[ CAS No. 23612-57-9 ] {[proInfo.proName]}

Name: 23612-57-9|2-Amino-3-hydroxymethylpyridine|97%
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Product Details of [ 23612-57-9 ]

CAS No. :	23612-57-9	MDL No. :	MFCD05663510
Formula :	C₆H₈N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FEIACFYXEWBKHU-UHFFFAOYSA-N
M.W :	124.14	Pubchem ID :	11159325
Synonyms :

Calculated chemistry of [ 23612-57-9 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	34.77
TPSA :	59.14 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.94 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.06
Log Po/w (XLOGP3) :	0.17
Log Po/w (WLOGP) :	0.01
Log Po/w (MLOGP) :	-0.34
Log Po/w (SILICOS-IT) :	0.49
Consensus Log Po/w :	0.28

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.14
Solubility :	8.91 mg/ml ; 0.0718 mol/l
Class :	Very soluble
Log S (Ali) :	-0.97
Solubility :	13.3 mg/ml ; 0.107 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.45
Solubility :	4.39 mg/ml ; 0.0354 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.17

Safety of [ 23612-57-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 23612-57-9 ]

* 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 [ 23612-57-9 ]
Downstream synthetic route of [ 23612-57-9 ]

[ 23612-57-9 ] Synthesis Path-Upstream 1~9

1
[ 23612-57-9 ]
[ 7521-41-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With manganese(IV) oxide In dichloromethane at 20℃;	Preparation Example J-4. 2-Aminopyridine-3-carbaldehyde To a mixture of (2-aminopyridin-3-yl)-methanol described in Preparation Example J-3 (130mg,1.1mmol) and dichloromethane (10mL) was added manganese dioxide (1.3g, 15mmol) at room temperature, and the solution was stirred overnight. The reaction solution was filtered through Celite pad, then, the solvent was evaporated in vacuo, and the title compound (108mg, 0.88mmol, 83percent) was obtained as a white solid. ¹H-NMR Spectrum (CDCl₃) δ (ppm): 6.75 (1 H, dd, J=4.9, 7.5Hz), 7.83 (1H, dd, J=1.9, 7.5Hz), 8.23 (1 H, dd, J=1.9, 4.9Hz), 9.86 (1 H, s).
83%	With manganese(IV) oxide In dichloromethane at 20℃;	To a mixture of (2-aminopyridin-3-yl)-methanol described in Preparation Example J-3 (130mg, 1.1mmol) and dichloromethane (10mL) was added manganese dioxide (1.3g, 15mmol) at room temperature, and the solution was stirred overnight. The reaction solution was filtered through Celite pad, then, the solvent was evaporated in vacuo, and the title compound (108mg, 0.88mmol, 83percent) was obtained as a white solid. ¹H-NMR Spectrum (CDCl₃) δ(ppm) : 6.75 (1H, dd, J=4.9, 7.5Hz), 7.83 (1H. dd, J=1.9, 7.5Hz), 8.23 (1 H, dd, J=1.9, 4.9Hz), 9.86 (1 H, s).

Reference： [1] Patent: EP1782811, 2007, A1, . Location in patent: Page/Page column 59
[2] Patent: EP1669348, 2006, A1, . Location in patent: Page/Page column 67
[3] Tetrahedron Letters, 2017, vol. 58, # 12, p. 1202 - 1206

2
[ 64-17-5 ]
[ 23612-57-9 ]
[ 13623-87-5 ]

Reference： [1] Organic Letters, 2015, vol. 17, # 16, p. 4054 - 4057

3
[ 13362-26-0 ]
[ 23612-57-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	With methanol; sodium tetrahydroborate In tetrahydrofuran at 65℃; for 0.25 h; Reflux	In a three-necked flask, 5 g of ethyl 2-aminonicotinate (0.0302 mol) and 80 mL of tetrahydrofuran were added, and the mixture was stirred13g sodium borohydride (0.2416mol) powder, stirring was continued at 65 ° C for 15min, was added dropwise 65mL of methanol, the reaction was refluxedThe reaction was complete by TLC (trichloromethane: methanol = 4: 1) and concentrated in vacuo while still hot. 40 mL of the mixture was distilled off and 1 gNaOH, hydrolyzed at 70-80 for 7-8h, the organic phase was separated, dried over anhydrous sodium sulfate and concentrated to give 2-amino-3-picolinateAlcohol (Intermediate A) Light yellow solid powder 2.7 g, m.p. 67.5-68 ° C, 75percent yield.

Reference： [1] Patent: CN104892608, 2017, B, . Location in patent: Paragraph 0040; 0041; 0047; 0048
[2] Polish Journal of Chemistry, 2003, vol. 77, # 5, p. 535 - 545
[3] Patent: US2005/20587, 2005, A1, . Location in patent: Page 17

4
[ 5345-47-1 ]
[ 23612-57-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran for 18 h; Heating / reflux Stage #2: With sodium hydroxide In tetrahydrofuran; water for 0.25 h;	To a solution of 2-aminonicotinic acid (20. 5g, 148mmol) in tetrahydrofuran (300mL) at room temperature was added lithium aluminum hydride (1. OM in tetrahydrofuran, 300mL, 300mmol) dropwise over 45 minutes. The resulting solution was heated to reflux for 18hrs. The mixture was cooled to room temperature and quenched by the sequential dropwise addition of water (11. 5mL), 15percent aqueous sodium hydroxide (11. 5mL), and water (34. 5mL). The mixture was stirred for 15min., then filtered through Celite 545. The filter pad was washed thoroughly with tetrahydrofuran (500mL) and 5percent methanol in chloroform (500mL). The combined filtrate and washings were evaporated to give 17.7g (96percent) of the title compound as a yellow waxy solid. MS (LC/MS/pos): 125.0 (M+H) +. 1H NMR (CDC13) 5 4.13 (br. s, 1H), 4.59 (s, 2H), 6.56 (m, 1H), 7.29 (d, 1H), 7.90 (d, 1H).
96%	With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 18 h; Reflux	To a suspension of 2-aminonicotinic acid (25.0 g, 0.18 mol) in THF (500 mL) was added L1AIH4 (13.7 g, 0.36 mol) portion-wise at 0 °C. The mixture was heated to reflux and stirred further for 18 hours, then cooled to rt, and quenched by the sequential drop wise addition of water (16 mL), NaOH aqueous solution (16 mL, 15percent), and water (50 mL). The resulted mixture was stirred at rt for 20 minutes, then filtered through a CELITE^®. The filter cake was washed thoroughly with THF (100 mL) and MeOH/CHCb (1/20 (v/v), 200 mL). The combined filtrates were concentrated in vacuo to give the title compound as yellow oil (21.6 g, 96percent). MS (ESI, pos. ion) m/z: 125.0 (M +1). ¹H NMR (400 MHz, CDCb): δ 3.93 (s, 2H), 4.54 (s, 2H), 5.15 (s, 1H), 6.55-6.70 (s, 1H), 7.30- 7.40 (m, 1H), 7.83-7.90 (m, 1H).
96%	With lithium aluminium tetrahydride In tetrahydrofuran for 18 h; Reflux	The compound 2 - amino-nicotinic acid (25.0 g, 0 . 18 µM) suspended in THF (500 ml) in, cooling to 0 °C, then added to the reaction solution in the LiAlH in batches₄ (13.7 G, 0 . 36 µM), heating to reflux, the reaction 18 hours, cooling to room temperature, and then sequentially dropwise adding water (16 ml), NaOH aqueous solution (16 ml, 15percent), water (50 ml) quenching the reaction, the resulting mixture stirring at room temperature 20 minutes later, for diatomite filter, the filter cake for sequentially THF (100 ml) and MeOH/CHCl₃ (1/20, 200 Ml) washing, the combined filtrate is concentrated under reduced pressure to obtain the title compound as a yellow oily matter (21.6 g, 96percent).

