(R)-(+)-N-烯丙基-α-甲基苄胺 | 126275-19-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (R)-(+)-N-烯丙基-α-甲基苄胺
• 中文别名: (R)-(+)-N-烯丙基-Alpha-甲基苄胺
• 英文名称: (R)-N-allyl (1-phenylethyl)amine
• 英文别名: (R)-N-allyl-N-α-methylbenzylamine；(R)-(+)-N-allyl-α-methyl-benzylamine；(R)-N-allyl-N-(1-phenylethyl)amine；(R)-(+)-N-allyl-alpha-methylbenzylamine；N-[(1R)-1-phenylethyl]prop-2-en-1-amine
• CAS: 126275-19-2
• 化学式: C₁₁H₁₅N
• 分子量: 161.247
• InChiKey: GGNXWCWCESEPFK-SNVBAGLBSA-N

物化性质

• 沸点：
  58-59 °C/1 mmHg (lit.)
• 密度：
  0.919 g/mL at 25 °C (lit.)
• 闪点：
  187 °F

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 安全说明：
  S23,S26,S36,S37,S39,S45
• 危险类别码：
  R34
• 海关编码：
  2921499090
• WGK Germany：
  3
• 危险品运输编号：
  UN 2735 8/PG 2

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
: (R)-(+)-N-allyl-α-methylbenzylamine
Product name

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
According to Regulation (EC) No1272/2008
Skin corrosion (Category 1B)
According to European Directive 67/548/EEC as amended.
Causes burns.
Label elements
Pictogram
Signal word Danger
Hazard statement(s)
H314 Causes severe skin burns and eye damage.
Precautionary statement(s)
P280 Wear protective gloves/ protective clothing/ eye protection/ face protection.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
P310 Immediately call a POISON CENTER or doctor/ physician.
Hazard symbol(s)
C Corrosive
R-phrase(s)
R34 Causes burns.
S-phrase(s)
S23 Do not breathe vapour.
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36/37/39 Wear suitable protective clothing, gloves and eye/face protection.
S45 In case of accident or if you feel unwell, seek medical advice immediately
(show the label where possible).
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Formula : C11H15N
Molecular Weight : 161,24 g/mol
CAS-No. EC-No. Index-No. Classification Concentration
(R)-(+)-N-allyl-α-methylbenzylamine
126275-19-2 - - Skin Corr. 1B; Eye Dam. 1; -
H314
C, R34
For the full text of the H-Statements mentioned in this Section, see Section 16.

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Section 4. 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
Take off contaminated clothing and shoes immediately. 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.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special protective equipment for fire-fighters
Wear self contained breathing apparatus for fire fighting if necessary.

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions
Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation.
Evacuate personnel to safe areas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed
containers for disposal.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid inhalation of vapour or mist.
Normal measures for preventive fire protection.
Conditions for safe storage
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. Store in cool place.

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Personal protective equipment
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).
Hand 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.
Eye protection
Tightly fitting safety goggles. Faceshield (8-inch minimum). Use equipment for eye protection tested and
approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin and body protection
Complete suit protecting against chemicals, The type of protective equipment must be selected according
to the concentration and amount of the dangerous substance at the specific workplace.
Hygiene measures
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at
the end of workday.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Appearance
Form liquid
Colour colourless
Safety data
pH no data available
Melting point no data available
Boiling point 58 - 59 °C at 1 hPa - lit.
Flash point no data available
Ignition temperature no data available
Lower explosion limit no data available
Upper explosion limit no data available
Density 0,919 g/cm3 at 25 °C
Water solubility no data available

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Section 10. STABILITY AND REACTIVITY
Chemical stability
Stable under recommended storage conditions.
Conditions to avoid
no data available
Materials to avoid
Strong oxidizing agents
Hazardous decomposition products
Hazardous decomposition products formed under fire conditions. - Carbon oxides, nitrogen oxides (NOx)

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Section 11. TOXICOLOGICAL INFORMATION
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
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Material is extremely destructive to the tissue of the
mucous membranes and upper respiratory tract.
Ingestion May be harmful if swallowed. Causes burns.
Skin May be harmful if absorbed through skin. Causes skin burns.
Eyes Causes eye burns.
Signs and Symptoms of Exposure
Material is extremely destructive to tissue of the mucous membranes and upper respiratory tract, eyes, and
skin., spasm, inflammation and edema of the larynx, spasm, inflammation and edema of the bronchi,
pneumonitis, pulmonary edema, burning sensation, Cough, wheezing, laryngitis, Shortness of breath,
Headache, Nausea
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
PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Product
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
ADR/RID
UN-Number: 2735 Class: 8 Packing group: II
Proper shipping name: AMINES, LIQUID, CORROSIVE, N.O.S. ((R)-(+)-N-allyl-α-methylbenzylamine)
IMDG
UN-Number: 2735 Class: 8 Packing group: II EMS-No: F-A, S-B
Proper shipping name: AMINES, LIQUID, CORROSIVE, N.O.S. ((R)-(+)-N-allyl-α-methylbenzylamine)
Marine pollutant: No
IATA
UN-Number: 2735 Class: 8 Packing group: II
Proper shipping name: Amines, liquid, corrosive, n.o.s. ((R)-(+)-N-allyl-α-methylbenzylamine)

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.

