| Identification | More | [Name]
n-Butyl cyanoacetate | [CAS]
5459-58-5 | [Synonyms]
BCYA
BUTYL CYANOACETATE
BUTYL CYANOACETATE(N-)
CYANOACETIC ACID N-BUTYL ESTER
CYANOACETIC N-BUTYL ESTER
N-BUTYL CYANOACETATE
Acetic acid, cyano-, butyl ester
Aceticacid,cyano-,butylester
cyano-aceticacibutylester
n-Butyl cyanoacetate, 99+%
AButyl cyanoacetate
Butyl 2-cyanoacetate
n-Butyl a-cyanoacetate
2-Cyanoacetic acid butyl ester | [EINECS(EC#)]
226-730-1 | [Molecular Formula]
C7H11NO2 | [MDL Number]
MFCD00001941 | [Molecular Weight]
141.17 | [MOL File]
5459-58-5.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear liquid | [Boiling point ]
230.7 °C | [density ]
1 | [refractive index ]
n20/D 1.425(lit.)
| [Fp ]
189 °F
| [storage temp. ]
2-8°C | [form ]
clear liquid | [pka]
3.06±0.10(Predicted) | [color ]
APHA: ≤60 | [Water Solubility ]
IMMISCIBLE | [Usage]
Butyl cyanoacetate is used as intermediate for numerous organic syntheses, e.g. alpha-cyanoacrylic adhesives. Product Data Sheet | [InChI]
InChI=1S/C7H11NO2/c1-2-3-6-10-7(9)4-5-8/h2-4,6H2,1H3 | [InChIKey]
DJACTCNGCHPGOI-UHFFFAOYSA-N | [SMILES]
C(OCCCC)(=O)CC#N | [CAS DataBase Reference]
5459-58-5(CAS DataBase Reference) | [NIST Chemistry Reference]
n-Butyl cyanoacetate(5459-58-5) | [EPA Substance Registry System]
5459-58-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S27:Take off immediately all contaminated clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN 3276 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
AG3692500
| [TSCA ]
TSCA listed | [PackingGroup ]
III | [HS Code ]
29269090 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Clear liquid | [Uses]
Butyl cyanoacetate is used as intermediate for numerous organic syntheses, e.g. alpha-cyanoacrylic adhesives. Product Data Sheet | [General Description]
tert-Butyl cyanoacetate undergoes alkylation with many substituted benzyl and heteroalyl alcohols to form the corressponding alpha-alkylated products. | [Synthesis]
To a well-stirred mixture of cyano acid (80 mmol) in alcohol (90 mmol), and acetonitrile (162 mmol) , added sulfuric acid (98%, 94 mmol, 5 mL) at room temperature and temperature maintained between 80-85°C for 16-18h. The reaction mixture was cooled and added to 20% sodium carbonate solution (100 mL). The reaction mass was extracted in CH2Cl2 (50 mL × 2). The combined organic layer was washed with water (100 mL), dried over sodium sufate, and concentrated under reduced pressure to obtain n-Butyl cyanoacetate (85-95%). | [References]
[1] Synthetic Communications, 2014, vol. 44, # 6, p. 836 - 846
[2] Patent: US2553065, 1949,
[3] Patent: US6288264, 2001, B1
[4] Applied Organometallic Chemistry, 2018, vol. 32, # 3,
[5] Patent: WO2018/114457, 2018, A1. Location in patent: Paragraph 0046; 0047 |
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