95%	With sodium hydroxide; LiAlH₄ In tetrahydrofuran; water	a) 2-Amino-3-(hydroxymethyl)pyridine To a stirred solution of 2-aminonicotinic acid (20 g, 145 mmole) in dry THF (200 mL) under argon was added 1.0 M LiAlH₄ in THF (300 mL, 300 mmole) carefully, portionwise, through a reflux condenser, over 4 hr. The reaction became exothermic and refluxed without external heating. After the addition was complete, the reaction was heated at reflux for an additional 16 hr, then was cooled to 0 °C and carefully quenched by sequential addition of H₂O (12 mL), 15percent NaOH in H₂O (12 mL), and H₂O (35 mL). The resulting thick suspension was stirred for 1 hr, then was filtered through a pad of celite.(R).. The filter pad was rinsed with THF (300 mL), and the filtrate was concentrated to dryness to give the title compound (17.04 g, 95percent) as a pale yellow waxy solid: LCMS (ES) m/e 125.1 (M + H)⁺; ¹H NMR (400 MHz, DMSO-d₆) δ 7.84 (dd, 1 H), 7.37 (m, 1 H), 6.53 (dd, 1 H), 5.65 (br s, 2 H), 5.16 (t, 1 H), 4.34 (d, J = 4.6 Hz, 2 H).
90%	Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux Stage #2: With water; sodium hydroxide In tetrahydrofuran at 0℃;	Step 1: 2-Amino-3-(hydroxymethyl)pyridineLithium aluminum hydride (12.4 g, 326.7 mmol) was portionwisely added to a suspension of 2-amino-3-carboxypyridine (30.0 g, 217.2 mmol) in THF (350 mL) at 0°C. Once the addition was completed, the reaction mixture was stirred at room temperature for 15 minutes and then at reflux overnight. The mixture was then cooled to 0°C and hydrolyzed by the successive addition of water (18 mL), a solution of sodium hydroxyde (18 mL) and water (30 mL) again. The resulting white suspension was filtered on Clarcel^.(R). and the cake was washed with THF (200 mL) and a mixture of CHCI₃/MeOH (250 mL, 9 : 1). After concentration to dryness of the filtrate, the title product was obtained as a yellow solid (24.2 g, 90percent).*H NMR (DMSO-c/₆, 400 MHz) : δ (ppm) : 7.84 (d, J = 4Hz, 1H), 7.37 (d, J = 7.2 Hz, 1H), 6.55-6.52 (m, 1H), 5.64 (br s, NH₂), 4.34 (s, 2H).
83%	With sodium hydroxide In tetrahydrofuran; methanol; chloroform; water	a) 2-Amino-3-(hydroxymethyl)pyridine To a solution of 2-aminonicotinic acid (20.5 g, 148.1 mmole) in THF was added lithium aluminum hydride (300 mL, 1.0 M in THF) over 30 minutes. The reaction solution was heated to reflux for 18 hrs and then was cooled to room temperature. The reaction was quenched by the sequential dropwise addition of H₂O (11.5 mL), 15percent NaOH (11.5 mL), and H₂O (34.5 mL). The mixture was stirred for 15 min, then was filtered through celite.(R)., and the filter pad was washed thoroughly with THF followed by 5percent CH₃OH/CHCl₃. The filtrate was concentrated to give the title compound (15.24 g, 83percent) as a waxy light yellow solid: MS (ES) m/e 125 (M + H)⁺.
83%	With sodium hydroxide In tetrahydrofuran; methanol; chloroform; water	a 2-Amino-3-(hydroxymethyl)pyridine To a solution of 2-aminonicotinic acid (20.5 g, 148.1 mmole) in THF was added lithium aluminum hydride (300 mL, 1.0 M in THF) over 30 minutes. The reaction solution was heated to reflux for 18 hrs and then was cooled to room temperature. The reaction was quenched by the sequential dropwise addition of H₂O (11.5 mL), 15percent NaOH (11.5 mL), and H₂O (34.5 mL). The mixture was stirred for 15 min, then was filtered through celite.(R)., and the filter pad was washed thoroughly with THF followed by 5percent CH₃OH/CHCl₃. The filtrate was concentrated to give the title compound (15.24 g, 83percent) as a waxy light yellow solid: MS (ES) m/e 125 (M+H)⁺.
0.74 g	With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 48 h; Inert atmosphere	To a suspension of 2-aminonicotinic acid (5-Si, 1.58 g, 11.45 mmol) in THF (80 mL), LAH (1M in ether, 22.9 mL, 22.9 mmol) was added slowly at 0 °C under argon with stirring. After completion of the addition, the ice bath was removed and the mixture was stirred at room temperature. Additional LAH (1M in ether, 11.4 mL) was added after 48 hours and the reaction was again cooled with an ice bath before saturated NH4C1 aqueous solution (20 mL) was added with stirring to form slurry. The organic layer was separated by decantation and the slurry was washed with EtOAc. The combined organic layer was washed with iN NaOH aqueous solution, brine, and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure to afford (2-aminopyridin-3-yl)methanol (5-S2, 0.74 g) as an off-white solid.

Reference： [1] Patent: WO2005/95391, 2005, A1, . Location in patent: Page/Page column 31-32
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 2206 - 2210
[3] Patent: WO2014/193647, 2014, A2, . Location in patent: Paragraph 0284
[4] Patent: CN104119331, 2018, B, . Location in patent: Paragraph 0836; 0838; 0839
[5] Patent: EP1226138, 2004, B1,
[6] Patent: WO2011/61214, 2011, A1, . Location in patent: Page/Page column 30
[7] Patent: EP1226138, 2004, B1,
[8] Patent: US2004/53814, 2004, A1,
[9] Patent: EP1790650, 2007, A1, . Location in patent: Page/Page column 92-93
[10] Patent: WO2013/80222, 2013, A1, . Location in patent: Page/Page column 29
[11] Patent: WO2018/160892, 2018, A1, . Location in patent: Paragraph 0897; 0898

5
[ 86847-64-5 ]
[ 23612-57-9 ]

