[ CAS No. 694-59-7 ] {[proInfo.proName]}

Name: 694-59-7|Pyridine 1-oxide|97%
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SKU: A119987
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Quality Control of [ 694-59-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 694-59-7 ]

Product Details of [ 694-59-7 ]

CAS No. :	694-59-7	MDL No. :	MFCD00006194
Formula :	C₅H₅NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ILVXOBCQQYKLDS-UHFFFAOYSA-N
M.W :	95.10	Pubchem ID :	12753
Synonyms :

Calculated chemistry of [ 694-59-7 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	27.6
TPSA :	25.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.73 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.75
Log Po/w (XLOGP3) :	-1.2
Log Po/w (WLOGP) :	0.32
Log Po/w (MLOGP) :	0.57
Log Po/w (SILICOS-IT) :	0.21
Consensus Log Po/w :	0.13

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.31
Solubility :	46.8 mg/ml ; 0.492 mol/l
Class :	Very soluble
Log S (Ali) :	1.16
Solubility :	1370.0 mg/ml ; 14.4 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.54
Solubility :	27.4 mg/ml ; 0.288 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.38

Safety of [ 694-59-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 694-59-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 694-59-7 ]
Downstream synthetic route of [ 694-59-7 ]

[ 694-59-7 ] Synthesis Path-Upstream 1~20

1
[ 694-59-7 ]
[ 14248-50-1 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1951, vol. 70, p. 581,587
[2] Journal of Organic Chemistry, 1953, vol. 18, p. 534,541

2
[ 694-59-7 ]
[ 2044-73-7 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 305 - 309

3
[ 694-59-7 ]
[ 1600-27-7 ]
[ 64-19-7 ]
[ 14305-17-0 ]
[ 25373-69-7 ]

Reference： [1] Yakugaku Zasshi, 1953, vol. 73, p. 823[2] Chem.Abstr., 1954, p. 9946
[3] Recueil des Travaux Chimiques des Pays-Bas, 1958, vol. 77, p. 343[4] Recueil des Travaux Chimiques des Pays-Bas, 1962, vol. 81, p. 124,127

4
[ 694-59-7 ]
[ 626-05-1 ]

Reference： [1] Organic Letters, 2009, vol. 11, # 2, p. 421 - 423
[2] Journal of Organic Chemistry, 2009, vol. 74, # 21, p. 8309 - 8313

5
[ 694-59-7 ]
[ 110-86-1 ]
[ 142-08-5 ]
[ 2739-97-1 ]
[ 366-18-7 ]
[ 109-97-7 ]

Reference： [1] Heterocycles, 1990, vol. 31, # 5, p. 783 - 786

6
[ 694-59-7 ]
[ 2859-68-9 ]

Reference： [1] Journal of Organometallic Chemistry, 1987, vol. 333, p. 139 - 154
[2] Journal of Organometallic Chemistry, 1987, vol. 333, p. 139 - 154

7
[ 694-59-7 ]
[ 274-87-3 ]

Reference： [1] Journal of Organic Chemistry, 2014, vol. 79, # 7, p. 3249 - 3254
[2] Inorganic Chemistry, 2014, vol. 53, # 12, p. 6204 - 6223
[3] Journal of Organic Chemistry, 2006, vol. 71, # 25, p. 9540 - 9543
[4] Chemistry Letters, 1983, p. 1745 - 1748

8
[ 694-59-7 ]
[ 4648-54-8 ]
[ 124-63-0 ]
[ 274-87-3 ]
[ 10090-05-8 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 8, p. 2419 - 2420

9
[ 694-59-7 ]
[ 25813-25-6 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1951, vol. 70, p. 581,587

10
[ 694-59-7 ]
[ 88284-48-4 ]
[ 33421-36-2 ]

Reference： [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 34, p. 6834 - 6839
[2] Synthesis (Germany), 2015, vol. 46, # 4,

11
[ 694-59-7 ]
[ 88284-48-4 ]
[ 33421-36-2 ]
[ 54168-07-9 ]

Reference： [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 34, p. 6834 - 6839
[2] Organic and Biomolecular Chemistry, 2012, vol. 10, # 34, p. 6834 - 6839

