苯戊酮 | 1009-14-9

• 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: 苯戊酮
• 中文别名: 1-苯基-1-戊酮；丁基苯酮；戊苯酮
• 英文名称: phenyl butyl ketone
• 英文别名: valerophenone；Valerophenon；1-phenylpentan-1-one
• CAS: 1009-14-9
• 化学式: C₁₁H₁₄O
• mdl: MFCD00009480
• 分子量: 162.232
• InChiKey: XKGLSKVNOSHTAD-UHFFFAOYSA-N

物化性质

• 熔点：
  -9 °C
• 沸点：
  244-245 °C (lit.)
• 密度：
  0.975 g/mL at 20 °C (lit.)
• 闪点：
  217 °F
• 溶解度：
  可溶于氯仿（少量）、乙酸乙酯（少量）
• LogP：
  2.79
• 物理描述：
  Liquid
• 保留指数：
  1327
• 稳定性/保质期：
  - 在常温常压下保持稳定，应避免与氧化物接触。 - 它存在于烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xi
• 安全说明：
  S22,S24/25
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2914399090
• 危险品运输编号：
  NONH for all modes of transport
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将容器密封保存，并存放在阴凉、干燥处。

SDS

Name:	Valerophenone 98% Material Safety Data Sheet
Synonym:	1-Phenyl-1-Pentanone
CAS:	1009-14-9

Section 1 - Chemical Product MSDS Name:Valerophenone 98% Material Safety Data Sheet
Synonym:1-Phenyl-1-Pentanone

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1009-14-9	Valerophenone	98%	213-767-3

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

---

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.

---

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:

---

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. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam. Use agent most appropriate to extinguish fire.

---

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. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

---

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# 1009-14-9: 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 minimize contact with skin.
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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear light yellow
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 105 - 107 deg C @ 5.00mmHg
Freezing/Melting Point: -9 deg C
Autoignition Temperature: Not applicable.
Flash Point: 102 deg C ( 215.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: .9880g/cm3
Molecular Formula: C11H14O
Molecular Weight: 162.23

---

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

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1009-14-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Valerophenone - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

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

---

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.

---

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.
WGK (Water Danger/Protection)
CAS# 1009-14-9: No information available.
Canada
CAS# 1009-14-9 is listed on Canada's DSL List.
CAS# 1009-14-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1009-14-9 is listed on the TSCA inventory.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

应用
1-苯基-1-戊酮可作为有机合成中间体和医药中间体，在实验室研发及化工医药合成过程中广泛应用。

用途
苯戊酮是一种有机化学试剂，主要用于有机合成。

制备
苯戊酮可通过两种方法制备：一是由苯和正戊酰氯通过傅克反应得到；二是由苯甲酸甲酯通过格氏反应制得。

化学性质
熔点：-9℃
沸点：105-107℃（5mmHg）

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	5-bromo-1-phenyl-1-pentanone	4509-91-5	C11H13BrO	241.128
  5-氯苯戊酮	5-Chloro-1-phenyl-1-pentanone	942-93-8	C11H13ClO	196.677
  1-苯基-1,4-戊二酮	1-phenyl-1,4-pentadione	583-05-1	C11H12O2	176.215
  1-苯基-4-戊烯-1-酮	1-Phenylpent-4-en-1-one	3240-29-7	C11H12O	160.216
  苯丙酮	1-phenyl-propan-1-one	93-55-0	C9H10O	134.178
  ——	3-bromo-1-phenylpentan-1-one	——	C11H13BrO	241.128
  3-羟基-1-苯基戊-1-酮	3-hydroxy-1-phenylpentan-1-one	88704-64-7	C11H14O2	178.231
  4'-溴苯戊酮	4'-bromovalerophenone	7295-44-5	C11H13BrO	241.128
  苯基环丙基甲酮	cyclopropyl phenyl ketone	3481-02-5	C10H10O	146.189
  2-溴-1-苯基-1-戊酮	α-bromovalerophenone	49851-31-2	C11H13BrO	241.128
• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  苯丁酮	butyrophenone	495-40-9	C10H12O	148.205
  1-苯基-1,4-戊二酮	1-phenyl-1,4-pentadione	583-05-1	C11H12O2	176.215
  ——	4-fluoro-1-phenylpentan-1-one	1383116-00-4	C11H13FO	180.222
  1-苯基-4-戊烯-1-酮	1-Phenylpent-4-en-1-one	3240-29-7	C11H12O	160.216
  2-甲基-1-苯基戊-1-酮	2-methyl-1-phenylpentan-1-one	31366-05-9	C12H16O	176.258
  1-苯基戊烷-1,3-二酮	1-Phenyl-1,3-pentanedione	5331-64-6	C11H12O2	176.215
  ——	3-fluoro-1-phenylpentan-1-one	——	C11H13FO	180.222
  ——	3-bromo-1-phenylpentan-1-one	——	C11H13BrO	241.128
  3-羟基-1-苯基己烷-1-酮	3-hydroxy-1-phenylhexan-1-one	57548-41-1	C12H16O2	192.258
  1-苯基戊烷-1,2-二酮	1-phenyl-1,2-pentanedione	20895-66-3	C11H12O2	176.215

