65-49-6

• 常用中文名：对氨基水杨酸
• 常用英文名：4-aminosalicylic acid
• CAS号：65-49-6
• 分子式：C₇H₇NO₃
• 分子量：153.135
• 相关类别： 原料药 人工合成抗感染类药 抗结核麻风分支杆菌类药
• 发布时间：2018-06-08 19:27:07
• 更新时间：2024-01-03 01:00:44
• 4-Aminosalicylic acid 是具有口服活性的抗生素,可用于肺结核病的研究。

名称

• 中文名: 4-氨基水杨酸
• 英文名: 4-aminosalicylic acid
• 中文别名: 4-氨基-2-羟基苯甲酸; 对氨基水杨酸; 4-氨基柳酸
• 英文别名: PAS; 4-Asa; Bactylan; Pasalon-rakeet; Aminox; Tubersan; para-amino salicylic acid; Salvis; Paracipan; 4-Amino-2-hydroxybenzoic acid; Sanipirol; Lepasen; PASA; Apas; Pasmicina; p-aminosalicylic acid; Benzoic acid, 4-amino-2-hydroxy-; Rezipas; 4-amino-salicylic acid; EINECS 200-613-5; ZR CQ DVQ; Passodico; PASK; 4-Aminosalicylic acid; MFCD00007789; A 1909; Aminosalicylic Acid; Aminacyl; Paser; PAS-C; Pasem; Mesalazine Impurity 5

物化性质

• 密度: 1.5±0.1 g/cm3
• 沸点: 380.8±32.0 °C at 760 mmHg
• 熔点: 135-145 °C(lit.)
• 分子式: C₇H₇NO₃
• 分子量: 153.135
• 闪点: 184.1±25.1 °C
• 精确质量: 153.042587
• PSA: 83.55000
• LogP: 1.14
• 外观性状: 微小的晶体，无气味的,或有淡醋的气味
• 蒸汽压: 0.0±0.9 mmHg at 25°C
• 折射率: 1.691
• 储存条件:

  本品应密封避光保存。

• 水溶解性: 2 g/L (20 ºC)
• 分子结构:

  1、 摩尔折射率：39.30

  2、 摩尔体积（cm³/mol）：102.6

  3、 等张比容（90.2K）：310.2

  4、 表面张力（dyne/cm）：83.3

  5、 极化率（10^-24cm³）：15.57

• 计算化学:

  1、 疏水参数计算参考值（XlogP）：1.3

  2、 氢键供体数量：3

  3、 氢键受体数量：4

  4、 可旋转化学键数量：1

  5、 互变异构体数量：12

  6、 拓扑分子极性表面积（TPSA）：83.6

  7、 重原子数量：11

  8、 表面电荷：0

  9、 复杂度：160

  10、 同位素原子数量：0

  11、 确定原子立构中心数量：0

  12、 不确定原子立构中心数量：0

  13、 确定化学键立构中心数量：0

  14、 不确定化学键立构中心数量：0

  15、 共价键单元数量：1

• 更多:

  1. 性状：白色结晶性粉末。无气味或微有酸的气味。对光敏感。露于空气中易变为棕色。

  2. 密度（g/mL,25/4℃）： 1.371

  3. 相对蒸汽密度（g/mL,空气=1）：未确定

  4. 熔点（ºC）：150～151（分解并起泡）

  5. 沸点（ºC,常压）：未确定

  6. 沸点（ºC,5.2kPa）：未确定

  7. 折射率：1.652

  8. 闪点（ºC）：未确定

  9. 比旋光度（º）：未确定

  10. 自燃点或引燃温度（ºC）：未确定

  11. 蒸气压（kPa,25ºC）：未确定

  12. 饱和蒸气压（kPa,60ºC）：未确定

  13. 燃烧热（KJ/mol）：未确定

  14. 临界温度（ºC）：未确定

  15. 临界压力（KPa）：未确定

  16. 油水（辛醇/水）分配系数的对数值：未确定

  17. 爆炸上限（%,V/V）：未确定

  18. 爆炸下限（%,V/V）：未确定

  19. 溶解性：40℃以上时水溶液不稳定，分解并放出二氧化碳而成为间氨基酚。1g产品溶于21ml乙醇、约500ml水。溶于稀硝酸、稀氢氧化钠溶液，微溶于乙醚，几乎不溶于苯。

生物活性

• 描述: 4-Aminosalicylic acid 是具有口服活性的抗生素,可用于肺结核病的研究。
• 相关类别:
  研究领域 >> 感染
  研究领域 >> 炎症/免疫
  信号通路 >> 抗感染 >> 细菌
• 参考文献:

  [1]. Vânia André, et al. Crystal Forms of the Antibiotic 4-Aminosalicylic Acid: Solvates and Molecular Salts with Dioxane, Morpholine, and Piperazine. Cryst. Growth Des. 2009, 9, 12, 5108-5116.

