5-亚硝基-2,4,6-三氨基嘧啶 | 1006-23-1

• 物质功能分类: 生物化工 - 核苷类药物 - 核苷酸及其类似物
• 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: 5-亚硝基-2,4,6-三氨基嘧啶
• 中文别名: 氨苯蝶啶杂质A；2,4,6-三氨基-5-亚甲基嘧啶；5-硝基-2,4,6-三氨基嘧啶；2,4,6-三氨基-5-亚硝基嘧啶
• 英文名称: 5-nitroso-2,4,6-triaminopyrimidine
• 英文别名: 5-nitrosopyrimidine-2,4,6-triamine；2,4,6-triamino-5-nitroso-pyrimidine
• CAS: 1006-23-1
• 化学式: C₄H₆N₆O
• mdl: MFCD00006096
• 分子量: 154.131
• InChiKey: XLQQJSWJHHKLOK-UHFFFAOYSA-N

物化性质

• 熔点：
  300 °C
• 沸点：
  277.47°C (rough estimate)
• 密度：
  1.4788 (rough estimate)
• 溶解度：
  可溶于DMF（轻微加热）、DMSO（轻微加热）
• 稳定性/保质期：
  常温常压下稳定，避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 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：
  133
• 氢给体数：
  3
• 氢受体数：
  7

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S24/25
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  29335990
• 危险品运输编号：
  25kgs
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  应储存在冷干燥环境中，并放置于通风良好的地方，远离热源和不相容物质。请确保密封保存。

SDS

Name:	5-Nitroso-2 4 6-triaminopyrimidine Material Safety Data Sheet
Synonym:
CAS:	1006-23-1

Section 1 - Chemical Product MSDS Name:5-Nitroso-2 4 6-triaminopyrimidine Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1006-23-1	5-Nitroso-2,4,6-pyrimidinetriamine	100	213-742-7

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. 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 digestive tract disturbances. 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 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# 1006-23-1: 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: pink
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: > 300 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: C4H6N6O
Molecular Weight: 154.13

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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:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1006-23-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5-Nitroso-2,4,6-pyrimidinetriamine - 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# 1006-23-1: No information available.
Canada
CAS# 1006-23-1 is listed on Canada's DSL List.
CAS# 1006-23-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1006-23-1 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

应用

5-亚硝基-2,4,6-三氨基嘧啶是嘧啶类衍生物，可用作有机合成中间体。

制备

5-亚硝基-2,4,6-三氨基嘧啶可通过6-氨基嘧啶-2,4-二胺与NaNO₂反应制备得到。此外，该化合物也可由2,4,6-三氨基嘧啶经亚硝化而得。具体步骤为：将2,4,6-三氨基嘧啶和亚硝酸钠投入冰水中，在10℃以下滴加盐酸，并保持pH值在4.5至4.8之间，于20℃下反应1小时。随后进行过滤、洗涤和干燥处理，最终得到纯度较高的5-亚硝基-2,6-三氨基嘧啶，收率可达50%以上。

化学性质

该化合物为固体，熔点超过300℃。

用途

主要用作药物氨苯喋啶及氨蝶呤的中间体，并广泛应用于医药中间体领域。

反应信息

• 作为反应物：
  描述：

  5-亚硝基-2,4,6-三氨基嘧啶 在 盐酸羟胺 、 sodium acetate 作用下， 以 水 为溶剂， 以82%的产率得到2,4,5,6-tetrakis(hydroxyimino)hexahydropyrimidine
  参考文献：
  名称：

  Synthesis of 1,2,5-Oxa-, -Thia-, and -Selenadiazole N-Oxides from Nitroso- and Isonitrosopyrimidines

  摘要：

  研究了从多官能团的亚硝基和异亚硝基嘧啶及其衍生物中制备 1,2,5-氧杂、硫杂和硒杂二氮杂环 N-氧化物的可能性。

  DOI：

  10.1007/s11176-005-0249-3
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 5-乙基-2-甲基-吡啶 作用下， 生成 5-亚硝基-2,4,6-三氨基嘧啶
  参考文献：
  名称：

  Synthesis of 2-Aminonicotinamides by Raney Nickel Cleavage of Pyrazolo[3,4-b]-pyridines¹

  摘要：

  DOI：

  10.1021/ja01519a043
• 作为试剂：
  描述：

  钠 、 Triamino-nitrosopyrimidine 、 p-(2-hydroxyethoxy)-phenyl acetonitrile 在 水 、 5-亚硝基-2,4,6-三氨基嘧啶 、 crude product 、 petroleum ether 、 正丁醇 、 silica gel 作用下， 以 乙二醇乙醚 为溶剂， 反应 14.0h， 生成 2,4,7-Triamino-6-(p-2-hydroxyethoxyphenyl)-pteridine
  参考文献：
  名称：

