6-氨基-5-亚硝基-2-硫脲嘧啶 | 1672-48-6

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 6-氨基-5-亚硝基-2-硫脲嘧啶
• 中文别名: 4-氨基-6-羟基-2-巯基-5-亚硝基嘧啶
• 英文名称: 4-Amino-5-nitroso-6-oxo-1,2,3,6-tetrahydro-2-thiopyrimidine
• 英文别名: 6-amino-5-nitroso-2-thioxo-2,3-dihydropyrimidin-4(1H)-one；6-amino-5-nitroso-2-thioxo-1,2-dihydro4(3H)-pyrimidinone；6-amino-5-nitroso-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one；4-amino-6-hydroxy-2-mercapto-5-nitrosopyrimidine；6-amino-5-nitroso-2-thiouracil；5-Isonitroso-4-amino-2-thiouracil；6-amino-5-nitroso-2-sulfanylidene-1H-pyrimidin-4-one
• CAS: 1672-48-6
• 化学式: C₄H₄N₄O₂S
• mdl: MFCD01104100
• 分子量: 172.167
• InChiKey: UOWCFGBLAMCSFY-UHFFFAOYSA-N

物化性质

• 熔点：
  >240 °C
• 密度：
  1.597 (estimate)
• 溶解度：
  0.1NNaOH（轻微超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2933599090

SDS

Name:	6-Amino-5-nitroso-2-thiouracil 99% Material Safety Data Sheet
Synonym:	4-Amino-6-hydroxy-2-mercapto-5-nitrosopyrimidin
CAS:	1672-48-6

Section 1 - Chemical Product MSDS Name:6-Amino-5-nitroso-2-thiouracil 99% Material Safety Data Sheet
Synonym:4-Amino-6-hydroxy-2-mercapto-5-nitrosopyrimidin

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1672-48-6	6-Amino-5-nitroso-2-thiouracil	99	216-807-8

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Dust may cause mechanical 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 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:
Antidote: None reported.

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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. 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:
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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1672-48-6: 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:
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: Powder
Color: orange
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: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C4H4N4O2S
Molecular Weight: 172.16

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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:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1672-48-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
6-Amino-5-nitroso-2-thiouracil - 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: Not available.
Risk Phrases:
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# 1672-48-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1672-48-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1672-48-6 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：

  6-氨基-5-亚硝基-2-硫脲嘧啶 在 氨 作用下， 生成 4-Amino-6-hydroxy-5-nitroso-1H-pyrimidine-2-thione; compound with ammonia
  参考文献：
  名称：

  Rh(III), Pd(II), Pt(IV) and Au(III) complexes of 2-thiopyrimidine derivatives

  摘要：

  DOI：

  10.1007/bf00815316
• 作为产物：
  描述：

  6-氨基-2-硫脲嘧啶 在 溶剂黄146 、 sodium hydroxide 、 sodium nitrite 作用下， 生成 6-氨基-5-亚硝基-2-硫脲嘧啶
  参考文献：
  名称：

  Synthesis, Experimental and Computational Studies of N-(4-amino-6-oxo- 1,6-dihydropyrimidin-5-yl)benzamide

  摘要：

  背景：阻断 kainate 受体是治疗神经退行性疾病（包括帕金森病）和癫痫的一种新兴策略。尤其是非竞争性的凯恩酸盐受体拮抗剂，因其良好的安全性而大有可为。我们在此介绍 N-(4-氨基-6-氧代-1,6-二氢嘧啶-5-基)苯甲酰胺的合成、实验和计算研究。 方法：结果：对标题化合物进行的详细 X 射线研究证实了反应过程。标题化合物在三棱 P-1 空间群中结晶。不对称单元包括两个独立的化合物分子（A 和 B）和一个 DMF 溶剂分子。势能分布（PED）分析有助于解释红外光谱。结论：标题化合物是一种表征良好的中间体，它将被环化成次黄嘌呤衍生物，被设计为凯恩酸盐 GluK1 和 GluK2 受体的非竞争性拮抗剂。

  DOI：

  10.2174/1570178614666170811123851

文献信息

• New N⁶-substituted 8-alkyl-2-phenylmethylsulfanyl-adenines. II
  作者：Giuliana Biagi、Irene Giorgi、Oreste Livi、Federica Pacchini、Valerio Scartoni、Oreste Leroy Salerni

