4-乙基氧丙基乙酸酯 | 4919-33-9

• 物质功能分类: 化学农药原药 - 杀虫剂中间体
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-乙基氧丙基乙酸酯
• 中文别名: 4-乙基氧丙基乙酸；4-乙氧基苯基乙酸；4-乙氧基苯乙酸
• 英文名称: 4-ethoxyphenylacetic acid
• 英文别名: 2-(4-ethoxyphenyl)acetic acid；p-ethoxyphenylacetic acid
• CAS: 4919-33-9
• 化学式: C₁₀H₁₂O₃
• mdl: MFCD00004346
• 分子量: 180.203
• InChiKey: ZVVWZNFSMIFGEP-UHFFFAOYSA-N

物化性质

• 熔点：
  87-90 °C(lit.)
• 沸点：
  318.5±17.0℃ (760 Torr)
• 密度：
  1.144±0.06 g/cm3 (20 ºC 760 Torr)
• 闪点：
  125.8±14.4℃
• 稳定性/保质期：
  常温常压下稳定，本品为白色固体，熔点87～90℃。不溶于水，可溶于苯、甲苯。

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xn
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2918990090
• 储存条件：
  常温下应存于避光、阴凉干燥处，并密封保存。

SDS

Name:	4-Ethoxyphenylacetic acid 98% Material Safety Data Sheet
Synonym:	Benzeneacetic acid, 4-ethoxy
CAS:	4919-33-9

Section 1 - Chemical Product MSDS Name:4-Ethoxyphenylacetic acid 98% Material Safety Data Sheet
Synonym:Benzeneacetic acid, 4-ethoxy

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
4919-33-9	Benzeneacetic acid, 4-ethoxy-	98	225-545-3

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: 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. 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.
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:

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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.
Extinguishing Media:
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:
Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
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# 4919-33-9: 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:
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: Powder
Color: slightly beige
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 87.00 - 90.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Not available.
Specific Gravity/Density: Not available.
Molecular Formula: C10H12O3
Molecular Weight: 180.20

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
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# 4919-33-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Benzeneacetic acid, 4-ethoxy- - 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
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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 4919-33-9: No information available.
Canada
CAS# 4919-33-9 is listed on Canada's NDSL List.
CAS# 4919-33-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 4919-33-9 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

对乙氧基苯乙酸是合成农药、医药及液晶材料的重要中间体，同时也是国际上广泛使用的燃油添加剂。

主要合成路线

文献报道的对乙氧基苯乙酸的合成路线主要有三条：

1. 以苯乙醚为原料：经氯甲基化、氰化、水解和酸化后得到。
2. 对甲基苯酚与硫酸二乙酯进行 Williamson 醚化，随后氯化、氰化、水解和酸化后得到。
3. 对乙氧基苯乙酮与单质硫及胺类化合物进行 Willgerodt 酰胺化重排，然后水解制得。

其中，路线1和路线2工艺较长，中间产物分离困难，并且都使用了剧毒品氰化钠；而路线3尽管步骤较少，但反应时间长且收率较低。

化学性质

对乙氧基苯乙酸为白色固体，熔点87～90℃，不溶于水，可溶于苯和甲苯。

用途

对乙氧基苯乙酸是拟除虫菊酯乙氰菊酯的中间体。

生产方法

其制备方法是在反应器中加入对乙氧基氰苄、氢氧化钾和乙二醇，加热搅拌反应。反应结束后，冷却至室温，进行酸化处理，并加入水和苯分层。油层蒸馏除去苯后，得到对乙氧基苯乙酸。

反应信息

• 作为反应物：
  描述：

  4-乙基氧丙基乙酸酯 在 sodium methylate 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 2-chloro-5-(4-ethoxyphenyl)-3-pyridinecarbonitrile
  参考文献：
  名称：

  Design, Synthesis, and Activity of a Series of Arylpyrid-3-ylmethanones as Type I Positive Allosteric Modulators of α7 Nicotinic Acetylcholine Receptors

  摘要：

  A series of novel arylpyrid-3-ylmethanones (7a-aa) were designed as modulators of alpha 7 nicotinic acetylcholine receptors (nAChRs). The methanones were found to be type I positive allosteric modulators (PAMs) of human alpha 7 nAChRs expressed in Xenopus ooctyes. Structure-activity relationship (SAR) studies resulted in the identification of compound 7v as a potent and efficacious type I PAM with maximum modulation of a nicotine EC5 response of 1200% and EC50 = 0.18 mu M. Compound 7z was active in reversing the effect of scopolamine in the novel object recognition (NOR) paradigm with a minimum effective ip dose of 1.0 mg/kg (2.7 mu mol/kg). This effect was blocked by the selective alpha 7 nAChR antagonist methyllycaconitine (MLA). These compounds are nAChRs that may have therapeutic value in restoring impaired sensory Alzheimer's disease. potent type I positive allosteric modulators of alpha 7 gating and cognitive deficits in schizophrenia and Alzheimer's disease.