Yield	Reaction Conditions	Operation in experiment
53%	With sodium hydroxide In water for 1.5 h; Heating / reflux	Preparation Example J-3. (2-Aminopyridin-3-yl)-methanol A mixture solution of N-(3-formylpyridin-2-yl)-2,2-dimethylpropionamide described in Preparation Example J-2 (500mg, 2.4mmol) and an aqueous solution of 5N sodium hydroxide (7mL) was refluxed for 90 minutes. After cooling, ethyl acetate and tetrahydrofuran were added for extraction, the organic layer was washed with brine, then, the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (methanol: ethyl acetate = 1: 5), and the title compound (160mg, 1.2mmol, 53percent) was obtained as a pale yellow solid. ¹H-NMR Spectrum (DMSO-d₆) δ (ppm): 4.31 (2H, s), 5.13 (1 H, brs), 5.62 (2H, s), 6.51,(1 H, dd, J=5.0, 7.3Hz), 7.34-7.36 (1 H, m), 7.81-7.82 (1 H, m).
53%	for 1.5 h; Heating / reflux	A mixture solution of N-(3-formylpyridin-2-yl)-2,2-dimethylpropionamide described in Preparation Example J-2 (500mg, 2.4mmol) and an aqueous solution of 5N sodium hydroxide (7mL) was refluxed for 90 minutes. After cooling, ethyl acetate and tetrahydrofuran were added for extraction, the organic layer was washed with brine, then, the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (methanol : ethyl acetate = 1 : 5), and the title compound (160mg, 1.2mmol, 53percent) was obtained as a pale yellow solid. ¹H-NMR Spectrum (DMSO-d₆) δ(ppm) : 4.31 (2H, s), 5.13 (1H, brs), 5.62 (2H, s), 6.51 (1 H, dd, J=5.0, 7.3Hz), 7.34-7.36 (1 H, m), 7.81-7.82 (1H, m).

Reference： [1] Patent: EP1782811, 2007, A1, . Location in patent: Page/Page column 59
[2] Patent: EP1669348, 2006, A1, . Location in patent: Page/Page column 67

6
[ 23612-57-9 ]
[ 335031-01-1 ]

Yield	Reaction Conditions	Operation in experiment
84%	With bromine In acetic acid at 20℃;	Step 2: 2-Amino-5-bromo-3-(hydroxymethyl)pyridineBromine (8.4 mL, 189.4 mmol) was added dropwise over 1 hour to a solution of 2- amino-3-(hydroxymethyl)pyridine (19.6 g, 157.8 mmol; which may be prepared as described in Dl, Step 1) in acetic acid (350 mL) at room temperature. The reaction mixture was then stirred overnight. After concentration to dryness, the residue was partitioned between a saturated solution of potassium carbonate (300 mL) and ethyl acetate (200 ml_). The aqueous layer was separated and extracted with ethyl acetate (2 x 200 ml_). The combined organic phases were washed with a saturated solution of sodium chloride (200 ml_), dried over sodium sulfate, filtered and concentrated to dryness. After trituration of the residue in pentane, the title product was obtained as a yellow solid (27.0 g, 84percent).*H NMR (DMSO-c/₆, 400 MHz) : δ (ppm) : 7.90 (d, J = 2.8 Hz, 1H), 7.53 (d, J = 2 Hz, 1H), 5.93 (br s, NH₂), 5.29 (br s, OH), 4.31 (s, 2H).
78%	With N-Bromosuccinimide In dichloromethane; chloroform	b) 2-Amino-5-bromo-3-(hydroxymethyl)pyridine To a solution of 2-amino-3-(hydroxymethyl)pyridine (13.0 g, 116.0 mmole) in CH₂Cl₂ (300 mL) at RT was added NBS (22.71 g, 127.6 mmole). After stirring at RT for 45 min the reaction solution was concentrated and the residue was dissolved in CHCl₃. The resulting suspension was filtered and the filtrate was concentrated to a dark oil. Purification on silica gel (EtOAc) afforded the title compound (78percent, 18.36 g) as a tan solid: MS (ES) m/e 204 (M + H)⁺.
78%	With N-Bromosuccinimide In dichloromethane; chloroform	b 2-Amino-5-bromo-3-(hydroxymethyl)pyridine To a solution of 2-amino-3-(hydroxymethyl)pyridine (13.0 g, 116.0 mmole) in CH₂Cl₂ (300 mL) at RT was added NBS (22.71 g, 127.6 mmole). After stirring at RT for 45 min the reaction solution was concentrated and the residue was dissolved in CHCl₃. The resulting suspension was filtered and the filtrate was concentrated to a dark oil. Purification on silica gel (EtOAc) afforded the title compound (78percent, 18.36 g) as a tan solid: MS (ES) m/e 204 (M+H)⁺.

63%

at 5 - 10℃;

S1. Acetic acid (456 g) was added to a 1 L three-necked flask at room temperature, and 2-amino-3-hydroxymethylpyridine (87 g, 1.0 eq) was added.The temperature was lowered to 5-10 ° C, and bromine (123 g, 1.1 eq) was added dropwise. After the addition was completed, the temperature was maintained, and the system was reacted for 1-2 h.After the reaction is completed, an aqueous sodium hydroxide solution is added to the reaction system, and after stirring for several minutes, sodium hydrogen sulfite is added, and suction filtration is performed.The obtained filter cake was again dispersed in water, and an aqueous sodium hydroxide solution was added until pH=8, and the system was again suction filtered.2-Amino-3-hydroxymethyl-5-bromopyridine was obtained in a yield of 63percent.

Reference： [1] Patent: WO2011/61214, 2011, A1, . Location in patent: Page/Page column 30-31
[2] Patent: EP1226138, 2004, B1,
[3] Patent: US2004/53814, 2004, A1,
[4] Journal of Medicinal Chemistry, 2003, vol. 46, # 9, p. 1627 - 1635
[5] Patent: CN108440523, 2018, A, . Location in patent: Paragraph 0028; 0030

7
[ 23612-57-9 ]
[ 335031-01-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With bromine In sodium carbonate; acetic acid	b) 2-Amino-5-bromo-3-(hydroxymethyl)pyridine To a stirred solution of 2-amino-3-(hydroxymethyl)pyridine (15.0 g, 121 mmole) in HOAc (300 mL) at RT was added bromine (6.2 mL, 121 mmole) dropwise over 1 hr. A suspension formed after approximately 15 min. After the addition, the reaction was stirred for an additional 1 hr, then was concentrated under vacuum. The residue was taken up in 1.0 M Na₂CO₃ (500 mL), and the solution was extracted with ethyl acetate (2 x 250 mL). The combined organic layers were washed with brine, dried (Na₂SO₄), and concentrated to dryness. The resulting residue was triturated with a small volume of petroleum ether, filtered and dried under vacuum to give the title compound (18.45 g, 75percent) as a beige solid: LCMS (ES) m/e 203.2 (M + H)+; ¹H NMR (400 MHz, DMSO-d₆) δ 7.89 (d, J = 2.3 Hz, 1 H), 7.52 (s, 1 H), 5.92 (br s, 2 H), 5.29 (br s, 1 H), 4.30 (s, 2 H).

Reference： [1] Patent: EP1226138, 2004, B1,

8
[ 23612-57-9 ]
[ 129686-16-4 ]

Reference： [1] Patent: WO2013/80222, 2013, A1,
[2] Patent: WO2014/193647, 2014, A2,
[3] Patent: CN104119331, 2018, B,
[4] Patent: CN108440523, 2018, A,
[5] Patent: WO2011/61214, 2011, A1,

9
[ 23612-57-9 ]
[ 443956-55-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	at 20℃; for 1 h;	To a stirred solution of (2-aminopyridin-3-yl)methanol (22.1 g, 178 mmol) in AcOH (350 mL) was added bromine (9.0 mL, 178 mol) drop wise at rt over 1 hour. The reaction mixture was stirred at rt overnight, then filtered. The filter cake was washed with MTBE (50 mL) and dried in vacuo at 60 °C for 2 hours to give the title compound as a yellow solid (37.9 g, 75percent). MS (ESI, pos. ion) m/z: 203.0 (M-80 +1).
75%	at 20℃;	The compound (2-aminopyridin-3-yl) methanol (22.1 g, 178 mmol)Was dissolved in AcOH (350 mL)Then at room temperature, to the reaction mixture was added dropwise bromine (9. OmL, 178mol),The reaction mixture was stirred overnight at room temperature. The reaction mixture was suction filtered, the filter cake was washed with MTABE (50 mL) and dried under vacuum at 60 ° C to give the title compound as a yellow solid (37.9 g, 75percent).