12
[ 694-59-7 ]
[ 73501-39-0 ]
[ 88284-48-4 ]
[ 33421-36-2 ]
[ 54168-07-9 ]
[ 1394900-26-5 ]

Reference： [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 34, p. 6834 - 6839

13
[ 694-59-7 ]
[ 77086-38-5 ]
[ 1658-42-0 ]

Reference： [1] Organic Letters, 2014, vol. 16, # 12, p. 3336 - 3339

14
[ 694-59-7 ]
[ 77086-38-5 ]
[ 1658-42-0 ]

Reference： [1] Organic Letters, 2014, vol. 16, # 12, p. 3336 - 3339
[2] Organic Letters, 2014, vol. 16, # 12, p. 3336 - 3339

15
[ 694-59-7 ]
[ 13509-19-8 ]

Reference： [1] Journal of Organometallic Chemistry, 1997, vol. 544, # 2, p. 163 - 174

16
[ 694-59-7 ]
[ 19235-88-2 ]

Reference： [1] Journal of Organometallic Chemistry, 1997, vol. 544, # 2, p. 163 - 174

17
[ 288-13-1 ]
[ 694-59-7 ]
[ 25700-11-2 ]

Reference： [1] Organic Letters, 2010, vol. 12, # 22, p. 5254 - 5257
[2] Organic Letters, 2011, vol. 13, # 7, p. 1840 - 1843

18
[ 694-59-7 ]
[ 51953-18-5 ]
[ 64264-15-9 ]
[ 126126-58-7 ]
[ 126126-57-6 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 8, p. 1984 - 1986

19
[ 694-59-7 ]
[ 86521-05-3 ]

Reference： [1] Tetrahedron Letters, 1985, vol. 26, # 27, p. 3191 - 3194

20
[ 694-59-7 ]
[ 83640-36-2 ]

Reference： [1] Patent: US4999364, 1991, A,
[2] Patent: US4866086, 1989, A,

[ 694-59-7 ] Synthesis Path-Downstream 1~88

1
[ 694-59-7 ]
[ 778-28-9 ]
1-butoxy-pyridinium; toluene-4-sulfonate [ No CAS ]

Reference： [1]Chemical and pharmaceutical bulletin,1959,vol. 7,p. 925,928

2
[ 694-59-7 ]
[ 51953-18-5 ]
[ 64264-15-9 ]
[ 126126-58-7 ]
[ 126126-57-6 ]

Reference： [1]Chemical and pharmaceutical bulletin,1989,vol. 37,p. 1984 - 1986

3
[ 694-59-7 ]
[ 770-09-2 ]
[ 101-82-6 ]

Reference： [1]Organic Letters,2019,vol. 21,p. 3407 - 3411
[2]Tetrahedron Letters,1983,vol. 24,p. 889 - 890

4
[ 694-59-7 ]
[ 4648-54-8 ]
[ 124-63-0 ]
[ 274-87-3 ]
[ 10090-05-8 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1985,vol. 58,p. 2419 - 2420

5
[ 694-59-7 ]
[ 6602-28-4 ]
[ 6890-62-6 ]
[ 13161-30-3 ]

Reference： [1]Journal of Physical Chemistry,1980,vol. 84,p. 532 - 534

6
[ 694-59-7 ]
[ 274-87-3 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 3249 - 3254
[2]Inorganic Chemistry,2014,vol. 53,p. 6204 - 6223
[3]Journal of Organic Chemistry,2006,vol. 71,p. 9540 - 9543
[4]Chemistry Letters,1983,p. 1745 - 1748

7
[ 694-59-7 ]
[ 7664-93-9 ]
[ 7697-37-2 ]
[ 1122-61-8 ]
[ 15009-91-3 ]
[ 1124-33-0 ]

Reference： [1]Journal of Organic Chemistry,1953,vol. 18,p. 534,541

8
[ 694-59-7 ]
[ 504-29-0 ]
[ 98-59-9 ]
[ 52776-76-8 ]
[ 58996-80-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 62% 2: 17%	With potassium carbonate In chloroform at 20℃; for 2h;
1: 31% 2: 60%	With potassium hydroxide In chloroform at 20℃; for 2h;

