1083-48-3

Basic information

• Product Name: 4-(4-Nitrobenzyl)pyridine
• Synonyms: TIMTEC-BB SBB008854;1-(p-Nitrobenzyl)pyridine;4-(p-nitrobenzyl)-pyridin;4-[(4-nitrophenyl)methyl]-pyridin;4-[(4-nitrophenyl)methyl]-Pyridine;gamma-(4-Nitrobenzyl)pyridine;NBP;Pyridine, 4-(p-nitrobenzyl)-
• CAS NO: 1083-48-3
• Molecular Formula: C₁₂H₁₀N₂O₂
• Molecular Weight: 214.22
• EINECS: 214-108-2
• Product Categories: Heterocyclic Compounds;C9 to C46;Heterocyclic Building Blocks;Pyridines;Derivatization Reagents TLC;TLC Reagents, N-RSpectroscopy;TLC Visualization Reagents (alphabetic sort);UV/Vis Reagents;UV/Visible (UV/VIS) Spectroscopy;Building Blocks;C12;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 1083-48-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 69-71 °C(lit.)
• Boiling Point: 354.35°C (rough estimate)
• Flash Point: 185.6 °C
• Appearance: Light yellow/Crystals or Crystalline Powder
• Density: 1.2042 (rough estimate)
• Vapor Pressure: 9.76E-06mmHg at 25°C
• Refractive Index: 1.6660 (estimate)
• Storage Temp.: 0-6°C
• PKA: 5.51±0.10(Predicted)
• Water Solubility: Soluble in acetone. Insoluble in water.
• Sensitive: Light Sensitive
• BRN: 170877
• CAS DataBase Reference: 4-(4-Nitrobenzyl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-Nitrobenzyl)pyridine(1083-48-3)
• EPA Substance Registry System: 4-(4-Nitrobenzyl)pyridine(1083-48-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: UT6360000
• F: 10-23
• TSCA: Yes
• Hazardous Substances Data: 1083-48-3(Hazardous Substances Data)

Usage

Chemical Properties

LIGHT YELLOW CRYSTALS OR CRYSTALLINE POWDER

Uses

Different sources of media describe the Uses of 1083-48-3 differently. You can refer to the following data:
1. 4-(4-Nitrobenzyl)pyridine is used in tests for alkylating agents1 and in a spectroscopic method for phosgene determination.2
2. 4-(4-Nitrobenzyl)pyridine is a chemical used for the detection of epoxides and methylating reagents.
3. 4-(4-Nitrobenzyl)pyridine is used in spectroscopic method for the determination of phosgene. It is also used in tests for alkylating agents.

Purification Methods

Crystallise PNBP from aqueous EtOH or cyclohexane. The hydrochloride has m 194-196o(dec, from EtOH), and the picrate has m 168o(dec, from EtOH/EtOAc). [Beilstein 20 II 272, 20/7 V 564.]

InChI:InChI=1/C12H10N2O2/c15-14(16)12-3-1-10(2-4-12)9-11-5-7-13-8-6-11/h1-8H,9H2

Synthetic route

4-(Chloromethyl)pyridine (10445-91-7) + para-dinitrobenzene (100-25-4) → 4-Nitrobenzylpyridin (1083-48-3)

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 1h;	41%

4-(Chloromethyl)pyridine (10445-91-7) + nitrobenzene (98-95-3) → 4-Nitrobenzylpyridin (1083-48-3) + 4-(2-nitrobenzyl)pyridine (60288-89-3)

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 1h;	A 37% B 28%

4-benzyl pyridine (2116-65-6) → 4-Nitrobenzylpyridin (1083-48-3)

Conditions	Yield
With sulfuric acid; nitric acid at 10 - 50℃;	27%

4-benzyl pyridine (2116-65-6) + sulfuric acid (7664-93-9) + nitric acid (1.6 mol) → 4-Nitrobenzylpyridin (1083-48-3) + 4-(3-nitro-benzyl)-pyridine (32341-81-4) + 4-(2',4'-Dinitrobenzyl)-pyridin (1603-85-6)

Conditions	Yield
at 20℃;

sulfuric acid (7664-93-9) + 4-benzyl-pyridine; nitrate → 4-Nitrobenzylpyridin (1083-48-3) + 4-(3-nitro-benzyl)-pyridine (32341-81-4)

