[ CAS No. 197007-87-7 ] (4-Bromopyridin-3-yl)methanol

Cat. No.: A602553

2D 3D

Structure of 197007-87-7 * Storage: Inert atmosphere,2-8°C

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* Storage: Inert atmosphere,2-8°C

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Quality Control of [ 197007-87-7 ]

COA NMR CNMR HPLC LC-MS

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Specification

Alternatived Products of [ 197007-87-7 ]

Product Details of [ 197007-87-7 ]

CAS No. :	197007-87-7	MDL No. :	MFCD09910219
Formula :	C₆H₆BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DDZMBVCLSZAYOT-UHFFFAOYSA-N
M.W :	188.02	Pubchem ID :	435086
Synonyms :

Safety of [ 197007-87-7 ]

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

Application In Synthesis of [ 197007-87-7 ]

* 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.

Downstream synthetic route of [ 197007-87-7 ]

[ 197007-87-7 ] Synthesis Path-Downstream 1~23

1
[ 100-39-0 ]
[ 197007-87-7 ]
[ 197007-88-8 ]

Reference： [1]Bioorganic and medicinal chemistry letters,1999,vol. 9,p. 1341 - 1346

2
[ 154105-64-3 ]
[ 197007-87-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; In ethanol; at 0℃; for 0.5h;	4-Bromo-pyridine-3-carbaldehycie (240 mg) in ethanol (10 ml_) at 0C was treated with sodium borohydride (139 mg) for 30 min. The reaction mixture was then diluted with ethyl acetate and washed with aqueous ammonium chloride and brine to yield (4-bromo-pyridin-3-yl)-methanol as a white solid.1HNMR (CDCI3, 300 MHz) delta (ppm): 10.4 (s, 1 H), 9.01 (s, 1 H), 8.56 (d, J = 5.1 Hz, 1 H), 7.63 (d, J = 5.1 Hz, 1 H).
	With sodium tetrahydroborate; In ethanol; at 0℃; for 0.5h;	4-Bromo-pyridine-3-carbaldehyde (240 mg) in ethanol (10 ml_) at 0C was treated with sodium borohydride (139 mg) for 30 min. The reaction mixture was then diluted with ethyl acetate and washed with aqueous ammonium chloride and brine to yield (4-bromo-pyridin-3-yl)-methanol as a white solid.1HNMR (CDCI3, 300 MHz) delta (ppm): 10.4 (s, 1 H), 9.01 (s, 1 H), 8.56 (d, J = 5.1 Hz, 1 H), 7.63 (d, J = 5.1 Hz, 1 H).
		Step A: (4-Bromo-3-pyridyl)methanol 0.2 g of sodium borohydride is added in portions to a solution of 1 g of 4-bromonicotinaldehyde in 50 ml of MeOH at 0 C. The whole is then stirred for 6 hours gradually returning to ambient temperature. The reaction mixture is cooled to 0 C., then hydrolyzed with a saturated NH4Cl solution and extracted with CH2Cl2. The organic phases are then combined, washed with a saturated NaCl solution, dried over magnesium sulphate and then concentrated to dryness. The title compound is obtained in the form of a light brown gel which is used as is in the following Step.

Reference： [1]Organic Letters,2008,vol. 10,p. 2701 - 2704
[2]Bioorganic and medicinal chemistry letters,1999,vol. 9,p. 1341 - 1346
[3]Patent: WO2006/91769,2006,A1 .Location in patent: Page/Page column 45
[4]Patent: WO2006/91800,2006,A2 .Location in patent: Page/Page column 45
[5]Patent: US2008/188460,2008,A1 .Location in patent: Page/Page column 13

3
[ 197007-87-7 ]
[ 216011-87-9 ]
[ 216012-93-0 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 4073 - 4076

4
[ 19524-06-2 ]
[ 197007-87-7 ]

Reference： [1]Bioorganic and medicinal chemistry letters,1999,vol. 9,p. 1341 - 1346

5
[ 197007-87-7 ]
(6aR,12bS)-10,11-Dimethoxy-5,6,6a,7,8,12b-hexahydro-3,6-diaza-benzo[c]phenanthrene [ No CAS ]

Reference： [1]Bioorganic and medicinal chemistry letters,1999,vol. 9,p. 1341 - 1346

6
[ 197007-87-7 ]
(6aR,12bS)-5,6,6a,7,8,12b-Hexahydro-3,6-diaza-benzo[c]phenanthrene-10,11-diol [ No CAS ]

Reference： [1]Bioorganic and medicinal chemistry letters,1999,vol. 9,p. 1341 - 1346

7
[ 197007-87-7 ]
(1S,2R)-1-(3-Chloromethyl-pyridin-4-yl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-ylamine [ No CAS ]

Reference： [1]Bioorganic and medicinal chemistry letters,1999,vol. 9,p. 1341 - 1346

8
[ 197007-87-7 ]
[4-((1S,2R)-2-Amino-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-pyridin-3-yl]-methanol [ No CAS ]

