4-Aminosalicylic Acid 对氨基水杨酸

CAS 65-49-6 MFCD00007789

化学结构图

65-49-6
SMILES: Nc1ccc(C(=O)O)c(O)c1

化学属性

Mol. FormulaC7H7NO3
Mol. Weight153.14
Density1.545
Melting Point135-145°C
TSCAYes
SolubilitySoluble in water (2 g/l) at 20 °C, dilute sodium hydroxide, dilute nitric acid, ether (slightly), methanol, acetone, and ethanol (1 G SOL IN 21 ML ALC). Virtually insoluble in benzene, chloroform, and carbon tetrachloride
Stability对光和空气敏感
Appearance 白色结晶。熔点为150-151℃(分解)。无臭或微有丙酮气味。溶于稀硝酸、稀氢氧化钠、丙酮、碳酸氢钠和磷酸,稍溶于乙醇,微溶于乙醚,不溶于水及苯。在40℃时该品水溶液不稳定,分解放出二氧化碳而生成氨基酚。暴露于空气中变为棕色。
Boiling Point276.03 °C at 760 mmHg

别名和识别编码

Chemical Name4-Aminosalicylic Acid
CAS Number65-49-6
Alfabeta NameAMINOHYDROXYBENZOICACID 42---
MDL NumberMFCD00007789
Synonym 4-Aminosalicylic acid {LY} 4-Aminosalicylic acid {} {LY} 4-Aminosalicylic acid {} {} {LY} 4-Aminosalicylic acid {} {} {} {LY} 4-Aminosalicylic acid {} {} {} {} {LY} 4-Aminosalicylic acid {} {} {} {} {} {LY} 4-Aminosalicylic acid {} {} {} {} {} {} {LY} 4-Aminosalicylic acid {} {} {} {} {} {} {} {LY} 4-Aminosalicylic acid {} {} {} {} {} {} {} {} {LY} 4-Aminosalicylic acid {} {} {} {} {} {} {} {} {} {LY} 4-Aminosalicylic acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 4-Aminosalicylic acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 4-Aminosalicylic acid {} {} {} {} {} {} {} {} {} {} {} {} {LY} 4-Aminosalicylic acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 4-Aminosalicylic acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 4-Aminosalicylic acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
EC Number200-613-5
Beilstein Registry Number473071
PubChem Substance ID87562054
Merck Number477
Reaxys-RN473071
Chemical Name Translation对氨基水杨酸
Wiswesser Line NotationZR CQ DVQ
LabNetwork Molecule IDLN00175003
Canonical SMILESO=C(O)C1=CC=C(N)C=C1O
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分类

  • {SNA} Aromatic Amino Acids, Chemical Biology, Chemical Synthesis, Peptide Chemistry, Unnatural Amino Acid Derivatives
  • {SNA} A-AM, Aromatic Amino Acids, Bioactive Small Molecules, Cell Biology, Chemical Biology, Chemical Synthesis, Peptide Chemistry, Unnatural Amino Acid Derivatives
  • {SNA} A-AM, Aromatic Amino Acids, Bioactive Small Molecules, Chemical Biology, Chemical Synthesis, Peptide Chemistry, Unnatural Amino Acid Derivatives, 细胞生物学
  • {uni_hamburg} no charge; carbocycle; aromatic; 6RingOnly; 6ring; carboxylic acid; alcohol; 1fragment
  • Pharmaceuticals
  • {SNA} Aromatic Amino Acids, Chemical Biology, Chemical Synthesis, Peptide Chemistry,

产品应用

  • A antibacterial capable of inhibiting the growth of Mycobacterium tuberculosis

相关文献及参考

  • Fourches, D., et al.: Chem. Res. Toxicol., 23, 171 (2010),
  • Horita, Y., et al.: Bioorg. Med. Chem. Lett., 19, 6313 (2009),
  • Short: II/27C
  • Merck: 14,477
  • Merck: 14,477 Beilstein:14(3)1436
  • Short: II/27B
  • Martins, M., et al.: J. Biol. Chem., 284, 18726 (2009),

