20651-73-4

Basic information

• Product Name: 4-BUTYLBENZONITRILE
• Synonyms: 4-BUTYLBENZONITRILE;4-N-BUTYLBENZONITRILE;P-BUTYLBENZONITRILE;1-Butyl-4-cyanobenzene;Benzonitrile,4-butyl-;4-Butylbenzonitrile,98%;4-N-BUTYLBENZONITRILE 98%;4-n-Butylbenzonitrile,98%
• CAS NO: 20651-73-4
• Molecular Formula: C₁₁H₁₃N
• Molecular Weight: 159.23
• Product Categories: Aromatic Nitriles;C10 to C27;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 20651-73-4.mol

Chemical Properties

• Boiling Point: 132-133 °C12 mm Hg(lit.)
• Flash Point: 145 °F
• Appearance: clear colorless liquid
• Density: 0.924 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0114mmHg at 25°C
• Refractive Index: n20/D 1.515(lit.)
• CAS DataBase Reference: 4-BUTYLBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BUTYLBENZONITRILE(20651-73-4)
• EPA Substance Registry System: 4-BUTYLBENZONITRILE(20651-73-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• RIDADR: 3276
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 20651-73-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis Industry:
4-Butylbenzonitrile is used as a chemical intermediate for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals. Its unique structure allows it to be a versatile building block in the development of new molecules with potential applications in various fields.
Used in Flavor and Fragrance Industry:
4-Butylbenzonitrile is used as a flavoring agent and a fragrance ingredient in the food, beverage, and cosmetics industries. Its distinct aroma profile contributes to the creation of unique and appealing scents in various consumer products.
Used in Polymer Industry:
4-Butylbenzonitrile is used as a monomer in the production of polymers and copolymers. Its incorporation into polymer chains can enhance the material's properties, such as thermal stability, mechanical strength, and chemical resistance, making it suitable for various applications, including coatings, adhesives, and plastics.
Used in Dye and Pigment Industry:
4-Butylbenzonitrile is used as a precursor in the synthesis of dyes and pigments. Its ability to form stable chromophores makes it a valuable component in the development of colorants for textiles, paints, and inks.

InChI:InChI=1/C11H13N/c1-2-3-4-10-5-7-11(9-12)8-6-10/h5-8H,2-4H2,1H3

Upstream product

• 623-26-7 terephthalonitrile 
• 994-79-6 tetrabutylsilane 
• 1461-25-2 tetra-n-butyltin(IV) 
• 1067-42-1 tetrabutylgermanium 
• 109-65-9 1-bromo-butane 
• 6638-68-2 4,5-dimethyl-2-phenyl-1,3,2-dioxaborolane 
• 138373-10-1 4-cyanophenyl mesylate 
• 41492-05-1 p-bromobutylbenzene 
• 557-21-1 dicyanozinc 
• 77153-60-7 1-(4-Butylphenyl)-3,3-(1,5-pentanediyl)triazene 
• 109-72-8 n-butyllithium 
• 623-03-0 4-Cyanochlorobenzene 
• 4426-47-5 butylboronic acid 
• 623-00-7 4-bromobenzenecarbonitrile 

Downstream Products

• 20651-71-2 4-butyl benzoic acid 
• 29147-98-6 4-n-butylbenzamidine hydrochloride 
• 35684-23-2 4-Methoxyphenyl-4'-n-butylbenzoat 
• 38454-43-2 4-Butyl-benzoic acid 4-butyl-phenyl ester 
• 38454-20-5 4-Butyl-benzoic acid 4-butoxy-phenyl ester 
• 38444-22-3 4'-heptylphenyl-4-butylbenzoate 
• 38580-63-1 4-Butyl-benzoic acid 4-octyl-phenyl ester 
• 38444-36-9 4-Butyl-benzoic acid 4-nonyl-phenyl ester 
• 38454-35-2 4-Butyl-benzoic acid 4-heptyloxy-phenyl ester 
• 38444-12-1 4-Butyl-benzoic acid 4-pentyl-phenyl ester 
• 38454-28-3 4-n-hexyloxyphenyl 4-n-butylbenzoate 
• 1092473-70-5 C₂₆H₃₂N₂O₃ 
• 1225289-65-5 C₁₉H₂₀F₃NO 
• 1225289-46-2 C₂₈H₂₂F₆O₂ 

Relevant articles and documents

Nickel-Catalyzed Cyanation of Aryl Thioethers

A nickel-catalyzed cyanation of aryl thioethers using Zn(CN)2 as a cyanide source has been developed to access functionalized aryl nitriles. The ligand dcype (1,2-bis(dicyclohexylphosphino)ethane) in combination with the base KOAc (potassium acetate) is essential for achieving this transformation efficiently. This reaction involves both a C-S bond activation and a C-C bond formation. The scalability, low catalyst and reagents loadings, and high functional group tolerance have enabled both late-stage derivatization and polymer recycling, demonstrating the reaction's utility across organic chemistry.

