873-69-8

Basic information

• Product Name: 2-Pyridinecarbaldehyde oxime
• Synonyms: SYM-2-PYRIDINEALDOXIME;PYRIDINE-2-CARBALDOXIME;PYRIDINE-2-CARBOXALDOXIME;PYRIDINE-2-ALDOXIME;PICOLINE ALDOXIME;TIMTEC-BB SBB004284;.alpha.-picolinealdoxime;2-Formylpyridine ketoxime
• CAS NO: 873-69-8
• Molecular Formula: C₆H₆N₂O
• Molecular Weight: 122.12
• EINECS: 212-849-6
• Product Categories: Pyridine;Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes
• Mol File: 873-69-8.mol
• Article Data: 58

Chemical Properties

• Melting Point: 110-112 °C(lit.)
• Boiling Point: 227.52°C (rough estimate)
• Flash Point: 73.5 °C
• Appearance: /
• Density: 1.2236 (rough estimate)
• Vapor Pressure: 0.032mmHg at 25°C
• Refractive Index: 1.4738 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: methanol: 0.1 g/mL, clear
• PKA: pK1: 3.42(+1);pK2: 10.22(0) (25°C)
• Water Solubility: 15 g/L (20 ºC)
• BRN: 109061
• CAS DataBase Reference: 2-Pyridinecarbaldehyde oxime(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyridinecarbaldehyde oxime(873-69-8)
• EPA Substance Registry System: 2-Pyridinecarbaldehyde oxime(873-69-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41-36/37/38-20/22
• Safety Statements: 26-36/37/39-37/39
• WGK Germany: 3
• RTECS: TJ4180000
• Hazardous Substances Data: 873-69-8(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Purification Methods

Recrystallise it from Et2O/pet ether or H2O. The picrate has m 169-171o (from aqueous EtOH). It is used in peptide synthesis. [UV: Grammaticakis Bull Chem Soc Fr 109, 116 1956, Ginsberg & Wilson J Am Chem Soc 79 481 1957, Hanania & Irvine Nature 183 40 1959, Green & Saville J Chem Soc 3887 1956, Beilstein E-isomer 21 I 288, 21 III/IV 3504, 21/7 V 305.]

InChI:InChI=1/C6H6N2O/c9-8-5-6-3-1-2-4-7-6/h1-5,9H/b8-5+

Synthetic route

pyridine-2-carbaldehyde (1121-60-4) → 2-pyridinealdoxime (873-69-8)

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In ethanol at 60℃; for 2h;	100%
Stage #1: pyridine-2-carbaldehyde With hydroxylamine hydrochloride In ethanol; water at 20℃; for 0.0166667h; Sealed tube; Stage #2: In ethanol; water at 120℃; for 1h; Sealed tube; Microwave irradiation;	98%
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 50℃; for 2h;	93.4%

(2-aminomethylpyridine) (3731-51-9) → 2-pyridinealdoxime (873-69-8)

Conditions	Yield
With Acetaldehyde oxime; oxygen; 1N,3N,5N-trihydroxy-1,3,5-triazin-2,4,6[1H,3H,5H]-trione In water at 100℃; for 42h; Green chemistry;	78%

2-Hydroxymethylpyridine (586-98-1) → 2-pyridinealdoxime (873-69-8)

Conditions	Yield
With hydroxylamine hydrochloride; dihydrogen peroxide; C18H13N2O4V In acetonitrile at 20 - 70℃; for 2.33333h;	78%

α-picoline (109-06-8) → 2-pyridinealdoxime (873-69-8)

Conditions	Yield
With tert.-butylnitrite; N-hydroxyphthalimide; copper diacetate In acetonitrile at 80℃; for 24h; Inert atmosphere;	73%
With potassium tert-butylate; ammonia 1.) -33 deg C, 1 h, 2.) -33 deg C; Yield given. Multistep reaction;

asoxime (34433-31-3, 119400-50-9) → 2-hydroxypyridin (142-08-5) + 2-Cyanopyridine (100-70-9) + 2-pyridinealdoxime (873-69-8) + pyridine-4-carboxylic acid (55-22-1) + formaldehyd (50-00-0) + isonicotinamide (1453-82-3)

Conditions	Yield
With sodium phosphate at 36.9℃; for 4h; Rate constant; rates of decomposition at various pH values and temperatures;

(3-Benzoylpyridinium (1)methyl)-(2'-hydroxyiminomethylpyridinium(1')methyl)ether dichloride → 2-hydroxypyridin (142-08-5) + 2-Cyanopyridine (100-70-9) + 2-pyridinealdoxime (873-69-8) + 3-Benzoylpyridine (5424-19-1) + formaldehyd (50-00-0)

