1-(2,3-二甲基苯基)哌啶 | 1013-22-5

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 1-(2,3-二甲基苯基)哌啶
• 中文别名: 1-(2,3-二甲基苯基)哌嗪
• 英文名称: 1-(2,3-dimethylphenyl)piperazine
• 英文别名: 2,3-dimethylphenylpiperazine；4-(2,3-dimethylphenyl)piperazine
• CAS: 1013-22-5
• 化学式: C₁₂H₁₈N₂
• mdl: MFCD00040730
• 分子量: 190.288
• InChiKey: LIKXJDINUMWKQA-UHFFFAOYSA-N

物化性质

• 沸点：
  95 °C
• 密度：
  1.031
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• 稳定性/保质期：
  常温常压下稳定，避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  C
• 安全说明：
  S23,S26,S36/37/39,S45
• 危险类别码：
  R21/22,R34
• 海关编码：
  2933599090
• 储存条件：
  请将容器密封保存，并储存在阴凉、干燥的地方。

SDS

Name:	1-(2 3-Dimethylphenyl)piperazine 99% Material Safety Data Sheet
Synonym:
CAS:	1013-22-5

Section 1 - Chemical Product MSDS Name:1-(2 3-Dimethylphenyl)piperazine 99% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1013-22-5	1-(2,3-Dimethylphenyl)piperazine	99	213-794-0

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:
May cause eye irritation. The toxicological properties of this material have not been fully investigated.
Skin:
May cause skin irritation. The toxicological properties of this material have not been fully investigated.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause 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: 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. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use only in a well-ventilated area. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1013-22-5: 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: Viscous liquid
Color: clear yellow
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
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: C12H18N2
Molecular Weight: 190.29

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1013-22-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-(2,3-Dimethylphenyl)piperazine - 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 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# 1013-22-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1013-22-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1013-22-5 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

制备方法与用途

概述

1-(2,3-二甲基苯基)哌啶可用作医药合成中间体。如吸入此物质，请将患者移至新鲜空气处；若皮肤受到污染，请脱去受污染的衣物，并用肥皂水和清水彻底清洗皮肤，如有不适，请就医；若眼睛接触到该物质，请翻开眼睑，用流动清水或生理盐水冲洗，并立即就医；若吞食，请立即漱口，禁止催吐，并尽快就医。

反应信息

• 作为反应物：
  描述：

  1-(2,3-二甲基苯基)哌啶 在 Ra-Ni sodium carbonate 、 一水合肼 、 potassium iodide 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 4-[2-(3,4-diaminophenyl)-ethyl]-1-(2,3-dimethylphenyl)piperazine
  参考文献：
  名称：

  Dukic, Sladjana; Vujovic, Miroslava; Soskic, Vukic, Arzneimittel-Forschung/Drug Research, 1997, vol. 47, # 3, p. 239 - 243

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(2,3-dimethylphenyl)piperazine hydrochloride 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.5h， 以96%的产率得到1-(2,3-二甲基苯基)哌啶
  参考文献：
  名称：

  设计，合成和生物学评估结构受限的杂种类似物，其中包含罗匹尼罗部分作为新型强效和选择性多巴胺D3受体配体

  摘要：

  设计，合成和评估了两个系列的杂合类似物，作为多巴胺D3受体的一类新的选择性配体。确定目标化合物的结合亲和力（使用放射性配体结合测定法）。与比较剂BP897相比，发现化合物2a和2c对D3受体表现出相当大的结合亲和力和选择性，尤其是化合物2h与BP897（正参比）具有相似的效力和更高的D3R配体。因此，它们可以为发现和开发具有出色选择性的高效多巴胺D3受体配体提供有价值的信息。

  DOI：

  10.1111/cbdd.13324
• 作为试剂：
  描述：

  (2R)-quinaldine dioxine brosylate 在 1-(2,3-二甲基苯基)哌啶 作用下， 以 anhydrous DMSO 为溶剂， 反应 24.0h， 以90%的产率得到(2S)-2-{[4-(2,3-dimethylphenyl)piperazin-1-yl]methyl}-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinoline
  参考文献：
  名称：

  [EN] ANTIDEPRESSANT ARYLPIPERAZINE DERIVATIVES OF HETEROCYCLE-FUSED BENZODIOXANS
  [FR] DERIVES ARYLPIPERAZINES ANTIDEPRESSEURS DE BENZODIOXANES A FUSION HETEROCYCLIQUE

  摘要：

  公式I的化合物对治疗抑郁症（包括但不限于重性抑郁障碍、儿童抑郁症和心境恶劣障碍）、焦虑症、恐慌障碍、创伤后应激障碍、经前期情感障碍（也称为经前综合征）、注意力缺陷障碍（伴有和不伴有多动症）、强迫症、社交焦虑障碍、广泛性焦虑障碍、肥胖、厌食症和暴食症等进食障碍、血管运动性潮红、可卡因和酒精成瘾、性功能障碍及相关疾病方面具有用处。

  公开号：

  WO2004024731A1

文献信息

• Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor
  申请人：——

  公开号：US20040157849A1

  公开（公告）日：2004-08-12

  Compounds of formula (I) 1 are novel VR1 antagonists that are useful in treating pain, inflammatory thermal hyperalgesia, urinary incontinence and bladder overactivity.

