2-(乙酰氧基)-5-氯苯甲酸 | 1734-62-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(乙酰氧基)-5-氯苯甲酸
• 英文名称: 2-acetoxy-5-chloro-benzoic acid
• 英文别名: 2-Acetoxy-5-chlor-benzoesaeure；5-Chlor-2-acetoxy-benzoesaeure；5-chloro-2-acetoxybenzoic acid；2-(Acetyloxy)-5-chlorobenzoic acid；2-acetyloxy-5-chlorobenzoic acid
• CAS: 1734-62-9
• 化学式: C₉H₇ClO₄
• mdl: MFCD00096360
• 分子量: 214.605
• InChiKey: CNWHHQWYXIPHGY-UHFFFAOYSA-N

物化性质

• 熔点：
  148 °C
• 沸点：
  348.7±32.0 °C(Predicted)
• 密度：
  1.416±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2918990090
• WGK Germany：
  3

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 2-(Acetyloxy)-5-Chlorobenzoic Acid
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
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
Acute toxicity, Oral (Category 4), H302
Serious eye damage (Category 1), H318
Skin sensitisation (Category 1), H317
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xn Harmful R22, R41, R43
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Danger
Hazard statement(s)
H302 Harmful if swallowed.
H317 May cause an allergic skin reaction.
H318 Causes serious eye damage.
Precautionary statement(s)
P280 Wear protective gloves/ 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.
Supplemental Hazard none
Statements
Other hazards
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.

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SECTION 3: Composition/information on ingredients
Substances
Molecular weight : 214,61 g/mol
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
2-(Acetyloxy)-5-Chlorobenzoic Acid
Acute Tox. 4; Eye Dam. 1; <= 100 %
Skin Sens. 1; H302, H317,
H318
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
2-(Acetyloxy)-5-Chlorobenzoic Acid
Xn, R22 - R41 - R43 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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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
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
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
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
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
Nature of decomposition products not known.
Advice for firefighters
Wear self-contained breathing apparatus for firefighting 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 vapours, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
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.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Storage class (TRGS 510): Non Combustible Solids
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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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
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).
Control of environmental exposure
Do not let product enter drains.

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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) Auto-ignition 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
Stable under recommended storage conditions.
Possibility of hazardous reactions
No data available
Conditions to avoid
No data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
In the event of fire: see section 5

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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 sensitisation
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
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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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
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.
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. 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
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
No data available
Chemical Safety Assessment
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Acute Tox. Acute toxicity
Eye Dam. Serious eye damage
H302 Harmful if swallowed.
H317 May cause an allergic skin reaction.
H318 Causes serious eye damage.
Skin Sens. Skin sensitisation
Full text of R-phrases referred to under sections 2 and 3
Xn Harmful
R22 Harmful if swallowed.
R41 Risk of serious damage to eyes.
R43 May cause sensitisation by skin contact.
Further information
Copyright 2014 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  2-(乙酰氧基)-5-氯苯甲酸 在 吡啶 、 氯化亚砜 、 水 、 sodium hydroxide 作用下， 反应 8.0h， 生成 7-chloro-2,4-dithioxo-1,2,3,4-tetrahydro-5H-chromeno[2,3-d]pyrimidine-5-one
  参考文献：
  名称：

  Synthesis of novel thiopyrimidines: an investigation of anti-tubercular and antimicrobial activity

  摘要：

  A variety of novel sulfur-containing tricyclic pyrimidine derivatives have been synthesized via the reaction of 2-amino-4-oxo-4H-chromene-3-carbonitriles 3(a-f) with different reagents and characterized by IR, H-1 NMR, C-13 NMR, mass spectrometry and elemental analysis. The anti-tubercular and antimicrobial activities of the synthesized compounds were investigated.[GRAPHICS].

  DOI：

  10.1080/17415993.2010.523894
• 作为产物：
  描述：

  5-氯代水杨酸 、 乙酸酐 在 硫酸 作用下， 反应 0.33h， 生成 2-(乙酰氧基)-5-氯苯甲酸
  参考文献：
  名称：

  杂质对5-X-阿司匹林和5-X-阿司匹林酸酐多晶型（X = Cl，Br，Me）结晶的影响†

  摘要：

  通过从有机溶剂中进行环境蒸发，结晶5-X-阿司匹林（X = Cl，Br）通常会生成X = Cl的多晶型物I和II的混合物，但对于X = Br的多晶型物I。添加5-X-阿司匹林酸酐（5–20 mol％）将导致X = Cl的多晶型物II的唯一产生，而X = Br的多晶型物II的新产生。浆料实验表明，对于X = Cl，多晶型物I转变为多晶型物II，而对于Br，多晶型物II转变为多晶型物I。因此，在结晶过程中加入酸酐显然加速了X = Cl的I→II转化，并抑制了X = Br的II→I转化。5-X-阿司匹林酸酐可以在有机溶剂中加热5-X-阿司匹林或从5-X-水杨酸合成过程中作为副产物生产，因此，在这种合成中加热步骤的持续时间可以改变合成产物的多晶型形式。5-X-阿司匹林酸酐（X = Cl，Br，Me）也是多晶型的。从有机溶剂中结晶出纯净的化合物只会产生多晶型物I，而多晶型物II可以通过加热乙醇 或者

