5,6-二氨基-1,3-二甲基脲嘧啶 - CAS号 5440-00-6

物化性质

熔点：

210-214 °C (dec.)(lit.)
沸点：

243.6±50.0℃ (760 Torr)
密度：

1.350±0.06 g/cm3 (20 ºC 760 Torr)
闪点：

101.1±30.1℃
溶解度：

可溶于二甲基亚砜、甲醇
稳定性/保质期：

如果按照规定使用和储存，则不会分解，未曾发生过已知的危险。应避免与强氧化剂接触。

计算性质

辛醇/水分配系数(LogP)：

-0.5
重原子数：

12
可旋转键数：

0
环数：

1.0
sp3杂化的碳原子比例：

0.333
拓扑面积：

92.7
氢给体数：

2
氢受体数：

4

安全信息

WGK Germany：

3
海关编码：

2933599090
危险性防范说明：

P261,P305+P351+P338
危险性描述：

H302,H315,H319,H335
储存条件：

应将药品存放在密闭、阴凉干燥处，并保持良好通风。同时，容器内应充入惰性气体以保证安全。

SDS

SDS：6041fc21a0a56b96a608b68e0726df44

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 5,6-Diamino-1,3-dimethyluracil hydrate
CAS-No. : 5440-00-6

Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No 1272/2008
Not a hazardous substance or mixture according to EC-directives 67/548/EEC or 1999/45/EC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : 5,6-Diamino-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione
Formula : C6H10N4O2 · xH2O
Molecular Weight : 170,17 g/mol

Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
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.
Most important symptoms and effects, both acute and delayed
Indication of any immediate medical attention and special treatment needed
no data available

Section 5. FIREFIGHTING 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

Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Store under inert gas.
Specific end uses
no data available

Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
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
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).

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 Melting point/range: 210 - 214 °C - dec.
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- no data available
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

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

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 May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Additional Information
RTECS: Not available

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

Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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

Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途：医药中间体。

生产方法：通过氰乙酸经过缩合、环合、亚硝化和还原步骤制得。

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
1,3-二甲基-6-亚氨基-5-异亚硝基尿嘧啶	6-amino-1,3-dimethyl-5-nitroso-1H-pyrimidine-2,4-dione	6632-68-4	C₆H₈N₄O₃	184.155
6-氨基-5-甲酰氨基-1,3-二甲基尿嘧啶	1,3-dimethyl-4-amino-5-(formylamino)uracil	7597-60-6	C₇H₁₀N₄O₃	198.181
6-氨基-1,3-二甲基-5-亚硝基尿嘧啶	6-amino-1,3-dimethyl-5-nitro-1H-pyrimidine-2,4-dione	3346-61-0	C₆H₈N₄O₄	200.154
——	5-acetylamino-6-amino-1,3-dimethyl-1H-pyrimidine-2,4-dione	10184-41-5	C₈H₁₂N₄O₃	212.208
1,3-二甲基-6-氨基脲嘧啶	6-Amino-1,3-dimethylbarbituric acid	6642-31-5	C₆H₉N₃O₂	155.156
——	1,3-dimethyl-5-nitro-6-hydrazinouracil	906428-70-4	C₆H₉N₅O₄	215.169
——	5-acetylamino-6-amino-1-methyl-1H-pyrimidine-2,4-dione	10184-42-6	C₇H₁₀N₄O₃	198.181

