2,3-二溴-4-羟基-5-甲氧基苯甲醛 | 2973-75-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2,3-二溴-4-羟基-5-甲氧基苯甲醛
• 英文名称: 5,6-dibromovanillin
• 英文别名: 2,3-dibromo-4-hydroxy-5-methoxybenzaldehyde
• CAS: 2973-75-3
• 化学式: C₈H₆Br₂O₃
• mdl: MFCD00016978
• 分子量: 309.942
• InChiKey: WKLKGSHBXNPUDU-UHFFFAOYSA-N

物化性质

• 熔点：
  212-215 °C
• 密度：
  1.9544 (rough estimate)
• 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)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

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
• 海关编码：
  2913000090
• 储存条件：
  存储于阴凉干燥处

SDS

Name:	2 3-Dibromo-4-hydroxy-5-methoxybenzaldehyde Material Safety Data Sheet
Synonym:
CAS:	2973-75-3

Section 1 - Chemical Product MSDS Name:2 3-Dibromo-4-hydroxy-5-methoxybenzaldehyde Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2973-75-3	2,3-Dibromo-4-hydroxy-5-methoxybenzald		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.Air sensitive.
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:

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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. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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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# 2973-75-3: 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: Powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 212 - 215 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: C8H6Br2O3
Molecular Weight: 309.94

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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.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, hydrogen bromide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2973-75-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,3-Dibromo-4-hydroxy-5-methoxybenzaldehyde - 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# 2973-75-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 2973-75-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2973-75-3 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：

  2,3-二溴-4-羟基-5-甲氧基苯甲醛 以79%的产率得到2,3-dibromo-4,5-dimethoxybenzaldehyde
  参考文献：
  名称：

  Cephem compounds, and antibacterial agents

  摘要：

  本发明揭示了由公式[I]表示的新型头孢菌素化合物及其药理学上可接受的盐或可在生理上水解的无毒酯类。其中，R1表示直链或支链低碳基，可以被保护的羧基取代，三苯甲基基团，氢原子或氟代低碳基；R2表示氢原子，金属原子，羧基保护基或可在体内产生水解酯残基的酯残基；R3、R4、R5和R6可以相同也可以不同，表示氢原子，卤素原子，直链或支链低碳基，可以被取代的巯基，可以被取代的低碳基氨基，可以被保护的羟基，低碳基氧基，低碳基酰基，低碳基氧羰基，或者可以被取代的低碳基亚甲二氧基基团，可以与R3和R4形成；R7表示氢原子，氰基，卤素原子或COOR8（R8为氢或低碳基）；R9表示可以被保护的氨基；Z表示N或CH；n表示0或1。本发明还声明了它们的制备过程以及含有它们作为有效成分的抗菌剂。

  公开号：

  US05244892A1
• 作为产物：
  描述：

  5-溴香兰素 在 溴 、 铁粉 、 溶剂黄146 作用下， 反应 12.0h， 生成 2,3-二溴-4-羟基-5-甲氧基苯甲醛
  参考文献：
  名称：

  发现新型溴酚-硫代氨基脲杂化物作为用于癌症的聚（ADP-核糖）聚合酶-1（PARP-1）的强效选择性抑制剂。

  摘要：

  聚（ADP-核糖）聚合酶-1（PARP-1）是抗癌药物发现的新潜在目标。设计，合成并评估了一系列作为PARP-1抑制剂的溴酚-硫代半碳杂zone杂化物的抗肿瘤活性。其中，最有前途的化合物11对PARP-2（IC50> 1000 nM）表现出优异的选择性PARP-1抑制活性（IC50 = 29.5 nM），并对SK-OV-3，Bel-7402和在体内SK-OV-3细胞异种移植模型中，HepG2癌细胞系（IC50 = 2.39、5.45和4.60μM）以及肿瘤生长的抑制作用。进一步的研究表明，化合物11通过多种抗癌机制发挥了抗肿瘤作用，包括诱导凋亡和细胞周期停滞，DNA双链断裂的细胞蓄积，DNA修复改变，抑制H2O2触发的PARylation，通过产生细胞毒性活性氧而产生的抗增殖作用以及自噬。另外，化合物11显示出良好的药代动力学特性和良好的安全性。这些观察表明，化合物11可以用作发现新的抗癌药物的先导化合物。

