[ CAS No. 2402-78-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

2D 3D

Structure of 2402-78-0 * Storage: {[proInfo.prStorage]}

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	Inquiry	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price) ]}	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ item.pr_usastock ]}		{[ item.pr_chinastock ]}	{[ item.pr_remark ]}	Login		Inquiry

Please Login or Create an Account to: See VIP prices and availability

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

For Research Only 120K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 2402-78-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 2402-78-0 ]

SDS Specification

Alternatived Products of [ 2402-78-0 ]

Product Details of [ 2402-78-0 ]

CAS No. :	2402-78-0	MDL No. :	MFCD00006244
Formula :	C₅H₃Cl₂N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FILKGCRCWDMBKA-UHFFFAOYSA-N
M.W :	147.99	Pubchem ID :	16989
Synonyms :

Calculated chemistry of [ 2402-78-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
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 :	34.26
TPSA :	12.89 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.68 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.82
Log Po/w (XLOGP3) :	2.15
Log Po/w (WLOGP) :	2.39
Log Po/w (MLOGP) :	1.68
Log Po/w (SILICOS-IT) :	2.73
Consensus Log Po/w :	2.15

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.67
Solubility :	0.319 mg/ml ; 0.00215 mol/l
Class :	Soluble
Log S (Ali) :	-2.05
Solubility :	1.31 mg/ml ; 0.00885 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.24
Solubility :	0.0859 mg/ml ; 0.000581 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.43

Safety of [ 2402-78-0 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P264-P270-P280-P301+P310+P330-P302+P352-P305+P351+P338-P332+P313-P337+P313-P405-P501	UN#:	2811
Hazard Statements:	H301-H315-H319	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 2402-78-0 ]

* 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.

Upstream synthesis route of [ 2402-78-0 ]
Downstream synthetic route of [ 2402-78-0 ]

[ 2402-78-0 ] Synthesis Path-Upstream 1~2

1
[ 2402-78-0 ]
[ 925-90-6 ]
[ 935-28-4 ]

Yield	Reaction Conditions	Operation in experiment
89%	at 0 - 20℃; Heating / reflux	A mixture of NaOH (14.7 g, 0.37 mol), hydrazine monohydrate (15 ml) and 2,6-diacetylpyridine (6g, 36.8 mmol) suspended in diethylene glycol (27 ml_) was cautiously heated to 120 °C for 16 hours. The mixture was cooled to room temperature and partitioned between H₂O and ether. The ether extracts were washed with 1 N NaOH, dried over MgSO₄ and concentrated to a clear oil. Flash column chromatography (0percent to 15percent EtOAc in hexanes) gave the product as a clear oil (2.9 g, 58percent). ¹H NMR (400 MHz, CDCI₃): 5 1.29 (t, J=7.8 Hz, 3 H), 2.80 (d, J=7.8 Hz, 2 H), 6.97 (d, J=2.0 Hz, 2 H), 7.51 (t, J=7.6 Hz, 1 H). 2,6-Diethyl-pyridine has also been prepared as follows:A solution of ethylmagnesium bromide in ethyl ether [prepared from Mg (16.5 g, 0.68 mol) and ethyl bromide (50 mL, 0.68 mol) in 500 ml_ of ether] was added dropwise to a mixture of 2,6-dichloropyridine (50 g, 0.34 mol) and NiCI₂(dppp) (1.0 g, 2 mol) in anhydrous ethyl ether(500 mL).at 0 °C unde₍r N₃ atmosphere. After addition, the resulting mixture was stirred,. , ' >.,"?, '['A V ' "' > 'ambient temperature oveifngh'tj was then heated to reflux for about 3 hours. The suspensiatonwas poured into cushed ice (200 g) and the mixture was saturated with NH₄CI. The organic layer was separated and the aqueous phase was extracted with ether (200 mL x 3). The combined organic layers were washed with water, brine, dried over Na₂SO₄ and concentrated to give the product (41 .1 g, 89percent).

