[ CAS No. 4370-22-3 ] {[proInfo.proName]}

Name: 4370-22-3|2-(Chloromethyl)-3-methylpyridine hydrochloride|95%
Brand: Ambeed
SKU: A208343
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Limited Quantity	USD 15-60
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Inaccessible (Haz class 6.1), International	USD 150+
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Quality Control of [ 4370-22-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4370-22-3 ]

SDS Specification

Alternatived Products of [ 4370-22-3 ]

Product Details of [ 4370-22-3 ]

CAS No. :	4370-22-3	MDL No. :	MFCD07781109
Formula :	C₇H₉Cl₂N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DCKALIKGFDMDHB-UHFFFAOYSA-N
M.W :	178.06	Pubchem ID :	13058683
Synonyms :

Calculated chemistry of [ 4370-22-3 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.29
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	45.93
TPSA :	12.89 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-9.18 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	-2.53
Log Po/w (WLOGP) :	2.78
Log Po/w (MLOGP) :	1.8
Log Po/w (SILICOS-IT) :	2.77
Consensus Log Po/w :	0.96

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	3.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	0.27
Solubility :	333.0 mg/ml ; 1.87 mol/l
Class :	Highly soluble
Log S (Ali) :	2.8
Solubility :	113000.0 mg/ml ; 636.0 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-3.41
Solubility :	0.0698 mg/ml ; 0.000392 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.58

Safety of [ 4370-22-3 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P501-P260-P270-P264-P280-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405	UN#:	3261
Hazard Statements:	H302-H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 4370-22-3 ]

* 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 [ 4370-22-3 ]
Downstream synthetic route of [ 4370-22-3 ]

[ 4370-22-3 ] Synthesis Path-Upstream 1~5

1
[ 63071-09-0 ]
[ 4370-22-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With thionyl chloride In dichloromethane at 0 - 20℃; for 2.16667 h;	To a stirred solution of 2,3-lutidine (5.00 g, 46.7 mmol) in chloroform (100 mL) at 0°C was added m- chloroperbenzoic acid (12.0 g of a 77percent max reagent) portionwise over 5 min. The reaction mixture was stirred for an additional 30 min at 0°C and then allowed to warm to room temperature. After 16 h, the reaction mixture was concentrated to dryness, water (20 mL) was added and the pH of the mixture was adjusted to 8 (saturated NaHCO3). The mixture was concentrated and the residue was extracted with dichloromethane/methanol (4: 1). The extracts were concentrated to a white solid. Subsequent column purification (Si02 ; dichloromethane/methanol, 9: 1) gave 2, 3-lutidine-N-oxide as a white solid (4.80 g, 83percent). A stirred solution of 2,3-lutidine-N-oxide (4.80 g, 39.0 mmol) in acetic anhydride (50 mL) was heated under reflux overnight, cooled and then concentrated to dryness providing (2-acetoxymethyl) -3-methylpyridine as a brown oil (6.34 g). A mixture of the crude (2-acetoxymethyl)-3- methylpyridine and K2CO3 (10. 0 g, 72.4 mmol), methanol (60 mL) and water (30 mL) was stirred at room temperature overnight. The solid was filtered off and the filtrate was concentrated to dryness. The residue, after column chromatography (Si02 ; dichloromethane/methanol, 9: 1), gave (2-hydroxymethyl) -3-methylpyridine as a light brown oil (2.86 g, 59percent over 2 steps). (2-Hydroxymethyl) -3-methylpyridine: 1H NMR (CDC13) : 5 8.41 (d, J = 4.9, 1 H), 7.48 (d, J = 7.5, 1 H), 7.16 (dd, J = 4.9 and 7.5, 1 H), 4.69 (s, 2 H), 4.00 (br, 1 H), 2.22 (s, 3 H).

Reference： [1] Patent: WO2005/95360, 2005, A1, . Location in patent: Page/Page column 58; 59

2
[ 583-61-9 ]
[ 4370-22-3 ]

Reference： [1] Chemische Berichte, 1987, vol. 120, p. 649 - 652
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 23, p. 8013 - 8029

3
[ 22710-07-2 ]
[ 4370-22-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 23, p. 8013 - 8029

4
[ 52814-41-2 ]
[ 4370-22-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 23, p. 8013 - 8029

5
[ 70580-08-4 ]
[ 4370-22-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 23, p. 8013 - 8029

[ 4370-22-3 ] Synthesis Path-Downstream 1~15

1
[ 583-61-9 ]
[ 4370-22-3 ]

Reference： [1]Chemische Berichte,1987,vol. 120,p. 649 - 652
[2]Journal of Medicinal Chemistry,2011,vol. 54,p. 8013 - 8029

2
[ 74-93-1 ]
[ 4370-22-3 ]
3-methyl-2-(methylsulfanylmethyl)pyridine [ No CAS ]

Reference： [1]Journal of Molecular Structure,1995,vol. 350,p. 115 - 128

3
[ 4370-22-3 ]
C-(3-Methyl-pyridin-2-yl)-methylamine; hydrochloride [ No CAS ]
[ 202192-54-9 ]

Reference： [1]Journal of the American Chemical Society,1998,vol. 120,p. 955 - 962