  式（I）的化合物是新颖的VR1拮抗剂，可用于治疗疼痛、炎症性热性过敏、尿失禁和膀胱过度活动。
• [EN] 1-ARYL-4-SUBSTITUTED PIPERAZINES DERIVATIVES FOR USE AS CCR1 ANTAGONISTS FOR THE TREATMENT OF INFLAMMATION AND IMMUNE DISORDERS<br/>[FR] DERIVES DE PIPERAZINES 1-ARYL-4-SUSBTITUES UTILISES EN TANT QU'ANTAGONISTES DU CCR1 DANS LE TRAITEMENT DE L'INFLAMMATION ET DES TROUBLES IMMUNITAIRES
  申请人：CHEMOCENTRYX INC

  公开号：WO2003105853A1

  公开（公告）日：2003-12-24

  Compounds are provided that act as potent antagonists of the CCR1 receptor, and which have been further confirmed in animal testing for inflammation, one of the hallmark disease states for CCR1. The compounds are generally aryl piperazine derivatives and are useful in pharmaceutical compositions, methods for the treatment of CCR1-mediated diseases, and as controls in assays for the identification of competitive CCR1 antagonists.

  提供了作为CCR1受体强效拮抗剂的化合物，并且已经在动物炎症测试中进一步确认，炎症是CCR1的典型疾病状态之一。这些化合物通常是芳基哌嗪衍生物，在制药组合物、治疗CCR1介导疾病的方法以及用于鉴定竞争性CCR1拮抗剂的检测中具有用途。
• Arylpiperazine Derivatives and their Use as Selective Dopamine D3 Receptor Ligands
  申请人：Capet Marc

  公开号：US20080214542A1

  公开（公告）日：2008-09-04

  The invention concerns compounds of general formula (I), a method for preparing same, as well as their use as therapeutic agent.

  这项发明涉及一般式（I）的化合物，以及制备这些化合物的方法，以及它们作为治疗剂的用途。
• New potent 5-HT2A receptor ligands containing an N′-cyanopicolinamidine nucleus: Synthesis and in vitro pharmacological evaluation
  作者：Ferdinando Fiorino、Beatrice Severino、Elisa Magli、Elisa Perissutti、Francesco Frecentese、Antonella Esposito、Giuseppina Maria Incisivo、Antonio Ciano、Paola Massarelli、Cristina Nencini、Vincenzo Santagada、Giuseppe Caliendo

  DOI：10.1016/j.ejmech.2011.11.023

  日期：2012.1

  N′-cyanopicolinamidine derivatives, linked to an arylpiperazine moiety, were prepared and their affinity to serotonin 5-HT1A, 5-HT2A and 5-HT2C receptors were evaluated. The combination of structural elements (heterocyclic nucleus, alkyl chain and 4-substituted piperazine) known to be critical for affinity to 5-HT1A receptors and the proper selection of substituents led to compounds with high specificity

  制备与芳基哌嗪部分连接的N'-氰基吡啶啉am衍生物，并评估它们对5-羟色胺5-HT 1A，5-HT 2A和5-HT 2C受体的亲和力。已知对5-HT 1A受体的亲和力至关重要的结构元素（杂环核，烷基链和4-取代的哌嗪）的组合以及对取代基的正确选择导致了对5-羟色胺能受体具有高特异性和亲和力的化合物。在结合研究中，几个分子在5-HT 2A处显示出纳摩尔和亚纳摩尔范围内的亲和力，而对其他相关受体（5-HT 1A，5-HT 2C，D 1，D2，α 1和α 2）。K i  = 0.000185 nM的N'-氰基-N-（3-（4-（3-氯苯基）哌嗪-1-基）丙基）-吡啶啉olin （4l）是5-HT活性最高的选择性衍生物2A受体与其他5-羟色胺，多巴胺能和肾上腺素能受体相比。
• Compounds having effects on serotonin-related systems
  申请人：Eli Lilly and Company

  公开号：US05741789A1

  公开（公告）日：1998-04-21

  A series of hetero-oxy alkanamines are effective pharmaceuticals for the treatment of conditions related to or affected by the reuptake of serotonin and by the serotonin 1.sub.A receptor. The compounds are particularly useful for alleviating the symptoms of nicotine and tobacco withdrawal, and for the treatment of depression and other conditions for which serotonin reuptake inhibitors are used.

  一系列的杂氧烷胺类化合物是治疗与血清素再摄取和血清素1A受体有关或受其影响的疾病的有效药物。这些化合物特别适用于缓解尼古丁和烟草戒断症状，以及治疗抑郁症和其他需要使用血清素再摄取抑制剂的疾病。