4-甲酰基-3,5-二甲基-1H-吡咯-2-羧酸乙酯 | 2199-64-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 4-甲酰基-3,5-二甲基-1H-吡咯-2-羧酸乙酯
• 英文名称: ethyl 3,5-dimethyl-4-formyl-1H-pyrrole-2-carboxylate
• 英文别名: ethyl 4-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylate；ethyl 4-formyl-3,5-dimethylpyrrole-2-carboxylate；5-Ethoxycarbonyl-3-formyl-2,4-dimethyl-pyrrol；4-Formyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester
• CAS: 2199-64-6
• 化学式: C₁₀H₁₃NO₃
• mdl: MFCD00030384
• 分子量: 195.218
• InChiKey: CLJUICOFPKFFGJ-UHFFFAOYSA-N

物化性质

• 熔点：
  142 - 145oC
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 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,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P330,P362,P403+P233,P501
• 危险性描述：
  H302,H312,H332
• 储存条件：
  室温

SDS

Name:	Ethyl 4-formyl-3 5-dimethyl-1h-pyrrole-2-carboxylate 97% Material Safety Data Sheet
Synonym:
CAS:	2199-64-6

Section 1 - Chemical Product MSDS Name:Ethyl 4-formyl-3 5-dimethyl-1h-pyrrole-2-carboxylate 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2199-64-6	Ethyl 4-formyl-3,5-dimethyl-1H-pyrrole	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
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:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: 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.
Ingestion:
Get medical aid. 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.
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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Store under an inert atmosphere.

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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# 2199-64-6: Personal Protective Equipment Eyes: Not available.
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: 144 - 146 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: C10H13NO3
Molecular Weight: 195.22

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents, reducing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, acrid smoke and fumes.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2199-64-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 4-formyl-3,5-dimethyl-1H-pyrrole-2-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
No information available.
IMO
No information available.
RID/ADR
No information available.

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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# 2199-64-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 2199-64-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2199-64-6 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-甲酰基-3,5-二甲基-1H-吡咯-2-羧酸乙酯 在 盐酸 、 氢氧化钾 、 sodium hydroxide 、 磺酰氯 、 乙醚 、 乙醇 、 水 、 镍 、 甲胺 作用下， 160.0 ℃ 、14.71 MPa 条件下， 生成 2-(2-cyano-2-(methoxycarbonyl)vinyl)-3,4-dimethyl-1H-pyrrole
  参考文献：
  名称：

  Fischer; Hoefelmann, Justus Liebigs Annalen der Chemie, 1938, vol. 533, p. 216,229

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-二甲基-5-乙氧羰基-3-吡咯甲酸 在 C.I.酸性橙108 、 三氯氧磷 作用下， 生成 4-甲酰基-3,5-二甲基-1H-吡咯-2-羧酸乙酯
  参考文献：
  名称：

  DECARBOXYLATION AND FORMYLATION OF CERTAIN PYRROLE DERIVATIVES^*1

  摘要：

  DOI：

  10.1021/jo01367a013

文献信息

• Pyrrole-Based Hydrazones Synthesized and Evaluated In Vitro as Potential Tuberculostatics
  作者：Atanas Bijev、Maya Georgieva

  DOI：10.2174/157018010791306588

  日期：2010.7.1

  Twelve pyrrole hydrazones were synthesized and evaluated in vitro as inhibitors of Mycobacterium tuberculosis H37Rv with IC50 and IC90 to 5.92 μg/ml and 9.37 μg/ml respectively. The most active 12d (ethyl 5-(4-chlorophenyl)- 2-methyl-1-(4-(2-((5-nitrofuran-2-yl)methylene)hydrazinyl)-4-oxobutyl)-1H-pyrrole-3-carboxylate) has IC90 value of 9.372 μg/ml. The derived second order QSAR model favors moderate molecular surfaces in a combination with electronaccepting substituents in the aromatic hydrazone moiety.

