Dimethyl Acetylenedicarboxylate(DMAD) 丁炔二酸二甲酯

CAS 762-42-5 MFCD00008456

化学结构图

762-42-5
SMILES: COC(=O)C#CC(=O)OC

化学属性

Mol. FormulaC6H6O4
Mol. Weight142.11
Refractive index1.4450 to 1.4490
Boiling Point204.3°C at 760 mmHg
Density1.156
Flash Point86°C
TSCAYes
Melting Point-18°C
Appearance 无色液体。沸点95-98℃（2.53kPa）。

别名和识别编码

Chemical NameDimethyl Acetylenedicarboxylate(DMAD)
Synonym 1,4-Dimethyl but-2-ynedioate {LY} 1,4-Dimethyl but-2-ynedioate {} {LY} 1,4-Dimethyl but-2-ynedioate {} {} {LY} 1,4-Dimethyl but-2-ynedioate {} {} {} {LY} 1,4-Dimethyl but-2-ynedioate {} {} {} {} {LY} 1,4-Dimethyl but-2-ynedioate {} {} {} {} {} {} {} {} {} {} {LY} 1,4-Dimethyl but-2-ynedioate {} {} {} {} {} {} {LY} 1,4-Dimethyl but-2-ynedioate {} {} {} {} {} {} {} {LY} 1,4-Dimethyl but-2-ynedioate {} {} {} {} {} {} {} {} {LY} 1,4-Dimethyl but-2-ynedioate {} {} {} {} {} {} {} {} {} {LY} 1,4-Dimethyl but-2-ynedioate {} {} {} {} {} {} {} {} {} {} {LY} 1,4-Dimethyl but-2-ynedioate {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 1,4-Dimethyl but-2-ynedioate {} {} {} {} {} {} {} {} {} {} {} {} {LY} 1,4-Dimethyl but-2-ynedioate {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 1,4-Dimethyl but-2-ynedioate {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 1,4-Dimethyl but-2-ynedioate {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 1,4-Dimethyl but-2-yned
CAS Number762-42-5
PubChem Substance ID87561787
EC Number212-098-4
Beilstein Registry Number607063
MDL NumberMFCD00008456
Chemical Name Translation丁炔二酸二甲酯
Reaxys-RN607063
Wiswesser Line Notation1OV1UU1VO1
LabNetwork Molecule IDLN00009149
InChIInChI=1S/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3
Canonical SMILESO=C(C#CC(OC)=O)OC
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分类

  • {SNA} Building Blocks, C6 to C7, Carbonyl Compounds, Chemical Synthesis, Esters, Organic Building Blocks
  • Building Blocks, C6 to C7, Carbonyl Compounds, Chemical Synthesis, Esters, Organic Building Blocks

产品应用

  • 用于有机合成。

相关文献及参考

  • Reacts with activated carbonyl compounds, such as ɑ-keto esters or ɑ-keto nitriles, in the presence of triphenylphosphine, to give highly functionalized -butyrolactones: J. Org. Chem., 61, 4516 (1996). For a further example with reaction scheme, see 2,2,2-Trifluoroacetophenone,
  • Stabilized anions derived from cyclic ß-keto phosphonates undergo ring expansion, via a tandem Michael-Aldol-fragmentation mechanism, to give phosphonates with an additional two carbons in the ring, thus providing a route to highly functionalized medium ring compounds: J. Org. Chem., 60, 3084 (1995):
  • Beilstein:2,803
  • Reacts with activated carbonyl compounds, such as ɑ-keto esters or ɑ-keto nitriles, in the presence of triphenylphosphine, to give highly functionalized -butyrolactones: J. Org. Chem., 61, 4516 (1996). For a further example with reaction scheme, see 2,2,2-Trifluoroacetophenone, A11403.
  • For use in the masking of double bonds for subsequent release by cycloreversion, see: J. Org. Chem., 44, 962 (1979). Review of cycloreversion reactions in organic synthesis: Synthesis, 121 (1985).
  • Dienophile in Diels-Alder and related reactions. For addition to a bis-allene, followed by dimerization to a paracyclophane, see: Org. Synth. Coll., 7, 485 (1990).
  • Used in synthesis of a wide variety of heterocyclic systems including benzo[b]thiophenes from thiophenols: Acta Chem. Scand., 27, 595 (1973), and chromones from phenols: Austral. J. Chem., 48, 677 (1995):

安全信息

GHS Symbol
WGK Germany3
Hazard statements
  • H227 Combustible liquid 可燃液体
  • H302 Harmful if swallowed 吞食有害
  • H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
Personal Protective Equipment Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
Hazard Codes 8 C
RTECSES0175000
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。
  • 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。
  • 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。
  • 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
  • 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。
  • P403+P235
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Signal word Danger
Packing GroupII
UN Number 1760 3265
Risk Statements
  • R34 Causes burns 会导致灼伤
Safety Statements
  • S23 Do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer) 不要吸入气体/烟雾/蒸汽/喷雾；
  • 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；
  • 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）；
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 Class8 
TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 50 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NCNSA6 National Academy of Sciences, National Research Council,
   Chemical-Biological Coordination Center, Review.  (Washington, DC)
   Volume(issue)/page/year: 5,13,1953

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 550 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Behavioral - ataxia
   Behavioral - coma
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: 28(6),55,1984

其他信息

  • Sigma Aldrich:762-42-5(sigmaaldrich)
  • 用途一:用于有机合成。
  • Acros Organics:丁炔二酸二甲酯 Dimethyl acetylenedicarboxylate, 98%(762-42-5)
  • F:8-19
  • MOL 文件:762-42-5.mol
  • 下游产品:尼多克罗 --> 2,3-喹啉二甲酸
  • 上游原料:酞酸二甲酯 --> 二甲酸钾
  • MSDS 信息:Acetylenedicarboxylic acid dimethyl ester(762-42-5).msds
  • 丁炔二酸二甲酯价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 A0090 乙炔二羧酸二甲酯 Dimethyl Acetylenedicarboxylate 25ML 462元 2014/06/02 A0090 乙炔二羧酸二甲酯 Dimethyl Acetylenedicarboxylate 500ML 4600元 2010/06/21 115710250 丁炔二酸二甲酯 Dimethyl acetylenedicarboxylate 98% 25 GR 777元
  • Alfa Aesar:丁炔二羧酸二甲酯,98% Dimethyl acetylenedicarboxylate, 98%(762-42-5)
  • 丁炔二酸二甲酯价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/04/16 A0090 乙炔二羧酸二甲酯 Dimethyl Acetylenedicarboxylate 25ML 695元 2011/04/16 A0090 乙炔二羧酸二甲酯 Dimethyl Acetylenedicarboxylate 500ML 7130元 2010/06/21 115710250 丁炔二酸二甲酯 Dimethyl acetylenedicarboxylate 98% 25 GR 777元
  • 海关编码:29171990
  • 检测方法:GC,NMR
  • TCI Shanghai:丁炔二酸二甲酯 Dimethyl Acetylenedicarboxylate,>;96.0%(GC)(762-42-5)
  • 方法一:丁炔二甲酸钾与甲醇在浓硫酸存在下室温反应4d，以72-88%的收率生成丁炔二酸二甲酯。
  • 敏感性:Light Sensitive

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. 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. Organic Building Blocks 有机砌块
  4. Carbonyl Compounds 羰基化合物
  5. Esters - Carbonyl Compounds
  6. C6 to C7 - Esters
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Chemicals by Class 化学分类法
  4. Acetylenes 炔烃
  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
  6. C2 to C5

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