55304-90-0|(2,6-Dichloropyridin-3-yl)methanol| Ambeed

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Quality Control of [ 55304-90-0 ] Purity: 95% SDS Specification

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Product Details of [ 55304-90-0 ]

CAS No. :	55304-90-0
Formula :	C₆H₅Cl₂NO
M.W :	178.02
SMILES Code :	OCC1=CC=C(Cl)N=C1Cl
MDL No. :	MFCD11036367
InChI Key :	FWEVVZQDRPWAND-UHFFFAOYSA-N
Pubchem ID :	12259932

Safety of [ 55304-90-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 55304-90-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.17
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	40.38
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	33.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.65
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.89
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.73
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.09
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.48
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.77

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.51
Solubility	0.547 mg/ml ; 0.00307 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.21
Solubility	1.1 mg/ml ; 0.00619 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.08
Solubility	0.146 mg/ml ; 0.000822 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.04 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.66

Application In Synthesis of [ 55304-90-0 ]

* 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.

Downstream synthetic route of [ 55304-90-0 ]

[ 55304-90-0 ] Synthesis Path-Downstream 1~35

1
[ 110-87-2 ]
[ 55304-90-0 ]
[ 81687-96-9 ]

References: [1]Journal of Organic Chemistry,1982,vol. 47,p. 2800 - 2802.

2
[ 55304-90-0 ]
[ 55304-73-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With Dess-Martin periodane; In dichloromethane; at 20 - 26℃; for 2.0h;	To a solution of <strong>[55304-90-0](2,6-dichloropyridin-3-yl)methanol</strong> (1.0 g, 5.62 mmol) in CH2C12 (10 ml) was added Dess-Martin reagent (4.8 g, 11.24 mmol) at 26C. After addition the mixture was stirred at room temperature for 2 h. Once the reaction was complete, the mixture was then quenched by adding 5% aqueous Na2S203 and stirred for 30 min. The resulting mixture was extracted with CH2C12 (2x30 ml). The combined organic layers were washed with saturated Na2S203 solution (50 ml), brine (30 ml), dried over Na2S04 and concentrated to give the title compound which was used in next step without further purification. (800 mg, Yield 80%). 1H NMR (400MHz, CDC13): 10.38 (s, 1H), 8.19 (d, J=8.0 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H).
66%	With pyridinium chlorochromate; In dichloromethane; for 2.0h;	Dissolve <strong>[55304-90-0](2,6-dichloropyridin-3-yl)-methanol</strong> (876 mg, 4.92 mmol) in dichloromethane (20.mL). Add pyridium chlorochromate (2.12 g, 9.84 mmol). Stir for 2 hours. Add diethyl ether and stir for 20 minutes. Filter the mixture through a pad of Celite and silica gel and concentrate to give 2,6-dichloropyridine-3-carbaldehyde (575 mg, 66%): 1H NMR (400 MHz5 CDCl3) delta 10.39 (s, IH)5 8.18 (d, IH, J = 8.0 Hz)5 7.43 (d, IH, J = 8.0 Hz).
	With manganese dioxide; In benzene;	180 g (1.01 mols) of <strong>[55304-90-0]2,6-dichloro-3-hydroxymethylpyridine</strong> are then heated under reflux for 2 hours with 600 g (6.9 mols) of manganese dioxide in 4 l of benzene. The reaction mixture is filtered while still hot and the benzene is evaporated. After drying the residue in a vacuum drying cabinet, 2,6-dichloropyridine-3-aldehyde is obtained.

References: [1]Patent: WO2014/100695,2014,A1 .Location in patent: Paragraph 00409.
[2]Journal of Organic Chemistry,1982,vol. 47,p. 2800 - 2802.
[3]Patent: WO2006/44454,2006,A1 .Location in patent: Page/Page column 62.
[4]Patent: US3974166,1976,A .

3
[ 58584-86-4 ]
[ 55304-90-0 ]

References: [1]Journal of Organic Chemistry,1982,vol. 47,p. 2800 - 2802.

