2,5-二氯吡咯-3-羧酸甲酯 | 69687-80-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2,5-二氯吡咯-3-羧酸甲酯
• 中文别名: 2,5-二甲基-吡咯-3-羧酸甲酯；2,5-二甲基-1H-吡咯-3-羧酸甲酯
• 英文名称: methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate
• 英文别名: 2,5-dimethyl-1H-pyrrole-3-carboxylic acid methyl ester；2,5-dimethylpyrrole-3-carboxylic acid methyl ester；Methyl 2,5-dimethylpyrrole-3-carboxylate；2,5-dimethyl-pyrrole-3-carboxylic acid methyl ester；2,5-Dimethyl-pyrrol-3-carbonsaeure-methylester；methyl 3-(2,5-dimethyl-1H-pyrrolyl)carboxylate
• CAS: 69687-80-5
• 化学式: C₈H₁₁NO₂
• mdl: MFCD00203859
• 分子量: 153.181
• InChiKey: OQWZEJIISPYZPW-UHFFFAOYSA-N

物化性质

• 熔点：
  115 °C
• 沸点：
  294℃
• 密度：
  1.108
• 闪点：
  132℃
• 稳定性/保质期：
  远离氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 安全说明：
  S26,S37
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  应将物品存放在密封容器中，并置于阴凉、干燥处。存储地点需远离氧化剂。

SDS

Name:	Methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate, 95+% Material Safety Data Sheet
Synonym:	None Known.
CAS:	69687-80-5

Section 1 - Chemical Product MSDS Name: Methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate, 95+% Material Safety Data Sheet
Synonym: None Known.

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SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
69687-80-5	Methyl 2,5-dimethyl-1H-pyrrole-3-carbo	95+%	unlisted

+++++
Hazard Symbols: XI

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SECTION 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Irritating to eyes, respiratory system and skin. Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
No information found.

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SECTION 4 - FIRST AID MEASURES
Eyes:
Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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SECTION 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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SECTION 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions. Provide ventilation.

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SECTION 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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SECTION 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 69687-80-5: Personal Protective Equipment
Eyes:
Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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SECTION 9 - PHYSICAL AND CHEMICAL PROPERTIES
Physical State: Solid
Color: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 115 - 118 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H11NO2
Molecular Weight: 153

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SECTION 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Bases, halogenated agents, halogens, strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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SECTION 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 69687-80-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate - Not listed by ACGIH, IARC, or NTP.

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SECTION 12 - ECOLOGICAL INFORMATION

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SECTION 13 - DISPOSAL CONSIDERATIONS Dispose of in a manner consistent with federal, state, and local regulations.

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SECTION 14 - TRANSPORT INFORMATION IATA Not regulated as a hazardous material. IMO Not regulated as a hazardous material. RID/ADR Not regulated as a hazardous material.

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SECTION 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 37/39 Wear suitable gloves and eye/face protection. WGK (Water Danger/Protection) CAS# 69687-80-5: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 69687-80-5 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 69687-80-5 is not listed on the TSCA inventory. It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 6/10/2003 Revision #1 Date: 1/19/2005 The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,5-二氯吡咯-3-羧酸甲酯 在 正丁基锂 、 三氟化硼乙醚 、 pyridinium hydrobromide perbromide 、 苄基三甲基氢氧化铵 、 sodium hydride 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 5.0h， 生成 2,5-二甲基-4-[2-(苯基甲基)苯甲酰]-1H-吡咯-3-羧酸甲酯
  参考文献：
  名称：

  Discovery and synthesis of methyl 2,5-dimethyl-4-[2-(phenylmethyl)benzoyl]-1H-pyrrole-3-carboxylate (FPL 64176) and analogs: the first examples of a new class of calcium channel activator

  摘要：

  Methyl 2,5-dimethyl-4-[2-(phenylmethyl)benzoyl]-1H-pyrrole-3-carboxylate, FPL 64176 (1), is the first example of a new class of calcium channel activator (CCA) that does not act on any of the well-defined calcium channel modulator receptor sites, as typified by verapamil, diltiazem, and the dihydropyridines. The potent activity of 1, having the 2-(phenylmethyl)benzoyl substituent, was predicted using QSAR on an initial set of less potent benzoylpyrroles. When compared to the CCA Bay K 8644, 1 has simialr potency on calcium uptake into GH3 cells (both have EC50 approximately 0.015 muM) but is appreciably more potent functionally at increasing contractility in a guinea pig atria preparation (1 has EC50 = 0.049 muM vs Bay K 8644 EC50 = 1.95 muM). 1 is an achiral, pharmacologically clean agonist with no demonstrable partial agonist properties and possesses appreciably higher efficacy than Bay K 8644. It should therefore become a useful biochemical and pharmacological tool for the study of calcium channels in many cell types.

