2-氯-4'-羟基苯乙酮 | 6305-04-0

• 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 - 有机氧化合物
• 中文名称: 2-氯-4'-羟基苯乙酮
• 中文别名: 2-氯-4’-羟基苯乙酮；-氯代对羟基苯乙酮
• 英文名称: p-hydroxyphenacyl chloride
• 英文别名: α-chloro-4-hydroxyacetophenone；2-chloro-4'-hydroxyacetophenone；4-hydroxyphenyl chloromethyl ketone；2-Chloro-1-(4-hydroxyphenyl)ethanone
• CAS: 6305-04-0
• 化学式: C₈H₇ClO₂
• mdl: MFCD00229893
• 分子量: 170.595
• InChiKey: PPPIAEPDQPCIIM-UHFFFAOYSA-N

物化性质

• 熔点：
  145-146 °C
• 沸点：
  241.44°C (rough estimate)
• 密度：
  1.2315 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2914700090

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 2-Chloro-1-(4-hydroxyphenyl)ethan-1-one
CAS-No. : 6305-04-0
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Acute toxicity, Oral (Category 3)
Skin corrosion (Category 1B)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed. Causes burns.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Danger
Hazard statement(s)
H301 Toxic if swallowed.
H314 Causes severe skin burns and eye damage.
Precautionary statement(s)
P280 Wear protective gloves/ protective clothing/ eye protection/ face
protection.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
P310 Immediately call a POISON CENTER or doctor/ physician.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R22 Harmful if swallowed.
R34 Causes burns.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36/37/39 Wear suitable protective clothing, gloves and eye/face protection.
S45 In case of accident or if you feel unwell, seek medical advice immediately
(show the label where possible).
Other hazards
Lachrymator.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C8H7ClO2
Molecular Weight : 170,6 g/mol
Component Concentration
2-Chloro-1-(4-hydroxyphenyl)ethan-1-one
CAS-No. 6305-04-0 -
EC-No. 228-613-0

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Take off contaminated clothing and shoes immediately. Wash off with soap and plenty of water. Take
victim immediately to hospital. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Do NOT induce vomiting. Never give anything by mouth to an unconscious person. Rinse mouth with
water. Consult a physician.
Most important symptoms and effects, both acute and delayed
Material is extremely destructive to tissue of the mucous membranes and upper respiratory tract, eyes, and
skin., Cough, Shortness of breath, Headache, Nausea
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Hydrogen chloride gas
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate
ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling
the product.
Personal protective equipment
Eye/face protection
Face shield and safety glasses Use equipment for eye protection tested and approved under
appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face particle
respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering
controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use
respirators and components tested and approved under appropriate government standards such
as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
LD50 Oral - rat - 230 mg/kg
Remarks: Sense Organs and Special Senses (Nose, Eye, Ear, and Taste):Eye:Lacrimation.
Behavioral:Somnolence (general depressed activity). Diarrhoea
LD50 Dermal - rabbit - > 8.000 mg/kg
Skin corrosion/irritation
Skin - rabbit - Severe skin irritation
Serious eye damage/eye irritation
Eyes - rabbit - Severe eye irritation
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Material is extremely destructive to the tissue of
the mucous membranes and upper respiratory tract.
Ingestion Toxic if swallowed. Causes burns.
Skin May be harmful if absorbed through skin. Causes skin burns.
Eyes Causes eye burns.
Signs and Symptoms of Exposure
Material is extremely destructive to tissue of the mucous membranes and upper respiratory tract, eyes, and
skin., Cough, Shortness of breath, Headache, Nausea
Additional Information
RTECS: KM5579000

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: 2928 IMDG: 2928 IATA: 2928
UN proper shipping name
ADR/RID: TOXIC SOLID, CORROSIVE, ORGANIC, N.O.S. (2-Chloro-1-(4-hydroxyphenyl)ethan-1-one)
IMDG: TOXIC SOLID, CORROSIVE, ORGANIC, N.O.S. (2-Chloro-1-(4-hydroxyphenyl)ethan-1-one)
IATA: Toxic solid, corrosive, organic, n.o.s. (2-Chloro-1-(4-hydroxyphenyl)ethan-1-one)
Transport hazard class(es)
ADR/RID: 6.1 (8) IMDG: 6.1 (8) IATA: 6.1 (8)
Packaging group
ADR/RID: II IMDG: II IATA: II
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

