(S)-(-)-N-(2-羟乙基)-ALPHA-苯基乙胺 | 6623-43-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (S)-(-)-N-(2-羟乙基)-ALPHA-苯基乙胺
• 中文别名: (S)-(-)-N-(2-羟乙基)-Alpha-苯基乙胺
• 英文名称: (S)-(-)-N-(2-hydroxyethyl)-α-methylbenzylamine
• 英文别名: (-)-N-(2-hydroxyethyl)-α-phenylethylamine；(S)-2-[(1-phenylethyl)amino]-ethanol；(S)-2-(1-phenylethylamino)-ethanol；N-((S)-(-)-α-methylbenzyl)ethanolamine；(S)-2-(α-methylbenzylamino)-1-ethanol；2-{[(1S)-1-phenylethyl]amino}ethan-1-ol；2-[[(1S)-1-phenylethyl]amino]ethanol
• CAS: 6623-43-4；80548-31-8；66849-29-4
• 化学式: C₁₀H₁₅NO
• mdl: MFCD01862172
• 分子量: 165.235
• InChiKey: GXIWMXAAPLZOBY-VIFPVBQESA-N

物化性质

• 熔点：
  76°C
• 沸点：
  293.09°C (rough estimate)
• 密度：
  1.0203 (rough estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2922199090
• 储存条件：
  存放于阴凉干燥处即可。

SDS

Name:	(-)-N-(2-Hydroxyethyl)-Alpha-Phenylethylamine 99% Material Safety Data Sheet
Synonym:	None Known
CAS:	66849-29-4

Section 1 - Chemical Product MSDS Name:(-)-N-(2-Hydroxyethyl)-Alpha-Phenylethylamine 99% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
66849-29-4	(-)-N-(2-Hydroxyethyl)-Alpha-Phenyleth	99%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. May cause methemoglobinemia, cyanosis (bluish discoloration of skin due to deficient oxygenation of the blood), convulsions, and death. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May cause methemoglobinemia, cyanosis (bluish discoloration of skin due to deficient oxygenation of the blood), convulsions, tachycardia, dyspnea (labored breathing), and death. May be harmful if inhaled. Can produce delayed pulmonary edema.
Chronic:
May cause methemoglobinemia, which is characterized by chocolate-brown colored blood, headache, weakness, dizziness, breath shortness, cyanosis (bluish skin due to deficient oxygenation of blood), rapid heart rate, unconsciousness and possible death. Effects may be delayed.

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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.
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. Wash mouth out with 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. Do NOT use mouth-to-mouth resuscitation.
Notes to Physician:
Treat symptomatically and supportively. For methemoglobinemia, administer oxygen alone or with Methylene Blue depending on the methemoglobin concentration in the blood.
Antidote: Methylene blue, alone or in combination with oxygen is indicated as a treatment in nitrite induced methemoglobinemia.

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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. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

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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. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 66849-29-4: 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: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C10H15NO
Molecular Weight: 165.1111

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, 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# 66849-29-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(-)-N-(2-Hydroxyethyl)-Alpha-Phenylethylamine, 99% - Not listed by ACGIH, IARC, or NTP.

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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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 66849-29-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 66849-29-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 66849-29-4 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

制备方法

有机试剂、医药中间体。

用途简介 用途

有机试剂、医药中间体。

反应信息

• 作为反应物：
  描述：

  (S)-(-)-N-(2-羟乙基)-ALPHA-苯基乙胺 在 氯化亚砜 、 potassium tert-butylate 、 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 7.17h， 生成 [1(1S),2S]-1-(1-phenyl-ethyl)-azetidine-2-carbonitrile
  参考文献：
  名称：

  氮杂环丁烷-2-羧酸的实用不对称制备

  摘要：

  描述了氮杂环丁烷-2-羧酸的两种对映异构体的简便直接合成。合成过程从廉价的化学品中分离出来，并允许在五到六个步骤中生产实际数量的每种对映异构体。合成亮点包括利用分子内烷基化构建氮杂环丁烷环，以及使用旋光性α-甲基苄基胺作为手性助剂。

  DOI：

  10.1021/jo0515881
• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 在 sodium hydroxide 、 硼烷四氢呋喃络合物 、 potassium carbonate 作用下， 生成 (S)-(-)-N-(2-羟乙基)-ALPHA-苯基乙胺
  参考文献：
  名称：

