三氯生甲酯 | 4640-01-1

• 物质功能分类: 分析化学 - 标准品 - 化妆品标准品
• 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: 三氯生甲酯
• 中文别名: 三氯生甲基；2,4,4'-三氯-2'-羟基二苯醚甲酯
• 英文名称: 2,4-dichloro-1-(4-chloro-2-methoxyphenoxy)benzene
• 英文别名: 4-chloro-1-[2,4-dichlorophenoxy]-2-methoxybenzene；2,4,4'-trichloro-2'-methoxydiphenyl ether；5-chloro-2-(2',4'-dichlorophenoxy)anisole；5-chloro-2-(2,4-dichlorophenoxy)anisole；triclosan methyl ester；methyl triclosan
• CAS: 4640-01-1
• 化学式: C₁₃H₉Cl₃O₂
• 分子量: 303.572
• InChiKey: NLYDHBBTVWMLFD-UHFFFAOYSA-N

物化性质

• 熔点：
  210-217 °C
• 沸点：
  210-217 °C
• 密度：
  1.380±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（轻微）、乙酸乙酯（轻微、加热）、甲醇（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  N
• 安全说明：
  S60,S61
• 危险类别码：
  R50/53
• 海关编码：
  2909309090
• WGK Germany：
  3
• 危险品运输编号：
  UN 3082 9/PG 3
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  | 冰箱 |

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Triclosan-methyl
CAS-No. : 4640-01-1
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 aquatic toxicity (Category 1)
Chronic aquatic toxicity (Category 1)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H410 Very toxic to aquatic life with long lasting effects.
Precautionary statement(s)
P273 Avoid release to the environment.
P501 Dispose of contents/ container to an approved waste disposal plant.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R50/53 Very toxic to aquatic organisms, may cause long-term adverse effects in
the aquatic environment.
S-phrase(s)
S60 This material and its container must be disposed of as hazardous waste.
S61 Avoid release to the environment. Refer to special instructions/ Safety
data sheets.
Caution - substance not yet tested completely.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : Methyl triclosan
5-Chloro-2-(2,4-dichlorophenoxy)anisole
2,4,4′-Trichloro-2′-methoxydiphenyl ether
Formula : C13H9Cl3O2
Molecular Weight : 303,57 g/mol
Component Concentration
4-Chloro-1-(2,4-dichlorophenoxy)-2-methoxybenzene
CAS-No. 4640-01-1 -

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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
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
Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation.
Evacuate personnel to safe areas.
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
Soak up with inert absorbent material and dispose of as hazardous waste. 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
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. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Specific end use(s)
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
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
impervious clothing, 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 respirator
with multi-purpose combination (US) or type ABEK (EN 14387) 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: liquid
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- log Pow: 5,269
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
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
Prolonged or repeated exposure may cause allergic reactions in certain sensitive individuals.
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
Very toxic to aquatic life.

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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.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: 3082 IMDG: 3082 IATA: 3082
UN proper shipping name
ADR/RID: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, LIQUID, N.O.S. (4-Chloro-1-(2,4-
dichlorophenoxy)-2-methoxybenzene)
IMDG: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, LIQUID, N.O.S. (4-Chloro-1-(2,4-
dichlorophenoxy)-2-methoxybenzene)
IATA: Environmentally hazardous substance, liquid, n.o.s. (4-Chloro-1-(2,4-dichlorophenoxy)-2-
methoxybenzene)
Transport hazard class(es)
ADR/RID: 9 IMDG: 9 IATA: 9
Packaging group
ADR/RID: III IMDG: III IATA: III
Environmental hazards
ADR/RID: yes IMDG Marine Pollutant: yes IATA: yes
Special precautions for user
Further information
EHS-Mark required (ADR 2.2.9.1.10, IMDG code 2.10.3) for single packagings and combination
packagings containing inner packagings with Dangerous Goods > 5L for liquids or > 5kg for solids.

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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
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 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.

