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873-69-8 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.]

Check Digit Verification of cas no

The CAS Registry Mumber 873-69-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,7 and 3 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 873-69:
(5*8)+(4*7)+(3*3)+(2*6)+(1*9)=98
98 % 10 = 8
So 873-69-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H6N2O/c9-8-5-6-3-1-2-4-7-6/h1-5,9H/b8-5+

873-69-8 Well-known Company Product Price

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  • Alfa Aesar

  • (A16714)  Pyridine-2-carboxaldoxime, 99%   

  • 873-69-8

  • 25g

  • 631.0CNY

  • Detail
  • Alfa Aesar

  • (A16714)  Pyridine-2-carboxaldoxime, 99%   

  • 873-69-8

  • 100g

  • 1901.0CNY

  • Detail
  • Alfa Aesar

  • (A16714)  Pyridine-2-carboxaldoxime, 99%   

  • 873-69-8

  • 500g

  • 8040.0CNY

  • Detail

873-69-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Pyridine-2-Carboxaldoxime

1.2 Other means of identification

Product number -
Other names 2-Pyridinecarbaldehyde oxime

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:873-69-8 SDS

873-69-8Synthetic route

pyridine-2-carbaldehyde
1121-60-4

pyridine-2-carbaldehyde

2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

Conditions
ConditionsYield
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-aminomethylpyridine)

2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

Conditions
ConditionsYield
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-Hydroxymethylpyridine

2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; dihydrogen peroxide; C18H13N2O4V In acetonitrile at 20 - 70℃; for 2.33333h;78%
α-picoline
109-06-8

α-picoline

2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

Conditions
ConditionsYield
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;

A

2-hydroxypyridin
142-08-5

2-hydroxypyridin

B

2-Cyanopyridine
100-70-9

2-Cyanopyridine

C

2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

D

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

E

formaldehyd
50-00-0

formaldehyd

F

isonicotinamide
1453-82-3

isonicotinamide

Conditions
ConditionsYield
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

(3-Benzoylpyridinium (1)methyl)-(2'-hydroxyiminomethylpyridinium(1')methyl)ether dichloride

A

2-hydroxypyridin
142-08-5

2-hydroxypyridin

B

2-Cyanopyridine
100-70-9

2-Cyanopyridine

C

2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

D

3-Benzoylpyridine
5424-19-1

3-Benzoylpyridine

E

formaldehyd
50-00-0

formaldehyd

Conditions
ConditionsYield
With sodium phosphate at 36.9℃; for 6h; Rate constant; rates of decomposition at various pH values and temperatures;
2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

C11H18IN2O2
70723-34-1

C11H18IN2O2

2-Oximinomethyl-1-<3-(2,2,3,5,5-pentamethyl-1-oxylimidazolidin-4-ylidene)-2-oxopropyl>pyridinium iodide
94285-68-4

2-Oximinomethyl-1-<3-(2,2,3,5,5-pentamethyl-1-oxylimidazolidin-4-ylidene)-2-oxopropyl>pyridinium iodide

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 30h;100%
2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

bis(tri-n-propylstannyl)oxide
1067-29-4

bis(tri-n-propylstannyl)oxide

(C3H7)3SnONCHC5H4N
57883-64-4

(C3H7)3SnONCHC5H4N

Conditions
ConditionsYield
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

2-pyridinealdoxime

benzoyl chloride
98-88-4

benzoyl chloride

C13H10N2O2

C13H10N2O2

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 2h; Cooling with ice; Inert atmosphere;100%
2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

acetyl chloride
75-36-5

acetyl chloride

C8H8N2O2

C8H8N2O2

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 2h; Cooling with ice; Inert atmosphere;100%
2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

pivaloyl chloride
3282-30-2

pivaloyl chloride

C11H14N2O2

C11H14N2O2

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 3h; Cooling with ice; Inert atmosphere;100%
2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

1,4-bis(bromomethyl)benzene
623-24-5

1,4-bis(bromomethyl)benzene

1-(2-bromomethylbenzyl)-4-hydroxyiminomethylpyridinium bromide
78282-91-4

1-(2-bromomethylbenzyl)-4-hydroxyiminomethylpyridinium bromide

Conditions
ConditionsYield
With acetone for 2h; Reflux;98%
In acetone Reflux;
In acetone at 20℃;
2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
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

