氯羟吡啶 | 2971-90-6

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 氯羟吡啶
• 中文别名: 二氯二甲吡啶酚；3,5-二氯-2,6-二甲基-4-羟基吡啶；3,5-二氯-2,6-二甲基吡啶-4-酮；氯吡多
• 英文名称: clopidol
• 英文别名: 2,6-dimethyl-3,5-dichloro-4-hydroxypyridine；3,5-Dichloro-2,6-dimethyl-4-pyridinol；3,5-dichloro-2,6-dimethyl-1H-pyridin-4-one
• CAS: 2971-90-6
• 化学式: C₇H₇Cl₂NO
• mdl: MFCD00476735
• 分子量: 192.045
• InChiKey: ZDPIZLCVJAAHHR-UHFFFAOYSA-N

物化性质

• 熔点：
  >320℃
• 沸点：
  318.4±37.0 °C(Predicted)
• 密度：
  1.2494 (rough estimate)
• 溶解度：
  可溶于水基（轻微），甲醇（轻微，加热）
• 物理描述：
  Clopidol is a white to light-brown, crystalline solid. Mp: 320°C. Practically insoluble in water. Administered to poultry to prevent the growth of pathogenic parasites.
• 颜色/状态：
  White to light-brown, crystalline solid
• 蒸汽压力：
  1.21X10-6 mm Hg at 25 °C (est)
• 分解：
  Hazardous decomposition products formed under fire conditions. - Carbon oxides, nitrogen oxides (NOx), Hydrogen chloride gas
• 解离常数：
  pKa = 4.79 (est)
• 碰撞截面：
  131.2 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

ADMET

毒理性

• 致癌性证据

A4：不能归类为人类致癌物。

A4: Not classifiable as a human carcinogen.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 暴露途径

吸入，皮肤和/或眼睛接触

inhalation, skin and/or eye contact

来源:The National Institute for Occupational Safety and Health (NIOSH)

毒理性

• 症状

眼睛、皮肤、鼻子、喉咙刺激；咳嗽

irritation eyes, skin, nose, throat; cough

来源:The National Institute for Occupational Safety and Health (NIOSH)

毒理性

• 靶器官

眼睛、皮肤、呼吸系统

Eyes, skin, respiratory system

来源:The National Institute for Occupational Safety and Health (NIOSH)

毒理性

• 副作用

生殖毒素 - 对生殖系统有毒的化学物质，包括对后代造成缺陷以及对男性或女性生殖功能的损害。生殖毒性包括发育效应。请参见生殖毒性风险评估指南。 皮肤致敏剂 - 可以诱导皮肤过敏反应的剂。 ACGIH致癌物 - 无法分类。

Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment. Skin Sensitizer - An agent that can induce an allergic reaction in the skin. ACGIH Carcinogen - Not Classifiable.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

安全信息

• 职业暴露等级：
  B
• 职业暴露限值：
  TWA: 10 mg/m3 (total), STEL: 20 mg/m3 (total)
• 安全说明：
  S26
• 危险品运输编号：
  NONH for all modes of transport
• 海关编码：
  2933399090
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• RTECS号：
  UU7711500
• WGK Germany：
  2
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

---

Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Clopidol
CAS-No. : 2971-90-6
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

---

Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust.
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
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
Other hazards - none

---

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C7H7Cl2NO
Molecular Weight : 192,04 g/mol
Component Concentration
Clopidol
CAS-No. 2971-90-6 -
EC-No. 221-008-2

---

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
Indication of any immediate medical attention and special treatment needed
no data available

---

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, nitrogen oxides (NOx), Hydrogen chloride gas
Carbon oxides, nitrogen oxides (NOx), Hydrogen chloride gas
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

---

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. Evacuate personnel to safe areas. Avoid breathing dust.
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.

---

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

---

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
Safety glasses with side-shields conforming to EN166 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
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).

---

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 insoluble
o) Partition coefficient: n- log Pow: 2,3
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

---

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

---

Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
LD50 Oral - rat - 18.000 mg/kg
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
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Additional Information
RTECS: UU7711500

---

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

---

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.