制备方法与用途

用途

三氯生甲酯可用作制备2,4,4'-三氯-2'-羟基二苯醚的中间体，广泛用于肥皂和化妆品作为杀菌剂，并以通用名Triclosan闻名。

制备

从商业上引入之时，三氯生甲酯是通过以下方法制备的：将2,4,4'-三氯-2'-氨基二苯醚与亚硝酰基硫酸重氮化，然后将所得的硫酸氢二重氮盐与热的强硫酸反应。

生物活性

Triclosan-methyl 是 Triclosan 的转化产物。Triclosan 是个人护理产品（如牙膏、洗发水和肥皂）中的杀菌剂，同时也是多种洗涤剂和化妆品中的稳定剂。

反应信息

• 作为反应物：
  描述：

  三氯生甲酯 在 indium(III) triflate 、 5-methyl-1,3 dinitropyrazole 作用下， 反应 16.0h， 以37%的产率得到1-chloro-4-(2,4-dichlorophenoxy)-5-methoxy-2-nitrobenzene
  参考文献：
  名称：

  从N-H硝化到可控芳烃单硝化和二硝化——多功能高效N-硝基吡唑硝化试剂的发现

  摘要：

  硝基芳烃是非常有价值的有机化合物，长期以来被用作药物、农用化学品和炸药以及多种化学品的重要中间体。因此，芳香硝化的探索已成为学术界和工业界的一项重要工作。在此，我们报告了从N使用实用的 N-H 硝化方法构建的硝基型试剂库。这种硝化试剂可作为硝鎓离子的可控来源，能够对具有良好官能团耐受性的多种（杂）芳烃进行温和且可扩展的硝化。值得注意的是，我们的硝化方法可以通过操纵反应条件来控制，以选择性地提供单硝化或二硝化产物。这种方法在药物化学中的价值已经通过其对复杂生物相关分子的高效后期 C-H 硝化而得到了很好的证实。密度泛函理论 (DFT) 计算和初步机理研究表明，这种硝化试剂的强大功能和多功能性是由于协同的“硝基效应”和“甲基效应”。

  DOI：

  10.1021/jacsau.2c00413
• 作为产物：
  描述：

  三氯生 生成 三氯生甲酯
  参考文献：
  名称：

  通过气相色谱质谱法鉴定羟基化的氯二苯并-对-二恶英，氯二苯并呋喃，氯二苯醚和氯萘为甲基醚。

  摘要：

  合成了代表所有不同羟基取代基的许多羟基化（聚）氯二苯并-对-二恶英，氯二苯并呋喃，氯二苯醚和氯萘的甲基醚，并对其质谱进行了研究。除了氯二苯并呋喃的甲氧基衍生物外，似乎每一类化合物的结构异构体的质量碎裂模式都是非常特异性的，并且可以明确分配分子中甲氧基的位置。可以根据导致稳定的电荷离域（oxonium）离子的合理机理来解释不同的碎裂模式。由于其诊断价值，该方法可用于阐明氯二苯并-对-二恶英的纯异构体的羟基化代谢物的结构，

  DOI：

  10.1002/bms.1200050311

文献信息

• Novel diaryl ureas with efficacy in a mouse model of malaria
  作者：John W. Anderson、Dimitri Sarantakis、Jacek Terpinski、T.R. Santha Kumar、Han-Chun Tsai、Mack Kuo、Arba L. Ager、William R. Jacobs、Guy A. Schiehser、Sean Ekins、James C. Sacchettini、David P. Jacobus、David A. Fidock、Joel S. Freundlich

  DOI：10.1016/j.bmcl.2012.12.022

  日期：2013.2

  Exploration of triclosan analogs has led to novel diaryl ureas with significant potency against in vitro cultures of drug-resistant and drug-sensitive strains of the human malaria parasite Plasmodium falciparum. Compound 18 demonstrated EC50 values of 37 and 55 nM versus in vitro cultured parasite strains and promising in vivo efficacy in a Plasmodium berghei antimalarial mouse model, with >50% survival at

  对三氯生类似物的探索导致新型二芳基脲对人类疟疾寄生虫恶性疟原虫的耐药和药物敏感菌株的体外培养具有显着的效力。与体外培养的寄生虫菌株相比，化合物18的EC 50值为 37 和 55 nM，并且在伯氏疟原虫抗疟小鼠模型中具有良好的体内功效，当以 256 mg/kg 皮下给药时，在治疗后第 31 天存活率 >50%。这一系列化合物提供了一种新颖结构的化学支架，经化学信息学分析验证，可用于抗疟药物发现工作。
• Determination of Triclosan as Its Pentafluorobenzoyl Ester in Human Plasma and Milk Using Electron Capture Negative Ionization Mass Spectrometry
  作者：Mats Allmyr、Michael S. McLachlan、Gunilla Sandborgh-Englund、Margaretha Adolfsson-Erici

