三乙基-d15-胺 | 66688-79-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 三乙基-d15-胺
• 中文别名: 三乙胺-D15
• 英文名称: [D₁₅]triethylamine
• 英文别名: triethylamine-d₁₅；deuterated triethylamine；Triethyl-d15-amine；1,1,2,2,2-pentadeuterio-N,N-bis(1,1,2,2,2-pentadeuterioethyl)ethanamine
• CAS: 66688-79-7
• 化学式: C₆H₁₅N
• 分子量: 116.073
• InChiKey: ZMANZCXQSJIPKH-NLBPYYKNSA-N

物化性质

• 熔点：
  -115 °C(lit.)
• 沸点：
  88.8 °C(lit.)
• 密度：
  0.835 g/mL
• 闪点：
  20 °F
• 溶解度：
  少许溶于甲醇
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  F,C
• WGK Germany：
  3
• 危险品运输编号：
  UN 1296 3/PG 2

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Triethyl-d15-amine
CAS-No. : 66688-79-7

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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]
Flammable liquids (Category 2)
Acute toxicity, Inhalation (Category 4)
Acute toxicity, Dermal (Category 4)
Acute toxicity, Oral (Category 4)
Skin corrosion (Category 1A)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Highly flammable. Harmful by inhalation, in contact with skin and if swallowed. Causes severe burns.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Danger
Hazard statement(s)
Highly flammable liquid and vapour.
Harmful if swallowed.
Harmful in contact with skin.
Causes severe skin burns and eye damage.
Harmful if inhaled.
Precautionary statement(s)
Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
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.
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)
R11 Highly flammable.
R20/21/22 Harmful by inhalation, in contact with skin and if swallowed.
R35 Causes severe burns.
S-phrase(s)
S3 Keep in a cool place.
S16 Keep away from sources of ignition - No smoking.
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S29 Do not empty into drains.
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
Lachrymator.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C6D15N
Molecular Weight : 116,28 g/mol
Component Concentration
Triethyl-d15-amine
CAS-No. 66688-79-7 -

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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
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
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
For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large
fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or
spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of
water.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
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 vapors, mist or gas. Ensure adequate ventilation.
Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapours accumulating to
form explosive concentrations. Vapours can accumulate in low areas.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
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.
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.
Specific end use(s)
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, 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).

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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 Melting point/range: -115 °C - lit.
point
f) Initial boiling point and 88,8 °C - lit.
boiling range
g) Flash point -7 °C - closed cup
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 0,832 g/cm3
n) Water solubility no data available
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
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
Heat, flames and sparks. Extremes of temperature and direct sunlight.
Incompatible materials
acids, Oxidizing agents
Hazardous decomposition products
Other 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 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
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
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
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. 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: 1296 IMDG: 1296 IATA: 1296
UN proper shipping name
ADR/RID: TRIETHYLAMINE
IMDG: TRIETHYLAMINE
IATA: Triethylamine
Transport hazard class(es)
ADR/RID: 3 (8) IMDG: 3 (8) IATA: 3 (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
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

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  三乙基-d15-胺 在 吡啶 、 2-吡啶甲酸 、 iron(III) chloride hexahydrate 、 叔丁基苯甲酸 、 水 作用下， 生成
  参考文献：
  名称：

  Fe催化的叔胺α-C-H氧化的机理研究

  摘要：

  我们报告了铁基催化剂体系的详细机械研究，该体系可对多种胺进行α-CH氧化。与其他影响叔胺α-C-H氧化的催化剂相反，正在研究的系统仅使用过氧酯作为氧化剂。更常见的氧化剂（例如t先前报道的通过自由基途径影响胺氧化的BuOOH）不能与上述催化剂体系结合提供胺α-CH氧化产物。本文所述的研究采用了初始速率动力学，动力学分布，DFT计算以及Eyring，动力学同位素效应，Hammett，配体配位和EPR研究来阐明Fe催化剂体系。所获得的数据表明，催化机理是通过在配位的底物分子处的CH抽象来进行的。决定速率的步骤是通过Fe（IV）的羰基合成途径或在带有结合氧化剂的Fe（II）中间体的2电子途径进行的。DFT计算表明，Fe（IV）羰基合成机理将是这两种可能性的首选途径。3 t Bu到t BuOOH。总体而言，所获得的力学数据支持非经典的铁催化途径，该途径需要与底物结合，从而诱导对α-CHH功能化的选择性。

