3-羧基-1,4-二甲基-吡咯-2-乙酸 | 33369-45-8

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 3-羧基-1,4-二甲基-吡咯-2-乙酸
• 中文别名: 3-羧基-1,4-二甲基-1H-吡咯-2-乙酸；2-(羧基甲基)-1,4-二甲基-1H-吡咯-3-甲酸；3-羧基-1,4-二甲基吡咯-2-乙酸
• 英文名称: 3-carboxy-1,4-dimethyl-1H-pyrrole-2-acetic acid
• 英文别名: 2-(carboxymethyl)-1,4-dimethyl-1H-pyrrole-3-carboxylic acid；(3-carboxy-1,4-dimethylpyrrol-2-yl)acetic acid；3-carboxy-1,4-dimethylpyrrole-2-acetic acid；3-carboxy-1,4-dimethylpyrrol-2-acetic acid；1,4-dimethyl-3-carboxypyrrole-2-acetic acid；2-(carboxymethyl)-1,4-dimethylpyrrole-3-carboxylic acid
• CAS: 33369-45-8
• 化学式: C₉H₁₁NO₄
• mdl: MFCD00010742
• 分子量: 197.191
• InChiKey: FASPXTNRUAOAGU-UHFFFAOYSA-N

物化性质

• 熔点：
  198 °C
• 沸点：
  334.28°C (rough estimate)
• 密度：
  1.3075 (rough estimate)
• 稳定性/保质期：
  <p>遵照规定使用和储存，则不会分解。</p>

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  79.5
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25,S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 储存条件：
  存放在0至6℃阴凉干燥处。

SDS

Name:	3-Carboxy-1 4-dimethyl-1h-pyrrole-2-acetic acid Material Safety Data Sheet
Synonym:	3-Carboxy-1,4-dimethyl-2-pyrroleaceti
CAS:	33369-45-8

Section 1 - Chemical Product MSDS Name:3-Carboxy-1 4-dimethyl-1h-pyrrole-2-acetic acid Material Safety Data Sheet
Synonym:3-Carboxy-1,4-dimethyl-2-pyrroleaceti

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
33369-45-8	3-Carboxy-1,4-dimethyl-1H-pyrrole-2-ac	100.0	251-476-3

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.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
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 immediately.
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:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
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:

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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 agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 33369-45-8: 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: Not available.
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 198 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C9H11NO4
Molecular Weight: 197.19

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 33369-45-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-Carboxy-1,4-dimethyl-1H-pyrrole-2-acetic acid - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Other No information available.

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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 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 33369-45-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 33369-45-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 33369-45-8 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：

  3-羧基-1,4-二甲基-吡咯-2-乙酸 在 3-(tert-butylamino)-4-(((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione 、 乙酰氯 、 三甲基硅烷化重氮甲烷 作用下， 以 乙醚 、 甲基叔丁基醚 为溶剂， 反应 38.5h， 生成 1'-tert-butyl 6-ethyl 7-methyl 1,3-dimethyl-2',4-dioxo-1,4,6,7-tetrahydrospiro[indole-5,3'-indoline]-1',6,7-tricarboxylate
  参考文献：
  名称：

  催化不对称田村环加成反应

  摘要：

  在新型的基于叔丁基取代的方酸酰胺的催化剂的存在下，可烯醇化的酸酐与亚烷基氧吲哚反应生成具有重要对映体和非对映体控制意义的具有重要合成意义的螺并吲哚产物。该方法学范围很广，包括均苯二酸酐和戊二酸酐衍生物，它们导致结构上多样化的产品。谷氨酸衍生的酸酐经过干净的环化后脱羧过程，这不是涉及高邻苯二甲酸衍生的酸酐的反应的特征。已探究了反应温度对非对映异构体控制的异常影响，反应发生在30°C和-30°C下，仅在一个立体中心提供差向异构体的产物，接近光学纯度。

  DOI：

  10.1002/anie.201309297
• 作为产物：
  描述：

  3-(乙氧基羰基)-1,4-二甲基-1H-吡咯-2-乙酸乙酯 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 3.0h， 以98%的产率得到3-羧基-1,4-二甲基-吡咯-2-乙酸
  参考文献：
  名称：