Reference： [1] Synlett, 2010, # 5, p. 796 - 800
[2] Patent: WO2006/18725, 2006, A1, . Location in patent: Page/Page column 119
[3] Journal of the American Chemical Society, 2017, vol. 139, # 37, p. 13126 - 13140
[4] Journal of Organic Chemistry, 1994, vol. 59, # 18, p. 5125 - 5127
[5] Chemistry - A European Journal, 2017, vol. 23, # 7, p. 1521 - 1525

2
[ 2402-78-0 ]
[ 52764-11-1 ]

Reference： [1] Tetrahedron, 2005, vol. 61, # 6, p. 1417 - 1421

[ 2402-78-0 ] Synthesis Path-Downstream 1~13

1
[ 109-04-6 ]
[ 2402-78-0 ]
[ 13040-77-2 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 6239 - 6241

2
[ 2402-78-0 ]
[ 148493-34-9 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of diisopropyl amine (4 mL) in THF (60 mL) was added dropwise a 1.55 M n-butyl lithium/n-hexane solution (20 mL) at -78C, followed by stirring at the same temperature for 30 minutes. To this solution was added dropwise a mixture of 2,6-dichloropyridine (2.0 g) and THF (10 mL), followed by stirring at the same temperature for additional 1 hour. A mixture of triisopropyl borate (6.8 mL) and THF (10 mL) was added dropwise thereto, followed by stirring at room temperature for 20 hours. The reaction mixture was diluted with water, and then neutralized with hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and then concentrated under reduced pressure to obtain (2,6-dichloropyridin-3-yl)boronic acid (2.6 g).

Reference： [1]Tetrahedron,2005,vol. 61,p. 1417 - 1421
[2]European Journal of Organic Chemistry,2008,p. 1458 - 1463
[3]Patent: EP2177505,2010,A1 .Location in patent: Page/Page column 18

3
[ 2402-78-0 ]
[ 17997-47-6 ]
[ 13040-77-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	tetrakis(triphenylphosphine) palladium(0); In toluene; for 11h;Reflux;	Step 1 [Show Image] 2,6-dichloropyridine 11 (8.88 g, 60.0 mmol) and 2-(tributylstannyl)pyridine (7.36 g, 20.0mmol) were dissolved in toluene (74 ml). To the solution was added tetrakis triphenyl phosphinepalladium (2.31 g, 2.0 mmol) and the mixture was stirred under heat refluxing for 11 hours. The reactant was condensed under reduced pressure and the residue was purified by silica gel chromatography to give quantitatively the desired Compound 12 (3.9 g). 1H-NMR (DMSO-d6) deltapppm: 7.50-7.53 (m, 1H), 7.59 (d, 1H, J = 8.0 Hz), 7.93-8.05 (m, 2H), 8.30 (d, 1H, J = 8.0 Hz), 8.38 (d, 1H, J = 8.0 Hz), 8.72 (d, 1H, J = 4.4 Hz).
100%	tetrakis(triphenylphosphine) palladium(0); In toluene; for 11h;Reflux;	2,6-dichloropyridine 11 (8.88 g, 60.0 mmol) and 2-(tributylstannyl)pyridine (7.36 g, 20.0 mmol) were dissolved in toluene (74 ml). To the solution was added tetrakis triphenyl phosphinepalladium (2.31 g, 2.0 mmol) and the mixture was stirred under heat refluxing for 11 hours. The reactant was condensed under reduced pressure and the residue was purified by silica gel chromatography to give quantitatively the desired Compound 12 (3.9 g) 1H-NMR (DMSO-d6) ? ppm: 7.50-7.53 (m, 1H), 7.59 (d, 1H, J=8.0 Hz), 7.93-8.05 (m, 2H), 8.30 (d, 1H, J=8.0 Hz), 8.38 (d, 1H, J=8.0 Hz), 8.72 (d, 1H, J=4.4 Hz).

Reference： [1]Patent: EP2280000,2011,A1 .Location in patent: Page/Page column 34-35
[2]Patent: US2011/28468,2011,A1 .Location in patent: Page/Page column 22
[3]Organic and Biomolecular Chemistry,2007,vol. 5,p. 1397 - 1404

4
[ 2402-78-0 ]
[ 69651-48-5 ]
[ 928162-14-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 1448 - 1474

5
[ 2402-78-0 ]
[ 55304-90-0 ]

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

6
[ 2402-78-0 ]
[ 52764-11-1 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 1417 - 1421

7
[ 2402-78-0 ]
[ 62616-14-2 ]

Reference： [1]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 3658 - 3671

8
[ 2402-78-0 ]
[ 108279-89-6 ]

Reference： [1]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 3658 - 3671

9
[ 2402-78-0 ]
[ 21203-83-8 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1991,vol. 56,p. 2313 - 2325

