6-溴-2H-1,4-苯并噁嗪-3(4H)-酮 | 24036-52-0

• 物质功能分类: 医药中间体 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 中文名称: 6-溴-2H-1,4-苯并噁嗪-3(4H)-酮
• 中文别名: 6-溴-2H-1,4-苯并恶嗪-3(4H)-酮；6-溴苯并噁嗪酮；6-溴苯并恶嗪-3(4H)-酮；6-溴苯并恶嗪-3（4H）-酮
• 英文名称: 6-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-one
• 英文别名: 6-bromo-2H-benzo[b][1,4]oxazin-3(4H)-one；6-bromo-2H-1,4-benzoxazin-3(4H)-one；6-bromo-4H-benzo[1,4]oxazin-3-one；6-bromo-4H-1,4-benzoxazin-3-one
• CAS: 24036-52-0
• 化学式: C₈H₆BrNO₂
• mdl: MFCD00461173
• 分子量: 228.045
• InChiKey: UQCFMEFQBSYDHY-UHFFFAOYSA-N

物化性质

• 熔点：
  220-225 °C
• 沸点：
  376.8±42.0 °C(Predicted)
• 密度：
  1.676
• 溶解度：
  可溶于二甲基亚砜、甲醇
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解。请避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36
• 危险类别码：
  R22
• 海关编码：
  2934999090
• WGK Germany：
  2
• 危险标志：
  GHS07
• 危险性描述：
  H302,H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 储存条件：
  保持贮藏器密封，并将其放入一个紧密的容器中。应储存在阴凉、干燥的地方。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 6-Bromo-2H-1,4-benzoxazin-3(4H)-one
CAS-No. : 24036-52-0
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 4)
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
Harmful if swallowed. Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful 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.
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)
R22 Harmful 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.
S36 Wear suitable protective clothing.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C8H6BrNO2
Molecular Weight : 228,04 g/mol
Component Concentration
6-Bromo-2H-1,4-benzoxazin-3(4H)-one
CAS-No. 24036-52-0 -

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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
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
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
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.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
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).

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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: 220 - 225 °C
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: 2,119
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
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
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
Inhalation - 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 Harmful 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: - 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
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 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.

制备方法与用途

概述

6-溴-2H-1,4-苯并噁嗪-3(4H)-酮是一种有机中间体，可用于制备一类具有PPAR激动活性的药物。

制备

6-溴-2H-1,4-苯并噁嗪-3(4H)-酮可以通过以下步骤合成：首先将2.5g（13mmol）的2-氨基-4-溴苯酚加入三口瓶中，然后向其中加入80mL四氢呋喃。接着，滴加2.4mL（17mmol）的三乙胺。待反应体系冷却至0℃后，缓慢滴加1.12mL（14mmol）的氯乙酰氯，并在0℃下搅拌10分钟后，将温度升至室温并继续搅拌2小时。随后，将体系降温至0℃，分批加入1.05g（26mmol）的氢化钠，保持0℃反应20分钟后再升温至室温反应2小时。最后，浓缩反应混合物，并用100mL水淬灭反应。过滤得到的沉淀，用水洗涤并干燥滤饼，最终获得约2.5g红色固体。

用途

6-溴-2H-1,4-苯并噁嗪-3(4H)-酮可用于构建嘧啶基取代苯并噁嗪酮以及小分子凝乳酶抑制剂的结构单元。

反应信息

• 作为反应物：
  描述：

  6-溴-2H-1,4-苯并噁嗪-3(4H)-酮 在 劳森试剂 、 盐酸 、 四(三苯基膦)钯 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 palladium 10% on activated carbon 、 氢气 、 溴 、 potassium acetate 、 双(三甲基硅烷基)氨基钾 、 sodium carbonate 、 一水合肼 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 12.5h， 生成 (R)-7-(2-fluorophenyl)-4-methyl-6-[(R)-1-(3-methylazetidin-3-yl)ethyl]-2,10-dihydro-9-oxa-1,2,4a-triazaphenanthren-3-one
  参考文献：
  名称：