---

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

---

---

SECTION 15 - REGULATORY INFORMATION
N/A

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

性质与作用

氯羟吡啶，又称二氯二甲吡啶酚、克球酚（clopidol），是一种白色或类白色的粉末。它在甲醇或乙醇中极微溶，在水、丙酮、乙醚和苯中不溶，属于吡啶类化合物。这种药物具有广泛的抗球虫作用，常用于防治禽兔的球虫病。

注意事项

1. 由于氯羟吡啶能抑制鸡对球虫的免疫力，肉鸡在整个育雏期间不能中途停药；蛋鸡和种用肉鸡不宜使用。此外，该药品容易产生耐药虫株或虫种，因此必须按计划轮换使用其他抗球虫药物。氯羟吡啶与苄氧喹甲酯合并应用具有一定的协同效应。

2. 鸡的休药期为5天，兔也为5天。

用途

氯羟吡啶对鸡9种艾美耳球虫均有良好效果，尤其对抗柔嫩艾美耳球虫作用最强。其活性高峰时期是在子孢子期（即感染第一天），因此可以在感染前或同时给药，适用于预防和早期治疗。有资料表明，氯羟吡啶能抑制鸡对球虫的免疫力，过早停药可能导致球虫病暴发。目前认为，球虫容易对该药物产生耐药性。此外，该药物对兔球虫也有一定的防治效果。

生物活性

Clopidol (WR 61112)是一种抗原虫药剂。

体外研究

氯羟吡啶是兽药添加剂，广泛用于防止鸡的球虫感染。它被禁止用于出口家禽，中华人民共和国规定其在鸡肉中的最大残留量为0.01毫克/千克（以公斤计）。Clopidol抑制从未形成孢子的卵囊中分离出的线粒体中的电子转运。

化学性质

氯羟吡啶是一种白色或浅黄色粉末。无特殊气味，能稍微溶解于6mol/L盐酸或1mol/L氢氧化钠溶液，但在甲醇和乙醇中的微溶性，而不溶于水、苯、丙酮或乙醚。

用途

在国内是使用最广泛的抗球虫药之一，对各种鸡球虫均有效，并通常混入动物饲料中连续用药。此外，它也是一种羟基吡啶类抗球虫药。

反应信息

• 作为反应物：
  描述：

  氯羟吡啶 、 乙炔 在 cadmium(II) acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以27%的产率得到2,6-dimethyl-3,5-dichloro-4-vinyloxypyridine
  参考文献：
  名称：

  An unusual spatial structure of di-ortho-substituted hetaryl vinyl ethers according to1H and13C NMR data

  摘要：

  According to H-1 and C-13 NMR data, 2,6-dimethyl-3,5-dichloro-4-vinyloxy-pyridine and 2-methyl-4-methoxymethyl-5-hydroxymethyl-3-vinyloxypyridine exist predominantly as the sterically hindered s-cis conformation, with the angle between the hetaryl ring and the vinyloxypyridine plane about 60-degrees.

  DOI：

  10.1007/bf00960407
• 作为产物：
  描述：

  乙酰乙酸乙酯 在 ammonium hydroxide 、 氯 作用下， 反应 9.0h， 以91.5%的产率得到氯羟吡啶
  参考文献：
  名称：

  一种2,6-二甲基-3,5-二氯-4-羟基吡啶的制 备方法

  摘要：

  本发明公开了一种2,6‑二甲基‑3,5‑二氯‑4‑羟基吡啶的制备方法，所述方法以乙酰乙酸乙酯为原料，以弱碱性离子交换树脂为催化剂，在25～90℃条件下进行二聚反应，反应结束后，加入水并通入氨气在10～45℃进行氨化，再通入氯气在10～45℃进行氯化，反应液后处理，获得2,6‑二甲基‑3,5‑二氯‑4‑羟基吡啶；本发明以弱碱性离子交换树脂为催化剂，以乙酰乙酸乙酯为原料，采用串联技术制备目标产品，简化了单元反应，生产过程中易操作和后处理，反应结束后，只需对反应液进行过滤，滤饼回收催化剂，滤液重结晶就可以获得产物，产率达91.5％，产物分离纯化简单，无污染，是一种绿色制备方法。

  公开号：

  CN105753776B

文献信息

• Efficient Monofluoroalkylation of Thiophenols or Phenols with α-Bromo-α-Fluoroketones under Mild Conditions
  作者：Jingjing Wu、Fanhong Wu、Zhi Li、Mougui Fang、Yunli Liu、Yecheng Liu

  DOI：10.1055/a-1395-4788

  日期：2021.7

  nucleophilic substitution reaction between α-bromo-α-fluoroketones and thiophenols or phenols is reported for the synthesis of α-fluoro-β-ketosulfides or α-fluoro-β-ketone ethers in yields ranging from 78–93%. This method exhibits good functional group tolerance and a broad scope of nucleophilic substrates, including natural phenolic compounds.