  DOI：

  10.1021/jm00071a004
• 作为产物：
  描述：

  乙基4-氰基-2,5-二甲基-1H-吡咯-3-羧酸酯 在 sodium hydroxide 、 乙醚 作用下， 生成 2,5-二氯吡咯-3-羧酸甲酯
  参考文献：
  名称：

  Fischer; Mueller, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1937, vol. 246, p. 31,38

  摘要：

  DOI：

文献信息

• Catalytic Methylation of CH Bonds Using CO₂and H₂
  作者：Yuehui Li、Tao Yan、Kathrin Junge、Matthias Beller

  DOI：10.1002/anie.201405779

  日期：2014.9.22

  Formation of CC bonds from CO2 is a much sought after reaction in organic synthesis. To date, other than CH carboxylations using stoichiometric amounts of metals, base, or organometallic reagents, little is known about CC bond formation. In fact, to the best of our knowledge no catalytic methylation of CH bonds using CO2 and H2 has been reported. Described herein is the combination of CO2 and H2 for efficient

  由CO 2形成CC键是有机合成中非常需要的反应。迄今为止，除了使用化学计算量的金属，碱或有机金属试剂进行的CH羧化反应外，对CC键的形成知之甚少。实际上，据我们所知，没有报道使用CO 2和H 2催化CH键的甲基化。本文描述的是CO 2和H 2的组合，用于碳亲核试剂（如吲哚，吡咯和富电子芳烃）的有效甲基化。使用低聚甲醛的对比实验显示出与CO 2相似的反应性/ H 2系统。
• PHTHALAZINONE DERIVATIVES
  申请人：MENEAR Keith Allan

  公开号：US20090192156A1

  公开（公告）日：2009-07-30

  A compound of the formula (I): wherein: A and B together represent an optionally substituted, fused aromatic ring; X and Y are selected from CH and CH, CF and CH, CH and CF and N and CH respectively; R C is selected from H, C 1-4 alkyl; and R 1 is selected from C 1-7 alkyl, C 3-20 heterocyclyl and C 5-20 aryl, which groups are optionally substituted; or R C and R 1 together with the carbon and oxygen atoms to which they are attached form a spiro-C 5-7 oxygen-containing heterocyclic group, which is optionally substituted or fused to a C 5-7 aromatic ring.

  其中： A和B一起代表一个可选取代的融合芳香环；X和Y分别从CH和CH、CF和CH、CH和CF以及N和CH中选择；RC从H、C1-4烷基中选择；R1从C1-7烷基、C3-20杂环烷基和C5-20芳基中选择，这些基团可选取代；或者RC和R1与它们连接的碳和氧原子一起形成一个可选取代或与C5-7芳香环融合的螺环C5-7含氧杂环基。
• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSÉS CHIMIQUES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2013127780A1

  公开（公告）日：2013-09-06

  Compounds of the formula (I), wherein the substituent is as defined in claim 1, are useful as a pesticides.

  式(I)的化合物，其中取代基如权利要求1所定义的那样，可用作杀虫剂。
• Regioselective Synthesis of 2,3,4- or 2,3,5-Trisubstituted Pyrroles via [3,3] or [1,3] Rearrangements of <i>O</i>-Vinyl Oximes
  作者：Heng-Yen Wang、Daniel S. Mueller、Rachna M. Sachwani、Rachel Kapadia、Hannah N. Londino、Laura L. Anderson

  DOI：10.1021/jo200061b

  日期：2011.5.6

  base. When enolization is favored, a [3,3] rearrangement followed by a Paal-Knorr cyclization provides a 2,3,4-trisubstituted pyrrole; when enolization is disfavored, a [1,3] rearrangement occurs prior to enolization to produce a 2,3,5-trisubstituted pyrrole after cyclization. Optimization and scope of the O-allyl oxime isomerization and subsequent pyrrole formation are discussed and mechanistic pathways

  2,3,4-或2,3,5-三取代的吡咯的区域选择性合成分别通过O-乙烯基肟的[3,3]和[1,3]σ向重排实现。易于制备的O-烯丙基肟的铱催化异构化作用使得能够快速获得O-乙烯基肟。吡咯形成的区域选择性可以通过α-取代基的身份或通过添加胺碱来控制。当需要烯醇化时，先进行[3,3]重排，然后进行Paal-Knorr环化，即可得到2,3,4-三取代的吡咯；当烯醇化不利时，在烯醇化之前会发生[1,3]重排，从而在环化后产生2,3,5-三取代的吡咯。O的优化和范围讨论了烯丙基肟的异构化和随后吡咯的形成，并提出了机理。提供了选择带有β-酯O-烯丙基肟底物的[3,3]重排或[1,3]重排产物的条件。
• Synthesis of [3H]FPL 64176, a potent calcium channel activator
  作者：Christian Foged、Peter Madsen

  DOI：10.1002/jlcr.2580340710

  日期：1994.7

  Tritium labelled FPL 64176 (1, methyl 2,5-dimethyl-4-2-(phenylmethyl)benzoyl]-1H-pyrrole-3-carboxylate), a potent calcium channel activator with insulinotropic properties was synthesized from the corresponding bromo derivative (3) using tritium gas and Pd/C catalyst. (3) was in turn prepared from methyl 2,5-dimethylpyrrole-3-carboxylate (4) in a one pot procedure. The specific activity of [3H]FPL 64176 was 38 mCi/mmol and radiochemical purity >98%.

  用氚标记的FPL 64176（1，甲基2,5-二甲基-4-2-(苯基甲基)苯甲酰]-1H-吡咯-3-羧酸酯）是一种有效的钙通道激活剂，具有促胰岛素分泌特性。它是通过使用氚气和Pd/C催化剂从相应的溴衍生物（3）合成的。（3）则是通过一种锅法从甲基2,5-二甲基吡咯-3-羧酸酯（4）制备的。[3H]FPL 64176的特定活性为38 mCi/mmol，放射化学纯度>98%。