3,4-二乙酰氧基苯甲醛 | 67727-64-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: 3,4-二乙酰氧基苯甲醛
• 英文名称: 3,4-diacetoxybenzaldehyde
• 英文别名: (2-acetyloxy-4-formylphenyl) acetate
• CAS: 67727-64-4
• 化学式: C₁₁H₁₀O₅
• mdl: MFCD00143057
• 分子量: 222.197
• InChiKey: WYHMNJKAVNPOOR-UHFFFAOYSA-N

物化性质

• 熔点：
  53 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2918300090
• 储存条件：
  存储在惰性气体中，并保持室温环境。

SDS

3,4-Diacetoxybenzaldehyde
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 3,4-Diacetoxybenzaldehyde

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Wash hands thoroughly after handling.
[Prevention]
Wear protective gloves/eye protection/face protection.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
[Response]
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 3,4-Diacetoxybenzaldehyde
Percent: >98.0%(GC)
CAS Number: 67727-64-4
Chemical Formula: C11H10O5

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
3,4-Diacetoxybenzaldehyde

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Section 4. FIRST AID MEASURES
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Safety glasses. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Crystal- Powder
Form:
Colour: White - Pale yellow
No data available
Odour:
pH: No data available
Melting point/freezing point:53°C
3,4-Diacetoxybenzaldehyde

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
No data available
[Other solvents]

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide
products:

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Section 11. TOXICOLOGICAL INFORMATION
No data available
Acute Toxicity:
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
No data available
IARC =
NTP = No data available
No data available
Reproductive toxicity:

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed
3,4-Diacetoxybenzaldehyde

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3,4-二乙酰氧基苯甲醛 在 盐酸 、 氢氧化钾 、 18-冠醚-6 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 3-(3,4-二羟基苯基)丙-2-烯醛
  参考文献：
  名称：

  咖啡酰和 5-OH 松柏醛和醇的化学合成以及双子叶植物和单子叶植物中木质素 O-甲基转移酶活性的测定

  摘要：

  为了研究单木质素生物合成途径中 O-甲基转移酶的底物偏好，通过涉及 Wittig 反应与相应羟基苯甲醛的新程序合成了咖啡酰和 5-羟基松柏醛。同样的程序也可用于合成咖啡醇和 5-羟基松柏醇。使用来自苜蓿 (Medicago sativa) 的粗提取物和重组咖啡酸 O-甲基转移酶以及来自模型豆科植物苜蓿、烟草、小麦和高羊茅的粗提取物测定针对这些底物的相对 O-甲基转移酶活性。所有这些物种的提取物比相应的羟基肉桂酸更有效地催化各种单木质醇醛和醇的甲基化。

  DOI：

  10.1016/s0031-9422(01)00391-0
• 作为产物：
  描述：

  胡椒醛 在 4-二甲氨基吡啶 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 3,4-二乙酰氧基苯甲醛
  参考文献：
  名称：

  PRELIMINARY ANTIPROLIFERATIVE EVALUATION OF NATURAL,-SYNTHETIC BENZALDEHYDES AND BENZYL ALCOHOLS

  摘要：

  Vanillin, o-vanillin, natural and synthetic benzaldehydes and benzyl alcohols were assessed for antiproliferative effects using different human cell lines. Benzyl alcohols were synthesized from benzaldehydes reduced with NaBH4 in methanol solution. A new method for deprotection of ether compounds with TiCl4 solution was achieved with better performance, than previously reported. Twenty four compounds were tested. The in vitro growth inhibition assay was based on sulphorhodamine dye to quantify cell viability. Catechol 9 derived from piperonal as well as compounds 4 and 12 showed higher cytotoxicity on breast and prostate cancer cell lines (MDA-MB-231 and PC-3 respectively). o-Vanillin 5 has the highest cytotoxicity for all cell lines. IC50 values of 35.40 +/- 4.2 mu M Breast MDA-MB231; 47.10 +/- 3.8 mu M Prostate PC-3; 72.50 + 5.4 mu M Prostate DU-145; 85.10 +/- 6.5 mu M and Colon HT-29, were obtained without toxicity towards dermal human fibroblast (DHF cells).

