7-乙酰氧基-4-溴甲基香豆素 | 2747-04-8

• 物质功能分类: 医药中间体 - 吡喃类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 7-乙酰氧基-4-溴甲基香豆素
• 中文别名: 4-溴甲基-7-乙酸香豆素；7-乙酰氧基-4-溴甲基香豆素[用于高效液相色谱标记]
• 英文名称: 7-acetoxy-4-bromomethyl-2H-1-benzopyran-2-one
• 英文别名: 7-acetoxy-4-(bromomethyl)coumarin；7-acetoxy-4-bromomethylcoumarin；7-acetoxy-4-bromomethyl-chromen-2-one；7-acetoxy-4-bromomethyl-coumarin；7-Acetoxy-4-brommethyl-cumarin；4-Bromomethyl-7-acetoxycoumarin；[4-(bromomethyl)-2-oxochromen-7-yl] acetate
• CAS: 2747-04-8
• 化学式: C₁₂H₉BrO₄
• mdl: MFCD00010707
• 分子量: 297.105
• InChiKey: YDJFMNSSDOXBSR-UHFFFAOYSA-N

物化性质

• 熔点：
  180-182°C
• 沸点：
  414.4±45.0 °C(Predicted)
• 密度：
  1.589±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、乙酸乙酯
• 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)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  8
• 危险品标志：
  C
• 安全说明：
  S22,S26,S27,S36/37/39,S45
• 危险类别码：
  R34
• 危险品运输编号：
  1759
• 海关编码：
  2932209090
• 包装等级：
  III
• 危险类别：
  8
• 储存条件：
  存放于阴凉干燥处。

SDS

7-Acetoxy-4-bromomethylcoumarin [for HPLC Labeling] Revision number: 1
SAFETY DATA SHEET

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Section 1. BASE INFORMATION
Product name: 7-Acetoxy-4-bromomethylcoumarin [for HPLC Labeling]

Revision number: 1

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Section 2. HAZARDS IDENTIFICATION
Classification of the GHS
PHYSICAL HAZARDS
Corrosive to metals Category 1
HEALTH HAZARDS
Skin corrosion/irritation Category 1B
Category 1
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements
Pictograms or hazard symbols
Signal word Danger
Hazard statement May be corrosive to metals
Causes severe skin burns and eye damage
Precautionary statements
Keep only in original container.
[Prevention]
Do not breathe.
Wash hands thoroughly after handling.
Wear protective gloves/eye protection/face protection.
IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for
[Response]
breathing.
IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
if present and easy to do. Continue rinsing.
IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse
skin with water/shower.
Wash contaminated clothing before reuse.
Immediately call a POISON CENTER or doctor/physician.
Absorb spillage to prevent material damage.
[Storage] Store locked up.
[Disposal] Dispose of contents/container through a waste management company authorized by
the local government

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance
Substance/mixture:
Labeling]

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Component(s): 7-Acetoxy-4-bromomethylcoumarin [for HPLC Labeling]
Percent: >98.0%(LC)(T)
CAS Number: 2747-04-8
Chemical Formula: C12H9BrO4

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Section 4. FIRST AID MEASURES
Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Inhalation:
Immediately call a POISON CENTER or doctor/physician.
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. Immediately call a POISON CENTER or doctor/physician.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing.Immediately call a POISON CENTER or
doctor/physician.
Ingestion: Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT
induce vomiting.
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:
Specific hazards: Take care as it may decompose upon combustion or in high temperatures to
generate poisonous fume.
Specific methods: 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 extra personal protective equipment (P3 filter respirator for toxic particles). Keep
protective equipment and people away from and upwind of spill/leak. Entry to non-involved personnel should
emergency procedures: be controlled around the leakage area by 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
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 closed system if possible. Use a local exhaust if dust or aerosol will be
generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Use corrosive resistant equipment.
Storage
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store under inert gas.
Protect from moisture.
Store locked up.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Law is followed. Keep only in original container.
Labeling]

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator, self-contained breathing apparatus(SCBA), supplied air respirator,
etc. Use respirators approved under appropriate government standards and follow
local and national regulations.
Impervious gloves.
Hand protection:
Eye protection: Safety goggles. A face-shield, if the situation requires.
Skin and body protection: Impervious protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Form: crystal - powder
White - Slightly pale yellow
Color:
Odor: No data available
pH: No data available
Melting point/freezing point:182 °C
Boiling Point/Range: No data available
Flash Point: No data available
Explosive limits
Lower: No data available
No data available
Upper:
Density: No data available
No data available
Solubility:

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Section 10. STABILITY AND REACTIVITY
Stability: Stable under proper conditions.
Reactivity: No special reactivity has been reported.
Conditions to avoid: Light-sensitive, Moisture-sensitive
Incompartible materials: oxidizing agents, bases
Hazardous Decomposition Carbon monoxide, Carbon dioxide, Hydrogen bromide
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):
Mobillity in soil
log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):
Labeling]

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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
8: Corrosive.
Hazards Class:
UN-No: 3261
Corrosive solid, acidic, organic, n.o.s.
Proper shipping name:
Packing group: II

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26,
2002): 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

制备方法与用途

7-乙酰氧基-4-溴甲基香豆素被用作脂肪酸的荧光标记物。

反应信息

• 作为反应物：
  描述：

  7-乙酰氧基-4-溴甲基香豆素 在 sodium azide 作用下， 以 乙醇 、 水 为溶剂， 反应 11.0h， 以56%的产率得到4-(azidomethyl)-7-hydroxy-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and single enzyme activity of a clicked lipase–BSA hetero-dimer

  摘要：

  点击化学被用于构建一种新型的脂肪酶–BSA异二聚体，其中后者蛋白质作为基脚，使酶能够锚定在表面上，便于进行单酶研究。

  DOI：

  10.1039/b516551b
• 作为产物：
  描述：

  7-乙酰氧基-4-甲基香豆素 以60%的产率得到7-乙酰氧基-4-溴甲基香豆素
  参考文献：
  名称：

  US6133460

  摘要：

  公开号：

文献信息

• Halogen‐Mediated Membrane Transport: An Efficient Strategy for the Enhancement of Cellular Uptake of Synthetic Molecules
  作者：Harinarayana Ungati、Vijayakumar Govindaraj、Chithra R. Nair、Govindasamy Mugesh

  DOI：10.1002/chem.201806122

  日期：——

  biological molecules require specific membrane transporters and channel proteins that control the traffic of these molecules into and out of the cell. This work reports that the introduction of halogen atoms into a series of fluorescent molecules remarkably enhances their cellular uptake, and that their transport can be increased to more than 95 % by introducing two iodine atoms at appropriate positions. The

  哺乳动物细胞对荧光探针和治疗剂的吸收不良是生物学应用中的一个主要问题，涉及从荧光成像到活细胞内药物传递的各种领域。尽管气态分子（例如氧气和二氧化碳），疏水性物质（例如苯）以及小的极性但不带电荷的分子（例如水和乙醇）可以通过简单的被动扩散穿过细胞质膜，但许多合成分子和生物分子都需要特定的膜转运蛋白和控制这些分子进出细胞的通道蛋白。这项工作报告说，将卤素原子引入一系列荧光分子中可以显着增强其细胞摄取，并且通过在适当位置引入两个碘原子，可以将其转运提高到95％以上。当分子中存在碘原子时，荧光团的性质在细胞摄取中并不起主要作用，因为带有萘二甲酰亚胺，香豆素，BODIPY和pyr部分的化合物显示出相似的摄取。有趣的是，引入带有两个羟乙基硫基的马来酰亚胺基荧光团使分子能够穿过质膜和核膜，碘原子的存在进一步增强了跨这两个膜的传输。总的来说，这项研究提供了增强哺乳动物细胞对有机分子吸收的一般策略。引入带有
• An Efficient Procedure for the 1-Alkylation of 2-Nitroimidazoles and the Synthesis of a Probe for Hypoxia in Solid Tumours
  作者：Anthony Long、John Parrick、Richard J. Hodgkiss

  DOI：10.1055/s-1991-26552

  日期：——

  The N-alkylation of 2-nitroimidazole through its 'naked' anion, formed from its alkali metal salts in the presence of crown ethers and in homogeneous solution, is shown to be a useful preparative procedure. The reactions of α,ω-dihaloalkanes can be controlled to afford either the mono- or diheteroarylalkane. The procedure has been used to alkylate theophylline and to prepare a compound of use as a probe to identify, locate and quantify hypoxia in sections from solid tumours.