  吗啉-2,3-二酮和2-羟基吗啉-3-酮的合成：阿瑞匹坦的中间体

  摘要：

  据报道，由N-取代的β-氨基醇制备吗啉-2，3-二酮和2-羟基吗啉-3-酮。这些是阿瑞吡坦合成和开发中有用的中间体。

  DOI：

  10.1016/j.tetlet.2004.09.185
• 作为试剂：
  描述：

  二异丙基锌 、 苯甲醛 在 N-甲基麻黄碱 、 (S)-(-)-N-(2-羟乙基)-ALPHA-苯基乙胺 作用下， 以 正己烷 为溶剂， 生成 (R)-2-methyl-1-phenylpropan-1-ol 、 (S)-(-)-2-甲基-1-苯基-1-丙醇
  参考文献：
  名称：

  通过两个手性催化剂的协同操作，对映体选择性的逆转现象。

  摘要：

  通过将两种手性β-氨基醇催化剂混合，可以观察到二异丙基锌不对称加成到醛中时对映体选择性的逆转现象。使用具有各自对映选择性的两种手性催化剂的混合物形成相反的对映体产物。

  DOI：

  10.1039/c1cc10136f

文献信息

• Structural Studies on Bioactive Compounds. 34. Design, Synthesis, and Biological Evaluation of Triazenyl-Substituted Pyrimethamine Inhibitors of <i>Pneumocystis carinii</i> Dihydrofolate Reductase
  作者：David C. M. Chan、Charles A. Laughton、Sherry F. Queener、Malcolm F. G. Stevens

  DOI：10.1021/jm0108698

  日期：2001.8.1

  The triazenyl-pyrimethamine derivative 3a (TAB), a potent and selective inhibitor of Pneumocystis carinii DHFR, was selected as the starting point for a lead optimization study. Molecular modeling studies, corroborated by a recent crystal structure determination of the ternary complex of P. carinii DHFR--NADPH bound to TAB, predicted that modifications to the acetoxy residue of the lead inhibitor could

  选择了三氮烯基-乙胺嘧啶衍生物3a（TAB）（一种有效的选择性卡氏肺孢子虫DHFR抑制剂）作为前导优化研究的起点。分子建模研究得到了最近对TAB结合的Carinii DHFR-NADPH三元复合物晶体结构测定的证实，预测对铅抑制剂乙酰氧基残基的修饰可利用活性位点附近的结合机会由残基Ile33，Lys37和Leu72结合。预测用给电子基团和吸电子基团取代苄基部分可探测与卡氏疟原虫唯一的氨基酸Phe69的面缘相互作用。新的三氮烯10a-v和12a-f是通过将氨基乙胺的四氟硼酸重氮盐6b与取代的苄胺或苯乙胺偶联而制得的。在新的抗卡氏疟原虫DHFR抑制剂中，最有效的是萘基甲基取代的三氮烯10t（IC（50）：0.053 microM），但对大鼠肝脏DHFR的效价更大幅度的升高导致选择性降低（比率为大鼠肝脏DHFR IC（50）/卡氏毕赤酵母DHFR IC（50）：5.36）与原始铅结构3a的比率（大鼠肝脏DHFR
• Synthesis of [¹³C₄]-labeled 2′-deoxymugineic acid
  作者：Martin R. Walter、Daniel Artner、Christian Stanetty

  DOI：10.1002/jlcr.3242

  日期：2014.11

  The phytosiderophore 2′-deoxymugineic acid (DMA) is exuded via the root system by all grasses (including important crop plants like rice, wheat and barley) to mobilize Fe(III) from soil and improve plant Fe nutrition, crucial for high crop yields. Elucidation of the biogeochemistry of 2′-deoxymugineic acid in the rhizosphere requires its quantification in minute amounts. To this end, 13C4-DMA was synthesized for the first time, from cheap isotopically labeled starting materials. The synthetic route utilizes l-allyl(13C2)glycine and l-(2-13C)azetidine (13C)carboxylic acid as versatile labeled building blocks. The title compound was recently used as an internal standard for analysis of soil and plant samples allowing the first accurate quantification of DMA in these matrices by means of LC-MS/MS. It is furthermore used in tracer experiments investigating biodegradation of DMA in soil.