  Optimized Protein Kinase Cθ (PKCθ) Inhibitors Reveal Only Modest Anti-inflammatory Efficacy in a Rodent Model of Arthritis

  摘要：

  We previously demonstrated that selective inhibition of protein kinase C theta (PKC theta) with triazinone 1 resulted in dose-dependent reduction of paw swelling in a mouse model of arthritis.1,2 However, a high concentration was required for efficacy, thus providing only a minimal safety window. Herein we describe a strategy to deliver safer compounds based on the hypothesis that optimization of potency in concert with good oral pharmacokinetic (PK) properties would enable in vivo efficacy at reduced exposures, resulting in an improved safety window. Ultimately, transformation of 1 yielded analogues that demonstrated excellent potency and PK properties and fully inhibited IL-2 production in an acute model. In spite of good exposure, twice-a-day treatment with 17l in the glucose-6-phosphate isomerase chronic in vivo mouse model of arthritis yielded only moderate efficacy. On the basis of the exposure achieved, we conclude that PKC theta inhibition alone is insufficient for complete efficacy in this rodent arthritis model.

  DOI：

  10.1021/jm5013006
• 作为产物：
  描述：

  4-溴-2-硝基苯酚 在 铁粉 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 生成 6-溴-2H-1,4-苯并噁嗪-3(4H)-酮
  参考文献：
  名称：

  靶向血清素转运蛋白、多巴胺 D2 受体和毛-A 酶的新型吲哚衍生物的合成、对接、3-D-Qsar 和生物测定：寻找潜在的多靶点定向配体

  摘要：

  2,3-二氢-苯并[1,4]恶嗪-4-基)-2-{4-[3-(1H-3吲哚基)-丙基]-1-哌嗪基}-乙酰胺的一系列27种化合物, 系列 I：7(a-o) 和 (2-{4-[3-(1H-3-吲哚基)-丙基]-1-哌嗪基}-乙酰胺)-N-(2-吗啉-4-基-乙基)-氟化苯甲酰胺系列 II：13(a-l) 被合成并评估为针对多巴胺 D2 受体、血清素转运蛋白 (SERT) 和单胺氧化酶-A (MAO-A) 的新型多靶标配体，用于治疗重度抑郁症障碍（MDD）。所有测定的化合物都显示出纳摩尔范围内的 SERT 亲和力，其中五个显示出 5 到 10 nM 的 Ki 值。化合物 7k (Ki = 5.63 ± 0.82 nM) 和 13c (Ki = 6.85 ± 0.19 nM) 表现出最高的效力。D2 的亲和力范围从微摩尔到纳摩尔，而 MAO-A 抑制更为离散。尽管如此，化合物 7m 和 7n 显示出对纳摩尔范围内的

  DOI：

  10.3390/molecules25204614

文献信息

• [EN] NOVEL HETEROCYCLIC DERIVATIVES USEFUL AS SHP2 INHIBITORS<br/>[FR] NOUVEAUX DÉRIVÉS HÉTÉROCYCLIQUES UTILES EN TANT QU'INHIBITEURS DE SHP2
  申请人：JACOBIO PHARMACEUTICALS CO LTD

  公开号：WO2017211303A1

  公开（公告）日：2017-12-14

  Provided are certain pyrazine derivatives (I) as SHP2 inhibitors which is shown as formula (I), their synthesis and their use for treating a SHP2 mediated disorder. More particularly, provided are fused heterocyclic derivatives useful as inhibitors of SHP2, methods for producing such compounds and methods for treating a SHP2-mediated disorder.