  DOI：10.1021/ac060666x

  日期：2006.9.1

  A sensitive method for the determination of triclosan in plasma and milk is presented. Following hydrolysis of possible conjugates, triclosan is extracted with n-hexane/acetone, partitioned into alcoholic potassium hydroxide, and converted into its pentafluorobenzoyl ester. After sulfuric acid cleanup, sample extracts are analyzed by gas chromatography/electron capture negative ionization mass spectrometry. The limit of quantification was 0.009 ng/g for a 5-g plasma sample and 0.018 ng/g for a 3-g milk sample. The coefficient of variation for the method was 6%. The method was tested on more than 70 human plasma and milk samples, of which all plasma samples and more than half of the milk samples were above the limit of quantification. The presented method has lowered the limit of quantification for triclosan in human matrixes significantly as compared to previous methods and makes possible the analysis of triclosan in humans under normal exposure conditions.

  本文介绍了一种测定血浆和牛奶中三氯生含量的灵敏方法。在水解可能存在的共轭物后，用正己烷/丙酮萃取三氯生，并将其分配到氢氧化钾酒精中，然后转化为五氟苯甲酰基酯。硫酸净化后，样品提取物通过气相色谱/电子捕获负离子质谱法进行分析。5 克血浆样品的定量限为 0.009 纳克/克，3 克牛奶样品的定量限为 0.018 纳克/克。该方法的变异系数为 6%。该方法在 70 多个人体血浆和牛奶样品上进行了测试，其中所有血浆样品和一半以上的牛奶样品都超过了定量限。与以前的方法相比，该方法大大降低了人体基质中三氯生的定量限，使在正常接触条件下分析人体中的三氯生成为可能。
• Occurrence of Methyl Triclosan, a Transformation Product of the Bactericide Triclosan, in Fish from Various Lakes in Switzerland
  作者：Marianne E. Balmer、Thomas Poiger、Christian Droz、Kathrin Romanin、Per-Anders Bergqvist、Markus D. Müller、Hans-Rudolf Buser

  DOI：10.1021/es030068p

  日期：2004.1.1

  bactericide triclosan and methyl triclosan, an environmental transformation product thereof, have been previously detected in lakes and a river in Switzerland. Both compounds are emitted via wastewater treatment plants (WWTPs), with methyl triclosan probably being formed by biological methylation. Passive sampling with semi-permeable membrane devices (SPMDs) showed the presence of methyl triclosan in some

  杀菌剂三氯生和甲基三氯生是其环境转化产物，先前已在瑞士的湖泊和河流中检测到。两种化合物均通过废水处理厂（WWTP）排放，甲基三氯生可能是通过生物甲基化形成的。用半渗透膜装置（SPMD）进行的被动采样显示某些湖泊中存在甲基三氯生，这表明该化合物具有生物蓄积性。在这项研究中，我们报告了瑞士各个湖泊从污水处理厂获得的投入所产生的鱼（白鱼，Coregonus SP .；蟑螂，Rutilus rut​​ilus）中存在甲基三氯生。化合物的鉴定基于包括MS / MS数据在内的质谱（MS）证据。鱼类中甲基三氯生的浓度以湿重计最高为35 ng g（-1），以脂质计最高为365 ng g（-1），来自同一湖的鱼的浓度相对较窄（Thunersee，4-6 ng g（-1）;Zürichsee，32-62 ng g（-1）;Pfäffikersee，43-56 ng g（-1）; Greifensee，165-365
• Process for the production of 2,4,4'-trichloro-2'-methoxydiphenyl ether
  申请人：——

  公开号：US06133483A1

  公开（公告）日：2000-10-17

  A process is disclosed for the synthesis of 2,4,4'-trichloro-2'-methoxydiphenyl ether, and it's precursor 2,4,4'-trichloro-2'-bromodiphenyl ether, a novel compound.

  本发明揭示了一种合成2,4,4'-三氯-2'-甲氧基二苯醚及其前体2,4,4'-三氯-2'-溴基二苯醚的新化合物的方法。
• 一种三氯生甲酯的制备方法
  申请人：江苏理工学院

  公开号：CN111153775B

  公开（公告）日：2023-04-28