2-氯-4-碘烟酸甲酯 | 185041-05-8

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酯及其衍生物
• 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-氯-4-碘烟酸甲酯
• 英文名称: 2-chloro-4-iodonicotinic acid methyl ester
• 英文别名: methyl 2-chloro-4-iodonicotinate；methyl 2-chloro-4-iodopyridine-3-carboxylate
• CAS: 185041-05-8
• 化学式: C₇H₅ClINO₂
• 分子量: 297.48
• InChiKey: FXGPTKSMXUWJGO-UHFFFAOYSA-N

物化性质

• 熔点：
  85-86°C
• 沸点：
  304.4±37.0 °C(Predicted)
• 密度：
  1.924±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933399090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2-8°C

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Methyl 2-chloro-4-iodopyridine-3-carboxylate
CAS-No. : 185041-05-8
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
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : Methyl 2-chloro-4-iodonicotinate
Formula : C7H5ClINO2
Molecular Weight : 297,48 g/mol

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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, nitrogen oxides (NOx), Hydrogen chloride gas, Hydrogen iodide
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. 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.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
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.
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
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
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. 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 Melting point/range: 81 - 85 °C
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: 2,028
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
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

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  2-氯-4-碘烟酸	2-chloro-4-iodonicotinic acid	544671-78-5	C6H3ClINO2	283.453

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  2-氯-4-甲基烟酸甲酯	methyl 2-chloro-4-methylnicotinate	217811-63-7	C8H8ClNO2	185.61
  ——	2-chloro-4-cyanonicotinic acid methyl ester	1289188-60-8	C8H5ClN2O2	196.593
  ——	4-(aminomethyl)-2-chloronicotinic acid methyl ester	1289188-61-9	C8H9ClN2O2	200.625
  2-氯-4-甲基烟酸	2-chloro-4-methylnicotinic acid	142266-63-5	C7H6ClNO2	171.583
  ——	2-chloro-4-(cyanomethyl)nicotinic acid methyl ester	——	C9H7ClN2O2	210.62
  ——	methyl 2-chloro-4-(trifluoromethyl)nicotinate	196708-48-2	C8H5ClF3NO2	239.581

反应信息

• 作为反应物：
  描述：

  2-氯-4-碘烟酸甲酯 在 trans-bis(triphenylphosphine)palladium dichloride 、 20 % Pd(OH)2/C potassium fluoride 、 氢气 、 过氧化脲素 、 溶剂黄146 、 三氟乙酸酐 、 三氯氧磷 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 异丁酰胺 为溶剂， 150.0 ℃ 、101.33 kPa 条件下， 反应 40.0h， 生成 (R)-4-methyl-2-(4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)pentanamide
  参考文献：
  名称：

  FUSED HETEROAROMATIC PYRROLIDINONES

  摘要：

  本公开涉及公式1的化合物及其药学上可接受的盐，其中G、L1、L2、R1、R2、R3和R4在说明书中有定义。本公开还涉及制备公式1化合物的材料和方法，含有它们的药物组合物，以及它们在治疗涉及免疫系统和炎症的紊乱、疾病和病况，包括类风湿关节炎、血液恶性肿瘤、上皮癌（即癌症）和其他需要抑制SYK的紊乱、疾病和病况的用途。

  公开号：

  US20110152273A1
• 作为产物：
  描述：

  2-氯-4-碘吡啶 在 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-氯-4-碘烟酸甲酯
  参考文献：
  名称：

  [EN] MITOCHONDRIAL ALDEHYDE DEHYDROGENASE-2 MODULATORS AND METHODS OF USE THEREOF
  [FR] MODULATEURS DE L'ALDÉHYDE DÉSHYDROGÉNASE-2 MITOCHONDRIALE ET LEURS PROCÉDÉS D'UTILISATION

  摘要：

  公开号：

  WO2014160185A3

文献信息

• Ligand-Promoted <i>Meta</i>-C–H Arylation of Anilines, Phenols, and Heterocycles
  作者：Peng Wang、Marcus E. Farmer、Xing Huo、Pankaj Jain、Peng-Xiang Shen、Mette Ishoey、James E. Bradner、Steven R. Wisniewski、Martin D. Eastgate、Jin-Quan Yu

  DOI：10.1021/jacs.6b04966

  日期：2016.7.27

  Here we report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C-H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C-H arylation with heterocyclic

  在这里，我们报告了一种通用的 3-乙酰氨基-2-羟基吡啶类配体的开发，这些配体使用降冰片烯作为瞬态介质促进苯胺、杂环芳香胺、苯酚和 2-苄基杂环的间位 CH 芳基化。提供了 120 多个例子，证明了这种配体支架能够实现广泛的底物和偶联伙伴范围。使用该配体还首次实现了以杂环芳基碘化物作为偶联伙伴的间位 CH 芳基化。通过允许来那度胺衍生物的间位 CH 芳基化，展示了这种药物发现转化的效用。还展示了该反应的无银方案的第一步。
• Efficient Copper-Catalyzed Trifluoromethylation of Aromatic and Heteroaromatic Iodides: The Beneficial Anchoring Effect of Borates
  作者：Zsombor Gonda、Szabolcs Kovács、Csaba Wéber、Tamás Gáti、Attila Mészáros、András Kotschy、Zoltán Novák

  DOI：10.1021/ol501967c

  日期：2014.8.15

  Efficient copper-catalyzed trifluoromethylation of aromatic iodides was achieved with TMSCF3 in the presence of trimethylborate. The Lewis acid was used to anchor the in situ generated trifluoromethyl anion and suppress its rapid decomposition. Broad applicability of the new trifluoromethylating reaction was demonstrated in the functionalization of different aromatic and heteroaromatic iodides.