Reference： [1] Patent: WO2014/193647, 2014, A2, . Location in patent: Paragraph 0285
[2] Patent: CN104119331, 2018, B, . Location in patent: Paragraph 0836; 0842; 0843
[3] Patent: WO2013/80222, 2013, A1, . Location in patent: Page/Page column 29

[ 23612-57-9 ] Synthesis Path-Downstream 1~88

1
[ 23612-57-9 ]
2-amino-5-bromo-3-(bromomethyl)pyridine hydrobromide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 1627 - 1635
[2]Patent: WO2013/80222,2013,A1
[3]Patent: WO2014/193647,2014,A2
[4]Patent: CN104119331,2018,B
[5]Patent: WO2011/61214,2011,A1
[6]Patent: WO2019/177975,2019,A1

2
[ 23612-57-9 ]
[ 858431-27-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With thionyl chloride; In tetrahydrofuran; at 20℃; for 0.5h;	Thionyl chloride (12.4mL, 170mmol) was added to a 1L round bottom flask containing tetrahydrofuran (500mL). The flask was cooled in an ice-water bath and a solution of (2- aminopyridin-3-yl) methanol (17. 6g, 142mmol) in tetrahydrofuran (150mL) was added dropwise at a rate such that the temperature remained below 10C. The reaction mixture was warmed to room temperature and stirred for an additional 30 minutes. The solvent was evaporated and the residual solid was ground to a fine powder with a mortar and pestle, then dried under vacuum to give 23.2g (92%) of the title compound as a yellow powder.'H NMR (CDC13) 8 4.63 (s, 2H), 6.87 (m, 1H), 7.58 (br s, 2H), 7.85 (m, 2H).

Reference： [1]Patent: WO2005/95391,2005,A1 .Location in patent: Page/Page column 32
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2206 - 2210
[3]Journal of Medicinal Chemistry,2018,vol. 61,p. 3114 - 3125

3
[ 5345-47-1 ]
[ 23612-57-9 ]

Yield	Reaction Conditions	Operation in experiment
96%		To a solution of 2-aminonicotinic acid (20. 5g, 148mmol) in tetrahydrofuran (300mL) at room temperature was added lithium aluminum hydride (1. OM in tetrahydrofuran, 300mL, 300mmol) dropwise over 45 minutes. The resulting solution was heated to reflux for 18hrs. The mixture was cooled to room temperature and quenched by the sequential dropwise addition of water (11. 5mL), 15% aqueous sodium hydroxide (11. 5mL), and water (34. 5mL). The mixture was stirred for 15min., then filtered through Celite 545. The filter pad was washed thoroughly with tetrahydrofuran (500mL) and 5% methanol in chloroform (500mL). The combined filtrate and washings were evaporated to give 17.7g (96%) of the title compound as a yellow waxy solid. MS (LC/MS/pos): 125.0 (M+H) +. 1H NMR (CDC13) 5 4.13 (br. s, 1H), 4.59 (s, 2H), 6.56 (m, 1H), 7.29 (d, 1H), 7.90 (d, 1H).
96%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 18h;Reflux;	To a suspension of 2-aminonicotinic acid (25.0 g, 0.18 mol) in THF (500 mL) was added L1AIH4 (13.7 g, 0.36 mol) portion-wise at 0 C. The mixture was heated to reflux and stirred further for 18 hours, then cooled to rt, and quenched by the sequential drop wise addition of water (16 mL), NaOH aqueous solution (16 mL, 15%), and water (50 mL). The resulted mixture was stirred at rt for 20 minutes, then filtered through a CELITE. The filter cake was washed thoroughly with THF (100 mL) and MeOH/CHCb (1/20 (v/v), 200 mL). The combined filtrates were concentrated in vacuo to give the title compound as yellow oil (21.6 g, 96%). MS (ESI, pos. ion) m/z: 125.0 (M +1). 1H NMR (400 MHz, CDCb): delta 3.93 (s, 2H), 4.54 (s, 2H), 5.15 (s, 1H), 6.55-6.70 (s, 1H), 7.30- 7.40 (m, 1H), 7.83-7.90 (m, 1H).
96%	With lithium aluminium tetrahydride; In tetrahydrofuran; for 18h;Reflux;	The compound 2 - amino-nicotinic acid (25.0 g, 0 . 18 muM) suspended in THF (500 ml) in, cooling to 0 C, then added to the reaction solution in the LiAlH in batches4 (13.7 G, 0 . 36 muM), heating to reflux, the reaction 18 hours, cooling to room temperature, and then sequentially dropwise adding water (16 ml), NaOH aqueous solution (16 ml, 15%), water (50 ml) quenching the reaction, the resulting mixture stirring at room temperature 20 minutes later, for diatomite filter, the filter cake for sequentially THF (100 ml) and MeOH/CHCl3 (1/20, 200 Ml) washing, the combined filtrate is concentrated under reduced pressure to obtain the title compound as a yellow oily matter (21.6 g, 96%).