Reference： [1]Solekhova; Kurbatov [Russian Journal of Organic Chemistry, 2005, vol. 41, # 1, p. 128 - 130]
[2]Solekhova; Kurbatov [Russian Journal of Organic Chemistry, 2005, vol. 41, # 1, p. 128 - 130]

9
[ 694-59-7 ]
[ 52776-76-8 ]
[ 58996-80-8 ]

Yield	Reaction Conditions	Operation in experiment
39%	With potassium hydroxide; p-toluenesulfonyl chloride In chloroform at 20℃; for 2h;

Reference： [1]Solekhova; Kurbatov [Russian Journal of Organic Chemistry, 2005, vol. 41, # 1, p. 128 - 130]

10
[ 694-59-7 ]
[ 217813-00-8 ]
3-(4,5-difluoro-2-hydroxyphenyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With cesium fluoride In acetonitrile at 20℃; for 24h;

Reference： [1]Raminelli, Cristiano; Liu, Zhijian; Larock, Richard C. [Journal of Organic Chemistry, 2006, vol. 71, # 12, p. 4689 - 4691]

11
[ 694-59-7 ]
[ 7189-69-7 ]
C₈H₇N₃O₃S [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 327 - 330

12
[ 694-59-7 ]
[ 13509-19-8 ]

Reference： [1]Journal of Organometallic Chemistry,1997,vol. 544,p. 163 - 174

13
[ 694-59-7 ]
[ 29082-91-5 ]

Reference： [1]Journal of Organometallic Chemistry,1997,vol. 544,p. 163 - 174

14
[ 694-59-7 ]
[ 19235-88-2 ]

Reference： [1]Journal of Organometallic Chemistry,1997,vol. 544,p. 163 - 174

15
[ 694-59-7 ]
[ 2859-68-9 ]

Reference： [1]Journal of Organometallic Chemistry,1987,vol. 333,p. 139 - 154
[2]Journal of Organometallic Chemistry,1987,vol. 333,p. 139 - 154

16
[ 694-59-7 ]
[ 14248-50-1 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1951,vol. 70,p. 581,587
[2]Journal of Organic Chemistry,1953,vol. 18,p. 534,541

17
[ 694-59-7 ]
[ 25813-25-6 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1951,vol. 70,p. 581,587

18
[ 694-59-7 ]
[ 1122-61-8 ]

Reference： [1]Journal of Organic Chemistry,1953,vol. 18,p. 534,541
[2]Journal of Chemical Research,2015,vol. 39,p. 209 - 212

19
[ 694-59-7 ]
[ 100-70-9 ]
[ 2459-07-6 ]

Yield	Reaction Conditions	Operation in experiment
	With HCl (gas) In methanol; water; ethyl acetate	1.3 Step 3 Dry HCl (gas) was bubbled through anhydrous MeOH (125 mL) at -10° C. until saturation. The cyanopyridine from Step 2 (1.33 g, 10 mmol) was added and HCl was bubbled for another 5 minutes. The flask was sealed and the reaction allowed to stir 3 days at r.t. After carefully depressurizing the flask, water (3 mL) was added before concentrating in vacuo. The residue was diluted with EtOAc and saturated aq. NaHCO3. Extraction of the aqueous phase with EtOAc (2*) followed by washing of the organic layers with aq. NaHCO3, and brine gave upon concentration in vacuo 1.59 g (96%) of desired carbomethoxypyridine. 1H NMR (CD3 COCD3): δ 7.8 (1H, d), 7.65 (1H, d), 3.85 (3H, s), 2.5 (3H, s), 2.35 (3H, s).

Reference： [1]Current Patent Assignee: MERCK & CO INC - US5506227, 1996, A

20
[ 694-59-7 ]
aq. NH₄ Cl [ No CAS ]
[ 59146-67-7 ]
5-Ethyl-6-methyl-2-pyridinecarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.2 g (44%)	With potassium hexamethylsilazane; methyl iodide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; toluene;	Step 1 5-Ethyl-6-methyl-2-pyridinecarbonitrile Potassium bis(trimethylsilyl)amide (41 mL, 0.5M in toluene, 20.4 mmol) was added to a solution of 2-cyano-5,6-dimethylpyridine from Example 1, Step 2 (2.45 g, 18.5 mmol) and hexamethylphosphoric triamide (9.7 mL, 55.6 mmol) in dry THF (30 mL) at -78 C. After stirring 30 minutes, MeI (5.77 mL, 92.7 mmol) was added and the reaction mixture stirred 45 minutes at -78 C. Saturated aq. NH4 Cl was added, the mixture was extracted with EtOAc (3*), the organic layers were dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (from 15:15:70 to 20:20:60 of Et2 O: CH2 Cl2: hexanes) to give 1.2 g (44%) of the title compound.