反应信息

• 作为反应物：
  描述：

  苯戊酮 在 Jacobsen's catalyst sodium hypochlorite 、 4-苯基吡啶-N-氧化物 、 phosphate buffer 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (S)-(-)-2-hydroxy-1-phenyl-1-pentan-1-one
  参考文献：
  名称：

  （salen）锰（III）络合物将烯醇磷酸酯不对称氧化为α-羟基酮。烯醇磷酸酯的取代方式对氧转移的立体化学的影响

  摘要：

  本文介绍了对各种不同取代的环状（E）和非环状（Z）-烯醇磷酸酯的对映选择性催化氧化的研究。无环（的不对称氧化Ž含有磷酸基团中的烷氧基取代基）烯醇磷酸盐2a中，Ç，ë -克，我和Ĵ和Ž -构型中含有磷酸基团的取代基的芳氧基烯醇磷酸盐2B，d，和^ h，得到光学活性α-羟基酮4a – j具有良好或高对映选择性的相反构型。研究了烯醇磷酸酯取代基的电子和空间效应对氧化的立体选择性的影响。

  DOI：

  10.1016/j.tet.2006.09.100
• 作为产物：
  描述：

  正戊酸 在 三氯化铝 作用下， 生成 苯戊酮
  参考文献：
  名称：

  Williams; Dickert; Krynitsky, Journal of the American Chemical Society, 1941, vol. 63, p. 2511

  摘要：

  DOI：
• 作为试剂：
  描述：

  乙酰乙酸甲酯 、 sodium;hydride 、 正丁基锂 、 、 正己烷 在 crude product 、 乙醚 作用下， 以 苯戊酮 、 四氢呋喃 为溶剂， 反应 16.17h， 以to afford a solid (m.p. 124°-126° C.)的产率得到
  参考文献：
  名称：

  5,6-dihydropyrone derivatives as protease inhibitors and antiviral agents

  摘要：

  本发明涉及新型5,6-二氢吡喃衍生物及相关结构，这些衍生物具有强大的抑制HIV天冬氨酸蛋白酶，从而阻止HIV感染性的作用。5,6-二氢吡喃衍生物可用于开发治疗细菌和病毒感染和疾病，包括艾滋病的治疗方案。本发明还涉及多功能化5,6-二氢吡喃和相关结构的合成方法。

  公开号：

  US05789440A1

文献信息

• Synthesis of Isoquinoline Derivatives via Palladium‐Catalyzed C−H/C−N Bond Activation of <i>N</i> ‐Acyl Hydrazones with <i>α</i> ‐Substituted Vinyl Azides
  作者：Biao Nie、Wanqing Wu、Wei Zeng、Qingyun Ren、Ji Zhang、Yingjun Zhang、Huanfeng Jiang

  DOI：10.1002/adsc.201901394

  日期：2020.3.17

  A palladium‐catalyzed cyclization of N‐acetyl hydrazones with vinyl azides has been developed. Various substituted isoquinolines, including diverse fused isoquinolines can be prepared via this protocol in moderate to good yields. Mechanistic studies suggest that α‐substituted vinyl azide serves as an internal nitrogen source. Also, C−H bond activation and C−N bond cleavage have been realized using

