1-(4-溴苯基)-2-氧代吡咯烷-3-羧酸 | 226881-07-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 1-(4-溴苯基)-2-氧代吡咯烷-3-羧酸
• 英文名称: 1-(4-bromophenyl)-2-oxopyrrolidine-3-carboxylic acid
• CAS: 226881-07-8
• 化学式: C₁₁H₁₀BrNO₃
• 分子量: 284.109
• InChiKey: PHJMARYQKJGPKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933790090

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 1-(4-BROMOPHENYL)-2-OXO-3-
PYRROLIDINECARBOXYLIC ACID
CAS-No. : 226881-07-8
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 [EU-GHS/CLP]
Acute toxicity, Oral (Category 3)
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Toxic if swallowed. Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Danger
Hazard statement(s)
H301 Toxic if swallowed.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P301 + P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/
physician.
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
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R25 Toxic if swallowed.
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S45 In case of accident or if you feel unwell, seek medical advice immediately
(show the label where possible).
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C11H10BrNO3
Molecular Weight : 284,11 g/mol
Component Concentration
1-(4-BROMOPHENYL)-2-OXO-3-PYRROLIDINECARBOXYLIC ACID
CAS-No. 226881-07-8 -

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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. Take victim immediately to hospital. 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
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
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
Carbon oxides, nitrogen oxides (NOx), Hydrogen bromide gas
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
Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate
ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Prevent further leakage or spillage if safe to do so. 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.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling
the product.
Personal protective equipment
Eye/face protection
Face shield and safety glasses 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
Where risk assessment shows air-purifying respirators are appropriate use a full-face particle
respirator type N99 (US) or type P2 (EN 143) respirator cartridges as a backup to engineering
controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use
respirators and components tested and approved under appropriate government standards such
as NIOSH (US) or CEN (EU).

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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- log Pow: 2,11
octanol/water
p) Autoignition 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
no data available
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

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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 sensitization
no data available
Germ cell mutagenicity
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
Specific target organ toxicity - single exposure
May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion Toxic if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
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
no data available
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. Contact a licensed
professional waste disposal service to dispose of this material. 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: 2811 IMDG: 2811 IATA: 2811
UN proper shipping name
ADR/RID: TOXIC SOLID, ORGANIC, N.O.S. (1-(4-BROMOPHENYL)-2-OXO-3-
PYRROLIDINECARBOXYLIC ACID)
IMDG: TOXIC SOLID, ORGANIC, N.O.S. (1-(4-BROMOPHENYL)-2-OXO-3-
PYRROLIDINECARBOXYLIC ACID)
IATA: Toxic solid, organic, n.o.s. (1-(4-BROMOPHENYL)-2-OXO-3-PYRROLIDINECARBOXYLIC
ACID)
Transport hazard class(es)
ADR/RID: 6.1 IMDG: 6.1 IATA: 6.1
Packaging group
ADR/RID: III IMDG: III IATA: III
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：

  1-(4-溴苯基)-2-氧代吡咯烷-3-羧酸 在 sodium tetrahydroborate 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以81%的产率得到[1-(4-bromophenyl)pyrrolidin-3-yl]methanol
  参考文献：
  名称：

  Sodium borohydride–iodine mediated reduction of γ-lactam carboxylic acids followed by DDQ mediated oxidative aromatisation: a facile entry to N-aryl-formylpyrroles

  摘要：

  A simple methodology for the conversion of substituted N-aryl-gamma-lactam 2/3-carboxylic acids to substituted N-aryl-2/3-formyl-pyrroles has been developed. Several N-aryl-gamma-lactam 2/3-carboxylic acids were reduced to substituted (N-arylpyri-olidine-2/3-yl)-methanols in good yields at room temperature using sodium borohydride-iodine. Controlled oxidation and aromatisation of these alcohols using DDQ produced N-aryl-2/3-formyl-pyrroles. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.107
• 作为产物：
  描述：

  1,1-环丙烷二甲酸环异亚丙酯 、 4-溴苯胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以70.6%的产率得到1-(4-溴苯基)-2-氧代吡咯烷-3-羧酸
  参考文献：
  名称：

  发现新型双重c-Met / HDAC抑制剂是一种有前途的癌症治疗策略。

  摘要：

  由于c-Met抑制剂的临床试验疗效低下且获得性耐药，基于c-Met与HDAC的协同作用，设计并合成了新型的c-Met和HDAC双重抑制剂。我们引入了2-吡咯烷酮以形成c-Met抑制剂的5原子接头，而异羟肟酸作为HDAC抑制剂的锌结合基序。高活性双重抑制剂15f对c-Met（IC 50  = 12.50 nM）和HDAC1（IC 50  = 26.97 nM）均显示出优异且平衡的活性。在那些经过测试的肿瘤细胞系中，15f与伏立诺他（SAHA）和卡波替尼（XL184）相比，具有更高的有效抗增殖活性。但是，通过与SAHA和Foretinib的等摩尔混合物进行比较，我们没有观察到这些化合物显示出明显的协同抗增殖作用。然而，发现化合物15f诱导细胞凋亡并导致细胞周期停滞在G2 / M期。这项概念验证研究为发现多靶点抗肿瘤药物提供了有效的策略。

  DOI：

  10.1016/j.bioorg.2020.103970

文献信息

• Method for production of pyrrolidinone derivatives
  申请人：Mitsui Chemicals, Inc.

  公开号：US06207825B1

  公开（公告）日：2001-03-27

  A compound represented by the following formula (12) useful as an intermediate for production of drug or agricultural chemical: (wherein R21 to R25 are each independently a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms, a perfluoroalkyl group of 1 to 4 carbon atoms, a cyano group, a nitro group, an amino group, a carboxyl group, a thiol group, an alkylthio group of 1 to 4 carbon atoms or a carbamoyl group) can be produced by reacting a compound represented by the formula (13): (wherein R21 to R25 have the same definitions as given above) with 1,1-cyclopropanedicarboxylic acid. The compound of the formula (12) is useful as a raw material for production of a pyrrolidinone compound useful as an active ingredient of drug.

