2-溴-1-[4-(2-甲基丙基)苯基]-1-丙酮 | 80336-64-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-溴-1-[4-(2-甲基丙基)苯基]-1-丙酮
• 中文别名: 2-溴-1-(4-异丁基苯基)-1-丙酮
• 英文名称: 2-bromo-1-(4-isobutylphenyl)-1-propanone
• 英文别名: 2-bromo-1-(4'-isobutyl-phenyl)-propan-1-one；2-Bromo-1-(4-isobutylphenyl)propan-1-one；2-bromo-1-[4-(2-methylpropyl)phenyl]propan-1-one
• CAS: 80336-64-7
• 化学式: C₁₃H₁₇BrO
• 分子量: 269.181
• InChiKey: SVGMFVCPJFHTRE-UHFFFAOYSA-N

物化性质

• 熔点：
  63 °C

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R34
• 海关编码：
  2914700090

SDS

Name:	2-Bromo-1-(4-isobutylphenyl)propan-1-one 97% Material Safety Data Sheet
Synonym:	2'-Bromo-4-isobutylpropiophenon
CAS:	80336-64-7

Section 1 - Chemical Product MSDS Name:2-Bromo-1-(4-isobutylphenyl)propan-1-one 97% Material Safety Data Sheet
Synonym:2'-Bromo-4-isobutylpropiophenon

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
80336-64-7	2-Bromo-1-(4-isobutylphenyl)propan-1-o	97%	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:
Vacuum or sweep up material and place into a suitable disposal 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# 80336-64-7: 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: 60 - 62 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: C13H17BrO
Molecular Weight: 269

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 80336-64-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Bromo-1-(4-isobutylphenyl)propan-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 SOLID, ACIDIC, ORGANIC, N.O.S.*
Hazard Class: 8
UN Number: 3261
Packing Group: III
IMO
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
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# 80336-64-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 80336-64-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 80336-64-7 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：白色结晶，熔点为63-65℃。

用途：作为非甾体抗炎镇痛药布洛芬的中间体。

生产方法：通过将对异丁基苯丙酮与过溴化物型三甲基苄铵树脂在二氯甲烷中反应制得。

反应信息

• 作为反应物：
  描述：

  2-溴-1-[4-(2-甲基丙基)苯基]-1-丙酮 在 吡啶 、 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.75h， 生成 (S)-1,1-dimethoxy-1-(4-isbutylphenyl)-2-propanol
  参考文献：
  名称：

  Duh, Tsai-Hui; Wang, Yi-Fong; Wu, Ming-Jung, Journal of the Chinese Chemical Society, 1995, vol. 42, # 3, p. 579 - 584

  摘要：

  DOI：
• 作为产物：
  描述：

  对异丁基苯丙酮 在 溴 作用下， 以 溶剂黄146 为溶剂， 生成 2-溴-1-[4-(2-甲基丙基)苯基]-1-丙酮
  参考文献：
  名称：

  在芳基α-硒基和芳基α-碲-乙基基酮中通过氧化芳基迁移制备2-芳基丙酸的新方法

  摘要：

  氧化与米kitones的芳基α-phenylseleno -或芳基α-phenyltelluro乙基乙烯缩醛氯过苯甲酸制备通过用二苯基二硒化物，钠或二碲化物二苯基-钠相应的α溴代化合物，分别得到2-羟乙基芳基丙酸酯通过芳基基团迁移以中等至良好的收率。

  DOI：

  10.1039/c39840000426

文献信息

• Photochemical rearrangement of α-chloro-propiophenones to α-arylpropanoic acids: studies on chirality transfer and synthesis of (S)-(+)-ibuprofen and (S)-(+)-ketoprofen
  作者：Harikisan R. Sonawane、Nanjundiah S. Bellur、Dilip G. Kulkarni、Nagaraj R. Ayyangar

  DOI：10.1016/s0040-4020(01)80835-8

  日期：1994.1

  α-arylpropanoic acids (4) from α chloro-propiophenones (5) is described. It involves carbonyl triplet excited state directed 1,2-aryl migration of the aryl group which has been found to be highly dependent upon the nature of the aryl substituent. The mode of this rearrangement is probed by the study of the photobehaviour of a set of optically active α-chloro-propiophenones. The results suggest that the nature of

