(S)-2-氨基辛烷 | 34566-04-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (S)-2-氨基辛烷
• 中文别名: (S)-(+)-2-氨基辛烷；(S)-2-辛胺
• 英文名称: (S)-octan-2-amine
• 英文别名: (S)-2-aminooctane；(S)-2-octylamine；(2S)-octan-2-amine
• CAS: 34566-04-6
• 化学式: C₈H₁₉N
• 分子量: 129.246
• InChiKey: HBXNJMZWGSCKPW-QMMMGPOBSA-N

物化性质

• 沸点：
  163-165 °C
• 密度：
  0.77
• 闪点：
  50 °C
• 稳定性/保质期：
  如果遵照规格使用和储存，则不会分解，未有已知危险反应。避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  8
• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R22,R34
• WGK Germany：
  3
• 海关编码：
  2921199090
• 包装等级：
  II
• 危险类别：
  8
• 危险品运输编号：
  UN 2735
• 储存条件：
  请将贮藏器密封保存，在阴凉、干燥处存放，并确保工作环境有良好的通风或排气设施。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : (S)-2-Aminooctane
CAS-No. : 34566-04-6
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]
Acute toxicity, Oral (Category 4)
Skin corrosion (Category 1B)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed. Causes burns.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Danger
Hazard statement(s)
H302 Harmful if swallowed.
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.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R22 Harmful if swallowed.
R34 Causes burns.
S-phrase(s)
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).
Caution - substance not yet tested completely.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : (S)-2-Octylamine
Formula : C8H19N
Molecular Weight : 129,24 g/mol
Component Concentration
(S)-2-Aminooctane
CAS-No. 34566-04-6 -

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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
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.
Most important symptoms and effects, both acute and delayed
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
no data available
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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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.
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.
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.
Normal measures for preventive fire protection.
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.
Store under inert gas. Sensitive to carbon dioxide
Specific end uses
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
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 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, 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 no data available
boiling range
g) Flash point no data available
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 no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition 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
no data available
Incompatible materials
no data available
Hazardous 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
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 Harmful if swallowed. Causes burns.
Skin May be harmful if absorbed through skin. Causes skin burns.
Eyes Causes eye burns.
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
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: 2735 IMDG: 2735 IATA: 2735
UN proper shipping name
ADR/RID: AMINES, LIQUID, CORROSIVE, N.O.S. ((S)-2-Aminooctane)
IMDG: AMINES, LIQUID, CORROSIVE, N.O.S. ((S)-2-Aminooctane)
IATA: Amines, liquid, corrosive, n.o.s. ((S)-2-Aminooctane)
Transport hazard class(es)
ADR/RID: 8 IMDG: 8 IATA: 8
Packaging group
ADR/RID: II IMDG: II IATA: II
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：

  (S)-2-氨基辛烷 在 nickel 作用下， 反应 5.0h， 以92%的产率得到(R)-2-氨基辛烷
  参考文献：
  名称：

  镍纳米颗粒作为伯胺的外消旋催化剂

  摘要：

  通过将已知使苄胺外消旋的碱与镍 (II) 盐结合，获得了活性镍纳米颗粒，可用作脂肪族和苄基伯胺外消旋化的催化剂。纳米粒子在离子液体四丁基溴化铵中稳定，可以在几小时内以优异的选择性完成大多数外消旋化。通过使用具有双相外消旋步骤的两锅系统克服了强还原性外消旋化催化剂和酶促胺拆分催化剂的不相容性问题。含有胺的壬烷层与酰化酶和离子液体中的外消旋 Ni 纳米颗粒的连续接触允许成功超过动力学拆分的 50% 酰胺产率极限。

  DOI：

  10.1002/ejic.201300074
• 作为产物：
  描述：

  仲辛酮 在 磷酸吡哆醛 、 β-烟酰胺腺嘌呤二核苷酸 、 alcohol dehydrogenase from Candida parapsilosis-W₂₈₆A mutant 、 Bacillus megaterium ω-transaminase 、 二异丙胺 作用下， 以 aq. acetate buffer 为溶剂， 反应 24.0h， 生成 (S)-2-氨基辛烷
  参考文献：
  名称：