Scalable Negishi Coupling between Organozinc Compounds and (Hetero)Aryl Bromides under Aerobic Conditions when using Bulk Water or Deep Eutectic Solvents with no Additional Ligands

Pd-catalyzed Negishi cross-coupling reactions between organozinc compounds and (hetero)aryl bromides have been reported when using bulk water as the reaction medium in the presence of NaCl or the biodegradable choline chloride/urea eutectic mixture. Both C(sp3)-C(sp2) and C(sp2)-C(sp2) couplings have been found to proceed smoothly, with high chemoselectivity, under mild conditions (room temperature or 60 °C) in air, and in competition with protonolysis. Additional benefits include very short reaction times (20 s), good to excellent yields (up to 98 %), wide substrate scope, and the tolerance of a variety of functional groups. The proposed novel protocol is scalable, and the practicability of the method is further highlighted by an easy recycling of both the catalyst and the eutectic mixture or water.

A Ball-Milling-Enabled Cross-Electrophile Coupling

The nickel-catalyzed cross-electrophile coupling of aryl halides and alkyl halides enabled by ball-milling is herein described. Under a mechanochemical manifold, the reductive C-C bond formation was achieved in the absence of bulk solvent and air/moisture sensitive setups, in reaction times of 2 h. The mechanical action provided by ball milling permits the use of a range of zinc sources to turnover the nickel catalytic cycle, enabling the synthesis of 28 cross-electrophile coupled products.

Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers

We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications demonstrate its versatility and utility in multistep synthesis.

Reductive cyanation of organic chlorides using CO2 and NH3 via Triphos–Ni(I) species

Cyano-containing compounds constitute important pharmaceuticals, agrochemicals and organic materials. Traditional cyanation methods often rely on the use of toxic metal cyanides which have serious disposal, storage and transportation issues. Therefore, there is an increasing need to develop general and efficient catalytic methods for cyanide-free production of nitriles. Here we report the reductive cyanation of organic chlorides using CO2/NH3 as the electrophilic CN source. The use of tridentate phosphine ligand Triphos allows for the nickel-catalyzed cyanation of a broad array of aryl and aliphatic chlorides to produce the desired nitrile products in good yields, and with excellent functional group tolerance. Cheap and bench-stable urea was also shown as suitable CN source, suggesting promising application potential. Mechanistic studies imply that Triphos-Ni(I) species are responsible for the reductive C-C coupling approach involving isocyanate intermediates. This method expands the application potential of reductive cyanation in the synthesis of functionalized nitrile compounds under cyanide-free conditions, which is valuable for safe synthesis of (isotope-labeled) drugs.

Gram-Scale, Cheap, and Eco-Friendly Iron-Catalyzed Cross-Coupling between Alkyl Grignard Reagents and Alkenyl or Aryl Halides

A new robust methodology for gram-scale iron-catalyzed cross-coupling between alkyl Grignard reagents and alkenyl or aryl halides is developed. This method does not require toxic additives such as NMP or expensive ligands. Its efficiency relies on the use of simple alkoxide magnesium salts as additives. On the basis of these results, a new procedure for one-pot synthesis of substituted benzamides from chloroesters is also proposed.

Preparing method of aromatic nitrile or alkenyl nitrile compound

The invention discloses a preparing method of an aromatic nitrile or alkenyl nitrile compound. The preparing method comprises the following step that under protection of inert gas, an aryl or heteroaryl sulphonate compound shown in a formula II or an alkenyl sulphonate compound shown in a formula IV and a cyanation reagent are subjected to a cross-coupling reaction as is shown below in a solvent under the condition of the presence of a nickel complex, metal zinc and an additive to obtain the aromatic nitrile or alkenyl nitrile compound, wherein 4-dimethylamiopryidine (DMAP) is adopted as the additive, and zinc cyanide is adopted as the cyanation reagent. By means of the preparing method, cyanation of aryl sulphonate, heteroaryl sulphonate or alkenyl sulphonate can be simply and efficientlyachieved with a cheap catalysis system; moreover, the functional group compatibility and substrate universality are good, and a better application prospect and higher using value are provided for achieving industrial synthesis of the aromatic nitrile or alkenyl nitrile compound.

Nickel-Catalyzed Decarbonylative Cyanation of Acyl Chlorides

Ni-catalyzed decarbonylative cyanation of acyl chlorides with trimethylsilyl cyanide has been achieved. This transformation is applicable to the synthesis of an array of nitrile compounds bearing a wide range of functional groups under neutral conditions. The step-by-step experimental studies revealed that the reaction sequences of the present catalytic reaction are oxidative addition, transmetalation, decarbonylation, and reductive elimination.

Nickel-catalyzed cyanation of aryl halides and triflates using acetonitrile: Via C-CN bond cleavage assisted by 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine

We developed a non-toxic cyanation reaction of various aryl halides and triflates in acetonitrile using a catalyst system of [Ni(MeCN)6](BF4)2, 1,10-phenanthroline, and 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine (Si-Me4-DHP). Si-Me4-DHP was found to function as a reductant for generating nickel(0) species and a silylation reagent to achieve the catalytic cyanation via C-CN bond cleavage.

Nickel-Catalyzed Cyanation of Phenol Derivatives with Zn(CN)2 Involving C-O Bond Cleavage

An efficient nickel-catalyzed cyanation of aryl sulfonates, fluorosulfonates, and sulfamates with Zn(CN)2 was developed, which provides a facile access to the nitrile products in generally good to excellent yields. The reaction is accomplished by using NiII complex as the precatalyst and DMAP as the additive. The method also displays wide functional group compatibility; for example, keto, methoxy, N,N-dimethylamino, cyano, ester, and pyridyl groups are well-tolerated during the reaction process.