  合成了十二种吡咯酰肼类化合物，并在体外评估了它们作为结核杆菌H37Rv抑制剂的活性，其IC50和IC90分别为5.92 μg/ml和9.37 μg/ml。活性最强的12d（乙基5-(4-氯苯基)-2-甲基-1-(4-(2-((5-硝基呋喃-2-基)亚甲基)肼基)-4-氧代丁基)-1H-吡咯-3-羧酸酯）的IC90值为9.372 μg/ml。由此推导的二级QSAR模型倾向于具有适度分子表面，并结合芳香肼部分中的电子接受取代基。
• The total synthesis of chlorophyll a
  作者：Robert Burns Woodward、William A. Ayer、John M. Beaton、Friedrich Bickelhaupt、Raymond Bonnett、Paul Buchschacher、Gerhard L. Closs、Hans Dutler、John Hannah、Fred P. Hauck、Shǒ Itǒ、Albert Langemann、Eugene Le Goff、Willy Leimgruber、Walter Lwowski、Jürgen Sauer、Zdenek Valenta、Heinrich Volz

  DOI：10.1016/0040-4020(90)80003-z

  日期：1990.1

  The total synthesis of chlorophyll a starting from Knorr's pyrrole (1) is described with full experimental detail. Forty six stages are involved to reach the target molecule, chlorin e6 trimethyl ester (46), from which the preparation of chlorophyll a has already been described.

  详细描述了从克诺尔吡咯（1）开始的叶绿素a的总合成。涉及到达到目标分子的四阶段是二氢卟酚e 6三甲基酯（46），从中已经描述了叶绿素a的制备。
• Oxidation of pyrrole α-methyl to formyl with ceric ammonium nitrate
  作者：Thomas Thyrann、David A. Lightner

  DOI：10.1016/0040-4039(95)00790-j

  日期：1995.6

  Pyrrole α-aldehydes can be prepared in high yield by oxidation of pyrrole α-methyl groups with ceric ammonium nitrate when the pyrrole ring also has an α-carboxylic acid ester group.

  当吡咯环也具有α-羧酸酯基时，可以通过用硝酸铈铵氧化吡咯α-甲基来高产率地制备吡咯α-醛。
• Study of antimicrobial and antioxidant activities of pyrrole-chalcones
  作者：Poonam Rawat、R.N. Singh、Alok Ranjan、Anshu Gautam、Sweta Trivedi、Mukesh Kumar

  DOI：10.1016/j.molstruc.2020.129483

  日期：2021.3

  compound (3a, 3c, 3g, 3h, 3i, and 5a) displayed better non-linear optical (NLO) responses than the standard p-Nitro aniline (pNA) in solvent and as well as in gas phase. 3g and 3i have high NLO values even in gas phase which can be attributed to their unsymmetrical and high non-planar structure. All studied compounds (3a, 3c, 3g, 3h, 3i, and 5a) show good antifungal and antibacterial activity against

  摘要 病原微生物对可获得的抗生素、抗焦虑药、镇静剂、催眠药和抗惊厥药的耐药性正在迅速成为世界范围内的首要问题。已对合成的吡咯查耳酮衍生物（3a、3c、3h、3i 和 5a）进行了详细的光谱、DFT、抗菌和抗氧化分析，并对其进行了解释。在 δ 7.656-6.960 范围内（3a、3c、3h、3i 和 5a）化合物的 1H NMR 光谱中出现双峰证实了 β-乙烯基 (=CH) 质子的存在和 δ 7.206-6.707 处的另一个双峰证实α-乙烯基 (=CH) 质子的存在，分别证实了报告产物的形成。全局亲电指数 (ω = 5.26 eV) 表明 (3g) 分子是所有研究化合物中的强亲电试剂。所有化合物都倾向于形成吡唑啉，恶唑啉杂环化合物，可能具有相当大的药理活性和材料应用。通过使用自洽反应场 (SCRF) 方法研究了溶剂对非线性光学性质 (NLO) 的影响。随着溶剂极性的增加，已经发现β值单调
• Low-valent titanium reductive coupling reactions of pyrrylaldehydes and pyrrylketones
  作者：Jianming Cheng、James E. Gano、Alan R. Morgan

  DOI：10.1016/0040-4039(96)00370-x

  日期：1996.4

  2-Pyrrylaldehydes are shown to react under McMurry conditions to give the expected coupling products in high yield, while 3-pyrrylaldehydes and 3-pyrrylketones give in good yields either rearrangement products or reduced McMurry products, depending upon the nature of the reactant.

  显示2-吡咯醛在McMurry条件下反应以高产率得到预期的偶联产物，而3-吡咯醛和3-吡咯酮根据反应物的性质产生重排产物或还原的McMurry产物的良好产率。

表征谱图