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简介胞嘧啶(Cytosine),为白色结晶性粉末,微溶于水和乙醇,不溶于乙醚,熔点300℃,100℃时失去结晶水,300℃时成棕色,320℃;化学名称:4-氨基-2-羟基嘧啶,是生物体中参与DNA、RNA合成的重要活性原料,为构成核酸的嘧啶碱基之一。
应用胞嘧啶是精细化工、农药和医药的重要中间体,具有广泛应用。在农药上,首次发现的胞嘧啶核苷肽型新抗生素,它是一种高效、低毒、低残留的广谱性农用抗生素。在医药领域,胞嘧啶是一种核酸类物质,可做一种抗病毒药物,主要用于合成抗艾滋病药物及抗乙肝药物拉米夫定,抗癌药物吉西他宾、以及5-氟胞嘧啶等。
用途用作药物中间体
REFERENCE
制备中间体1具体合成方法为:在2500毫升的圆底烧瓶中,加入尿素180克(3.0摩尔),原甲酸三乙酯370克(2.5摩尔),氰乙酸乙酯226克(2.0摩尔),搅拌回流4小时,不断观察回流现象,确保回流均匀稳定。停止反应后,冷却抽滤,收集黄白色固体,并用丙酮淋洗,烘干,得中间体1,黄白色粉末状固体294.5克,收率为81%。 中间体2具体合成方法为:向2500毫升的圆底烧瓶中,加入无水甲醇1000毫升,分批加入23克(1摩尔)金属钠,待金属钠完全溶解后加入183(1摩尔)克中间体1,加入5.6克纳米氧化钙粉体(0.1摩尔),加热至60℃回流3小时,停止反应,冷却,抽滤收集黄色固体。将所得固体溶于500毫升水中,边搅拌边加水,直至黄色固体全部溶解。用稀盐酸(由浓盐酸与水的体积比为1:3配制而来)酸化至pH=6~7之间,有沉淀生成,抽滤收集白色固体,并用少量丙酮洗涤。烘干,得中间体2,白色粉末状固体,53克,收率29%。 中间体3具体合成方法为:配制质量分数为10%的NaOH溶液800毫升,加入到2500毫升的圆底烧瓶中,加热至90摄氏度,加入中间体91.5(0.5摩尔)搅拌15分钟。迅速冷却至室温,而后加入盐酸酸化pH=5,有白色沉淀生成,抽滤,水洗,烘干,得5-羧基胞嘧啶,白色粉末状固体,73.6克,收率为95%。 脱羧合成胞嘧啶合成方法为:向1000毫升的圆底烧瓶中,加入77.5克(0.5摩尔)中间体3,26.8克(0.5摩尔)氯化铵,500毫升N-甲基吡咯烷酮,通入氮气保护,搅拌反应均匀后加热至180℃,并保温8小时,加热回流直到较少的气泡移除,停止反应,冷却至室温,加入乙醚150毫升,析出固体过滤,收集白色固体即为最终产物胞嘧啶,干燥,白色晶体状固体49克,收率为87.0%。
REFERENCE
化学性质白色结晶性粉末,可溶于甲醇、乙醇、DMSO等有机溶剂,来源于合成。
UPSTREAM / DOWNSTREAM
SUPPLIERS
COMPUTED
PROPERTIES
-1.73
8.0 mg/mL
>16.7 [ug/mL] (The mean of the results at pH 7.4)
> 300 °C
0.00109 [mmHg]
Monohydrate: Lustrous solid; [Merck Index] White powder; [Alfa Aesar MSDS]
Solid
Positive
2.5
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
118.8 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID4044456];117.3 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID4044456]
117.5 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)];122.8 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
121.58 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
117.4 Ų [M+H]+;122.6 Ų [M+H]+
GHS
This chemical does not meet GHS hazard criteria for 13.6% (8 of 59) of reports.
Warning
H315 (86.4%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (86.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (84.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 59 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 8 of 59 reports by companies.;There are 8 notifications provided by 51 of 59 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
HAZARDS
Chemical: 2(1H)-Pyrimidinone, 4-amino-
Status: Active Update: 26-06-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/6166
2(1H)-Pyrimidinone, 4-amino-: Does not have an individual approval but may be used under an appropriate group standard
IMAP assessments - 2(1H)-Pyrimidinone, 4-amino-: Environment tier I assessment
Causes somnolence and changes in motor activity in intraperitoneal lethal-dose studies of mice; [RTECS] A skin and strong eye irritant; [Alfa Aesar MSDS]
Skin Irrit. 2 (86.4%);Eye Irrit. 2A (86.4%);STOT SE 3 (84.7%)
REGULATORY
Chemical: 2(1H)-Pyrimidinone, 4-amino-
Status: Active Update: 26-06-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/6166
2(1H)-Pyrimidinone, 4-amino-: Does not have an individual approval but may be used under an appropriate group standard
PHARMACOLOGY
Blood;Epidermis;Fibroblasts;Intestine;Neuron;Placenta;Prostate;Skeletal Muscle;Spleen;Testis
Extracellular
USES
Component of nucleic acids found throughout nature; [Merck Index] Used in biochemical research; [Alfa Aesar MSDS]
2(1H)-Pyrimidinone, 6-amino-: ACTIVE
ALIASES
REACTIONS
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