8-甲氧基香豆素 | 2445-81-0

• 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: 8-甲氧基香豆素
• 中文别名: 8-甲氧基-2H-苯并吡喃-2-酮
• 英文名称: 8-methoxycoumarine
• 英文别名: 8-methoxycoumarin；8-methoxy-2H-chromen-2-one；8-Methoxy-cumarin；8-methoxychromen-2-one
• CAS: 2445-81-0
• 化学式: C₁₀H₈O₃
• mdl: MFCD00016708
• 分子量: 176.172
• InChiKey: ODRDTKMYQDXVGG-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于氯仿；甲醇；二甲基亚砜；可溶于二氯甲烷；

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2932209090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 8-Methoxycoumarin
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
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
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Oral (Category 4), H302
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xn Harmful R22
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
Precautionary statement(s) none
Supplemental Hazard none
Statements
Other hazards
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.

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SECTION 3: Composition/information on ingredients
Substances
Molecular weight : 176,17 g/mol
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
8-Methoxycoumarin
Acute Tox. 4; H302 <= 100 %
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
8-Methoxycoumarin
Xn, R22 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
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. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
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
Nature of decomposition products not known.
Advice for firefighters
Wear self-contained breathing apparatus for firefighting if necessary.
Further information
No data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. 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
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Storage class (TRGS 510): Non Combustible Solids
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 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
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
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 No data available
boiling range
g) Flash point No data available
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 No data available
n) Water solubility No data available
o) Partition coefficient: n- No data available
octanol/water
p) Auto-ignition 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
Stable under recommended storage conditions.
Possibility of hazardous reactions
No data available
Conditions to avoid
No data available
Incompatible materials
No data available
Hazardous decomposition products
In the event of fire: see section 5

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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 sensitisation
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
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
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.
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. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
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
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Acute Tox. Acute toxicity
H302 Harmful if swallowed.
Full text of R-phrases referred to under sections 2 and 3
Xn Harmful
R22 Harmful if swallowed.
Further information
Copyright 2014 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.

反应信息

• 作为反应物：
  描述：

  8-甲氧基香豆素 在 甲醇 、 乙醚 、 氢碘酸 、 镍 作用下， 生成 2,2-dimethylchroman-8-ol
  参考文献：
  名称：

  Hallet; Huls, Bulletin des Societes Chimiques Belges, 1952, vol. 61, p. 33,39

  摘要：

  DOI：
• 作为产物：
  描述：

  木榴油 在 (乙腈)[(2-联苯)二叔丁基膦]六氟锑酸金(I) 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 17.0h， 生成 8-甲氧基香豆素
  参考文献：
  名称：

  金（I）催化的苯酚丙酸酯和某些相关醚的分子内氢芳基化反应作为选择性功能化香豆素和2 H -Chromenes的途径

  摘要：

  报道了有效组装一系列由苯酚衍生的丙酸酯的方法，包括母体系统56，以及它们的Au（I）催化的环化（分子内氢芳基化），得到相应的香豆素（例如1）。通过这样的方法已经实现了天然产物例如ayapin（144）和scoparone（145）的简单合成，并且首先对它们进行单晶X射线分析。描述了一种用于将诸如156的炔丙基醚转化为天然存在的少年激素生物合成抑制剂的异构体2 H-苯并二茂烯I（159）的方法。

  DOI：

  10.1021/acs.joc.0c02011

文献信息

• Benzopyranopyrrole and benzopyranopyridine .alpha.-1 adenergic compounds
  申请人：Abbott Laboratories

  公开号：US05891882A1

  公开（公告）日：1999-04-06

  The present invention relates to a compound of the formula ##STR1## and the pharmaceutically acceptable salts thereof wherein W is a bicyclic heterocyclic ring system. The compounds are .alpha.-1 adrenergic antagonists and are useful in the treatment of BPH; also disclosed are .alpha.-1 antagonist compositions and a method for antagonizing .alpha.-1 adrenoreceptors and tr