下游产品

中文名称	英文名称	CAS号	化学式	分子量
6-氨基-5-甲酰氨基-1,3-二甲基尿嘧啶	1,3-dimethyl-4-amino-5-(formylamino)uracil	7597-60-6	C₇H₁₀N₄O₃	198.181
——	N-(6-amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-glycine-nitrile	7468-65-7	C₈H₁₁N₅O₂	209.208
——	5-acetylamino-6-amino-1,3-dimethyl-1H-pyrimidine-2,4-dione	10184-41-5	C₈H₁₂N₄O₃	212.208
——	6-amino-5-(benzylideneamino)-1,3-dimethyluracil	60228-89-9	C₁₃H₁₄N₄O₂	258.28
——	6-amino-5-(benzylideneamino)-1,3-dimethylpyrimidine-2,4-dione	60228-89-9	C₁₃H₁₄N₄O₂	258.28
——	6-amino-1,3-dimethyl-5-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-1H-pyrimidine-2,4-dione	1198748-32-1	C₁₅H₁₆N₄O₂	284.318
——	N-(6-amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-2-hydroxyacetamide	6743-05-1	C₈H₁₂N₄O₄	228.208
——	6-amino-5-(4-chloro-benzylideneamino)-1,3-dimethyl-1H-pyrimidine-2,4-dione	13784-07-1	C₁₃H₁₃ClN₄O₂	292.725
——	6-amino-5-[(4-chlorophenyl)methylideneamino]-1,3-dimethylpyrimidine-2,4-dione	13784-07-1	C₁₃H₁₃ClN₄O₂	292.725
——	6-amino-5-{[1-(3-chlorophenyl)-meth-(E)-ylidene]-amino}-1,3-dimethyl-1H-pyrimidine-2,4-dione	1198748-31-0	C₁₃H₁₃ClN₄O₂	292.725

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反应信息

作为反应物：

描述：

5,6-二氨基-1,3-二甲基脲嘧啶在三光气、 1,8-二氮杂双环[5.4.0]十一碳-7-烯、三乙胺作用下，以 N-甲基吡咯烷酮为溶剂，生成四甲尿酸

参考文献：

名称：

一种1,3,7,9-四甲基尿酸的全合成方法

摘要：

本发明涉及一种1,3,7,9‑四甲基尿酸的全合成方法，包括以6‑氨基‑1,3‑二甲基尿嘧啶为原料，经过亚硝基化反应得到中间体6‑氨基‑1,3‑二甲基‑5‑亚硝基尿嘧啶；6‑氨基‑1,3‑二甲基‑5‑亚硝基尿嘧啶经还原反应得到中间体1,3‑二甲基‑5，6‑二氨基尿嘧啶；1,3‑二甲基‑5，6‑二氨基尿嘧啶进行环合反应生成中间体1,3‑二甲基尿酸；1,3‑二甲基尿酸和甲基化试剂进行反应得到产物。采用本发明方法来制备四甲基尿酸，可在工业应用上大量合成，不受原料对其的约束；转化率高，产率高，合成方便，后处理较简单，适合大规模生产，能够广泛的推广应用；无须在高压条件下进行，对设备要求低，同时减少了危险的发生率；利用重结晶放置制备目标产物，产物纯度高。

公开号：

CN106046004B
作为产物：

描述：

6-氨基-5-甲酰氨基-1,3-二甲基尿嘧啶在盐酸、甲醇作用下，生成 5,6-二氨基-1,3-二甲基脲嘧啶

参考文献：

名称：

Bredereck; Edenhofer, Chemische Berichte, 1955, vol. 88, p. 1306,1309

摘要：

DOI：
作为试剂：

描述：

1,10-邻二氮杂菲-5,6-二酮在 5,6-二氨基-1,3-二甲基脲嘧啶、溶剂黄146 作用下，以乙醇为溶剂，以21%的产率得到1,10-phenanthroline-5,6-diol hydrochloride

