4-乙酰氧基苄醇 | 6309-46-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: 4-乙酰氧基苄醇
• 英文名称: 4-acetoxybenzyl alcohol
• 英文别名: 4-(hydroxymethyl)phenyl acetate；p-acetoxybenzyl alcohol；4-acetyloxybenzyl alcohol；para-acetoxybenzyl alcohol；p-(acetyloxy)benzyl alcohol；[4-(hydroxymethyl)phenyl] acetate
• CAS: 6309-46-2
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: FKMVNGWJGSSDCF-UHFFFAOYSA-N

物化性质

• 熔点：
  37-42℃
• 沸点：
  110℃ (0.001 Torr)
• 密度：
  1.169g/mLat 25℃
• 闪点：
  >110°C

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P261,P272,P273,P280,P302+P352,P312,P321,P333+P313,P363,P501
• 危险性描述：
  H303,H317,H402
• 储存条件：
  2-8°C

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 4-Acetoxybenzyl alcohol
CAS-No. : 6309-46-2
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]
Skin sensitization (Category 1)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
May cause sensitization by skin contact.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H317 May cause an allergic skin reaction.
Precautionary statement(s)
P280 Wear protective gloves.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R43 May cause sensitization by skin contact.
S-phrase(s)
S36/37 Wear suitable protective clothing and gloves.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : 4-(Hydroxymethyl)phenyl acetate
4-(Acetyloxy)benzenemethanol
Formula : C9H10O3
Molecular Weight : 166,17 g/mol
Component Concentration
4-Acetoxybenzyl alcohol
CAS-No. 6309-46-2 -

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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
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
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
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
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
no data available
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
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the
environment must be avoided.
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.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: 2 - 8 °C
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
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
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
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
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 37 - 42 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point > 110 °C - closed cup
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 1,169 g/cm3 at 25 °C
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 0,859
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
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
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. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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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
Harmful to aquatic life.
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. 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: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
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

反应信息

• 作为反应物：
  描述：

  4-乙酰氧基苄醇 在 β-环糊精 、 2-碘酰基苯甲酸 作用下， 以 水 、 丙酮 为溶剂， 反应 8.0h， 以98%的产率得到对羟基苯甲醛
  参考文献：
  名称：

  水中的小β-环糊精/ IBX：高度仿生的一锅式仿制THP / MOM / Ac / Ts醚去保护，并伴随查尔酮环氧化物的氧化裂解和醇的氧化脱氢

  摘要：

  对THP / MOM / Ac / Ts醚进行温和有效的一锅脱保护，并进行环氧化物的氧化裂解和醇的氧化脱氢反应，形成[小β-羟基1，2，2二酮，1,2,3三酮...

  DOI：

  10.1039/c5gc01785h
• 作为产物：
  描述：

  对羟基苯甲醇 在 咪唑 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 4-乙酰氧基苄醇
  参考文献：
  名称：

  Stimuli‐Responsive PROTACs for Controlled Protein Degradation

  摘要：

  摘要 蛋白质溶解靶向嵌合体（PROTACs）是一种很有前景的治疗方法，可用于解决药物发现过程中不可药用和耐药的问题。然而，潜在的靶向毒性在临床上仍具有挑战性。我们开发了一种通用笼化策略，合成了一系列刺激响应型 PROTACs（sr-PROTACs），它们具有不同的分子模块，带有坚固且可裂解的连接体，在操纵蛋白质降解方面具有 "开启 "功能。通过利用病理线索（如高浓度 ROS、磷酸酶、H2S 或缺氧）和外部触发器（如紫外线、X 射线或生物正交试剂），我们通过去钙化和随后的自惰性裂解实现了原始 PROTACs 的特定位点激活和无痕释放，实现了体外选择性吸收和可控蛋白质降解。体内研究发现，两种含磷酸和氟笼的 sr-PROTACs 具有高溶解度和长时间血浆暴露的特点，能被肿瘤过表达的磷酸酶或低剂量的 X 射线原位照射特异性激活，从而导致高效的蛋白质降解和强效的肿瘤缓解。随着临床实践中更多反应性生物标记物的筛选，我们的笼式库可为设计可激活的 PROTACs、原药、抗体-药物共轭物和智能生物材料提供通用工具，用于个性化治疗、组织工程或再生医学。

  DOI：

  10.1002/anie.202306824

文献信息

• Friedel-Crafts Reaction of Benzyl Fluorides: Selective Activation of CF Bonds as Enabled by Hydrogen Bonding
  作者：Pier Alexandre Champagne、Yasmine Benhassine、Justine Desroches、Jean-François Paquin

  DOI：10.1002/anie.201406088

  日期：2014.12.8

  Friedel–Crafts benzylation of arenes with benzyl fluorides has been developed. The reaction produces 1,1‐diaryl alkanes in good yield under mild conditions without the need for a transition metal or a strong Lewis acid. A mechanism involving activation of the CF bond through hydrogen bonding is proposed. This mode of activation enables the selective reaction of benzylic CF bonds in the presence of other benzylic

