Triethyl Orthoacetate 原乙酸三乙酯

CAS 78-39-7 MFCD00009223

化学结构图

78-39-7
SMILES: CCOC(C)(OCC)OCC

化学属性

Mol. FormulaC8H18O3
Mol. Weight162.23
Density0.885
Refractive index1.3950 to 1.3990
Boiling Point142 °C at 760 mmHg
Flash Point37°C(lit.)
TSCAYes
Solubility略溶于水
Appearance 1.3970，相对密度 0.8850，不溶于水，能与乙醇、乙醚、甲苯、乙酸乙酯、四氯化碳等有机溶剂混溶。 D 原乙酸三乙酯是无色透明液体，有挥发性醚类气味，b.p.142℃，n 20
Stability对湿度敏感

别名和识别编码

Chemical NameTriethyl Orthoacetate
Synonym 1,1,1-Triethoxyethane {LY} 1,1,1-Triethoxyethane {} {LY} 1,1,1-Triethoxyethane {} {} {LY} 1,1,1-Triethoxyethane {} {} {} {LY} 1,1,1-Triethoxyethane {} {} {} {} {LY} 1,1,1-Triethoxyethane {} {} {} {} {} {LY} 1,1,1-Triethoxyethane {} {} {} {} {} {} {LY} 1,1,1-Triethoxyethane {} {} {} {} {} {} {} {LY} 1,1,1-Triethoxyethane {} {} {} {} {} {} {} {} {LY} 1,1,1-Triethoxyethane {} {} {} {} {} {} {} {} {} {LY} 1,1,1-Triethoxyethane {} {} {} {} {} {} {} {} {} {} {LY} 1,1,1-Triethoxyethane {} {} {} {} {} {} {} {} {} {} {} {LY} 1,1,1-Triethoxyethane {} {} {} {} {} {} {} {} {} {} {} {} {LY} 1,1,1-Triethoxyethane {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 1,1,1-Triethoxyethane {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 1,1,1-Triethoxyethane {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 1,1,1-Triethoxyethane {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 1,1,1-Triethoxyethane {} {} {} {} {} {} {} {} {} {} {} {} {}
MDL NumberMFCD00009223
CAS Number78-39-7
EC Number201-112-4
Beilstein Registry Number506201
PubChem Substance ID87574111
Reaxys-RN506201
Chemical Name Translation原乙酸三乙酯
LabNetwork Molecule IDLN00196445
InChIInChI=1S/C8H18O3/c1-5-9-8(4,10-6-2)11-7-3/h5-7H2,1-4H3
Canonical SMILESCCOC(OCC)(C)OCC
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分类

  • {SNA} Acetals/Ketals/Ortho Esters, Building Blocks, Chemical Synthesis, Organic Building Blocks, Oxygen Compounds
  • {Chemicalbook} 农药中间体: 杀虫剂中间体: 拟除虫菊酯类杀虫剂
  • {uni_hamburg} no charge; orthoester; 1fragment

相关文献及参考

  • For further examples, see: Org. Synth. Coll., 6, 584 (1988); 7, 164 (1990).
  • Reaction with BF3 etherate gives the moderately stable selective alkylating agent, methyl diethoxycarbenium tetrafluoroborate: Synth. Commun., 19, 2307 (1989). Compare Triethyl­ orthoformate, A13587.
  • Reagent for facile esterification of sulfonic and carboxylic acids: Tetrahedron Lett., 34, 7355 (1993).
  • Short: EINECS
  • Short: III/35E
  • Short: III/38B
  • The products with allylic alcohols undergo Claisen allyl ether rearrangement, with addition of a 2-carbon unit and repositioning of the double bond: J. Am. Chem. Soc., 92, 741 (1970); Tetrahedron Lett., 21, 1285 (1980):
  • Under mild acid catalysis, reacts with ethynyl alcohols to give allenic esters, which can be conjugated over alumina. For examples, see: Org. Synth. Coll., 8, 251 (1993):

安全信息

Signal word Warning
GHS Symbol
WGK Germany1
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
  • R10 Flammable 易燃
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R36/38 Irritating to eyes and skin 对眼睛和皮肤有刺激性
Precautionary statements
  • P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking. 远离热源/火花/明火/热的表面。——禁止吸烟。
  • P233 Keep container tightly closed. ?保持容器密闭。
  • P240 Ground/bond container and receiving equipment. 与地面接触/连接集装箱和接受设备。
  • P241+P242+P243
  • 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+P352+P332+P313+P362+P364
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P332+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
  • P370+P378
  • P403+
  • P403+P235
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H226 Flammable liquid and vapour 易燃液体和蒸气
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
Personal Protective Equipment Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
Packing GroupIII
UN Number 3272
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 temperature {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
Hazard Codes 3
Hazard Class3

