2-溴-3-甲酸 | 197846-05-2

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 中文名称: 2-溴-3-甲酸
• 中文别名: 2-溴3-呋喃甲酸；2-溴-3-呋喃甲酸
• 英文名称: 2-bromofuran-3-carboxylic acid
• CAS: 197846-05-2
• 化学式: C₅H₃BrO₃
• mdl: MFCD09702417
• 分子量: 190.981
• InChiKey: UJNWWTUUYCCIFL-UHFFFAOYSA-N

物化性质

• 熔点：
  160.5 °C
• 沸点：
  273.5±25.0 °C(Predicted)
• 密度：
  1.891±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  C
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2932190090
• WGK Germany：
  3

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 2-Bromofuran-3-carboxylic acid
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.
CAS-No. : 197846-05-2
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
Skin irritation (Category 2), H315
Eye irritation (Category 2), H319
Specific target organ toxicity - single exposure (Category 3), Respiratory system, H335
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
Xi Irritant R36/37/38
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)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : 2-Bromo-3-furoic acid
Formula : C5H3BrO3 C5H3BrO3
Molecular Weight : 190,98 g/mol
CAS-No. : 197846-05-2
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
2-Bromofuran-3-carboxylic acid
CAS-No. 197846-05-2 Skin Irrit. 2; Eye Irrit. 2; STOT <= 100 %
SE 3; H315, H319, H335
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
2-Bromofuran-3-carboxylic acid
CAS-No. 197846-05-2 Xi, R36/37/38 <= 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
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
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
no data available
Advice for firefighters
Wear self contained breathing apparatus for fire fighting 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. Evacuate personnel to safe areas. 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.
Recommended storage temperature: 2 - 8 °C
Light sensitive.
Specific end use(s)
A part 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
impervious clothing, 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 Melting point/range: 160 - 163 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration 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- log Pow: 1,373
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
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
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
May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
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
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-溴-3-甲酸 在 caesium carbonate 、 三苯基膦 、 palladium dichloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 、 甲苯 为溶剂， 反应 2.4h， 生成 2-乙烯基-3-糠酸甲酯
  参考文献：
  名称：

  乙烯基芳烃羰基化选择性的超分子控制：易于获得宝贵的β-醛中间体

  摘要：

  逆流而上！据报道，一种合理设计的区域选择性加氢甲酰化催化剂[Rh / L]，其中非共价配体-底物的相互作用使选择性从典型的α-醛到其他不利的产物β-醛发生了前所未有的逆转。该催化体系为精细化工行业的重要中间体开辟了新的，可持续的合成途径。

  DOI：

  10.1002/anie.201209582
• 作为产物：
  描述：

  3-糠酸 在 正丁基锂 、 溴 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.33h， 以73%的产率得到2-溴-3-甲酸
  参考文献：
  名称：

  光稳定的螺旋聚呋喃

  摘要：

  本报告描述了一类带有酯侧链的新型聚呋喃的设计和合成。大分子可以使用催化剂转移缩聚来合成，提供对分子量和分子量分布的精确控制。由于连接的亚单元的吸电子性质，这样获得的呋喃酯聚合物比它们的烷基类似物明显更耐光。最有趣的是，它们自发地折叠成一个紧凑的 π 堆积螺旋，产生一个复杂的多层圆柱形纳米粒子，其具有空心、刚性、共轭核，由聚呋喃主链和由酯侧链形成的柔软绝缘外层组成。聚合物侧链的长度决定了这种纳米粒子的外径，对于本研究中使用的己酯基团，外径等于~2。3 纳米。共轭核的内腔衬有氧原子，其有效直径为 0.4 nm。此外，在重复单元上安装更大的支化手性酯侧链产生的结构在溶剂改变时可以在有序手性螺旋折叠状态和无序展开状态之间可逆转变。

  DOI：

  10.1021/jacs.9b01567

文献信息

• 1-(2-PHENOXYMETHYLHETEROARYL)PIPERIDINE AND PIPERAZINE COMPOUNDS
  申请人：Stangeland Eric L.

  公开号：US20110230495A1

  公开（公告）日：2011-09-22

  The invention relates to compounds of formula I: where X, HAr, a, and R 1 through R 6 are as defined in the specification, or a pharmaceutically acceptable salt thereof. The compounds of formula I are serotonin and norepinephrine reuptake inhibitors. The invention also relates to pharmaceutical compositions comprising such compounds; methods of using such compounds; and process and intermediates for preparing such compounds.