安全信息

Warnings IRRITANT
Signal word Warning
GHS Symbol
WGK Germany2
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
Risk Statements
  • R22 Harmful if swallowed 吞咽有害
  • R36 Irritating to eyes 刺激眼睛
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R45 May cause cancer 可能致癌
Precautionary statements
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P302+P350
  • P302+P352+P332+P313+P362+P364
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感觉不适,呼叫解毒中心或医生/医师。
  • P332+P313
  • P337+P313
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服,清洗后方可重新使用
Hazard statements
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H303 May be harmfully swallowed 吞食可能有害
RTECSVO1225000
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes Xn,Xi,T Xn Xi
Storage condition Store at room temperature {LY} Store at room temperature {} {LY} Store at room temperature {} {} {LY} Store at room temperature {} {} {} {LY} Store at room temperature {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room te
UN Number UN 1789 8/PG 3
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
REFERENCE :
   JPPMAB Journal of Pharmacy and Pharmacology.  (Pharmaceutical Soc. of Great
   Britain, 1 Lambeth High St., London SEI 7JN, UK)  V.1-    1949-
   Volume(issue)/page/year: 2,764,1950

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : R

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
REFERENCE :
   JPPMAB Journal of Pharmacy and Pharmacology.  (Pharmaceutical Soc. of Great
   Britain, 1 Lambeth High St., London SEI 7JN, UK)  V.1-    1949-
   Volume(issue)/page/year: 2,764,1950

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
REFERENCE :
   ANTBAL Antibiotiki.  (Moscow, USSR)  V.1-29, 1956-84.  For publisher
   information, see AMBIEH.  Volume(issue)/page/year: 18,249,1973

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
REFERENCE :
   FEPRA7 Federation Proceedings, Federation of American Societies for
   Experimental Biology. (Bethesda, MD)  V.1-46, 1942-87.
   Volume(issue)/page/year: 10,289,1951

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

TYPE OF TEST            : Cytogenetic analysis
ROUTE OF EXPOSURE       : Oral
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 50 mg/kg
REFERENCE :
   NULSAK Nucleus (Calcutta).  (Dr. A.K. Sharma, Centre of Advanced Studies in
   Cell and Chromosome Research, Calcutta, 35 Baliygunge Circular Rd., Calcutta
   700 019, India)  V.1-    1958-  Volume(issue)/page/year: 22,96,1979

其他信息

  • 用途一:作为镀锌光亮剂,整平剂和匀镀剂,用于碱性镀锌
  • 4-Aminosalicylic acid is an inhibitor of NF κ B.
  • TCI Shanghai:4-氨基水杨酸 4-Aminosalicylic Acid,>;97.0%(T)(65-49-6)
  • 毒性分级:中毒
  • Sigma Aldrich:65-49-6(sigmaaldrich)
  • 用途四:有机合成。医药。医药中间体,用于合成抗结核病药对氨柳酸钠。也用于分析出试剂酸碱荧光指示剂。
  • 刺激数据:眼睛-兔子 100 毫克/24小时 中度
  • {Chemicalbook
  • 可燃性危险特性:可燃;燃烧产生有毒氮氧化物烟雾
  • 类别:有毒物品
  • MOL 文件:65-49-6.mol
  • 急性毒性:腹腔-小鼠LD50: 4250 毫克/公斤;口服-小鼠LD50: 4000 毫克/公斤
  • 下游产品:双烯大分子单体共聚物光学塑料 --> 4-乙酰氨基-2-甲氧基苯甲酸甲酯 --> 对乙酰氨基-邻甲氧基苯甲酸甲酯 --> 4-氯水杨酸
  • 可燃性危险特性:可燃;燃烧产生有毒氮氧化物
  • {
  • 用途二:医药中间体,用于合成抗结核药对氨基水杨酸钠
  • 图谱信息:4-氨基水杨酸(65-49-6)红外图谱(IR1) 4-氨基水杨酸(65-49-6)质谱(MS) 4-氨基水杨酸(65-49-6)红外图谱(IR2)
  • 储运特性:库房通风低温干燥
  • 对光敏感。露于空气中易变棕色。溶解度: 2 g/L水 (20°C)、1g/21ml乙醇,溶于稀硝酸、稀氢氧化钠溶液,微溶于乙醚,几乎不溶于苯。
  • 上游原料:硝酸 --> 甲醇钠 --> 二氧化碳 --> 亚硫酸钠 --> 硫化钠 --> 氢氧化钾溶液 --> 苯乙酸 --> 3-氨基苯酚 --> 酯化物 --> 邻羟基苯甲腈 --> 亚硝酸丁酯 --> 2,4-二硝基苯乙酸甲酯 --> 2,4-二硝基苯乙酸 --> 4-硝基水杨酸
  • 用途三:医药中间体,用于合成抗结核病药对氨柳酸钠。也用于分析出试剂酸碱荧光指示剂。
  • Acros Organics:4-氨基水杨酸 4-Aminosalicylic acid, 99%(65-49-6)
  • 4-氨基水杨酸价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 L0983201 4-氨基水杨酸98% 100g 1
  • 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。

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