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
产品名称
氰乙酸, 99%
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
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)
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
Tian-Yu Liu et al.
Organic & biomolecular chemistry, 4(11), 2097-2099 (2006-05-27)
The bifunctional thiourea-tertiary amine derivatives of simple chiral diamines serve as highly enantioselective catalysts for the Michael addition of alpha-substituted cyanoacetates to vinyl sulfones, giving an efficient protocol for the construction of an all-carbon substituted quaternary stereocentre.
Yijun Huang et al.
Molecular diversity, 15(1), 3-33 (2010-03-02)
The Gewald reaction of sulfur, cyanoacetic acid derivatives, and oxo-component (G-3CR) yielding highly substituted 2-aminothiophene derivatives has seen diverse applications in combinatorial and medicinal chemistry. Its products are of great use in pharmaceutical industry mainly as small molecular weight inhibitors.
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