2-溴-2'-氯苯乙酮 | 5000-66-8

• 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 - 有机氧化合物
• 中文名称: 2-溴-2'-氯苯乙酮
• 中文别名: 2-溴-2′-氯苯乙酮；2-溴-2-氯苯乙酮；2-溴-2’-氯苯乙酮；α-溴代邻氯苯乙酮；alpha-溴代邻氯苯乙酮；а-溴代邻氯苯乙酮
• 英文名称: 2-chlorophenacyl bromide
• 英文别名: 2-Bromo-1-(2-chlorophenyl)ethan-1-one；2-bromo-2'-chloroacetophenone；2-bromo-1-(2-chlorophenyl)ethanone；2-bromo-2’-chloroacetophenone；α-bromo-2-chloroacetophenone；2-bromo-2′-chloroacetophenone；2'-chloro-2-bromoacetophenone
• CAS: 5000-66-8
• 化学式: C₈H₆BrClO
• mdl: MFCD00832993
• 分子量: 233.492
• InChiKey: WZWWEVCLPKAQTA-UHFFFAOYSA-N

物化性质

• 沸点：
  105 °C1 mm Hg(lit.)
• 密度：
  1.602 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• 溶解度：
  可溶于丙酮、氯仿、乙酸乙酯、甲醇
• 稳定性/保质期：
  常温常压下，该物质为稳定油状液体。其沸点在129-131℃（0.6kPa）。

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  8
• 安全说明：
  S26,S36/37/39,S45
• 危险品运输编号：
  UN 2922 8/PG 2
• WGK Germany：
  3
• 海关编码：
  2914700090
• 危险类别：
  8
• 危险品标志：
  C
• 危险类别码：
  R34
• 包装等级：
  II
• 危险性防范说明：
  P273,P280,P305+P351+P338,P310
• 危险性描述：
  H314,H402
• 储存条件：
  请将药品存放在避光、阴凉干燥的地方，并密封保存。

SDS

Name:	2-Bromo-1-(2-chlorophenyl)ethan-1-one tech Material Safety Data Sheet
Synonym:	2-Bromo-2'-chloroacetophenon
CAS:	5000-66-8

Section 1 - Chemical Product MSDS Name:2-Bromo-1-(2-chlorophenyl)ethan-1-one tech Material Safety Data Sheet
Synonym:2-Bromo-2'-chloroacetophenon

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5000-66-8	2-Bromo-1-(2-chlorophenyl)ethan-1-one		unlisted

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do not induce vomiting. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
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 foam, dry chemical, or carbon dioxide.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.

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Section 7 - HANDLING and STORAGE
Handling:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area.

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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# 5000-66-8: 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: Liquid
Color: colorless - pale yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 162 - 166 deg C @ 20mmHg
Freezing/Melting Point: Not available.
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: C8H6BrClO
Molecular Weight: 233.49

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, chlorine, carbon monoxide, carbon dioxide, hydrogen bromide, bromine.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 5000-66-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Bromo-1-(2-chlorophenyl)ethan-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
Shipping Name: CORROSIVE LIQUID, ACIDIC, ORGANIC, N.O.S.*
Hazard Class: 8
UN Number: 3265
Packing Group: III
IMO
Shipping Name: CORROSIVE LIQUID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3265
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE LIQUID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3265
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 5000-66-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 5000-66-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5000-66-8 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

制备方法与用途

化学性质： 这是一种油状液体，沸点在129至131℃（0.6kPa）之间。

用途： 主要用作医药中间体。

生产方法： 由邻氯苯乙酮通过溴化制得。具体步骤为：将苯和邻氯苯乙酮加入反应锅中，在室温下搅拌并分批滴加一部分溴素，待反应液褪色后继续滴加剩余的溴素，并根据实际情况适当加热。溴素滴加完毕后，搅拌1小时，然后加入冰水进行搅拌和静置分层。取上层苯层，用碳酸钠溶液洗涤后再用水洗。最后回收苯，即可得到α-溴代邻氯苯乙酮。

