2,3-二溴代-1,3-二苯基-1-丙酮 | 611-91-6

• 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 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 2,3-二溴代-1,3-二苯基-1-丙酮
• 中文别名: 二溴化苯乙烯基苯基酮；2,3-二溴-3-苯基苯丙酮
• 英文名称: 2,3-dibromo-1,3-diphenylpropane-1-one
• 英文别名: 2,3-dibromo-1,3-diphenylpropan-1-one；2,3-Dibromo-3-phenylpropiophenone
• CAS: 611-91-6
• 化学式: C₁₅H₁₂Br₂O
• mdl: MFCD00017861
• 分子量: 368.068
• InChiKey: LYAGBKGGYRLVTR-UHFFFAOYSA-N

物化性质

• 熔点：
  156 °C
• 沸点：
  411.5±45.0 °C(Predicted)
• 密度：
  1.631±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R34
• 储存条件：
  室温

SDS

Name:	2 3-Dibromo-3-phenylpropiophenone 98% Material Safety Data Sheet
Synonym:	Benzalacetophenone dibromid
CAS:	611-91-6

Section 1 - Chemical Product MSDS Name:2 3-Dibromo-3-phenylpropiophenone 98% Material Safety Data Sheet
Synonym:Benzalacetophenone dibromid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
611-91-6	2,3-Dibromo-3-phenylpropiophenone	98%	210-282-9

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# 611-91-6: 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: odorless
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 156 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: Negligible.
Specific Gravity/Density:
Molecular Formula: C15H12Br2O
Molecular Weight: 368.07

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable.
Conditions to Avoid:
Incompatible materials, direct sunlight..
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, hydrogen bromide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 611-91-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,3-Dibromo-3-phenylpropiophenone - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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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# 611-91-6: No information available.
Canada
CAS# 611-91-6 is listed on Canada's NDSL List.
CAS# 611-91-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 611-91-6 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

二溴查尔酮是一种有用的合成子，能够生成吡唑啉、羟基吡唑啉和异恶唑等多种生物活性分子。它通过抑制超氧化物的产生和脂质过氧化对肿瘤细胞具有抗氧化作用，并且在癌症研究中得到应用。

反应信息

• 作为反应物：
  描述：

  2,3-二溴代-1,3-二苯基-1-丙酮 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以80%的产率得到二苯甲酰基甲烷
  参考文献：
  名称：

  新光下的古老故事：X射线粉末衍射为已知的有机固态重排反应提供了新颖的见解

  摘要：

  据报道，对位-溴-苯偶氮三苯甲酰甲烷进行了众所周知的固态重排，首次进行了原位衍射研究。这项原理验证的研究表明，现代实验室X射线粉末衍射技术以及最新的加工工具可用于监测和描述有机固态反应的机理，同时也证明了其对有机固相反应的必要性。原位形成的结晶相的结构表征。（doi：10.5562 / cca2127）

  DOI：

  10.5562/cca2127
• 作为产物：
  描述：

  ω-苄基苯乙酮 在 N-溴代丁二酰亚胺(NBS) 、 copper(ll) bromide 作用下， 以 乙腈 为溶剂， 生成 2,3-二溴代-1,3-二苯基-1-丙酮
  参考文献：
  名称：

  N-溴代琥珀酰亚胺光解α-溴代酮合成α，β-二溴代酮：α-溴代酮的光诱导β-溴化

  摘要：

  在NBS的存在下照射α-溴丙苯酮会导致形成α，β-二溴苯乙酮，这可以看作是α-溴苯乙酮的β-溴化。该反应被认为经历了一系列反应。光诱导的C-Br键断裂，消除HBr，得到α，β-不饱和酮中间体，并添加Br 2是由HBr和NBS之间的反应形成的。从反应的机理研究中，我们还发现了一种非常方便的α，β-二溴苯乙酮的α-脱溴方法，该方法是在丙酮或2-丙醇中简单照射二溴酮，而无需使用任何添加剂。我们的结果表明，可以通过光化学方法将溴添加到羰基的α，β或两个位置上或从羰基的α，β或两个位置上消除，这使含溴羰基化合物的合成选择具有多种用途。