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Section 16. OTHER INFORMATION
Text of H-code(s) and R-phrase(s) mentioned in Section 3
Eye Dam. Serious eye damage
H314 Causes severe skin burns and eye damage.
Skin Corr. Skin corrosion
C Corrosive
R34 Causes burns.
Further information
Copyright 2010 Co. 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. Co., shall not be held liable for any damage resulting from
handling or from contact with the above product. See 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：

  (R)-(+)-N-烯丙基-α-甲基苄胺 在 tris(dibenzylideneacetone)dipalladium (0) 、 RhCl(PPh₃)3 4-二甲氨基吡啶 、 氢氧化钾 、 lithium hydroxide 、 tetrafluoroboric acid 、 sodium azide 、 三丁基膦 、 碘 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， -78.0~110.0 ℃ 、101.33 kPa 条件下， 反应 138.0h， 生成 (3R,5R,6R,αR)-3-(N-α-methylbenzylamino)-5-hydroxy-6-aminoheptanoic acid
  参考文献：
  名称：

  通过酰胺化锂共轭物的加成合成不对称的sperapbillins B和D。

  摘要：

  将非手性锂（R）-N-烯丙基-N-α-甲基苄基酰胺的非对映选择性共轭加成到（2E，5E）-庚二烯酸甲酯中，然后进行保护基团处理，然后进行碘代环氨基甲酸酯化，可以得到通往核心片段甲基（3R，脂蛋白B和D的5R，6R）-3,6-二氨基-5-羟基庚酸酯。通过用丙酮处理，很容易实现该核心氨基酸的C-3和C-6伯氨基之间的区分。 ，6-异亚丙基和C-3-亚胺保护的二胺，随后C-6-氮的区域选择性酰化促进了总产率为10.8％的斯培比林D的总合成，以及首次总产率为5.8％的斯培比林B的不对称合成。 。

  DOI：

  10.1039/b404962d
• 作为产物：
  描述：

  methyl {N-allyl-N-[(1R)-1-phenylethyl]amino}propanoate 在 lithium diisopropyl amide 、 zinc dibromide 作用下， 以 乙醚 为溶剂， 生成 (R)-(+)-N-烯丙基-α-甲基苄胺
  参考文献：
  名称：

  Diastereocontrolled Synthesis of Enantioenriched 3,4-Disubstituted β-Prolines

  摘要：

  [graphics]Enantioenriched 3,4-disubstituted beta-prolines have been prepared with a high diastereocontrol through a carbometalation reaction or through a domino Michael addition/carbometalation reaction.

  DOI：

  10.1021/jo061603h

文献信息

• Kolbe Anodic Decarboxylation as a Green Way To Access 2-Pyrrolidinones
  作者：Mathilde Quertenmont、Iain Goodall、Kevin Lam、István Markó、Olivier Riant

  DOI：10.1021/acs.orglett.0c00056

  日期：2020.3.6

  pharmaceutical industry. In this Article, we disclose an effective and environmentally friendly pyrrolidinone synthesis using electrosynthesis. The newly developed methodology includes a Kolbe decarboxylation, followed by an intramolecular radical cyclization and a radical-radical cross-coupling.

  促智化合物是一组具有药理活性的吡咯烷酮。这些增强认知特性并拥有广阔处方领域的分子，是制药行业特别感兴趣的合成靶标。在本文中，我们公开了一种利用电合成有效且环保的吡咯烷酮合成方法。新开发的方法包括Kolbe脱羧，然后进行分子内自由基环化和自由基-自由基交叉偶联。
• 1,1′-Binaphthyldiamine-Based Lewis Bases as Readily Available and Efficient Organocatalysts for the Reduction of<i>N</i>-Aryl and<i>N</i>-Alkyl Ketimines
  作者：Stefania Guizzetti、Maurizio Benaglia、Giuseppe Celentano

  DOI：10.1002/ejoc.200900524

  日期：2009.8

  development of simple, low-cost, efficient, and sustainable routes to enantiomerically pure amines is a topic of extraordinary interest, specially in view of future industrial applications. In this context, we wish to report a chemical and stereochemical efficient synthesis of chiral amines through the Lewis base activated trichlorosilane reduction of ketimines. An organocatalyst, easily prepared in a single