  据报道，α-溴-α-氟代酮与硫酚或苯酚之间的有效亲核取代反应可合成α-氟代-β-酮硫醚或α-氟代-β-酮醚，产率为78-93％。该方法表现出良好的官能团耐受性和广泛的亲核底物，包括天然酚类化合物。
• ALKOXYCARBONATE ESTER PRODRUGS FOR USE AS ANTIMALARIAL AGENTS
  申请人：OREGON HEALTH & SCIENCE UNIVERSITY

  公开号：US20200369616A1

  公开（公告）日：2020-11-26

  Provided are compounds of Formula (I): wherein: X is selected from the group of F and Cl; Y is selected from the group of —CH 2 —, —CH 2 —CH 2 —, and —CH(CH 3 )—; R 1 is selected from cycloalkyl, heterocyclyl, aromatic, heteroaromatic, and linear and branched alkyl, alkenyl, and alkynyl chains.

  提供的是Formula (I)的化合物： 其中：X选自F和Cl；Y选自—CH2—、—CH2—CH2—和—CH(CH3)—；R1选自环烷基、杂环烷基、芳香族、杂芳香族以及直链和支链烷基、烯基和炔基链。
• GLUTATHIONE-CHOLESTEROL DERIVATIVES AS BRAIN TARGETING AGENTS
  申请人：South Dakota Board of Regents

  公开号：US20200048305A1

  公开（公告）日：2020-02-13

  The present invention describes compositions containing cholesterol-linker-glutathione conjugates for targeting the brain by overcoming barrier entry to the CNS through the blood brain barrier (BBB), including micelle and liposome forms of such compositions. In addition, methods for treating subjects by administering such compositions are also disclosed.

  本发明描述了含有胆固醇-连接剂-谷胱甘肽共轭物的组合物，通过克服血脑屏障（BBB）进入中枢神经系统的屏障入口，包括这些组合物的胶束和脂质体形式。此外，还公开了通过给予这些组合物治疗受试者的方法。
• Medicaments for the treatment of toxoplasmosis
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0567162A1

  公开（公告）日：1993-10-27

  The present invention relates to the use of 2-[4-(4-chlorophenyl) cyclohexyl]-3-hydroxy-1,4-naphthoquinone or a physiologically acceptable salt or other physiologically funtional derivative thereof for the manufacture of a medicament for the treatment and/or prophylaxis of toxoplasmosis in animals, to pharmaceutical compositions for the treatment and/or prophylaxis of toxoplasmosis, comprising said compound as active ingredient and to a method of treating or preventing toxoplasmosis in an animal which comprises administering to said animal an effective amount of said compound.

  本发明涉及2-[4-(4-氯苯基)环己基]-3-羟基-1,4-萘醌或其生理可接受的盐或其他生理功能衍生物用于制造治疗和/或预防动物弓形虫病的药物，涉及包含该化合物作为活性成分的治疗和/或预防弓形虫病的药物组合物，以及涉及治疗或预防动物弓形虫病的方法，该方法包括向所述动物施用有效量的该化合物。
• [EN] QUINOLONE-3-DIARYLETHERS<br/>[FR] QUINOLONE-3-DIARYLÉTHERS
  申请人：UNIV OREGON HEALTH & SCIENCE

  公开号：WO2017015360A1

  公开（公告）日：2017-01-26

  Disclosed are derivative compounds of ELQ-300 that include an ester at position 4. These compounds have enhanced properties relative to ELQ-300. Also disclosed are pharmaceutical compositions comprising the compounds and methods of treating and preventing malaria infections involving administering the pharmaceutical compositions to the subject.

  揭示了ELQ-300的衍生化合物，其中在位置4处包含酯基。这些化合物相对于ELQ-300具有增强的性质。还揭示了包括这些化合物的药物组合物以及治疗和预防涉及向受试者施用这些药物组合物的疟疾感染的方法。