C88505
Cyanoacetic acid
99%
Synonym(s):
2-Cyanoacetic acid, Cyanoethanoic acid, Malonic mononitrile, Monocyanoacetic acid
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About This Item
Linear Formula:
NCCH2COOH
CAS Number:
Molecular Weight:
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
vapor pressure
0.1 mmHg ( 100 °C)
Quality Level
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
SMILES string
OC(=O)CC#N
InChI
1S/C3H3NO2/c4-2-1-3(5)6/h1H2,(H,5,6)
InChI key
MLIREBYILWEBDM-UHFFFAOYSA-N
Application
Cyanoacetic acid can be used as a reagent:
- Along with acetic anhydride for cyanoacetylation of various pyrroles, indoles, and aniline derivatives. It can also be used in other reactions such as cyclizations, syntheses of coumarins and other heterocycles.
- To prepare of key intermediate via Knoevenagel condensation in the total synthesis of 5-acetamido-substituted melatonin derivatives as MT3 receptor ligands.
- In the synthesis of aminopyrrolinone derivatives by reacting Ugi adducts of cyanoacetic acid and aromatic aldehydes.
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signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B
supp_hazards
Storage Class
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
Regulatory Information
危险化学品
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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)
Synthesis of novel ??3 receptor ligands via an unusual Knoevenagel condensation
Volkova MS, et al.
Bioorganic & medicinal chemistry letters, 22(24), 7578-7581 (2012)
Structure-toxicity relationships for methyl esters of cyanoacetic acids to Tetrahymena pyriformis.
M B Cottrell et al.
Bulletin of environmental contamination and toxicology, 70(3), 549-556 (2003-02-20)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| C88505-1KG | 04061833522875 |
| C88505-25G | 04061833522882 |
| C88505-500G | 04061833522899 |