1-苯氧基-丙醇 | 770-35-4

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-苯氧基-丙醇
• 中文别名: 苯氧基丙醇；丙二醇苯醚；1-苯氧基-2-丙醇；丙二醇单苯醚；苯氧异丙醇
• 英文名称: 1-phenoxy-2-propanol
• 英文别名: 1-phenoxypropan-2-ol
• CAS: 770-35-4；41593-38-8
• 化学式: C₉H₁₂O₂
• mdl: MFCD00016861
• 分子量: 152.193
• InChiKey: IBLKWZIFZMJLFL-UHFFFAOYSA-N

物化性质

• 熔点：
  11 °C
• 沸点：
  243 °C (lit.)
• 密度：
  1.064 g/mL at 20 °C (lit.)
• 闪点：
  >230 °F
• 溶解度：
  水: 20°C时可溶15.1g/L
• LogP：
  1.41 at 24.1℃
• 物理描述：
  Liquid
• 颜色/状态：
  Colorless to yellow liquid
• 气味：
  Mild odor
• 蒸汽密度：
  5.27 (Air = 1)
• 蒸汽压力：
  0.00218 mm Hg at 25 °C
• 稳定性/保质期：

  PPh is thermally stable at typical use temperatures...PPh can decompose at elevated temperatures.

• 分解：
  Decomposition products depend upon the temperature, air supply, and the presence of other materials, but can include aldehydes, ketones, organic acids, and other compounds.
• 粘度：
  34 cP at 20 °C; 22.7 cP at 25 °C
• 燃烧热：
  30.4 kJ/g at 25 °C (est)
• 汽化热：
  319 J/g at normal boiling point
• 表面张力：
  38.1 dynes/cm at 20 °C
• 折光率：
  Index of Refraction: 1.5232 at 20 °C
• 相对蒸发率：
  <0.01 (n-Butyl acetate = 1.0)
• 保留指数：
  1214.8

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

ADMET

代谢

液相色谱(LC)峰中暂时鉴定出的尿代谢物如下：LC峰A(<1%) - 醌葡萄糖苷酸结合物；LC峰B(1-2%) - 未鉴定；LC峰C(1.3-3.8%) - 未鉴定；LC峰D(<1%) - 未鉴定；LC峰E/F(60-63%) - 苯酚的硫酸盐和谷胱甘肽结合物；对苯基的硫酸盐和葡萄糖苷酸结合物，环羟基化对苯基和1-苯氧基-2-丙酮的硫酸盐结合物；LC峰G(<1%) - 未鉴定；LC峰H(1-2%) - 未鉴定；LC峰I(4-5%) - 对苯基的葡萄糖苷酸结合物；LC峰J(<1%) - 未鉴定；LC峰K(8-9%) - 对苯基的葡萄糖苷酸结合物；LC峰L(9-10%) - 对苯基的硫酸盐结合物。根据与真实材料的色谱保留时间比较，尿液经酸水解后得到自由的苯酚(61%)、氢醌(1.5%)和母体对苯基(13%)。

The following urinary metabolites were tentatively identified within Liquid Chromatography (LC) peaks using HPLC/ESI/MS and HPLC/ESI/MS/MS techniques: LC Peak A (<1%) - Glucuronide conjugate of hydroquinone LC Peak B (1-2%) - Not identified LC Peak C (1.3-3.8%) - Not identified LC Peak D (<1%) - Not identified LC Peak E/F (60-63%) - Sulfate and glutathione conjugates of phenol; Sulfate and glucuronide conjugates of PPh, sulfate conjugates of ring-hydroxylated PPh and 1- phenoxy-2-propanone LC Peak G (<1%) - Not identified LC Peak H (1-2%) - Not identified LC Peak I (4-5%) - Glucuronide conjugate of PPh LC Peak J (<1%) - Not identified LC Peak K (8-9%) - Glucuronide conjugate of PPh LC Peak L (9- 10%) - Sulfate conjugate of PPh Based on comparisons of chromatographic retention times with authentic materials, acid hydrolysis of urine yielded free phenol (61%), hydroquinone (1.5%), and parent PPh (13%).