Conditions	Yield
With sodium phosphate at 36.9℃; for 6h; Rate constant; rates of decomposition at various pH values and temperatures;

2-pyridinealdoxime (873-69-8) + C11H18IN2O2 (70723-34-1) → 2-Oximinomethyl-1-<3-(2,2,3,5,5-pentamethyl-1-oxylimidazolidin-4-ylidene)-2-oxopropyl>pyridinium iodide (94285-68-4)

Conditions	Yield
In N,N-dimethyl-formamide for 30h;	100%

2-pyridinealdoxime (873-69-8) + bis(tri-n-propylstannyl)oxide (1067-29-4) → (C3H7)3SnONCHC5H4N (57883-64-4)

Conditions	Yield
In benzene byproducts: H2O; 1:2 molar ratio of (C3H7)3SnOSn(C3H7)3 and hydroxylamine derivate, in dry benzene; removing of water formed by azeotropic distn.; reaction controlled by IR spectra; removing of solvent; vac. distn.;	100%

2-pyridinealdoxime (873-69-8) + benzoyl chloride (98-88-4) → C13H10N2O2

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h; Cooling with ice; Inert atmosphere;	100%

2-pyridinealdoxime (873-69-8) + acetyl chloride (75-36-5) → C8H8N2O2

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h; Cooling with ice; Inert atmosphere;	100%

2-pyridinealdoxime (873-69-8) + pivaloyl chloride (3282-30-2) → C11H14N2O2

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h; Cooling with ice; Inert atmosphere;	100%

2-pyridinealdoxime (873-69-8) + 1,4-bis(bromomethyl)benzene (623-24-5) → 1-(2-bromomethylbenzyl)-4-hydroxyiminomethylpyridinium bromide (78282-91-4)

Conditions	Yield
With acetone for 2h; Reflux;	98%
In acetone Reflux;
In acetone at 20℃;

2-pyridinealdoxime (873-69-8) → 2-Cyanopyridine (100-70-9)

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 3h;	97%
With trichloro(trifluoromethanesulfonato)titanium(IV) at 80℃; for 10h; Dehydration;	95%
With thionyl chloride; polyvinylpyrrolidone In dichloromethane at 20℃; for 0.25h; Dehydration;	93%

2-pyridinealdoxime (873-69-8) + phenylhydrazine (100-63-0) → pyridine-2-carboxaldehyde-2'-pyridyl-hydrazone (7727-07-3)

Conditions	Yield
iron(III) perchlorate In 1,2-dichloro-ethane at 20℃; for 1h;	96%

2-pyridinealdoxime (873-69-8) + (2,4-dinitro-phenyl)-hydrazine (119-26-6) → 2-pyridyl-2,4-dinitrophenyl ketazine (71606-79-6)

Conditions	Yield
iron(III) perchlorate In 1,2-dichloro-ethane at 20℃; for 3h;	95%

2-pyridinealdoxime (873-69-8) + pent-4-enoic acid (591-80-0) → C11H12N2O2

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 22h; Cooling with ice; Inert atmosphere;	95%

2-pyridinealdoxime (873-69-8) → N-hydroxypyridine-2-carboximidoyl chloride hydrochloride (39977-58-7)

Conditions	Yield
With benzyl(trimethyl)ammonium tetrachloroiodate In dichloromethane	94%
With chlorine In dichloromethane at -5 - 0℃; for 3h;	93%

2-pyridinealdoxime (873-69-8) + methyl iodide (74-88-4) → pralidoxime iodide (94-63-3, 29603-75-6, 74070-01-2)

Conditions	Yield
In acetone for 0.0666667h; Microwave irradiation;	93.5%
In ethanol for 6h; Heating;	81%
In acetonitrile for 6.5h; Reflux;	69%
In acetone for 4h; Reflux;
In N,N-dimethyl-formamide at 125℃; for 0.166667h; Solvent; Temperature;	90 %Spectr.

2-pyridinealdoxime (873-69-8) + 2-isopropoxy-1,3,2-benzodioxaborole (61676-63-9) → OC6H4OBONC(H)C5H4N (76565-90-7)

Conditions	Yield
In benzene byproducts: isopropanol; under anhydrous conditions, to a soln. of borole in benzene added organic compound, mixture refluxed under a fractionating column; i-PrOH removed azeotropically with benzene during 6 h, excess solvent removed, dried under vac., recrystd. from benzene; elem. anal.;	93%

2-pyridinealdoxime (873-69-8) + diphenyliodonium tetrafluoroborate → picolinaldehyde O-phenyl oxime

