1-(3-氯苯基-4-氯丙基)哌嗪盐酦盐 | 39577-43-0

• 物质功能分类: 医药中间体 - 杂环化合物
• 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-(3-氯苯基-4-氯丙基)哌嗪盐酦盐
• 中文别名: 1-(3-氯苯基)-4-(3-氯丙基)哌嗪；1-(3-氯苯基)-4-氯丙基哌嗪
• 英文名称: 1-(3-chloropropyl)-4-(3-chlorophenyl)piperazine
• 英文别名: 1-(3-chlorophenyl)-4-(3-chloropropyl)piperazine；1-(m-chlorophenyl)-4-(3-chloropropyl)piperazine；4-(m-Chlorophenyl)-1-(3-chloropropyl)piperazine；1-(3-chloro-n-propyl)-4-(3-chlorophenyl)-piperazine
• CAS: 39577-43-0
• 化学式: C₁₃H₁₈Cl₂N₂
• mdl: MFCD01026118
• 分子量: 273.205
• InChiKey: NDQKGEFMUGSRNS-UHFFFAOYSA-N

物化性质

• 熔点：
  199 °C
• 沸点：
  157-162 °C(Press: 0.5 Torr)
• 密度：
  1.186
• LogP：
  3.64
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R20/21/22
• 危险品运输编号：
  OTH
• 海关编码：
  2933599090
• 安全说明：
  S24/25
• 储存条件：
  存储于阴凉干燥处。

SDS

Name:	1-(3-Chlorophenyl)-4-(3-Chloropropyl)piperazine Hydrochloride Material Safety Data Sheet
Synonym:	None known
CAS:	39577-43-0

Section 1 - Chemical Product MSDS Name:1-(3-Chlorophenyl)-4-(3-Chloropropyl)piperazine Hydrochloride Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
39577-43-0	1-(3-Chlorophenyl)-4-(3-Chloropropyl)p	97	254-529-9

Hazard Symbols: XN
Risk Phrases: 20/21/22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. 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.
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.
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:
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:
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# 39577-43-0: 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: beige
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 applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C13H18Cl2N2.HCl
Molecular Weight: 309.65

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, nitrogen oxides, 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# 39577-43-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-(3-Chlorophenyl)-4-(3-Chloropropyl)piperazine Hydrochloride - 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: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
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# 39577-43-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 39577-43-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 39577-43-0 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

化学性质：白色或浅白色结晶粉末，熔点为199～204℃。

用途：它是合成奈法唑酮、依托哌酮和曲唑酮的重要中间体。

反应信息

• 作为反应物：
  描述：

  1-(3-氯苯基-4-氯丙基)哌嗪盐酦盐 生成 1-(3-chlorophenyl)-4-(3-hydrazinopropyl)piperazine
  参考文献：
  名称：

  TEMPLE, D. L. ,, JR.;LOBECK, W. G. ,, JR.

  摘要：

  DOI：
• 作为产物：
  描述：

  盐酸曲唑酮杂质 在 三苯基膦 作用下， 以 四氯化碳 为溶剂， 以70%的产率得到1-(3-氯苯基-4-氯丙基)哌嗪盐酦盐
  参考文献：
  名称：

  Synthesis of 2-phenylthiazolidine derivatives as cardiotonic agents. II. 2-(Phenylpiperazinoalkoxyphenyl)thiazolidine-3-thiocarboxamides and the corresponding carboxamides.

  摘要：

  大量2-（苯基哌嗪基烷氧苯基）噻唑烷-3-硫代羧酰胺及其相应羧酰胺（II）被合成并在麻醉犬中测试其强心活性。化合物II通过羟基苯甲醛（III）及其中间体（IV、V和X）制备。通过改变结构参数来研究结构-活性关系（SAR）。将哌嗪基烷氧基团从邻位位置移至间位或对位导致活性显著下降。将硫代羧酰胺转变为羧酰胺基团导致活性显著增加。这种趋势在这一系列化合物中普遍存在，并构成与简单2-苯基噻唑烷系列SAR的主要偏离。关于氨基烷氧链长度的影响，乙氧基衍生物通常比更高级的类似物更有效。在（硫代）羧酰胺基团中延长N-烷基通常导致活性下降。在合成的各种衍生物中，II15被发现其效力约为氨力农的一百倍，且作用时间较长。

  DOI：

  10.1248/cpb.35.2394

文献信息

• N-Aryl-N-phenoxy-alkyl-piperazine compounds useful in decreasing
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：US04413006A1