  所有禾本科植物（包括水稻、小麦和大麦等重要作物）都会通过根系渗出植物苷元 2′-脱氧木精酸 (DMA)，以动员土壤中的铁(III)，改善植物的铁营养状况，这对作物高产至关重要。要阐明根圈中 2′-脱氧木精酸的生物地球化学，需要对其进行微量定量。为此，我们首次利用廉价的同位素标记起始材料合成了 13C4-DMA。合成路线利用 l-烯丙基（13C2）甘氨酸和 l-（2-13C）氮杂环丁烷（13C）羧酸作为多功能标记构建模块。标题化合物最近被用作土壤和植物样品分析的内标，首次通过 LC-MS/MS 对这些基质中的 DMA 进行了精确定量。此外，它还被用于研究土壤中 DMA 生物降解的示踪实验。
• Process for preparation of pyrimidine derivatives
  申请人：Uhan Corporation

  公开号：US05990311A1

  公开（公告）日：1999-11-23

  The present invention relates to a process for preparation of 5,6-dimethyl-2-(4-fluorophenyl-amino)-4-(1-methyl-1,2,3,4-tetrahydroisoqui nolin-2-yl)pyrimidine represented by the following formula (I), ##STR1## and its acid addition salts by reacting a pyrimidine derivative represented by the formula (II-A), ##STR2## in which Hal represents a halogen, with 1-methyl-1,2,3,4-tetrahydroisoquinoline represented by the formula (III), ##STR3##

  本发明涉及一种制备5,6-二甲基-2-(4-氟苯基氨基)-4-(1-甲基-1,2,3,4-四氢异喹啉-2-基)嘧啶（如下式（I）所示）的过程，以及通过将由下式（II-A）表示的嘧啶衍生物与由下式（III）表示的1-甲基-1,2,3,4-四氢异喹啉反应而制备其酸盐。
• The use of heterocycles for the conformational restriction of biologically active peptoids
  作者：David C. Horwell、Russell A. Lewthwaite、Martyn C. Pritchard、Giles S. Ratcliffe、J. Ronald Rubin

  DOI：10.1016/s0040-4020(98)00092-1

  日期：1998.4

  A series of piperazinone ring systems have been synthesised as a means of evaluating the effect of conformational restriction on high affinity non-peptide NK1, NK3 and CCK-B receptor ligands. The synthesis of the targeted heterocycles is described along with a discussion of their affinities for their respective receptor types.

  已经合成了一系列哌嗪酮环系统，作为评估构象限制对高亲和力非肽NK 1，NK 3和CCK-B受体配体的影响的手段。描述了靶向杂环的合成，并讨论了它们对各自受体类型的亲和力。
• Chemodivergent Synthesis of 7-Aryl/alkyl-6-hydroxy-1,4-oxazepan-5-ones and 2-[Aryl/alkyl(hydroxy)methyl]morpholin-3-ones from a Common Epoxyamide Precursor
  作者：Joel Terán、David Aparicio、Luis Roa、Dino Gnecco、Jorge Juárez、María Orea、Angel Mendoza、Marcos Flores-Alamo、Laurent Micouin

  DOI：10.1055/s-0030-1260064

  日期：2011.7

  We present here a regiospecific synthesis of 7-alkyl- or 7-aryl-6-hydroxy-1,4-oxazepan-5-ones and 2-[aryl(hydroxy)methyl]- or 2-(1-hydroxyalkyl)morpholin-3-ones from a diastereomeric mixture of trans-3-alkyl- or -3-aryl-N-(2-hydroxyethyl)-N-(1-phenylethyl)oxirane-2-carboxamides. This chemodivergent synthesis is easily controlled by an appropriate choice of cyclization reaction conditions.

  我们在此提出了7-烷基-或7-芳基-6-羟基-1,4-氧氮杂环-5-酮和2-[芳基(羟基)甲基]-或2-(1-羟基烷基)吗啉-的区域特异性合成。来自反式-3-烷基-或-3-芳基-N-(2-羟乙基)-N-(1-苯乙基)环氧乙烷-2-甲酰胺的非对映异构体混合物的3-酮。通过适当选择环化反应条件可以轻松控制这种化学发散合成。