3',4'-dimethoxyacetophenone oxime | 88920-78-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3',4'-dimethoxyacetophenone oxime
• 英文别名: 1-(3,4-dimethoxyphenyl)ethan-1-one oxime；N-[1-(3,4-dimethoxyphenyl)ethylidene]hydroxylamine
• CAS: 88920-78-9
• 化学式: C₁₀H₁₃NO₃
• mdl: MFCD00085021
• 分子量: 195.218
• InChiKey: ILXJZPXGWURHNZ-UHFFFAOYSA-N

物化性质

• 熔点：
  147 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 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：
  51
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38

SDS

Name:	1-(3 4-Dimethoxyphenyl)ethan-1-one oxime 97% Material Safety Data Sheet
Synonym:	3,4-Dimethoxyacetophenone oxim
CAS:	88920-78-9

Section 1 - Chemical Product MSDS Name:1-(3 4-Dimethoxyphenyl)ethan-1-one oxime 97% Material Safety Data Sheet
Synonym:3,4-Dimethoxyacetophenone oxim

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
88920-78-9	1-(3,4-Dimethoxyphenyl)ethan-1-one oxi	97%	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.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. 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.
Notes to Physician:
Treat symptomatically and supportively.

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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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Keep refrigerated. (Store below 4C/39F.) Store in a tightly closed container. Store in a dry area.

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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# 88920-78-9: Personal Protective Equipment Eyes: Not available.
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: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 147 - 150 deg C
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: C10H13NO3
Molecular Weight: 195

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, reducing agents, bases, acid chlorides.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 88920-78-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-(3,4-Dimethoxyphenyl)ethan-1-one oxime - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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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# 88920-78-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 88920-78-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 88920-78-9 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

反应信息

• 作为反应物：
  描述：

  3',4'-dimethoxyacetophenone oxime 在 Iron(III) nitrate nonahydrate 、 氧气 作用下， 以 甲苯 为溶剂， 37.0 ℃ 、101.33 kPa 条件下， 反应 1.5h， 以84%的产率得到3,4-二甲氧基苯乙酮
  参考文献：
  名称：

  Fe(NO₃)₃·9H₂O-catalyzed aerobic oxidative deoximation of ketoximes and aldoximes under mild conditions

  摘要：

  已开发出一种温和简单的过程，用于有效地氧化脱氧化一系列酮肟和醛肟，该过程利用Fe(NO₃)₃·9H₂O作为单一催化剂，分子氧作为绿色氧化剂。这种环保的方案提供了中等到优良的产率，具有广泛的官能团耐受性，是一种对实际应用有价值的合成方法。根据相关的验证实验，提出了一个合理的机制。

  DOI：

  10.1139/cjc-2017-0567
• 作为产物：
  描述：

  3,4-二甲氧基苯乙酮 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 生成 3',4'-dimethoxyacetophenone oxime
  参考文献：
  名称：

  由O-酰基肟无催化剂合成单和双取代的嘧啶

  摘要：

  O-酰基肟向各种N-杂环的过渡金属或碘催化的转化是公认的。在本文中，我们报道了一种无催化剂，基于肟羧酸盐的三组分缩合方法，可用于获得单取代和二取代的嘧啶。制备了各种取代的嘧啶，它们的产率中等至优异。对照实验表明，原位生成的甲am是关键中间体。

  DOI：

  10.1016/j.tetlet.2018.05.023

文献信息

• SO₂ F₂ -Activated Efficient Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams
  作者：Guofu Zhang、Yiyong Zhao、Lidi Xuan、Chengrong Ding

  DOI：10.1002/ejoc.201900844

  日期：2019.8.15

  A novel protocol for the efficient activation of the Beckmann rearrangement utilizing the readily available sulfuryl fluoride (SO2F2 gas) is reported. The substrate scope of this methodology has been demonstrated by 37 examples with good to nearly quantitative isolated yields in a short time. A tentative mechanism was proposed involving formation and elimination of sulfonyl ester.

