C88505
氰乙酸
99%
别名:
2-氰基乙酸, 单氰基乙酸, 氰基乙酸
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线性分子式:
NCCH2COOH
化学文摘社编号:
分子量:
85.06
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
206-743-9
Beilstein/REAXYS Number:
506325
MDL number:
Assay:
99%
Form:
crystals
InChI key
MLIREBYILWEBDM-UHFFFAOYSA-N
InChI
1S/C3H3NO2/c4-2-1-3(5)6/h1H2,(H,5,6)
SMILES string
OC(=O)CC#N
vapor pressure
0.1 mmHg ( 100 °C)
assay
99%
form
crystals
bp
108 °C/0.15 mmHg (lit.)
mp
64-70 °C (lit.)
solubility
H2O: 50 mg/mL, clear, colorless to very faintly yellow
Quality Level
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Application
氰基乙酸可用作以下反应的试剂：
- 与乙酸酐一起用于各种吡咯、吲哚和苯胺衍生物的氰基乙酰化（cyanoacetylation）。它也可用于环化、香豆素和其他杂环的合成等其他反应中 。通过Knoevenagel缩合反应制备可作为MT3受体配体的5-乙酰氨基取代褪黑素衍生物的全合成过程的关键中间体。
- 通过Ugi加成物与氰基乙酸和芳香醛反应合成氨基吡咯啉酮（aminopyrrolinone ）衍生物。
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B
supp_hazards
存储类别
8A - Combustible corrosive hazardous materials
wgk
WGK 1
flash_point_f
224.6 °F - closed cup
flash_point_c
107 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
法规信息
危险化学品
此项目有
The Ugi Reaction of Cyanoacetic Acid as a Route to Tetramic Acid Derivatives
Alvarez-Rodriguez NV, et al.
Synlett, 26(16), 2253-2256 (2015)
Synthesis of novel ??3 receptor ligands via an unusual Knoevenagel condensation
Volkova MS, et al.
Bioorganic & medicinal chemistry letters, 22(24), 7578-7581 (2012)
Cyanoacetylation of indoles, pyrroles and aromatic amines with the combination cyanoacetic acid and acetic anhydride
Slaett J, et al.
Synthesis, 2004(16), 2760-2765 (2004)
Isocyanoacetate derivatives: synthesis, reactivity, and application.
Anton V Gulevich et al.
Chemical reviews, 110(9), 5235-5331 (2010-07-09)
S Kotha et al.
Amino acids, 32(3), 387-394 (2006-10-13)
Two synthetic routes to bis-armed-alpha-amino acid derivatives are described. The first route involves alkylation of dibromo derivatives with ethyl isocyanoacetate under phase-transfer catalysis (PTC) conditions. The second route uses a palladium-mediated Suzuki-Miyaura cross-coupling reaction between a DL-4-boronophenylalanine derivative and aromatic
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