  DOI：

  10.1039/c1ce06065a

文献信息

• On the role of copper and iron in DNA cleavage by ochratoxin A. Structure-activity relationships in metal binding and copper-mediated DNA cleavage
  作者：Jason A Ardus、Ivan G Gillman、Richard A Manderville

  DOI：10.1139/v98-088

  日期：1998.6.1

  Ochratoxin A (OTA, 1: X = Cl) is a fungal carcinogen that facilitates single-strand DNA cleavage and DNA adduction when metabolically activated. To determine if redox-active transition metals induce OTA-mediated DNA damage, we have examined the toxin's ability to bind Cu(II) and Fe(III) in aqueous media and facilitate DNA cleavage in their presence using agarose gel electrophoresis and supercoiled plasmid DNA. Using fluorescence spectroscopy, 1 was found to bind Cu(II) readily at physiological pH, while acidic conditions (pH 2.6) were employed to study Fe(III) binding due to the formation of Fe-oxide precipitates at higher pH values. Structure-activity relationships employing synthetic derivatives of 1 implied that 1 binds both Cu(II) and Fe(III) by its phenolic oxygen, while the carboxylic acid of its phenylalanine moiety binds Cu(II), but does not appear to play a role in Fe(III) coordination at pH 2.6. In terms of metal-mediated DNA cleavage, no role for 1 could be detected in Fe-induced DNA strand scission. With Cu(II), DNA cleavage by the 1:1 copper-bound complex of 1 could only be initiated by addition of a suitable reducing agent (sodium ascorbate). However, 1 was found to facilitate DNA cleavage by the Cu(II) complex of 1,10-phenanthroline (Cu(OP)₂); a prototypical Cu-mediated nuclease system that cleaves DNA upon activation by an external reducing agent. Structure-activity relationships employing analogs lacking the chlorine atom, ochratoxin B (2: X = H), and the lactone (12), indicated that the chlorine atom is essential for activity of the OTA in potentiating DNA cleavage by Cu(OP)₂. The implications of our findings to the genotoxic properties of 1 are discussed.Key words: ochratoxin, DNA cleavage, copper, iron, 1,10-phenanthroline.

  奥克拉毒素A（OTA，1：X = Cl）是一种真菌致癌物质，当在代谢活化时，它促进单链DNA断裂和DNA加合物的形成。为了确定氧化还原活性过渡金属是否诱导OTA介导的DNA损伤，我们研究了毒素在水介质中结合Cu（II）和Fe（III）的能力，并在它们的存在下利用琼脂糖凝胶电泳和超螺旋质粒DNA促进DNA断裂。利用荧光光谱，发现1在生理pH下能够很容易地结合Cu（II），而在酸性条件（pH 2.6）下用于研究Fe（III）结合，因为在较高pH值下会形成Fe-氧化物沉淀。利用1的合成衍生物进行结构活性关系研究表明，1通过其酚氧结合Cu（II）和Fe（III），而其苯丙氨酸部分的羧酸结合Cu（II），但在pH 2.6下似乎不参与Fe（III）的配位。在金属介导的DNA断裂方面，未发现1在Fe诱导的DNA链切断中起作用。对于Cu（II），只有通过添加适当的还原剂（抗坏血酸钠）才能启动1的1：1铜结合复合物引发的DNA断裂。然而，发现1能够通过1,10-邻菲啰啉（Cu（OP）2）的Cu（II）复合物促进DNA断裂；这是一种原型的Cu介导核酸酶系统，只有在外部还原剂的激活下才能切割DNA。通过缺乏氯原子的类似物进行结构活性关系研究，如奥克拉毒素B（2：X = H）和内酯（12），表明氯原子对于OTA在促进Cu（OP）2介导的DNA断裂中的活性是必不可少的。我们的研究结果对于1的遗传毒性特性的影响进行了讨论。关键词：奥克拉毒素，DNA断裂，铜，铁，1,10-邻菲啰啉。
• Reactions of substituted aspirins with amino acids
  作者：Elisa S. Orth、Michelle Medeiros、Bruno S. Souza、Natália B. Caon、Anthony J. Kirby、Faruk Nome

  DOI：10.1002/poc.2971

  日期：2012.11

  Acyl transfers are key reactions in biology and in the laboratory. In biological systems they are involved in energy transport, in the assembly of complex molecules and in the mechanisms of efficient action of many hydrolytic enzymes. We report a mechanistic and calculational study of the selective N‐acylation reactions of amino acids by substituted aspirins, under mild conditions, in water at 25 °C