Conditions	Yield
at 50℃;

picoline (108-89-4) → 4-Nitrobenzylpyridin (1083-48-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 50 °C / Inert atmosphere 1.2: 2 h / -50 °C / Inert atmosphere 2.1: palladium(II) trifluoroacetate; tricyclohexylphosphine; caesium carbonate / o-xylene / 6 h / Inert atmosphere; Reflux View Scheme

2,4-dimethyl-3-(4-pyridylmethyl)-3-pentanol + para-nitrophenyl bromide (586-78-7) → 4-Nitrobenzylpyridin (1083-48-3)

Conditions	Yield
With palladium(II) trifluoroacetate; caesium carbonate; tricyclohexylphosphine In o-xylene for 6h; Inert atmosphere; Reflux;

para-dinitrobenzene (100-25-4) + 4-picolylchloride hydrochloride (1822-51-1) → 4-Nitrobenzylpyridin (1083-48-3)

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere;	300 mg

4-Nitrobenzylpyridin (1083-48-3) → 4-(4-aminobenzyl)pyridine (27692-74-6)

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In methanol at 20℃; for 12h;	100%
With polymer-CH2NMe3Cl; triethylammonium formate; palladium In ethanol at 100℃; for 48h;	99%
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 0.5h;	99%

4-Nitrobenzylpyridin (1083-48-3) → (4-nitrophenyl)(pyridin-4-yl)methanone (39055-88-4)

Conditions	Yield
With potassium permanganate for 1.33333h;	100%
With Phenylselenyl bromide; oxygen; acetic acid In water; dimethyl sulfoxide at 100℃; for 22h; Schlenk technique;	97%
With tert.-butylhydroperoxide; 1-n-butyl-3-methylimidazolim bromide In water at 60℃; for 12h;	83%

4-Nitrobenzylpyridin (1083-48-3) → 4-(4-nitrobenzyl)pyridine 1-oxide (26199-99-5)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In Isopropyl acetate at 10 - 35℃; for 5.83333h; Green chemistry;	98.5%
With polymer-supported 2-benzenesulfonyl-3-(4-nitrophenyl)oxaziridine In dichloromethane at 100℃; for 0.0333333h; Microwave irradiation;	92%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 2h;	83%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane; water

4-Nitrobenzylpyridin (1083-48-3) + benzyl bromide (100-39-0) → 1-benzyl-4-(4-nitrobenzyl)pyridine-1-ium bromide (83118-55-2)

Conditions	Yield
With silica gel In neat (no solvent) Solvent; Reagent/catalyst; Microwave irradiation;	98%
In acetone	90%
In acetone at 37℃; Product distribution; in phosphate buffer; study of half-live; molar fraction (percentage) of the alkylated NBP product at the end of the alkylation reaction, selectivity constant;
In acetone for 24h; Heating;

4-Nitrobenzylpyridin (1083-48-3) + 1-bromomethyl-4-nitro-benzene (100-11-8) → 1,4-bis(4-nitrobenzyl)pyridine-1-ium bromide (83118-60-9)

Conditions	Yield
With silica gel In neat (no solvent) Solvent; Reagent/catalyst; Microwave irradiation;	98%
In acetone at 37℃; Product distribution; in phophate buffer; study of half-live; molar fraction (percentage) of the alkylated NBP product at the end of the alkylation reaction, selectivity constant;
In acetone for 24h; Heating;

4-Nitrobenzylpyridin (1083-48-3) + 1,3,5-tris(bromomethyl)-2,4,6-trimethylbenzene (21988-87-4) → 1,1',1''-(2,4,6-trimethylbenzene-1,3,5-triyl)tris(methylene)tris(4-(4-nitrobenzyl)pyridine-1-ium) bromide

Conditions	Yield
With silica gel In neat (no solvent) Solvent; Reagent/catalyst; Microwave irradiation;	98%

2-Bromoacetylthiophene (10531-41-6) + 4-Nitrobenzylpyridin (1083-48-3) → 4-(4-nitro-benzyl)-1-(2-oxo-2-thiophen-2-yl-ethyl)-pyridinium; bromide

Conditions	Yield
In chloroform for 16h; Heating;	91.5%

4-Nitrobenzylpyridin (1083-48-3) → 4-(piperidin-4-ylmethyl)-phenylamine (37581-35-4)

Conditions	Yield
With hydrogenchloride; platinum (IV) oxide In ethanol; water	86%

