3-甲氧基苯基丙酮 | 3027-13-2

• 物质功能分类: 香精与香料 - 合成香料 - 酮类香料
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-甲氧基苯基丙酮
• 中文别名: 1-(3-甲氧基苯基)丙-2-酮；3-甲氧基苯丙酮
• 英文名称: 1-(3-methoxyphenyl)propan-2-one
• 英文别名: 3-methoxyphenylacetone；1-(3-methoxyphenyl)-2-propanone；1-(3-Methoxyphenyl)acetone
• CAS: 3027-13-2
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: RMMRRRLPDBJBQL-UHFFFAOYSA-N

物化性质

• 熔点：
  258 °C
• 沸点：
  258-260 °C (lit.)
• 密度：
  1.911 g/mL at 25 °C (lit.)
• 闪点：
  >230 °F
• 溶解度：
  与二甲基亚砜混溶。
• LogP：
  1.350 (est)
• 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)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• WGK Germany：
  3
• 海关编码：
  2914509090
• 安全说明：
  S24/25
• 危险性防范说明：
  P261,P301+P312,P302+P352,P304+P340,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存放在阴凉干燥处即可。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 3-Methoxyphenylacetone
CAS-No. : 3027-13-2
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
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C10H12O2
Molecular Weight : 164,2 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
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
Carbon oxides
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
Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
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
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.
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
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
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
impervious 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
Respiratory protection not required. For nuisance exposures use type OV/AG (US) or type ABEK
(EU EN 14387) respirator cartridges. 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
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 258 - 260 °C - lit.
boiling range
g) Flash point > 113,00 °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 1,911 g/cm3 at 25 °C
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
Strong 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 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.
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.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
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
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. 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. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

应用

3-甲氧基苯基丙酮可用于合成香料，并且也用于合成盐酸他喷他多。

制备

一种绿色合成3-甲氧基苯基丙酮的方法。为解决上述技术问题，本发明采用以下技术方案：在装有回流冷凝管和滴液漏斗的反应器中加入镁粉与无水三氯化铝。从滴液漏斗缓慢加入间甲氧基溴苯和四氢呋喃(THF)混合溶液，并控制反应液温度在30-80℃之间，使溶液保持微沸状态。滴加完毕后加热回流0.5-1.0小时，确保镁完全反应，生成格氏试剂。随后，在搅拌下将丙腈缓慢滴加至格氏试剂中，滴加完成后继续反应1.0-2.0小时。反应结束后，在冷水浴中缓慢滴加3mol/L的盐酸分解加成产物，分出无机相，有机相经常压蒸馏除去THF后进行减压蒸馏，最终得到3-甲氧基苯基丙酮。

反应信息

• 作为反应物：
  描述：

  3-甲氧基苯基丙酮 在 sodium hydroxide 、 sodium tetrahydroborate 、 正丁基锂 作用下， 以 苯 为溶剂， 反应 5.5h， 生成 mellein methyl ether
  参考文献：
  名称：

  Napolitano, Elio; Morsani, Massimo; Fiaschi, Rita, Gazzetta Chimica Italiana, 1991, vol. 121, # 5, p. 249 - 255

  摘要：

  DOI：
• 作为产物：
  描述：

  5-甲氧基-7-甲基二环[4.2.0]辛-1,3,5-三烯-7-醇 在 tris-(dibenzylideneacetone)dipalladium(0) 、 对苄基三氟甲磺酸 、 caesium carbonate 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 甲苯 为溶剂， 以82%的产率得到3-甲氧基苯基丙酮
  参考文献：
  名称：

  Palladium-Catalyzed Selective Carboelimination and Cross-Coupling Reactions of Benzocyclobutenols with Aryl Bromides

  摘要：

  The palladium-catalyzed selective beta-carboelimination and cross-coupling chemistry of benzocyclobutenols is described. In contrast to the base-mediated ring-opening reactions of benzocyclobutenols, this variant proceeds with exclusive cleavage of the proximal bond.

  DOI：

  10.1021/jo201632c

文献信息

• Enantioselective Direct α-Amination of Aldehydes via a Photoredox Mechanism: A Strategy for Asymmetric Amine Fragment Coupling
  作者：Giuseppe Cecere、Christian M. König、Jennifer L. Alleva、David W. C. MacMillan

  DOI：10.1021/ja406181e

  日期：2013.8.7

  The direct, asymmetric α-amination of aldehydes has been accomplished via a combination of photoredox and organocatalysis. Photon-generated N-centered radicals undergo enantioselective α-addition to catalytically formed chiral enamines to directly produce stable α-amino aldehyde adducts bearing synthetically useful amine substitution patterns. Incorporation of a photolabile group on the amine precursor

  醛的直接、不对称 α-胺化是通过光氧化还原和有机催化的组合完成的。光子生成的 N 中心自由基与催化形成的手性烯胺进行对映选择性 α-加成，直接产生具有合成有用胺取代模式的稳定 α-氨基醛加合物。在胺前体上引入光不稳定基团避免了在该转化中使用光氧化还原催化剂的需要。重要的是，这种光诱导转化允许直接和对映选择性地获得不需要反应后操作的 α-氨基醛产品。
• [EN] BI-1H-BENZIMIDAZOLES AS HEPATITIS C VIRUS INHIBITORS<br/>[FR] INHIBITEURS DU VIRUS DE L'HÉPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2010017401A1

  公开（公告）日：2010-02-11

  The present disclosure relates to compounds, compositions and methods for the treatment of Hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.

