2-氯-1-(2,5-二甲基-1-苯基-1H-吡咯-3-基)-1-乙酮 | 304685-85-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2-氯-1-(2,5-二甲基-1-苯基-1H-吡咯-3-基)-1-乙酮
• 英文名称: 1-(1-phenyl-2,5-dimethyl-1H-pyrrol-3-yl)-2-chloroethanone
• 英文别名: 2-chloro-1-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-1-ethanone；2-chloro-1-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethan-1-one；2-chloro-1-(2,5-dimethyl-1-phenylpyrrol-3-yl)ethanone
• CAS: 304685-85-6
• 化学式: C₁₄H₁₄ClNO
• mdl: MFCD01910939
• 分子量: 247.724
• InChiKey: QSYYGYUKZQOGRQ-UHFFFAOYSA-N

物化性质

• 沸点：
  389.0±37.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.214
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

SDS

Name:	2-Chloro-1-(2 5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-1-ethanone Material Safety Data Sheet
Synonym:	None Known
CAS:	304685-85-6

Section 1 - Chemical Product MSDS Name:2-Chloro-1-(2 5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-1-ethanone Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
304685-85-6	2-Chloro-1-(2,5-dimethyl-1-phenyl-1H-p	97+	unlisted

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Chronic exposure may cause effects similar to those of acute exposure.

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Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid immediately.
Skin:
In case of contact, immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Get medical aid immediately. Wash clothing before reuse.
Ingestion:
If swallowed, do NOT induce vomiting. Get medical aid immediately.
If victim is fully conscious, give a cupful of water. Never give anything by mouth to an unconscious person.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If breathing is difficult, give oxygen. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
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 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. Avoid generating dusty conditions. Provide ventilation. Vacuum or sweep up material and place into a suitable, dry disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing.
Keep container tightly closed. Do not ingest or inhale. Discard contaminated shoes. Use only with adequate ventilation.
Storage:
Keep container closed when not in use. Store in a cool, dry 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# 304685-85-6: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: grey
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 93-94 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: C14H14ClNO
Molecular Weight: 247.72

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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:
Dust generation.
Incompatibilities with Other Materials:
Oxidizing agents, amines, bases.
Hazardous Decomposition Products:
Hydrogen chloride, carbon monoxide, oxides of nitrogen, carbon dioxide, chlorine.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 304685-85-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Chloro-1-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)-1-ethanone - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: Pseudomonas putida:

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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
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing Group: III
IMO
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 22 Do not breathe dust.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
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# 304685-85-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 304685-85-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 304685-85-6 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：

  2-氯-1-(2,5-二甲基-1-苯基-1H-吡咯-3-基)-1-乙酮 、 2-羟基-5-三氟甲基吡啶 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以34%的产率得到CYM-5473
  参考文献：
  名称：

  A sphingosine 1-phosphate receptor 2 selective allosteric agonist

  摘要：

  Molecular probe tool compounds for the Sphingosine 1-phosphate receptor 2 (S1PR2) are important for investigating the multiple biological processes in which the S1PR2 receptor has been implicated. Amongst these are NF-kappa B-mediated tumor cell survival and fibroblast chemotaxis to fibronectin. Here we report our efforts to identify selective chemical probes for S1PR2 and their characterization. We employed high throughput screening to identify two compounds which activate the S1PR2 receptor. SAR optimization led to compounds with high nanomolar potency. These compounds, XAX-162 and CYM-5520, are highly selective and do not activate other SIP receptors. Binding of CYM-5520 is not competitive with the antagonist JTE-013. Mutation of receptor residues responsible for binding to the zwitterionic headgroup of sphingosine 1-phosphate (S1P) abolishes S1P activation of the receptor, but not activation by CYM-5520. Competitive binding experiments with radiolabeled S1P demonstrate that CYM-5520 is an allosteric agonist and does not displace the native ligand. Computational modeling suggests that CYM-5520 binds lower in the orthosteric binding pocket, and that co-binding with SIP is energetically well tolerated. In summary, we have identified an allosteric S1PR2 selective agonist compound. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.012

文献信息

• Synthesis of α-Alkylated β-Ketoesters by Alkoxycarbonylation/Michael Addition Domino Reaction
  作者：Benoit Wahl、Yann Philipson、Hélène Bonin、André Mortreux、Mathieu Sauthier

  DOI：10.1021/jo3026143

  日期：2013.2.15

  palladium-catalyzed alkoxycarbonylation of an α-chloro ketone can be efficiently combined to a Michael addition reaction in a new two-step domino reaction, allowing the synthesis of original highly functionalized α-alkylated β-ketoesters. The scope of the reaction was extended to several α-chloro ketones and Michael acceptors with moderate to very good yields.

