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C88505 Sigma-Aldrich

Cyanoacetic acid

99%

  • CAS Number 372-09-8

  • Linear Formula NCCH2COOH

  • Molecular Weight 85.06

  •  Beilstein/REAXYS Number 506325

  •  EC Number 206-743-9

  •  MDL number MFCD00002677

  •  PubChem Substance ID 24893110

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, C1 to C5, Carbonyl Compounds, Carboxylic Acids, Chemical Synthesis,
vapor pressure   0.1 mmHg ( 100 °C)
assay   99%
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

Description

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.

Packaging

1 kg in glass bottle

25, 500 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Supplemental Hazard Statements 
Contact with acids liberates toxic gas.
RIDADR 
UN 3261 8 / PGII
WGK Germany 
1
RTECS 
AG3675000
Flash Point(F) 
224.6 °F
Flash Point(C) 
107 °C

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Meet Synthia - Retrosynthesis Sofware
Protocols & Articles
Peer-Reviewed Papers
15

References

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