Trifluoroacetic acid 三氟乙酸

CAS 76-05-1 MFCD00004169

化学结构图

76-05-1
SMILES: O=C(O)C(F)(F)F

化学属性

Refractive indexn20/D 1.3(lit.)
TSCAYes
SolubilityMiscible with ether, acetone, ethanol, benzene, hexane, CCl4
Vapor Density3.9 (vs air)
Vapor Pressure97.5 mmHg ( 20 °C)
Flash PointNone
Stability对湿度敏感
Mol. FormulaC2HF3O2
Mol. Weight114.02
Density1.478
Appearance colorless liq.
Boiling Point72
Melting Point-15
pH:A

别名和识别编码

Chemical NameTrifluoroacetic acid
Synonym Aceticacid,trifluoro- BUFFER A CF3COOH IPC-PFFA-2 Kyselina trifluoroctova PERFLUOROACETIC ACID Perfluoroacetic acid R3, TRIFLUOROACETIC ACID R4A, TRIFLUOROACETIC ACID RARECHEM AL BO 0421 TFA TRIFLUOROACETIC ACID TRIFLUOROACETLC ACID Trifluoracetic acid Trifluoressigs~ure Trifluoroethanoic acid WASH BUFFER kyselinatrifluoroctova trifluoraceticacid trifluoro-aceticaci trifluoroaceticacid99,5% 三氟乙酸 三氟乙酸 溶液 三氟乙酸, 99% 三氟乙酸, BIOCHEMICAL GRADE, 99.5+% 三氟乙酸,生化级 三氟乙酸(TFA) 三氟醋酸 三氟醋酸;过氟乙酸;全氟醋酸 全氟醋酸
EC Number200-929-3
Beilstein Registry Number742035
PubChem Substance ID87576383
Reaxys-RN742035
Merck Number9681
Chemical Name Translation三氟乙酸
Wiswesser Line NotationQVXFFF
LabNetwork Molecule IDLN00162790
InChIInChI=1S/C2HF3O2/c3-2(4,5)1(6)7/h(H,6,7)
MDL NumberMFCD00004169
CAS Number76-05-1
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分类

  • {SNA} Alpha Sort, Alphabetical Index of Analytical Standards, Analytical Standards, Analytical/Chromatography, Chromatography, Environmental Standards, Food & Beverage Standards, Organic Acids, T, T-Z, TP - TZ, Volatiles/ Semivolatiles
  • {SNA} Acids, Acids & Bases, Analytical Reagents, Analytical/Chromatography, Chemical Synthesis, Chromatography Reagents & Solvents, LC-MS Mobile Phase Additives, LC-MS Solvents & Reagents (CHROMASOLV), Mass Spectrometry (MS), Organic Acids, Reagents for Mass Spectrometry (MS), Spectroscopy, Synthetic Reagent

产品应用

  • 三氟乙酰化试剂,聚合反应催化剂。与液体二氧化硫混和用以溶解蛋白质。分光光度分析。蛋白质顺序分析。
  • 在反相色谱分离多肽和蛋白质的实验中,使用三氟乙酸 (TFA) 作为离子对试剂是常见的手段。流动相中的三氟乙酸通过与疏水键合相和残留的极性表面以多种模式相互作用,来改善峰形、克服峰展宽和拖尾问题。
  • 三氟乙酸优于其他离子修饰剂的原因是它容易挥发,可以方便地从制备样品中除去。另一方面,三氟乙酸的紫外最大吸收峰低于 200nm ,对多肽在低波长处的检测干扰很小。
  • 三氟乙酸(TFA)是许多有机化合物的良好溶剂,如与二硫化碳合用,可溶解蛋白质。它也是有机反应的优良溶剂,可获得在一般溶剂中难以获得的结果,例如喹啉在一般溶剂中催化氢化时,吡啶环优先氢化,但在三氟乙酸中苯环优先氢化。三氟乙酸在苯胺存在下分解成氟仿和二氧化碳。

相关文献及参考

  • With sodium nitrite, has been used for the cleavage of tosylhydrazones: Synthesis, 207 (1979); for nitrosation of anisole and derivatives, avoiding possible loss of the alkyl group: Acta Chem. Scand., 44, 152 (1990); for diazotization of weakly basic arylamines such as pentafluoroaniline or 3,5-dinitroaniline: Synthesis, 566 (1988); and in the presence of formamide, for deamination of arylamines: J. Chem. Soc., Perkin 1, 873 (1986).
  • Carrying out the Curtius rearrangement of acyl azides in TFA leads directly to the trifluoroacetamide, which can be readily hydrolyzed to the free amine: Synthesis, 38 (1983).
  • Merck: 14,9681 Beilstein: 2,IV,458
  • Also catalyzes the cleavage of t-butyl groups from t-butylphenols, by reverse Friedel-Crafts reaction: Tetrahedron, 29, 4003 (1973). Similarly, hindered aryl ketones or aromatic carboxylic acids undergo deacylation: Synthesis, 979 (1985).
  • Merck: 14,9681
  • Strong organic acid, widely used in peptide synthesis to cleave N-Boc and t-butyl ester groups: Helv. Chim. Acta, 46, 870 (1963); see also Org. Synth. Coll., 9, 24, 268 (1998). For peptide reagents, see Appendix 6. For selective cleavage of Boc in the presence of Cbz (Z), using 70% TFA in water, see: Liebigs Ann. Chem., 749, 90 (1971). For selective cleavage of benzyl, benzhydryl and trityl ethers in the presence of ester functions, see: Synthesis, 249 (1983).
  • For use of TFA as a catalyst in the Meerwein-Ponndorf-Verley reduction, see Aluminum isopropoxide, 14007. For use in the modification of the reducing properties of borohydride, see Sodium

