3-乙炔基苯甲醚 | 768-70-7

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-乙炔基苯甲醚
• 中文别名: 1-乙炔-3-甲氧基苯
• 英文名称: 1-ethynyl-3-methoxybenzene
• 英文别名: 3-ethynylanisole；(3-methoxy-phenyl)-acetylene；m-methoxyphenylacetylene；1-ethynyl-3-methoxylbenzene；3-ethynyl-1-methoxybenzene；meta-methoxyphenyl acetylene
• CAS: 768-70-7
• 化学式: C₉H₈O
• 分子量: 132.162
• InChiKey: ZASXCTCNZKFDTP-UHFFFAOYSA-N

物化性质

• 沸点：
  204-210 °C (lit.)
• 密度：
  1.04 g/mL at 25 °C (lit.)
• 闪点：
  170 °F
• 稳定性/保质期：

  在常温常压下，该物质是稳定的。

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2909309090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  常温、避光、存于通风干燥处。

SDS

---

Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product name : 3-Ethynylanisole

---

Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a dangerous substance according to GHS.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
This substance is not classified as dangerous according to Directive 67/548/EEC.
Other hazards
Stench.

---

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Synonyms : 1-Ethynyl-3-methoxybenzene
Formula : C9H8O
Molecular Weight : 132,16 g/mol
CAS-No. EC-No. Index-No. Classification Concentration
1-Ethynyl-3-methoxybenzene
768-70-7 - - - -

---

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
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Do NOT induce vomiting. Never give anything by mouth to an unconscious person. Rinse mouth with water.
Consult a physician.

---

Section 5. FIRE-FIGHTING MEASURES
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 protective equipment for fire-fighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
Use water spray to cool unopened containers.

---

Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions
Avoid breathing vapors, mist or gas. Remove all sources of ignition. 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). Keep in suitable, closed containers
for disposal.

---

Section 7. HANDLING AND STORAGE
Precautions for safe handling
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
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.
Stench.

---

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
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested and
approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin and body protection
impervious clothing, 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.

---

Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Appearance
Form liquid
Colour colourless
Odour Stench.
Safety data
pH no data available
Melting point no data available
Boiling point 204 - 210 °C - lit.
Flash point 76,67 °C - closed cup
Ignition temperature no data available
Lower explosion limit no data available
Upper explosion limit no data available
Density 1,04 g/cm3 at 25 °C
Water solubility no data available

---

Section 10. STABILITY AND REACTIVITY
Chemical stability
Stable under recommended storage conditions.
Conditions to avoid
Heat, flames and sparks.
Materials to avoid
Strong oxidizing agentsStrong oxidizing agents, acids, Halogens, Alkali metals
Hazardous decomposition products
Hazardous decomposition products formed under fire conditions. - Carbon oxides

---

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. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been thoroughly
investigated.
Additional Information
RTECS: Not available

---

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

---

Section 13. DISPOSAL CONSIDERATIONS
Product
This combustible material may be burned in a chemical incinerator equipped with an afterburner and
scrubber. 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.

---

Section 14. TRANSPORT INFORMATION
ADR/RID
Not dangerous goods
IMDG
Not dangerous goods
IATA
UN-Number: 3334 Class: 9
Proper shipping name: Aviation regulated liquid, n.o.s. (1-Ethynyl-3-methoxybenzene)

---

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

---

Section 16. OTHER INFORMATION
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.

制备方法与用途

用途

3-乙炔基苯甲醚是一种重要的醚类衍生物，可用作医药合成中间体。

制备

3-乙炔基苯甲醚的制备过程如下：

1. 将5 mL（39.5 mmol，1当量）3-溴茴香醚、22 mL（158 mmol，4当量）三乙胺、0.75 g（4.0 mmol，10 mol％）氯化亚铜加入到甲苯（50 mL）中，并滴加1.4 g（2.0 mmol，5 mol％）钯（PPb）2Cl2和6 mL（43.5 mmol，1.1当量）三甲基甲硅烷基乙炔。在80℃下搅拌反应混合物5小时后，用乙酸乙酯稀释，并用水（3×50 mL）洗涤。有机相经硫酸镁干燥，在减压下浓缩。粗产物通过硅胶快速色谱纯化，使用正己烷/乙酸乙酯（10：1）作为洗脱剂，得到无色油状物。

2. 将步骤1中获得的化合物（6 g，29.6 mmol，1当量）溶解在40 mL甲醇中，并加入2 g（14.8 mmol，0.5当量）碳酸钾。在室温下搅拌4小时后，将混合物用乙醚稀释，并用水（3×50 mL）洗涤。有机相经硫酸镁干燥，在减压下浓缩。从浅黄色油状物中分离出的产物即为3-乙炔基苯甲醚。产率为90%。