  公开（公告）日：1983-11-01

  A piperazine derivative of the formula: ##STR1## wherein R.sup.1 is hydrogen, alkyl (C.sub.1-8), alkyl (C.sub.1-4)-sulfonyl or an acyl group of the formula: R.sup.3 CO--(wherein R.sup.3 is hydrogen, alkyl (C.sub.1-7), halogenoalkyl (C.sub.1-4), alkoxy (C.sub.1-4)-carbonyl-alkyl (C.sub.1-4), cycloalkyl (C.sub.3-6), alkenyl (C.sub.2-5), alkoxy (C.sub.1-4), amino, alkyl (C.sub.1-4)-amino or anilino), R.sup.2 is hydrogen, alkyl (C.sub.1-4), alkoxy (C.sub.1-4)-carbonyl-alkyl (C.sub.1-4), carboxy-alkyl (C.sub.1-4), alkenyl (C.sub.2-5) or alkyl (C.sub.1-4)-sulfonyl, or R.sup.1 and R.sup.2 are combined together to form succinyl group, Ring A is phenyl, alkyl (C.sub.1-4)-phenyl or halogenophenyl, and n is an integer of 2 to 6, or a pharmaceutically acceptable acid addition salt thereof. The piperazine derivative (I) has an intracranial pressure-lowering activity. Said derivative also has a depressing effect on central nervous system.

  一种化学式为：##STR1##的哌嗪衍生物，其中R.sup.1为氢、烷基（C.sub.1-8）、烷基（C.sub.1-4）-磺酰基或化学式为R.sup.3 CO-的酰基（其中R.sup.3为氢、烷基（C.sub.1-7）、卤代烷基（C.sub.1-4）、烷氧基（C.sub.1-4）-羰基-烷基（C.sub.1-4）、环烷基（C.sub.3-6）、烯基（C.sub.2-5）、烷氧基（C.sub.1-4）、氨基、烷基（C.sub.1-4）-氨基或苯胺基），R.sup.2为氢、烷基（C.sub.1-4）、烷氧基（C.sub.1-4）-羰基-烷基（C.sub.1-4）、羧基-烷基（C.sub.1-4）、烯基（C.sub.2-5）或烷基（C.sub.1-4）-磺酰基，或R.sup.1和R.sup.2结合形成琥珀酰基，环A为苯基、烷基（C.sub.1-4）-苯基或卤代苯基，n为2至6的整数，或其药学上可接受的酸盐。该哌嗪衍生物（I）具有降低颅内压的活性。该衍生物还对中枢神经系统具有抑制作用。
• Design, synthesis, and biological evaluation of arylpiperazine–benzylpiperidines with dual serotonin and norepinephrine reuptake inhibitory activities
  作者：Suresh Paudel、Srijan Acharya、Kyeong-Man Kim、Seung Hoon Cheon

  DOI：10.1016/j.bmc.2016.03.044

  日期：2016.5

  The limitations of established serotonin (5-hydroxytryptamine, 5-HT) and norepinephrine (NE) reuptake inhibitors necessitate the development of safer and more effective therapeutic agents. Based on the structures of 4-benzylpiperidine carboxamides and trazodone, arylpiperazine–benzylpiperidines with chemical scaffolds different from those of marketed drugs were designed, synthesized, and evaluated

  既定的5-羟色胺（5-羟色胺，5-HT）和去甲肾上腺素（NE）再摄取抑制剂的局限性需要开发更安全，更有效的治疗剂。根据4-苄基哌啶羧酰胺和曲唑酮的结构，设计，合成和评估化学支架与市售药物不同的芳基哌嗪-苄基哌啶，并评估其对神经递质再摄取的抑制活性。大多数合成化合物显示出比5-HT再摄取抑制更大的NE。其活性甚至大于标准药物盐酸文拉法辛。具有三碳连接基的衍生物表现出比具有二碳连接基的衍生物更好的活性。在新合成的化合物中，第2d表现出最强的神经递质再摄取抑制作用（ NE的IC 50 = 0.38μM，5-HT的IC 50 = 1.18μM）。生物学活性数据表明，芳基哌嗪-苄基哌啶具有开发作为治疗神经精神病和神经退行性疾病的新型治疗剂的潜力。
• Synthesis of New S-alkylated-3-mercapto-1,2,4-triazole Derivatives Bearing Cyclic Amine Moiety as Potent Anticancer Agents
  作者：M. S.R. Murty、Kesur R. Ram、Rayudu Venkateswara Rao、J. S. Yadav、Janapala Venkateswara Rao、L. R. Velatooru

  DOI：10.2174/157018012799129882

  日期：2012.3.1

  A series of 3-[3-[4-(Substituted)-1-cyclicamine]propyl]thio-5-substituted[1,2,4]triazoles (8a-j) were synthesized with good yields starting from corresponding carboxylic acids. The cytotoxicity studies of these derivatives were studied against five different human cancer cell lines. Three compounds had shown good anticancer activity. The triazole derivatives, 8i and 8j were most potent particularly against U937 and HL-60 cells. The cytotoxic potency of the compounds varied between the cell lines suggesting that a structural property of these compounds as possible determinants of their biological activity.