反应信息

• 作为反应物：
  描述：

  2-溴-2'-氯苯乙酮 在 ammonium hydroxide 、 碘 作用下， 反应 1.0h， 以19.4 mg的产率得到2-氯苯甲酰胺
  参考文献：
  名称：

  1,3-二溴-5,5-二甲基乙内酰脲介导的末端烯烃在水中的氧化酰胺化

  摘要：

  通过用1，3-二溴-5，5-二甲基乙内酰脲处理，然后与分子碘和HCl水溶液反应，将多种末端烯烃在水中以25-86％的产率转化为相应的酰胺。一锅中加入NH 3（或胺）。这种无金属和有机溶剂的方案不仅适用于苯乙烯衍生物，而且首次在末端脂族烯烃上效果很好。

  DOI：

  10.1039/c7ob02329d
• 作为产物：
  描述：

  1-(2-氯苯基)乙醇 在 氢溴酸 、 双氧水 作用下， 以 水 、 乙腈 为溶剂， 反应 6.0h， 以52%的产率得到2-溴-2'-氯苯乙酮
  参考文献：
  名称：

  H2O2/HBr 系统 – 多个方向，但一个选择：氧化 – 将仲醇溴化为单溴酮或二溴酮†

  摘要：

  在这项工作中，我们发现H 2 O 2 –HBr(aq)系统可以从脂肪族和仲苄醇合成α-一溴酮和α,α'-二溴酮，收率高达91%。通过改变过氧化氢和氢溴酸的量，可以选择性地引导该过程形成单溴酮或二溴酮。应用方便、设备简单、反应活性多方面以及符合绿色化学原理，使得H 2 O 2 –HBr(aq)系统的应用在实验室和工业界非常有吸引力。尽管已知酮具有通过Baeyer-Villiger反应氧化或在过氧化氢和布朗斯台德酸存在下形成具有O-O部分的化合物过氧化的已知特性，但所提出的氧化-溴化过程是选择性的。

  DOI：

  10.1039/c8ra04885a

文献信息

• Metal-free hydration of aromatic haloalkynes to α-halomethyl ketones
  作者：Min Ye、Yuelu Wen、Huifang Li、Yejuan Fu、Qinghao Wang

  DOI：10.1016/j.tetlet.2016.09.088

  日期：2016.11

  A highly regioselective and efficient metal-free hydration of aromatic haloalkynes to α-halomethyl ketones using cheap tetrafluoroboric acid as catalyst is described. The protocol is conducted under convenient conditions and affords products in good to excellent yields, with broad substrate scope, including a variety of aromatic alkynyl chlorides, alkynyl bromides, and alkynyl iodides.

  描述了使用廉价的四氟硼酸作为催化剂的芳香族卤代炔烃的高度区域选择性和有效的无金属水合为α-卤代甲基酮。该方案是在方便的条件下进行的，并以良好的收率提供优良的产品，具有广泛的底物范围，包括各种芳族炔基氯，炔基溴化物和炔基碘化物。
• Asymmetric Hydrogenation of α-Primary and Secondary Amino Ketones: Efficient Asymmetric Syntheses of (−)-Arbutamine and (−)-Denopamine
  作者：Gao Shang、Duan Liu、Scott E. Allen、Qin Yang、Xumu Zhang

  DOI：10.1002/chem.200700594

  日期：2007.9.17

  Two beta-receptor agonists (-)-denopamine and (-)-arbutamine were prepared in good yields and enantioselectivities by asymmetric hydrogenation of unprotected amino ketones for the first time by using Rh catalysts bearing electron-donating phosphine ligands. A series of alpha-primary and secondary amino ketones were synthesized and hydrogenated to produce various 1,2-amino alcohols in good yields and

