4'-溴苯丙酮 | 10342-83-3

• 物质功能分类: 化学试剂 - 有机试剂 - 芳香酮
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4'-溴苯丙酮
• 中文别名: 对溴苯丙酮；4"-溴苯丙酮；对丙酰基溴苯；4-溴代苯丙酮
• 英文名称: 4'-Bromopropiophenone
• 英文别名: 1-(4-bromo-phenyl)-propan-1-one；p-bromopropiophenone；4’-bromopropiophenone；4′-bromopropiophenone；1-(4-bromophenyl)propan-1-one
• CAS: 10342-83-3
• 化学式: C₉H₉BrO
• mdl: MFCD00000106
• 分子量: 213.074
• InChiKey: UOMOSYFPKGQIKI-UHFFFAOYSA-N

物化性质

• 熔点：
  45-47 °C(lit.)
• 沸点：
  138-140 °C14 mm Hg(lit.)
• 密度：
  1.3841 (rough estimate)
• 闪点：
  >230 °F
• 溶解度：
  可溶于乙腈（少许）、氯仿（少许）、甲醇
• 稳定性/保质期：

  遵照规格使用和储存则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2914399090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  请将密封于阴凉干燥处。

SDS

Name:	4 -Bromopropiophenone 97% Material Safety Data Sheet
Synonym:	None Known
CAS:	10342-83-3

Section 1 - Chemical Product MSDS Name:4 -Bromopropiophenone 97% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
10342-83-3	4'-Bromopropiophenone	97%	233-745-7

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or 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:

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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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use water spray to cool fire-exposed containers. Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate 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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 10342-83-3: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: moist, white to off-white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 138 - 140 deg C @ 14.00mmHg
Freezing/Melting Point: 45.00 - 47.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: > 110 deg C (> 230.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C9H9BrO
Molecular Weight: 213.07

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, reducing agents, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents, reducing agents, strong acids, strong bases.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, hydrogen bromide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 10342-83-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4'-Bromopropiophenone - 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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
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# 10342-83-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 10342-83-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 10342-83-3 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：白色结晶体，熔点为45-47℃。

反应信息

• 作为反应物：
  描述：

  4'-溴苯丙酮 在 palladium diacetate sodium tetrahydroborate 、 sodium carbonate 、 三苯基膦 作用下， 以 丙醇 、 乙醇 为溶剂， 反应 9.0h， 生成 1-([1,1'-biphenyl]-4-yl)propan-1-ol
  参考文献：
  名称：

  南极假丝酵母脂肪酶B催化的1-联芳基-和1-（吡啶基苯基）烷基-1-醇的动力学拆分

  摘要：

  南极假丝酵母的脂肪酶B （CAL-B）催化一些1-联芳基-2-基-，-3-基和-4-基乙醇和-丙-1-醇的高度对映选择性（E > 200）酯交换，以及1-（o-，m-和对-吡啶基苯基）乙醇6含乙酸乙烯酯，在所有情况下均应遵守Kazlauskas规则。间位和对位取代的底物在数小时内转化（转化率范围为23-50％），丙-1-醇衍生物的反应速率比乙醇衍生物的反应速率慢。邻位酯交换-取代的醇用了几天，并伴有化学酶促副反应：形成了另一种由半缩醛衍生的乙酸酯，其在6和乙醛之间是由乙酸乙烯酯形成的。在乙酸异丙烯酯作为酰基供体的情况下，该副反应被抑制，酯交换反应的转化度在十天后为20-40％（E > 200）。还证明了（R）-6p作为配体在将二乙基锌不对称加成到苯甲醛中的有用性。

  DOI：

  10.1002/adsc.200404330
• 作为产物：
  描述：

  正丙基苯 在 Oxone 、 sodium bromide 作用下， 以 水 、 乙腈 为溶剂， 以86%的产率得到4'-溴苯丙酮
  参考文献：
  名称：

  烷基苯的双氧化/溴化

  摘要：

  在溴化钠和Oxone的存在下，一系列烷基苯衍生物被溴化和/或氧化，最多可官能化四个CH键。

  DOI：

  10.1016/j.tetlet.2016.01.062

文献信息

• One-Pot Transformation of Ketoximes into Optically Active Alcohols and Amines by Sequential Action of Laccases and Ketoreductases or ω-Transaminases
  作者：Raquel S. Correia Cordeiro、Nicolás Ríos-Lombardía、Francisco Morís、Robert Kourist、Javier González-Sabín

  DOI：10.1002/cctc.201801900

  日期：2019.2.20

  An enzymatic one‐pot process for asymmetric transformation of prochiral ketoximes into alcohols or amines was developed by sequential coupling of a laccase‐catalyzed deoximation either with a ketone reduction (ketoreductase, KRED) or bioamination (ω‐transaminase, ω‐TA) in aqueous medium. An accurate selection of biocatalysts provided the corresponding products in excellent enantiomeric excesses and