4-Nitrobenzylpyridin (1083-48-3) + Pt(C12H10N2)Cl2 → Pt(C12H10N2)(O2NC6H4CH2C5H4N)Cl(1+)*Cl(1-)*3H2O={Pt(C12H10N2)(O2NC6H4CH2C5H4N)Cl}Cl*3H2O

Conditions	Yield
In water addn. of water to Pt-complex and pyridine derivative, mixt. heated (water bath, 10 min), addn. of EtOH, heated (15 min), dark-green soln.; filtration, addn. of ether to the filtrate with stirring, upper layer poured off, residue treated repeatedly and ground with acetone/ether (1:2), filtration, dried in air; elem. anal.;	86%

4-Nitrobenzylpyridin (1083-48-3) + (3-Chloro-quinoxalin-2-yl)-(toluene-4-sulfonyl)-acetonitrile (121512-59-2) → 2-(4-Nitro-benzyl)-indolizino[2,3-b]quinoxaline-12-carbonitrile

Conditions	Yield
at 130 - 150℃;	85%

4-Nitrobenzylpyridin (1083-48-3) + (E)-1,4-dibromobutene (821-06-7) → but-(2E)-en-1,4-diyl-1,1'-bis(4-(4-nitrobenzyl)-pyridinium) dibromide

Conditions	Yield
In N,N-dimethyl-formamide at 70℃;	81%

Hydrogen trans-Bis(dimethhyl sulfoxide) tetrachlororuthenate(III) + 4-Nitrobenzylpyridin (1083-48-3) → trans-Na[RuCl4(dimethylsulfoxide)(4-(4-nitrobenzyl)pyridine)] (1353894-15-1)

Conditions	Yield
In acetone dissolving of Na(Ru(DMSO)2Cl4) in acetone at room temp., addn. dropwise of soln. of 4-(4-nitrobenzyl)pyridine in acetone, stirring at room temp.for 30 min; removal of solvent under decreased pressure, addn. of CH2Cl2 and Et2O, pptn. for 10 min, filtration, washing with Et2O; elem. anal.;	81%

4-Nitrobenzylpyridin (1083-48-3) + p-toluenesulfonyl chloride (98-59-9) → 4-<(4-Methylphenylsulfonyl)(4-nitrophenyl)methyl>pyridin (116665-01-1)

Conditions	Yield
With triethylamine In dichloromethane for 60h;	79%

hydrogenchloride (7647-01-0) + 4-Nitrobenzylpyridin (1083-48-3) + ruthenium(III) trichloride hydrate → (4-(4-nitrobenzyl)pyridine)H[trans-RuCl4(4-(4-nitrobenzyl)pyridine)]

Conditions	Yield
Stage #1: hydrogenchloride; ruthenium(III) trichloride hydrate In ethanol; water for 3h; Reflux; Stage #2: 4-Nitrobenzylpyridin With hydrogenchloride In ethanol; water for 3h; Reflux;	76%

formic acid (64-18-6) + 4-Nitrobenzylpyridin (1083-48-3) → C13H14N2 + p-<(4-pyridyl)methyl>-N,N-dimethylaniline (131416-55-2)

Conditions	Yield
With tetrakis(triphenylphosphine)platinum; phenylsilane; C30H51Cl3Mo3N6PPtS4(1+)*BF4(1-) In tetrahydrofuran at 70℃; under 760.051 Torr; Inert atmosphere; Schlenk technique; chemoselective reaction;	A 21% B 72%

Hydrogen trans-Bis(dimethhyl sulfoxide) tetrachlororuthenate(III) + 4-Nitrobenzylpyridin (1083-48-3) → trans-[4-(4-nitrobenzyl)pyridinium][RuCl4(dimethylsulfoxide)(4-(4-nitrobenzyl)pyridine)] (1353894-14-0)

Conditions	Yield
In methanol dissolving of ((DMSO)2H)(Ru(DMSO)2Cl4) in MeOH at room temp., addn. dropwise of soln. of 4-(4-nitrobenzyl)pyridine in MeOH, stirring at room temp. for 3 h; pptn., filtration, washing with MeOH; elem. anal.;	55%

4-Nitrobenzylpyridin (1083-48-3) + ethyl acrylate (140-88-5) → C17H18N2O4

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; Michael Addition; Inert atmosphere;	50%