  一系列3-[3-[4-(取代)-1-环胺]丙基]硫-5-取代[1,2,4]三唑(8a-j)，从相应的羧酸出发，以良好的收率被合成。这些衍生物对五种不同的人类癌细胞系进行了细胞毒性研究。三种化合物显示出良好的抗癌活性。三唑衍生物，8i和8j，对U937和HL-60细胞尤其有效。化合物的细胞毒性效力在不同细胞系之间有所变化，这表明这些化合物的结构特性可能是其生物活性的可能决定因素。
• Synthesis and preliminary evaluation activity studies of novel 4-(aryl/heteroaryl-2-ylmethyl)-6-phenyl-2-[3-(4-substituted-piperazine-1-yl)propyl]pyridazin-3(2H)-one derivatives as anticancer agents
  作者：M. S. R. Murty、B. Ramalingeswara Rao、Kesur R. Ram、J. S. Yadav、Jayesh Antony、Ruby John Anto

  DOI：10.1007/s00044-011-9851-6

  日期：2012.10

  A series of new 4-(aryl/heteroaryl-2-ylmethyl)-6-phenyl-2-[3-(4-substituted piperazine-1-yl)propyl] pyridazin-3(2H)-one derivatives were synthesized. The structures of the compounds were confirmed by IR, 1H NMR, and mass spectral data. All the compounds were evaluated for their cytotoxicity toward five human cancer cell lines of different origins viz; HeLa (Cervical), SKBR3 (Breast), HCT116 (Colon)

  合成了一系列新的4-（芳基/杂芳基-2-基甲基）-6-苯基-2- [3-（4-取代的哌嗪-1-基）丙基]哒嗪-3（2H）-衍生物。化合物的结构通过IR，1 H NMR和质谱数据证实。评价所有化合物对五种不同来源的人类癌细胞系的细胞毒性。HeLa（宫颈），SKBR3（乳腺癌），HCT116（结肠），A375（皮肤）和H1299（肺）处于不同浓度，并测定了IC 50值。HCT116和HeLa对研究的化合物最敏感。其中之一显示出对SKBR3的中等细胞毒性。大多数化合物表现出良好至中等的活性。
• Synthesis and antiproliferative activity of basic thioanalogues of merbarone
  作者：Angelo Ranise、Andrea Spallarossa、Silvia Schenone、Olga Bruno、Francesco Bondavalli、Alessandra Pani、Maria Elena Marongiu、Valeria Mascia、Paolo La Colla、Roberta Loddo

  DOI：10.1016/s0968-0896(03)00158-5

  日期：2003.6

  12a-c,g-j, 13e,f,h and 14k were inactive. Cytotoxicity data provided from N.C.I. on selected compounds provided evidence that 11b,d, 13d,g and 14b,d,f,h,i,j were endowed with potent antiproliferative activity against leukemia and prostate cell lines (GI(50) up to 0.01 microM). In general, bicyclic derivatives 14 were up to 10-fold more potent than monocyclic counterparts against solid tumor-derived cell

  合成了三个系列的5个取代的1,3-二苯基-6-（ω-二烷基-和ω-环氨基烷基）硫代-2-硫代巴比妥酸酯（11-13）作为Merbarone的多取代硫代类似物，merbarone是一种作用于拓扑异构酶II的抑制剂催化部位。为了更好地理解药效基团的需求，还制备了第四系列构象受限的类似物14。衍生物11b，e，14b，e，h，i，j在低微摩尔浓度范围内具有活性（IC（50）：3.3-4.3 microM），而化合物11a，c，d，f，h，j和13a， b，d，g，j和14a，d，f显示的IC（50）值介于10和15.5 microM之间。相反，化合物12a-c，gj，13e，f，h和14k没有活性。NCI提供的有关选定化合物的细胞毒性数据提供了证据，表明11b，d，13d，g和14b，d，f，h，i，j被赋予针对白血病和前列腺细胞系的有效抗增殖活性（GI（50）高达0.01 microM）。通常