  在三甲基硼酸酯的存在下，用TMSCF 3实现了铜的芳族碘化物的三氟甲基化。路易斯酸用于固定原位生成的三氟甲基阴离子并抑制其快速分解。在不同的芳族和杂芳族碘化物的官能化中证明了新的三氟甲基化反应的广泛适用性。
• Synthesis of 4,5-Disubstituted Benzo[c][2,7]naphthyridines by Combined Metalation-Palladium-Catalysed Cross-Coupling Strategies. Preparation of 8h-Pyrido[4,3,2-<i>mn</i>]acridone as a Model of Cystodytin Alkaloids
  作者：F. Guillier、F. Nivoliers、C. Cochennec、A. Godard、F. Marsais、G. Quéguiner

  DOI：10.1080/00397919608003845

  日期：1996.12

  Abstract A short and efficient synthesis of 8H-pyrido[4,3,2-mn]acridone is described. The strategy involves the preparation of 4-chloro-5-methylbenzo[c][2,7]naphtyridine, as key intermediate, by metalation and Palladium catalyzed cross-coupling reaction. A second cross-coupling reaction and subsequent oxydation by SeO2 led to the title compound.

  摘要 描述了 8H-吡啶并[4,3,2-mn]吖啶酮的快速高效合成。该策略涉及通过金属化和钯催化的交叉偶联反应制备作为关键中间体的 4-氯-5-甲基苯并[c][2,7]萘啶。第二次交叉偶联反应和随后的 SeO2 氧化得到标题化合物。
• Discovery of TAK-659 an orally available investigational inhibitor of Spleen Tyrosine Kinase (SYK)
  作者：Betty Lam、Yasuyoshi Arikawa、Joshua Cramlett、Qing Dong、Ron de Jong、Victoria Feher、Charles E. Grimshaw、Pamela J. Farrell、Isaac D. Hoffman、Andy Jennings、Benjamin Jones、Jennifer Matuszkiewicz、Joanne Miura、Hiroshi Miyake、Srinivasa Reddy Natala、Lihong Shi、Masashi Takahashi、Ewan Taylor、Corey Wyrick、Jason Yano、Jonathan Zalevsky、Zhe Nie

  DOI：10.1016/j.bmcl.2016.10.087

  日期：2016.12

  Spleen Tyrosine Kinase (SYK) is a non-receptor cytoplasmic tyrosine kinase that is primarily expressed in hematopoietic cells. SYK is a key mediator for a variety of inflammatory cells, including B cells, mast cells, macrophages and neutrophils and therefore, an attractive approach for treatment of both inflammatory diseases and oncology indications. Using in house co-crystal structure information

  脾酪氨酸激酶（SYK）是一种非受体胞质酪氨酸激酶，主要在造血细胞中表达。SYK是包括B细胞，肥大细胞，巨噬细胞和嗜中性粒细胞在内的多种炎性细胞的关键介体，因此是治疗炎性疾病和肿瘤适应症的一种有吸引力的方法。利用内部共晶体结构信息和基于结构的药物设计，我们设计和优化了一系列新的杂芳族吡咯烷酮SYK抑制剂，从而选择了开发候选TAK-659。TAK-659目前正在接受针对晚期实体瘤和淋巴瘤恶性肿瘤的I期临床试验，针对结合nivolumab的晚期实体瘤的Ib期研究以及针对复发/难治性AML的PhIb / II试验。
• Discovery of novel 4-phenyl-2-(pyrrolidinyl)nicotinamide derivatives as potent Nav1.1 activators
  作者：Tohru Miyazaki、Masanori Kawasaki、Atsushi Suzuki、Yuki Ito、Akio Imanishi、Takamitsu Maru、Tomohiro Kawamoto、Tatsuki Koike

  DOI：10.1016/j.bmcl.2019.01.023

  日期：2019.3

  combinations of IonWorks and Q-patch assays successfully identified the nicotinamide derivative 4. Its increasing decay time constant (tau) of Nav1.1 currents at 0.03 μM along with significant selectivity against Nav1.2, Nav1.5, and Nav1.6 and acceptable brain exposure in mice was observed. Compound 4 is a promising Nav1.1 activator that can be used to analyze pathophysiological functions of the Nav1

  电压门控钠通道Nav1.1主要在小白蛋白阳性快速加标中间神经元中表达，并与Dravet综合征遗传相关。从高通量筛选命中的异恶唑衍生物5开始，通过结合IonWorks和Q-patch分析对5进行修饰，成功鉴定出烟酰胺衍生物4。其Nav1.1电流在0.03μM时的增加的衰减时间常数（tau）以及显着的选择性小鼠对Nav1.2，Nav1.5和Nav1.6的抵抗力和可接受的大脑暴露情况都可以观察到。化合物4是一种很有前途的Nav1.1激活剂，可用于分析Nav1.1通道的病理生理功能，以治疗各种中枢神经系统疾病。