1-(4-溴苯基)-2-羟基乙基-1-酮 | 3343-45-1

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(4-溴苯基)-2-羟基乙基-1-酮
• 中文别名: 1-(4-溴苯基)-2-羟基-1-乙酮
• 英文名称: 4-bromo-2-hydroxyacetophenone
• 英文别名: 1-(4-bromophenyl)-2-hydroxyethanone；1-(4-bromophenyl)-2-hydroxyethan-1-one；4-bromo-α-hydroxyacetophenone
• CAS: 3343-45-1
• 化学式: C₈H₇BrO₂
• 分子量: 215.046
• InChiKey: FGROGLJVXNYNQC-UHFFFAOYSA-N

物化性质

• 熔点：
  137 °C
• 沸点：
  321.5±22.0 °C(Predicted)
• 密度：
  1.596±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2914700090

SDS

Name:	1-(4-Bromophenyl)-2-hydroxyethan-1-one 97% Material Safety Data Sheet
Synonym:	(4-Bromobenzoyl)methano
CAS:	3343-45-1

Section 1 - Chemical Product MSDS Name:1-(4-Bromophenyl)-2-hydroxyethan-1-one 97% Material Safety Data Sheet
Synonym:(4-Bromobenzoyl)methano

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3343-45-1	1-(4-Bromophenyl)-2-hydroxyethan-1-one	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 3343-45-1: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 140 - 142 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H7BrO2
Molecular Weight: 215

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Acids, bases, oxidizing agents, reducing agents, acid chlorides.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, bromine, bromide fumes.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 3343-45-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-(4-Bromophenyl)-2-hydroxyethan-1-one - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 3343-45-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 3343-45-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3343-45-1 is not listed on the TSCA inventory.
It is for research and development use only.

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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-羟基乙基-1-酮 在 吡啶 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 19.0h， 生成 (R)-4-(4-bromophenyl)-4-vinyl-1,3-dioxolane
  参考文献：
  名称：

  碳酸乙烯乙烯酯与甲醛的钯催化脱羧环加成反应：叔乙烯基乙二醇的对映选择性结构

  摘要：

  开发了一种通过钯催化碳酸亚乙烯酯与甲醛的不对称脱羧环加成反应，对叔乙烯基二醇进行对映选择性构建的有效方法。通过在温和的反应条件下使用由[Pd 2（dba）3 ]·CHCl 3原位生成的钯配合物和亚磷酰胺配体作为催化剂，该方法可以使外消旋的4-取代的4-乙烯基-1,3-二氧戊环转化作为亚甲基缩醛保护的叔乙烯基二醇，可将-2-酮转化为相应的1,3-二氧戊环，并具有良好或优异的对映选择性。

  DOI：

  10.1002/anie.201403754
• 作为产物：
  描述：

  2'-氯-4-溴苯乙酮 在 水 作用下， 反应 0.42h， 以82%的产率得到1-(4-溴苯基)-2-羟基乙基-1-酮
  参考文献：
  名称：

  微波辅助从α-卤代和α，α'-二溴代酮合成α-羟基酮，α-二酮和吡嗪衍生物

  摘要：

  微波辐射下α-卤代酮（α-溴代和α-氯代酮）的新型反应可得到相应的α-羟基酮和吡嗪衍生物，收率很高。在α，α′-二溴酮的情况下，获得了α-二酮。该反应为α-羟基酮，α-二酮，α-氯酮和吡嗪衍生物的合成提供了一种新的，清洁且方便的方法。

  DOI：

  10.1016/j.tetlet.2006.10.087

文献信息

• BRM TARGETING COMPOUNDS AND ASSOCIATED METHODS OF USE
  申请人：Arvinas Operations, Inc.

  公开号：US20190300521A1

  公开（公告）日：2019-10-03

  The present disclosure relates to bifunctional compounds, which find utility as modulators of SMARCA2 or BRM (target protein). In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a ligand that binds to the Von Hippel-Lindau E3 ubiquitin ligase, and on the other end a moiety which binds the target protein, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein are treated or prevented with compounds and compositions of the present disclosure.

  本公开涉及双功能化合物，其作为SMARCA2或BRM（靶蛋白）的调节剂具有实用性。具体而言，本公开涉及包含一端结合Von Hippel-Lindau E3泛素连接酶的配体，另一端结合靶蛋白的双功能化合物，使得靶蛋白与泛素连接酶靠近以实现靶蛋白的降解（和抑制）。本公开展示了与靶蛋白降解/抑制相关的广泛药理活性。本公开的化合物和组合物用于治疗或预防由靶蛋白聚集或积累导致的疾病或紊乱。
• A Macrocycle/Molecular-Clip Complex that Functions as a Quadruply Controllable Molecular Switch
  作者：Pinn-Tsong Chiang、Pin-Nan Cheng、Chi-Feng Lin、Yi-Hung Liu、Chien-Chen Lai、Shie-Ming Peng、Sheng-Hsien Chiu

  DOI：10.1002/chem.200500676

  日期：2006.1.11

  synthesis of a molecular clip with TTF side-walls and its binding behavior towards electron-deficient guests, namely the formation of macrocycle/molecular-clip supramolecular complexes in solution. Four different sets of external stimuli--the K(+)/[2.2.2]cryptand, NH(4) (+)/Et(3)N and (p-BrPh)(3)NSbCl(6)/Zn pairs, and heating/cooling cycles-control the movement of this molecular switch between its threaded