  DOI：

  10.4067/s0717-97072013000300003

文献信息

• A metal-free heterogeneous photocatalyst for the selective oxidative cleavage of CC bonds in aryl olefins <i>via</i> harvesting direct solar energy
  作者：Yu Zhang、Nareh Hatami、Niklas Simon Lange、Emanuel Ronge、Waldemar Schilling、Christian Jooss、Shoubhik Das

  DOI：10.1039/d0gc01187h

  日期：——

  transition metal-free) to avoid further leaching in the final products. This is for sure a big challenge to an organic chemist and to the pharmaceutical industries! To make this feasible, a mild and efficient protocol has been developed using polymeric carbon nitrides (PCN) as metal-free heterogeneous photocatalysts to convert various olefins into the corresponding carbonyls. Later, this catalyst has been

  C C键的选择性裂解对于合成含羰基的精细化学品和药物非常重要。新型方法，例如臭氧分解反应，Lemieux-Johnson氧化反应等。已经存在。与此平行，还发现了使用均相催化剂的催化方法。考虑到非均相催化剂的各种优点，例如可循环性和稳定性，已将几种基于过渡金属的非均相催化剂用于该反应。但是，制药行业更喜欢使用不含金属的催化剂（尤其是不含过渡金属的催化剂），以避免最终产品中进一步浸出。对于有机化学家和制药行业来说，这无疑是一个巨大的挑战！为了使之可行，已经开发了一种温和而有效的方案，使用聚合碳氮化物（PCN）作为无金属的非均相光催化剂，将各种烯烃转化为相应的羰基。后来，该催化剂已被用于使用直接太阳能的克级合成药物中。详细的机械研究揭示了氧气，催化剂和光源的实际作用。
• CAJANINE STRUCTURE ANALOGOUS COMPOUND, PREPARATION METHOD AND USE
  申请人：INSTITUTE OF MEDICINAL BIOTECHNOLOGY. CHINESE ACADEMY OF MEDICAL SCIENCES

  公开号：US20140371232A1

  公开（公告）日：2014-12-18

  Provided are cajanine structure analogous compounds, synthesis method and pharmacological effects thereof, the compounds of the present invention having the structure as represented by general formulas I, II, III, IV and V. Also provided are pharmaceutical compositions containing the compounds as active ingredient, and uses thereof; the compounds of the present invention having the pharmacological activities such as anti-virus, anti-virus-infection, nerve protection, anti-metabolic-diseases and the like. Also provided is a chemical total synthesis preparation method of the natural products cajanine, cajanine A and cajanine C. The present invention lays a foundation for the in-depth study and development of the compounds as clinical drugs in the future.

  提供的是与咖啡碱结构类似的化合物、合成方法及其药理效果，本发明的化合物具有如公式I、II、III、IV和V所代表的结构。还提供了含有这些化合物的药物组合物，以及它们的使用方法；本发明的化合物具有诸如抗病毒、抗病毒感染、神经保护、抗代谢性疾病等药理活性。还提供了天然产物咖啡碱、咖啡碱A和咖啡碱C的化学全合成制备方法。本发明为这些化合物作为未来临床药物深入研究和发展奠定了基础。
• CSJ acting as a versatile highly efficient greener resource for organic transformations
  作者：Himadri Sekhar Maity、Kaushik Misra、Tanushree Mahata、Ahindra Nag

  DOI：10.1039/c6ra01760f

  日期：——

  existing protocols have been developed for the reduction of aromatic aldehydes to their corresponding alcohols, decarboxylation of substituted benzoic acids (C6–C1) and substituted cinnamic acids (C6–C3) with a hydroxyl group at the para position with respect to the acid group to corresponding phenolic compounds and vinyl phenols respectively by using a natural feedstock, cucumber juice (CSJ), which