  DOI：

  10.1021/acs.jmedchem.8b01946

文献信息

• NOVEL CURCUMIN DERIVATIVE
  申请人：Sugimoto Hachiro

  公开号：US20110082295A1

  公开（公告）日：2011-04-07

  To develop a highly safe measure to treat Alzheimer's disease using a secretase-inhibiting substance, there is provided a compound represented by the following general formula (I) or a salt thereof: wherein A represents a phenyl group or the like, R 1 represents a chlorine atom, a bromine atom, or a nitro group or the like, R 2 , R 3 , R 4 , and R 5 each represent a hydrogen atom or the like, and L represents CH 2 —CH 2 or CH═CH.

  为了开发一种高度安全的措施来治疗阿尔茨海默病，提供了一种由以下一般式（I）或其盐表示的化合物： 其中A代表苯基或类似物，R1代表氯原子、溴原子或硝基团等，R2、R3、R4和R5各自代表氢原子或类似物，L代表CH2—CH2或CH═CH。
• Direct Access to Monoprotected Homoallylic 1,2-Diols via Dual Chromium/Photoredox Catalysis
  作者：Felix Schäfers、Linda Quach、J. Luca Schwarz、Mar Saladrigas、Constantin G. Daniliuc、Frank Glorius

  DOI：10.1021/acscatal.0c03697

  日期：2020.10.16

  Herein, we present a dual catalytic strategy to efficiently obtain monoprotected homoallylic 1,2-diols by coupling abundant aldehydes with simple (silyl) enol ethers, thus providing direct access to this important motif without the (super) stoichiometric use of prefunctionalized metal-allyl species. The modularity of our approach is shown by the introduction of several silyl- and alkyl-based protecting

  在这里，我们提出了一种双重催化策略，通过将丰富的醛与简单的（甲硅烷基）烯醇醚偶联，有效地获得单保护的均一的1,2-二醇，从而无需使用（超）化学计量的预官能化金属烯丙基即可直接获得这一重要基序。种类。通过引入几个基于甲硅烷基和烷基的保护基，可以看出我们方法的模块化。为了突出官能团的耐受性和化学选择性，我们证明了即使在存在酮和酯的情况下，各种脂族和（杂）芳族醛的功能化。机理研究支持自由基机理，从烯醇醚的单电子氧化开始。
• 溴酚-噁唑类化合物及其在治疗2型糖尿病药物中的应用
  申请人：中国科学院海洋研究所

  公开号：CN106588806A

  公开（公告）日：2017-04-26

  本发明涉及一类新型溴酚‑噁唑类PTP1B的化学全合成方法以及其在治疗2型糖尿病药物中的应用，所述PTP1B抑制剂结构式如下：该类化合物通过抑制蛋白酪氨酸磷脂酶1B的活性，增强胰岛素受体敏感性，对胰岛素抵抗类2型糖尿病具有良好的治疗作用。
• Decarboxylative C_sp3–C_sp3 coupling for benzylation of unstable ketone enolates: synthesis of p-(acylethyl)phenols
  作者：Sasa Wang、Xinzheng Chen、Qiaoqiao Ao、Huifei Wang、Hongbin Zhai

  DOI：10.1039/c6cc03835b

  日期：——

  A new decarboxylative Csp3-Csp3 coupling approach for the benzylation of ketone enolates has been developed. A variety of raspberry ketone derivatives were conveniently synthesized in good to excellent yields under...

  已经开发出一种新的用于羧甲基化烯醇烯酸酯的脱羧Csp3-Csp3偶联方法。在高温条件下，可以方便地合成多种树莓酮衍生物，并具有良好的产率。
• 溴酚-吡唑啉类化合物及其合成方法和应用
  申请人：山东大学

  公开号：CN111848516B

  公开（公告）日：2022-04-01

  本发明涉及一种化合物，尤其是一种溴酚‑吡唑啉类化合物及其合成方法和应用。一种溴酚‑吡唑啉类化合物，具有如下结构通式：本发明提供的溴酚‑吡唑啉化合物，具有高效的主蛋白酶Mpro抑制活性，能够在细胞中干扰冠状病毒的复制，提示该化合物具有治疗冠状病毒肺炎的功效，在制备治疗冠状病毒肺炎的药物中具有广阔的应用前景。

表征谱图