  提供了某些吡嗪衍生物（I）作为SHP2抑制剂，其化学式如下（I），以及它们的合成和用于治疗SHP2介导的疾病。更具体地，提供了有用作为SHP2抑制剂的融合杂环衍生物，生产这类化合物的方法以及治疗SHP2介导的疾病的方法。
• Synthesis and biological evaluation of 2,4,5-trisubstituted thiazoles as antituberculosis agents effective against drug-resistant tuberculosis
  作者：Uttam B. Karale、Vagolu Siva Krishna、E. Vamshi Krishna、Amit S. Choudhari、Manjulika Shukla、Vikas R. Gaikwad、B. Mahizhaveni、Sidharth Chopra、Sunil Misra、Dhiman Sarkar、Dharmarajan Sriram、V.N. Azger Dusthackeer、Haridas B. Rode

  DOI：10.1016/j.ejmech.2019.05.082

  日期：2019.9

  The dormant and resistant form of Mycobacterium tuberculosis presents a challenge in developing new anti-tubercular drugs. Herein, we report the synthesis and evaluation of trisubstituted thiazoles as antituberculosis agents. The SAR study has identified a requirement of hydrophobic substituent at C2, ester functionality at C4, and various groups with hydrogen bond acceptor character at C5 of thiazole

  结核分枝杆菌的休眠和耐药形式在开发新的抗结核药物方面提出了挑战。在此，我们报道了三取代噻唑类作为抗结核剂的合成和评价。SAR研究已经确定了噻唑支架在C2处具有疏水取代基，在C4处具有酯官能度以及在C5处具有氢键受体特性的各种基团的需求。这导致鉴定出13h和13p为先导化合物。这些化合物选择性地抑制了休眠的结核分枝杆菌H37Ra菌株和结核分枝杆菌H37Rv。重要的是，13h和13p对CHO细胞无毒。这13p显示出对耐多药结核病分离株的活性。
• Preparation of Enantioenriched Alkylcarbastannatranes via Nucleophilic Inversion of Alkyl Mesylates for Use in Stereospecific Cross-Coupling Reactions
  作者：Glenn Ralph、Mark R. Biscoe

  DOI：10.1021/acs.organomet.9b00467

  日期：2019.10.28

  We report the preparation of enantioenriched secondary alkylcarbastannatranes via a stereoinvertive SN2 reaction of enantioenriched alkyl mesylates and carbastannatranyl anion equivalents. Using this process, enantioenriched secondary alcohols may be converted into highly enantioenriched alkylcarbastannatranes, which are useful in stereospecific cross-coupling reactions.

  我们报告了通过对映体富集的烷基甲磺酸盐和碳原子化炔基阴离子等价物的立体转化S N 2反应制备对映体富集的仲烷基氨基甲酸酯。使用该方法，可以将对映体富集的仲醇转化为高度对映体富集的烷基碳黄烷烃，其可用于立体有择的交叉偶联反应中。
• Alpha2C adrenoreceptor agonists
  申请人：McCormick D. Kevin

  公开号：US20070093477A1

  公开（公告）日：2007-04-26

  In its many embodiments, the present invention relates to a novel class of phenylmorpholine and phenylthiomorpholine compounds useful as α2C adrenergic receptor agonists, pharmaceutical compositions containing the compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the α2C adrenergic receptor agonists using such compounds or pharmaceutical compositions.

  在其多种实施形式中，本发明涉及一类新型的苯基吗啡啶和苯基硫代吗啡啶化合物，这些化合物可用作α2C肾上腺素受体激动剂，包含这些化合物的药物组合物，以及使用这些化合物或药物组合物治疗、预防、抑制或改善与α2C肾上腺素受体激动剂相关的一种或多种疾病的方法。
• [EN] INHIBITORS OF VIRAL REPLICATION, THEIR PROCESS OF PREPARATION AND THEIR THERAPEUTICAL USES<br/>[FR] INHIBITEURS DE RÉPLICATION VIRALE, LEUR PROCÉDÉ DE SYNTHÈSE ET LEURS APPLICATIONS THÉRAPEUTIQUES
  申请人：BIODIM LAB

  公开号：WO2012137181A1

  公开（公告）日：2012-10-11

  The present invention relates to compounds of formula (1) as claimed in claim 1, their use in the treatment or the prevention of viral disorders, including HIV. (Formula I)

  本发明涉及权利要求1中所述的式(1)化合物，及其用于治疗或预防病毒疾病，包括HIV。