Reference： [1]Patent: US5506227,1996,A

21
[ 694-59-7 ]
[ 83640-36-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; trichlorophosphate; In dichloromethane; ethyl acetate; toluene;	A solution of phosphoryl chloride (6.5 g) in dichloromethane (20 ml) was added to a mixture of the above pyridine-1-oxide (4.4 g) and triethylamine (4.3 g) in dichloromethane (60 ml). After the addition was completed the reaction mixture was gently refluxed for 15 mins, cooled and washed with water (30 ml). The organic layer was separated, dried over anhydrous sodium sulphate and evaporated to dryness. The residue was purified by flash column chromatography on silica (K60) using ethyl acetate: toluene (1:9 by volume) as eluding solvent, to give 6-chloromethylnicotinonitrile.
	With triethylamine; trichlorophosphate; In dichloromethane; ethyl acetate; toluene;	A solution of phosphoryl chloride (6.5 g) in dichloromethane (20 ml) was added to a mixture of the above pyridine-1-oxide (4.4 g) and triethylamine (4.3 g) in dichloromethane (60 ml). After the addition was completed the reaction mixture was gently refluxed for 15 mins, cooled and washed with water (30 ml). The organic layer was separated, dried over anhydrous sodium sulphate and evaporated to dryness. The residue was purified by flash column chromatography on silica (K60) using ethyl acetate: toluene (1:9 by volume) as eluding solvent, to give 6-chloromethylnicotinonitrile.

Reference： [1]Patent: US4999364,1991,A
[2]Patent: US4866086,1989,A

22
[ 694-59-7 ]
[ 13578-51-3 ]
[ 25700-17-8 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 2722 - 2725
[2]RSC Advances,2016,vol. 6,p. 58118 - 58124

23
[ 694-59-7 ]
[ 2232-08-8 ]
[ 25700-16-7 ]
[ 25700-14-5 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 2722 - 2725

24
[ 288-13-1 ]
[ 694-59-7 ]
[ 25700-11-2 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 5254 - 5257
[2]Organic Letters,2011,vol. 13,p. 1840 - 1843

25
[ 694-59-7 ]
[ 74-89-5 ]
[ 4597-87-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In tetrahydrofuran; dichloromethane at 25℃; for 15h;

Reference： [1]Londregan, Allyn T.; Jennings, Sandra; Wei, Liuqing [Organic Letters, 2010, vol. 12, # 22, p. 5254 - 5257]

26
[ 694-59-7 ]
[ 2423-65-6 ]
[ 106-38-7 ]
[ 922524-99-0 ]
[ 33421-24-8 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 8180 - 8189

27
[ 694-59-7 ]
[ 108-96-3 ]
[ 76520-27-9 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1840 - 1843

28
[ 694-59-7 ]
[ 491-30-5 ]
[ 1532-89-4 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1840 - 1843

29
[ 348640-02-8 ]
[ 694-59-7 ]
[ 1333317-11-5 ]

Reference： [1]Chemistry Letters,2011,vol. 40,p. 555 - 557

30
[ 694-59-7 ]
[ 40899-68-1 ]
2-(1-(methoxymethyl)-1H-indol-3-yl)pyridine 1-oxide [ No CAS ]

