2-碘-5-三氟甲基吡啶 | 100366-75-4

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 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: 2-碘-5-三氟甲基吡啶
• 中文别名: 5-三氟甲基-2-碘吡啶；2-碘-5-三氟甲基砒啶
• 英文名称: 2-iodo-5-trifluoromethylpyridine
• 英文别名: 2-Iodo-5-(trifluoromethyl)pyridine
• CAS: 100366-75-4
• 化学式: C₆H₃F₃IN
• 分子量: 272.996
• InChiKey: WSEVWIIOEQZEOU-UHFFFAOYSA-N

物化性质

• 熔点：
  82-83 °C(Solv: hexane (110-54-3))
• 沸点：
  215.7±40.0 °C(Predicted)
• 密度：
  1.974±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S45
• 危险类别码：
  R25
• WGK Germany：
  3
• 海关编码：
  2933399090
• 危险标志：
  GHS06
• 危险性描述：
  H301
• 危险性防范说明：
  P301 + P310

SDS

---

SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 2-Iodo-5-Trifluoromethyl-Pyridine
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

---

SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Oral (Category 3), H301
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
T Toxic R25
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)
H301 Toxic if swallowed.
Precautionary statement(s)
P301 + P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/
physician.
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.

---

SECTION 3: Composition/information on ingredients
Substances
Molecular weight : 273 g/mol
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
2-Iodo-5-Trifluoromethyl-Pyridine
Acute Tox. 3; H301 <= 100 %
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
2-Iodo-5-Trifluoromethyl-Pyridine
T, R25 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

---

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. Take victim immediately to hospital. 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
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

---

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 firefighting if necessary.
Further information
No data available

---

SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Wear respiratory protection. 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
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.

---

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, acute toxic Cat.3 / toxic hazardous materials or hazardous
materials causing chronic effects
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

---

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 N99 (US) or type P2 (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
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.

---

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

---

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
Other decomposition products - No data available
In the event of fire: see section 5

---

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.
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

---

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

---

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.

---

SECTION 14: Transport information
UN number
ADR/RID: 2811 IMDG: 2811 IATA: 2811
UN proper shipping name
ADR/RID: TOXIC SOLID, ORGANIC, N.O.S. (2-Iodo-5-Trifluoromethyl-Pyridine)
IMDG: TOXIC SOLID, ORGANIC, N.O.S. (2-Iodo-5-Trifluoromethyl-Pyridine)
IATA: Toxic solid, organic, n.o.s. (2-Iodo-5-Trifluoromethyl-Pyridine)
Transport hazard class(es)
ADR/RID: 6.1 IMDG: 6.1 IATA: 6.1
Packaging group
ADR/RID: III IMDG: III IATA: III
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
No data available

---

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

---

SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Acute Tox. Acute toxicity
H301 Toxic if swallowed.
Full text of R-phrases referred to under sections 2 and 3
T Toxic
R25 Toxic if swallowed.
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.

制备方法与用途

理化性质

5-三氟甲基-2-碘吡啶在常温常压下为米白色固体粉末，具有微弱的碱性，并可与常见的酸性物质结合成盐。它易溶于常见有机溶剂和酸性水溶液。

应用

5-三氟甲基-2-碘吡啶是一种吡啶类化合物。由于吡啶环缺电子性质的影响，该物质结构中的碘原子可在强亲核试剂的进攻下发生脱碘官能团化反应；它也可在金属铜催化作用下与芳基卤化合物发生交叉偶联反应。此外，在氰基铜的作用下，它可以与芳基碘发生脱碘氰基化反应，用于吡啶氰类物质的合成。

反应信息

• 作为反应物：
  描述：

  2-碘-5-三氟甲基吡啶 在 sodium tetrahydroborate 、 正丁基锂 作用下， 以 甲醇 、 正己烷 、 甲苯 为溶剂， 反应 2.08h， 生成 (5-三氟甲基吡啶-2-基)甲醇
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationships of Varied Ether Linker Analogues of the Antitubercular Drug (6S)-2-Nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824)

  摘要：

  New analogues of antitubercular drug PA-824 were synthesized, featuring alternative side chain ether linkers of varying size and flexibility, seeking drug candidates with enhanced metabolic stability and high efficacy. Both alpha-methyl substitution and removal of the benzylic methylene were broadly tolerated in vitro, with a biaryl example of the latter class exhibiting an 8-fold better efficacy than the parent drug in a mouse model of acute Mycobacterium tuberculosis infection and negligible fragmentation to an alcohol metabolite in liver microsomes. Extended linkers (notably propenyloxy, propynyloxy, and pentynyloxy) provided greater potencies against replicating M. tb (monoaryl analogues), with propynyl ethers being most effective under anaerobic (nonreplicating) conditions (mono/biaryl analogues). For benzyloxybenzyl and biaryl derivatives, aerobic activity was maximal with the original (OCH2) linker. One propynyloxy-linked compound displayed an 89-fold higher efficacy than the parent drug in the acute model, and it was slightly superior to antitubercular drug OPC-67683 in a chronic infection model.