MSDS

Name: 4-Aminosalicylic acid 99% Material Safety Data Sheet Synonym: PAS; 4-Amino-2-hydroxybenzoic aci CAS: 65-49-6 Section 1 - Chemical Product MSDS Name:4-Aminosalicylic acid 99% Material Safety Data Sheet Synonym:PAS; 4-Amino-2-hydroxybenzoic aci Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS CAS# Chemical Name content EINECS# 65-49-6 4-aminosalicylic acid 99.0 200-613-5 Hazard Symbols: None Listed. Risk Phrases: None Listed. Section 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Light sensitive.Air sensitive. Potential Health Effects Eye: Causes eye irritation. Skin: May cause skin irritation. Ingestion: May cause irritation of the digestive tract. Inhalation: May cause respiratory tract irritation. Chronic: No information found. 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. Skin: Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists. 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. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. 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 if cough or other symptoms appear. Get medical aid. Notes to Physician: Antidote: None reported. 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 agent most appropriate to extinguish fire. Section 6 - ACCIDENTAL RELEASE MEASURES General Information: Use proper personal protective equipment as indicated in Section 8. Spills/Leaks: Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions. Provide ventilation. Place under an inert atmosphere. Section 7 - HANDLING and STORAGE Handling: Wash thoroughly after handling. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Store protected from light. Handle under an inert atmosphere. Store protected from air. Storage: Store in a cool, dry, well-ventilated area away from incompatible substances. Do not expose to air. Store protected from light. Store under an inert atmosphere. Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION Engineering Controls: Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 65-49-6: 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: A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use. 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. Section 9 - PHYSICAL AND CHEMICAL PROPERTIES Physical State: Solid Color: Not available. Odor: Odorless or slight acetous pH: Not available. Vapor Pressure: Not available. Viscosity: Not available. Boiling Point: Not available. Freezing/Melting Point: 147 deg C dec Autoignition Temperature: Not available. Flash Point: Not available. Explosion Limits, lower: Not available. Explosion Limits, upper: Not available. Decomposition Temperature: Solubility in water: practically insoluble in benzene Specific Gravity/Density: Molecular Formula: C7H7NO3 Molecular Weight: 153.14 Section 10 - STABILITY AND REACTIVITY Chemical Stability: Stable under normal temperatures and pressures. Conditions to Avoid: Incompatible materials, light, exposure to air. Incompatibilities with Other Materials: Air. Hazardous Decomposition Products: Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide. Hazardous Polymerization: Has not been reported. Section 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 65-49-6: VO1225000 LD50/LC50: CAS# 65-49-6: Draize test, rabbit, eye: 100 mg/24H Moderate; Oral, mouse: LD50 = 4 gm/kg; Oral, rabbit: LD50 = 3650 mg/kg. Carcinogenicity: 4-aminosalicylic acid - Not listed by ACGIH, IARC, or NTP. Other: See actual entry in RTECS for complete information. Section 12 - ECOLOGICAL INFORMATION Section 13 - DISPOSAL CONSIDERATIONS Dispose of in a manner consistent with federal, state, and local regulations. 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. 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# 65-49-6: No information available. Canada CAS# 65-49-6 is listed on Canada's NDSL List. CAS# 65-49-6 is listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 65-49-6 is listed on the TSCA inventory. SECTION 16 - ADDITIONAL INFORMATION N/A