  DOI：

  10.1021/jm400704g
• 作为产物：
  描述：

  对羟基苯乙腈 在 potassium carbonate 作用下， 生成 4-乙基氧丙基乙酸酯
  参考文献：
  名称：

  Werner, Justus Liebigs Annalen der Chemie, 1902, vol. 322, p. 160

  摘要：

  DOI：

文献信息

• IDO INHIBITORS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20160289171A1

  公开（公告）日：2016-10-06

  There are disclosed compounds that modulate or inhibit the enzymatic activity of indoleamine 2,3-dioxygenase (IDO), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders, such as cancer, viral infections and/or inflammatory disorders utilizing the compounds of the invention.

  已披露的化合物可调节或抑制吲哌酮胺2,3-二氧化酶（IDO）的酶活性，含有该化合物的药物组合物以及利用本发明的化合物治疗增殖性疾病，如癌症、病毒感染和/或炎症性疾病的方法。
• AZACYCLIC COMPOUNDS
  申请人：ACADIA Pharmaceuticals Inc.

  公开号：US20150259291A1

  公开（公告）日：2015-09-17

  Compounds and methods are provided for the treatment of disease conditions in which modification of serotonergic receptor activity has a beneficial effect. In the method, an effective amount of a compound is adminstered to a patient in need of such treatment.

  提供用于治疗修改血清素能受体活性具有有益效果的疾病状态的化合物和方法。在方法中，将有效量的化合物施用于需要此类治疗的病人。
• [EN] COMPOUNDS, SALTS THEREOF AND METHODS FOR TREATMENT OF DISEASES<br/>[FR] COMPOSÉS, SELS CORRESPONDANTS ET MÉTHODES POUR LE TRAITEMENT DE MALADIES
  申请人：ACADIA PHARM INC

  公开号：WO2019040107A1

  公开（公告）日：2019-02-28

  The present disclosure relates to compounds according to Formula (I), useful for treating diseases.

  本公开涉及按照式（I）的化合物，用于治疗疾病。
• [EN] HYDROXAMIC ACID DERIVATIVES HAVING ANTI-INFLAMMATORY ACTION<br/>[FR] DERIVES D'ACIDE HYDROXAMIQUE PRESENTANT UNE ACTION ANTI-INFLAMMATOIRE
  申请人：ITALFARMACO SPA

  公开号：WO2004063146A1

  公开（公告）日：2004-07-29

  Compounds of formula (I) are described: The compounds (I) inhibit TNFα production and may therefore be useful in the treatment of inflammation, of auto-immune diseases, and of pathological conditions which involve excessive production of that cytokine. The compounds (I) are also inhibitors of the histone deacetylase enzyme and may therefore be useful in tumorous diseases, alone or in association with other anti-tumour active ingredients.

  化合物的化学式（I）如下所述：这些化合物（I）抑制TNFα的产生，因此可能在治疗炎症、自身免疫疾病以及涉及过度产生该细胞因子的病理条件方面有用。这些化合物（I）也是组蛋白去乙酰化酶的抑制剂，因此可能在肿瘤性疾病中有用，单独使用或与其他抗肿瘤活性成分联合使用。
• Solid-Phase Synthesis of Substituted 2,3-Diketopiperazines from Reduced Polyamides
  作者：Adel Nefzi、Marc A. Giulianotti、Richard A. Houghten

  DOI：10.1016/s0040-4020(00)00253-2

  日期：2000.5

  An efficient method for the solid phase synthesis of 1,6-disubstituted 2,3-diketopiperazine and 1,4,5-trisubstituted 2,3-diketopiperazine derivatives is described. The reduction of resin-bound acylated amino acids or resin-bound acylated dipeptides, followed by treatment with oxalyldiimidazole, affords the corresponding diketopiperazines in good yield and high purity. This is an example of a broader

  描述了固相合成1,6-二取代的2,3-二酮哌嗪和1,4,5-三取代的2,3-二酮哌嗪衍生物的有效方法。还原树脂结合的酰化氨基酸或树脂结合的酰化二肽，然后用草酰二咪唑处理，以良好的收率和高纯度提供了相应的二酮哌嗪。这是使用肽直接或间接作为起始原料进行单个杂环化合物固相合成的广泛方法的一个例子。

表征谱图