95%	With sodium hydroxide; LiAlH4; In tetrahydrofuran; water;	a) 2-Amino-3-(hydroxymethyl)pyridine To a stirred solution of 2-aminonicotinic acid (20 g, 145 mmole) in dry THF (200 mL) under argon was added 1.0 M LiAlH4 in THF (300 mL, 300 mmole) carefully, portionwise, through a reflux condenser, over 4 hr. The reaction became exothermic and refluxed without external heating. After the addition was complete, the reaction was heated at reflux for an additional 16 hr, then was cooled to 0 C and carefully quenched by sequential addition of H2O (12 mL), 15% NaOH in H2O (12 mL), and H2O (35 mL). The resulting thick suspension was stirred for 1 hr, then was filtered through a pad of celite. The filter pad was rinsed with THF (300 mL), and the filtrate was concentrated to dryness to give the title compound (17.04 g, 95%) as a pale yellow waxy solid: LCMS (ES) m/e 125.1 (M + H)+; 1H NMR (400 MHz, DMSO-d6) delta 7.84 (dd, 1 H), 7.37 (m, 1 H), 6.53 (dd, 1 H), 5.65 (br s, 2 H), 5.16 (t, 1 H), 4.34 (d, J = 4.6 Hz, 2 H).
90%		Step 1: 2-Amino-3-(hydroxymethyl)pyridineLithium aluminum hydride (12.4 g, 326.7 mmol) was portionwisely added to a suspension of 2-amino-3-carboxypyridine (30.0 g, 217.2 mmol) in THF (350 mL) at 0C. Once the addition was completed, the reaction mixture was stirred at room temperature for 15 minutes and then at reflux overnight. The mixture was then cooled to 0C and hydrolyzed by the successive addition of water (18 mL), a solution of sodium hydroxyde (18 mL) and water (30 mL) again. The resulting white suspension was filtered on Clarcel and the cake was washed with THF (200 mL) and a mixture of CHCI3/MeOH (250 mL, 9 : 1). After concentration to dryness of the filtrate, the title product was obtained as a yellow solid (24.2 g, 90%).*H NMR (DMSO-c/6, 400 MHz) : delta (ppm) : 7.84 (d, J = 4Hz, 1H), 7.37 (d, J = 7.2 Hz, 1H), 6.55-6.52 (m, 1H), 5.64 (br s, NH2), 4.34 (s, 2H).
83%	With sodium hydroxide; In tetrahydrofuran; methanol; chloroform; water;	a) 2-Amino-3-(hydroxymethyl)pyridine To a solution of 2-aminonicotinic acid (20.5 g, 148.1 mmole) in THF was added lithium aluminum hydride (300 mL, 1.0 M in THF) over 30 minutes. The reaction solution was heated to reflux for 18 hrs and then was cooled to room temperature. The reaction was quenched by the sequential dropwise addition of H2O (11.5 mL), 15% NaOH (11.5 mL), and H2O (34.5 mL). The mixture was stirred for 15 min, then was filtered through celite, and the filter pad was washed thoroughly with THF followed by 5% CH3OH/CHCl3. The filtrate was concentrated to give the title compound (15.24 g, 83%) as a waxy light yellow solid: MS (ES) m/e 125 (M + H)+.
83%	With sodium hydroxide; In tetrahydrofuran; methanol; chloroform; water;	a 2-Amino-3-(hydroxymethyl)pyridine To a solution of 2-aminonicotinic acid (20.5 g, 148.1 mmole) in THF was added lithium aluminum hydride (300 mL, 1.0 M in THF) over 30 minutes. The reaction solution was heated to reflux for 18 hrs and then was cooled to room temperature. The reaction was quenched by the sequential dropwise addition of H2O (11.5 mL), 15% NaOH (11.5 mL), and H2O (34.5 mL). The mixture was stirred for 15 min, then was filtered through celite, and the filter pad was washed thoroughly with THF followed by 5% CH3OH/CHCl3. The filtrate was concentrated to give the title compound (15.24 g, 83%) as a waxy light yellow solid: MS (ES) m/e 125 (M+H)+.
		To 100 mL of tetrahydrofuran solution containing 5.7 g of lithium aluminum hydride, 20 mL of tetrahydrofuran solution containing 13.8 g of 2-aminonicotinic acid was added, and heated for 2 hours under reflux. After cooling the reaction mixture back to room temperature, sodium sulfate decahydrate was slowly added until there are no bubbles, and stirred for 2 hours at room temperature. The insolubles were filtered through celite, the filtrate was concentrated under reduced pressure, and 10.7 g of (2-aminopyridin-3-yl)methanol [147-1] was obtained as a white solid.
	With lithium aluminium tetrahydride; In tetrahydrofuran; for 16h;Reflux;	(i) LAH, Dry THF, reflux, 16h; (ii) Br2, HOAc, 20-35C, 3h: (iii) 48% HBr.refhix, dimethyl malonate, CH3OH, 20-35C, 16h; (v) NaOH, CH3OH, reflux, 4h, then HC1, reflux, 16h; (vi) tert-butyl acrylate, Pd(OAc)2, P(o- tolyl)3, DIEA, DMF.Propionitrile, 90C, 16h; (vii) TFA, CH2C12 , 20-35T, 4h, then 4% dioxane. HC1, 20-35C, 2h. (Reference for Step-(i): WO 2005095391 and Step-(ii-vii): J. Med. Chem. 2003, 46, 1627-1635)
0.74 g	With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; at 0 - 20℃; for 48h;Inert atmosphere;	To a suspension of 2-aminonicotinic acid (5-Si, 1.58 g, 11.45 mmol) in THF (80 mL), LAH (1M in ether, 22.9 mL, 22.9 mmol) was added slowly at 0 C under argon with stirring. After completion of the addition, the ice bath was removed and the mixture was stirred at room temperature. Additional LAH (1M in ether, 11.4 mL) was added after 48 hours and the reaction was again cooled with an ice bath before saturated NH4C1 aqueous solution (20 mL) was added with stirring to form slurry. The organic layer was separated by decantation and the slurry was washed with EtOAc. The combined organic layer was washed with iN NaOH aqueous solution, brine, and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure to afford (2-aminopyridin-3-yl)methanol (5-S2, 0.74 g) as an off-white solid.

Reference： [1]Patent: WO2005/95391,2005,A1 .Location in patent: Page/Page column 31-32
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2206 - 2210
[3]Patent: WO2014/193647,2014,A2 .Location in patent: Paragraph 0284
[4]Patent: CN104119331,2018,B .Location in patent: Paragraph 0836; 0838; 0839
[5]Patent: EP1226138,2004,B1
[6]Patent: WO2011/61214,2011,A1 .Location in patent: Page/Page column 30
[7]Patent: EP1226138,2004,B1
[8]Patent: US2004/53814,2004,A1
[9]Patent: EP1790650,2007,A1 .Location in patent: Page/Page column 92-93
[10]Patent: WO2013/80222,2013,A1 .Location in patent: Page/Page column 29
[11]Patent: WO2018/160892,2018,A1 .Location in patent: Paragraph 0897; 0898

4
[ 23612-57-9 ]
[ 7521-41-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With manganese(IV) oxide; In dichloromethane; at 20℃;	Preparation Example J-4. 2-Aminopyridine-3-carbaldehyde To a mixture of (2-aminopyridin-3-yl)-methanol described in Preparation Example J-3 (130mg,1.1mmol) and dichloromethane (10mL) was added manganese dioxide (1.3g, 15mmol) at room temperature, and the solution was stirred overnight. The reaction solution was filtered through Celite pad, then, the solvent was evaporated in vacuo, and the title compound (108mg, 0.88mmol, 83%) was obtained as a white solid. 1H-NMR Spectrum (CDCl3) delta (ppm): 6.75 (1 H, dd, J=4.9, 7.5Hz), 7.83 (1H, dd, J=1.9, 7.5Hz), 8.23 (1 H, dd, J=1.9, 4.9Hz), 9.86 (1 H, s).
83%	With manganese(IV) oxide; In dichloromethane; at 20℃;	To a mixture of (2-aminopyridin-3-yl)-methanol described in Preparation Example J-3 (130mg, 1.1mmol) and dichloromethane (10mL) was added manganese dioxide (1.3g, 15mmol) at room temperature, and the solution was stirred overnight. The reaction solution was filtered through Celite pad, then, the solvent was evaporated in vacuo, and the title compound (108mg, 0.88mmol, 83%) was obtained as a white solid. 1H-NMR Spectrum (CDCl3) delta(ppm) : 6.75 (1H, dd, J=4.9, 7.5Hz), 7.83 (1H. dd, J=1.9, 7.5Hz), 8.23 (1 H, dd, J=1.9, 4.9Hz), 9.86 (1 H, s).
	With manganese(IV) oxide; In dichloromethane; at 20℃; for 18h;	General procedure: To a solution of 2-aminobenzyl alcohol (1.0 mmol, 1.00 equiv) and MnO2 (3.0 equiv.) in dry CH2Cl2 (20 mL) were stirred for 18 h at room temperature. The completion of reaction was monitored by TLC analysis. After the completion of reaction solvent was evaporated under reduced pressure at 40C and taken up for next step without any purification. 50 mL of methanol was added to same round bottom flask and corresponding aryl amines (1.0 equiv.), isocyanides (1.0 equiv.) and pTSA (15 mol%) added sequentially and the reaction mixture was stirred at room temperature for 12-15h. After the completion of reaction (monitored by TLC), the solvent of reaction mixture was evaporated under reduced pressure at 45oC to afford a black residue which was purified by column chromatography on silica gel (230-400 mesh) by eluting with gradient solution of hexane/EtOAc to get pure compound.

