[ CAS No. 1235342-53-6 ] {[proInfo.proName]}

Name: 1235342-53-6|3-(Bromomethyl)-5-methylpyridine hydrobromide|97%
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SKU: A360128
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Quality Control of [ 1235342-53-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1235342-53-6 ]

CAS No. :	1235342-53-6	MDL No. :	MFCD20921819
Formula :	C₇H₉Br₂N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CKEAZZPEMCPDPI-UHFFFAOYSA-N
M.W :	266.96	Pubchem ID :	51071982
Synonyms :

Calculated chemistry of [ 1235342-53-6 ]

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 :	52.08
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) :	-5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.75
Log Po/w (WLOGP) :	3.09
Log Po/w (MLOGP) :	2.1
Log Po/w (SILICOS-IT) :	2.81
Consensus Log Po/w :	2.15

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.61
Solubility :	0.0662 mg/ml ; 0.000248 mol/l
Class :	Soluble
Log S (Ali) :	-2.68
Solubility :	0.563 mg/ml ; 0.00211 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.67
Solubility :	0.0571 mg/ml ; 0.000214 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.9

Safety of [ 1235342-53-6 ]

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

Application In Synthesis of [ 1235342-53-6 ]

* 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 [ 1235342-53-6 ]
Downstream synthetic route of [ 1235342-53-6 ]

[ 1235342-53-6 ] Synthesis Path-Upstream 1~3

1
[ 102074-19-1 ]
[ 1235342-53-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With hydrogen bromide In water for 5 h; Reflux	Step 2.; Alcohol (10 mmol) were refluxed in 10ml HBr (40percent aq) for more than 5 hours, and monitored through TLC or LC-MS. After completed, mixture were heated in order to evaporator solvents (water and excess HBr) until the mixture became sticky. Cool the mixture, add acetone to the mixture, precipitated solid and filtered followed by drying. Yield was high to80percent.

Reference： [1] Patent: WO2012/97196, 2012, A1, . Location in patent: Page/Page column 34

2
[ 29681-45-6 ]
[ 1235342-53-6 ]

Reference： [1] Patent: WO2012/97196, 2012, A1,
[2] Heterocyclic Communications, 2015, vol. 21, # 4, p. 203 - 205

3
[ 3222-49-9 ]
[ 1235342-53-6 ]

Reference： [1] Heterocyclic Communications, 2015, vol. 21, # 4, p. 203 - 205

[ 1235342-53-6 ] Synthesis Path-Downstream 1~13

1
[ 102074-19-1 ]
[ 1235342-53-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With hydrogen bromide; In water; for 5h;Reflux;	Step 2.; Alcohol (10 mmol) were refluxed in 10ml HBr (40% aq) for more than 5 hours, and monitored through TLC or LC-MS. After completed, mixture were heated in order to evaporator solvents (water and excess HBr) until the mixture became sticky. Cool the mixture, add acetone to the mixture, precipitated solid and filtered followed by drying. Yield was high to80%.

Reference： [1]Patent: WO2012/97196,2012,A1 .Location in patent: Page/Page column 34

2
[ 29681-45-6 ]
[ 1235342-53-6 ]

Reference： [1]Patent: WO2012/97196,2012,A1
[2]Heterocyclic Communications,2015,vol. 21,p. 203 - 205
[3]Patent: CN104163786,2016,B

3
(5-methylpyridin-3-yl)methanol hydrobromide [ No CAS ]
[ 1235342-53-6 ]

Yield	Reaction Conditions	Operation in experiment
79.5%	With hydrogen bromide; In 5,5-dimethyl-1,3-cyclohexadiene;Reflux;	In a 100mL single-mouth bottle,Add the previous product 5 (5.0 g, 0.025 mol),Hydrobromic acid (50 mL, 40%, 0.34 mol)And xylene 25mL, heated to reflux,The water separator removed the water until no moisture was present, and TLC showed the reaction was complete.Evaporate under reduced pressure to remove the solvent.Obtained 8.6 g of a brown solid, added 45 ml of acetone, sonicated for 1 hour, and filtered.A white solid (5.2 g, 79.5%) was obtained.