来源:Hazardous Substances Data Bank (HSDB)

代谢

PPh在雄性大鼠体内被迅速吸收、分布，并且快速代谢和消除。几乎所有的给药剂量在48小时内通过尿液和粪便排出。三条主要的代谢途径是：1) PPh通过O-脱烷基裂解，生成丙二醇和酚，随后酚以硫酸盐或与谷胱甘肽结合的形式在尿液中排出；2) 父本PPh直接与硫酸或葡萄糖醛酸结合并排入尿液中；3) 父本PPh或其氧化丙酮代谢产物的环羟基化，随后与硫酸结合并排入尿液中。尿液中的次要代谢物包括氢醌的葡萄糖醛酸结合物。

PPh is rapidly absorbed, distributed, and quickly metabolized and eliminated in male rats. Virtually all the administered dose is eliminated within 48 hours in the urine and feces. The three major routes of metabolism are 1) cleavage of PPh by O-dealkylation, yielding propylene glycol and phenol, followed by excretion of phenol as a sulfate, or glutathione conjugate in the urine; 2) direct sulfate or glucuronide conjugation of parent PPh and excretion into the urine; and 3) ring hydroxylation of parent PPh or its oxidized propanone metabolite, followed by sulfate conjugation and excretion into the urine. Minor urinary metabolites included the glucuronide conjugate of hydroquinone.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

神经毒素 - 急性溶剂综合征

Neurotoxin - Acute solvent syndrome

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 毒性数据

大鼠LC50 > 5,400 mg/m³/4小时

LC50 (rat) > 5,400 mg/m3/4hr

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中和。如果患者停止呼吸，请开始人工呼吸，最好使用需求阀复苏器、球囊阀面罩设备或口袋面罩，按训练操作。如有必要，执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果发生呕吐，让患者前倾或将其置于左侧（如果可能，头部向下）以保持呼吸道畅通，防止窒息。保持患者安静，维持正常体温。寻求医疗帮助。 /毒物A和B/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有需要，辅助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，如有必要，进行治疗……。监测休克，如有必要，进行治疗……。预防癫痫发作，如有必要，进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用0.9%的生理盐水（NS）持续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的干呕反射且不流口水，则用温水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……。在去污后，用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于无意识、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的正压通气技术可能有益。考虑使用药物治疗肺水肿……。对于严重的支气管痉挛，考虑给予β激动剂，如沙丁胺醇……。监测心率和必要时治疗心律失常……。开始静脉输注D5W /SRP: "保持开放"，最低流量/。如果出现低血容量的迹象，使用0.9%生理盐水（NS）或乳酸林格氏液。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象……。使用地西泮或劳拉西泮治疗癫痫……。使用丙美卡因氢氯化物协助眼部冲洗……。 /Poisons A and B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

PPh迅速被吸收，分布到全身，代谢并排出体外。主要的排泄途径是通过尿液和粪便。

PPh is rapidly absorbed, distributed throughout the body, metabolized, and eliminated. The major routes of elimination are via the urine and feces.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xi
• 危险类别码：
  R36
• WGK Germany：
  1
• RTECS号：
  UB8886500
• 安全说明：
  S23,S26
• 危险性防范说明：
  P280,P305+P351+P338,P337+P313
• 危险性描述：
  H319

制备方法与用途

用途

1-苯氧基-2-丙醇是一种有用的合成中间体，主要用于制备酰基芳基硫代氨基甲酸酯，作为非核苷类逆转录酶抑制剂。

化学性质

它呈现为透明的粘稠液体。沸点在243℃下记录，分别在125-135℃/2.8kPa和104-114℃ /1.3kPa之间变化；相对密度为1.463；折光率为1.5243至1.5245；闪点超过110℃。

用途

它是苯氧苄胺（酚苄明）的合成中间体之一。

生产方法

该化合物通过将苯酚与环氧丙烷在氯化钠的参与下反应，然后进行醚化得到。

反应信息

• 作为反应物：
  描述：

  1-苯氧基-丙醇 在 4-acetamido-2,2,6,6-tetramethylpiperidin-1-oxoammonium nitrate 作用下， 以 neat (no solvent) 为溶剂， 以78 %的产率得到苯氧基丙酮
  参考文献：
  名称：

  使用带有硝酸根阴离子的氧铵盐快速、轻松地氧化