Reference： [1]Patent: EP1782811,2007,A1 .Location in patent: Page/Page column 59
[2]Patent: EP1669348,2006,A1 .Location in patent: Page/Page column 67
[3]Tetrahedron Letters,2017,vol. 58,p. 1202 - 1206

5
[ 86847-64-5 ]
[ 23612-57-9 ]

Yield	Reaction Conditions	Operation in experiment
85%		S3. 2-Pentylamino-3-pyridinecarboxaldehyde (200 g, 1.0 eq) at room temperatureSoluble in absolute ethanol (780g), cool down to 0-5 C,Sodium borohydride (11 g, 0.3 eq) was added in portions, after the addition was completed.The reaction system is warmed to 20-25 C, and the system reacts for 1-2 h;After all the raw materials have been reacted, the temperature is lowered again to 0-5 C.A 40% aqueous solution of sodium hydroxide (38.8 g, 1 eq) was slowly added dropwise to the reaction system, and after completion of the dropwise addition, the mixture was heated to 80-85 C for 1-2 h.After the reaction is over, cool down to 10-15 C.The pH was adjusted to pH 8 with 2.5 mol/L hydrochloric acid, and the system was concentrated to dryness.Extract with dichloromethane, separate the organic phase, and extract the aqueous phase with dichloromethane.The organic phases are combined and concentrated until a large amount of solids precipitates.The concentration was stopped by direct filtration to give 2-amino-3-hydroxymethylpyridine in a yield of 85%.
53%	With sodium hydroxide; In water; for 1.5h;Heating / reflux;	Preparation Example J-3. (2-Aminopyridin-3-yl)-methanol A mixture solution of N-(3-formylpyridin-2-yl)-2,2-dimethylpropionamide described in Preparation Example J-2 (500mg, 2.4mmol) and an aqueous solution of 5N sodium hydroxide (7mL) was refluxed for 90 minutes. After cooling, ethyl acetate and tetrahydrofuran were added for extraction, the organic layer was washed with brine, then, the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (methanol: ethyl acetate = 1: 5), and the title compound (160mg, 1.2mmol, 53%) was obtained as a pale yellow solid. 1H-NMR Spectrum (DMSO-d6) delta (ppm): 4.31 (2H, s), 5.13 (1 H, brs), 5.62 (2H, s), 6.51,(1 H, dd, J=5.0, 7.3Hz), 7.34-7.36 (1 H, m), 7.81-7.82 (1 H, m).
53%	With sodium hydroxide; water; for 1.5h;Heating / reflux;	A mixture solution of N-(3-formylpyridin-2-yl)-2,2-dimethylpropionamide described in Preparation Example J-2 (500mg, 2.4mmol) and an aqueous solution of 5N sodium hydroxide (7mL) was refluxed for 90 minutes. After cooling, ethyl acetate and tetrahydrofuran were added for extraction, the organic layer was washed with brine, then, the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (methanol : ethyl acetate = 1 : 5), and the title compound (160mg, 1.2mmol, 53%) was obtained as a pale yellow solid. 1H-NMR Spectrum (DMSO-d6) delta(ppm) : 4.31 (2H, s), 5.13 (1H, brs), 5.62 (2H, s), 6.51 (1 H, dd, J=5.0, 7.3Hz), 7.34-7.36 (1 H, m), 7.81-7.82 (1H, m).

Reference： [1]Patent: CN108675954,2018,A .Location in patent: Paragraph 0032; 0038; 0039; 0054
[2]Patent: EP1782811,2007,A1 .Location in patent: Page/Page column 59
[3]Patent: EP1669348,2006,A1 .Location in patent: Page/Page column 67

6
[ 21278-94-4 ]
[ 23612-57-9 ]
1-(3-Hydroxy-pyridin-2-yl)-3-(2-pyridin-4-yl-thiazol-4-yl)-urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene;	EXAMPLE 230 1-(3-Hydroxy-pyridin-2-yl)-3-(2-pyridin-4-yl-thiazol-4-yl)-urea 2-(4-Pyridinyl)-4-thiazolcarbonylazide (200 mg, 0.86 mmol) and <strong>[23612-57-9]2-amino-3-hydroxymethylpyridine</strong> (95 mg, 0.86 mmol) in dry toluene (10 mL) were heated at 100 C. for 12 h to give a pale yellow solid which was recrystallized from CHCl3/MeOH (99:5) to give a pale yellow solid. MS m/z: 314.0 (M+H). Calc'd for C14H11N5O2S-313.34.

Reference： [1]Patent: US6645990,2003,B2

7
[ 288-32-4 ]
[ 23612-57-9 ]
[ 18162-48-6 ]
3-[[dimethyl(1,1-dimethylethyl)silyloxy]methyl]-2-pyridinamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11.1 parts (93.1%)	In water; N,N-dimethyl-formamide;	a) To a solution of 6.2 parts of 2-amino-3-pyridinemethanol in 23.5 parts of N,N-dimethylformamide there were added 6.8 parts of 1H-imidazole and 7.5 parts of chlorodimethyl(1,1-dimethylethyl)silane. The whole was cooled for 10 min in an ice-bath and was stirred overnight at room temperature. The reaction mixture was diluted with 100 parts of water and the product was extracted with 1,1'-oxybisethane (2x). The combined extracts were washed with water and NaCl (sat.), dried, filtered and evaporated, yielding 11.1 parts (93.1%) of 3-[[dimethyl(1,1-dimethylethyl)silyloxy]methyl]-2-pyridinamine (interm. 1).

Reference： [1]Patent: US5482943,1996,A

8
[ 79099-07-3 ]
[ 23612-57-9 ]
[ 1230870-99-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium; In tetrahydrofuran; methanol;	Step 2. The product from Step 1 and 1-(tert-butyloxycarbonyl)piperidin-4-one are heated together in a solvent such as THF or methanol. The cooled mixture is treated with sodium cyanpborohydride to give 1-(tert-butyloxycarbonyl)-4-(3-hydroxymethyl-2-pyridylamino) piperidine.

Reference： [1]Patent: US5665719,1997,A

9
[ 23612-57-9 ]
[ 70-11-1 ]
2-[[(2-phenylimidazo[1,2-a]pyridin-8-yl)methyl]thio]-1H-benzimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;	EXAMPLE 26 2-[[(2-phenylimidazo[1,2-a]pyridin-8-yl)methyl]thio]-1H-benzimidazole STR35 A mixture of 1.24 g (10 mmole) of 3-hydroxymethyl-2-pyridinamine and 2.0 g (10 mmole) of alpha-bromoacetophenone in 25 ml of ethanol was stirred at room temperature. After 18 hours the resultant solid was collected, washed with ethano, and dissolved in water. The solution was made basic with aqueous potassium carbonate and extracted with dichloromethane.