Reference： [1]Heterocyclic Communications,2015,vol. 21,p. 203 - 205
[2]Patent: CN104163786,2016,B .Location in patent: Paragraph 0035; 0047; 0048; 0049; 0063

4
[ 3222-49-9 ]
[ 1235342-53-6 ]

Reference： [1]Heterocyclic Communications,2015,vol. 21,p. 203 - 205
[2]Patent: CN104163786,2016,B

5
[ 1235342-53-6 ]
1-methyl-N-(1-methylcyclopropyl)-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-6-sulfonamide [ No CAS ]
1-methyl-N-(1-methylcyclopropyl)-3-[(5-methyl-3-pyridyl)methyl]-2,4-dioxoquinazoline-6-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;	3-(Bromomethyl)-5-methylpyridine hydrobromide (1 :1 ) (45 mg, 0.17 mmol) was added to a solution of 1 -methyl-N-(1 -methylcyclopropyl)-2,4-dioxo-1 ,2,3,4- tetrahydroquinazoline-6-sulfonamide (50 mg, 0.160 mmol) and potassium carbonate (47 mg, 0.34 mmol) in DMF (1 mL). The reaction mixture was stirred at ambient temperature overnight. LCMS confirmed conversion to the desired product. The reaction mixture was carefully poured into dilute aqueous sodium bicarbonate (50 mL) and extracted with EtOAc (2 x 20 mL). The organic liquors were combined, washed with brine (10 mL), passed through a hydrophobic frit and evaporated to dryness. The crude product mixture was purified by prep HPLC (high pH) to give the desired product (16 mg, 0.039 mmol, 24%) as a white powder.

Reference： [1]Patent: WO2016/92326,2016,A1 .Location in patent: Paragraph 00575

6
[ 34580-20-6 ]
[ 1235342-53-6 ]
[ 110-17-8 ]
4-[1-(5-methylpyridin-3-ylmethyl)-piperidin-4-ylidene]-4,9-dihydro-1-thiabenzo[f]azulen-10-one fumarate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8.39 g		(c) mixing the compound of the formula 3 (14.74 g, 49.9 mmol) obtained in the step (b) with chloroform (320 ml) at room temperature.Stir at 60~80 rpm,After adding triethylamine (34.8 ml, 249.6 mmol), DMAP (0.61 g, 4.99 mmol), stirring was continued for 30 min.Observe that the temperature of the reaction system no longer rises.The compound of formula II (<strong>[1235342-53-6]5-methyl-3-(bromomethyl)pyridine bromide</strong>) (39.8 g, 149.7 mmol) was then slowly charged.Set 15 C,When the reaction temperature exceeds 25 C, the feeding is stopped.Continue to feed when the temperature is below 25 C.After the end of the feeding, the heating device is turned on, the temperature is raised to 35 C, the reaction is continued for 2-4 h, the reaction condition is monitored by the high-performance liquid phase until the end of the reaction, and the reaction liquid is reserved;(d) The reaction solution obtained in the step (c) is washed with 5% NaHCO3 solution (320 ml) and water (320 ml) at room temperature, dried at 50-70 C for 5-7 h, filtered and concentrated to give a concentrate. Wherein, the volume ratio of the reaction liquid, the NaHCO3 solution and the water obtained in the step (c) is 1:1:1;(e) The concentrate obtained in the step (d) is purified by a normal phase silica gel column, and the gradient is eluted (eluent: methanol-dichloromethane solution 1%-5%), and the main component is collected.Concentrated to dryness,a foamy solid, a compound of formula 2,M = 10.0 g, yield: 50.0%;(f) adding 2.90 g of fumaric acid to 250 ml of 50% ethanol in dichloromethane,Stir and dissolve to clear at 35 C.Adding 10.0 g of the compound of the formula 2 obtained in the step (e),Dissolve and filter,Concentrate to 50-60% of the total volume,Stir and cool to 28 C for 0.5 h,Stir and cool to 15 C for 0.5 h, stirring at 0-6 C for 15 h,Pumping to dry,Dry at 70 C for 5 h,Obtained light yellow solid rupatifen fumarate (the compound of formula 1),Weighed m = 8.39 g, yield: 65.1%.