  本公开涉及化合物、组合物和治疗丙型肝炎病毒（HCV）感染的方法。还公开了含有这些化合物的药物组合物以及在治疗HCV感染中使用这些化合物的方法。
• [EN] NAPHT- 2 -YLACETIC ACID DERIVATIVES TO TREAT AIDS<br/>[FR] DÉRIVÉS D'ACIDE NAPHT-2-YLACÉTIQUE DANS LE TRAITEMENT DU SIDA
  申请人：GILEAD SCIENCES INC

  公开号：WO2012003497A1

  公开（公告）日：2012-01-05

  The invention provides compounds of formula (I): or a salt thereof as described herein. The invention also provides pharmaceutical compositions comprising a compound of formula I, processes for preparing compounds of formula (I), intermediates useful for preparing compounds of formula I and therapeutic methods for treating the proliferation of the HIV virus, treating AIDS or delaying the onset of AIDS or ARC symptoms in a mammal using compounds of formula (I).

  这项发明提供了如下式（I）的化合物或其盐。该发明还提供了包括如下式I的化合物的药物组合物，制备如下式（I）化合物的方法，用于制备如下式I化合物的有用中间体，以及使用如下式（I）化合物治疗HIV病毒的增殖、治疗艾滋病或延缓哺乳动物发生艾滋病或ARC症状的治疗方法。
• QUINOXALINE-BASED LXR MODULATORS
  申请人：Hu Baihua

  公开号：US20100120778A1

  公开（公告）日：2010-05-13

  Disclosed are quinoxaline-based modulators of Liver X receptors (LXRs) and related methods. The modulators include compounds of formula (I): wherein: each of L 1 and L 2 is, independently, a bond, —O— or —NH—; R 2 is C 6 -C 10 aryl or heteroaryl including 5-10 atoms, each of which is (i) substituted with 1 R 9 , and (ii) optionally further substituted with from 1-4 R e ; and each of R 4 and R 5 is, independently (i) hydrogen; or (ii) halo; or (iii) C 1 -C 6 alkyl or C 1 -C 6 haloalkyl, each of which is optionally substituted with from 1-3 R a ; and R 1 , R 3 , R 6 , R 9 , R a and R e are defined herein. In general, these compounds can be used for treating or preventing one or more diseases, disorders, conditions or symptoms mediated by LXRs.

  公开了基于喹诺克的Liver X受体（LXRs）调节剂及相关方法。这些调节剂包括以下式（I）的化合物： 其中： L1和L2分别独立为键，-O-或-NH-； R2是C6-C10的芳基或杂芳基，包括5-10个原子，每个原子（i）带有1个R9基团，和（ii）可选地带有1-4个Re基团； R4和R5分别独立为（i）氢；（ii）卤素；或（iii）C1-C6的烷基或C1-C6的卤代烷基，每个都可选地带有1-3个Ra基团； 以及R1、R3、R6、R9、Ra和Re都在此定义。 一般来说，这些化合物可用于治疗或预防一个或多个由LXRs介导的疾病、失调、状况或症状。
• Umpolung Difunctionalization of Carbonyls via Visible-Light Photoredox Catalytic Radical-Carbanion Relay
  作者：Shun Wang、Bei-Yi Cheng、Matea Sršen、Burkhard König

  DOI：10.1021/jacs.0c00629

  日期：2020.4.22

  catalysis with the Wolff–Kishner (WK) reaction allows the difunctionalization of carbonyl groups by a radical-carbanion relay sequence (photo-Wolff–Kishner reaction). Photoredox initiated radical addition to N-sulfonylhydrazones yields α-functionalized carbanions following the WK-type mechanism. With sulfur-centered radicals, the carbanions are further functionalized by reaction with electrophiles

  光氧化还原催化与沃尔夫-基什纳 (WK) 反应相结合，可以通过自由基-碳负离子中继序列（光沃尔夫-基什纳反应）对羰基进行双官能化。光氧化还原引发自由基加成至 N-磺酰腙，按照 WK 型机制产生 α-功能化碳负离子。对于以硫为中心的自由基，碳负离子通过与包括 CO2 和醛在内的亲电子试剂反应而进一步官能化，而 CF3 自由基加成则通过生成的 α-CF3 碳负离子的 β-氟化物消除提供了多种偕二氟烯烃。 80 多个底物示例证明了该反应序列的广泛适用性。包括自由基抑制、氘标记、荧光猝灭、循环伏安法和控制实验在内的一系列研究支持了所提出的自由基-碳负离子中继机制。

表征谱图