Reference： [1]Patent: US4687775,1987,A

10
[ 111477-35-1 ]
[ 23612-57-9 ]
8-hydroxymethyl-2-(4-nitrophenyl)imidazo[1,2-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of 1.98 g (15 mmole) of 3-hydroxymethyl-2-pyridinamine and 3.9 g (15 mmole) of 2-bromo-2-(4-nitrophenyl)acetaldehyde was warmed to initiate an exothermic reactiion. After cooling, the mixture was shaken with aqueous potassium carbonate and dichloromethane. The solid was collected, washed with water and dichloromethane, and air dried to yield 2.84 g of 8-hydroxymethyl-2-(4-nitrophenyl)imidazo[1,2-a]pyridine, as confirmed by the nmr and infrared spectra.

Reference： [1]Patent: US4687775,1987,A

11
[ 107-20-0 ]
[ 23612-57-9 ]
[ 111477-17-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In ethanol;	EXAMPLE 6 2-[(imidazo[1,2-a]pyridin-8-ylmethyl)thio]-5-methoxy-1H-benzimidazole STR15 A mixture of 2.92 g (23 mmole) of 3-hydroxymethyl-2-pyridinamine, 6.15 g (35 mmole) of chloroacetaldehyde, and 2.0 g (35 mmole) of sodium bicarbonate in 100 ml of ethanol was heated at reflux for 1.5 hours. The mixture was filtered and the filtrate was concentrated in vacuo to a solid. Recrystallization from diethyl ether yielded 4.4 g of 8-hydroxymethylimidazo[1,2-a]pyridine, as confirmed by the nmr and infrared spectra.

Reference： [1]Patent: US4687775,1987,A

12
[ 23612-57-9 ]
[ 155412-18-3 ]
[ 916800-07-2 ]

Yield	Reaction Conditions	Operation in experiment
57%	In ethanol; at 80℃; for 10h;	Compound 2B: (3-CycloheptylH-imidazo[1,2-a]pyridin-8-yl)methanol To a solution of (2-aminopyridin-3-yl)methanol (185 mg, 1.5 mmol) in 5 mL of anhydrous ethanol was added compound 2A (250 mg, 1.1 mmol) at RT. The reaction mixture was heated at 80 C. for 10 hr, cooled to RT and then concentrated under reduced pressure to yield a residue. The residue was diluted with ethyl acetate, washed with water, dried over Na2SO4 and concentrated to yield crude material. The crude material was purified via silica gel chromatography using 30-50% ethyl acetate in hexanes to provide compound 2B (160 mg, 57%) as a white solid. HPLC Rt (Method A): 1.76 min. LC/MS (m/z)=245 (M+H)+.

Reference： [1]Patent: US2006/281750,2006,A1 .Location in patent: Page/Page column 27

13
[ 23612-57-9 ]
Petroleum ether [ No CAS ]
[ 335031-01-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With bromine; In sodium carbonate; acetic acid;	b) 2-Amino-5-bromo-3-(hydroxymethyl)pyridine To a stirred solution of <strong>[23612-57-9]2-amino-3-(hydroxymethyl)pyridine</strong> (15.0 g, 121 mmole) in HOAc (300 mL) at RT was added bromine (6.2 mL, 121 mmole) dropwise over 1 hr. A suspension formed after approximately 15 min. After the addition, the reaction was stirred for an additional 1 hr, then was concentrated under vacuum. The residue was taken up in 1.0 M Na2CO3 (500 mL), and the solution was extracted with ethyl acetate (2 x 250 mL). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated to dryness. The resulting residue was triturated with a small volume of petroleum ether, filtered and dried under vacuum to give the title compound (18.45 g, 75%) as a beige solid: LCMS (ES) m/e 203.2 (M + H)+; 1H NMR (400 MHz, DMSO-d6) delta 7.89 (d, J = 2.3 Hz, 1 H), 7.52 (s, 1 H), 5.92 (br s, 2 H), 5.29 (br s, 1 H), 4.30 (s, 2 H).

Reference： [1]Patent: EP1226138,2004,B1

14
[ 1224708-12-6 ]
[ 23612-57-9 ]
[ 1224709-05-0 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 4755 - 4758

15
[ 23612-57-9 ]
[ 709649-95-6 ]

Reference： [1]Patent: WO2011/61214,2011,A1

16
[ 23612-57-9 ]
[ 709649-96-7 ]

Reference： [1]Patent: WO2011/61214,2011,A1

17
[ 23612-57-9 ]
[ 709649-93-4 ]

Reference： [1]Patent: WO2011/61214,2011,A1

18
[ 23612-57-9 ]
[ 709650-04-4 ]

Reference： [1]Patent: WO2013/80222,2013,A1
[2]Patent: WO2011/61214,2011,A1

19
[ 23612-57-9 ]
[ 527758-07-2 ]

Reference： [1]Patent: WO2013/80222,2013,A1
[2]Patent: WO2011/61214,2011,A1

20
[ 23612-57-9 ]
[ 709650-53-3 ]

Reference： [1]Patent: WO2011/61214,2011,A1

21
[ 23612-57-9 ]
[ 709650-54-4 ]

Reference： [1]Patent: WO2011/61214,2011,A1

22
[ 23612-57-9 ]
[ 709650-52-2 ]

Reference： [1]Patent: WO2011/61214,2011,A1

23
[ 23612-57-9 ]
[ 129686-16-4 ]

Reference： [1]Patent: WO2013/80222,2013,A1
[2]Patent: WO2014/193647,2014,A2
[3]Patent: CN104119331,2018,B
[4]Patent: CN108440523,2018,A
[5]Patent: WO2011/61214,2011,A1

24
[ 23612-57-9 ]
(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid hydrochloride [ No CAS ]

Reference： [1]Patent: WO2013/80222,2013,A1
[2]Patent: WO2011/61214,2011,A1

25
[ 23612-57-9 ]
[ 941604-37-1 ]

Reference： [1]Patent: WO2013/80222,2013,A1
[2]Patent: WO2011/61214,2011,A1
[3]Patent: WO2011/61214,2011,A1

26
[ 23612-57-9 ]
[ 941604-55-3 ]

Reference： [1]Patent: WO2011/61214,2011,A1
[2]Patent: WO2011/61214,2011,A1

27
[ 23612-57-9 ]
[ 335031-10-2 ]

Reference： [1]Patent: WO2013/80222,2013,A1
[2]Patent: WO2014/193647,2014,A2
[3]Patent: CN104119331,2018,B
[4]Patent: WO2011/61214,2011,A1

28
[ 23612-57-9 ]
[ 1309205-56-8 ]

Reference： [1]Patent: WO2011/61214,2011,A1

29
[ 23612-57-9 ]
[ 1309205-57-9 ]

Reference： [1]Patent: WO2011/61214,2011,A1

30
[ 23612-57-9 ]
[ 1309205-58-0 ]

Reference： [1]Patent: WO2011/61214,2011,A1

31
[ 23612-57-9 ]
6-{(1E)-3-[3-(benzyloxy)azetidin-1-yl]-3-oxoprop-1-en-1-yl}-3 4-dihydro-1,8-naphthyridin-2(1H)-one [ No CAS ]

Reference： [1]Patent: WO2011/61214,2011,A1

32
[ 23612-57-9 ]
[ 1309205-65-9 ]