反应信息

• 作为反应物：
  描述：

  3-乙炔基苯甲醚 在 盐酸 、 sodium hydroxide 、 三氯化铝 、 potassium tert-butylate 、 叔丁醇 、 苯 作用下， 生成 rac-17-((Z)-benzylidene)-3-methoxy-D-homo-9β-gona-1,3,5(10)-trien-17a-one
  参考文献：
  名称：

  The Total Synthesis of Estrone and Three Stereoisomers Including Lumiestrone

  摘要：

  DOI：

  10.1021/ja01131a037
• 作为产物：
  描述：

  间溴苯甲醚 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 34.0h， 生成 3-乙炔基苯甲醚
  参考文献：
  名称：

  高选择性且无添加剂的 Pd(OAc)2/CPP 催化炔烃的氢氨基羰基化

  摘要：

  在此，报道了使用 Pd 通过炔烃与各种胺底物（如芳香胺、脂肪胺、固体胺源如 NH 4 HCO 3 ，甚至强碱性哌啶）的氢氨基羰基化反应合成支链 α,β-不饱和酰胺。 (OAc) 2 /混合N-杂环卡宾-膦-膦( CPP )催化体系。该反应具有无添加剂、底物范围广、选择性高（b/l > 99 : 1）和优异的产率的特点。机理研究表明该反应是通过氢化钯途径发生的。 CPP采用卡宾-膦配位模式的杂化二齿配体构象，其中一个磷原子保持外部可接近，可能在催化循环过程中充当稳定辅助剂。

  DOI：

  10.1039/d4ob00644e
• 作为试剂：
  描述：

  1,3-butadiynyl(tert-butyl)diphenylsilane 在 六甲基磷酰三胺 、 正丁基锂 、 四甲基乙二胺 、 3-乙炔基苯甲醚 、 氧气 、 copper(l) chloride 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 1-(t-butyldiphenylsilyl)-8-trimethylsilyl-1,3,5,7-octatetrayne
  参考文献：
  名称：

  Synthesis and Reactions of Monosilylated 1,3,5-Hexatriyne and 1,3,5,7-Octatetrayne. Total Synthesis of Caryoynencins

  摘要：

  5-hexatriyne 与石碳酸苯乙炔的反应分别产生了不稳定的 1-(t-丁基二苯基硅烷基)-1,3,5,7-辛四炔和 1-(t-丁基二苯基硅烷基)-1,3,5-hexatriyne。在石化过程中，末端乙炔与醛类和酮类发生反应，产生多炔醇，产量很高。该反应被应用于合成多炔抗生素--卡里诺霉素。在掺杂了 SO3 的 ITO 涂层玻璃板上聚合末端的辛四炔，可得到一层薄膜，其导电率为 10-4 S cm-1。

  DOI：

  10.1246/bcsj.67.1717

文献信息

• BENZOTHIOPHENE INHIBITORS OF RHO KINASE
  申请人：Kahraman Mehmet

  公开号：US20080021026A1

  公开（公告）日：2008-01-24

  The present invention relates to compounds and methods which may be useful as inhibitors of Rho kinase for the treatment or prevention of disease.

  本发明涉及化合物和方法，这些化合物和方法可能作为Rho激酶的抑制剂在治疗或预防疾病方面有用。
• Synthesis of Multifunctionalized 2-Carbonylpyrrole by Rhodium-Catalyzed Transannulation of 1-Sulfonyl-1,2,3-triazole with β-Diketone
  作者：Wanli Cheng、Yanhua Tang、Ze-Feng Xu、Chuan-Ying Li

  DOI：10.1021/acs.orglett.6b03179

  日期：2016.12.2

  A facile rhodium-catalyzed transannulation of 1-sulfonyl-1,2,3-triazoles with β-diketones was realized, and a series of multisubstituted 2-carbonylpyrroles were synthesized efficiently (up to 94% yield). The protocol features several advantages, such as readily available materials, mild reaction conditions, a concise operating procedure, a broad reaction scope, and excellent regioselectivity when benzoylacetone

  实现了便捷的铑催化的1-磺酰基-1,2,3-三唑与β-二酮的铑过度环氧化反应，并有效地合成了一系列多取代的2-羰基吡咯（产率高达94％）。该方案具有几个优点，例如易于获得的材料，温和的反应条件，简洁的操作程序，广泛的反应范围以及使用苯甲酰丙酮衍生物时的优异的区域选择性。
• Rhodium-Catalyzed Denitrogenative Transannulation of <i>N</i>-Sulfonyl-1,2,3-triazoles with Glycals Giving Pyrroline-Fused <i>N</i>-Glycosides
  作者：Jingjing Bi、Qiang Tan、Hao Wu、Qingfeng Liu、Guisheng Zhang

  DOI：10.1021/acs.orglett.1c02141

  日期：2021.8.20

  with exclusive regioselectivity and stereoselectivity. Functional application of such a resultant product by oxidative addition and epoxidation is also explored. Notably, the treatment of a pyrroline-fused N-glycoside (3a) with TMSOTf efficiently leads to an interesting unexpected C-nucleoside (9) via a TMSOTf-inducing ring opening/acetyl migration/ring closing reaction sequence.