  已经开发了钯催化的乙烯基叠氮化物对N乙酰基hydr的环化反应。可以通过该方案以中等至良好的产率制备各种取代的异喹啉，包括各种稠合的异喹啉。机理研究表明，α-取代的叠氮化乙烯可作为内部氮源。另外，使用作为指导基团已经实现了CH键的活化和CN键的裂解。
• A simple and efficient oxidation of alcohols with ruthenium on carbon
  作者：Shigeki Mori、Masato Takubo、Kazuya Makida、Takayoshi Yanase、Satoka Aoyagi、Tomohiro Maegawa、Yasunari Monguchi、Hironao Sajiki

  DOI：10.1039/b908451g

  日期：——

  A simple, efficient, and environmentally-friendly heterogeneous Ru/C-catalyzed oxidation of secondary and primary alcohols without additives under an atmosphere of oxygen has been established.

  已经建立了在氧气气氛下没有添加剂的简单，有效和环境友好的Ru / C多相Ru / C催化仲醇和伯醇的氧化方法。
• Highly Efficient Redox Isomerization of Allylic Alcohols and Transfer Hydrogenation of Ketones and Aldehydes Catalyzed by Ruthenium Complexes
  作者：Pei Nian Liu、Kun Dong Ju、Chak Po Lau

  DOI：10.1002/adsc.201000667

  日期：2011.2.11

  A dicationic dichloro-bipyridine-ruthenium complex shows very high catalytic activity in redox isomerization of allylic alcohols but a relatively low one in transfer hydrogenation of ketones; surprisingly, the analogous dimethyl-bipyridine-ruthenium complex shows reverse catalytic activities in the two reactions.

  专用的二氯联吡啶-钌配合物在烯丙基醇的氧化还原异构化中显示出很高的催化活性，而在酮的转移氢化中显示出较低的催化活性。令人惊讶地，类似的二甲基-联吡啶-钌配合物在两个反应中显示出反向的催化活性。
• Alcohols for the α-Alkylation of Methyl Ketones and Indirect Aza-Wittig Reaction Promoted by Nickel Nanoparticles
  作者：Francisco Alonso、Paola Riente、Miguel Yus

  DOI：10.1002/ejoc.200800729

  日期：2008.10

  Nickel nanoparticles have been found to activate primary alcohols used for the α-alkylation of ketones or in indirect aza-Wittig reactions. These processes involve hydrogen transfer from the alcohol to the intermediate α,β-unsaturated ketone or imine, respectively. All these reactions are carried out in the absence of any ligand, hydrogen acceptor or base under mild reaction conditions. For the first

  已发现镍纳米粒子可激活用于酮的 α-烷基化或间接 aza-Wittig 反应的伯醇。这些过程分别涉及从醇到中间体 α,β-不饱和酮或亚胺的氢转移。所有这些反应都是在温和的反应条件下在没有任何配体、氢受体或碱的情况下进行的。在这两个反应中，镍首次被用作贵金属基催化剂的潜在替代品。在一些氘化实验的基础上提出了反应机理。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• New method for generation of β-oxido carbenoid via ligand exchange reaction of sulfoxides: A versatile procedure for one-carbon homologation of carbonyl compounds
  作者：Tsuyoshi Satoh、Norifumi Itoh、Kaoru Gengyo、Sae Takada、Naoyuki Asakawa、Yumi Yamani、Koji Yamakawa

  DOI：10.1016/s0040-4020(01)89299-1

  日期：1994.1

  one-carbon homologation of carbonyl compounds is described. The method is based on the rearrangement of β-oxido carbenoid which is generated via the ligand exchange reaction of the sulfinyl group of α-chloro β-hydroxy sulfoxide with tert-butyllithium. Addition of the carbanion of aryl 1-chloroalkyl sulfoxides to carbonyl compounds gave the adducts in good yields. The β-oxido carbenoid rearrangement of the

  描述了一种新的羰基化合物一碳同系化方法。该方法基于通过α-氯β-羟基亚砜的亚磺酰基与叔丁基锂的配体交换反应而产生的β-氧化类胡萝卜素的重排。将芳基1-氯烷基亚砜的碳负离子加到羰基化合物上，以高收率得到加合物。加合物的β-氧化类胡萝卜素重排得到具有α-烷基取代基的一碳同系羰基化合物。衍生自羰基化合物的加合物与氯甲基对甲苯基亚砜的类似反应产生了亚甲基插入的程序。还讨论了β-氧化类胡萝卜素重排的立体化学。

表征谱图