3-(4-nitrophenyl)-propenal (49678-08-2) + 4-Nitrobenzylpyridin (1083-48-3) → (3R,4S)-3,4-bis(4-nitrophenyl)-4-(pyridin-4-yl)butan-1-ol (1304788-73-5) + (3R,4R)-3,4-bis(4-nitrophenyl)-4-(pyridin-4-yl)butan-1-ol (1304788-81-5)

Conditions	Yield
Stage #1: 3-(4-nitrophenyl)-propenal; 4-Nitrobenzylpyridin With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; 1,4-diaza-bicyclo[2.2.2]octane In tetrahydrofuran at 23℃; for 24h; Michael addition; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol at 0℃; for 0.5h; optical yield given as %ee;	A 39% B 46%

(E)-3-(furan-3-yl)propenal (54355-99-6) + 4-Nitrobenzylpyridin (1083-48-3) → (3S,4S)-3-(furan-3-yl)-4-(4-nitrophenyl)-4-(pyridin-4-yl)butan-1-ol + (3R,4S)-3-(furan-3-yl)-4-(4-nitrophenyl)-4-(pyridin-4-yl)butan-1-ol + (3S,4R)-3-(furan-3-yl)-4-(4-nitrophenyl)-4-(pyridin-4-yl)butan-1-ol + (3R,4R)-3-(furan-3-yl)-4-(4-nitrophenyl)-4-(pyridin-4-yl)butan-1-ol

Conditions	Yield
Stage #1: (E)-3-(furan-3-yl)propenal; 4-Nitrobenzylpyridin With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; 1,4-diaza-bicyclo[2.2.2]octane In tetrahydrofuran at 23℃; for 24h; Michael addition; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol at 0℃; for 0.5h; optical yield given as %ee;	A n/a B 39% C n/a D 43%

4-Nitrobenzylpyridin (1083-48-3) + (E)-4-chlorocinnamic aldehyde (1075-77-0) → (3R,4S)-3-(4-chlorophenyl)-4-(4-nitrophenyl)-4-(pyridin-4-yl)butan-1-ol (1304788-74-6) + (3R,4R)-3-(4-chlorophenyl)-4-(4-nitrophenyl)-4-(pyridin-4-yl)butan-1-ol (1304788-82-6)

Conditions	Yield
Stage #1: 4-Nitrobenzylpyridin; (E)-4-chlorocinnamic aldehyde With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; 1,4-diaza-bicyclo[2.2.2]octane In tetrahydrofuran at 40℃; for 24h; Michael addition; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol at 0℃; for 0.5h; optical yield given as %ee;	A 34% B 41%

4-Nitrobenzylpyridin (1083-48-3) + [Cu(O(C6H4)CHN(C6H4O))]2 (125565-47-1, 14649-70-8) → C25H19CuN3O4

Conditions	Yield
In dimethyl sulfoxide at 170℃;	41%

(μ-H)3(CO)9Os3(μ3-CCl) + 4-Nitrobenzylpyridin (1083-48-3) → [Os3(μ-H)2(CO)9(μ3-CNC5H4CH2C6H4NO2)]

Conditions	Yield
With DBU In dichloromethane N2-atmosphere; addn. of 1 equiv. DBU to mixt. of Os-cluster and 10 equiv. ligand, stirring (room temp., 30 min); concn. (reduced pressure), thin layer chromy. (SiO2, hexane/CH2Cl2=3:2 v/v); recrystn.;	38%

4-Nitrobenzylpyridin (1083-48-3) + 4-methoxy-trans-cinnamaldehyde (24680-50-0, 71277-11-7, 1963-36-6) → (3S,4S)-3-(4-methoxyphenyl)-4-(4-nitrophenyl)-4-(pyridin-4-yl)butan-1-ol + (3R,4S)-3-(4-methoxyphenyl)-4-(4-nitrophenyl)-4-(pyridin-4-yl)butan-1-ol (1304788-72-4) + (3S,4R)-3-(4-methoxyphenyl)-4-(4-nitrophenyl)-4-(pyridin-4-yl)butan-1-ol + (3R,4R)-3-(4-methoxyphenyl)-4-(4-nitrophenyl)-4-(pyridin-4-yl)butan-1-ol (1304788-80-4)

Conditions	Yield
Stage #1: 4-Nitrobenzylpyridin; 4-methoxy-trans-cinnamaldehyde With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; 1,4-diaza-bicyclo[2.2.2]octane In tetrahydrofuran at 23℃; for 48h; Michael addition; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol at 0℃; for 0.5h; optical yield given as %ee;	A n/a B 24% C n/a D 34%

