4,5-二氨基脲嘧啶 | 3240-72-0

• 物质功能分类: 医药中间体 - 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: 4,5-二氨基脲嘧啶
• 中文别名: 5,6-氨基-2,4(1H,3H)-嘧啶二酮；5,6-二氨基尿嘧啶；5,6-二氨基-2,4-二羟基嘧啶
• 英文名称: 5,6-diaminouracil
• 英文别名: 5,6-diaminopyrimidine-2,4(1H,3H)-dione；5,6-diaminopyrimidine-2,4-diol
• CAS: 3240-72-0
• 化学式: C₄H₆N₄O₂
• mdl: MFCD00023155
• 分子量: 142.117
• InChiKey: BBTNLADSUVOPPN-UHFFFAOYSA-N

物化性质

• 熔点：
  >250°C
• 密度：
  1.481±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（少许）、水（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  10
• 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：
  110
• 氢给体数：
  4
• 氢受体数：
  4

安全信息

• 海关编码：
  2933599090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  -20°C freezer

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 5,6-DIAMINOURACIL
CAS-No. : 3240-72-0
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Acute toxicity, Oral (Category 4)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
Precautionary statement(s) none
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R22 Harmful if swallowed.
S-phrase(s) none
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C4H6N4O2
Molecular Weight : 142,12 g/mol
Component Concentration
5,6-DIAMINOURACIL
CAS-No. 3240-72-0 -

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been thoroughly
investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIRE-FIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at
the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested and
approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the
standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use
respirators and components tested and approved under appropriate government standards such as
NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- log Pow: -1,689
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation
May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been thoroughly
investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途：作为嘌呤类生物碱，如咖啡因、茶碱和可可碱的中间体。

生产方法：可通过4-氨基-5-亚硝基脲嘧啶在贵金属催化剂的作用下进行氢化反应来制备。

反应信息

• 作为反应物：
  描述：

  4,5-二氨基脲嘧啶 在 吡啶 、 N-亚磺酰苯胺 作用下， 生成 [1,2,5]噻二唑并[3,4-d]嘧啶-5,7(4H,6H)-二酮
  参考文献：
  名称：

  Thiadiazoles. I. Synthesis and Properties of [1,2,5]Thiadiazolo[3,4-d]pyrimidines¹

  摘要：

  DOI：

  10.1021/jo01053a061
• 作为产物：
  描述：

  4-氨基-2,6-二羟基-5-亚硝基嘧啶 在 sodium dithionite 作用下， 生成 4,5-二氨基脲嘧啶
  参考文献：
  名称：

  Novel Riboflavin-Inspired Conjugated Bio-Organic Semiconductors

  摘要：

  黄素被认为是非常多功能的，因此可以通过多种修改途径来获得所需的性质。因此，在本文中，基于阿洛克赛因核心的生物启发共轭材料群体使用两种高效的新型合成方法合成，提供了相对较高的反应产率。对材料的全面表征，以评估其性质和应用潜力，表明将初始的阿洛克赛因核心与芳香族取代基进行改性可以微调光学带隙、电子轨道位置、吸收和发射性质。有趣的是，这些化合物具有多色色团行为，这被认为是分子内质子转移的结果。

  DOI：

  10.3390/molecules23092271

文献信息

• A Simple Synthesis of New Pyrimidinyl Purine Diones
  作者：V. S. Yadava、Neeraj Singh、S. S. Yadav、Vijay S. Yadav、Tej Bahadur

  DOI：10.1515/hc.2010.16.1.35

  日期：2010.1

  One-pot facile synthesis of three novel unusual pyrimidinyl purine diones viz. 8-[I-(4-Amino-2-oxo-l,2dihydropyrimidin-1 -yl)-ethyl]-3-methyl-3,7-dihydro-1 //-purine-2,6-dione 3a, 8-[ 1 -(4-Amino-2-oxo-1,2dihydropyrimidin-l-yl)-ethyl]-1,3-dimethy 1-3,7-dihydro-1 //-purine-2,6-dione 3b, and 8-[ 1 -(4-amino-2-oxo-1,2dihydropyrimidin-l-yl)ethyl]-3,7-dihydro-l//-purine-2,6-dione 3c using BF3.Et2O have

  三种新型不寻常嘧啶基嘌呤二酮的一锅法简便合成，即。8-[I-(4-Amino-2-oxo-1,2dihydropyrimidin-1-yl)-ethyl]-3-methyl-3,7-dihydro-1 //-purine-2,6-dione 3a, 8 -[ 1 -(4-Amino-2-oxo-1,2dihydropyrimidin-1-yl)-ethyl]-1,3-dimethy 1-3,7-dihydro-1 //-purine-2,6-dione 3b和 8-[ 1 -(4-氨基-2-氧代-1,2-二氢嘧啶-1-基)乙基]-3,7-二氢-1//-嘌呤-2,6-二酮 3c 使用 BF3.Et2O 具有被举报。
• Synthesis of bis(trifluoromethylated) pyrazine-containing nitrogen heterocycles from hexafluorobiacetyl and ortho-diamines. Stabilization of the covalent dihydrates of pteridines and pyrido[3,4-b]pyrazines by trifluoromethyl groups
  作者：Mark Cushman、Wai Cheong Wong、Adelbert Bacher