  在本文中，我们报道了具有TTF侧壁的分子夹的合成及其对电子缺乏客体的结合行为，即在溶液中形成大环/分子夹超分子复合物。四组不同的外部刺激-K（+）/ [2.2.2] cryptand，NH（4）（+）/ Et（3）N和（p-BrPh）（3）NSbCl（6）/ Zn对以及加热/冷却循环控制该分子开关在其带螺纹状态和非带螺纹状态之间的运动，并提供肉眼可观察到的颜色变化。该大环/分子夹复合系统不仅可以被视为四次使用的分子开关，而且还可以通过这些刺激中的三个作为三输入分子NOR功能逻辑门进行操作，该门可以通过UV可见光进行监控光谱学。
• Palladium-Catalyzed Diastereoselective Formal [5 + 3] Cycloaddition for the Construction of Spirooxindoles Fused with an Eight-Membered Ring
  作者：Ben Niu、Xiao-Yun Wu、Yin Wei、Min Shi

  DOI：10.1021/acs.orglett.9b01748

  日期：2019.6.21

  A Pd-catalyzed formal [5 + 3] intermolecular cycloaddition reaction of isatin-derived α-(trifluoromethyl)imines with aryl substituted vinylethylene carbonates (VECs) has been reported, affording trifluoromethyl-group-containing spirooxindoles fused with an eight-membered ring as a single diastereoisomer in good yields in the presence of a Brønsted acid in a one-pot manner under mild conditions. The

  据报导，钯衍生的Isatin衍生的α-（三氟甲基）亚胺与芳基取代的乙烯基碳酸亚乙酯（VEC）的形式[5 + 3]的分子间环加成反应，提供了含三氟甲基的螺环新多烯与八元环稠合而成在温和的条件下，在布朗斯台德酸的存在下，以一锅法以高收率得到一个单一的非对映异构体。还使用手性膦配体实现了该反应的不对称形式，同时将得到的产物进一步转化以在氧化时得到螺氧基吲哚并吡咯烷衍生物。
• Iron-TEMPO-Catalyzed Domino Aerobic Alcohol Oxidation/Oxidative Cross-Dehydrogenative Coupling for the Synthesis of α-Keto Amides
  作者：Surya Srinivas Kotha、Selvaraj Chandrasekar、Samrat Sahu、Govindasamy Sekar

  DOI：10.1002/ejoc.201402961

  日期：2014.11

  An iron-TEMPO-catalyzed (TEMPO = 2,2,6,6-tetramethyl-1-piperidinyloxy), aerobic process was developed to synthesize α-keto amides. This reaction proceeds through a domino alcohol oxidation/oxidative cross-dehydrogenative coupling sequence, uses 2-hydroxyacetophenones and amines as the starting materials, and takes place under molecular oxygen, which makes the transformation highly efficient, practical

  开发了铁-TEMPO 催化（TEMPO = 2,2,6,6-四甲基-1-哌啶基氧基）的有氧工艺来合成 α-酮酰胺。该反应通过多米诺醇氧化/氧化交叉脱氢偶联序列进行，以2-羟基苯乙酮和胺类为起始原料，在分子氧下进行，使转化高效、实用且环保。
• Pd-Catalyzed Decarboxylative Olefination: Stereoselective Synthesis of Polysubstituted Butadienes and Macrocyclic P-glycoprotein Inhibitors
  作者：Bichao Song、Peipei Xie、Yingzi Li、Jiping Hao、Lu Wang、Xiangyang Chen、Zhongliang Xu、Haitian Quan、Liguang Lou、Yuanzhi Xia、K. N. Houk、Weibo Yang

  DOI：10.1021/jacs.0c00078

  日期：2020.6.3

  The efficient and stereoselective synthesis of polysubstituted butadienes, especially the multifunctional butadiene, represents a great challenge in organic synthesis. Herein, we wish to report a distinctive Pd(0) car-bene-initiated decarboxylative olefination approach that enables the direct coupling of diazo esters with vinylethylene carbonates (VECs), vinyl oxazolidinones, or vinyl benzoxazinones

  多取代丁二烯尤其是多功能丁二烯的高效立体选择性合成是有机合成中的一大挑战。在此，我们希望报告一种独特的 Pd(0) 碳烯引发的脱羧烯化方法，该方法能够将重氮酯与乙烯基碳酸亚乙酯 (VEC)、乙烯基恶唑烷酮或乙烯基苯并恶嗪酮直接偶联，以提供醇、胺或苯胺。含有 1,3-二烯，产率中等至高，具有出色的立体选择性。该协议具有操作简单、反应条件温和、底物范围广泛和可扩展性等特点。值得注意的是，分离并表征了一种结构独特的烯丙基 Pd(II) 中间体。DFT 计算和控制实验表明，稀有的 Pd(0) 卡宾中间体可能参与该反应。此外，作为新型构件的多取代丁二烯前所未有地组装成大环化合物，有效抑制了 P-糖蛋白 (P-gp)，并以 190 倍的速度显着逆转了癌细胞的多药耐药性。

表征谱图