参考文献：

名称：

5,6-Dihydroxy-1,10-phenanthrolinium-1,10-ium dichloride

摘要：

5,6- 二羟基-1,10-菲罗啉是 1,10-菲罗啉-5,6-二酮和 5,6- 二氨基-1,3-二甲基脲嘧啶缩合反应的副产物，通过乙腈蒸发扩散到乙醇/HCl 溶液中分离出二盐酸盐 (C12H8N2O2-2HCl-0.5CH3CN)。该化合物在三linic 空间群 $$ P\overline{1} $$ 中结晶，a = 5.8334(1) 埃，b = 9.8041(2) 埃，c = 11.9895(2) 埃，α = 81.511(1)°，β = 76.395(1)°，γ = 81.429(1)°，V = 654.48(2) Å3，Z = 2，R[F 2 > 2σ(F 2)] = 0.028，wR(F 2) = 0.078。两种 N-H+-Cl- 相互作用（2.18(3) 埃、2.13(2) 埃）和两种 O-H-Cl- 相互作用（2.11(3) 埃、2.20(3) 埃）稳定了晶体堆积。菲罗啉环的π-堆积导致平面间距为 3.431(5) 埃，菲罗啉环的中心点彼此相距约 6 埃。该双质子化物种的结果与 Lin 等人（Acta Cryst E65:o2367, 2009）报告的单质子化形式的结果进行了比较，从而揭示了使用 -OH/ 菲罗啉环的相对取向作为该配体的金属配合物中金属-配体相互作用的定性诊断的可能性（Larsson 和 Ohrstrom，发表于 Inorg Chim Acta 357:657, 2004；Guan 等人，发表于 Acta Cryst C64:m311, 2008）。本文讨论了 5,6-二羟基-1,10-菲罗啉的二质子化形式（5,6-二羟基-1,10-菲罗啉鎓-1,10-二氯化物）的晶体结构，并将其与文献中报道的单质子化形式以及与锰（II）和钴（III）络合的形式进行了比较。

DOI：

10.1007/s10870-011-0003-0

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文献信息

Synthesis and Regioselective N- and O-Alkylation of 1H- or 3H-[1,2,3]Triazolo[4,5-d]pyrimidine-5,7(4H,6H)-diones (8-Azaxanthines) and Transformation of Their 3-Alkyl Derivatives into 1-Alkyl Isomers

作者：Tomohisa Nagamatsu、Rafiqul Islam

DOI：10.1055/s-2006-950337

日期：——

alkylating agents, for example alkyl halides and dimethyl sulfate, were employed in aprotic Solvents Under a variety of conditions for the alkylation of mono- and disubstituted 1H- or 3H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-diones, which were prepared by cyclization of the appropriate 5,6-diaminouracils with nitrous acid. The alkylation on the triazole ring in the presence of anhydrous potassium carbonate

在非质子溶剂中使用了几种烷基化剂，例如卤代烷和硫酸二甲酯在各种条件下用于单取代和双取代的 1H-或 3H-[1,2,3]三唑并[4,5-d]的烷基化嘧啶-5,7(4H,6H)-二酮，通过适当的 5,6-二氨基尿嘧啶与亚硝酸的环化制备。在无水碳酸钾存在下，三唑环上的烷基化同时在 1 位和 2 位发生，优先在 2 位烷基化。用等价的烷基化试剂在嘧啶环上进行类似的烷基化仅在 4 位发生。3,6-二取代衍生物在室温下烷基化导致5-O-烷基化伴随4-N-烷基化，但在高温下仅发生4-N-烷基化。3,4的反应，
Adenosine A1 antagonists. 2. Structure-activity relationships on diuretic activities and protective effects against acute renal failure

作者：Fumio Suzuki、Junichi Shimada、Hideaki Mizumoto、Akira Karasawa、Kazuhiro Kubo、Hiromi Nonaka、Akio Ishii、Takashi Kawakita

DOI：10.1021/jm00094a022

日期：1992.8

Diuretic activities of xanthine or nonxanthine adenosine antagonists and their ameliorative effects against glycerol-induced acute renal failure in rats were investigated in order to clarify the physiological and pathological function of adenosine receptors in the kidney. Diuretic and natriuretic activities of a variety of adenosine antagonists clarified systematically for the first time that the blockade

为了阐明肾脏中腺苷受体的生理和病理功能，研究了黄嘌呤或非黄嘌呤腺苷拮抗剂的利尿作用及其对甘油诱导的急性肾衰竭的缓解作用。各种腺苷拮抗剂的利尿和利尿作用首次系统性地阐明，在钠和水的排泄中，A1受体的阻滞比A2受体的阻滞更重要，并支持内源性肾内腺苷水平直接增强肾小管钠吸收的假说。。急性肾衰竭中8取代的黄嘌呤的构效关系研究表明，腺苷A1受体的激活是发展这种肾衰竭的重要因素。一系列8-（3-去甲金刚烷基）黄嘌呤表现出极强的利尿和利尿活性（24; 2.5微克/千克，po，治疗大鼠尿排泄值与对照大鼠尿排泄值之比= 1.69，该比率（治疗大鼠的Na + / K +相对于对照组大鼠的Na + / K + ＝ 1.76）和抗甘油诱导的急性肾衰竭的有效改善作用（24; 10微克/ kg，腹腔注射，抑制55％）。通过对结构-活性关系的详细研究，我们可以推测，肾脏和大脑之间可能存在腺苷A1受体的一些组织差异，并
Immunosuppressive effects of 8-substituted xanthine derivatives

