonym:	beta-N-Heptylacrolein; 3-Heptylacrolein; trans-2-Decen-1-al; Decenaldehyd
CAS:	3913-71-1

Section 1 - Chemical Product MSDS Name:trans-2-Decenal Material Safety Data Sheet
Synonym:beta-N-Heptylacrolein; 3-Heptylacrolein; trans-2-Decen-1-al; Decenaldehyd

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3913-71-1	trans-2-Decenal	100	223-472-1

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 severe skin irritation.
Ingestion:
Causes gastrointestinal tract irritation.
Inhalation:
Causes respiratory tract irritation.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
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:
Treat symptomatically and supportively.

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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. Water may be ineffective. Material is lighter than water and a fire may be spread by the use of water. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
Extinguishing Media:
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. 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:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Do not get in eyes, on skin, or on clothing. Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation.
Storage:
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# 3913-71-1: 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 gloves to prevent skin exposure.
Clothing:
Wear appropriate clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: Slightly-Yellow Liquid
Odor: Orange-Like Odor
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 78.0 - 80.0 C @ 3mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: 96 deg C ( 204.80 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Insoluble in water.
Specific Gravity/Density: 0.8410
Molecular Formula: C10H18O
Molecular Weight: 154.1254

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 3913-71-1: HE2070000 LD50/LC50:
CAS# 3913-71-1: Draize test, rabbit, skin: 500 mg/24H Severe; Oral, rat: LD50 = 5 gm/kg; Skin, rabbit: LD50 = 3400 mg/kg.
Carcinogenicity:
trans-2-Decenal - 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 37 Wear suitable gloves.
WGK (Water Danger/Protection)
CAS# 3913-71-1: No information available.
Canada
CAS# 3913-71-1 is listed on Canada's DSL List.
CAS# 3913-71-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3913-71-1 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

含量分析

按气相色谱法GT-10-4中使用极性柱进行测定。

毒性

GRAS(FEMA)。LD₅₀为5000mg/kg（大鼠，经口）。

使用限量

根据FEMA标准：

• 软饮料：3.4 mg/kg
• 冷饮：6.0 mg/kg
• 糖果：9.0 mg/kg
• 焙烤食品：9.0 mg/kg

适度为限（FDA §172．515，2000）。

食品添加剂最大允许使用量及最大允许残留量标准

添加剂中文名称	允许使用该种添加剂的食品中文名称	添加剂功能	最大允许使用量（g/kg）	最大允许残留量（g/kg）
2-癸烯醛	食品	食品用香料	用于配制香精的各香料成分不得超过在GB 2760中的最大允许使用量和最大允许残留量

化学性质

微黄色液体，具有鸡、家禽和橙子似香味。溶于乙醇和大多数非挥发性油，不溶于水。沸点229℃（107～107.5℃/1533Pa），相对密度d₁₇.₅¹⁵ 0.846，折射率nD₁₇.₅ 1.4533。天然品存在于胡荽油中。

用途

GB 2760—96规定为允许使用的食用香料，主要用于配制家禽和柑橘类香精。

生产方法

由2-癸烯醇经重铬酸钾和浓硫酸氧化而得。

反应信息

• 作为反应物：
  描述：

  反式-2-癸醛 在 四氢吡咯 、 水 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以79%的产率得到正辛醛
  参考文献：
  名称：

  Secondary amine catalyzed retro-aldol reactions of enals and enones: one-pot conversion of enals to α-substituted derivatives

  摘要：

  A practical synthetic procedure to hydrolytically cleave the CC-double bond of alpha,beta-unsaturated aldehydes and ketones has been developed. Secondary amines are employed as organocatalysts for the retro-aldol process under simple and mild reaction conditions. Beside the generation of the parent aromatic aldehydes, the synthetic procedure has been successfully used in a one-pot reaction sequence to convert simple cinnamaldehydes into their alpha-aryl/alkyl substituted derivatives. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.039
• 作为产物：
  描述：

  癸醛 在 二(氰基苯)二氯化钯 、 亚硝酸特丁酯 、 氧气 、 对甲苯磺酸 、 均三甲苯 作用下， 以 叔丁醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 以70%的产率得到反式-2-癸醛
  参考文献：
  名称：

  t BuONO在室温下用氧脱氢合成线性α，β-不饱和醛

  摘要：

  通过有机亚硝酸盐和钯与分子氧作为唯一的清洁氧化剂的共催化，已经实现了通过室温氧化脱氢合成线性α，β-不饱和醛。线性α，β-不饱和醛可以在需氧催化条件下直接由相应的饱和线性醛有效地制备。除线性产品外，通过相同的标准方法也可以顺利实现芳香族类比。有机亚硝酸盐氧化还原助催化剂和醇溶剂在实现该方法中起着关键作用。

