6-氯-9-乙基-9H-嘌呤 | 5462-86-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 6-氯-9-乙基-9H-嘌呤
• 英文名称: 6-chloro-9-ethyl-9H-purine
• 英文别名: 6-chloro-9-ethylpurine
• CAS: 5462-86-2
• 化学式: C₇H₇ClN₄
• mdl: MFCD07440136
• 分子量: 182.612
• InChiKey: YSKHRCGNQFWRFM-UHFFFAOYSA-N

物化性质

• 熔点：
  77-79 °C ()
• 沸点：
  326.9±45.0 °C (Predicted,Press: 760 Torr)
• 密度：
  1.50±0.1 g/cm³ (Predicted,Temp: 20 °C; Press: 760 Torr)
• pKa：
  1.25±0.10 (Predicted,Most Basic Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 储存条件：
  室温

SDS

Name:	6-Chloro-9-Ethyl-9H-Purine Material Safety Data Sheet
Synonym:	None Known
CAS:	5462-86-2

Section 1 - Chemical Product MSDS Name:6-Chloro-9-Ethyl-9H-Purine Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5462-86-2	6-Chloro-9-Ethyl-9H-Purine	ca. 100	unlisted

Hazard Symbols: T
Risk Phrases: 23/24/25 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Toxic by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. Toxic in contact with skin.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated. Toxic if swallowed.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Toxic if inhaled.
Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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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.
Skin:
Get medical aid immediately. Immediately 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 immediately. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Do NOT use mouth-to-mouth resuscitation.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam. Use agent most appropriate to extinguish fire.

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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. Do not get in eyes, on skin, or on clothing. Keep container tightly closed. Do not ingest or inhale. Discard contaminated shoes.
Storage:
Keep container closed when not in use. 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# 5462-86-2: 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: Not available.
Color: Not available.
Odor: Not available.
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: C7H7ClN4
Molecular Weight: 182.61

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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:
Incompatible materials, excess heat.
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: Not available.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 5462-86-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
6-Chloro-9-Ethyl-9H-Purine - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Products which are considered hazardous for supply are classified as Special Waste and the disposal of such chemicals is covered by regulations which may vary according to location. Contact a specialist disposal company or the local waste regulator for advice. Empty containers must be decontaminated before returning for recycling.

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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: T
Risk Phrases:
R 23/24/25 Toxic by inhalation, in contact with skin
and if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 5462-86-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 5462-86-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5462-86-2 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：

  6-氯-9-乙基-9H-嘌呤 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 sodium hydride 、 potassium carbonate 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 mineral oil 为溶剂， 反应 17.75h， 生成 (S)-9-ethyl-8-(2-methylpyrimidin-5-yl)-6-(pyrrolidin-3-yloxy)-9H-purine
  参考文献：
  名称：

  [EN] PURINE INHIBITORS OF HUMAN PHOSPHATIDYLINOSITOL 3-KINASE DELTA
  [FR] INHIBITEURS PURIQUES DE LA PHOSPHATIDYLINOSITOL 3-KINASE DELTA HUMAINE

  摘要：

  本发明提供了一种公式I的化合物，这些化合物是PI3K-δ抑制剂，因此可用于治疗PI3K-δ介导的疾病，如炎症、哮喘、慢性阻塞性肺疾病和癌症。

  公开号：

  WO2014075392A1
• 作为产物：
  描述：

  在 magnesium chloride 作用下， 以 乙腈 为溶剂， 生成 6-氯-9-乙基-9H-嘌呤
  参考文献：
  名称：

  氨基杂环的脱氨基氯化

  摘要：

  对含杂原子芳族结构的选择性修饰需求量很大，因为它可以快速评估高级中间体中的分子复杂性。受自然界中脱氨酶选择性的启发，本文提出了一种简单的方法，可以将氨基杂环中的 NH 2基团视为掩蔽修饰句柄。借助简单的吡喃试剂和廉价的氯化物源，C( sp 2 )-NH 2可以转化为 C( sp 2)-Cl 键。该方法的特点是其广泛的官能团耐受性和底物范围，允许修饰超过 20 种不同类别的杂芳基基序（五元和六元杂环），具有许多敏感基序。NH 2以后期方式轻松转化为Cl，使从业者能够应用Sandmeyer-和Vilsmeier-型转化，而没有爆炸性和不安全的重氮盐、化学计量过渡金属或高氧化性和非选择性氯化剂的负担。

  DOI：

  10.1038/s41557-021-00812-0

文献信息

• Purines. LIV. Intramolecular Cyclization of 9-Ethyl-1-(2-hydroxyethyl)adenine Caused by Nucleophiles: Formation of N6, 1-Ethanoadenine Derivatives.
  作者：Tohru SAITO、Miyoko MURAKAMI、Tadaaki INADA、Hiromi HAYASHIBARA、Tozo FUJII

  DOI：10.1248/cpb.41.453

  日期：——

  Treatment of 9-ethy-1-(2-hydroxythyl)adenide hydrobromide (1a) in boiling N, N-dimethylformamide (DMF) with an excess of thiourea for 7 h or with an excess of ammonium thiocyanate for 3 h provided 3-ethyl-7, 8-dihydro-3H-imidazo[2, 1-i]purinium thiocyanate (8) in 51% or 58% yield, respectively. On treatment with an excess of triphenyl phosphite in boiling DMF for 20 min, 1 a underwent a similar cyclization to from the same tricycle, which was isolated in 81% yield (from 1 a)in the form of the perchlorate salt (12). A similar treatment of 1 a with triethyl phosphite furnished the 9-ethyl analogue (15) in 83% yield. Conversion of 12 into the free base and oxidation of latter with active MnO2 in boiling CH2Cl2 for 16 h gave 3-ethyl 3-ethyl-3H-imidazo[2, 1-i]purine (13) (66% overall yield from 12), which was identical with a sample synthesized from 9-ethyladenine (9) and chloroacetaldehyde according to the general N6, 1-etheno bridgeing procedure. On treatment with methanolic ammonia at room temperature, the tricycle 15 afforded 9-ethyl-N6-[2-(ethylamino)ethyl]adenine hydrobromide (26) in 79% yield. Mechanisms are proposed for the above intramolecular cyclizations of 1 a caused by the S- and P-atom nucleophiles.