Reference： [1]Bioorganic and medicinal chemistry letters,1999,vol. 9,p. 1341 - 1346

9
[ 197007-87-7 ]
[4-((1S,2R)-6,7-Dimethoxy-2-nitro-1,2,3,4-tetrahydro-naphthalen-1-yl)-pyridin-3-yl]-methanol [ No CAS ]

Reference： [1]Bioorganic and medicinal chemistry letters,1999,vol. 9,p. 1341 - 1346

10
[ 197007-87-7 ]
[(1S,2R)-1-(3-Chloromethyl-pyridin-4-yl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and medicinal chemistry letters,1999,vol. 9,p. 1341 - 1346

11
[ 197007-87-7 ]
3-Benzyloxymethyl-4-((1S,2R)-6,7-dimethoxy-2-nitro-1,2,3,4-tetrahydro-naphthalen-1-yl)-pyridine [ No CAS ]

Reference： [1]Bioorganic and medicinal chemistry letters,1999,vol. 9,p. 1341 - 1346

12
[ 197007-87-7 ]
[(1S,2R)-1-(3-Hydroxymethyl-pyridin-4-yl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and medicinal chemistry letters,1999,vol. 9,p. 1341 - 1346

13
[ 197007-87-7 ]
Methanesulfonic acid 4-((1S,2R)-2-tert-butoxycarbonylamino-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-pyridin-3-ylmethyl ester [ No CAS ]

Reference： [1]Bioorganic and medicinal chemistry letters,1999,vol. 9,p. 1341 - 1346

14
[ 24964-64-5 ]
[ 197007-87-7 ]
3-{hydroxy-[3-(hydroxy-phenyl-methyl)-pyridin-4-yl]-methyl}-benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran; at -78℃; for 0.5h;	To a solution of <strong>[197007-87-7](4-bromo-pyridin-3-yl)-methanol</strong> (53 mg 0.2 mmol) in THF (2 ml_) at -78C was added dropwise 2.5 M n-butyllithium (0.24 mL, 0.6 mmol). After 15 min a solution of 3-cyanobenzaldehyde (79 mg) in THF (0.5 ml) was added. The reaction mixture was stirred for 15 min, then quenched with ammonium chloride solution and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated and the residue purified by flash chromatography to yield 3-{hydroxy-[3-(hydroxy-phenyl-methyl)-pyridin-4- yl]-methyl}-benzonitrile as white crystals.LCMS: 2.250 min, m/z: 317 (M + 1).

Reference： [1]Patent: WO2006/91769,2006,A1 .Location in patent: Page/Page column 64

15
[ 24964-64-5 ]
[ 197007-87-7 ]
3-[hydroxy-(3-hydroxymethyl-pyridin-4-yl)-methyl]-benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran; at -78℃; for 0.5h;	To a solution of <strong>[197007-87-7](4-bromo-pyridin-3-yl)-methanol</strong> (20 mg, 0.11 mmol) inTHF (1 ml_) at -78C was added dropwise 2. 5M ?-butyllithium (0.22 ml_). After 15 min, a solution of 3-cyanobenzaldehyde (69 mg) in THF (0.5 ml_) was added. The reaction mixture was stirred for 15 min, then quenched with ammonium chloride solution and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated, and the residue purified by flash chromatography to yield 3-[hydroxy-(3-hydroxymethyl-pyridin-4-yl)- methyl]-benzonitrile as a white solid.
	With n-butyllithium; In tetrahydrofuran; at -78℃; for 0.5h;	To a solution of <strong>[197007-87-7](4-bromo-pyridin-3-yl)-methanol</strong> (20 mg, 0.11 mmol) inTHF (1 mL) at -78C was added dropwise 2. 5M n-butyllithium (0.22 mL). After 15 min, a solution of 3-cyanobenzaldehyde (69 mg) in THF (0.5 mL) was added. The reaction mixture was stirred for 15 min, then quenched with ammonium chloride solution and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated, and the residue purified by flash chromatography to yield 3-[hydroxy-(3-hydroxymethyl-pyridin-4-y\|)- methyl]-benzonitrile as a white solid.

Reference： [1]Patent: WO2006/91769,2006,A1 .Location in patent: Page/Page column 63
[2]Patent: WO2006/91800,2006,A2 .Location in patent: Page/Page column 63