应用广泛，2-氯-4'-羟基苯乙酮可用作有机中间体和医药中间体，主要应用于实验室研发及化工生产过程。

反应信息

• 作为反应物：
  描述：

  2-氯-4'-羟基苯乙酮 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 25.0 ℃ 、310.27 kPa 条件下， 反应 28.0h， 生成 4-(2-甲氧基乙基)苯酚
  参考文献：
  名称：

  Gurjar, M.K.; Joshi, Shreerang V; Sastry, B.S., Synthetic Communications, 1990, vol. 20, # 22, p. 3489 - 3496

  摘要：

  DOI：
• 作为产物：
  描述：

  对羟基苯乙酮 在 盐酸 、 硝酸铵 、 碘 、 氧气 作用下， 以 水 、 乙腈 为溶剂， 反应 22.0h， 以64%的产率得到2-氯-4'-羟基苯乙酮
  参考文献：
  名称：

  好氧氧化条件下芳基甲基酮的α-氯化反应

  摘要：

  新型反应体系：空气/硝酸铵/碘/盐酸[空气/ NH 4 NO 3（类别） / I 2（类别）[/ HCl]是一种简单，安全，便宜，高效且区域选择性的介体，用于在好氧氧化条件下对芳基，杂芳基和烷基甲基酮进行α-氯化。本发明对催化量碘的使用使得能够对各种甲基酮衍生物的全面范围进行适度到定量的区域选择性氯化，所述甲基酮衍生物包括带有可氧化的杂原子（S，N）取代基的那些，其中一些具有已宣布的潜在的生物学和药学活性。空气中的氧气在略微超压下起着终端氧化剂的作用，该终端氧化剂被催化量的硝酸铵（NH 4 NO 3）释放的氮氧化物的氧化还原循环催化活化）在盐酸（HCl）的酸性条件下并由元素碘（I 2）共同催化，这对于反应体系的高效率至关重要。

  DOI：

  10.1002/adsc.201301012

文献信息

• High-throughput screen for inhibitors of protein–protein interactions in a reconstituted heat shock protein 70 (Hsp70) complex
  作者：Isabelle R. Taylor、Bryan M. Dunyak、Tomoko Komiyama、Hao Shao、Xu Ran、Victoria A. Assimon、Chakrapani Kalyanaraman、Jennifer N. Rauch、Matthew P. Jacobson、Erik R.P. Zuiderweg、Jason E. Gestwicki

  DOI：10.1074/jbc.ra117.001575

  日期：2018.3

  multiprotein complexes (RMPCs). As a model system, we chose heat shock protein 70 (Hsp70), which is an ATP-dependent molecular chaperone that interacts with co-chaperones, including DnaJA2 and BAG2. The PPIs between Hsp70 and its co-chaperones stimulate nucleotide cycling. Thus, to re-create this ternary protein system, we combined purified human Hsp70 with DnaJA2 and BAG2 and then screened 100,000 diverse

  蛋白质间相互作用（PPI）是推定药物靶标的重要类别。高通量筛选（HTS）的改进显着加速了某些PPI抑制剂的发现。然而，适用于筛选多蛋白复合物的方法（例如由三种或更多种不同成分组成的复合物）的出现较慢。在这里，我们探索了一种使用重组多蛋白复合物（RMPC）的方法。作为模型系统，我们选择了热激蛋白70（Hsp70），它是一种ATP依赖性分子伴侣，可与包括DnaJA2和BAG2在内的伴侣伴侣相互作用。Hsp70及其协同分子之间的PPI刺激核苷酸循环。因此，为了重新创建此三元蛋白质系统，我们将纯化的人Hsp70与DnaJA2和BAG2结合在一起，然后进行了100次筛选，000种化合物，可抑制伴侣伴侣刺激的ATPase活性。这项HTS运动产生了两种具有有希望的抑制活性的化合物。有趣的是，一种抑制Hsp70和DnaJA2之间的PPI，而另一种似乎抑制Hsp70-BAG2复合体。使用二级分析，我们发现这
• α-Chlorination of Aromatic Acetyl Derivatives with Benzyltrimethylammonium Dichloroiodate
  作者：Shoji Kajigaeshi、Takaaki Kakinami、Masayuki Moriwaki、Shizuo Fujisaki、Kimihiro Maeno、Tsuyoshi Okamoto