  酰基转移是生物学和实验室中的关键反应。在生物系统中，它们参与能量传输，复杂分子的组装以及许多水解酶的有效作用机制。我们报告了在温和条件下于25°C的水中通过取代的阿司匹林对氨基酸进行选择性N酰化反应的机理和计算研究。通过核磁共振鉴定反应的乙酰化氨基酸产物，并通过密度泛函理论研究反应步骤。版权所有©2012 John Wiley＆Sons，Ltd.
• Synthesis and Structure−Activity Relationships of Carboxylated Chalcones:  A Novel Series of <i>CysLT</i>₁ (LTD₄) Receptor Antagonists
  作者：Mariël E. Zwaagstra、Hendrik Timmerman、Masahiro Tamura、Tsutomu Tohma、Yasushi Wada、Kazuhiro Onogi、Ming-Qiang Zhang

  DOI：10.1021/jm960628d

  日期：1997.3.1

  The synthesis and CysLT1 antagonistic activities of a new series of 2-, 3-, and 4-(2-quinolinylmethoxy)- and 3- and 4-[2-(2-quinolinyl)ethenyl]-substituted, 2'-, 3'-, 4'-, or 5'-carboxylated chalcones are described. Structure-activity relationship studies indicate a preference for the presence of a negatively charged (acidic) moiety, although in some cases nitrile or ester analogues also exhibit moderate

  一系列新的2-，3-和4-（2-喹啉基甲氧基）-和3-和4- [2-（2-喹啉基）乙烯基]-取代的2'-，3的合成及CysLT1拮抗活性描述了'-，4'-或5'-羧基查耳酮。结构-活性关系研究表明，优选带负电的（酸性）部分，尽管在某些情况下腈或酯类似物也具有中等活性。喹啉部分可以在3-或4-位被取代。用其他芳香族基团取代该杂环会导致化合物具有可比的亲和力[2-（7-氯喹啉），1-（1-甲基-2-苯并咪唑）或1-（2-苯并噻唑）]或具有较低的活性[1 -（1-乙氧基乙基）-2-苯并咪唑，2-萘基或苯基]。喹啉和查耳酮部分可以通过乙烯基或甲氧基间隔基连接。对于3-和4-取代的查耳酮，查耳酮B环上的酸性部分可以连接至2'-，3'-，4'-或5'-位置。没有一般模式可以指定哪个取代位置产生最有效的化合物。该系列包含几种有效的CysLT1受体拮抗剂，其K（D）值接近纳摩尔范围，通过[3H] LTD4
• Novel Short-Step Synthesis of Functionalized γ-Phenyl-β-hydroxybutenoates and their Cyclization to 4-Hydroxycoumarins via the <i>N</i>-Hydroxybenzotriazole Methodology
  作者：Olga Igglessi-Markopoulou、Giorgos Athanasellis、Georgia Melagraki、Haralambos Chatzidakis、Antreas Afantitis、Anastasia Detsi、John Markopoulos

  DOI：10.1055/s-2004-829132

  日期：——

  A novel method for the synthesis of functionalized 3- substituted 4-hydroxycoumarins is reported. C-Acylation com- pounds were derived from the reaction of the N-hydroxybenzotri- azole ester of the functionalized acetyl salicylic acids and a variety of active methylene compounds and cyclized to the title com- pounds. The synthesis is simple and the compounds are produced in yields varying from 39 to

  报道了一种合成功能化3-取代4-羟基香豆素的新方法。C-酰化化合物衍生自官能化乙酰水杨酸的 N-羟基苯并三唑酯与多种活性亚甲基化合物的反应，并环化为标题化合物。合成很简单，化合物的产率从 39% 到 80% 不等。文献中首次通过核磁共振光谱对新制备的 C-酰化化合物的结构进行了深入研究。
• Synthesis of Benz[<i>d</i>]oxazolones Involving Concomitant Acetyl Migration from Oxygen to Nitrogen
  作者：Sibdas Ray、Sukla Ghosh

  DOI：10.1080/00397910903245158

  日期：2010.7.27

  Heating of o-acetoxybenzoyl azides 6–10 in toluene leads to the Curtius reaction, which, when followed by closure of oxazolone ring with concomitant migration of acetyl group from oxygen to nitrogen, produces 3-acetoxybenz[d]oxazol-2(3H)-ones 11–15, which undergo hydrolysis with hot dilute hydrochloric acid to furnish benz[d]oxazol-2(3H)-ones 17–21. Thermal reaction of 2-hydroxy-5-nitrobenzoyl azide

  在甲苯中加热邻乙酰氧基苯甲酰叠氮化物 6-10 导致 Curtius 反应，随后恶唑酮环闭合，同时乙酰基从氧迁移到氮，生成 3-乙酰氧基苯并[d]恶唑-2(3H) -ones 11-15，用热的稀盐酸水解，得到苯并[d]恶唑-2(3H)-ones 17-21。2-羟基-5-硝基苯甲酰叠氮化物 (22) 在甲苯中的热反应最终产生 5-硝基苯并[d]恶唑-2(3H)-酮 (20) 和 5-硝基苯并[d]异恶唑-3(2H)的混合物)-一 (23)。