  DOI：10.1002/jhet.5570410416

  日期：2004.7

  reaction using the diazonium salt derived from p-methylaniline afforded the azo derivative 7, which was subsequently alkylated and reductively cleaved to form compounds 8 and 11 respectively (See Scheme). Compound 11 was annulated to the corresponding hypoxanthine derivatives 12–14; compounds 12 and 13 were chlorinated with phosphorus oxychloride, then reacted with amines to yield compound 17 and 20 respectively

  由新合成的嘧啶衍生物11制备在C（2），C（6）和C（8）上带有取代基的标题化合物。通过两种不同的合成方案由化合物2产生新的嘧啶11。在一个途径中，化合物2是亚硝化，还原并烷基化，以产生玉米磅9，10和11分别（方案）。在使用化合物2作为起始原料的另一种方法中，使用衍生自对甲基苯胺的重氮盐进行偶合反应，得到了偶氮衍生物7，随后将其烷基化并还原裂解形成化合物。分别为8和11（请参阅方案）。将化合物11环化为相应的次黄嘌呤衍生物12-14；用三氯氧化磷氯化化合物12和13，然后与胺反应分别得到化合物17和20。化合物21，22和23分别由相应的硫化物的氧化，如方案描绘得到的。硫醇官能团1的烷基化得到3和4的混合物。将化合物3氯漂洗至5。硝化5会导致芳基环发生亲电取代，硫化物同时氧化为亚砜，生成6。
• Synthesis and Antioxidant Activity of a Novel Series of Pyrazolotriazine, Coumarin, Oxoazinone, and Pyrazinopyrimidine Derivatives
  作者：Moustafa A. Gouda

  DOI：10.1002/ardp.201300128

  日期：2013.8

  afforded the corresponding coumarins 21–23, respectively. Finally, compound 1 reacted with 1‐nitrosonaphthalen‐2‐ol (26) and 6‐amino‐5‐nitroso‐2‐thioxo‐2,3‐dihydropyrimidin‐4(1H)‐one (28) to give 3‐oxo‐3H‐naphtho[2,1‐b][1,4]oxazine‐2‐carbonitrile (25) and pyridazinopyrimidine (29), respectively. The newly synthesized compounds were screened for their ABTS antioxidant activity. Compounds 7 (90.39%), 10

  通过将 3-(3,5-二甲基-1H-吡唑-1-基)-3-氧代丙腈 (1) 与 3-吡唑重氮氯化物 2-4 偶联，然后加热，获得一系列吡唑并三酮衍生物 8-10分别在乙酸中形成的腙5-7。此外，1与芳基重氮盐15a-c的偶联反应得到腙16a-c。此外，用 2-羟基-1-醛 18-20 处理 1 分别得到相应的香豆素 21-23。最后，化合物 1 与 1-nitrosonaphthalen-2-ol (26) 和 6-amino-5-nitroso-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (28) 反应得到 3-oxo- 3H-萘并[2,1-b][1,4]恶嗪-2-甲腈（25）和哒嗪并嘧啶（29）。筛选新合成的化合物的 ABTS 抗氧化活性。化合物 7 (90.39%)、10 (85.88%) 和 16a (91. 95%) 表现出有希望的活动。最有效的化合物
• Synthesis and Stereochemistry of Homoleptic Cobalt(III) Complexes Containing Pyrimidine-2-thionate and Its Derivatives
  作者：Kazuaki Yamanari、Shozo Dogi、Kensen Okusako、Takashi Fujihara、Akira Fuyuhiro、Sumio Kaizaki

  DOI：10.1246/bcsj.67.3004

  日期：1994.11

  Co(CH3CO2)2·4H2O with pyrimidine-2-thione (Hpymt), or eight kinds of their derivatives (mole ratio = 1 : 2.8—3.0) in methanol, was carried out in air. It was found that the substituent group at a 4-position in the pymt skeleton governs the product. The pymt and its derivatives, having an alkyl or an amino group as the 4-substituent, gave tris-type cobalt(III) complexes mer-[Co(N-S)3] in good yields. On the other hand