  裸露阴离子形式的2-硝基咪唑的N-烷基化反应，通过其在冠醚存在下由碱金属盐形成的均相溶液中进行，已被证明是一种有用的制备方法。α,ω-二卤代烷的反应可以被调控，以获得单或双杂芳基烷。该方法已被用于碱基化茶碱，并制备了一种可作为探针的化合物，用于在固体肿瘤组织切片中鉴定、定位和量化缺氧区域。
• COMPOSITIONS AND METHODS FOR TREATMENT OF VIRAL DISEASES
  申请人：Johansen Lisa M.

  公开号：US20100009970A1

  公开（公告）日：2010-01-14

  The present invention features compositions, methods, and kits useful in the treatment of viral diseases. In certain embodiments, the viral disease is caused by a single stranded RNA virus, a flaviviridae virus, or a hepatic virus. In particular embodiments, the viral disease is viral hepatitis (e.g., hepatitis A, hepatitis B, hepatitis C, hepatitis D, hepatitis E) and the agent or combination of agents includes sertraline, a sertraline analog, UK-416244, or a UK-416244 analog. Also featured are screening methods for identification of novel compounds that may be used to treat a viral disease.

  本发明涉及用于治疗病毒性疾病的组合物、方法和试剂盒。在某些实施方式中，病毒性疾病是由单链RNA病毒、黄病毒科病毒或肝病毒引起的。在特定实施方式中，病毒性疾病是病毒性肝炎（例如甲型肝炎、乙型肝炎、丙型肝炎、丁型肝炎、戊型肝炎），药剂或药剂组合包括舍曲林、舍曲林类似物、UK-416244或UK-416244类似物。还包括用于鉴定可用于治疗病毒性疾病的新化合物的筛选方法。
• Preparation and Molecular Recognition of SERS Probe Based on Gold Nanoparticles Constructed from PEG–Oligoamine Copolymer Possessing a Coumarin Group between PEG and Oligoamine
  作者：Hitoshi Furusho、Motoi Oishi、Tetsuo Kishi、Atsuo Yasumori、Yukio Nagasaki

  DOI：10.1246/cl.2010.52

  日期：2010.1.5

  Novel gold nanoparticles (GNPs) as a SERS probe were prepared using two types of functional PEG/oligoamine polymers possessing biotin as biotag molecules at the PEG end or a coumarin moiety as a Raman probe molecule between the PEG and oligoamine segments. Eventually, the GNPs showed excellent dispersion stability under physiological conditions, as well as remarkable SERS signal resulting from molecular recognition between streptavidin and the biotin tag, even in the presence of bovine serum albumin (BSA).

  研究人员使用两种功能性 PEG/oligoamine 聚合物制备了作为 SERS 探针的新型金纳米粒子（GNPs），这两种聚合物在 PEG 端部具有作为生物标记分子的生物素，或在 PEG 和寡胺段之间具有作为拉曼探针分子的香豆素分子。最终，GNPs 在生理条件下表现出极佳的分散稳定性，即使在牛血清白蛋白（BSA）存在的情况下，链霉亲和素与生物素标签之间的分子识别也能产生显著的 SERS 信号。
• Psoralens for pathogen inactivation
  申请人：Cerus Corporation

  公开号：US20030082510A1

  公开（公告）日：2003-05-01

  Psoralen compound compositions are synthesized which have primaryamino substitutions on the 3-, 4-, 5-, and 8-positions of the psoralen, which yet permit their binding to nucleic acid of pathogens. Reaction conditions that photoactivate these psoralens result in the inactivation of pathogens which contain nucleic acid. The compounds show similar activity in test systems to 4′ and 5′ derivatives of psoralen useful for inactivation of pathogens in blood products. In addition to the psoralen compositions, the invention contemplates such inactivating methods using the new psoralens.

  合成了一种含有3-、4-、5-和8-位置的主要氨基取代基的芳香光毒素化合物组合物，但仍允许它们与病原体的核酸结合。光活化这些芳香光毒素的反应条件导致含有核酸的病原体失活。这些化合物在测试系统中显示出与用于血液制品中病原体失活的4'和5'衍生物的类似活性。除了芳香光毒素组合物外，本发明还考虑使用新的芳香光毒素进行失活方法。

表征谱图