Reference： [1]Chemistry Letters,2011,vol. 40,p. 555 - 557

31
[ 694-59-7 ]
[ 131395-29-4 ]
[ 1356388-74-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	With di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; palladium diacetate; potassium carbonate; In toluene; at 140℃;Microwave irradiation; Sealed vessel;	General procedure: In either a 10-mL or an 80-mL CEM microwave vessel equipped with a teflon stir bar, an appropriate obromoacetalilide(3, 0.6 mmol in the 10-mL vessel or 3 mmol in the 80-mL vessel, 1 equiv) was added to a stirred mixture of toluene (3.3 ml/mmol 5), pyridine N-oxide (4 equiv), palladium acetate (5 mol %), di-tert-butylmethylphosphonium tetrafluoroborate (15 mol %), and anhydrous potassium carbonate (2 equiv). The mixture was sealed and heated to 140 C (110 C for compound 3h) in a CEM/Discover Benchmate single-mode microwave reactor with an external IR temperature sensor. For those procedures conducted in the 10-mL vessel, the reaction was heated to the required temperature over a period of < 5 min. For those procedures conducted in the 80-mL vessel, the reaction was heated to the required temperature stepwise over a period of 15 minutes. The reaction mixture was held at 140 C (110 C for compound 3h) for 1 hr (10-mL vessel) or 3 hr (80-mL vessel). The mixture was cooled to room temperature and filtered through a Celite pad which was washed with acetone-dichloromethane (1:1). The combined filtrate and washings were evaporated in vacuo and the residue purified by flash column chromatography on silica gel (acetone-dichloromethane mixtures) to give the product.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 612 - 615

32
[ 694-59-7 ]
[ 614-76-6 ]
[ 1356388-71-0 ]

Yield	Reaction Conditions	Operation in experiment
76%	With di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; palladium diacetate; potassium carbonate In toluene at 140℃; Microwave irradiation; Sealed vessel;	General Procedure for the Preparation of 2-(2-Acetamidoaryl)pyridine 1-Oxides (4). General procedure: In either a 10-mL or an 80-mL CEM microwave vessel equipped with a teflon stir bar, an appropriate obromoacetalilide(3, 0.6 mmol in the 10-mL vessel or 3 mmol in the 80-mL vessel, 1 equiv) was added to a stirred mixture of toluene (3.3 ml/mmol 5), pyridine N-oxide (4 equiv), palladium acetate (5 mol %), di-tert-butylmethylphosphonium tetrafluoroborate (15 mol %), and anhydrous potassium carbonate (2 equiv). The mixture was sealed and heated to 140 °C (110 °C for compound 3h) in a CEM/Discover Benchmate single-mode microwave reactor with an external IR temperature sensor. For those procedures conducted in the 10-mL vessel, the reaction was heated to the required temperature over a period of < 5 min. For those procedures conducted in the 80-mL vessel, the reaction was heated to the required temperature stepwise over a period of 15 minutes. The reaction mixture was held at 140 °C (110 °C for compound 3h) for 1 hr (10-mL vessel) or 3 hr (80-mL vessel). The mixture was cooled to room temperature and filtered through a Celite pad which was washed with acetone-dichloromethane (1:1). The combined filtrate and washings were evaporated in vacuo and the residue purified by flash column chromatography on silica gel (acetone-dichloromethane mixtures) to give the product.

Reference： [1]Myers, Jeffery T.; Hanna Jr., James M. [Tetrahedron Letters, 2012, vol. 53, # 6, p. 612 - 615]

33
[ 694-59-7 ]
[ 88284-48-4 ]
[ 33421-36-2 ]
[ 54168-07-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 6834 - 6839
[2]Organic and Biomolecular Chemistry,2012,vol. 10,p. 6834 - 6839

34
[ 694-59-7 ]
[ 88284-48-4 ]
[ 33421-36-2 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 6834 - 6839
[2]Synthesis,2015,vol. 46

35
[ 694-59-7 ]
[ 73501-39-0 ]
[ 88284-48-4 ]
[ 33421-36-2 ]
[ 54168-07-9 ]
[ 1394900-26-5 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 6834 - 6839

36
[ 694-59-7 ]
[ 217813-00-8 ]
[ 1394900-21-0 ]

Yield	Reaction Conditions	Operation in experiment
86%	With tetrabutyl ammonium fluoride In tetrahydrofuran; dichloromethane at 28℃; for 3h; Inert atmosphere; regioselective reaction;

Reference： [1]Shaibu, Balagopal S.; Kawade, Rahul Kisan; Liu, Rai-Shung [Organic and Biomolecular Chemistry, 2012, vol. 10, # 34, p. 6834 - 6839]

37
[ 694-59-7 ]
[ 20582-55-2 ]
[ 1432592-51-2 ]