  DOI：10.1055/s-1988-27633

  日期：——

  Reaction of aromatic acetyl derivatives with benzyltrimethylammonium dichloroiodate in refluxing dichloroethane/methanol for several hours gave α-chloroacetyl derivatives in good yields.

  在回流二氯乙烷/甲醇中，芳香族乙酰衍生物与苄基三甲基二氯碘酸铵反应数小时，可获得高产率的α-氯乙酰衍生物。
• Media controlled photo-Favorskii type rearrangement of α-chloro acetophenones: Synthesis of phenylacetic acids
  作者：Dilip D. Dhavale、Vasant P. Mali、Surendra G. Sudrik、Harikisan R. Sonawane

  DOI：10.1016/s0040-4020(97)10081-3

  日期：1997.12

  Photolysis of substituted α-chloro acetophenones has been studied in different solvent systems wherein 1,2-aryl migration is found to be media controlled. Effect of substituents on the migratory aptitude and a direct access to phenylacetic acids, in practical yields, has been described.

  已经在不同的溶剂系统中研究了取代的α-氯乙酰苯的光解，其中发现1,2-芳基迁移受介质控制。已经描述了取代基对迁移能力和以实际产率直接获得苯乙酸的影响。
• Novel anthelmintic and insecticidal compositions
  申请人：——

  公开号：US20040171650A1

  公开（公告）日：2004-09-02

  The present invention relates to novel anthelmintic and insecticidal compositions in general, and, more specifically, compositions containing triazole derivatives as active ingredients.

  本发明涉及一般的新的驱虫和杀虫组合物，更具体地说，是含有三唑衍生物作为活性成分的组合物。
• Synthesis and biological evaluation of 3,6-diaryl-7H-thiazolo[3,2-b] [1,2,4]triazin-7-one derivatives as acetylcholinesterase inhibitors
  作者：Zhe Jin、Liu Yang、Si-Jie Liu、Jian Wang、Shuo Li、Huang-Quan Lin、David Chi Cheong Wan、Chun Hu

  DOI：10.1007/s12272-010-1013-8

  日期：2010.10

  Acetylcholinesterase (AChE) inhibitors played an important role in developing a cure for Alzheimer’ s disease. In order to study on the influence of modifications at different groups and side chains on the AChE inhibitory ability and the active sites of 7H-thiazolo[3,2-b][1,2,4]triazin-7-one derivatives, fourteen 3,6-diaryl-7H-thiazolo[3,2-b][1,2,4]triazin-7-one derivatives were designed and synthesized. The study of AChE inhibitory activity was carried out using the Ellman colorimetric assay with huperzine-A as the positive control drug. Most of the target compounds exhibited more than 50% inhibition at 10 μM. Some target compounds showed strong inhibition against AChE. The molecular fields analysis and preliminary structureactivity relationships are discussed.

  乙酰胆碱酯酶(AChE)抑制剂在开发阿尔茨海默病的治疗方法中扮演了重要角色。为了研究不同基团和侧链修饰对7H-噻唑并[3,2-b][1,2,4]三嗪-7-酮衍生物的AChE抑制能力和活性部位的影响，设计并合成了十四个3,6-二芳基-7H-噻唑并[3,2-b][1,2,4]三嗪-7-酮衍生物。使用Ellman比色法以石杉碱甲作为阳性对照药物进行了AChE抑制活性的研究。大多数目标化合物在10 μM下表现出超过50%的抑制作用。某些目标化合物显示出对AChE的强烈抑制作用。讨论了分子场分析和初步的构效关系。

表征谱图