  开发对映异构纯胺的简单、低成本、高效和可持续的路线是一个非常有趣的话题，特别是考虑到未来的工业应用。在这种情况下，我们希望通过路易斯碱活化的三氯硅烷还原酮亚胺来报告手性胺的化学和立体化学有效合成。有机催化剂，通过吡啶甲酸和市售的 1,1'-联萘二胺的缩合很容易在一个步骤中制备，是这种无金属方法的关键要素，它允许以高产率合成手性仲胺和伯胺，并且立体选择性。值得注意的是，此类催化剂能够促进 N-烷基酮亚胺的还原，通常以定量收率和高达 87% 的对映选择性；值得一提的是，对于此类转化，迄今为止仅报道了一种其他有机催化系统。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Structure guided design of a series of sphingosine kinase (SphK) inhibitors
  作者：Darin J. Gustin、Yihong Li、Matthew L. Brown、Xiaoshan Min、Mike J. Schmitt、Malgorzata Wanska、Xiaodong Wang、Richard Connors、Sheere Johnstone、Mario Cardozo、Alan C. Cheng、Shawn Jeffries、Brendon Franks、Shyun Li、Shanling Shen、Mariwil Wong、Holger Wesche、Guifen Xu、Timothy J. Carlson、Matthew Plant、Kurt Morgenstern、Karen Rex、Joanna Schmitt、Angela Coxon、Nigel Walker、Frank Kayser、Zhulun Wang

  DOI：10.1016/j.bmcl.2013.06.030

  日期：2013.8

  inhibition of both isoforms is likely required to block SphK dependent angiogenesis. A structure based approach was used to design and synthesize a series of SphK inhibitors resulting in the identification of the first potent inhibitors of both isoforms of human SphK. Additionally, to our knowledge, this series of inhibitors contains the only sufficiently potent inhibitors of murine SphK1 with suitable

  鞘氨醇-1-磷酸（S1P）信号在有丝分裂，细胞迁移和血管生成中起着至关重要的作用。鞘氨醇激酶（SphKs）催化鞘磷脂代谢中的关键步骤，从而导致S1P的产生。SphK有两种同工型，对SphK缺陷小鼠的观察表明，这两种同工型可以弥补彼此的损失。因此，可能需要抑制两种同工型才能阻断SphK依赖性血管生成。基于结构的方法用于设计和合成一系列SphK抑制剂，从而鉴定出人类SphK两种同工型的第一种有效抑制剂。此外，据我们所知，
• A diastereodivergent strategy for the asymmetric syntheses of (−)-martinellic acid and (−)-4-epi-martinellic acid
  作者：Stephen G. Davies、Ai M. Fletcher、James A. Lee、Thomas J.A. Lorkin、Paul M. Roberts、James E. Thomson

  DOI：10.1016/j.tet.2013.09.013

  日期：2013.11

  Asymmetric syntheses of (−)-martinellic acid and (−)-4-epi-martinellic acid were achieved in 20 steps from commercially available starting materials using a diastereodivergent strategy. The conjugate addition of lithium (R)-N-allyl-N-(α-methyl-p-methoxybenzyl)amide to tert-butyl (E)-3-[2′-(N,N-diallylamino)-5′-bromophenyl]propenoate and alkylation of the resultant β-amino ester with methyl bromoacetate

  的不对称合成（ - ） - martinellic酸和（ - ） - 4-外延-martinellic苯甲酸在20步从使用diastereodivergent策略市售原料来实现。共轭加成锂（[R ）- ñ -allyl- ñ - （α -甲基p甲氧基苄基）酰胺叔丁基（ë）-3- [2' - （Ñ，Ñ-diallylamino）-5'-溴-苯基]丙烯酸甲酯，并用溴乙酸甲酯得到的β氨基酯的烷基化，使用以分别安装C（9B）和C（3a）的立构中心，关键步骤。随后环化为相应的吡咯并喹啉-2-酮并还原C（4）-羰基，然后进行两个互补的烯化反应和分子内迈克尔加成反应，这两个分子都形成了该三环分子结构的C（4）-顶基> 99：1博士 （ - ） - martinellic酸，并且对于第一次，（ - ） - 4-提供访问这些模板随后阐述外延-martinellic酸。
• Asymmetric synthesis of homochiral differentially protected bis-β-amino acid scaffolds
  作者：Steven D Bull、Stephen G Davies、Paul M Roberts、Edward D Savory、Andrew D Smith

  DOI：10.1016/s0040-4020(02)00369-1

  日期：2002.6

  strategy for the asymmetric synthesis of homochiral [(R,R)- or (S,S)-], or meso-(R,S) bis-β-amino acid scaffolds, formally resulting from the stepwise conjugate addition of two differentially protected homochiral lithium amides to two α,β-unsaturated esters attached to a central arene, is demonstrated. Further manipulation enables the efficient synthesis of orthogonally protected pseudo-meso or pseudo-C2

  不对称合成纯手性[（R，R）-或（S，S）-]或内消旋-（R，S）bis-β-氨基酸支架的不对称合成的策略，这是由两个不同的化合物通过逐步共轭添加而形成的证明了对连接到中心芳烃上的两个α，β-不饱和酯的保护的手性锂酰胺。进一步的操作使得能够通过选择性的N-苄基或N-烯丙基脱保护作用，有效地合成正交保护的伪内消旋或伪C 2对称骨架，从而实现区域，立体和化学选择性官能化。