  一个简单的生物系统，可将外消旋醇高级联转化为对映纯胺。

  摘要：

  外消旋醇的胺化生产对映体纯胺是药物生产的重要绿色化学反应，需要简单有效的解决方案。在本文中，我们报道了胺化外消旋醇的级联生物转化的发展。该级联反应利用灵巧的醇脱氢酶（ADH）氧化外消旋醇，对映选择性转氨酶（TA）将酮中间体转化为手性胺，异丙基胺通过反向的级联反应再循环PMP和NAD +辅因子。该概念是通过使用（S）设计的灵巧的CpSADH-W286A证明的。）-对映选择性CpSADH作为进化的歧义ADH，对映选择性BmTA和异丙胺的第一个例子。开发了一种包含异丙胺和大肠杆菌（CpSADH-W286A / BmTA）的生物系统来表达这两种酶，用于消旋外消旋醇的胺化反应，以产生八种有用的高价值（S）胺，产率为72-99％，98-99 ％ee，提供了针对此类反应的简单实用的解决方案。

  DOI：

  10.1002/anie.202009733

文献信息

• Connecting Unexplored Protein Crystal Structures to Enzymatic Function
  作者：Fabian Steffen-Munsberg、Clare Vickers、Ahmad Thontowi、Sebastian Schätzle、Tony Tumlirsch、Maria Svedendahl Humble、Henrik Land、Per Berglund、Uwe T. Bornscheuer、Matthias Höhne

  DOI：10.1002/cctc.201200544

  日期：2013.1

  Digging in the database: Four synthetically useful transaminases for which no function was known were studied by evaluating a set of eight amino donors and seven acceptors (see figure). The four enzymes differ substantially in their catalytic properties and substrate preferences. We also used the enzymes in the asymmetric synthesis of a range of chiral amines and observed excellent enantioselectivities

  在数据库中进行挖掘：通过评估一组八个氨基供体和七个受体，研究了四个未知功能的合成有用的转氨酶（见图）。四种酶的催化特性和底物偏好存在很大差异。我们还在一系列手性胺的不对称合成中使用了这些酶，并观察到出色的对映选择性和转化率。
• Vicinal Diamines as Smart Cosubstrates in the Transaminase-Catalyzed Asymmetric Amination of Ketones
  作者：Stefan E. Payer、Joerg H. Schrittwieser、Wolfgang Kroutil

  DOI：10.1002/ejoc.201700253

  日期：2017.5.3

  Transaminases (TAs) have recently been established as catalysts for the asymmetric, reductive amination of prochiral ketones. Depending on the ketone substrate and the amine donor (the cosubstrate), equilibrium constants may limit high conversions; thus, methods to overcome this limitation are required. Removal of the co-product from the reaction equilibrium through spontaneous, intramolecular reactions

  转氨酶 (TA) 最近已被确定为前手性酮不对称还原胺化的催化剂。根据酮底物和胺供体（共底物），平衡常数可能会限制高转化率；因此，需要克服这种限制的方法。通过自发的分子内反应从反应平衡中去除副产物为这个问题提供了成功的解决方案。因此，这些胺供体被命名为“智能共底物”。在这里，我们比较了各种双功能胺供体，包括作为潜在结构共底物基序的连二胺。在 TA 催化的 1,2-二胺脱氨基作用后，所得 α-氨基酮的自发二聚化和氧化得到杂芳族吡嗪。
• Expanding Substrate Specificity of ω-Transaminase by Rational Remodeling of a Large Substrate-Binding Pocket
  作者：Sang-Woo Han、Eul-Soo Park、Joo-Young Dong、Jong-Shik Shin