  以下公式（12）表示的化合物可作为制药品或农药的中间体：（其中R21至R25分别独立地是氢原子、羟基、卤原子、1至4个碳原子的烷基、1至4个碳原子的烷氧基、1至4个碳原子的全氟烷基、氰基、硝基、氨基、羧基、硫醇基、1至4个碳原子的烷硫基或羰基）。可通过将以下公式（13）表示的化合物（其中R21至R25的定义与上述相同）与1,1-环丙烷二羧酸反应来制备公式（12）表示的化合物。公式（12）的化合物可作为制药品活性成分吡咯烷酮化合物的原料。
• Pyrrolidinone derivative compound
  申请人：Schering Aktiengesellschaft

  公开号：US20030171578A1

  公开（公告）日：2003-09-11

  A compound represented by the following formula (12) useful as an intermediate for production of drug or agricultural chemical: 1 (wherein R 21 to R 25 are each independently a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms, a perfluoroalkyl group of 1 to 4 carbon atoms, a cyano group, a nitro group, an amino group, a carboxyl group, a thiol group, an alkylthio group of 1 to 4 carbon atoms or a carbamoyl group) can be produced by reacting a compound represented by the formula (13): 2 (wherein R 21 to R 25 have the same definitions as given above) with 1,1-cyclopropanedicarboxylic acid. The compound of the formula (12) is useful as a raw material for production of a pyrrolidinone compound useful as an active ingredient of drug.

  以下化合物的化学式（12）可作为制药或农药中间体使用：1（其中R21到R25分别独立地表示氢原子、羟基、卤素原子、1至4个碳原子的烷基、1至4个碳原子的烷氧基、1至4个碳原子的全氟烷基、氰基、硝基、氨基、羧基、硫醇基、1至4个碳原子的烷硫基或氨基甲酰基）。该化合物可通过将以下化合物（13）与1,1-环丙烷二羧酸反应制得：2（其中R21到R25具有以上给出的相同定义）。化合物的化学式（12）可作为制药活性成分吡咯烷酮化合物的原料。
• [EN] METAP-2 INHIBITORS, PHARMACEUTICAL COMPOSITIONS AND THERAPEUTIC METHODS THEREOF<br/>[FR] INHIBITEURS DE METAP-2, COMPOSITIONS PHARMACEUTIQUES ET LEURS MÉTHODES THÉRAPEUTIQUES
  申请人：CANWELL BIOTECH LTD

  公开号：WO2022206350A1

  公开（公告）日：2022-10-06

  Provided herein are inhibitors of methionine aminopeptidase 2 (MetAP-2) and pharmaceutical compositions thereof, and their use and methods of treatment, reduction or prevention of certain diseases or conditions associated with MetAP-2 (e.g., cancer, obesity, rheumatoid arthritis and psoriasis).

  本文提供了甲硫氨酸氨肽酶2（MetAP-2）的抑制剂及其制药组合物，以及它们的用途和治疗方法，用于减少或预防与MetAP-2相关的某些疾病或症状（例如癌症、肥胖症、类风湿性关节炎和牛皮癣）。
• A method for production of pyrrolidinone derivatives
  申请人：MITSUI CHEMICALS, INC.

  公开号：EP0916656A2

  公开（公告）日：1999-05-19

  A compound represented by the following formula (12) useful as an intermediate for production of drug or agricultural chemical: (wherein R21 to R25 are each independently a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms, a perfluoroalkyl group of 1 to 4 carbon atoms, a cyano group, a nitro group, an amino group, a carboxyl group, a thiol group, an alkylthio group of 1 to 4 carbon atoms or a carbamoyl group) can be produced by reacting a compound represented by the formula (13): (wherein R21 to R25 have the same definitions as given above) with 1,1-cyclopropanedicarboxylic acid. The compound of the formula (12) is useful as a raw material for production of a pyrrolidinone compound useful as an active ingredient of drug.

  由下式(12)代表的化合物，可用作生产药物或农业化学品的中间体： (其中 R21 至 R25 各自独立地为氢原子、羟基、卤素原子、1 至 4 个碳原子的烷基、1 至 4 个碳原子的烷氧基、1 至 4 个碳原子的全氟烷基、氰基、硝基、氨基、羧基、硫醇基、1 至 4 个碳原子的烷硫基或氨基甲酰基)可通过式(13)代表的化合物反应制得： (其中 R21 至 R25 的定义与上述相同）与 1,1-环丙烷二羧酸反应制得。式（12）化合物可用作生产可用作药物活性成分的吡咯烷酮化合物的原料。
• Sodium borohydride–iodine mediated reduction of γ-lactam carboxylic acids followed by DDQ mediated oxidative aromatisation: a facile entry to N-aryl-formylpyrroles
  作者：Pranab Haldar、Joyram Guin、Jayanta K. Ray

  DOI：10.1016/j.tetlet.2004.12.107

  日期：2005.2

  A simple methodology for the conversion of substituted N-aryl-gamma-lactam 2/3-carboxylic acids to substituted N-aryl-2/3-formyl-pyrroles has been developed. Several N-aryl-gamma-lactam 2/3-carboxylic acids were reduced to substituted (N-arylpyri-olidine-2/3-yl)-methanols in good yields at room temperature using sodium borohydride-iodine. Controlled oxidation and aromatisation of these alcohols using DDQ produced N-aryl-2/3-formyl-pyrroles. (C) 2004 Elsevier Ltd. All rights reserved.