其他信息

  • 用途二:原乙酸三乙酯是合成二氯菊酸乙酯的重要中间体。
  • Sigma Aldrich:78-39-7(sigmaaldrich)
  • 海关编码:29159080
  • Alfa Aesar:原醋酸三乙酯,98% Triethyl orthoacetate, 98%(78-39-7)
  • 下游产品:氯菊酯 --> 1,2-苯二乙酸 --> 贲亭酸乙酯 --> 溴替唑仑 --> 4-氨基-6-甲基嘧啶-5-甲腈 --> 3.3-二甲基-4.6,6-三氯己烯[5]酸乙酯
  • 上游原料:氯化钠 --> 氯化铵 --> 4-氯苯甲醛 --> 乙酰胺 --> 指示剂 --> 乙醇钠乙醇溶液 --> 原乙酸三甲酯 --> 百里酚蓝
  • Acros Organics:原乙酸三乙酯 Triethyl orthoacetate, 97%(78-39-7)
  • 用途一:用于反式三取代烯及手性丙二烯等烯类制剂的制备及染料、制药工业的原料
  • 图谱信息:原乙酸三乙酯(78-39-7)红外图谱(IR1) 原乙酸三乙酯(78-39-7)红外图谱(IR2) 原乙酸三乙酯(78-39-7)质谱(MS) 原乙酸三乙酯(78-39-7)Raman光谱 原乙酸三乙酯(78-39-7)核磁图( 1 HNMR) 原乙酸三乙酯(78-39-7)核磁图( 13 CNMR)
  • MSDS 信息:Triethyl orthoacetate(78-39-7).msds
  • MOL 文件:78-39-7.mol
  • 原乙酸三乙酯价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 O0105 原乙酸三乙酯 Triethyl Orthoacetate 25ML 137元 2014/06/02 O0105 原乙酸三乙酯 Triethyl Orthoacetate 500ML 870元 2010/06/21 139651000 原乙酸三乙酯 Triethyl orthoacetate 97% 100 ML 357元
  • TCI Shanghai:原乙酸三乙酯 Triethyl Orthoacetate,>;95.0%(GC)(78-39-7)
  • 敏感性:Moisture Sensitive
  • 方法一:原乙酸三乙酯与原乙酸三甲酯的制法类似，将乙腈、甲苯和无水乙醇抽入到成盐锅，冷却到-10～-5℃，通入计量的干燥氯化氢，保持成盐温度-5～0℃，当氯化氢通完后，在0℃反应1h，然后在0～20℃保温0.5h，移至醇解锅，进行成盐反应，温度保持20～25℃，边搅拌边反应，约需12h，中间体亚氨基醚盐酸盐逐渐析出，冷却至0～5℃，再加入预冷的无水乙醇和麝香草酚蓝指示剂，加速搅拌，同时慢慢通入氨气至醇解物料中进行中和，观察指示剂颜色变化，直至由红转黄不再转红为止，pH＝3.6，此时通气结束，再在40℃进行醇解反应约8～9h，冷却物料，经离心机过滤除去氯化铵，滤液抽至中和锅内，加入17％乙醇钠乙醇溶液，调节溶液pH＝8～9，将此醇解物抽入蒸馏锅常压蒸馏，控制温度在75℃回收乙醇，将蒸余液冷却过滤除去乙酰胺、氯化钠固体，再用1％Na 2 CO 3 溶液洗涤，分层，油层进行减压蒸馏，先蒸出甲苯，再收集88～98℃/0.07MPa馏分即为原乙酸三乙酯。反应方程式：CH 3 CN+C 2 H 5 OH[HCl]→CH 3 C(OCH 5 ) 3 +NH 4 Cl

系列性分类

  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Oxygen Compounds 氧化合物
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Oxygen Compounds 氧化合物
  5. Acetals/Ketals/Ortho Esters - Oxygen Compounds
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Oxygen Compounds 氧化合物
  5. Acetals/Ketals/Ortho Esters - Oxygen Compounds
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Carbonyl Compounds 羰基化合物
  5. Esters - Carbonyl Compounds
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Chemicals by Class 化学分类法
  4. Orthoesters
  1. Functional Group 官能团索引
  2. orthocarboxylic acid derivative
  1. Functional Group 官能团索引
  2. orthoester