  描述了一种新的单步高效光化学方法，可从α氯丙酮（5）中分离出α-芳基丙酸（4）。它涉及芳基的羰基三重激发态定向的1，2-芳基迁移，已发现其高度依赖于芳基取代基的性质。通过对一组光学活性的α-氯-苯乙酮的光行为的研究来探究这种重排的方式。结果表明，羰基三联体（n，π * /π，π *）的性质在手性转移中起重要作用。该方法在光学活性布洛芬（4e）和酮洛芬（26），尽管光学产量中等。
• [EN] METHOD OF PREPARATION OF DERIVATIVES OF SUBSTITUTED 2-ARYL AIKANOIC ACIDS<br/>[FR] METHODE DE PREPARATION DE DERIVES D'ACIDES 2-ARYLALCANOIQUES SUBSTITUES
  申请人：ZENTIVA AS

  公开号：WO2004046080A1

  公开（公告）日：2004-06-03

  The invention relates to a new preparation method of derivatives of substituted 2-­arylaikanoic acids. The compounds are used for the preparation of histaminically active compounds and antiphlogistics. The compounds are prepared by reaction of suitably substituted a-halogen acetophenones with orthoformates with catalysis by mineral and Lewis acids.

  该发明涉及一种新的制备取代2-芳基丙酸衍生物的方法。这些化合物用于制备组胺活性化合物和抗炎药。这些化合物通过适当取代的α-卤代苯乙酮与正甲酸酯在矿物酸和路易斯酸的催化下反应制备而成。
• 一种4-异丁基苯基酮类化合物的合成方法
  申请人：北京光大恒信科技发展有限公司

  公开号：CN106278840A

  公开（公告）日：2017-01-04

  本发明公开了一种4-异丁基苯基酮类化合物的合成方法，所述化合物结构如下：所述化合物以4-异丁基苯为起始原料，取代磺酸和取代磺酸盐为催化剂，与酰氯反应得到，即如下反应：应用这种方法合成4-异丁基苯基酮类化合物，操作简便，反应条件温和，环境友好，具有良好的工业化前景。
• Photochemistry of substituted propiophenones: An interesting α-and aryl substituents effect on their photobehaviour I,II
  作者：Harikisan R. Sonawane、Nanjundiah S. Bellur、G.M. Nazeruddin

  DOI：10.1016/0040-4020(95)00690-a

  日期：1995.10

  Photochemistry of different α-substituted and phenyl-substituted propiophenones in methanol is investigated with a view to delineate the substituent effect with a special reference tu their rearrangement to α-arylpropanoic acids, an important class of nonsteroidal antiinflammatory agents. The results thus obtained bringsforth an important element of their reactivityprofile i.e. the α-chloro-substituent

  研究了甲醇中不同的α-取代的和苯基取代的苯乙酮的光化学，目的是通过特殊的参考来描述取代基的作用，特别是将它们重排为重要的非甾体类抗炎剂α-芳基丙酸。由此获得的结果成为其反应性概况的重要要素，即α-氯代取代基与核烷基取代基（对位）的结合有利于1，2-芳基迁移，从而导致合成有用的α-芳基丙酸的反应。
• Manufacture of alpha-arylalkanoic acids and precursors
  申请人：Syntex Pharmaceuticals International Limited

  公开号：US04542237A1

  公开（公告）日：1985-09-17

  .alpha.-Arylalkanoic acids or esters, orthoesters or amides thereof are prepared by forming an .alpha.-hydroxy ketal or thioketal of an aryl alkyl ketone, activating the .alpha.-hydroxy substituent with an esterifying agent to form the corresponding ketal or thioketal ester substrate, wherein the ester group is sufficiently labile to non-catalytically disassociate from the substrate in a protic or dipolar, aprotic solvent, maintaining the ester substrate in contact with the protic or dipolar, aprotic solvent or mixtures thereof for a time sufficient to form the corresponding .alpha.-arylakanoic acid or ester, orthoester or amide thereof, and optionally concomitantly or sequentially hydrolyzing any ester, orthoester or amide formed to the corresponding .alpha.-arylalkanoic acid.

  通过形成芳基烷基酮的α-羟基缩醛或硫缩醛，激活α-羟基取代基以形成相应的缩醛或硫缩醛酯底物，其中酯基足够不稳定，可以在带有质子或双极非质子溶剂中与底物非催化地解离，将酯底物与质子或双极非质子溶剂或其混合物接触足够的时间以形成相应的α-芳基烷酸或酯，缩醛或酰胺，可选择同时或顺序水解任何形成的酯，缩醛或酰胺以形成相应的α-芳基烷酸。