5
[ 55304-73-9 ]
[ 55304-90-0 ]

Yield	Reaction Conditions	Operation in experiment
		Example 2 - Synthesis of Phantasmidine (Figure 2) 2,6-Dichloropyridine-3-pyridinemethanol (9a). A solution of 2,6- dichloropyridine-3-carboxaldehyde (8a) (950 mg, 5.40 mmol) in MeOH (10 mL) was treated with NaBH4 (205 mg, 5.40 mmol) in one portion at 0 C. The reaction was stirred at 0 C for 30 min. 10% aqueous hydrochloric acid was added dropwise to the reaction until pH 1 was reached and MeOH was removed under vacuum. The residue was extracted with CH2CI2 (50 mL x 3). The combined CH2CI2 layers were washed with H20 (50 mL) and brine (50 mL), dried (Na2S04), and concentrated to give 952 mg (99%) of 9a as a white solid, which was used directly without further purification. A small portion of crude 9a was recrystallized to give an analytical sample: mp 73-74 C (lit. 62-64 C); 1H NMR 7.88 (d, 1, J = 8.0), 7.33 (d, 1, J = 8.0), 4.78 (br s, 2), 2.21 (br s, 1, wm = 16, OH); 13C NMR 148.8, 147.8, 139.1, 133.8, 123.2, 60.9; IR 3369. The data are identical to those previously reported.
3.01 g	With methanol; sodium tetrahydroborate; at 20℃; for 0.5h;	[1037] NaBH4 (808 mg, 21.3 mmol) was added to a solution of 514-1 (3.10 g, 17.7 mmol) in MeOH (22 niL), which had been pre-cooled to 0 C. The mixture was allowed to reach r.t. and stirring was prolonged for 30 mins. 1 M aq. HC1 solution was added, and the organic solvent was removed under reduced pressure. The aqueous phase was extracted with DCM (3x). The combined organic portions were dried with and filtered. The volatiles were removed under reduced pressure to afford 514-2 (3.01 g). UPLC/MS(ES+): m/z 178.00 [M+H]+.

References: [1]Organic Letters,2011,vol. 13,p. 526 - 529.
[2]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3463 - 3468.
[3]Patent: WO2012/78608,2012,A1 .Location in patent: Page/Page column 28.
[4]Patent: WO2015/26792,2015,A1 .Location in patent: Paragraph 1037.

6
[ 55304-90-0 ]
[ 58584-60-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3463 - 3468.

7
[ 2402-78-0 ]
[ 55304-90-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3463 - 3468.

8
[ 55304-90-0 ]
[ 900505-00-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3463 - 3468.

9
[ 55304-90-0 ]
4-(2-amino-6-chloro-pyridin-3-ylmethyl)-3-(4-chloro-phenyl)-7-iodo-1-[2-(2-methoxy-ethoxy)-ethyl]-3,4-dihydro-1<i>H</i>-benzo[<i>e</i>][1,4]diazepine-2,5-dione [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3463 - 3468.

10
[ 55304-90-0 ]
[ 81688-03-1 ]

References: [1]Journal of Organic Chemistry,1982,vol. 47,p. 2800 - 2802.

11
[ 55304-90-0 ]
[ 81688-04-2 ]

References: [1]Journal of Organic Chemistry,1982,vol. 47,p. 2800 - 2802.

12
[ 55304-90-0 ]
[ 81688-05-3 ]

References: [1]Journal of Organic Chemistry,1982,vol. 47,p. 2800 - 2802.

13
[ 55304-90-0 ]
[ 81688-06-4 ]

References: [1]Journal of Organic Chemistry,1982,vol. 47,p. 2800 - 2802.

14
[ 55304-90-0 ]
[ 81687-98-1 ]

References: [1]Journal of Organic Chemistry,1982,vol. 47,p. 2800 - 2802.

15
[ 55304-90-0 ]
[ 81687-99-2 ]

References: [1]Journal of Organic Chemistry,1982,vol. 47,p. 2800 - 2802.

16
[ 55304-90-0 ]
[ 81688-00-8 ]

References: [1]Journal of Organic Chemistry,1982,vol. 47,p. 2800 - 2802.

17
[ 55304-90-0 ]
[ 81688-01-9 ]

References: [1]Journal of Organic Chemistry,1982,vol. 47,p. 2800 - 2802.

18
[ 55304-90-0 ]
[ 81688-02-0 ]

References: [1]Journal of Organic Chemistry,1982,vol. 47,p. 2800 - 2802.

19
[ 55304-90-0 ]
[ 81687-97-0 ]

References: [1]Journal of Organic Chemistry,1982,vol. 47,p. 2800 - 2802.

20
[ 55304-90-0 ]
[ 98-59-9 ]
[ 905961-62-8 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; triethylamine; In dichloromethane; at 0 - 20℃;	Synthesis of 2,6-dichloropyridin-3-yl)methyl toluenesulphonateTo a stirred solution of the compound 2,6-dichloropyridin-3-yl)methanol (0.4g, 2.25mmol), 4-dimethylaminopyridine (0.028g, 0.225 minol) and triethylamine (0.62ml, 4.5mmol) in dichloromethane (20ml) was added p-toluene sulphonyl chloride (0.64g, 3.75 mmol) portion wise at 0-5C and stirred the reaction mixture at room temperature for overnight. The mixture was diluted with dichloromethane, washed with water and brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to furnish the title compound. Yield: 0.725g.