16
[ 150255-96-2 ]
[ 197007-87-7 ]
3-(3-hydroxymethyl-pyridin-4-yl)-benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene;Heating / reflux;	To a flask charged with (4-bromo-pyridin-3~yl)-methanol (90 mg, 0.48 mmol), 3-cyanophenylboronic acid (84.4 mg, 0.57 mmol) and tetrakis(triphenylphousphine)-palladium(0) (28 mg) was added 2 M Na2CO3 (2 mL) and toluene (3 ml_). The reaction mixture was refluxed overnight and then extracted with ethyl acetate. The organic layer was dried over sodium sulfate and purified by column chromatography to yield 3-(3-Hydroxymethyl-pyridin-4- yl)-benzonitrile as a white solid.1HNMR (CDCI3, 300 MHz) delta (ppm) 8.74 (s, 1 H), 8.60 (d, J = 4.8 Hz, 1 H), 7.9-7.2 (m, 7H), 4.62 (s, 2H), 3.34 (bs, 1 H); LCMS: 2.815 min, m/z: 211 (M + 1)
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene;Heating / reflux;	To a flask charged with <strong>[197007-87-7](4-bromo-pyridin-3-yl)-methanol</strong> (90 mg, 0.48 mmol), 3-cyanophenylboronic acid (84.4 mg, 0.57 mmol) and tetrakis(triphenylphousphine)-palladium(0) (28 mg) was added 2 M Na2COe (2 ml_) and toluene (3 ml_). The reaction mixture was refluxed overnight and then extracted with ethyl acetate. The organic layer was dried over sodium sulfate and purified by column chromatography to yield 3-(3-Hydroxymethyl-pyridin-4- yl)-benzonitrile as a white solid.1HNMR (CDCI3, 300 MHz) delta (ppm) 8.74 (s, 1 H), 8.60 (d, J= 4.8 Hz, 1 H), 7.9-7.2 (m, 7H), 4.62 (s, 2H), 3.34 (bs, 1 H); LCMS: 2.815 min, m/z: 211 (M + 1).

Reference： [1]Patent: WO2006/91769,2006,A1 .Location in patent: Page/Page column 45
[2]Patent: WO2006/91800,2006,A2 .Location in patent: Page/Page column 45

17
[ 1679-18-1 ]
[ 197007-87-7 ]
[ 1053265-80-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; at 80℃; for 18.25h;	Step B: [4-(4-Chlorophenyl)-3-pyridyl]methanol 0.335 g of Pd(Ph3)4, 0.453 g of 4-chlorophenylboronic acid and then 2.9 ml of a 2M aqueous Na2CO3 solution are added in succession to a suspension of 0.545 g of the compound of Step A in a mixture of DME/EtOH (7.5 ml/3 ml). The whole is degassed under argon for 15 minutes and then heated at 80 C. for 18 hours. The reaction mixture is then filtered at ambient temperature. The filtrate is then hydrolyzed and extracted with CH2Cl2. The organic phases are combined, washed with a saturated NaCl solution and then dried over magnesium sulphate and concentrated to dryness. The resulting solid is finally purified by chromatography over silica gel (CH2Cl2/MeOH) to yield the title compound.

Reference： [1]Patent: US2008/188460,2008,A1 .Location in patent: Page/Page column 13

18
[ 533-58-4 ]
[ 197007-87-7 ]
[ 1037830-79-7 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 2701 - 2704

19
[ 197007-87-7 ]
[ 1616102-14-7 ]

Reference： [1]Patent: WO2014/98259,2014,A1

20
[ 197007-87-7 ]
[ 74-88-4 ]
[ 1616105-25-9 ]

Yield	Reaction Conditions	Operation in experiment
84%		To a mixture solution of <strong>[197007-87-7](4-bromopyridin-3-yl)methanol</strong> (304 mg, 1.62 mmol)and tetrahydrofuran (10 mL) was added 60% sodium hydride (434 mg, 10.9 mmol) with cooling with ice. This mixture was stirred for 10 minutes with cooling with ice, subsequently heated to room temperature, and then stirred for 7 hours at the temperature. After the reaction mixture was cooled with ice, methyl iodide (0.11 mL, 1.78 mmol) was added thereto. This mixture was heated to room temperature and stirred for 7 hours at the temperature. After the mixture was cooled with ice, water (202 5 mL) was added thereto, followed by extracting with ethyl acetate. The organic layer was washed with brine, and anhydrous sodium sulfate was added to dry the layer. After anhydrous sodium sulfate was removed by filtration, the solvent was distilled off under reduced pressure and the residue was purified by flash chromatography to obtain 4-bromo-3-(methoxymethyl)pyridine (275 mg; yield, 84%).

Reference： [1]Patent: WO2014/98259,2014,A1 .Location in patent: Page/Page column 41

21
[ 197007-87-7 ]
4-((4-(tert-butyl)phenyl)ethynyl)nicotinaldehyde O-methyloxime [ No CAS ]

Reference： [1]Patent: JP2016/14016,2016,A

22
[ 197007-87-7 ]
[ 1616102-18-1 ]

Reference： [1]Patent: JP2016/14016,2016,A

23
[ 197007-87-7 ]
4-((4-(tert-butyl)phenyl)ethynyl)nicotinaldehyde oxime [ No CAS ]

Reference： [1]Patent: JP2016/14016,2016,A

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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 of Dihalides • Reactions with Organometallic Reagents • Ritter Reaction • Sharpless Olefin Synthesis • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Swern Oxidation

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H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 197007-87-7 ] (4-Bromopyridin-3-yl)methanol

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[ 197007-87-7 ] Synthesis Path-Downstream 1~23

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