  催化不对称田村环加成反应

  摘要：

  在新型的基于叔丁基取代的方酸酰胺的催化剂的存在下，可烯醇化的酸酐与亚烷基氧吲哚反应生成具有重要对映体和非对映体控制意义的具有重要合成意义的螺并吲哚产物。该方法学范围很广，包括均苯二酸酐和戊二酸酐衍生物，它们导致结构上多样化的产品。谷氨酸衍生的酸酐经过干净的环化后脱羧过程，这不是涉及高邻苯二甲酸衍生的酸酐的反应的特征。已探究了反应温度对非对映异构体控制的异常影响，反应发生在30°C和-30°C下，仅在一个立体中心提供差向异构体的产物，接近光学纯度。

  DOI：

  10.1002/anie.201309297

文献信息

• A mild and facile synthesis of carboxylic anhydrides
  作者：Y. Kita、S. Akai、M. Yoshigi、Y. Nakajima、H. Yasuda、Y. Tamura

  DOI：10.1016/s0040-4039(01)81751-2

  日期：1984.1

  Reaction of carboxylic acids with trimethylsilylethoxyacetylene in an inert solvent under mild conditions affords the corresponding carboxylic anhydrides in almost quantitative yields.

  在惰性溶剂中，羧酸与三甲基甲硅烷基乙氧基乙炔在温和的条件下反应，以几乎定量的产率得到相应的羧酸酐。
• 1,3,6-trihydro-6-aza-3-oxapentalen-2-one derivatives for the treatment
  申请人：Cell Pathways Inc

  公开号：US05939417A1

  公开（公告）日：1999-08-17

  1,3,6-Trihydro-6-Aza-3-Oxapentalen-2-One Derivatives for inhibiting neoplastic conditions.

  用于抑制肿瘤性疾病的1,3,6-三羟基-6-氮代-3-氧代戊二烯-2-酮衍生物。
• Reaction of heteroaromatic analogs of homophthalic anhydride: Synthesis of hetero analogs of peri-hydroxy polycyclic aromatic compounds, isocoumarins, isoquinolinones, and related compounds.
  作者：YASUYUKI KITA、SHINICHIRO MOHRI、TERUHISA TSUGOSHI、HATSUO MAEDA、YASUMITSU TAMURA

  DOI：10.1248/cpb.33.4723

  日期：——

  The reactions of heterohomophthalic anhydrides, 3-carboxy-1-methylindole-2-acetic anhydride (4), 2-carboxybenzo [b] furan-3-acetic anhydride (5), 2-carboxythiophene-3-acetic anhydride (6), and 3-carboxy-1, 4-dimethylpyrrole-2-acetic anhydride (23) with carbon-carbon multiple bonds (C=C and C≡C), acylating agents, and cyclic imines are described. Treatment of the anhydrides (4-6) with various compounds containing carbon-carbon multiple bonds (7-10) in the presence of a strong base caused cycloaddition with spontaneous extrusion of carbon dioxide to give the corresponding linearly condensed peri-hydroxy heteroaromatic compounds (11-19), regioselectively. Base-catalyzed acylation of 4 with acetic anhydride and β, β-dimethylacryloyl chloride gave 3, 5-dimethylpyrano [4, 3-b] indol-1 (5H)-one (21) and 3, 3, 11-trimethyl-3, 4-dihydropyrano [4', 3' : 2, 3]-pyrano [4, 5-b] indole-1, 6 (11H)-dione (22), respectively. Reaction of the anhydrides (4, 6, and 23) with 3, 4-dihydroisoquinoline (24) gave the corresponding condensation products, 14-carboxy-13-methyl-5, 6, 14, 14a-tetrahydrobenz [a] indolo [3, 2-g] quinolizin-8 (13H)-one (25), 12-carboxy-5, 6, 12, -12a-tetrahydrobenzo [a] thieno [2, 3-g] quinolizin-8-one (26) and 12-carboxy-11-methyl-5, 6, 12, 12a-tetrahydrobenzo [a] pyrrolo [3, 2-g] quinolizin-8 (11H)-one (27), in high yields.