Reference： [1]Patent: CN109180666,2019,A .Location in patent: Paragraph 0122; 0125-0127

7
[ 34580-13-7 ]
[ 1235342-53-6 ]
C₂₆H₂₇N₂OS⁽¹⁺⁾*Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88.2%	In ethanol; water; at 60℃;	(i) The compound of formula II (4.34 g, 16.28 mmol) was added to pure water (10 ml). 60-80 rpm, stir to dissolve to clear; add ethyl acetate (15ml), add 5% sodium bicarbonate at 5 ~ 10 C, stir, adjust the aqueous phase pH = 7-8; separate the aqueous and organic phases The aqueous phase is extracted once with ethyl acetate (15 ml), the extract is mixed with the organic phase, dried over anhydrous sodium sulfate, filtered, and the obtained solution is used; (ii) The solid ketotifen (2.01 g, 6.51 mmol) and absolute ethanol (20 ml) were added to the step (i) to obtain a solution at room temperature, and the reaction was heated, stirred at 65 C until completely clear, and then white crystals were gradually precipitated. The reaction was monitored by TLC, the reaction was carried out for 3-4 h, and the reaction was completed to obtain a reaction solution, which was used; (iii) The reaction liquid obtained in the step (ii) is naturally cooled to room temperature with stirring. After a large amount of white crystals are precipitated, the temperature is lowered to 2-6 C, left to stand for 10-15 hours, filtered, and oven dried at 60 C. A white crystal, a compound of formula I, is obtained. m = 2.93 g, yield: 88.2% (melting point: 206-209 C, ESI-MS (m/s): 415.15);The HPLC spectrum is shown in Figure 1 (see HPLC Example for Example 5).

Reference： [1]Patent: CN109134447,2019,A .Location in patent: Paragraph 0118-0130

8
[ 34580-20-6 ]
[ 1235342-53-6 ]
[ 1417545-21-1 ]

Yield	Reaction Conditions	Operation in experiment
50%		(c) The compound of the formula 3 (14.74 g, 49.9 mmol) obtained in the step (b) and chloroform (320 ml) are mixed at room temperature, stirred at 60 to 80 rpm, and then triethylamine is added ( 34.8ml, 249.6mmol), DMAP (0.61g, 4.99mmol), stirring for 30min, observing that the temperature of the reaction system is no longer increased, and then slowly feeding the compound of formula II (5-Methyl-3-(bromomethyl)pyridine bromide) (39.8 g, 149.7 mmol), set at 15 C, the reaction temperature is over 25 C, the feed is stopped, and the temperature is kept below 25 C, the feed is continued, after the end of the feed, Turn on the heating device, raise the temperature to 35 C, continue the reaction for 2-4 h, monitor the reaction condition in the high-performance liquid phase until the end of the reaction, and reserve the reaction solution; (d) The reaction solution obtained in the step (c) is washed with 5% NaHCO3 solution (320 ml) and water (320 ml) at room temperature, dried at 50-70 C for 5-7 h, filtered and concentrated to give a concentrate. Wherein, the volume ratio of the reaction liquid, the NaHCO3 solution and the water obtained in the step (c) is 1:1:1; (e) The concentrated liquid obtained in the step (d) is purified by a normal phase silica gel column, eluted with a gradient (eluent: methanol-dichloromethane solution 1%-5%), the main component is collected, and concentrated to dryness a foamy solid, a compound of formula 2, M = 10.0 g, yield: 50.0%;

Reference： [1]Patent: CN109134447,2019,A .Location in patent: Paragraph 0005; 0131; 0134-0136

9
[ 1235342-53-6 ]
3-bromomethane-5-methylpyridine-N-oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water; at 0 - 20℃; for 2h;Inert atmosphere;	An inert atmosphere N2 was passed through a 1 L three-necked round bottom flask and held.3-Bromomethyl-5-methylpyridine hydrobromide (Compound A, 20 g, 74.92 mmol) was added.Dichloromethane (200ml) and water (40g),Then, sodium hydrogencarbonate (27.1 g, 322.58 mmol) was added dropwise with stirring at 0 C.Aqueous solution (40ml)And m-CPBA (37.1g, 214.99mmol)A solution of dichloromethane (200 ml).Stir at room temperature for 2 hours.The resulting solution was extracted with 5 x 200 ml of dichloromethane.Combine the organic layers,Dry with anhydrous sodium sulfate,Concentrate in vacuo.The residue was applied to a silica gel column eluting with dichloromethane/methanol.Get 7.5g (50%)Compound B3-bromomethane-5-methylpyridine-N-oxide pale yellow solid,The test results are shown in Figure 1.