  报道了一种利用容易获得的硫酰氟（SO 2 F 2气体）有效激活贝克曼重排的新方案。该方法的底物范围已通过37个实例证明，并在短时间内获得了良好至近乎定量的分离产率。提出了一种尝试性的机制，涉及形成和消除磺酰基酯。
• Synthesis of Air- and Moisture-Stable, Storable Chiral Oxorhenium Complexes and Their Application as Catalysts for the Enantioselective Imine Reduction
  作者：Braja Gopal Das、Rajender Nallagonda、Dhananjay Dey、Prasanta Ghorai

  DOI：10.1002/chem.201501914

  日期：2015.9.1

  salicyloxazoline based oxorhenium(V) complexes have been synthesized and their catalytic application for the asymmetric reduction of ketimines using hydrosilane as hydride source is disclosed. A broad substrate scope, high yields, and excellent enantioselectivities (up to 99 %) are attained. Furthermore, the syntheses of enantiopure α‐amino esters, γ‐ and δ‐lactams, and isoindolinones have also been carried

  合成了空气/水分稳定，晶体和可储存的手性水杨基恶唑啉基氧化（V）配合物，并公开了其在氢化硅烷作为氢化物源的情况下催化不对称还原酮亚胺的催化应用。获得了广泛的底物范围，高收率和出色的对映选择性（最高99％）。此外，对映体纯α-氨基酯，γ-和δ-内酰胺以及异吲哚啉酮的合成也已使用该方法进行。最后，该方法已应用于具有药物相关性的合成靶标，例如R -（+）-沙丁胺碱和R -（+）-crispine A.
• A rapid and convenient method for the synthesis of aldoximes under microwave irradiation using in situ generated ionic liquids
  作者：A.. R. Hajipour、F. Rafiee、A. E. Ruoho

  DOI：10.1007/bf03245867

  日期：2010.3

  We have developed a chemoselective, simple and efficient method for the preparation of aldoximes using microwave irradiation in the presence of tribenzylamine or 1,4-diazabicyclo[2.2.2]octane or 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane bromide as bases and useful precursors for in situ generation of ionic liquids.

  我们已经开发了一种化学选择性，简单而有效的方法，用于在三苄胺或1,4-二氮杂双环[2.2.2]辛烷或1-苄基-4-氮杂-1-氮杂双环[2.2]存在下使用微波辐射制备醛肟。 2]溴化辛烷作为碱和有用的前体，用于原位生成离子液体。
• CONVERSION OF OXIMES, PHENYLHYDRAZONES, 2,4-DINITROPHENYLHYDRAZONES, AND SEMICARBAZONES TO CORRESPONDING CARBONYL COMPOUNDS WITH BENZYLTRIPHENYLPHOSPHONIUM PEROXYMONOSULFATE (BnPh₃P⁺HSO₅⁻) (BTPPMS) IN THE PRESENCE OF BISMUTH CHLORIDE UNDER NON-AQUEOUS CONDITIONS
  作者：A. R. Hajipour、S. E. Mallakpour、I. M. Baltork、H. Adibi

  DOI：10.1081/scc-100106197

  日期：2001.1

  novel reagent for the conversion of oximes, phenylhydrazones, 2,4-dinitrophenylhydrazones and semicarbazones to the corresponding carbonyl compounds. The reaction has been performed in acetonitrile under reflux conditions in the presence of a catalytic amount of bismuth chloride.

  已发现苄基三苯基鏻过氧单硫酸盐 (BTPPMS) (1) 是一种有效的新型试剂，可用于将肟、苯腙、2,4-二硝基苯腙和缩氨基脲转化为相应的羰基化合物。该反应在乙腈中在回流条件下在催化量的氯化铋存在下进行。
• Synthesis of Chiral α-Amino Tertiary Boronic Esters by Enantioselective Hydroboration of α-Arylenamides
  作者：Naifu Hu、Guoqing Zhao、Yuanyuan Zhang、Xiangqian Liu、Guangyu Li、Wenjun Tang

  DOI：10.1021/jacs.5b03760

  日期：2015.6.3

  rhodium-catalyzed asymmetric hydroboration of α-arylenamides with BI-DIME as the chiral ligand and (Bpin)2 as the reagent yields for the first time a series of α-amino tertiary boronic esters in good yields and excellent enantioselectivities (up to 99% ee).

  以 BI-DIME 作为手性配体和 (Bpin)2 作为试剂的 α-芳基酰胺的铑催化不对称硼氢化反应首次以良好的收率和优异的对映选择性（高达 99 % ee）。