621-50-1

Basic information

• Product Name: 3-NITROPHENYLACETONITRILE
• Synonyms: m-nitrobenzylcyanide;m-Nitro-phenylacetonitrile;3-NITROPHENYLACETONITRILE;3-Nitrophenylaceonitrile;2-(3-nitrophenyl)ethanenitrile;NSC 91037;3-Nitrophenylacetonitrile 99%;(m-nitrophenyl)-acetonitril
• CAS NO: 621-50-1
• Molecular Formula: C₈H₆N₂O₂
• Molecular Weight: 162.15
• EINECS: 210-689-1
• Product Categories: Aromatics Compounds;Aromatics;C8 to C9;Cyanides/Nitriles;Nitrogen Compounds;Building Blocks;C8 to C9;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 621-50-1.mol

Chemical Properties

• Melting Point: 60-62 °C(lit.)
• Boiling Point: 180 °C3 mm Hg(lit.)
• Flash Point: 155°C
• Appearance: /
• Density: 1.3264 (rough estimate)
• Vapor Pressure: 0.000144mmHg at 25°C
• Refractive Index: 1.5770 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform, Ethyl Acetate
• CAS DataBase Reference: 3-NITROPHENYLACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-NITROPHENYLACETONITRILE(621-50-1)
• EPA Substance Registry System: 3-NITROPHENYLACETONITRILE(621-50-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22
• Safety Statements: 36
• WGK Germany: 3
• RTECS: AM1247000
• HazardClass: IRRITANT-HARMFUL
• Hazardous Substances Data: 621-50-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-Nitrophenylacetonitrile is used as a building block in the field of organic synthesis for its ability to react with different alcohols at high temperatures. This characteristic makes it a valuable compound in creating a wide range of chemical products and intermediates.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Nitrophenylacetonitrile is used as a key intermediate in the synthesis of various drugs and drug candidates. Its reactivity with alcohols allows for the creation of diverse molecular structures, which can be further modified to develop new medications with specific therapeutic properties.
Used in Chemical Research:
3-Nitrophenylacetonitrile is also utilized in chemical research as a model compound to study various reaction mechanisms and to develop new synthetic methods. Its unique properties and reactivity make it an ideal candidate for exploring novel chemical transformations and understanding the underlying principles of organic chemistry.

InChI:InChI=1/C8H6N2O2/c9-5-4-7-2-1-3-8(6-7)10(11)12/h1-3,6H,4H2

Upstream product

• 140-29-4 phenylacetonitrile 
• 64-17-5 ethanol 
• 151-50-8 potassium cyanide 
• 619-23-8 3-Nitrobenzyl chloride 
• 7697-37-2 nitric acid 
• 3958-57-4 1-bromomethyl-3-nitrobenzene 
• 619-25-0 3-Nitrobenzyl alcohol 
• 5247-25-6 2-(3-nitrophenyl)acetic acid amide 
• 143-33-9 sodium cyanide 
• 1058649-37-8 3-nitro-1-[(ethoxymethoxy)methyl]benzene 
• 10442-39-4 tetra-n-butylammonium cyanide 
• 142509-31-7 1-((methoxymethoxy)methyl)-3-nitrobenzene 
• 121-73-3 3-Nitrochlorobenzene 
• 1071-36-9 sodium cyanoacetate 

Downstream Products

• 876487-63-7 2,4,6-trihydroxy-3'-nitro-deoxybenzoin 
• 1877-73-2 3-nitro-benzeneacetic acid 
• 14318-64-0 ethyl (3-nitrophenyI)acetate 
• 4623-24-9 2-(3-aminophenyl)acetonitrile 
• 114166-31-3 2-(3-nitro-phenyl)-acetimidic acid ethyl ester; hydrochloride 
• 54648-43-0 2-(3-nitro-phenyl)-3c-phenyl-acrylonitrile 
• 99726-62-2 (m-nitrophenyl)malonitrile 
• 618-95-1 methyl 3-nitrobenzoate 
• 59265-70-2 propyl 3-nitrobenzoate 
• 618-98-4 ethyl 3-nitrobenzoate 
• 6268-23-1 isopropyl 3-nitrobenzoate 
• 136322-11-7 3-nitrobenzoic acid benzyl ester 
• 76935-75-6 2-(3-aminophenyl)ethylamine 
• 180079-94-1 N-(3-aminophenylmethyl)methylcarbamic acid t-butyl ester 