Reference： [1]Patent: WO2011/61214,2011,A1

33
[ 23612-57-9 ]
[ 1309205-66-0 ]

Reference： [1]Patent: WO2011/61214,2011,A1

34
[ 23612-57-9 ]
6-{(1E)-3-[3-([(1E)-1-methyl-2-pyrimidin-2-ylethylidene]amino}oxy)azetidin-1-yl]-3-oxoprop-1-en-1-yl}-3,4-dihydro-1,8-naphthyridin-2(1H)-one [ No CAS ]

Reference： [1]Patent: WO2011/61214,2011,A1

35
[ 23612-57-9 ]
[ 1309205-71-7 ]

Reference： [1]Patent: WO2011/61214,2011,A1

36
[ 23612-57-9 ]
[ 1309205-73-9 ]

Reference： [1]Patent: WO2011/61214,2011,A1

37
[ 23612-57-9 ]
[ 1309205-74-0 ]

Reference： [1]Patent: WO2011/61214,2011,A1

38
[ 23612-57-9 ]
[ 1309205-75-1 ]

Reference： [1]Patent: WO2011/61214,2011,A1

39
[ 23612-57-9 ]
[ 1309207-59-7 ]

Reference： [1]Patent: WO2011/61214,2011,A1

40
[ 23612-57-9 ]
[ 1309207-60-0 ]

Reference： [1]Patent: WO2011/61214,2011,A1

41
[ 23612-57-9 ]
[ 1309205-78-4 ]
[ 1309205-81-9 ]

Reference： [1]Patent: WO2011/61214,2011,A1

42
[ 23612-57-9 ]
[ 1309351-04-9 ]

Reference： [1]Patent: WO2011/61214,2011,A1

43
[ 23612-57-9 ]
[ 1309207-62-2 ]

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44
[ 23612-57-9 ]
[ 1309205-82-0 ]

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45
[ 23612-57-9 ]
[ 1309205-83-1 ]

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46
[ 23612-57-9 ]
[ 1309205-86-4 ]

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47
[ 23612-57-9 ]
6-[3-(3-(4-methylthiophen-2ylmethoxy)azetidin-1-yl)-3-oxopropenyl]-3,4-dihydro-1H-[1,8]naphthyridin-2-one [ No CAS ]

Reference： [1]Patent: WO2011/61214,2011,A1

48
[ 23612-57-9 ]
[ 1309205-90-0 ]

Reference： [1]Patent: WO2011/61214,2011,A1

49
[ 23612-57-9 ]
(E)-6-[3-((2-methoxyethoxy)azetidin-1-yl)-3-oxoprop-1-enyl]-3,4-dihydro-1,8-naphthyridin-2(1H)-one [ No CAS ]

Reference： [1]Patent: WO2011/61214,2011,A1

50
[ 23612-57-9 ]
[ 1309205-94-4 ]

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51
[ 23612-57-9 ]
[ 1309205-96-6 ]

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[ 1309205-99-9 ]

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53
[ 23612-57-9 ]
[ 1309351-05-0 ]

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54
[ 23612-57-9 ]
[ 1332525-80-0 ]

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55
[ 23612-57-9 ]
[ 1309206-00-5 ]

Reference： [1]Patent: WO2011/61214,2011,A1
[2]Patent: WO2011/61214,2011,A1

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[ 1309208-12-5 ]

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[ 1309208-19-2 ]

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[2]Patent: WO2011/61214,2011,A1

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[ 1309208-15-8 ]

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[2]Patent: WO2011/61214,2011,A1

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[ 1309208-16-9 ]

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[2]Patent: WO2011/61214,2011,A1

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[ 1309206-01-6 ]

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[ 1309208-20-5 ]

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[2]Patent: WO2011/61214,2011,A1

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[ 1309208-23-8 ]

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[ 1309208-28-3 ]

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[ 1309208-29-4 ]

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[ 23612-57-9 ]
[ 1309208-34-1 ]

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[ 1309206-04-9 ]

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[ 1309206-07-2 ]

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68
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[ 1309206-08-3 ]

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[ 1309206-12-9 ]

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[ 1309206-15-2 ]

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[ 1309206-20-9 ]
[ 1309206-16-3 ]

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[ 1309206-22-1 ]

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[ 1309206-26-5 ]

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[ 1309206-28-7 ]

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75
[ 23612-57-9 ]
[ 1309206-31-2 ]

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76
[ 23612-57-9 ]
[ 1309206-34-5 ]

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77
[ 23612-57-9 ]
[ 1309206-83-4 ]

Reference： [1]Patent: WO2011/61214,2011,A1
[2]Patent: WO2011/61214,2011,A1

78
[ 23612-57-9 ]
[ 1309208-86-3 ]

Reference： [1]Patent: WO2011/61214,2011,A1

79
[ 23612-57-9 ]
[ 1309206-36-7 ]
6-((E)-3-oxo-3-(3-((E)-1-(2,2,2-trifluoroethoxyimino)ethyl)azetidin-1-yl)prop-1-enyl)-3,4-dihydro-1,8-naphthyridin-2(1H)-one [ No CAS ]

Reference： [1]Patent: WO2011/61214,2011,A1

80
[ 23612-57-9 ]
[ 1309206-38-9 ]
6-((E)-3-(3-((E)-1-(ethoxyimino)ethyl)azetidin-1-yl)-3-oxoprop-1-enyl)-3,4-dihydro-1,8-naphthyridin-2(1H)-one [ No CAS ]

Reference： [1]Patent: WO2011/61214,2011,A1

81
[ 23612-57-9 ]
[ 1309206-40-3 ]

Reference： [1]Patent: WO2011/61214,2011,A1

82
[ 23612-57-9 ]
[ 1309206-85-6 ]

Reference： [1]Patent: WO2011/61214,2011,A1
[2]Patent: WO2011/61214,2011,A1

83
[ 23612-57-9 ]
[ 1309206-42-5 ]

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84
[ 23612-57-9 ]
[ 1309206-43-6 ]

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85
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[ 1309206-45-8 ]

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86
[ 23612-57-9 ]
[ 1309206-47-0 ]

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87
[ 23612-57-9 ]
[ 1309206-49-2 ]

Reference： [1]Patent: WO2011/61214,2011,A1

88
[ 23612-57-9 ]
1'-methyl-6-((E)-3-oxo-3-(3-((Z)-1-(benzyloxyimino)ethyl)azetidin-1-yl)prop-1-enyl)-1H-spiro[[1,8]naphthyridine-3,4'-piperidin]-2(4H)-one [ No CAS ]
[ 1309206-51-6 ]

Reference： [1]Patent: WO2011/61214,2011,A1
[2]Patent: WO2011/61214,2011,A1

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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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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

[ CAS No. 23612-57-9 ] {[proInfo.proName]}

Quality Control of [ 23612-57-9 ]

Related Doc. of [ 23612-57-9 ]

Product Details of [ 23612-57-9 ]

Calculated chemistry of [ 23612-57-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 23612-57-9 ]

Application In Synthesis of [ 23612-57-9 ]

[ 23612-57-9 ] Synthesis Path-Upstream 1~9

[ 23612-57-9 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 23612-57-9 ]

Alcohols

Amines

Related Parent Nucleus of [ 23612-57-9 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 23612-57-9 ]

Related Parent Nucleus of
[ 23612-57-9 ]