Dimethyl malonate 丙二酸二甲酯

CAS 108-59-8 MFCD00008460

化学结构图

108-59-8
SMILES: COC(=O)CC(=O)OC

化学属性

Mol. FormulaC5H8O4
Mol. Weight132.11
Refractive index1.4120 to 1.4150
Boiling Point180-181 °C at 760 mmHg
Density1.156
Melting Point-62 °C
Flash Point91°C(lit.)
TSCAYes
Vapor Density>;1 (vs air)
Solubility溶于醇、醚等有机溶剂,微溶于水。
Stability对湿度敏感
Appearance 无色液体。 溶于醇、醚等有机溶剂,微溶于水。

别名和识别编码

Chemical NameDimethyl malonate
CAS Number108-59-8
PubChem Substance ID87572148
EC Number203-597-8
Beilstein Registry Number2,572
MDL NumberMFCD00008460
Reaxys-RN774261
Merck Number6096
Synonym Dimethyl malonate {LY} Dimethyl malonate {} {LY} Dimethyl malonate {} {} {LY} Dimethyl malonate {} {} {} {LY} Dimethyl malonate {} {} {} {} {LY} Dimethyl malonate {} {} {} {} {} {LY} Dimethyl malonate {} {} {} {} {} {} {LY} Dimethyl malonate {} {} {} {} {} {} {} {LY} Dimethyl malonate {} {} {} {} {} {} {} {} {LY} Dimethyl malonate {} {} {} {} {} {} {} {} {} {LY} Dimethyl malonate {} {} {} {} {} {} {} {} {} {} {LY} Dimethyl malonate {} {} {} {} {} {} {} {} {} {} {} {LY} Dimethyl malonate {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Dimethyl malonate {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Dimethyl malonate {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Dimethyl malonate {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Dimethyl malonate {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Dimethyl malonate {} {} {} {} {} {} {} {} {}
Chemical Name Translation丙二酸二甲酯
Wiswesser Line Notation1OV1VO1
LabNetwork Molecule IDLN00199486
Canonical SMILESO=C(OC)CC(OC)=O
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分类

  • {uni_hamburg} no charge; ester; 1fragment
  • Building Blocks, C2 to C5, Carbonyl Compounds, Chemical Synthesis, Esters, Organic Building Blocks
  • {SNA} Building Blocks, C2 to C5, Carbonyl Compounds, Chemical Synthesis, Esters, Organic Building Blocks

产品应用

  • 气相色谱对比样品,有机合成。

相关文献及参考

  • Merck:14,6096 Beilstein:2,572
  • C-Arylation with ortho-nitroaryl halides can be accomplished with NaH in DMSO. The products can be readily converted to substituted oxindoles: Synthesis, 51 (1993):
  • Short: II/27B
  • Arylation with benzene: Tetrahedron Lett., 27, 2763 (1986), and free-radical substitution with thiophene or furan at the 2-position: Heterocycles, 27, 2627 (1988), are promoted by Ce(IV) salts.
  • Merck:14,6096
  • For successive C-alkylation, using NaOMe/MeOH, followed by NaH/THF, see: Org. Synth. Coll., 8, 381 (1993). For Michael addition to ɑß-unsaturated acids, catalyzed by the Li salt of L-proline, see: J. Chem. Soc., Chem. Commun., 1088 (1991). For Knoevenagel reaction with (R)-citronellal, catalyzed by piperidine/AcOH, to give the alkylidene derivative, see: Org. Synth. Coll., 9, 310 (1998).
  • See also Diethyl­ malonate, A15468.

安全信息

GHS Symbol
WGK Germany1
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H227 Combustible liquid 可燃液体
Personal Protective Equipment Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
Hazard Codes Xi
RTECSOO0950000
Precautionary statements
  • 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。
  • 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
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P305+P351+P338
  • 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。
  • P302+P352+P332+P313+P362+P364
  • P305+P351+P338+P337+P313
  • P403+P235
Signal word
Safety Statements
  • S15 Keep away from heat 远离热源;
  • S36 Wear suitable protective clothing 穿戴适当的防护服;
  • 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;
  • 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;
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
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
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 5331 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   FCTXAV Food and Cosmetics Toxicology.  (London, UK)  V.1-19, 1963-81.  For
   publisher information, see FCTOD7.  Volume(issue)/page/year: 17,363,1979