  DOI：

  10.1016/j.tet.2019.130684
• 作为试剂：
  描述：

  5,6-二氨基-1,3-二甲基脲嘧啶 在 2,3-二溴代-1,3-二苯基-1-丙酮 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.67h， 生成 8-苯基茶碱
  参考文献：
  名称：

  5,6-二氨基-1,3-二甲基尿嘧啶与查耳酮的卤素衍生物的反应

  摘要：

  DOI：

  10.1007/bf00474494

文献信息

• Electrophilic Bromination of Alkenes, Alkynes, and Aromatic Amines with Potassium Bromide/Orthoperiodic Acid under Mild Conditions
  作者：Ardeshir Khazaei、Mohammad Zolfigol、Eskandar Kolvari、Nadiya Koukabi、Hamid Soltani、Fatemeh Komaki

  DOI：10.1055/s-0029-1216994

  日期：2009.11

  Bromination of alkenes, alkynes, and aromatic amines has efficiently been carried out at room temperature in short reaction times using potassium bromide/orthoperiodic acid in dichloromethane-water (1:1) to prepare the corresponding bromo compounds with excellent yields. bromination - orthoperiodic acid - alkenes - aromatic amines

  在室温下，使用溴化钾/原高碘酸在二氯甲烷-水（1：1）中，烯烃，炔烃和芳族胺的溴化反应已在室温下短时间内有效地进行，从而以高收率制备了相应的溴代化合物。 溴化-正高碘酸-烯烃-芳香胺
• Electrophilic Bromination of Alkenes, Alkynes, and Aromatic Amines with Iodic Acid/Potassium Bromide Under Mild Conditions
  作者：Ardeshir Khazaei、Mohammad Ali Zolfigol、Eskandar Kolvari、Nadiya Koukabi、Hamid Soltani、Leyla Sharaf Bayani

  DOI：10.1080/00397910903349992

  日期：2010.8.31

  Bromination of alkenes, alkynes, and aromatic amines has efficiently been carried out at room temperature in short reaction times using HIO3/KBr in CH2Cl2/H2O (1:1) to prepare corresponding brominated compounds in excellent yields.

  使用 HIO3/KBr 的 CH2Cl2/H2O (1:1) 溶液，可以在室温下在短时间内有效地进行烯烃、炔烃和芳香胺的溴化反应，以优异的产率制备相应的溴化化合物。
• An efficient bromination of alkenes using cerium(IV) ammonium nitrate (CAN) and potassium bromide
  作者：Vijay Nair、Sreeletha B Panicker、Anu Augustine、Tesmol G George、Siji Thomas、M Vairamani

  DOI：10.1016/s0040-4020(01)00712-8

  日期：2001.8

  Bromination of alkenes using a combination of potassium bromide and cerium(iv) ammonium nitrate (CAN) in a two phase system consisting of water and dichloromethane affords the corresponding dibromides in excellent yield. The reaction most likely involves the addition of the bromine radical generated from bromide ion by CAN and subsequent formation of the dibromide.

  在由水和二氯甲烷组成的两相体系中，使用溴化钾和铈（iv）硝酸铵（CAN）的组合将烯烃溴化，可以以优异的收率得到相应的二溴化物。该反应最可能涉及通过CAN添加由溴离子产生的溴自由基，并随后形成二溴化物。
• Visible light-mediated metal-free double bond deuteration of substituted phenylalkenes
  作者：Roman Iakovenko、Jan Hlaváč

  DOI：10.1039/d0gc03081c

  日期：——

  Photoactivated metal free deuteration of a double bond was developed in an environmentally friendly manner.

  双键的光活化金属无氘化反应以环境友好的方式进行了开发。
• Solvolytic Stereoselective Debromination of<i>vic</i>-Dibromides with HMPA
  作者：Jitender Mohan Khurana、Geeti Bansal、Sushma Chauhan

  DOI：10.1246/bcsj.74.1089

  日期：2001.6

  A simple and efficient procedure for the debromination of vic-dibromides has been reported with hexamethylphosphoric triamide at 155–160 °C under a nitrogen atmosphere without the aid of any reagent.

  据报道，在 155–160 °C 下，在氮气氛下，无需任何试剂的帮助，六甲基磷酰三胺脱溴的简单有效程序。