毒性和生态

毒理学数据: 急性毒性：小鼠口经LD50：4 mg/kg；小鼠腹腔LD50：4250 mg/kg；小鼠皮下注射LD50：4 mg/kg； 小鼠静脉LD50：3898 mg/kg；兔子口经LD50：3650 mg/kg； 致突变：小鼠口经Cytogenetic 分析：50 mg/kg； 皮肤/眼睛刺激：兔子Administration into the eye标准Draize测试：100 mg/24HREACTION SEVERITY : Moderate CHEMICAL IDENTIFICATION RTECS NUMBER : VO1225000 CHEMICAL NAME : Salicylic acid, 4-amino- CAS REGISTRY NUMBER : 65-49-6 BEILSTEIN REFERENCE NO. : 0473071 LAST UPDATED : 199701 DATA ITEMS CITED : 11 MOLECULAR FORMULA : C7-H7-N-O3 MOLECULAR WEIGHT : 153.15 WISWESSER LINE NOTATION : ZR CQ DVQ HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : Standard Draize test ROUTE OF EXPOSURE : Administration into the eye SPECIES OBSERVED : Rodent - rabbit TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 4 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 4250 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 4 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 3898 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 3650 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : Cytogenetic analysis MUTATION DATA TYPE OF TEST : Cytogenetic analysis TEST SYSTEM : Rodent - mouse Mammary gland DOSE/DURATION : 2 mmol/L/24H (Continuous) REFERENCE : JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 5,141,1980 *** REVIEWS *** TOXICOLOGY REVIEW AJMEAZ American Journal of Medicine. (Technical Pub., 875 Third Ave., New York, NY 10022) V.1- 1946- Volume(issue)/page/year: 38,409,1965

安全

• 符号: GHS07
• 信号词: Warning
• 危害声明: H319
• 警示性声明: P305 + P351 + P338
• 个人防护装备: dust mask type N95 (US);Eyeshields;Gloves
• 危害码 (欧洲): Xi:Irritant
• 风险声明 (欧洲): R36/37/38
• 安全声明 (欧洲): S26-S37/39-S45-S53
• 危险品运输编码: UN 1789 8/PG 3
• WGK德国: 2
• RTECS号: VO1225000
• 海关编码: 29225000

合成路线

上下游产品

上游产品  10
619-19-2 591-27-5 17980-39-1 108-46-3
298-14-6 39835-14-8 43134-76-5 6018-18-4
65944-71-0 1122102-49-1
下游产品  9
106868-33-1 10462-80-3 4235-43-2 50-86-2
5106-98-9 345-29-9 35290-97-2 4093-29-2
4093-31-6

制备

【方法一】
由间氨基酚经羟化而得。将水、间氨基酚和碳酸氢钠依次投入反应罐内，通入二氧化碳置换空气后，密闭升温至110±1℃，罐内压力保持0.6-0.8MPa反应6h，冷却至-5℃，加亚硫酸钠，过滤，水洗，合并洗滤液供酸化用。滤饼为间氨基酚回收物，套用。将上述洗滤液升温至10-15℃，用30-40%硫酸中和至pH为6.4-7.0，加入适量的亚硫酸钠与硫化钠溶液，经树脂脱色后，于30℃用30-40%硫酸调节至pH为3- 3.5，放置，甩滤，水洗至硫酸根合格，甩干得对氨基水杨酸。从苯乙酸出发也可以合成得到对氨基水杨酸。先使苯乙酸在浓硫酸和浓硝酸中在60℃下硝化，然后倾入冰水中，过滤析出2,4-二硝基苯乙酸[643-43-6]。硝化产率95%。将得到的产物加入10倍甲醇中，均匀混合后，通入干燥的氯化氢，加热至沸，冷却后析出2,4-二硝基苯乙酸甲酯晶体[58605-12-2]。酯化产率为80%。将酯化物溶解于热甲醇中，加入亚硝酸丁酯，再加入甲醇钠，静置数小时直至完全析出深红色沉淀物，分离沉淀物得中间产物。将其溶于稀氢氧化钾溶液中，加入盐酸酸化，使呈酸性。逸出二氧化碳气体，析出4-硝基-2-羟基苯腈。产率为80%，将此腈化物与水、浓硫酸、冰醋酸混合加热至沸，即可析出4-硝基水杨酸[619-19-2]。将4-硝基水杨酸溶解于25%碳酸钠溶液中，加入硫酸亚铁水溶液，再加适量的碳酸钠溶液，加热至沸，分离析出铁盐。过滤，滤液用乙酸调至pH=3,4-氨基水杨酸则析出。再过滤干燥，即得产品。工业品对氨基水杨酸含量大于70%，氯化物小于50ppm，硫酸根小于500ppm。

海关

海关编码	29225000