2-pyridinealdoxime

phenylhydrazine
100-63-0

phenylhydrazine

pyridine-2-carboxaldehyde-2'-pyridyl-hydrazone
7727-07-3

pyridine-2-carboxaldehyde-2'-pyridyl-hydrazone

Conditions
ConditionsYield
iron(III) perchlorate In 1,2-dichloro-ethane at 20℃; for 1h;96%
2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

(2,4-dinitro-phenyl)-hydrazine
119-26-6

(2,4-dinitro-phenyl)-hydrazine

2-pyridyl-2,4-dinitrophenyl ketazine
71606-79-6

2-pyridyl-2,4-dinitrophenyl ketazine

Conditions
ConditionsYield
iron(III) perchlorate In 1,2-dichloro-ethane at 20℃; for 3h;95%
2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

pent-4-enoic acid
591-80-0

pent-4-enoic acid

C11H12N2O2

C11H12N2O2

Conditions
ConditionsYield
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

2-pyridinealdoxime

N-hydroxypyridine-2-carboximidoyl chloride hydrochloride
39977-58-7

N-hydroxypyridine-2-carboximidoyl chloride hydrochloride

Conditions
ConditionsYield
With benzyl(trimethyl)ammonium tetrachloroiodate In dichloromethane94%
With chlorine In dichloromethane at -5 - 0℃; for 3h;93%
2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
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-pyridinealdoxime

2-isopropoxy-1,3,2-benzodioxaborole
61676-63-9

2-isopropoxy-1,3,2-benzodioxaborole

OC6H4OBONC(H)C5H4N
76565-90-7

OC6H4OBONC(H)C5H4N

Conditions
ConditionsYield
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

2-pyridinealdoxime

diphenyliodonium tetrafluoroborate

diphenyliodonium tetrafluoroborate

picolinaldehyde O-phenyl oxime

picolinaldehyde O-phenyl oxime

Conditions
ConditionsYield
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

2-pyridinealdoxime

Pentafluoropyridine
700-16-3

Pentafluoropyridine

(2-pyridinyl)(2,3,5,6-tetrafluoro-4-pyridinyl)methanone

(2-pyridinyl)(2,3,5,6-tetrafluoro-4-pyridinyl)methanone

Conditions
ConditionsYield
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-pyridinealdoxime

2,3-Dimethoxy-6-bromomethylnaphthalene
90929-68-3

2,3-Dimethoxy-6-bromomethylnaphthalene

1-<(6,7-dimethoxy-2-naphthalenyl)methyl>-2-<(hydroxyimino)methyl>pyridinium bromide
90929-69-4

1-<(6,7-dimethoxy-2-naphthalenyl)methyl>-2-<(hydroxyimino)methyl>pyridinium bromide

Conditions
ConditionsYield
In N,N-dimethyl-formamide 1.) 40 deg C, 18 h; 2.) 65 deg C, 1 h;92%
2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

rhenium(I) pentacarbonyl chloride
14099-01-5

rhenium(I) pentacarbonyl chloride

[ReCl(CO)3(pyridine-2-aldoxime)]
1173886-01-5

[ReCl(CO)3(pyridine-2-aldoxime)]

Conditions
ConditionsYield
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

2-pyridinealdoxime

acetic anhydride
108-24-7

acetic anhydride

O-acetyl-2-pyridinecarboxaldoxime
74231-53-1

O-acetyl-2-pyridinecarboxaldoxime

Conditions
ConditionsYield
With triethylamine; dmap In dichloromethane at 20℃; for 14h;91%
2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

acrylonitrile
107-13-1

acrylonitrile

C9H9N3O
1167430-42-3

C9H9N3O

Conditions
ConditionsYield
With N-benzyl-trimethylammonium hydroxide at 20℃; for 0.5h; Michael condensation;91%
2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