4-Nitrobenzylpyridin (1083-48-3) + 4-methyl-cinnamaldehyde (56578-35-9) → (3S,4S)-4-(4-nitrophenyl)-4-(pyridin-4-yl)-3-(p-tolyl)butan-1-ol + (3R,4S)-4-(4-nitrophenyl)-4-(pyridin-4-yl)-3-(p-tolyl)butan-1-ol (1304788-77-9) + (3S,4R)-4-(4-nitrophenyl)-4-(pyridin-4-yl)-3-(p-tolyl)butan-1-ol + (3R,4R)-4-(4-nitrophenyl)-4-(pyridin-4-yl)-3-(p-tolyl)butan-1-ol (1304788-85-9)

Conditions	Yield
Stage #1: 4-Nitrobenzylpyridin; 4-methyl-cinnamaldehyde With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; 1,4-diaza-bicyclo[2.2.2]octane In tetrahydrofuran at 23℃; for 24h; Michael addition; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol at 0℃; for 0.5h; optical yield given as %ee;	A n/a B 33% C n/a D 33%

4-Nitrobenzylpyridin (1083-48-3) + (2E)-3-(4-trifluoromethylphenyl)prop-2-enal (95123-61-8) → (3R,4S)-4-(4-nitrophenyl)-4-(pyridin-4-yl)-3-(4-(trifluoromethyl)phenyl)butan-1-ol (1304788-76-8) + (3R,4R)-4-(4-nitrophenyl)-4-(pyridin-4-yl)-3-(4-(trifluoromethyl)phenyl)butan-1-ol (1304788-84-8)

Conditions	Yield
Stage #1: 4-Nitrobenzylpyridin; (2E)-3-(4-trifluoromethylphenyl)prop-2-enal With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; 1,4-diaza-bicyclo[2.2.2]octane In tetrahydrofuran at 23℃; for 24h; Michael addition; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol at 0℃; for 0.5h; optical yield given as %ee;	A 32% B 33%

4-Nitrobenzylpyridin (1083-48-3) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 4-(1-(4-nitrophenyl)vinyl)pyridine (1471806-91-3)

Conditions	Yield
With dipotassium peroxodisulfate; copper (II) trifluoroacetate hydrate at 100℃; for 24h; Schlenk technique; Inert atmosphere;	32%

4-Nitrobenzylpyridin (1083-48-3) + 1-ethylcyclohexyl acetate (3742-81-2) + 1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide (56632-81-6) → 2,6-dibromo-9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purine (134217-12-2)

Conditions	Yield
silica gel In 1,1-dichloroethane	31.6%

4-Nitrobenzylpyridin (1083-48-3) + 1-ethylcyclohexyl acetate (3742-81-2) + 1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide (56632-81-6) + 2,6-dibromopurine (1196-41-4) → 2,6-Dibromo-9-(3-O-acetyl-5-O-benzyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purine

Conditions	Yield
molecular sieve In 1,1-dichloroethane	31.6%

Upstream product

• 2116-65-6 4-benzyl pyridine 
• 7664-93-9 sulfuric acid 
• 10445-91-7 4-(Chloromethyl)pyridine 
• 100-25-4 para-dinitrobenzene 
• 98-95-3 nitrobenzene 
• 1822-51-1 4-picolylchloride hydrochloride 
• 586-78-7 para-nitrophenyl bromide 
• 108-89-4 picoline 

Downstream Products

• 58100-27-9 methyl-NBP iodide 
• 27692-74-6 4-(4-aminobenzyl)pyridine 
• 1603-85-6 4-(2',4'-Dinitrobenzyl)-pyridin 
• 81587-15-7 N-(2-hydroxyethyl)-4-(p-nitrobenzylidene)-1,4-dihydropyridine 
• 116665-01-1 4-<(4-Methylphenylsulfonyl)(4-nitrophenyl)methyl>pyridin 
• 26199-99-5 4-(4-nitrobenzyl)pyridine N-oxide 
• 39055-88-4 (4-nitrophenyl)(pyridin-4-yl)methanone 
• 46835-29-4 NBP-Me 
• 442846-98-2 1-methyl-4-(4-nitro-benzyl)-1,2,3,6-tetrahydro-pyridine 

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