52493-37-5

Basic information

• Product Name: 2-CYANO-N-HEXYLACETAMIDE
• Synonyms: Albb-005846;2-cyano-N-hexyl-ethanamide
• CAS NO: 52493-37-5
• Molecular Formula: C₉H₁₆N₂O
• Molecular Weight: 168.24
• Mol File: 52493-37-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 346.4°Cat760mmHg
• Flash Point: 163.3°C
• Appearance: /
• Density: 0.953g/cm³
• Vapor Pressure: 5.78E-05mmHg at 25°C
• Refractive Index: 1.448
• CAS DataBase Reference: 2-CYANO-N-HEXYLACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CYANO-N-HEXYLACETAMIDE(52493-37-5)
• EPA Substance Registry System: 2-CYANO-N-HEXYLACETAMIDE(52493-37-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 52493-37-5(Hazardous Substances Data)

Usage

General Description

2-CYANO-N-HEXYLACETAMIDE is a chemical compound with the molecular formula C10H18N2O. It is a derivative of acetamide and is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. 2-CYANO-N-HEXYLACETAMIDE is a white crystalline solid that is soluble in organic solvents such as acetone and ethyl acetate. It is also known to be a potential irritant to the skin and eyes and may cause allergic reactions in some individuals. 2-CYANO-N-HEXYLACETAMIDE is used in various industries for its ability to act as a building block for the creation of other chemical compounds.

InChI:InChI=1/C9H16N2O/c1-2-3-4-5-8-11-9(12)6-7-10/h2-6,8H2,1H3,(H,11,12)

Upstream product

• 111-26-2 hexan-1-amine 
• 105-34-0 methyl 2-cyanoacetate 
• 105-56-6 ethyl 2-cyanoacetate 
• 107-91-5 cyanoacetic acid amide 

Relevant articles and documents

Discovery of acrylonitrile-based small molecules active against Haemonchus contortus

We report the discovery of a series of acrylonitrile-containing molecules and α-amino amides which cause 99-100% lethality in H. contortus. Of the 22 acrylonitrile analogues investigated, the most active were 2-cyano-3-[1-(3-dimethylaminopropyl)-2-methyl-

Small molecule inhibitors of dynamin I GTPase activity: Development of dimeric tyrphostins

Dynamin I is a GTPase enzyme required for endocytosis and is an excellent target for the design of potential endocytosis inhibitors. Screening of a library of tyrphostins, in our laboratory, against the GTPase activity of dynamin I gave rise to a ìèpotent lead, 2-cyano-3-(3,4- dihydroxyphenyl)thioacrylamide (1, IC50 70 μM). Our initial investigations suggested that only the dimeric form of 1 displayed dynamin I GTPase inhibitory activity. Subsequent synthetic iterations were based on dimeric analogues and afforded a number of small molecules, low μM potent, inhibitors of dynamin I GTPase, in particular, symmetrical analogues with a minimum of two free phenolic -OHs: catechol-acrylamide (9) (IC50 = 5.1 ± 0.6 μM), its 3,4,5-trihydroxy congener (10) (IC50 = 1.7 ± 0.2 μM), and the corresponding 3-methyl ether (11) (IC 50 = 9 ± 3 μM). Increasing the length of the central alkyl spacer from ethyl to propyl (22-24) afforded essentially identical activity with IC50's of 1.7 ± 0.2, 1.7 ± 0.2, and 5 ± 1 μM, respectively. No decrease in activity was noted until the introduction of a hexyl spacer. Our studies highlight the requirement for two free amido NHs with neither the mono-N-methyl (86) nor the bis-N-methyl (87) analogues inhibiting dynamin I GTPase. A similar effect was noted for the removal of the nitrile moieties. However, modest potency was observed with the corresponding ester analogues of 9-11: ethyl ester (90), propyl ester (91), and butyl ester (92), with IC50's of 42 ± 3, 38 ± 2, and 61 ± 2 μM, respectively. Our studies reveal the most potent and promising dynamin I GTPase inhibitor in this series as (22), which is also known as BisT.

Dimerization of merocyanine dyes. Structural and energetic characterization of dipolar dye aggregates and implications for nonlinear optical materials

Aggregation of polar merocyanine dyes has been identified as an important problem in the fabrication of organic materials for photonic applications. In this work, a series of merocyanine dyes is synthesized, and their aggregation is investigated by a combination of several experimental techniques to reveal structure-property relationships. These studies provide clear evidence for the formation of centrosymmetric dimers for all investigated merocyanines in concentrated solution and in the solid state. The thermodynamics of dimerization in liquid solution is studied by concentration-dependent permittivity measurements, UV-vis spectroscopy, and electrooptical absorption experiments. A centrosymmetric dimer structure with antiparallel ordering of the dipole moments is observed in solution by 2D NMR spectroscopy as well as in the solid state by x-ray crystallography and interpreted in terms of dipolar and π-π interactions. The optical properties of the dimer aggregates are satisfactorily explained by an excitonic coupling model. The effect of an external electric field on the dimerization equilibrium is considered and quantitatively determined by electrooptical absorption measurements. Implications of the observed findings on the design of nonlinear optical and photorefractive materials are discussed.