  Co(CH3CO2)2·4H2O 与嘧啶-2-硫酮 (Hpymt) 或其八种衍生物（摩尔比 = 1:2.8-3.0）在甲醇中的室温反应在空气中进行。发现 pymt 骨架中 4 位的取代基控制着产物。具有烷基或氨基作为 4-取代基的 pymt 及其衍生物以良好的产率得到三型钴 (III) 配合物 mer-[Co(NS)3]。另一方面，具有氧或硫原子作为 4-取代基的 2-硫尿嘧啶衍生物仅产生双型钴 (II) 配合物 [Co(NS)2]。这种不同的配体行为涉及嘧啶环的不同电子结构。mer-[Co(4-methyl-pymt)3] 中存在三种连接异构体，已通过 59Co NMR 光谱证实，
• Synthesis, Experimental and Computational Studies of N-(4-amino-6-oxo- 1,6-dihydropyrimidin-5-yl)benzamide
  作者：Agnieszka A. Kaczor、Agata Bartyzel、Monika Pitucha、Tomasz M. Wrobel、Sylwia Wozniak、Dariusz Matosiuk

  DOI：10.2174/1570178614666170811123851

  日期：2018.5.9

  Background: Blockade of kainate receptors is an emerging strategy to treat neurodegenerative diseases, including Parkinson's disease as well as to treat epilepsy. In particular, non-competitive antagonists of kainate receptors are promising due to the expected good safety profile. We present here synthesis, experimental and computational studies of N-(4-amino-6-oxo-1,6-dihydropyrimidin-5- yl)benzamide which is an intermediate in the synthesis of hypoxanthine derivatives which were designed as non-competitive antagonists of kainate GluK1/GluK2 receptors. Method: The title compound was obtained in a five-step synthesis protocol and characterized used X-ray crystallography and experimental and computed spectra. Results: The presented detailed X-ray studies of the title compound confirm the reaction course. The title compound crystallizes in triclinic P-1 space group. The asymmetric unit comprises two independent molecules of the compound (A and B) and a DMF solvent molecule. The interpretation of IR spectra was facilitated by Potential Energy Distribution (PED) analysis. The low value of HOMO-LUMO gap indicates that the studied compound is relatively reactive. Conclusion: The title compound is a well-characterized intermediate which will be subjected to cyclization to hypoxanthine derivative designed as non-competitive antagonist of kainate GluK1 and GluK2 receptors.

  背景：阻断 kainate 受体是治疗神经退行性疾病（包括帕金森病）和癫痫的一种新兴策略。尤其是非竞争性的凯恩酸盐受体拮抗剂，因其良好的安全性而大有可为。我们在此介绍 N-(4-氨基-6-氧代-1,6-二氢嘧啶-5-基)苯甲酰胺的合成、实验和计算研究。 方法：结果：对标题化合物进行的详细 X 射线研究证实了反应过程。标题化合物在三棱 P-1 空间群中结晶。不对称单元包括两个独立的化合物分子（A 和 B）和一个 DMF 溶剂分子。势能分布（PED）分析有助于解释红外光谱。结论：标题化合物是一种表征良好的中间体，它将被环化成次黄嘌呤衍生物，被设计为凯恩酸盐 GluK1 和 GluK2 受体的非竞争性拮抗剂。
• N-Alkylation of 2,6-Dichloropurine Hydrochloride with a Variety of Alcohols over Alumina Catalyst
  作者：Harikrishna Tumma、N. Nagaraju、K. Vijayakumar Reddy

  DOI：10.1080/00397910903162791

  日期：2010.5.19

  2,6-Dichloropurine hydrochloride reacts with various types of alcohols using different alumina catalysts and converts into its N-9-alkyl-2-chloro-6-hydroxy-9H-purine products to an extent of 49-74%. The product selectivity depends on the stability of carbocation generated from the alcohol. More stable carbocation formulates both N-7 and N-9-alkyl-2,6-dichloropurine products, whereas the less stable carbocation results in exclusively N-9-alkyl-2-chloro-6-hydroxy-9H-purine. The catalytic activity of alumina prepared using the sol-gel method has larger Brunauer, Emmett, and Teller (BET) surface area and hence shows significantly greater catalytic activity than the commercially available alumina samples.

表征谱图