安全信息

Signal word Danger
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;
  • S27 Take off immediately all contaminated clothing 立即脱掉全部污染的衣服;
  • S28 After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) 皮肤接触后,立即用大量…(由生产厂家指定)冲洗;
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时,立即求医(可能时出示标签);
  • S61 Avoid release to the environment. Refer to special instructions/safety data sheet 避免释放到环境中,参考特别指示/安全收据说明书;
  • S9 Keep container in a well-ventilated place 保持容器在通风良好的场所;
Risk Statements
  • R20 Harmful by inhalation 吸入有害
  • R35 Causes severe burns 会导致严重灼伤
  • R52/53
Precautionary statements
  • P234 Keep only in original container. 只保留在原来的容器中。
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • 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。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P273 Avoid release to the environment. 避免释放到环境中。
  • 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。
  • P301+P330+P331+P310
  • P303+P361+P353+P310+P363
  • P304+P340+P310
  • P305+P351+P338
  • P305+P351+P338+P310
  • P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或医生/医师。
  • P390 Absorb spillage to prevent material damage. 吸收溢出物,防止重大损害。
  • P405 Store locked up. 上锁保管。
  • P406 Store in corrosive resistant/… container with a resistant inner liner. 存放在耐腐蚀/具有耐性的内衬容器。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard Codes 8 C
Hazard statements
  • H290 May be corrosive to metals 可能腐蚀金属。
  • H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
  • H332 Harmful if inhaled 吸入有害
  • H412 Harmfutoaquaticlifewithlonglastingeffects 对水生生物有害并具有长期影响。
Personal Protective Equipment Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
RTECSAJ9625000
UN Number 2699
Storage condition Hygroscopic 密封阴凉干燥保存。 2-8°C 充氩保存
Packing GroupI
Hazard Class8
TYPE OF TEST            : LC50 - Lethal concentration, 50 percent kill
ROUTE OF EXPOSURE       : Inhalation
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 10 gm/m3
TOXIC EFFECTS :
   Sense Organs and Special Senses (Eye) - conjunctive irritation
   Behavioral - somnolence (general depressed activity)
   Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
   GTPZAB Gigiena Truda i Professional'nye Zabolevaniya.  Labor Hygiene and
   Occupational Diseases. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR)
   V.1-36, 1957-1992. For publisher information, see MTPEEI
   Volume(issue)/page/year: 10(3),13,1966

TYPE OF TEST            : LC50 - Lethal concentration, 50 percent kill
ROUTE OF EXPOSURE       : Inhalation
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 13500 mg/m3
TOXIC EFFECTS :
   Sense Organs and Special Senses (Eye) - conjunctive irritation
   Behavioral - somnolence (general depressed activity)
   Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
   GTPZAB Gigiena Truda i Professional'nye Zabolevaniya.  Labor Hygiene and
   Occupational Diseases. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR)
   V.1-36, 1957-1992. For publisher information, see MTPEEI
   Volume(issue)/page/year: 10(3),13,1966

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1200 mg/kg
TOXIC EFFECTS :
   Behavioral - changes in motor activity (specific assay)
REFERENCE :
   AMEBA7 Annales Medicinae Experimentalis et Biologiae Fenniae.  (Helsinki,
   Finland)  V.25-51, 1947-73. For publisher information, see MDBYAS.
   Volume(issue)/page/year: 46,242,1968

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 500 mg/kg
TOXIC EFFECTS :
   Sense O

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 1650 mg/kg
SEX/DURATION            : female 10-20 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - hepatobiliary system
   Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight
   gain)
REFERENCE :
   JJATDK JAT, Journal of Applied Toxicology.  (John Wiley & Sons Ltd., Baffins
   Lane, Chichester, W. Sussex PO19 1UD, UK)  V.1-    1981-
   Volume(issue)/page/year: 17,1,1996