10
[ 2402-78-0 ]
[ 74-89-5 ]
[ 89026-78-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With copper(l) iodide; In water; at 180.0℃; for 2.0h;Sealed tube; Microwave irradiation;	General procedure: Compounds I-VII (4.22 mmol), catalytic amounts of CuI (10 mg, 0.052 mmol) and water (100 muL) were treated with 6equiv of the respective amine and sealed in a 5 mL microwave vial. Pd(PPh3)4 (10 mg, 0.008 mmol) was added in the case of anilines. After the reaction was completed (see Table 1), 2 equiv of solid K2CO3 were added. The resulting product was obtained after filtration and washing with water as an analytically pure crystalline solid. Otherwise all volatiles were then evaporated and purified by flash column chromatography (A) or bulb-to-bulb distillation (B). In the case of methylamine and ethylamine the corresponding aqueous solution was used without extra water addition.
	With sodium hydroxide; In water; at 120.0℃; for 16.0h;	To a stirring solution of 2,6-dichloro-pyridine (15 g, 0.10 mol) and methylamine (40 wt %, H2O, 20 mL) in a sealed tube, NaOH (8 g, 0.20 mol) was added, the heterogeneous solution was heated at 120 C. for 16 h, the mixture was cooled down to RT before poured into 200 mL ice-H2O. After filtration, the title productproduct was collected as an off-white solid. MS m/z 143 (MH)+.
	With sodium hydroxide; In water; at 80.0℃; for 16.0h;	To a stirred solution of 2,6-dichloropyridine (1.0 g, 6.76 mmol) in methylamine (40% in water) (1.3 ml) was added NaOH (0.54 g, 13.5 mmol) at rt. The reaction mixture was heated at 80C for 16 h. The reaction mixture was cooled to rt, poured into cold water (20 ml). The obtained precipitates were collected by filtration, washed with water (15 ml) and dried under vacuum yielding 6-chloro-N- methylpyridin-2-amine (0.399 g, 2.80 mmol). This material was used for the next step without furtherpurification. LCMS: Method C, 1.82 mm, MS: ES+ 143.03; ?H NMR (400 MHz, DMSO-d6) (5ppm 7.38(dd, J=7.6 Hz, 8.0 Hz, 1 H), 6.90 (d, J4.0 Hz, 1 H), 6.48 (d, J=7.6 Hz, 1 H), 6.37 (d, J=8.4 Hz, 1 H), 2.73(d, J=4.8 Hz, 3 H).

Reference： [1]Tetrahedron,2015,vol. 71,p. 8104 - 8110
[2]Patent: US2006/69110,2006,A1 .Location in patent: Page/Page column 57
[3]Patent: WO2017/141036,2017,A1 .Location in patent: Page/Page column 51; 52

11
[ 2402-78-0 ]
[ 141-43-5 ]
[ 29449-82-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With pyridine; at 20 - 100℃;	Reference example 67: 2-(6-chloro-pyridin-2-ylaminoVethanol. 2-Arnino-ethanol (0.82 g, 13.5 mmol) was added to a solution of 2,6- dichloropyridine (2.0 g, 13.5 mmol) in pyridine (10 mL) at room temperature and then heated at 100 C overnight The reaction mixture was concentrated in vacuo to obtain a residue which was dissolved in ethyl acetate. The solution was washed with water, brine, dried over anhydrous sodium sulfate and evaporated in vacuo to afford 2-(6- chloro-pyridin-2-ylamino)-ethanol (2.3 g, 99%) as a white solid.

Reference： [1]Patent: WO2008/62182,2008,A1 .Location in patent: Page/Page column 128

12
[ 2402-78-0 ]
[ 230299-21-5 ]
[ 1451144-97-0 ]

Reference： [1]Synthesis,2013,vol. 45,p. 1837 - 1842

13
[ 2402-78-0 ]
[ 171178-33-9 ]

Reference： [1]Patent: CN110903286,2020,A

Recommend Products

Same Skeleton Products

Related Products

Isomers

Technical Information

? Alkyl Halide Occurrence ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

Historical Records

Related Functional Groups of
[ 2402-78-0 ]

Chlorides

[ 16063-69-7 ]

2,4,6-Trichloropyridine

Similarity: 0.90

[ 39621-00-6 ]

2,6-Dichloro-4-methylpyridine

Similarity: 0.88

[ 58584-94-4 ]

2,6-Dichloro-3-methylpyridine

Similarity: 0.86

[ 6515-09-9 ]

2,3,6-Trichloropyridine

Similarity: 0.84

[ 62476-56-6 ]

3-Amino-2,6-dichloropyridine

Similarity: 0.83

Related Parent Nucleus of
[ 2402-78-0 ]

Pyridines