Reference： [1]Patent: CN109678841,2019,A .Location in patent: Paragraph 0051-0054; 0061-0072

10
[ 1235342-53-6 ]
C₂₆H₂₆ClN₃O [ No CAS ]

Reference： [1]Patent: CN109678841,2019,A

11
[ 64-18-6 ]
[ 1235342-53-6 ]
(5-methylpyridin-3-yl)methanol hydrobromide [ No CAS ]
CHO₂^(1-)*C₁₄H₁₇N₂O⁽¹⁺⁾*CH₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%		Add 5-methyl-3-pyridinemethanol hydrobromide to a 1 L round bottom flask (25g, 122.51 mmol, 1.00 equiv.), then add dichloromethane (500 mL) and 5-methyl-3-bromomethylpyridine hydrobromic acid salt (32.7 g, 122.49 mmol, 1.00 equiv.). The mixture was cooled to 0 to 5 C using an ice bath and stirred Triethylamine (37.1 g, 366.64 mmol, 3.00 equiv.) was added dropwise. After the addition is completed,The mixture to be reacted is obtained. Subsequently Warm up to room temperature (25 C), Stir for 16 h. The reaction system was distilled under reduced pressure to give 73 g of crude product. The above concentrate Disperse in 73mL water (1g / mL), separated and purified by preparative chromatography, the purification conditions are: the column is C18 filler, the pore diameter is 20 um; the mobile phase is water (0.1% formic acid) / acetonitrile, and the volume fraction of acetonitrile ranges from 0 to 10% for 10 minutes. finally 8.4 g of substituted product 3-hydroxymethyl-5-methyl-1-[(5-methylpyridin-3-yl)methyl]pyridine formate, Purity is 97 wt%, yield 21 wt%. The substituted products obtained during the synthesis were tested, and the test results are shown in Figures 1 to 2. The 1H NMR spectrum and MS spectrum data of the substituted product are:

Reference： [1]Patent: CN108299395,2018,A .Location in patent: Paragraph 0074-0079; 0105-0134

12
[ 1235342-53-6 ]
[ 1417545-21-1 ]
C₃₂H₃₂N₃OS⁽¹⁺⁾*Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87.5%		(i) At room temperature, mix the compound of formula II (SM, 20g, 49.9mmol) and dichloromethane (320ml) with stirring at 60-80 rpm, then add triethylamine (34.8ml, 249.6mmol) ), Continue stirring for 30 min, observe that the reaction temperature no longer rises, and then slowly feed the compound shown in formula III(5-methyl-3- (bromomethyl) pyridineBromic acidsalt)(39.8g, 149.7mmol), set 15 , stop feeding when the reaction temperature exceeds 25 , continue feeding when the temperature is below 25 , turn on the heating device after the feeding is completed, heat up to 40 , continue the reaction for 2h, hplc monitoring Response.(ii) At room temperature, the reaction solution obtained in step (i) was washed with 5% NaHCO3 solution (320ml) and water (320ml), dried at 50-70 C for 5-7h, filtered and concentrated to 1.5-1.8 g / ml, wherein the volume ratio of the reaction solution, NaHCO3 solution and water obtained in step (i) is 1: 1: 1.(iii) The concentrated solution obtained in step (ii), absolute ethanol (20ml) and diethyl ether (100ml) are heated at 80-90 C and stirred for 1h. After cooling to room temperature, the temperature is lowered to 4-8 C and maintained for 10-15h. The solid particles were precipitated, filtered and dried to obtain yellow particles with a yield of 87.5%.

Reference： [1]Patent: CN107021954,2020,B .Location in patent: Paragraph 0119-0136

13
[ 34580-20-6 ]
[ 1235342-53-6 ]
[ 6915-18-0 ]
C₂₅H₂₄N₂OS*C₄H₄O₄ [ No CAS ]

Reference： [1]Patent: CN107021954,2020,B .Location in patent: Paragraph 0113

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