  通过使用带有给电子膦配体的Rh催化剂进行不保护的氨基酮的不对称氢化，以高收率和对映选择性制备了两种β受体激动剂（-）-地巴胺和（-）-arbutamine。合成了一系列的α-伯氨基和仲氨基酮并进行氢化，以高收率和良好的对映选择性生产出各种1,2-氨基醇。这种Rh电子给体的膦催化的不对称氢化反应代表了手性氨基醇不对称合成的最有希望和最方便的方法之一。
• Reprogramming Epoxide Hydrolase to Improve Enantioconvergence in Hydrolysis of Styrene Oxide Scaffolds
  作者：Fu‐Long Li、Yan‐Yan Qiu、Yu‐Cong Zheng、Fei‐Fei Chen、Xu–Dong Kong、Jian‐He Xu、Hui‐Lei Yu

  DOI：10.1002/adsc.202000898

  日期：2020.11.4

  Enantioconvergent hydrolysis by epoxide hydrolase is a promising method for the synthesis of important vicinal diols. However, the poor regioselectivity of the naturally occurring enzymes results in low enantioconvergence in the enzymatic hydrolysis of styrene oxides. Herein, modulated residue No. 263 was redesigned based on structural information and a smart variant library was constructed by site‐directed

  通过环氧水解酶的对映体收敛水解是一种重要的邻位二醇合成的有前途的方法。但是，天然酶的区域选择性差会导致苯乙烯氧化物的酶促水解中对映体收敛性低。在此，根据结构信息重新设计了263号残基，并使用“优化的氨基酸字母”通过定点修饰构建了一个智能变体文库，以提高来自Vigna radiata（Vr EH2）的环氧水解酶的区域选择性。M263Q变体对间位异构体R异构体的区域选择性系数（r）与野生型相比，预取代的苯乙烯氧化物提高了40-63倍，变体M263V对对位取代的苯乙烯氧化物的R异构体也表现出更高的区域选择性，从而提高了苯乙烯氧化物支架水解中的对映体收敛性。结构上的洞察力表明263号残基在通过改变结合环境来调节底物结合构象中的关键作用。此外，亲核残基Asp101和环氧化物的两个碳原子之间的攻击距离差异增加，为区域选择性的提高提供了证据。几种易于合成的高价值邻位二醇（> 88％收率，90％–98％ 
• Tandem Wittig Reaction–Ring Contraction of Cyclobutanes: A Route to Functionalized Cyclopropanecarbaldehydes
  作者：Federico Cuccu、Lorenzo Serusi、Alberto Luridiana、Francesco Secci、Pierluigi Caboni、David J. Aitken、Angelo Frongia

  DOI：10.1021/acs.orglett.9b02690

  日期：2019.10.4

  An original tandem reaction consisting of a Wittig reaction-ring contraction process between α-hydroxycyclobutanone and phosphonium ylides has been developed. Highly functionalized cyclopropanecarbaldehydes are obtained in good to high yield.

  已经开发出由α-羟基环丁酮和磷化yl之间的维蒂希反应-环收缩过程组成的原始串联反应。以良好或高收率获得高度官能化的环丙烷甲醛。
• FUSED MORPHOLINOPYRIMIDINES AND METHODS OF USE THEREOF
  申请人：FORUM Pharmaceuticals Inc.

  公开号：US20170044182A1

  公开（公告）日：2017-02-16

  The present disclosure relates to Fused Morpholinopyrimidines, pharmaceutical compositions comprising an effective amount of a Fused Morpholinopyrimidine and methods for using a Fused Morpholinopyrimidine in the treatment of a neurodegenerative disease, comprising administering to a subject in need thereof an effective amount of a Fused Morpholinopyrimidine.

  本公开涉及融合吗啉吡嘧啶类化合物，包括有效量的融合吗啉吡嘧啶类化合物的药物组合物，以及在治疗神经退行性疾病中使用融合吗啉吡嘧啶类化合物的方法，包括向需要的受试者施用有效量的融合吗啉吡嘧啶类化合物。