  在沸腾的N,N-二甲基甲酰胺（DMF）中，将9-乙基-1-（2-羟乙基）腺嘌呤氢溴酸盐（1a）与过量的硫脲反应7小时，或与过量的硫氰酸铵反应3小时，分别以51%或58%的产率得到3-乙基-7,8-二氢-3H-咪唑并[2,1-i]嘌呤硫氰酸盐（8）。在沸腾的DMF中，将1a与过量的三苯基膦反应20分钟，经历类似的环化反应，生成相同的 Tricycle，以81%的产率（从1a开始）分离得到高氯酸盐形式（12）。将1a与三乙基膦反应得到9-乙基类似物（15），产率为83%。将12转化为自由碱，并在沸腾的CH2Cl2中用活性MnO2氧化16小时，得到3-乙基-3H-咪唑并[2,1-i]嘌呤（13）（从12开始的总产率为66%），与根据N6,1-乙烯桥接法由9-乙基腺嘌呤（9）和氯乙醛合成的样品相同。在室温下用甲醇氨处理三环化合物15，以79%的产率得到9-乙基-N6-[2-（乙胺基）乙基]腺嘌呤氢溴酸盐（26）。上述1a分子内环化过程由S和P原子亲核试剂引起的机制被提出。
• 一种含SCF
  申请人：中国海洋大学

  公开号：CN111333651B

  公开（公告）日：2022-05-10

  本发明公开了一种含SCF3或SeCF3的杂环化合物及其制备方法，氯代杂环化合物1溶于EtOH溶液后，加入1.0‑2.0倍当量的硫脲或硒脲，然后在50‑120℃条件下搅拌1‑8小时，反应得到化合物2；将化合物2溶于Acetone或EA溶液后，加入2.0‑4.0倍当量的CF3SO2Na，0.2‑0.4倍当量Cu盐，然后逐滴加入2.0‑4.0倍当量的tBuOOH溶液，在25‑40℃条件下反应1.0‑2.0小时，得到化合物3，即所需的含SCF3或SeCF3的杂环化合物。本发明合成的化合物在治疗疾病方面存在巨大的潜力，本发明的合成路线每一个步骤都可以实现放大，收率可以达到85％，本发明提供的合成路线为具有生物活性的化合物的合成带来一条更为简洁有效的途径，收率高，可大规模制备，具有很广阔的应用前景。
• CuI Controlled C–C and C–N Bond Formation of Heteroaromatics through C(sp³)–H Activation
  作者：Ran Xia、Hong-Ying Niu、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1021/ol302640e

  日期：2012.11.2

  A new method for C–C and C–N bond formation of heteroaromatics and C(sp3)–H alkanes was developed with high regioselectivity. The reaction occurred on C8 to give 8-cylcoakylpurines by C–C bond formation only promoted by tBuOOtBu, while it occurred on the amino group to give N6-alkylated purines by C–N bond formation when 2 equiv of CuI were added. A reaction mechanism was also proposed based on our

  具有高区域选择性的杂芳烃和C（sp 3）-H烷烃的C–C和C–N键形成的新方法得到了发展。该反应发生在C8上，仅通过t BuOO t Bu促进了通过C–C键形成的8烷基甲酰基嘌呤，而当氨基当上，当2当量的CuI为2时，通过C–N键的形成产生了N 6烷基化的嘌呤。添加。根据我们的初步实验数据，还提出了一种反应机理。
• 含嘌呤环的苯磺酰胺查尔酮类衍生物、其制备方法及用途
  申请人：贵州大学

  公开号：CN108892668A

  公开（公告）日：2018-11-27

  本发明公开了一种含嘌呤环的苯磺酰胺查尔酮类衍生物、其制备方法及用途，具有以下的通式（I）：式中：R1为4‑氧甲基、4‑叔丁基、4‑甲基、4‑氟、4‑氯、4‑溴、2‑甲基、2‑氟、2‑氯、2‑溴、和氢原子；R2为甲基、乙基、苄基。本发明能抑制抗烟草花叶病毒、黄瓜花叶病毒和马铃薯Y病毒和南方水稻黑条矮缩病毒的含嘌呤环。
• Synthesis of C6-azolyl purine nucleosides via C–N coupling reaction of unprotected 6-chloropurine nucleosides and N-heterocycles under catalyst- and solvent-free conditions
  作者：Gui-Rong Qu、Hong-Liang Zhang、Hong-Ying Niu、Zai-Kun Xue、Xin-Xin Lv、Hai-Ming Guo

  DOI：10.1039/c2gc35419e

  日期：——

  C6-azolyl purine nucleoside products are prepared in high yields under solvent- and catalyst-free conditions via C–N coupling reaction of unprotected 6-chloropurine nucleosides and N-heterocycles, providing a unifying, simple and environmentally friendly complement to the available methods.

  在无溶剂和催化剂的条件下，通过未保护的6-氯嘌呤核苷和N-杂环之间的C-N偶联反应，可以高产率地制备C6-唑基嘌呤核苷产物，为现有的方法提供了一种统一、简单且环境友好的补充。

表征谱图