  DOI：

  10.1002/cctc.202001382
• 作为产物：
  描述：

  三乙胺 在 氘代苯 、 C₂₄H₅₁IrP₂ 作用下， 以 环辛烷 为溶剂， 反应 24.0h， 生成 三乙基-d15-胺
  参考文献：
  名称：

  铱氢化物与基于环己基的钳配体的配合物：通量和氘交换

  摘要：

  Two hydride compounds with aliphatic pincer ligands, (PCyP)IrH2 (PCyP = {cis-1,3-bis[(di-tert-butylphosphino)methyl]cyclohexane}(-) (1) and (PCyP)IrH4 (2), have been studied, with emphasis on features where such systems differ from arene-based analogues. Both compounds reveal relatively rapid exchange between alpha-C-H and Ir-H, which can occur via formation of carbene or through demetalation, with nearly equal barriers. This observation is confirmed by deuterium incorporation into the alpha-C-H position. Complex 1 can reversibly add an N-2 molecule, which competes with the alpha-agostic bond for a coordination site at iridium. The hydrogen binding mode in tetrahydride 2 is discussed on the basis of NMR and IR spectra, as well as DFT calculations. While the interpretation of the data is somewhat ambiguous, the best model seems to be a tetrahydride with minor contribution from a dihydrido-dihydrogen complex. In addition, the catalytic activity of 1 in deuterium exchange using benzene-d(6) as a deuterium source is presented.

  DOI：

  10.1021/acs.organomet.6b00324
• 作为试剂：
  描述：

  2-苯基乙炔基胺 在 氘代甲醇 、 (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate 、 sodium hydride 、 三乙胺 、 三乙基-d15-胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 25.0h， 生成 1,3-dimethyl-4-(phenylmethyl-d2)quinolin-2(1H)-one
  参考文献：
  名称：

  1,7-烯炔的光化学发散闭环复分解：螺环喹啉-2-酮的高效合成

  摘要：

  提出了一种使用α-氨基作为烯烃解构助剂进行1,7-烯炔闭环复分解的光催化方法。初步机理研究表明，分子内1,5-氢原子转移是α-氨基自由基产生和β-断裂的关键，而芳烃的脱芳构化和环丙烷的开环是构建螺环喹啉-2-的关键。那些。该方法凸显了闭环1,7-烯炔复分解的潜力，为螺环喹啉-2-酮的合成提供了一种绿色、高效、一步经济的方法。

  DOI：

  10.1021/acs.orglett.4c02332

文献信息

• Aerobic α,β-C(sp³)–H Bond Difunctionalization and C–N Bond Cleavage of Triethylamine: Difunctional Ammonium Iodide Enabling the Regioselective Synthesis of 4-Arylpyrimido[1,2-<i>b</i>]indazoles
  作者：Qinghe Gao、Xinya Han、Peiyuan Tong、Zhiang Zhang、Haotian Shen、Yanrong Guo、Suping Bai

  DOI：10.1021/acs.orglett.9b02218

  日期：2019.8.2

  A novel method for the regioselective synthesis of 4-arylpyrimido[1,2-b]indazoles has been developed via the dual C(sp3)–H bond functionalization and C–N bond cleavage of triethylamine. The elusive acyclic enamine intermediates are effectively in situ generated and captured by aromatic aldehydes to form a wide array of tricyclic products from 3-aminoindazoles under the NH4I-mediated aerobic oxidative

  通过三乙胺的双C（sp 3）-H键官能化和C-N键裂解，开发了一种新的区域选择性合成4-芳基嘧啶[1,2- b ]吲唑的新方法。难以捉摸的无环烯胺中间体可在NH 4 I介导的需氧氧化条件下有效地原位生成并被芳族醛捕获，从而形成多种由3-氨基吲唑形成的三环产物。该反应具有容易获得的原料，绿色和经济条件以及有价值的产品的特点。
• Direct synthesis of 2-methylpyridines <i>via</i> I₂-triggered [3 + 2 + 1] annulation of aryl methyl ketoxime acetates with triethylamine as the carbon source
  作者：Qinghe Gao、Huijuan Yan、Manman Wu、Jiajia Sun、Xiqing Yan、Anxin Wu

  DOI：10.1039/c8ob00349a

  日期：——

  A facile and efficient [3 + 2 + 1] annulation of aryl methyl ketoxime acetates and triethylamine for the synthesis of 2-methylpyridines was disclosed. This reaction demonstrated that I2 was effective in triggering N–O bond cleavage of oxime acetates generating imine radicals. It was noteworthy that this transformation employed triethylamine as the carbon source for the direct formation of pyridines