  DOI：

  10.1021/acscatal.7b01008

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%。
• Highly pH-Dependent Chemoselective Transfer Hydrogenation of α,β-Unsaturated Aldehydes in Water
  作者：Nianhua Luo、Jianhua Liao、Lu Ouyang、Huiling Wen、Jitian Liu、Weiping Tang、Renshi Luo

  DOI：10.1021/acs.organomet.9b00353

  日期：2019.8.12

  electron-poor substituents on the aryl group of α,β-unsaturated aldehydes can be tolerated, affording the corresponding products in excellent yields with high TOF values. High selectivity and yields were also observed for α,β-unsaturated aldehydes with aliphatic substituents. Our mechanistic investigations indicate that the pH value is critical to the chemoselectivity.

  在水中实现了pH依赖的选择性Ir催化的α，β-不饱和醛的加氢反应。在低pH下使用HCOOH作为氢化物供体，仅获得不饱和醇产物，而在高pH下，优先使用HCOONa作为氢化物供体形成饱和醇产物。可以耐受包括α，β-不饱和醛的芳基上的富电子以及贫电子取代基在内的各种官能团，从而以高收率提供具有高收率的相应产物。还观察到具有脂族取代基的α，β-不饱和醛的高选择性和产率。我们的机理研究表明，pH值对化学选择性至关重要。
• Reactions of α-haloacroleins with azides: highly regioselective synthesis of formyl triazoles
  作者：Dongsheng Zhang、Yingzhu Fan、Zhongliang Yan、Yi Nie、Xingquan Xiong、Lizhu Gao

  DOI：10.1039/c9gc01129c

  日期：——

  A general metal-free route to 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles was developed. α-Haloacroleins reacted with organic azides in a DMSO/H2O mixture solvent at room temperature to produce 1,4-disubstituted triazoles (up to 99%) with exclusive regioselectivities. This protocol is convenient and scalable with a broad substrate scope including aliphatic and aromatic azides. The resulting

  开发了一种通向1,4-二取代和1,4,5-三取代的1,2,3-三唑的无金属路线。在室温下，α-卤代丙烯醛与有机叠氮化物在DMSO / H 2 O混合溶剂中反应，生成具有区域选择性的1,4-二取代三唑（最高99％）。该协议方便且可扩展，具有广泛的底物范围，包括脂肪族和芳香族叠氮化物。所得三唑在C4位上显示醛基，并证明了其合成用途。还鉴定了一种含有非对映体质子的1,2,3-三唑化合物。
• Synthesis of Monofluoromethylthioesters from Aldehydes
  作者：Shi-Huan Guo、Meng-Yue Wang、Gao-Fei Pan、Xue-Qing Zhu、Ya-Ru Gao、Yong-Qiang Wang

  DOI：10.1002/adsc.201800136

  日期：2018.5.2

  A direct and efficient approach to the synthesis of monofluoromethylthioesters from aldehydes has been developed. The synthetic method features mild reaction conditions, good tolerance of functional groups, a broad substrate scope, and especially no metal involved in the reaction. The approach has the potential to be an important tool for the late‐stage functionalization of advanced synthetic intermediates

  已经开发了直接和有效的由醛合成单氟甲基硫代酯的方法。该合成方法具有温和的反应条件，对官能团的良好耐受性，广泛的底物范围，特别是没有金属参与反应。该方法有可能成为高级合成中间体后期功能化的重要工具，并可能在药物化学中找到许多应用。
• Auto-Tandem Catalysis with Frustrated Lewis Pairs for Reductive Etherification of Aldehydes and Ketones
  作者：Mária Bakos、Ádám Gyömöre、Attila Domján、Tibor Soós

  DOI：10.1002/anie.201700231

  日期：2017.5.2

  Herein we report that a single frustrated Lewis pair (FLP) catalyst can promote the reductive etherification of aldehydes and ketones. The reaction does not require an exogenous acid catalyst, but the combined action of FLP on H2, R‐OH or H2O generates the required Brønsted acid in a reversible, “turn on” manner. The method is not only a complementary metal‐free reductive etherification, but also a niche

  在本文中，我们报道了单个沮丧的路易斯对（FLP）催化剂可以促进醛和酮的还原醚化。该反应不需要外源酸催化剂，但是FLP对H 2，R-OH或H 2 O的联合作用以可逆的“开启”方式产生所需的布朗斯台德酸。该方法不仅是一种补充性的无金属还原醚化方法，而且还是醚类的利基方法，这种方法在合成上不方便，甚至很难通过其他合成方案进行操作。