  Substituted pteridine compounds and pharmaceutical compositions

  摘要：

  本发明涉及一种具有利尿作用的药物组合物，其活性成分为公式##STR1##中的化合物，其中R为氢、药学上可接受的阳离子、甲基或亲水基R'，还公开了R为R'的新化合物。本申请是申请号为860,824，于1977年12月15日提交的申请的续行申请，该申请现已被废弃。

  公开号：

  US04252809A1

文献信息

• Convenient and Versatile Synthetic Methods for Furazano[3,4-d]pyrimidines
  作者：Magoichi Sako、Souichi Oda、Kosaku Hirota、George P. Beardsley

  DOI：10.1055/s-1997-1349

  日期：1997.11

  Treatment of the readily available 6-amino-5-nitrosopyrimidines with a slight excess of iodobenzene diacetate or N-iodosuccinimide in anhydrous DMF containing three equivalents of lithium hydride at ambient temperature resulted in the smooth and versatile formation of the corresponding furazano[3,4-d]pyrimidines, which are useful intermediates for the preparation of biologically interesting fused pyrimidines.

  在含有三当量氢化锂的无水DMF中，以轻微过量的二乙酸碘苯或N-碘代琥珀酰亚胺处理易于获得的6-氨基-5-硝基嘧啶，并在室温下进行反应，顺利且多样地合成了相应的呋咱并[3,4-d]嘧啶，这些化合物是有趣的融合嘧啶生物活性物质的宝贵中间体。
• Imidazopyridine- and Purine-Thioacetamide Derivatives: Potent Inhibitors of Nucleotide Pyrophosphatase/Phosphodiesterase 1 (NPP1)
  作者：Lei Chang、Sang-Yong Lee、Piotr Leonczak、Jef Rozenski、Steven De Jonghe、Theodor Hanck、Christa E. Müller、Piet Herdewijn

  DOI：10.1021/jm501434y

  日期：2014.12.11

  Nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1) belongs to the family of ecto-nucleotidases, which control extracellular nucleotide, nucleoside, and (di)phosphate levels. To study the (patho)physiological roles of NPP1 potent and selective inhibitors with drug-like properties are required. Therefore, a compound library was screened for NPP1 inhibitors using a colorimetric assay with p-nitrophenyl

  核苷酸焦磷酸酶/磷酸二酯酶1（NPP1）属于胞外核苷酸酶家族，可控制细胞外核苷酸，核苷和（di）磷酸盐的水平。为了研究具有药物样特性的NPP1强效和选择性抑制剂的（病理）生理作用。因此，使用比色测定法以对硝基苯基5'-胸苷单磷酸酯（p -Nph-5'-TMP）作为人工底物，筛选化合物库中的NPP1抑制剂。这导致发现2-（3 H-咪唑并[4,5 - b ]吡啶-2-基硫基）-N-（3,4-二甲氧基苯基）乙酰胺（5a）为具有K i的命中化合物。值为217 nM。随后的结构-活性关系研究导致了嘌呤和咪唑并[4,5- b ]吡啶类似物的开发，用p -Nph-5'-进行测定具有高抑制力（K i值分别为5.00 nM和29.6 nM）。以TMP为底物。出乎意料的是，与ATP作为底物相比，测试时这些化合物的效力明显较低，K i值在低微摩尔范围内。对原型抑制剂的抑制机理进行了研究，发现该抑制剂与两种底物都具有竞争性。
• Production of purines via reductive formylation
  申请人：Skw Trostberg Aktiengesellschaft

  公开号：US05688947A1

  公开（公告）日：1997-11-18

  In order to produce a purine of the general formula (I), ##STR1## in which R.sup.1 and R.sup.2 can be the same or different and denote H, OH, SH, NH.sub.2, N-(di)-alkyl, halogen, O-alkyl, S-alkyl, alkyl or aryl and alkyl represents an aliphatic residue with 1 to 4 carbon atoms and aryl represents a phenyl residue which is substituted if desired by CH.sub.3, OH, NH.sub.2 or halogen, from the corresponding 4-amino-5-nitrosopyrimidine of formula (II), ##STR2## in which R.sup.1 and R.sup.2 have the above-mentioned meaning, the compound of formula (II) is reductively formylated in a solvent at a temperature of 80.degree. to 220.degree. C. in the presence of formic acid and a catalyst based on a noble metal and the 4-amino-5-formylaminopyrimidine formed as an intermediate is cyclized.