  钯催化的α-氯酮的烷氧基羰基化可以在新的两步多米诺反应中有效地与迈克尔加成反应结合，从而可以合成原始的高度官能化的α-烷基化β-酮酸酯。反应范围扩大到了几种α-氯代酮和迈克尔受体，产率中等至非常好。
• Straightforward Synthesis of Allylated Keto Esters: The Palladium-Catalysed Haloketone Alkoxycarbonylation/ Allylation Domino Reaction
  作者：Benoit Wahl、Steven Giboulot、André Mortreux、Yves Castanet、Mathieu Sauthier、Frédéric Liron、Giovanni Poli

  DOI：10.1002/adsc.201100848

  日期：2012.4.16

  The palladium‐catalysed α‐chloro ketone methoxycarbonylation and allylic alkylation reactions can be efficiently combined to provide a new catalytic domino reaction. The first, carbonylative, step generates the β‐keto ester, which acts as the nucleophile in a subsequent allylation step. The use of allyl phenates in combination with Xantphos ligand are the key features allowing one to obtain the allylated

  钯催化的α-氯酮甲氧基羰基化反应和烯丙基烷基化反应可以有效地结合以提供新的催化多米诺反应。第一步是羰基化反应，生成β-酮酸酯，后者在随后的烯丙基化步骤中充当亲核试剂。烯丙基酚盐与Xantphos配体结合使用是关键特征，使人们能够以高收率获得烯丙基化的β-酮酯
• PROTEOSTASIS REGULATORS
  申请人：Foley Megan

  公开号：US20120316193A1

  公开（公告）日：2012-12-13

  The present invention is directed to compounds having the Formulae (Ia-Ie), (II), (IIIa-IIId), (IVa-IVc), (Va-Vb), (VIa-VIe), (VII), (VIIIa-VIIIc), and (IX), pharmaceutically acceptable salts, prodrugs and solvates thereof, compositions of any of thereof and methods for the treatment of a condition associated with a dysfunction in proteostasis comprising an effective amount of these compounds.

  本发明涉及具有化学式(Ia-Ie)、(II)、(IIIa-IIId)、(IVa-IVc)、(Va-Vb)、(VIa-VIe)、(VII)、(VIIIa-VIIIc)和(IX)的化合物，以及这些化合物的药用可接受盐、前药和溶剂合物，以及这些化合物的任何组合物，并且用于治疗与蛋白质稳态功能紊乱相关的疾病的方法，包括有效量的这些化合物。
• AZASPIRO DERIVATIVES AS TRPM8 ANTAGONISTS
  申请人：RaQualia Pharma Inc.

  公开号：US20170002016A1

  公开（公告）日：2017-01-05

  The present invention relates to azaspiro derivatives of the formula (I) or a pharmaceutically acceptable salt thereof or a prodrug thereof, processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of various disorders which are mediated via the TRPM8 receptor.
• PROTEASOME ACTIVITY ENHANCING COMPOUNDS
  申请人：Proteostasis Therapeutics, Inc.

  公开号：US20210115057A1

  公开（公告）日：2021-04-22

  The present invention is directed to compounds having the Formulae (Ia), (Ib), (Ic), or (Id); or the Formulae (II), (IIa), (IIb), or (IIc); or the Formulae (III), (IIIa), (IIIb), (IIIc), (IIId), or (IIIe), and pharmaceutically acceptable salts, solvates, clathrates and prodrugs of any Formula thereof, compositions thereof, and methods for the treatment of a condition associated with a dysfunction in proteostasis.