  杂环邻苯二甲酸酐、3-羧基-1-甲基吲哚-2-乙酸酐 (4)、2-羧基苯并[b]呋喃-3-乙酸酐 (5)、2-羧基噻吩-3-乙酸酐 (6)、3-羧基-1, 4-二甲基吡咯-2-乙酸酐 (23) 与碳-碳多键（C=C 和 C≡C）、酰化剂和环状亚胺的反应、和 3-羧基-1，4-二甲基吡咯-2-乙酸酐（23）的碳-碳多键（C=C 和 C≡C）、酰化剂和环状亚胺。在强碱存在下，将酸酐（4-6）与各种含有碳碳多键的化合物（7-10）进行处理，可引起环化反应，并自发挤出二氧化碳，从而得到相应的线性缩合过羟基杂芳香族化合物（11-19），且具有区域选择性。在碱催化下，4 与乙酸酐和 β，β-二甲基丙烯酰氯发生酰化反应，分别得到 3，5-二甲基吡喃并[4，3-b]吲哚-1 (5H)-酮（21）和 3，3，11-三甲基-3，4-二氢吡喃并[4'，3' : 2，3]吡喃并[4，5-b]吲哚-1，6 (11H)-二酮（22）。酸酐（4、6 和 23）与 3，4-二氢异喹啉（24）反应得到相应的缩合产物，即 14-羧基-13-甲基-5，6，14，14a-四氢苯并[a]吲哚并[3，2-g]喹嗪-8 (13H)-酮（25）、高产率的 12-羧基-5，6，12，-12a-四氢苯并[a]噻吩并[2，3-g]喹嗪-8-酮 (26) 和 12-羧基-11-甲基-5，6，12，12a-四氢苯并[a]吡咯并[3，2-g]喹嗪-8 (11H)-one (27)。
• Method of preparing 1-alkyl-3-carboxy-1H pyrrole-2-acetic acids
  申请人：Janssen Pharmaceutica N.V.

  公开号：US04363918A1

  公开（公告）日：1982-12-14

  An improved method of preparing 1-alkyl-3-carboxy-1H-pyrrole-2-acetic acids, the latter compounds being useful intermediates in the preparation of certain anti-inflammatory 1H-pyrrole-2-acetic acids.

  一种改进的制备1-烷基-3-羧基-1H-吡咯-2-乙酸的方法，后者化合物在制备某些抗炎1H-吡咯-2-乙酸中是有用的中间体。
• [EN] SQUARYLIUM COMPOUND, PHOTOELECTRIC CONVERSION MATERIAL USING SAME, PHOTOELECTRIC CONVERTER AND PHOTOELECTROCHEMICAL CELL<br/>[FR] COMPOSE DE SQUARYLIUM, MATERIAU DE CONVERSION PHOTOELECTRIQUE UTILISANT LEDIT COMPOSE, CONVERTISSEUR PHOTOELECTRIQUE ET CELLULE PHOTOELECTROCHIMIQUE
  申请人：KYOWA HAKKO CHEMICAL CO LTD

  公开号：WO2005121127A1

  公开（公告）日：2005-12-22

  Disclosed is a squarylium compound represented by the general formula (I) below (wherein R1 and R3 may be the same or different and respectively represent a hydrogen atom, an optionally substituted alkyl group or the like; R2 represents a hydrogen atom, a carboxyl group, a sulfonic group or the like; R4 represents a hydrogen atom, a hydroxyl group, a halogen atom, an optionally substituted amino group or the like; m represents an integer of 0-2; X represents a nitrogen atom or an oxygen atom; Y represents a nitrogen atom, an oxygen atom or a sulfur atom; A represents an acidic group; n represents an integer of 1-3; and when n is 2 or 3, A's may be the same or different from one another). Also disclosed is a photoelectric conversion material containing such a squarylium compound and a semiconductor.

  本发明涉及一种由下式（I）表示的方苯基化合物（其中R1和R3可以相同或不同，分别表示氢原子，可选取代的烷基或类似物；R2表示氢原子，羧基，磺酸基或类似物；R4表示氢原子，羟基，卤素原子，可选取代的氨基或类似物；m表示0-2的整数；X表示氮原子或氧原子；Y表示氮原子，氧原子或硫原子；A表示酸性基团；n表示1-3的整数；当n为2或3时，A可以相同或不同）。本发明还涉及一种包含此类方苯基化合物和半导体的光电转换材料。