  DOI：10.1002/adsc.201500239

  日期：2015.8.24

  by severe steric interference in a small active site pocket of ω‐transaminase (ω‐TA). Herein, we demonstrated that structure‐guided remodeling of a large pocket by a single point mutation, instead of excavating the small pocket, afforded desirable alleviation of the steric constraint without deteriorating parental activities toward native substrates. Molecular modeling suggested that the L57 residue

  通过生物催化转氨作用生产结构多样的手性胺受到ω-转氨酶（ω-TA）的一个小活性位点空间中的严重空间干扰的挑战。在本文中，我们证明了通过单点突变对大袋进行结构引导的重塑，而不是挖掘小袋，可实现空间约束的理想缓解，而不会降低亲本底物的亲本活动。分子建模表明人O骨菜中ω‐TA的L57残基用作闩锁，迫使笨重的基板与小袋进行空间干涉。通过L57A取代去除闩锁，可以重新定位小袋，并显着提高了对各种芳基烷基胺和烷基胺的活性（例如，α-丙基苄胺的k cat / K M增加1100倍）。这种方法可以提供一种简便的策略来扩大ω-TAs的底物特异性。
• In Vitro and In Vivo One-Pot Deracemization of Chiral Amines by Reaction Pathway Control of Enantiocomplementary ω-Transaminases
  作者：Sang-Woo Han、Youngho Jang、Jong-Shik Shin

  DOI：10.1021/acscatal.9b01546

  日期：2019.8.2

  Biocatalytic cascade conversion of racemic amines into optically pure ones using enantiocomplementary ω-transaminases (ω-TAs) has been developed by thermodynamic and kinetic control of reaction pathways where 12 competing reactions occur with pyruvate and isopropylamine used as cosubstrates. Thermodynamic control was achieved under reduced pressure for selective removal of a coproduct (i.e., acetone)

  通过对反应途径的热力学和动力学控制，利用丙酮酸和异丙胺作为共底物发生了12个竞争反应，通过对反应途径的热力学和动力学控制，已开发出利用对映体互补ω-转氨酶（ω-TAs）将消旋胺生物催化级联转化为光学纯的胺。在减压下实现了热力学控制，以选择性除去副产物（即丙酮），从而消除了六个不良反应。利用ω-TAs底物特异性的工程正交性进行动力学控制，从而可以抑制另外四个反应。两者合计，净反应途径可以针对两个所需的反应（即R-胺的氧化脱氨基和所得酮的还原性胺化成对映体S）。-胺）。这种策略可以对多种手性胺进行一锅除臭，其中ee S > 99％，生成的S-胺产品的反应收率达到85-99％。使用葡萄糖或1-苏氨酸作为廉价的氨基受体前体，可以在活的微生物中成功地进行体外级联反应，这表明合成的代谢途径能够使手性胺脱消脂，这在活生物体中从未观察到。
• Sequential Reductive Amination-Hydrogenolysis: A One-Pot Synthesis of Challenging Chiral Primary Amines
  作者：Thomas C. Nugent、Daniela E. Negru、Mohamed El-Shazly、Dan Hu、Abdul Sadiq、Ahtaram Bibi、M. Naveed Umar

  DOI：10.1002/adsc.201100250

  日期：2011.8

  Difficult-to-access chiral primary amines were formed in good to high yield and ee using a rare example of a one-pot synthesis from prochiral ketones (sequential reductive amination-hydrogenloysis). As a highlight we also demonstrate a one-pot reductive amination-hydrogenolysis-reductive amination (five reactions) of ortho-methoxyacetophenone resulting in the chiral diamine 1-(2-methoxyphenyl)ethy

  以良好至高产率并且形成难以访问手性伯胺EE使用一锅合成从前手性酮的一个罕见的例子（顺序还原性胺化-hydrogenloysis）。作为亮点，我们还证明了邻甲氧基苯乙酮的一锅还原胺化-氢解还原还原胺化（五个反应）产生了手性二胺1-（2-甲氧基苯基）乙基-（2-吡啶基甲基）-胺（4）（ 58％的总收率，> 99％ee），这是一种用于水性对映选择性羟醛反应的新型有机催化剂。