References: [1]Patent: WO2006/85212,2006,A2 .Location in patent: Page/Page column 43.

21
[ 38496-18-3 ]
[ 55304-90-0 ]

Yield	Reaction Conditions	Operation in experiment
94%		Dissolve 2,6-dichloronicotinic acid (1000 mg, 5.21 mmol) in anhydrous tetrahydrofuran (5 niL). Cool to 0 0C. Add borane-tetrahydrofuran complex (7.82 mL5 7.82 mmol, 1.0 M in tetrahydrofuran) slowly. Stir the mixture at room temperature overnight. Add water (1 niL) and potassium carbonate, stir for 2 hours, filter and concentrate to give a residue. Chromatograph the residue on silica gel eluting with 10:90 to 20:80 ethyl acetate:hexanes to give (2,6-dichloropyridin-3-yl)-methanol (876 mg, 94%). 1H NMR (400 MHz5 MeOH-d4) delta 7.96 (d, IH, J = 8.0 Hz), 7.45 (d, IH, J = 8.0 Hz), 4.64 (s, 2H).
80%	With sodium tetrahydroborate; boron trifluoride diethyl etherate; In tetrahydrofuran; at 0 - 20℃; for 10.0h;	To a solution of 2,6-dichloronicotinic acid (1 g, 5.2 mmol) in THF (10 mL) was added NaBH4 (591 mg, 15.6 mmol) at 0C. The mixture was stirred for 30 min and then BF3.OEt2 (2.2g, 15.6 mmol) was added drop wise at 0C. After addition was complete, the mixture was stirred at room temperature for 10 hr, until the reaction was completed. The reaction mixture was quenched by the addition of saturated NH4C1 solution (50 mL) and extracted with ethyl acetate (3x30 mL). The combined organic layers were washed with brine (30 mL), dried over Na2S04 and concentrated to give the desired product as a white solid which was used in next step without further purification. (820 mg, Yield 80%).
		Synthesis of 2,6-dichloropyridin-3-yl)methanolTo a solution of the compound 2,6-dichloronicotinic acid (0.5g, 2.6mmol) in tetrahydrofuran (10ml) at 00C was added sodium borohydride (0.29g, 7.8mmol) portion wise and stirred the reaction mixture at room temperature for 30 minutes. The resulting reaction mixture was again cooled to 0C followed by the addition of etheral solution of boron trifmoride (1.1 ml, 7.8 mmole) dropwise and stirred the mixture at room temperature for overnight. The reaction mixture was quenched with aqueous sodium hydroxide (IN) and the solvent was evaporated under reduced pressure to furnish the title compound. The residue thus obtained was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to furnish the title compound. Yield: 0.44g.

In tetrahydrofuran; methanol;

PREPARATION EXAMPLE 23-1 Lithium aluminum hydride (1.78 g) was suspended in dry tetrahydrofuran (10 ml), and 2,6-dichloronicotinic acid was added under ice-cooling at an inside temperature of not more than 10 C. The mixture was stirred under ice-cooling for 1 hr and 28% aqueous amonia was added dropwise to the reaction mixture until foams disappeared. Methanol was added and the mixture was stirred at room temperature for 3 hr, and filtered through celite. The mother liquor was concentrated and the residue was applied to flash silica gel column chromatography (silica gel, 200 ml) and eluted with chloroform:ethyl acetate=8:1 to give 2,6-dichloro-3-hydroxymethylpyridine as colorless crystals (2.89 g). 1H-NMR (CDCl3): 2.11 (1H, t, J=7 Hz), 4.77 (2H, d, J=7 Hz), 7.32 (1H, d, J=8 Hz), 7.87 (1H, d, J=8 Hz). MASS (ESI): m/z 176 (M-1).

References: [1]Patent: WO2006/44454,2006,A1 .Location in patent: Page/Page column 62.
[2]Patent: WO2014/100695,2014,A1 .Location in patent: Paragraph 00408.
[3]Patent: WO2006/85212,2006,A2 .Location in patent: Page/Page column 43.
[4]Patent: US6573274,2003,B1 .