  通过将漆酶催化的脱肟与酮还原（酮还原酶，KRED）或生物胺化（ω-转氨酶，ω-TA）相继偶联，开发了一种酶法一锅法，用于将前手性酮肟不对称转化为醇或胺。中等的。正确选择生物催化剂后，相应的产品的对映体过量非常好，醇的总转化率从83％到> 99％，胺的总转化率从70％到> 99％。同样，仅使用1％（w / w）的Cremophor®（一种聚乙氧基化蓖麻油）作为助溶剂，可使手性醇级联反应中的浓度达到100 mM。
• Application of Silicon-Initiated Water Splitting for the Reduction of Organic Substrates
  作者：Ashot Gevorgyan、Satenik Mkrtchyan、Tatevik Grigoryan、Viktor O. Iaroshenko

  DOI：10.1002/cplu.201800131

  日期：2018.5

  several important classes of organic compounds is described. It is found that the reductive water splitting can be promoted by several metalloids among which silicon shows the best efficiency. The developed methodologies were applied for the reduction of nitro compounds, N-oxides, sulfoxides, alkenes, alkynes, hydrodehalogenation as well as for the gram-scale synthesis of several substrates of industrial

  描述了使用水作为氢的供体，其适合于还原几种重要类别的有机化合物。发现还原水分解可以通过几种准金属来促进，其中硅显示出最佳的效率。所开发的方法学被用于还原硝基化合物，N-氧化物，亚砜，烯烃，炔烃，加氢脱卤作用以及几种工业上具有重要意义的底物的克级合成。
• From a Sequential to a Concurrent Reaction in Aqueous Medium: Ruthenium-Catalyzed Allylic Alcohol Isomerization and Asymmetric Bioreduction
  作者：Nicolás Ríos-Lombardía、Cristian Vidal、Elisa Liardo、Francisco Morís、Joaquín García-Álvarez、Javier González-Sabín

  DOI：10.1002/anie.201601840

  日期：2016.7.18

  The ruthenium‐catalyzed redox isomerization of allylic alcohols was successfully coupled with the enantioselective enzymatic ketone reduction (mediated by KREDs) in a concurrent process in aqueous medium. The overall transformation, formally the asymmetric reduction of allylic alcohols, took place with excellent conversions and enantioselectivities, under mild reaction conditions, employing commercially

  在水性介质中同时进行的钌催化的烯丙醇氧化还原异构化与对映选择性酶酮还原（由KRED介导）成功地结合在一起。在温和的反应条件下，采用可商购和容易获得的催化体系，并且没有外部辅酶或辅因子，总转化，即烯丙基醇的不对称还原，以优异的转化率和对映选择性进行。优化导致了多步骤方法和真正的级联反应，其中金属催化剂和生物催化剂从一开始就共存。
• Copper catalyzed oxygen assisted C(CNOH)–C(alkyl) bond cleavage: a facile conversion of aryl/aralkyl/vinyl ketones to aromatic acids
  作者：Pochampalli Sathyanarayana、Owk Ravi、Prathap Reddy Muktapuram、Surendar Reddy Bathula

  DOI：10.1039/c5ob01569c

  日期：——

  A novel copper-catalyzed aerobic oxidative C(NOH)–C(alkyl) bond cleavage reaction of aryl/aralkyl/vinyl ketones for the synthesis of aromatic/acrylic acids is described. A series of ketones having aryl/aralkyl/vinyl at the one end and methyl to any higher alkyl at the other end can be selectively cleaved and converted into the corresponding acids via oxime intermediates.

  描述了一种新型的铜催化的芳基/芳烷基/乙烯基酮的需氧氧化C（NOH）-C（烷基）键裂解反应，用于合成芳族/丙烯酸。可以选择性地裂解在一端具有芳基/芳烷基/乙烯基而在另一端具有甲基至任何高级烷基的一系列酮，并通过肟中间体将其转化为相应的酸。
• α-羟基酮化合物的廉价高效合成方法
  申请人：北京大学

  公开号：CN104710256B

  公开（公告）日：2017-03-22

  本发明公开了一种α‑羟基酮化合物的廉价高效合成方法。该合成方法包括：在常压条件下，以碘单质、N‑溴代丁二酰亚胺、溴化铜、溴单质、溴化氢、N‑碘代丁二酰亚胺或碘化氢作为催化剂，以亚砜为氧化剂，以水或亚砜为羟基源，以亚砜，乙酸乙酯、N,N‑二甲基甲酰胺、乙腈、甲苯、1,4‑二氧六环、1,2‑二氯乙烷、四氢呋喃或H2O为溶剂，与羰基化合物混合于10‑120℃温度下进行氧化羟基化反应即可将羰基化合物高选择性的转化为α‑羟基酮化合物。本发明方法与传统合成方法相比具有操作简单，收率高，条件简单，易于纯化，废弃物排放量少，反应设备简单，易于工业化生产等诸多优点。本发明的方法具有广泛地适用性，能够用于多种α‑羟基酮化合物的合成。

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