  已经开发了用苄基氟化物进行芳烃的弗里德尔-克拉夫茨苄基化反应。在温和的条件下，该反应可高收率地生成1,1-二芳基烷烃，而无需过渡金属或强路易斯酸。提出了一种通过氢键激活CF键的机理。这种活化方式能够在存在其他苄基离去基团的情况下使苄基CF键选择性反应。
• [EN] COMPOUNDS USEFUL IN THE TREATMENT OF NEOPLASTIC DISEASES<br/>[FR] COMPOSÉS UTILES DANS LE TRAITEMENT DE MALADIES NÉOPLASIQUES
  申请人：UNIVERSITÄT ZU KÖLN

  公开号：WO2015044177A1

  公开（公告）日：2015-04-02

  The present invention refers to compounds of formula: (formula A), wherein R1 is selected from (formula I), (formula II), (formula (III), (formula IV), (formula V), or (formula B), and wherein R2, R3, R4 and R5 are as defined in the claims and X is OTBS, hydroxy, formyloxy, acetoxy, nitrooxy, nitrooxymethyl, or a halogen; and pharmaceutically acceptable salts thereof, which are useful in the treatment of neoplastic or proliferative disorders, a pharmaceutical composition comprising such a compound and a method preparing this compound.

  本发明涉及以下式的化合物：（式A），其中R1从（式I），（式II），（式III），（式IV），（式V）或（式B）中选择，并且其中R2，R3，R4和R5如权利要求中定义的那样，X为OTBS，羟基，甲酰氧基，乙酰氧基，硝基氧基，硝基甲氧基或卤素；及其药学上可接受的盐，用于治疗肿瘤性或增生性疾病，包括这种化合物的药物组合物和制备该化合物的方法。
• A Highly Chemoselective and Rapid Chlorination of Benzyl Alcohols under Neutral Conditions
  作者：Chunbao Li、Lili Sun、Guisheng Peng、Hongmei Niu、Qiang Wang

  DOI：10.1055/s-0028-1083243

  日期：2008.12

  A rapid and highly selective chlorination method has been developedusing 2,4,6-trichloro-1,3,5-triazine (TCT) catalyzed by dimethylsulfoxide. The reactions take 10 to 40 minutes, and the yields arealmost quantitative. The neutral reaction conditions are compatiblewith substrates bearing acid-labile functional groups. Both competitiveintramolecular and intermolecular reactions for benzyl alcoholsin

  使用二甲亚砜催化的 2,4,6-三氯-1,3,5-三嗪 (TCT) 开发了一种快速、高选择性的氯化方法。反应需要 10 到 40 分钟，产率几乎是定量的。中性反应条件与带有酸不稳定官能团的底物相容。苯甲醇在脂肪醇存在下的竞争性分子内和分子间反应均表明其选择性很高。该方法已成功用于临床上使用的神经药物天麻素的选择性氯化。该程序代表了有机和药物化学中一种有用的新工具。
• Redox-Selective Generation of Aldehydes and H₂from Alcohols under Visible Light
  作者：Zijun Liu、Joaquim Caner、Akihiko Kudo、Hiroshi Naka、Susumu Saito

  DOI：10.1002/chem.201301347

  日期：2013.7.15

  Photosynthetic dehydrogenation: Potential usefulness of visible‐light‐induced dehydrogenation of alcohols in organic synthesis was demonstrated, in which aldehydes and H2 were afforded by using Ru/SrTiO3:Rh and water (see scheme). Water was essential for the reaction. High efficiency (TON: up to 15 400 based on Rh; H2 and aldehyde evenly generated) and high selectivity were achieved.

  光合脱氢：证明了可见光诱导的醇在有机合成中的潜在用途，其中通过使用Ru / SrTiO 3：Rh和水提供醛和H 2（请参见方案）。水对于反应是必不可少的。获得了高效率（TON：基于Rh最高可达15400； H 2和醛均匀生成）和高选择性。
• [EN] INHIBITORS OF HUMAN ATGL<br/>[FR] INHIBITEURS DE L'ATGL HUMAIN
  申请人：KARL FRANZENS UNIV GRAZ

  公开号：WO2021019051A1

  公开（公告）日：2021-02-04

  The present invention relates to novel inhibitors of adipose triglyceride lipase (ATGL) having an improved inhibitory activity against human ATGL (hATGL) as well as pharmaceutical compositions comprising these inhibitors, and their therapeutic use, particularly in the treatment or prevention of a lipid metabolism disorder, including, e.g., obesity, non-alcoholic fatty liver disease, type 2 diabetes, insulin resistance, glucose intolerance, hypertriglyceridemia, metabolic syndrome, cardiac and skeletal muscle steatosis, congenital generalized lipodystrophy, familial partial lipodystrophy, acquired lipodystrophy syndrome, atherosclerosis, or heart failure.

  本发明涉及新型抑制脂肪甘油三酯脂肪酶（ATGL）的抑制剂，其对人类ATGL（hATGL）具有改善的抑制活性，以及包含这些抑制剂的药物组合物，及其治疗用途，特别是在治疗或预防脂质代谢紊乱方面的用途，包括例如肥胖、非酒精性脂肪肝病、2型糖尿病、胰岛素抵抗、葡萄糖不耐症、高甘油三酯血症、代谢综合征、心脏和骨骼肌脂肪变性、先天性全身性脂肪营养不良、家族性部分脂肪营养不良、获得性脂肪营养不良综合征、动脉粥样硬化或心力衰竭。