22
[ 55366-29-5 ]
[ 55304-90-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In methanol;	260 g (1.18 mols) of this 2,6-dichloro-3-acetoxymethylpyridine, 520 ml (2 mols) of aqueous 2N sodium hydroxide solution and 520 ml of methanol are heated under reflux for 2 hours. The methanol is then removed on a rotary evaporator and the residual water phase is extracted by shaking with diethyl ether. After drying the organic phase over magnesium sulphate and concentrating the solution, crude crystalline 2,6-dichloro-3-hydroxymethylpyridine is obtained, which can be purified by recrystallisation from a mixture of cyclohexane/diethyl ether.

References: [1]Patent: US3974166,1976,A .

23
[ 55304-90-0 ]
[ 18162-48-6 ]
[ 927176-32-7 ]

Yield	Reaction Conditions	Operation in experiment
	With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20℃; for 1.0h;	3 -( { [tert-butyl(dimethyl)silyl] oxy } methyl)-2,6-dichloropyridineTo a solution of (2,6-dichloropyridm-3-yl)methanol (from Step A above, 6.3g) in DMF was added imidazole (3.06 g) and t-butyldimethylsilyl chloride (6.02 g) at O0C. The mixture was warmed to room temperature and stirred for Ih before poured into water. The solution was extracted with ethyl acetate. The organic layer was washed with water (5X)5 brine, dried over MgStheta4 and concentrated. The residue was purified by silica gel (hexanes/ethyl acetate) to give the title compound (8.7 g).1HNMR (CDCl3) delta : 7.89 ( d, 1 H), 7.32 (d, 1 H), 4.74 (s, 2 H)5 0.98 (s, 9 H)5 0.16 (s, 6 H).

References: [1]Patent: WO2007/21710,2007,A1 .Location in patent: Page/Page column 73.

24
[ 58584-83-1 ]
[ 55304-90-0 ]

Yield	Reaction Conditions	Operation in experiment
		(2,6-dichloropyridin-3-yl)methanolTo a solution of 2,6-dichloronicotinic acid (1Og) in MeOH (300 mL) was added oxalyl chloride (5.5 mL) dropwise at O0C. The mixture was heated to 6O0C for a couple of hours until reaction complete. Upon concentration, the residue was dissolved in ether and added lithium aluminum hydride (2.3 g) slowly at O0C. The reaction was stirred at O0C for Ih and added water (2.3 mL) dropwise to quench excess lithium aluminum hydride. The resulting mixture was added 15% NaOH (2.3 mL) slowly, water (6.9 mL) and stirred at O0C for an additional Ih. The slush solution was filtered through celite and washed with ether. The filtrate was concentrated to give the title compound (6.5 g).1H NMR (CDCl3) delta : 7.90 ( d, 1 H)5 7.33 (d, 1 H), 4.79 (s, 2 H).

References: [1]Patent: WO2007/21710,2007,A1 .Location in patent: Page/Page column 73.

25
[ 55304-90-0 ]
[ 1261593-67-2 ]

References: [1]Organic Letters,2011,vol. 13,p. 526 - 529.
[2]Patent: WO2012/78608,2012,A1 .

26
[ 55304-90-0 ]
[ 1261593-66-1 ]

References: [1]Organic Letters,2011,vol. 13,p. 526 - 529.
[2]Patent: WO2012/78608,2012,A1 .

27
[ 55304-90-0 ]
[ 1261593-65-0 ]

References: [1]Organic Letters,2011,vol. 13,p. 526 - 529.
[2]Patent: WO2012/78608,2012,A1 .