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Administration onto the skin
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : >5 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   FCTXAV Food and Cosmetics Toxicology.  (London, UK)  V.1-19, 1963-81.  For
   publisher information, see FCTOD7.  Volume(issue)/page/year: 17,363,1979

其他信息

  • Alfa Aesar:丙二酸二甲酯,98+% Dimethyl malonate, 98+%(108-59-8)
  • 用途三:气相色谱对比样品,有机合成。
  • Acros Organics:丙二酸二甲酯 Dimethyl malonate, 97%(108-59-8)
  • 用途一:用于制药及有机合成
  • MSDS 信息:Methyl malonate(108-59-8).msds
  • 下游产品:1-氨基环丙甲醇 --> 甲氧基马来酸二甲酯 --> 氯嘧黄隆 --> 3-(4-氟苯基)丙酸 --> 丙烯草丁钠 --> 叔丁基甲基马来酸酯 --> 2-甲基嘧啶 --> 3-环戊烯-1-甲酸甲酯 --> 稀禾定 --> 甲基氟嘧磺隆 --> 5-[2-(乙硫基)丙基]-1,3-环己二酮 --> 6-氯氧化吲哚 --> 吡哌酸 --> 5-氟吲哚-2-酮 --> 溴丙二酸二甲酯 --> 7-羟基-2-氧代-2H-苯并吡喃-3-甲酸甲酯 --> 1,1-环丙烷二甲酸二甲酯 --> 6-氯-2-氧代-2H-苯并吡喃-3-羧酸 --> 丙二酸二丁酯 --> 乙基丙二酸二甲酯 --> 氯丙二酸二甲酯 --> 5-(2,4,6-三甲基苯基)-1,3-环己二酮 --> 5-(四氢-2H-噻烷-3-基)-1,3-环己二酮
  • Sigma Aldrich:108-59-8(sigmaaldrich)
  • 蒸气密度:>;1 (vs air)
  • TCI Shanghai:丙二酸二甲酯 Dimethyl Malonate,>;98.0%(GC)(108-59-8)
  • 方法一:多用氰化酯化法。氯乙酸与碳酸钠中和生成氯乙酸钠,再用氰化钠进行氰化得氰乙酸钠。氰乙酸钠水解成丙二酸钠,然后在硫酸存在下与甲醇酯化得丙二酸二甲酯,经洗涤、蒸馏即得成品。工业品含酯量≥98%。原料消耗定额:氯乙酸1120kg/t、氰化钠551kg/t、甲醇955kg/t。国外开发的新工艺主要以催化羰基化法为主,即以氯乙酸酯、一氧化碳、甲醇为原料,在催化剂存在下,一步反应合成丙二酸二甲酯。相比之下,催化羰基化法工艺技术先进,但工艺复杂,反应条件苛刻,工业化实现有一定的困难。
  • 丙二酸二甲酯价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 30069626 丙二酸二甲酯 100ml 99.1元 2011/04/16 M0030 丙二酸二甲酯 Dimethyl Malonate 25G 155元 2011/04/16 M0030 丙二酸二甲酯 Dimethyl Malonate 500G 360元
  • 海关编码:29171910
  • Hazard Note:Irritant
  • 上游原料:盐酸 --> 甲醇 --> 硫酸 --> 碳酸钠 --> 氰化钠 --> 氯乙酸 --> 氯乙酸钠 --> 氰乙酸 --> 丙二酸钠盐一水合
  • MOL 文件:108-59-8.mol
  • 图谱信息:丙二酸二甲酯(108-59-8)质谱(MS) 丙二酸二甲酯(108-59-8)红外图谱(IR1) 丙二酸二甲酯(108-59-8)核磁图( 1 HNMR) 丙二酸二甲酯(108-59-8)Raman光谱 丙二酸二甲酯(108-59-8)核磁图( 13 CNMR)
  • 易溶于醇、醚、丙酮、苯和油类,微溶于水。
  • Dimethyl Malonate is a diester derivative of Malonic Acid. It is also a precursor in the synthesis of Barbituric Acids.
  • 用途二:丙二酸二甲酯是生产医药吡哌酸的重要原料。国外丙二酸二甲酯主要用作非乙氧甲叉工艺生产吡哌酸的原料,与原甲酸酯和尿素反应生产吡哌酸。目前我国相关企业生产的丙二酸二甲酯除出口外,绝大部分用来生产吡哌酸。

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