Conditions	Yield
Stage #1: 2-pyridinealdoxime With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: diphenyliodonium tetrafluoroborate In tetrahydrofuran at 20℃; for 1h;	93%

2-pyridinealdoxime (873-69-8) + Pentafluoropyridine (700-16-3) → (2-pyridinyl)(2,3,5,6-tetrafluoro-4-pyridinyl)methanone

Conditions	Yield
Stage #1: 2-pyridinealdoxime With sodium hydrogencarbonate In acetonitrile at 20℃; for 0.25h; Stage #2: Pentafluoropyridine In acetonitrile at 87℃; for 48h; Reflux;	93%

2-pyridinealdoxime (873-69-8) + 2,3-Dimethoxy-6-bromomethylnaphthalene (90929-68-3) → 1-<(6,7-dimethoxy-2-naphthalenyl)methyl>-2-<(hydroxyimino)methyl>pyridinium bromide (90929-69-4)

Conditions	Yield
In N,N-dimethyl-formamide 1.) 40 deg C, 18 h; 2.) 65 deg C, 1 h;	92%

2-pyridinealdoxime (873-69-8) + rhenium(I) pentacarbonyl chloride (14099-01-5) → [ReCl(CO)3(pyridine-2-aldoxime)] (1173886-01-5)

Conditions	Yield
In benzene soln. of Re complex and ligand (1 equiv.) in C6H6 was refluxed for 24 h; evapd. (vac.); recrystd.; elem. anal.;	92%
In toluene soln. of Re complex and ligand (1 equiv.) in toluene was refluxed for 24h; evapd. (vac.); recrystd.;

2-pyridinealdoxime (873-69-8) + acetic anhydride (108-24-7) → O-acetyl-2-pyridinecarboxaldoxime (74231-53-1)

Conditions	Yield
With triethylamine; dmap In dichloromethane at 20℃; for 14h;	91%

2-pyridinealdoxime (873-69-8) + acrylonitrile (107-13-1) → C9H9N3O (1167430-42-3)

Conditions	Yield
With N-benzyl-trimethylammonium hydroxide at 20℃; for 0.5h; Michael condensation;	91%

2-pyridinealdoxime (873-69-8) + 1,3-bis-(bromomethyl)benzene (626-15-3) → 1-(2-bromomethylbenzyl)-3-hydroxyiminomethylpyridinium bromide (1352826-60-8)

Conditions	Yield
With acetone for 2h; Reflux;	91%
In acetone Reflux;
In acetone at 20℃;

2-pyridinealdoxime (873-69-8) + methyl p-toluene sulfonate (80-48-8) → 1-Methyl-2-pyridinium-p-toluolsulfat (70275-57-9)

Conditions	Yield
In toluene for 3h; Solvent; Reflux;	91%

2-pyridinealdoxime (873-69-8) + nickel(II) chloride hexahydrate → Ni(2-pyridine aldoxime)2 dichloride

Conditions	Yield
In methanol (N2); slow addn. of Ni salt to a hot soln. of ligand in methanol, refluxat 50°C for 10 min, slow cooling; washing ppt. with cold methanol, drying; elem. anal.;	90%

2-pyridinealdoxime (873-69-8) + rhenium(I) pentacarbonyl bromide (14220-21-4) → [ReBr(CO)3(pyridine-2-aldoxime)] (1173886-02-6)

Conditions	Yield
In benzene soln. of Re complex and ligand (1 equiv.) in C6H6 was refluxed for 24 h; evapd. (vac.); recrystd.; elem. anal.;	90%
In toluene soln. of Re complex and ligand (1 equiv.) in toluene was refluxed for 24h; evapd. (vac.); recrystd.;

2-pyridinealdoxime (873-69-8) + Methyl methanesulfonate (66-27-3) → Contrathion (154-97-2, 29603-50-7, 105404-71-5)

Conditions	Yield
In acetonitrile at 80 - 85℃; for 7h; Solvent;	90%

2-pyridinealdoxime (873-69-8) + bis(3-methylphenyl)iodonium tetrafluoroborate → picolinaldehyde O-(3-tolyl) oxime

Conditions	Yield
Stage #1: 2-pyridinealdoxime With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: bis(3-methylphenyl)iodonium tetrafluoroborate In tetrahydrofuran at 20℃; for 1h;	90%

2-pyridinealdoxime (873-69-8) → pyridine-2-carbaldehyde (1121-60-4)

Conditions	Yield
With zinc(II) nitrate; silica gel for 0.0666667h; deoxymation; Irradiation;	89%
With cellulose supported Cu-nanoparticles In water at 80℃; for 0.0833333h; Microwave irradiation; Green chemistry;	79%
With iodine; sodium dodecyl-sulfate In water at 25 - 40℃; for 4h;	71%
With aluminum(III) nitrate nonahydrate; sodium bromide In dichloromethane at 20℃; for 30.5h;	58%