  这项发明涉及一种具有以下结构的化合物##STR1##及其药用可接受的盐，其中W是一个双环杂环环系统。这些化合物是α-1肾上腺素受体拮抗剂，对于治疗BPH很有用；还披露了α-1拮抗剂组合物和拮抗α-1肾上腺素受体的方法。
• Visible-Light-Induced Regioselective Alkylation of Coumarins via Decarboxylative Coupling with <i>N</i>-Hydroxyphthalimide Esters
  作者：Can Jin、Zhiyang Yan、Bin Sun、Jin Yang

  DOI：10.1021/acs.orglett.9b00327

  日期：2019.4.5

  An efficient photocatalytic decarboxylative 3-position alkylation of coumarins by using alkyl N-hydroxyphthalimide esters as alkylation reagents has been developed. A variety of NHP esters derived from aliphatic carboxylic acids (primary, secondary, and tertiary) has been proved to be tolerated for this decarboxylation process, affording a broad scope of 3-alkylated coumarin derivatives in moderate

  通过使用烷基N-羟基邻苯二甲酰亚胺酯作为烷基化试剂，开发了一种有效的香豆素的光催化脱羧3-位烷基化反应。事实证明，这种脱羧方法可耐受多种衍生自脂族羧酸（伯，仲和叔）的NHP酯，可提供中等收率至优异收率的广泛范围的3-烷基化香豆素衍生物。该协议因其条件温和，易于获得的起始原料，操作简便和宽泛的官能团耐受性而得到强调。
• Palladium-Catalyzed C−H Functionalization of Phenyl 2-Pyridylsulfonates
  作者：Bin Li、Dong-Dong Guo、Shi-Huan Guo、Gao-Fei Pan、Ya-Ru Gao、Yong-Qiang Wang

  DOI：10.1002/asia.201601413

  日期：2017.1.3

  An efficient palladium(II)‐catalyzed intermolecular direct ortho‐alkenylation and acetoxylation of phenols has been developed. The reaction proceeded via a seven‐membered cyclopalladated intermediate and showed complete regio‐ and diastereoselectivity. The approach also provided an efficient route for the synthesis of coumarins and benzofurans.

  已经开发出了一种有效的钯（II）催化酚间的分子间直接邻链烯基化和乙酰氧基化方法。反应通过一个七元的环钯中间体进行，显示出完全的区域选择性和非对映选择性。该方法还提供了合成香豆素和苯并呋喃的有效途径。
• Iron-Catalyzed Regioselective Decarboxylative Alkylation of Coumarins and Chromones with Alkyl Diacyl Peroxides
  作者：Can Jin、Xun Zhang、Bin Sun、Zhiyang Yan、Tengwei Xu

  DOI：10.1055/s-0037-1611864

  日期：2019.8

  A facile iron-catalyzed decarboxylative radical coupling of alkyl diacyl peroxides with coumarins or chromones has been developed, affording a highly efficient approach to synthesize a variety of α-alkylated coumarins and β-alkylated chromones. The reaction proceeded smoothly without adding any ligand or additive and provided the corresponding products containing a wide scope of functional groups in

  已经开发了一种简便的铁催化的烷基二酰基过氧化物与香豆素或色酮的脱羧自由基偶联，为合成各种 α-烷基化香豆素和 β-烷基化色酮提供了一种高效的方法。该反应在不添加任何配体或添加剂的情况下顺利进行，并以中等至优异的产率提供了含有广泛官能团的相应产物。该协议的突出特点是其高区域选择性、易于获得的起始材料和操作简单。
• Direct C-3 alkylation of coumarins <i>via</i> decarboxylative coupling with carboxylic acids
  作者：Farnaz Jafarpour、Masoumeh Darvishmolla、Narges Azaddoost、Farid Mohaghegh

  DOI：10.1039/c8nj06410e

  日期：——

  method for selective C-3 alkylation of coumarins using carboxylic acids as alkyl sources is reported. This process offers a practical method for the facile construction of 3-alkyl coumarins with a broad substrate scope. The reaction works under metal-free and aqueous media and both cyclic and acyclic aliphatic carboxylic acids participate in this radical C–C cross coupling reaction.

  报道了一种使用羧酸作为烷基源的香豆素选择性C-3烷基化的新方法。该方法提供了一种实用的方法，用于容易地构建具有广泛底物范围的3-烷基香豆素。该反应在无金属和水性介质下进行，并且环状和无环脂族羧酸均参与该自由基C-C交叉偶联反应。

表征谱图