28
[ 55304-90-0 ]
[ 41789-37-1 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride;N,N-dimethyl-formamide; In dichloromethane; at 0 - 25℃; for 6.0h;Inert atmosphere;	2,6-Dichloro-3-pyridineacetonitrile (11a). A solution of 9a (848 mg, 4.76 mmol) in 5 mL of CH2C12 was treated with 5 mL of SOCl2 and 3 drops of DMF at 0 C. The resulting solution was stirred at 0 C for 1 h and then warmed to 25 C and stirred for another 5 h. The reaction was concentrated. The residue was dissolved in 50 mL of CH2CI2and the solution was washed with saturated NaHC03 and brine, dried (Na2S04), and concentrated to give 1.02 g of crude 2,6-dichloro-3-chloromethylpyridine (10a), which was used without further purification. A small portion of crude 10a was recrystallized to give an analytical sample: mp 83-84 C; 1H NMR 7.82 (d, 1, J = 8.0), 7.33 (d, 1, J = 8.0), 4.66 (s, 2); 13C NMR 150.1, 149.5, 141.2, 130.6, 123.5, 41.8; IR 1580, 1552, 1426, 1353. The data are identical to those previously reported. A solution of crude 10a dissolved in 20 mL 9: 1 EtOH/H20 was treated with NaCN (466 mg, 9.52 mmol). The resulting solution was heated at 80 C for 4 h. The reaction was cooled and diluted with H20 (50 mL), and extracted with CH2C12 (3 x 50 mL). The combined organic layers were washed with H20 and brine and dried (Na2S04). Concentration gave 952 mg of crude 11a. Flash chromatography (5: 1 hexanes/EtOAc) gave 572 mg (64%) of pure 11a: mp 90-91 C (lit. 80-82 C, lit. 89-91 C ); 1H NMR 7.86 (d, 1, J = 8.0), 7.38 (d, 1, J = 8.0), 3.85 (s, 2); 13C NMR 150.4, 149.3, 140.2, 124.0, 123.7, 115.4, 21.4; IR 2265. The 1H NMR data are identical to those previously reported.

References: [1]Organic Letters,2011,vol. 13,p. 526 - 529.
[2]Patent: WO2012/78608,2012,A1 .Location in patent: Page/Page column 28-29.

29
[ 55304-90-0 ]
[ 58596-63-7 ]

References: [1]Organic Letters,2011,vol. 13,p. 526 - 529.
[2]Patent: WO2012/78608,2012,A1 .

30
[ 55304-90-0 ]
[ 63580-08-5 ]

References: [1]Patent: WO2012/78608,2012,A1 .

31
[ 55304-90-0 ]
[ 1616099-29-6 ]

References: [1]Patent: WO2014/100695,2014,A1 .

32
[ 55304-90-0 ]
[ 1616097-82-5 ]

References: [1]Patent: WO2014/100695,2014,A1 .

33
[ 55304-90-0 ]
C₁₂H₁₆ClNO₃ [ No CAS ]

References: [1]Patent: WO2015/26792,2015,A1 .

34
[ 55304-90-0 ]
C₁₀H₁₁BrClNO₃ [ No CAS ]

References: [1]Patent: WO2015/26792,2015,A1 .

35
[ 55304-90-0 ]
C₁₁H₁₁ClF₃NO₃ [ No CAS ]

References: [1]Patent: WO2015/26792,2015,A1 .

Historical Records

Technical Information

• Alkyl Halide Occurrence • Appel Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hydride Reductions • Jones Oxidation • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Preparation of Alcohols • Preparation of Amines • Reactions of Alcohols • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions with Organometallic Reagents • Ritter Reaction • Sharpless Olefin Synthesis • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Swern Oxidation

Related Functional Groups of
[ 55304-90-0 ]

Chlorides

A265152 [58584-94-4]

2,6-Dichloro-3-methylpyridine

Similarity: 0.86

A173260 [42330-59-6]

2-Chloro-3-pyridinylmethanol

Similarity: 0.83

A185199 [101990-69-6]

2,6-Dichloropyridine-4-methanol

Similarity: 0.81

A336484 [950746-21-1]

6,8-Dichloro-2,7-naphthyridin-1(2H)-one

Similarity: 0.81

A178574 [62774-90-7]

2,6-Dichloro-4-methylnicotinic acid

Similarity: 0.79

Alcohols

A173260 [42330-59-6]

2-Chloro-3-pyridinylmethanol

Similarity: 0.83

A185199 [101990-69-6]

2,6-Dichloropyridine-4-methanol

Similarity: 0.81

A336484 [950746-21-1]

6,8-Dichloro-2,7-naphthyridin-1(2H)-one

Similarity: 0.81

A173252 [54127-30-9]

(5,6-Dichloropyridin-3-yl)methanol

Similarity: 0.75

A221392 [131674-39-0]

1-(2-Chloropyridin-3-yl)ethanol

Similarity: 0.73

Related Parent Nucleus of
[ 55304-90-0 ]

Pyridines

A265152 [58584-94-4]

2,6-Dichloro-3-methylpyridine

Similarity: 0.86

A173260 [42330-59-6]

2-Chloro-3-pyridinylmethanol

Similarity: 0.83

A185199 [101990-69-6]

2,6-Dichloropyridine-4-methanol

Similarity: 0.81

A178574 [62774-90-7]

2,6-Dichloro-4-methylnicotinic acid

Similarity: 0.79

A297891 [55304-73-9]

2,6-Dichloro-3-formylpyridine

Similarity: 0.78

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 55304-90-0

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