  已开发出一种简单，新颖，绿色且有效的替代方案，用于将芳族醛还原为相应的醇，将取代的苯甲酸（C 6 -C 1）和取代的肉桂酸（C 6 -C 3）脱羧。通过使用天然原料黄瓜汁（CSJ）（相对绿色的溶剂系统），在相对于酸的对位的羟基上分别形成相应的酚类化合物和乙烯基苯酚，进行底物选择性反应。另外，已经进行了芳族化合物的乙酰基以及苯甲酰基的水解，以通过CSJ提供优异的产率。
• Application of bioorthogonal hetero-Diels–Alder cycloaddition of 5-arylidene derivatives of 1,3-dimethylbarbituric acid and vinyl thioether for imaging inside living cells
  作者：Bartłomiej Bazan、Aleksandra Pałasz、Łukasz Skalniak、Dariusz Cież、Szymon Buda、Katarzyna Jędrzejowska、Sonia Głomb、Daniel Kamzol、Kinga Czarnota、Krystian Latos、Krzysztof Kozieł、Bogdan Musielak

  DOI：10.1039/d1ob00697e

  日期：——

  New bioorthogonal cycloaddition of 5-arylidene derivatives of 1,3-dimethylbarbituric acid as 1-oxa-1,3-butadienes and vinyl thioether as a dienophile has been applied to imaging inside living cells. The reaction is high yielding, selective, and fast in aqueous media. The proposed 1-oxa-1,3-butadiene derivative conjugated to a FITC fluorochrome selectively and rapidly labels the cancer cells pretreated

  1,3-二甲基巴比妥酸的 5-亚芳基衍生物作为 1-氧杂-1,3-丁二烯和乙烯基硫醚作为亲二烯体的新生物正交环加成已应用于活细胞内成像。该反应在水介质中产率高、选择性强且快速。所提出的 1-oxa-1,3-丁二烯衍生物与 FITC 荧光染料缀合，可选择性地快速标记用亲二烯体紫杉醇预处理的癌细胞。各种提出的生物正交环加成的二阶速率常数k 2估计在 0.9 × 10 -2 M -1 s -1到 1.4 M -1 s -1的范围内，这比第一代 TQ 连接（邻喹啉酮醌甲基化物和乙烯基硫醚连接， k 2 = 1.5 × 10 −3 M −1 s −1 ）与第二代 TQ 连接相当或更好（ k 2 = 2.8 × 10 -2 M -1 s -1 )。所提出的连接反应的反应速率常数k 2在四嗪和降冰片烯或四嗪和环丙烯的速率常数k 2的范围内。 这些发现表明该化学物质适用于体外成像实验。
• Site-Selective C–H Benzylation of Alkanes with N-Triftosylhydrazones Leading to Alkyl Aromatics
  作者：Zhaohong Liu、Shanshan Cao、Weijie Yu、Jiayi Wu、Fanhua Yi、Edward A. Anderson、Xihe Bi

  DOI：10.1016/j.chempr.2020.06.031

  日期：2020.8

  an abundant and valuable resource for transformation into value-added fine chemicals. However, selective functionalization of specific C(sp3)–H bonds in alkanes for alkyl-alkyl bond formation is a significant challenge because of their intrinsic inertness and the small differences in reactivity among various C(sp3)–H bonds. Here, we report a silver-catalyzed site-selective C(sp3)–H benzylation of simple

  烷烃是转化为高附加值精细化学品的宝贵资源。但是，由于烷烃固有的惰性以及各种C（sp 3）-H键之间的反应性差异小，因此烷烃中特定的C（sp 3）-H键选择性官能化以形成烷基-烷基键是一项重大挑战。在这里，我们报告使用N的简单烷烃的银催化位点选择性C（sp 3）–H苄基化-triftosylhydrazones作为方便的卡宾前体，可以合成高附加值的烷基化芳烃。还实现了从醛开始的一锅两步方案，从而构成了烷烃对芳基醛的正式还原烷基化。实验研究和DFT计算表明[Tp Br3 Ag] 2催化剂的作用是3倍：它调节卡宾反应性，抑制卡宾二聚作用，并避免产物过度插入。所有这三个方面对于将供体卡宾首次分子间分子插入简单烷烃的C（sp 3）-H键的成功至关重要。