  这里描述的是通过铑催化的N-磺酰基-1,2,3-三唑与聚糖的脱氮环化反应选择性合成 2,3-二氢吡咯稠合的N-糖苷。一系列吡咯啉稠合的N-糖苷以中等至极好的收率提供，具有独特的区域选择性和立体选择性。还探索了这种通过氧化加成和环氧化得到的产物的功能应用。值得注意的是，通过 TMSOTf 诱导的开环/乙酰基迁移/闭环反应序列，用 TMSOTf处理吡咯啉稠合的N-糖苷（3a）有效地导致有趣的意外C-核苷（9）。
• 신규한 셀레늄 고리 화합물 및 이의 제조방법
  申请人：KNU-Industry Cooperation Foundation 강원대학교산학협력단(220040088571) BRN ▼221-82-10213

  公开号：KR102037409B1

  公开（公告）日：2019-10-28

  2개 이상의 질소와 셀레늄이 고리 원소를 이루는 방향족 고리 화합물인 반응물질 1과, 적어도 이중 결합 이상의 결합을 갖는 반응물질 2를 로듐 촉매 반응 하에 반응시키는 단계; 및 상기 반응에 따라 상기 2개 이상의 질소위치에 상기 이중 결합 이상의 결합을 갖는 원소가 고리 원소로 첨가되어 셀레늄 고리 화합물이 합성되는 단계를 포함하며, 상기 반응물질 1 이고, 상기 반응물질 2는 알카인, 알켄, 나이트릴, 다이엔 결합 중 어느 하나를 포함하는 화합물인 것을 특징으로 하는 셀레늄 고리 화합물 합성 방법이 제공된다. (상기 R1, R2는 각각 수소, 할로겐기, 탄소수 1 내지 10의 알킬기, 탄소수 1 내지 10의 알케닐기, 탄소수 1 내지 10의 알키닐기, 탄소수 6 내지 12의 치환되거나 치환되지 않은 아릴기, 치환되거나 치환되지 않은 탄소수 5 내지 12의 헤테로아릴기 및 탄소수 1 내지 10의 알킬옥시로 이루어진 군으로부터 선택된 어느 하나이며, 상기 R1과 R2는 서로 연결되어 융합고리를 형성될 수 있음)

  2个以上的氮和硒形成环元素的芳香环化合物的反应物质1，至少具有双键以上的键合的反应物质2在铑催化反应下反应的步骤；以及根据所述反应，在所述2个以上的氮位置上，具有双键以上的键合的元素被添加为环元素以合成硒环化合物的步骤，其中所述反应物质1，并且所述反应物质2是包含碱金属，烯烃，腈，二烯键中的任何一种的化合物的硒环化合物合成方法，其特征在于提供。 （其中R1，R2分别为氢，卤素，1到10个碳原子的烷基，1到10个碳原子的烯基，1到10个碳原子的烷基，6到12个被取代或未被取代的芳基，5到12个被取代或未被取代的杂环芳基和1到10个烷氧基中的任何一个，其中R1和R2可以相互连接以形成融合环）
• An Efficient One-Pot Protocol for the Synthesis of Polysubstituted 4-Amino-iminocoumarins and 4-Aminoquinolines by a Copper-Catalyzed Three-Component Reaction
  作者：Fengping Yi、Songxing Zhang、Ying Huang、Lirong Zhang、Weiyin Yi

  DOI：10.1002/ejoc.201601217

  日期：2017.1.3

  A simple and efficient one‐pot approach is reported for the synthesis of highly functionalized 4‐amino‐iminocoumarins and 4‐aminoquinolines in moderate to excellent yields. The copper‐catalyzed reaction uses terminal alkynes, sulfonyl azides, and either 2‐hydroxybenzonitriles or 2‐aminobenzonitrile as substrates.

  据报道，一种简单有效的单罐方法可以中等至极好的收率合成高度官能化的4-氨基亚氨基香豆素和4-氨基喹啉。铜催化的反应使用末端炔烃，磺酰叠氮化物和2-羟基苄腈或2-氨基苄腈作为底物。

表征谱图