693-51-6

Basic information

• Product Name: 3-(BUTYLAMINO)PROPIONITRILE
• Synonyms: 3-(BUTYLAMINO)PROPIONITRILE;3-(BUTYLAMINO)PROPANENITRILE;3-(N-BUTYLAMINO)PROPIONITRILE;LABOTEST-BB LTBB000460
• CAS NO: 693-51-6
• Molecular Formula: C₇H₁₄N₂
• Molecular Weight: 126.2
• Mol File: 693-51-6.mol

Chemical Properties

• Melting Point: 48.5-49.5 °C
• Boiling Point: 104-106°C 10mm
• Flash Point: 86.1 °C
• Appearance: /
• Density: 0,86 g/cm3
• Vapor Pressure: 0.123mmHg at 25°C
• Refractive Index: 1.432
• PKA: 8.70±0.19(Predicted)
• CAS DataBase Reference: 3-(BUTYLAMINO)PROPIONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(BUTYLAMINO)PROPIONITRILE(693-51-6)
• EPA Substance Registry System: 3-(BUTYLAMINO)PROPIONITRILE(693-51-6)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT, IRRITANT-HARMFUL
• Hazardous Substances Data: 693-51-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 1217, 1946 DOI: 10.1021/ja01211a023

InChI:InChI=1/C7H14N2/c1-2-3-6-9-7-4-5-8/h9H,2-4,6-7H2,1H3

Upstream product

• 542-76-7 3-Chloropropionitrile 
• 109-73-9 N-butylamine 
• 110-67-8 3-Methoxypropionitrile 
• 107-13-1 acrylonitrile 

Downstream Products

• 77390-89-7 acide (n-butylamino)-3 propanoique 
• 6935-60-0 N-(3-aminopropyl)butylamine 
• 22100-72-7 N-Trityl-N-<β-cyan-ethyl>-butylamin 
• 59049-47-7 N-(2-Benzoyl-4-nitro-phenyl)-2-[butyl-(2-cyano-ethyl)-amino]-N-methyl-acetamide 
• 688-23-3 N-Butyl-N-(2-cyan-ethyl)-harnstoff 
• 59049-46-6 N-(2-Benzoyl-4-chloro-phenyl)-2-[butyl-(2-cyano-ethyl)-amino]-N-methyl-acetamide 
• 59669-85-1 1-butyl-3-phenyl-2-thioxo-tetrahydro-pyrimidin-4-one 
• 98906-42-4 3-Benzoyl-1-butyl-1-(2-cyano-ethyl)-thiourea 
• 30381-06-7 N'-Phenyl-N-butyl-N-(2-cyanaethyl)thioharnstoff 

Relevant articles and documents

Ruthenium (II) β-diketimine as hydroamination catalyst, crystal structure and DFT computations

A new half-sandwich ruthenium (II) complex containing β-diketiminate ligand has been synthesized and used for hydroamination of acrylonitrile with aromatic and aliphatic amines. The catalytic activity of prepared complex was compared with a series of ruthenium complexes of β-diketiminate ligands, and the effect of electronic and steric properties of these ligands on catalytic activity of their complexes was investigated. Replacement of H atom in α position of β-diketiminate with (CF3) as an electron-withdrawing group leads to decreasing the reaction yield, and on the other hand, electron-donating group (CH3) has the opposite effect. In addition, crystal structure of [Ru(p-cymen)Cl(LH,Cl)] was determined by single X-ray crystallography. Hirshfeld surface analysis has been performed to determine the dominate interactions in molecular crystal. Furthermore, density functional, QTAIM and energy calculations have been carried out, to get the detailed insight into electronic and bonding characteristics of titled compound.

O-benzenedisulfonimide as a reusable brnsted acid catalyst for hetero-michael reactions

The hetero-Michael reactions among various oxygen, sulfur, and nitrogen nucleophiles and ,-unsaturated compounds were carried out in the presence of catalytic amounts of o-benzenedisulfonimide as Brnsted acid organocatalyst. The reaction conditions were very mild, and the yields of target products were good. The catalyst was easily recovered and purified, ready to be used in further reactions. This ability grants economic and ecological advantages. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

Ultrasound-assisted aza-Michael reaction in water: A green procedure

The conjugate addition of amines to conjugated alkenes (commonly known as aza-Michael reaction) constitutes a key step for the synthesis of various complex natural products, antibiotics, α-amino alcohols and chiral auxiliaries. Ultrasound-induced addition of several amines to α, β-unsaturated ketones, esters and nitriles has been carried out very efficiently in water as well as under solvent-free conditions. No catalysts or solid supports have been used in this method. Remarkable enhancement of reaction rate has been observed in water under ultrasound-induced method. This environmentally benign procedure has provided clean formation of the products with better selectivity.

An efficient biomaterial supported bifunctional organocatalyst (ES-SO 3- C5H5NH+) for the synthesis of β-amino carbonyls

A biomaterial supported organocatalyst, readily synthesized by the reaction of chemically modified sulfonic group containing expanded corn starch with pyridine exhibited excellent catalytic activity for the synthesis of β-amino carbonyls in excellent yields via aza-Michael addition of amines to electron deficient alkenes. A remarkable enhancement in the reaction rates was observed with the prepared bifunctional organocatalyst in comparison to the either starch grafted sulfonic acid or the corresponding homogeneous pyridinium p-toluenesulfonate.

Graphene oxide: An efficient and reusable carbocatalyst for aza-Michael addition of amines to activated alkenes

Graphene oxide was found to be a highly efficient, reusable and cost-effective organocatalyst for the aza-Michael addition of amines to activated alkenes to furnish corresponding β-amino compounds in excellent yields. The Royal Society of Chemistry 2011.

Cesium fluoride catalyzed Aza-Michael addition reaction in aqueous media

A green approach to the Aza-Michael addition reaction between an amine and α,β-unsaturated compounds has been achieved by conventional as well as non-conventional methods. The reaction is catalyzed by cesium fluoride (CsF) in aqueous media at ambient temperature to afford the product in excellent yield. Ultrasound irradiation has been used as a non-conventional energy source, which reduces the reaction time with improved product yield.

Solid sodium stannate as a high-efficiency superbase catalyst for anti-Markovnikov hydroamination and hydroalkoxylation of electron-deficient olefins under mild conditions

A solid superbase with H- above 26.5 has been obtained through thermal treatment of sodium stannate hydrate. It was found to be an efficient catalyst for anti-Markovnikov hydroamination and hydroalkoxylation of electron-deficient olefins under mild conditions.

Microwave-induced aza-michael reaction in water: A remarkably simple procedure

Microwave-induced fast addition of several amines to conjugated carbonyl compounds has been carried out in water very efficiently in the absence of any catalyst. Copyright

Aza-michael addition of amines to α,β-unsaturated compounds using molecular iodine as catalyst

Aza-Michael adducts are obtained in very good yields by the conjugate addition of aliphatic amines to α,β-unsaturated compounds using molecular iodine as catalyst in dichloromethane at room temperature. Aromatic amines were found to be reactive under reflux in toluene.

An effective aza-michael addition of aromatic amines to electron-deficient alkenes in alkaline Al2O3

Aza-Michael addition of aromatic or aliphatic amines with various electron-deficient alkenes was performed using alkaline Al2O 3 as solid media at room temperature afforded the corresponding Michael addition products in good to excellent yields.The alkaline Al 2O3 can be easily recovered and reused.