4
[ 63071-09-0 ]
[ 4370-22-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With thionyl chloride; In dichloromethane; at 0 - 20℃; for 2.16667h;	To a stirred solution of 2,3-lutidine (5.00 g, 46.7 mmol) in chloroform (100 mL) at 0C was added m- chloroperbenzoic acid (12.0 g of a 77% max reagent) portionwise over 5 min. The reaction mixture was stirred for an additional 30 min at 0C and then allowed to warm to room temperature. After 16 h, the reaction mixture was concentrated to dryness, water (20 mL) was added and the pH of the mixture was adjusted to 8 (saturated NaHCO3). The mixture was concentrated and the residue was extracted with dichloromethane/methanol (4: 1). The extracts were concentrated to a white solid. Subsequent column purification (Si02 ; dichloromethane/methanol, 9: 1) gave 2, 3-lutidine-N-oxide as a white solid (4.80 g, 83%). A stirred solution of 2,3-lutidine-N-oxide (4.80 g, 39.0 mmol) in acetic anhydride (50 mL) was heated under reflux overnight, cooled and then concentrated to dryness providing (2-acetoxymethyl) -3-methylpyridine as a brown oil (6.34 g). A mixture of the crude (2-acetoxymethyl)-3- methylpyridine and K2CO3 (10. 0 g, 72.4 mmol), methanol (60 mL) and water (30 mL) was stirred at room temperature overnight. The solid was filtered off and the filtrate was concentrated to dryness. The residue, after column chromatography (Si02 ; dichloromethane/methanol, 9: 1), gave (2-hydroxymethyl) -3-methylpyridine as a light brown oil (2.86 g, 59% over 2 steps). (2-Hydroxymethyl) -3-methylpyridine: 1H NMR (CDC13) : 5 8.41 (d, J = 4.9, 1 H), 7.48 (d, J = 7.5, 1 H), 7.16 (dd, J = 4.9 and 7.5, 1 H), 4.69 (s, 2 H), 4.00 (br, 1 H), 2.22 (s, 3 H).

Reference： [1]Patent: WO2005/95360,2005,A1 .Location in patent: Page/Page column 58; 59

5
[ 5137-55-3 ]
[ 6462-50-6 ]
[ 4370-22-3 ]
4-methoxy benzenesulfonyl 2-methyl 3-methyl pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85.2%	With sodium hydrogencarbonate; In water; toluene;	a 4-methoxy benzenesulfonyl 2-methyl 3-methyl pyridine A mixture of 0.050 mole of 2-chloromethyl 3-methyl pyridine hydrochloride, 0.050 mole of sodium 4-methoxy benzenesulfinate and 0.070 mole of sodium bicarbonate in 20 ml of toluene containing 0.8 g of methyltrioctylammonium chloride is stirred at 80 C. for 2.5 hours. It is cooled, poured into 100 ml of water and extracted 3 times with 125 ml of ethyl acetate to give 17 g of a brownish paste which is purified on a column of silica (solvent: dichloromethane/ethyl acetate 5/1). In this manner, 4-methoxy benzenesulfonyl 2-methyl 3-methyl pyridine is obtained as a white solid in a yield of 85.2%. Purity: 98.9% M.p.: 84-85 C.

Reference： [1]Patent: US5444056,1995,A

6
[ 86604-73-1 ]
[ 4370-22-3 ]
2-[[(3-methyl-pyridin-2-yl)methyl]thio]-5-(trifluoromethyl)benzimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In dichloromethane; water;	(a) 6.54 g of 5-(trifluoromethyl)-2-benzimidazolethiol are suspended in 200 ml of alcohol and treated with 5.34 g of <strong>[4370-22-3]2-chloromethyl-3-methylpyridine hydrochloride</strong> while cooling wlth ice. Thereafter. a solution of 2.4 g of sodium hydroxide in 100 ml of water is added dropwise thereto, the mixture is left to boil at reflux overnight and subsequently evaporated to dryness in vacuo. The residue is dissolved in 950 ml of methylene chloride. The solution is washed firstly with 200 ml of 1.5N sodium hydroxide solution and then 3 x with 250 ml of water. dried over sodium sulphate and evaporated in vacuo. The crude product is purified on 100 g of silica gel with ethyl acetate/methylene chloride (1:1) as the elution agent. Crystallization from methylene chloride/petroleum ether gives 2-[[3-methyl-2-pyridyl)methyl]thio]-5-(trifluoromethyl)benzimidazole of melting point 180-182.

Reference： [1]Patent: US4766133,1988,A

Yield	Reaction Conditions	Operation in experiment
		...sopropanol [12.1 g (87%), m.p. 149-150 C., decomposition]. Analogously, reaction of 2-hydroxymethyl-4-methoxy-3-methylpyridine, 2-hydroxymethyl-4-methoxy-3,5-dimethylpyridine, 2-hydroxymethyl-4-methoxy-5-methylpyridine and 2-hydroxymethyl-3-methylpyridine with thionyl chloride gives 2-chloromethyl-4-methoxy-3-methylpyridine hydrochloride (m.p. 157-158 C., decomposition, from isopropanol/ether), 2-chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride [m.p. 135-136 C. (decomposition) from isopropanol/ether], 2-chloromethyl-4-methoxy-5-methylpyridine hydrochloride [m.p. 147 C., (decomposition)] and 2-chloromethyl-3-methylpyridine hydrochloride (m.p. 163-165 C.).

8
[ 22710-07-2 ]
[ 4370-22-3 ]