  DOI：

  10.1021/jm200377r
• 作为产物：
  描述：

  2,6-二氯-3-(三氟甲基)吡啶 在 氢碘酸 、 sodium iodide 作用下， 反应 24.0h， 以39%的产率得到2-碘-5-三氟甲基吡啶
  参考文献：
  名称：

  Chemistry of heterocyclic compounds series. Part 108. Reductive dehalogenation of electron-poor heterocycles: nicotinic acid derivatives

  摘要：

  DOI：

  10.1021/jo00356a043

文献信息

• Substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：——

  公开号：US20030045546A1

  公开（公告）日：2003-03-06

  The present invention is directed to substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs thereof, represented by the Formula I: 1 wherein Ar 1 , Ar 3 , A, B and D are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及取代的3-芳基-5-芳基-[1,2,4]-噁二唑及其类似物，由以下式I表示： 1 其中Ar1，Ar3，A，B和D在此处定义。本发明还涉及发现具有式I的化合物是caspase的激活剂和凋亡诱导剂。因此，本发明的caspase激活剂和凋亡诱导剂可用于诱导在各种临床病况中发生未受控制的异常细胞生长和扩散的细胞死亡。
• [EN] PYRAZOLESULFONAMIDES AS ANTITUMOR AGENTS<br/>[FR] PYRAZOLESULFONAMIDES EN TANT QU'AGENTS ANTITUMORAUX
  申请人：PELOTON THERAPEUTICS INC

  公开号：WO2020210139A1

  公开（公告）日：2020-10-15

  Compounds of formula I, that induce RBM39 protein degradation, pharmaceutical compositions containing these compounds, and methods of using these compounds for treating diseases associated with RBM39 protein activity are described herein.

  公式I的化合物，能诱导RBM39蛋白降解，包含这些化合物的药物组合物，以及使用这些化合物治疗与RBM39蛋白活性相关疾病的方法，在本发明中有所描述。
• [EN] MORPHOLINONE COMPOUNDS AS FACTOR IXA INHIBITORS<br/>[FR] COMPOSÉS DE MORPHOLINONE EN TANT QU'INHIBITEURS DE FACTEUR IXA
  申请人：MOCHIDA PHARM CO LTD

  公开号：WO2010065717A1

  公开（公告）日：2010-06-10

  The present invention provides a compound of Formula (I) as described herein, or a pharmaceutically acceptable salt or a solvate thereof. The present invention also provides pharmaceutical compositions comprising one or more said compounds, and methods for using said compounds for treating or preventing a thromboses, embolisms, hypercoagulability or fibrotic changes.

  本发明提供了如下描述的化合物I的化合物，或其药用可接受的盐或溶剂。本发明还提供包含一个或多个所述化合物的药物组合物，以及使用所述化合物治疗或预防血栓、栓塞、高凝血性或纤维变化的方法。
• A Unified Strategy for Arylsulfur(VI) Fluorides from Aryl Halides: Access to Ar‐SOF ₃ Compounds
  作者：Lin Wang、Josep Cornella

  DOI：10.1002/anie.202009699

  日期：2020.12.21

  access various arylsulfur(VI) fluorides from commercially available aryl halides in a divergent fashion is presented. Firstly, a novel sulfenylation reaction with the electrophilic N‐(chlorothio)phthalimide (Cl‐S‐Phth) and arylzinc reagents afforded the corresponding Ar‐S‐Phth compounds. Subsequently, the S(II) atom was selectively oxidized to distinct fluorinated sulfur(VI) compounds under mild conditions

  提出了一种以不同方式从市售芳基卤化物中选择性获取各种芳基硫 (VI) 氟化物的便捷方案。首先，用亲电子的N- (氯硫代)邻苯二甲酰亚胺 (Cl-S-Phth) 和芳基锌试剂进行新型磺基化反应，得到相应的 Ar-S-Phth 化合物。随后，S(II)原子在温和条件下被选择性氧化成不同的氟化硫(VI)化合物。对氧化方案的轻微修改允许在 S(VI) 中心化学选择性安装 1、3 或 4 个氟原子，提供相应的 Ar-SO 2 F、Ar-SOF 3和 Ar-SF 4 Cl。值得注意的是，该策略能够有效地将稀有且尚未开发的 ‐SOF 3部分引入各种（杂）芳基中。反应性研究表明，这种难以捉摸的 Ar-SOF 3可用作合成备受期待的芳基磺酰亚胺酰氟 (Ar-SO(NR)F) 的关键。
• Ir(I)‐Catalyzed C−H Glycosylation for Synthesis of 2‐Indolyl‐ <i>C</i> ‐Deoxyglycosides
  作者：Changyue Yu、Yichu Liu、Xiong Xie、Shulei Hu、Shurui Zhang、Mingjie Zeng、Dan Zhang、Jiang Wang、Hong Liu

  DOI：10.1002/adsc.202100855

  日期：2021.11.9

  we present an efficient, regioselective, stereoselective and widely applicable strategy for the synthesis of 2-indolyl-C-deoxyglycosides via Ir(I)-catalyzed, pyridine-group-directed C−H functionalization. This method exhibits high tolerance for the functional groups of indoles and the protecting groups of carbohydrates. Moreover, this protocol has good stereoselectivity and mainly produces β-configuration

  2-脱氧建设Ç -glycosides已逐渐成为糖化学的一个热点在最近几年。在这项工作中，我们提出了2-吲哚基的合成的有效，区域选择性，立体选择性和广泛适用的策略Ç -deoxyglycosides经由铱（I）催化，吡啶基团的定向C-H官能化。该方法对吲哚的官能团和碳水化合物的保护基团具有高耐受性。此外，该协议具有良好的立体选择性，主要生产β-构型产品。为进一步应用进行了克级合成和一些实际转化。同时，我们还探索了该方法的机理并提出了催化循环