1,3-bis-(bromomethyl)benzene
626-15-3

1,3-bis-(bromomethyl)benzene

1-(2-bromomethylbenzyl)-3-hydroxyiminomethylpyridinium bromide
1352826-60-8

1-(2-bromomethylbenzyl)-3-hydroxyiminomethylpyridinium bromide

Conditions
ConditionsYield
With acetone for 2h; Reflux;91%
In acetone Reflux;
In acetone at 20℃;
2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

methyl p-toluene sulfonate
80-48-8

methyl p-toluene sulfonate

1-Methyl-2-pyridinium-p-toluolsulfat
70275-57-9

1-Methyl-2-pyridinium-p-toluolsulfat

Conditions
ConditionsYield
In toluene for 3h; Solvent; Reflux;91%
2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

nickel(II) chloride hexahydrate

nickel(II) chloride hexahydrate

Ni(2-pyridine aldoxime)2 dichloride

Ni(2-pyridine aldoxime)2 dichloride

Conditions
ConditionsYield
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

2-pyridinealdoxime

rhenium(I) pentacarbonyl bromide
14220-21-4

rhenium(I) pentacarbonyl bromide

[ReBr(CO)3(pyridine-2-aldoxime)]
1173886-02-6

[ReBr(CO)3(pyridine-2-aldoxime)]

Conditions
ConditionsYield
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

2-pyridinealdoxime

Methyl methanesulfonate
66-27-3

Methyl methanesulfonate

Conditions
ConditionsYield
In acetonitrile at 80 - 85℃; for 7h; Solvent;90%
2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

bis(3-methylphenyl)iodonium tetrafluoroborate

bis(3-methylphenyl)iodonium tetrafluoroborate

picolinaldehyde O-(3-tolyl) oxime

picolinaldehyde O-(3-tolyl) oxime

Conditions
ConditionsYield
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

2-pyridinealdoxime

pyridine-2-carbaldehyde
1121-60-4

pyridine-2-carbaldehyde

Conditions
ConditionsYield
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

2-pyridinealdoxime

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

C10H12N2O3
1167430-43-4

C10H12N2O3

Conditions
ConditionsYield
With N-benzyl-trimethylammonium hydroxide at 20℃; for 0.666667h; Michael condensation;89%
2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

2-pyridylhydroxyiminomethyl chloride
69716-28-5

2-pyridylhydroxyiminomethyl chloride

Conditions
ConditionsYield
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

2-pyridinealdoxime

diethyl germanium dichloride
13314-52-8

diethyl germanium dichloride

C16H20GeN4O2

C16H20GeN4O2

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

873-69-8Relevant articles and documents

Energetic Di-and trinitromethylpyridines: Synthesis and characterization

Zhang, Yiying,Sun, Xiaoyu,Yu, Shannan,Bao, Lingxiang,Sun, Chenghui,Pang, Siping

, (2018)

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.

-

Krause,Busch

, p. 4830,4831 (1960)

-

Metal-Stabilized Boronate Ester Cages

Fadaei-Tirani, Farzaneh,Giraldi, Erica,Scopelliti, Rosario,Severin, Kay

supporting information, p. 10873 - 10879 (2021/08/16)

Molecular cages with arylboronate ester caps at the vertices are described. The cages were obtained by metal-templated polycondensation reactions of a tris(2-formylpyridine oxime) ligand with arylboronic acids. Suited templates are triflate or triflimide salts of ZnII, FeII, CoII, or MnII. In the products, the metal ions are coordinated internally to the pyridyl and oximato N atoms adjacent to the boronate ester, resulting in an improved hydrolytic stability of the latter. It is possible to decorate the cages with cyano or aldehyde groups using functionalized arylboronic acids. The aldehyde groups allow for a postsynthetic modification of the cages via an imine bond formation.

One-Pot Regioselective Synthesis of 7-Bromo-2H-Benzo[b][1,4]Oxazin-3(4H)-One Linked Isoxazole Hybrids as Anti-Cancer Agents and Their Molecular Docking Studies

Karthik, B.,Kumar, A. Kannan,Nukala, Satheesh Kumar,Ravinder, M.,Swamy, T. Narasimha

, p. 1269 - 1275 (2021/12/23)

Abstract: Regioselective synthesis of some novel 7-bromo-2H-benzo[b][1,4]oxazin-3(4H)-one linked isoxazole hybrids via copper(I) catalyzed one-pot reaction of various aromatic aldehydes with 7-bromo-4-(prop-2-yn-1-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one was developed. The structures of the compounds that are synthesized are confirmed by 1H NMR, 13C NMR, and mass spectra. All the hybrids have been tested for their in vitro anticancer activity against four human cancer cell lines, including HeLa, MCF-7, A549, and PC3. Three of the compounds exhibited remarkable anticancer activity compared to standard drug etoposide. Molecular docking studies with EGFR also strengthened the in vitro anticancer activity.

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