Warnings 危化品目录(2015)
Restrict 危险品

其他信息

  • 蒸气压:97.5 mm Hg ( 20 °C)
  • 下游产品:吡啶-3-亚甲基肼,1-(3-吡啶基)甲基肼 --> 1-(3-吡咯烷丙基)哌嗪 --> 头孢布烯 --> 醋酸奥曲肽 --> 齐拉西酮 --> 阿贝卡星 --> (S)-2-甲基脯氨酸 --> 1-叔丁基-3-三氟甲基-1H-吡唑 --> 4-氯-5-氨基-6-肼基嘧啶 --> 4,5-二氨基-6-氯嘧啶 --> 1-甲基-5-三氟甲基-1H-吡唑 --> 4
  • {Chem
  • {
  • 上游原料:乙酐 --> 氢氟酸 --> 三氟甲苯 --> 三氟丙烯 --> 三氯乙腈 --> 三氟乙腈 --> 六氟-2,3-二氯-2-丁烯
  • 毒性分级:中毒
  • 方法一:1.以2,3-二氯六氟-2-丁烯氧化制取;2.以氟为催化剂对2,3-二氯六氟-2-丁烯进行氧化以制取之;3.由3,3,3-三氟丙烯经高锰酸钾氧化、或由三氯乙腈与氟化氢反应生成三氟乙腈继而水解、或将乙酸
  • {Chemical
  • 用途四:三氟乙酰化试剂,聚合反应催化剂。与液体二氧化硫混和用以溶解蛋白质。分光光度分析
  • F:3
  • 有辛辣气味。有吸湿性。能发烟。是一种强烈而非氧化性的酸。能与乙醚、丙酮、乙醇、苯、四氯化碳和己烷混溶。有毒,半数致死量(小鼠,静脉)1200mg/kg。有腐蚀性。
  • 制备方法与生产工艺:三氟乙酸是重要的有机合成试剂,由它可以合成各种含氟化合物、杀虫剂和染料。三氟乙酸也是酯化反应和缩合反应的催化剂;还可作为羟基和氨基的保护剂,用于糖和多肽的合成
  • 用途三:该品是许多有机化合物的良好溶剂,与二硫化碳合用,可溶解蛋白质。也是有机反应的优良溶剂。可获得在
  • pKa:三氟乙酸(TFA).是一种强羧酸,pKa=0.23,能够刺激人体组织和皮肤.只有轻微的毒性,但是在不流动的地表水中富集则会影响农业和水生系统,并且TFA经历微生物降解产生温室气体CHF3.
  • 用途四:三氟乙酰化试剂,聚合反应催化剂。与液体二氧化硫混和用以溶解蛋白质。分光光度分析。蛋白质顺序分析。 在反相色谱分离多肽和蛋白质的实验中,使用三氟乙酸 (TFA) 作为离子对试剂是常见的手段。流动相中的三氟乙酸通过与疏水键合相和残留的极性表面以多种模式相互作用,来改善峰形、克服峰展宽和拖尾问题。 三氟乙酸优于其他离子修饰剂的原因是它容易挥发,可以方便地从制备样品中除去。另一方面,三氟乙酸的紫外最大吸收峰低于 200nm ,对多肽在低波长处的检测干扰很小。 三氟乙酸(TFA)是许多有机化合物的良好溶剂,如与二硫化碳合用,可溶解蛋白质。它也是有机反应的优良溶剂,可获得在一般溶剂中难以获得的结果,例如喹啉在一般溶剂中催化氢化时,吡啶环优先氢化,但在三氟乙酸中苯环优先氢化。三氟乙酸在苯胺存在下分解成氟仿和二氧化碳。
  • 下游产品:吡啶-3-亚甲基肼,1-(3-吡啶基)甲基肼 --> 1-(3-吡咯烷丙基)哌嗪 --> 头孢布烯 --> 醋酸奥曲肽 --> 齐拉西酮 --> 阿贝卡星 --> (S)-2
  • 概述:三氟乙酸(TFA分子式:CF3COOH)别名三氟醋酸,无色挥发性发烟液体,与乙酸气味类似,有吸湿性和刺激性臭味。受吸电子性的三氟甲基的影响而有强酸性,酸性比乙酸强十万倍。熔点-15.2℃,沸点72.4℃,密度1.5351克/厘米3(1℃)。与水、氟代烃、甲醇、乙醇、乙醚、丙酮、苯、四氯化碳、己烷混溶,可部分溶解二硫化碳和六碳以上烷烃,是蛋白质和聚酯的优良溶剂。它也是有机反应的优良溶剂,可获得在一般溶剂中难以获得的结果,例如喹啉在一般溶剂中催化氢化时,吡啶环优先氢化,但在三氟乙酸中苯环优先氢化。三氟乙酸在苯胺存在下分解成氟仿和二氧化碳。能被硼氢化钠或氢化铝锂还原为三氟乙醛和三氟乙醇。在205℃以上稳定,酯类和酰胺类衍生物容易水解,因此能以酸或酸酐的形式,制取糖类、氨基酸和肽类衍生物。容易在五氧化二磷作用下脱水为三氟乙酸酐。 三氟乙酸是一种重要的脂肪含氟中间体,由于含有三氟甲基的特殊结构,因此使其性质不同于其他醇类,可以参与多种有机合成反应,尤其用于合成含氟的医药、农药和染料等领域,国内外需求量越来越大,已成为含氟精细化学品的重要的中间体之一。
  • {Ch
  • 急性毒性:吸入-大鼠 LC50:10000 毫克/

系列性分类


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