2-pyridinealdoxime (873-69-8) + acrylic acid methyl ester (292638-85-8) → C10H12N2O3 (1167430-43-4)

Conditions	Yield
With N-benzyl-trimethylammonium hydroxide at 20℃; for 0.666667h; Michael condensation;	89%

2-pyridinealdoxime (873-69-8) → 2-pyridylhydroxyiminomethyl chloride (69716-28-5)

Conditions	Yield
With N-chloro-succinimide In N,N-dimethyl-formamide at 20℃; for 12h;	87.1%
Stage #1: 2-pyridinealdoxime With N-chloro-succinimide In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: With hydrogenchloride In N,N-dimethyl-formamide at 20 - 50℃; Inert atmosphere; Stage #3: With N-chloro-succinimide In N,N-dimethyl-formamide at 50℃; Inert atmosphere;	76%
Stage #1: 2-pyridinealdoxime With N-chloro-succinimide In N,N-dimethyl-formamide at 25 - 30℃; for 8h; Stage #2: With water In N,N-dimethyl-formamide at 0℃;	70%

2-pyridinealdoxime (873-69-8) + diethyl germanium dichloride (13314-52-8) → C16H20GeN4O2

Conditions	Yield
Stage #1: 2-pyridinealdoxime With methanol; sodium Reflux; Inert atmosphere; Stage #2: diethyl germanium dichloride In benzene for 4h; Reflux; Inert atmosphere;	87%

Upstream product

• 586-98-1 2-Hydroxymethylpyridine 
• 3731-51-9 2-(Aminomethyl)pyridine 
• 34433-31-3 asoxime 
• 1121-60-4 pyridine-2-carbaldehyde 
• 109-06-8 α-picoline 

Downstream Products

• 116026-80-3 Pyridine-2-carbaldehyde O-ethyl-oxime 
• 78282-80-1 2-(Hydroxyimino-methyl)-1-phenethyl-pyridinium; iodide 
• 78282-69-6 2-(Hydroxyimino-methyl)-1-(3-methyl-benzyl)-pyridinium; bromide 
• 89603-98-5 C₂₈H₂₈N₄O₂⁽²⁺⁾*2Br^(1-) 
• 89603-97-4 C₂₇H₂₆N₄O₂⁽²⁺⁾*2Br^(1-) 
• 89604-00-2 C₃₀H₃₂N₄O₂⁽²⁺⁾*2Br^(1-) 
• 89603-99-6 C₂₉H₃₀N₄O₂⁽²⁺⁾*2Br^(1-) 
• 78282-76-5 C₁₆H₂₁N₃O⁽²⁺⁾*2I^(1-) 
• 54846-16-1 1-benzyl-2-((hydroxyimino)methyl)pyridine-1-ium-bromide 
• 78282-73-2 2-(Hydroxyimino-methyl)-1-(4-nitro-benzyl)-pyridinium; chloride 
• 128023-51-8 Pyridine-2-carbaldehyde O-{2-[4-(1,4-dioxa-spiro[4.5]dec-6-ylmethyl)-phenoxy]-propyl}-oxime 
• 128023-51-8 Pyridine-2-carbaldehyde O-{(R)-2-[4-(1,4-dioxa-spiro[4.5]dec-6-ylmethyl)-phenoxy]-propyl}-oxime 
• 128023-51-8 Pyridine-2-carbaldehyde O-{(S)-2-[4-(1,4-dioxa-spiro[4.5]dec-6-ylmethyl)-phenoxy]-propyl}-oxime 
• 78282-72-1 1-(4-Chloro-benzyl)-2-(hydroxyimino-methyl)-pyridinium; chloride 

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Pyridine derivatives based on the addition of trinitromethyl functional groups were synthesized by the reaction of N2O4 with the corresponding pyridinecarboxaldoximes, then they were converted into dinitromethylide hydrazinium salts. These energetic compounds were fully characterized by IR and NMR spectroscopy, elemental analysis, differential scanning calorimetry (DSC), and X-ray crystallography. These pyridine derivatives have good densities, positive enthalpies of formation, and acceptable sensitivity values. Theoretical calculations carried out using Gaussian 03 and EXPLO5 programs demonstrated good to excellent detonation velocities and pressures. Each of these compounds is superior in performance to TNT, while 2,6-bis(trinitromethyl)pyridine (D = 8700 m·s?1, P = 33.2 GPa) shows comparable detonation performance to that of RDX, but its thermal stability is too low, making it inferior to RDX.

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