  DOI：10.1039/p19860001043

  日期：——

  extent to which trifluoromethyl groups stabilize covalently bound hydrates. The substituted quinoxalines as well as the pyrido[2,3-b]pyrazine (25) and the lumazines (27), (29), and (31) were all found to exist as completely dehydrated aromatic species. Depending on the reaction conditions, both the aromatic form (33) and the stable, neutral covalent dihydrate form (34) could be obtained from the reaction

  为了确定三氟甲基基团稳定共价结合的水合物的程度，已经对源自全氟丁烷-2，3-二酮（PFBD）和多种邻二胺的反应产物的结构进行了研究。发现取代的喹喔啉以及吡啶并[2,3- b ]吡嗪（25）和lumazines（27），（29）和（31）均以完全脱水的芳族物质形式存在。取决于反应条件，芳族形式（33）和稳定的中性二价二水合物形式（34））可通过PFBD与4,5-二氨基-6-羟基嘧啶硫酸盐的反应制得（32）。还发现吡啶并[3，4- b ]吡嗪系统（36）和蝶啶（38）以稳定的中性共价二水合物存在，其中吡嗪环被选择性地水合。
• Synthesis and Biological Evaluation of New Dipyridylpteridines, Lumazines, and Related Analogues
  作者：Zina A. A. Abbas、Najwa M. J. Abu-Mejdad、Zeenah W. Atwan、Najim A. Al-Masoudi

  DOI：10.1002/jhet.2651

  日期：2017.3

  methanolic ammonia under drastic conditions. Condensation of 2 or 29 with 2‐oxo‐2‐(thiophen‐2‐yl)acetaldehyde oxime (11) gave the 6‐(2‐thienyl)‐pteridine‐4‐one (12) and 5‐chloro‐2‐(2‐thienyl)pyrido[3,4‐b]pyrazine (31), respectively. All compounds were evaluated for their antiviral activity against the replication of HIV‐1 and HIV‐2 in MT‐4. Some of the synthesized compounds were tested against the bacterial

  4,5-二氨基嘧啶2和3与2,2ʹ-联吡啶（4）的缩合分别得到6,7-双（2-吡啶基）蝶啶-2-一类似物5和7。类似地，6,7-双（2-吡啶基）luamzine衍生物13，15，17，和23，从5,6-二氨基-2- thiopyrimidines反应合成13，14，和22与4，分别，而缩合4,5,6-三氨基嘧啶（25）或5,6-二氨基类似物26与4分别提供了4-氨基蝶啶类似物27和28。得到4-硫代类似物的新蝶啶和lumazines的硫杂化6，8，16，和24。用甲醇氨水处理6和8分别得到4-异is呤类似物9和10。用取代的苯甲酰氯将15烷基化，得到18和19，它们环化为噻唑并蝶啶衍生物20和21分别用多磷酸处理。或者，在剧烈条件下，用甲醇氨处理24，制得27。2或29与2-氧代-2-（噻吩-2-基）乙醛肟（11）的缩合得到6-（2-噻吩基）-哌啶-4-基（12）和5-氯-2-（- 2-噻吩基]吡啶并[3
• Synthesis and antiviral evaluation of several 6-(Methylene-carbomethoxy)pteridine-4,7(3<i>H</i>,8<i>H</i>)-diones
  作者：S. Molina、J. Cobo、A. Sánchez、M. Nogueras、E. De Clercq

  DOI：10.1002/jhet.5570360216

  日期：1999.3

  in this paper. 6-Amino-5-(E)(1′,2′-dicarbomethoxyvinyl)aminopyrimidines, 2, and 6-(methylenecarbomethoxy)pteridinones, 3, have been obtained as main the products, which can be explained on the basis of a Michael addition on pyrimidine derivatives, and cyclization. Those compounds were evaluated for their in vitro antiviral activity.

  本文讨论了5,6-二氨基嘧啶-4（3 H）-one衍生物1a-h与乙炔二羧酸二甲酯的反应。已经获得了6-氨基-5-（E）（1'，2'-二甲氧基甲氧基乙烯基）氨基嘧啶2和6-（亚甲基羰基甲氧基）蝶啶酮3作为主要产物，这可以根据迈克尔（Michael）的解释进行。加成嘧啶衍生物，并环化。评估这些化合物的体外抗病毒活性。
• Facile preparation of 9-H-pyrimido [4,5-b] [1,4] diazepine derivatives from 4,5-diaminopyrimidines and ethyl pyruvate.
  作者：Manuel Melguizo、Adolfo Sánchez、Manuel Nogueras、John N. Low、R. Alan Howie、Graciela Andrei、Erik De Clercq

  DOI：10.1016/s0040-4020(01)89358-3

  日期：1994.1

  A facile novel procedure to obtain (±)-6,8-diethoxycarbonyl-6-methyl-9-H-pyrimido [4,5-b] [1,4] diazepines from 4,5-diaminopyrimidines and ethyl pyruvate is described. The structure of pyrimido [4,5-b] [1,4] diazepine derivatives for the products of this reaction was confirmed by single crystal X-ray diffraction analysis. The procedure proved to be of wide scope with reference to the substituent of

  描述了一种从4,5-二氨基嘧啶和丙酮酸乙酯获得（±）-6,8-二乙氧基羰基-6-甲基-9- H-嘧啶[4,5- b ] [1,4]二氮杂pine的简便新方法。通过单晶X射线衍射分析确认了该反应产物的嘧啶基[4，5- b ] [1，4]二氮杂苯衍生物的结构。相对于起始嘧啶的取代基，该方法被证明具有广泛的应用范围。介绍了使用几种新合成的化合物作为抗癌剂和抗病毒剂进行的生物学测试结果。