  为了制备一般式(I)的嘌呤，其中R.sup.1和R.sup.2可以相同也可以不同，并表示H、OH、SH、NH.sub.2、N-(二)烷基、卤素、O-烷基、S-烷基、烷基或芳基，烷基代表具有1至4个碳原子的脂肪残基，芳基代表苯基残基，如果需要可以被CH.sub.3、OH、NH.sub.2或卤素取代，从相应的4-氨基-5-亚硝基嘧啶的公式(II)中得到，其中R.sup.1和R.sup.2具有上述所述的含义，公式(II)的化合物在溶剂中在80°C至220°C的温度下，在甲酸和基于贵金属的催化剂存在下还原性甲酰化，并形成4-氨基-5-甲酰氨基嘧啶作为中间体进行环化。
• Insecticidal pterdines and 8-deazapteridines
  申请人：FMC Corporation

  公开号：US05521190A1

  公开（公告）日：1996-05-28

  This invention relates to pteridine and 8-deazapteridine compounds and compositions containing the same which are useful for controlling insects in agricultural crops. These pteridines may be represented by the following structure: ##STR1## wherein R and R.sup.1 are independently selected from amino, lower alkylamino, di(lower alkyl)amino (e.g., --N(CH.sub.3).sub.2), or di(lower alkyl)aminomethyleneamino (e.g., --N.dbd.CHN(CH.sub.3).sub.2); R.sup.2 is hydrogen, amino, lower alkyl (e.g., --CH.sub.3, --CH(CH.sub.3).sub.2), di(lower alkyl)aminomethyleneamino, hydroxy, lower alkoxy, phenyl or substituted phenyl, haloalkylphenylalkyl (e.g., 3-trifluoromethylphenylmethyl); Q is N or CH; R.sup.3 is --(n).sub.m --R.sup.4, where m is 0 or 1; wherein, when m is 1, n is a bridging atom or moiety selected from oxygen, sulfur, sulfinyl, sulfonyl, lower alkylene (e.g., --CH.sub.2 --, or --CH.sub.2 CH.sub.2 --), lower alkenylene (e.g., --CH.dbd.CH--), lower alkynylene (e.g., --C.dbd.C--), lower haloalkenylene (e.g., --C(Cl).dbd.CH--), carbonyl, aminomethyl (e.g.,--CH.sub.2 NH--), or (substituted amino)methyl (e.g.,--CH.sub.2 N(CH.sub.3)--); and R.sup.4 is hydrogen, lower alkyl (e.g., --CH.sub.3, or --CH(CH.sub.3).sub.2), thien-2-yl, pyridin-3-yl, or ##STR2## wherein (i) V, W, X, Y, and Z are as defined herein.

  这项发明涉及噻吩和8-脱氨噻吩化合物以及含有这些化合物的组合物，这些化合物在农作物中控制昆虫方面具有用途。这些噻吩可以用以下结构表示：##STR1##其中R和R.sup.1分别从氨基、较低烷基氨基、二(较低烷基)氨基（例如，--N(CH.sub.3).sub.2）或二(较低烷基)氨基甲烷基氨基（例如，--N.dbd.CHN(CH.sub.3).sub.2）中独立选择；R.sup.2为氢、氨基、较低烷基（例如，--CH.sub.3，--CH(CH.sub.3).sub.2）、二(较低烷基)氨基甲烷基氨基、羟基、较低烷氧基、苯基或取代苯基、卤代烷基苯基烷基（例如，3-三氟甲基苯基甲基）；Q为N或CH；R.sup.3为--(n).sub.m --R.sup.4，其中m为0或1；其中，当m为1时，n为氧、硫、亚砜基、磺酰基、较低烷基烯（例如，--CH.sub.2 --或--CH.sub.2 CH.sub.2 --）、较低烯烃（例如，--CH.dbd.CH--）、较低炔烃（例如，--C.dbd.C--）、较低卤代烯烃（例如，--C(Cl).dbd.CH--）、羰基、氨基甲基（例如，--CH.sub.2 NH--）或（取代氨基）甲基（例如，--CH.sub.2 N(CH.sub.3)--）中选择；而R.sup.4为氢、较低烷基（例如，--CH.sub.3或--CH(CH.sub.3).sub.2）、噻吩-2-基、吡啶-3-基，或##STR2##其中(i)V、W、X、Y和Z的定义如本文所述。
• Synthesen in der Lumiflavinreihe IV
  作者：P. Hemmerich、B. Prijs、H. Erlenmeyer

  DOI：10.1002/hlca.19590420522

  日期：——

  2,4-Substituted flavins (isoalloxazines) bearing an NH2-group in 8-position were found to be stable and easily accessible. In particular the 2- and 4-imino-, resp. 2,4-diimino-compounds are similar to riboflavin in colour and fluorescence, but readily water-soluble. The chemical behaviour of this new class of flavins is discussed.

  发现在8位上带有NH 2基团的2,4-取代的黄素（异四恶嗪）稳定且易于获得。特别是2-和4-亚氨基-。2,4-二亚氨基化合物的颜色和荧光与核黄素相似，但易溶于水。讨论了这类新黄酮的化学行为。

表征谱图