  本发明涉及如下公式I的化合物： 其中X，HAr，a，以及R1至R6如说明书所述，或其药用可接受的盐。公式I的化合物是5-羟色胺和去甲肾上腺素再摄取抑制剂。本发明还涉及包含这些化合物的药物组合物；使用这些化合物的方法；以及制备这些化合物的方法和中间体。
• Diversity-Oriented Synthesis of Highly Fluorescent Fused Isoquinolines for Specific Subcellular Localization
  作者：Yoarhy A. Amador-Sánchez、Andrés Aguilar-Granda、Ricardo Flores-Cruz、Davir González-Calderón、Cynthia Orta、Braulio Rodríguez-Molina、Arturo Jiménez-Sánchez、Luis D. Miranda

  DOI：10.1021/acs.joc.9b02712

  日期：2020.1.17

  The title compounds were prepared via a three-step protocol starting with an Ugi four-component reaction, followed by either an intramolecular alkyne hydroarylation and subsequent alkene isomerization or through a Pomeranz-Fritsch-type cyclization with a final intramolecular Heck reaction. Subcellular localization studies of these compounds using green channel confocal microscopy revealed remarkable

  描述了靶向特定细胞器的新型高发射四环异喹啉的多组分多样性导向合成。通过Ugi四组分反应开始的三步方案制备标题化合物，然后进行分子内炔烃加氢芳基化和随后的烯烃异构化，或通过Pomeranz-Fritsch型环化反应进行最终的分子内Heck反应。使用绿色通道共聚焦显微镜对这些化合物进行亚细胞定位研究，揭示了其在活细胞中的显着且独特的分布模式，显示出前所未有的高选择性和成像对比度。分化的细胞器可视化-包括线粒体，溶酶体，高尔基体，内质网，
• Stitching Ynones with Nitromethanes: Domino Synthesis of Functionally Enriched Benzofurans and Benzothiophenes
  作者：Shweta Singh、Sharanya Nerella、Srihari Pabbaraja、Goverdhan Mehta

  DOI：10.1021/acs.joc.1c01104

  日期：2021.9.3

  This benzannulation was also explored with furan/thiophene based o-halo ynones wherein a Michael addition-SNAr process operates and nitromethanes leave their imprint to deliver nitro substituted benzo-furans and -thiophenes.

  已发现区域异构的 2-或 3-取代呋喃和噻吩炔酮与一系列硝基甲烷的方便的一锅苯并环化可直接获得密集且多样化的功能化苯并呋喃和苯并噻吩。在该协议中，硝基甲烷中的硝基作为递归碳负离子活化剂来设置串联迈克尔加成-6π-电环化，其最终的牺牲消除促进了芳构化和整体苯环化。还使用基于呋喃/噻吩的邻卤炔酮对这种苯环化进行了探索，其中迈克尔加成-S N Ar 过程运行，硝基甲烷留下它们的印记以提供硝基取代的苯并呋喃和噻吩。
• Diversity-oriented synthesis and cytotoxic screening of fused dihydropyrazin-2(1H)-ones through a Ugi 4-CR/deprotection/Heck sequence
  作者：Yoarhy A. Amador-Sánchez、Eduardo Hernández-Vázquez、Norberto González-Mojica、María T. Ramírez-Apan、Luis D. Miranda

  DOI：10.1016/j.tet.2020.131383

  日期：2020.9

  An expedited approach to the synthesis of fused-dihydropyrazin-2(1H)-ones from Ugi dimethylacetamide adducts is presented. The protocol relies on the formation of a C–N bond between the primary amide and the transitory oxocarbenium ion formed under acidic conditions, and then the construction of a fused-pyrazinone system after an intramolecular C(sp2)-C(sp2) Heck coupling. The methodology was able

  提出了从Ugi二甲基乙酰胺加合物合成稠合二氢吡嗪2（1 H）-ones的快速方法。该协议依赖于在酸性条件下伯酰胺和瞬态氧碳鎓离子之间形成C–N键，然后在分子内C（sp2）-C（sp2）Heck偶联后构建稠合吡嗪酮系统。该方法能够生成21种结构多样的聚氮杂杂环化合物，并对其在前列腺癌，乳腺癌和肺癌细胞系中的细胞毒性进行了筛选。对于两种化合物，IC50值分别为23.6和20.9μM的抗前列腺癌细胞PC-3观察到最佳活性。
• A Further Decrease in the Catalyst Loading for the Palladium-Catalyzed Direct Intramolecular Arylation of Amides and Sulfonamides
  作者：Nerea Conde、Fátima Churruca、Raul SanMartin、María Teresa Herrero、Esther Domínguez

  DOI：10.1002/adsc.201401129

  日期：2015.5.4

  The direct arylation of N‐substituted o‐bromobenzanilides and benzenesulfonamides via CH bond functionalization has been developed using very low catalyst loadings. This novel cost‐effective and more sustainable method relies on a PCN‐type palladium pincer complex as a highly active palladium source, providing a general and efficient access to phenanthridinones, biaryl sultams and related heterocyclic

  的直接芳基化Ñ取代ö -bromobenzanilides和苯磺酰胺通过Ç 已使用非常低的催化剂负载量开发了H键官能化。这种新颖的具有成本效益且更可持续的方法依赖于PCN型钯钳夹复合物作为高活性钯源，可提供对菲啶酮，联芳基杜仲和相关杂环系统的通用有效访问。在该方法中已经观察到水作为助溶剂的有益作用，其不受芳烃部分的电子作用或酰胺或磺酰胺氮上的空间上需要的取代基的严重影响。此外，为了理解所用钯配合物在该反应中的作用，已经进行了许多实验（动力学图，中毒试验，TEM，ESI）。