  公开了用于合成2-甲基吡啶的芳基甲基酮肟乙酸酯和三乙胺的简便且有效的[3 + 2 +1]环合反应。该反应表明，I 2可有效引发肟肟乙酸酯的N–O键裂解，产生亚胺基。值得注意的是，该转化使用三乙胺作为碳源，用于直接形成吡啶和引入甲基。
• I₂-Catalyzed Aerobic α,β-Dehydrogenation and Deamination of Tertiary Alkylamines: Highly Selective Synthesis of Polysubstituted Pyrimidines via Hidden Acyclic Enamines
  作者：Qinghe Gao、Manman Wu、Ke Zhang、Ning Yang、Mengting Liu、Juan Li、Lizhen Fang、Suping Bai、Yongtao Xu

  DOI：10.1021/acs.orglett.0c02001

  日期：2020.7.17

  β-dehydrogenation and deamination of tertiary alkylamines. This I2-catalyzed dehydrogenative multicomponent procedure utilizes simple aldehydes to trap the hidden enamine intermediates and suspend generation of azadienes from amidines, enabling the difunctionalization of a vicinal C(sp3)–H bond. These studies provide valuable possibilities for the introduction of aliphatic substituents and show how to

  通过叔烷基胺的α，β-脱氢和脱氨基反应，提出了一种新颖而有效的嘧啶骨架入口。这种I 2催化的脱氢多组分方法利用简单的醛类来捕获隐藏的烯胺中间体并中止从am中生成氮杂二烯，从而使邻位C（sp 3）-H键双官能化。这些研究为引入脂族取代基提供了宝贵的可能性，并显示了如何转换为新的反应性形式。
• Vinylation of α-Aminoazoles with Triethylamine: A General Strategy to Construct Azolo[1,5-<i>a</i>]pyrimidines with a Nonsubstituted Ethylidene Fragment
  作者：Qinghe Gao、Zhenhua Sun、Qinfei Xia、Ruonan Li、Wenlong Wang、Siwei Ma、Yixin Chai、Manman Wu、Wei Hu、Péter Ábrányi-Balogh、György M. Keserű、Xinya Han

  DOI：10.1021/acs.orglett.1c00571

  日期：2021.4.2

  A new general synthesis of pharmaceutically important azolo[1,5-a]pyrimidines starting from widely available 3(5)-aminoazoles, aldehydes, and triethylamine is developed. The key is to enable the vinylation reaction that allows the in situ generation of elusive acyclic enamines and the subsequent annulation reaction to occur. This direct and practical strategy is capable of constructing a range of 5

  从广泛可用的3（5）-氨基唑，醛和三乙胺开始，开发了一种重要的药学上重要的偶氮[1,5- a ]嘧啶的新的一般合成方法。关键是要实现乙烯基化反应，该反应可以原位产生难以捉摸的无环烯胺，并随后发生环化反应。这种直接而实用的策略能够构建一系列5,6-未取代的吡唑并[1,5- a ]嘧啶和[1,2,4]三唑并[1,5- a ]嘧啶。更重要的是，该方案为制备临床使用的扎来普隆提供了一种简明的合成途径。
• Photoredox-Catalyzed C_α–H Cyanation of Unactivated Secondary and Tertiary Aliphatic Amines: Late-Stage Functionalization and Mechanistic Studies
  作者：Ozgur Yilmaz、Martins S. Oderinde、Marion H. Emmert

  DOI：10.1021/acs.joc.8b01700

  日期：2018.9.21

  general, high-yielding amine Cα–H cyanation protocol via photoredox catalysis. Inexpensive NaCN is employed as the cyanide source and air is the external oxidant, resulting in mild and highly functional group tolerant conditions. Notably, efficient Cα–H cyanations of secondary and tertiary aliphatic amines and of complex, biologically active compounds (drugs) can be performed using the established methodology

  本文描述了开发和一个一般地，高产胺的C机理研究α -H氰化经由photoredox催化协议。廉价的NaCN用作氰化物源，空气是外部氧化剂，导致温和且高度官能团耐受的条件。值得注意的是，高效的C α -H的cyanations二级和三级可使用所建立的方法进行脂族胺和复杂的，生物活性化合物（药物）的。机理研究表明，该羧酸添加剂具有三种作用：形成稳定的半胱氨酸中间体，通过使底物质子化来防止催化剂分解以及调节光激发催化剂物种的荧光猝灭。