Relevant articles and documents

Rapid and Simple Access to α-(Hetero)arylacetonitriles from Gem-Difluoroalkenes

A scalable cyanation of gem-difluoroalkenes to (hetero)arylacetonitrile derivatives was developed. This strategy features mild reaction conditions, excellent yields, wide substrate scope, and broad functional group tolerance. Significantly, in this reacti

Two-step cyanomethylation protocol: Convenient access to functionalized aryl- and heteroarylacetonitriles

A two-step protocol has been developed for the introduction of cyanomethylene groups to metalated aromatics through the intermediacy of substituted isoxazoles. A palladium-mediated cross-coupling reaction was used to introduce the isoxazole unit, followed by release of the cyanomethylene function under thermal or microwave-assisted conditions. The intermediate isoxazoles were shown to be amenable to further functionalization prior to deprotection of the sensitive cyanomethylene motif, allowing access to a wide range of aryl- and heteroaryl-substituted acetonitrile building blocks.

JAK2 AND ALK2 INHIBITORS AND METHODS FOR THEIR USE

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Ionic liquid-induced conversion of methoxymethyl-protected alcohols into nitriles and iodides using [Hmim][NO3]

This Letter reports a one-pot efficient conversion of methoxymethyl-ethers into their corresponding nitriles and iodides using the ionic liquid, 1-methyl-3H-imidazolium nitrate ([Hmim][NO3]) under microwave irradiation. A variety of products were prepared in high yields using this method.

Caged CO2 for the Direct Observation of CO2-Consuming Reactions

CO2-consuming reactions, in particular carboxylations, play important roles in technical processes and in nature. Their kinetic behavior and the reaction mechanisms of carboxylating enzymes are difficult to study because CO2 is inconvenient to handle as a gas, exists in equilibrium with bicarbonate in aqueous solution, and typically yields products that show no significant spectroscopic differences from the reactants in the UV/Vis range. Here we demonstrate the utility of 3-nitrophenylacetic acid and related compounds (caged CO2) in conjunction with infrared spectroscopy as widely applicable tools for the investigation of such reactions, permitting convenient measurement of the kinetics of CO2 consumption. The use of isotopically labeled caged CO2 provides a tool for the assignment of infrared absorption bands, thus aiding insight into reaction intermediates and mechanisms.

Synthesis of α-Aryl nitriles through palladium-catalyzed decarboxylative coupling of cyanoacetate salts with aryl halides and triflates

Worth its salt: The palladium-catalyzed decarboxylative coupling of the cyanoacetate salt as well as its mono- and disubstituted derivatives with aryl chlorides, bromides, and triflates is described (see scheme). This reaction is potentially useful for the preparation of a diverse array of α-aryl nitriles and has good functional group tolerance. S-Phos=2-(2,6- dimethoxybiphenyl)dicyclohexylphosphine), Xant-Phos=4,5-bis(diphenylphosphino)- 9,9-dimethylxanthene. Copyright

Discovery of substituted phenyl urea derivatives as novel long-acting β2-adrenoreceptor agonists

The synthesis of diverse functionalized ureas in a semi-parallel fashion is described, as well as their β1/β2-adrenergic activities and the corresponding structure-activity relationship (SAR). We have focused on lipophilicity and duration of action, and we have discovered a strong correlation in this series of molecules. A quantitative structure-activity relationship (QSAR) analysis will be presented that quantifies this relationship.

Ethylammonium nitrate (EAN)/Tf2O and EAN/TFAA: Ionic liquid based systems for aromatic nitration

Acting as in situ sources of triflyl nitrate (TfONO2) and trifluoroacetyl nitrate (CF3COONO2), the EAN/Tf 2O and EAN/TFAA systems, generated via metathesis in the readily available ethylammonium nitrate (EAN) ionic liquid as solvent, are powerful electrophilic nitrating reagents for a wide variety of aromatic and heteroaromatic compounds. Comparative nitration experiments indicate that EAN/Tf2O is superior to EAN/TFAA for nitration of strongly deactivated systems. Both systems exhibit low substrate selectivity (K T/KB = 5-10) in (Figure presented) between values reported for covalent nitrates and preformed nitronium salts.

SEPIAPTERIN REDUCTASE INHIBITORS FOR THE TREATMENT OF PAIN

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