申请人：K.U. Leuven Research & Development

公开号：US07253176B1

公开（公告）日：2007-08-07

The invention relates to a novel use of 8-substituted xanthine derivatives for the manufacture of a medicament for the treatment of auto-immuno disorders.

这项发明涉及使用8-取代黄嘌呤衍生物制造治疗自身免疫性疾病药物的新方法。
Immunosuppressive effects of pteridine derivatives

申请人：——

公开号：US20030236255A1

公开（公告）日：2003-12-25

Novel poly-substituted pteridinediones (lumazines), and mono- or polysubstituted 2-thiolumazines, 4-thiolumazines or 2,4-dithiolumazines, having disclosed substituents in positions 1, 3, 6 and 7 of the pteridine ring, and pharmaceutically acceptable salts thereof, are useful as biologically active ingredients in preparing pharmaceutical compositions especially for the treatment or prevention of a CNS disorder, a cell proliferative disorder, a viral infection, an immune or auto-immune disorder or a transplant rejection. Combinations of the pteridine derivatives of the invention with an immunosuppressant or immunomodulator drug, an antineoplastic drug or an antiviral agent, providing potential synergistic effects, are also disclosed.

新型多取代的喹啉二酮（卢马嗪），以及单取代或多取代的2-硫代卢马嗪，4-硫代卢马嗪或2,4-二硫代卢马嗪，在喹啉环的1、3、6和7位上具有已披露的取代基，并且其药学上可接受的盐，在制备药物组合物中作为生物活性成分特别用于治疗或预防中枢神经系统疾病、细胞增殖障碍、病毒感染、免疫或自身免疫障碍或移植排斥。本发明的喹啉衍生物与免疫抑制剂或免疫调节剂药物、抗肿瘤药物或抗病毒药物的组合，提供潜在的协同效应。
Synthesis of Deuterium Labeled Standards of 1-Benzylpiperazine, Fenetylline, Nicocodeine and Nicomorphine

作者：Zong-Yi You、Yi-Jing Chen、Yu-Yun Wang、Chinpiao Chen

DOI：10.1002/jccs.200800099

日期：2008.6

analogs (designer drugs) with a large variety of structures have reached illegal markets, making their identification difficult. This work studies the synthesis of BZP-d 7 , fenetylline-d 4 , nicocodeine-d 4 and nicomorphine-d 8 , as internal standards for use in gas chromatography-mass spectrometry (GC-MS) analysis for identification of these controlled substances.

越来越多地滥用的 1-苄基哌嗪 (BZP)、苯乙茶碱、尼可待因和尼可吗啡是具有神经毒性的中枢神经系统兴奋剂。近年来，许多具有多种结构的受控物质类似物（设计药物）进入非法市场，使其识别变得困难。这项工作研究了 BZP-d 7 、苯乙胺-d 4 、尼可待因-d 4 和尼可吗啡-d 8 的合成，作为用于鉴定这些受控物质的气相色谱-质谱 (GC-MS) 分析的内标。

表征谱图

氢谱

1HNMR
质谱

MS
碳谱

13CNMR
红外

IR
拉曼

Raman

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峰位数据
峰位匹配
表征信息

Shift(ppm)

Intensity

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Assign

Shift(ppm)

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测试频率

样品用量

溶剂

溶剂用量

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5,6-二氨基-1,3-二甲基脲嘧啶 | 5440-00-6

物质功能分类

分子结构分类

物化性质

计算性质

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