[ CAS No. 3731-51-9 ] {[proInfo.proName]}

Name: 3731-51-9|Pyridin-2-ylmethanamine|98%
Brand: Ambeed
SKU: A478280
Rating: 91 (30 reviews)

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

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Quality Control of [ 3731-51-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 3731-51-9 ]

Product Details of [ 3731-51-9 ]

CAS No. :	3731-51-9	MDL No. :	MFCD00006360
Formula :	C₆H₈N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WOXFMYVTSLAQMO-UHFFFAOYSA-N
M.W :	108.14	Pubchem ID :	19509
Synonyms :

Calculated chemistry of [ 3731-51-9 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	31.91
TPSA :	38.91 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) :	-7.11 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.41
Log Po/w (XLOGP3) :	-0.21
Log Po/w (WLOGP) :	0.39
Log Po/w (MLOGP) :	-0.14
Log Po/w (SILICOS-IT) :	1.01
Consensus Log Po/w :	0.49

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.87
Solubility :	14.7 mg/ml ; 0.136 mol/l
Class :	Very soluble
Log S (Ali) :	-0.15
Solubility :	76.5 mg/ml ; 0.707 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.0
Solubility :	1.07 mg/ml ; 0.00991 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 3731-51-9 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	2735
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 3731-51-9 ]

* 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 [ 3731-51-9 ]
Downstream synthetic route of [ 3731-51-9 ]

[ 3731-51-9 ] Synthesis Path-Upstream 1~12

1
[ 3731-51-9 ]
[ 21035-59-6 ]

Reference： [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 320 - 330
[2] Tetrahedron Letters, 1985, vol. 26, # 48, p. 5863 - 5866
[3] Dalton Transactions, 2013, vol. 42, # 36, p. 12878 - 12882
[4] Organic and Biomolecular Chemistry, 2017, vol. 15, # 16, p. 3507 - 3518

2
[ 3731-51-9 ]
[ 22990-77-8 ]

Reference： [1] Journal of Pharmaceutical Sciences, 1990, vol. 79, # 8, p. 750 - 753
[2] Naturwissenschaften, 1958, vol. 45, p. 492
[3] Journal of the American Chemical Society, 1946, vol. 68, p. 1330
[4] Patent: US2008/188665, 2008, A1, . Location in patent: Page/Page column 1
[5] Patent: US2008/188665, 2008, A1, . Location in patent: Page/Page column 1

3
[ 3731-51-9 ]
[ 67-56-1 ]
[ 201230-82-2 ]
[ 1658-42-0 ]

Reference： [1] ACS Catalysis, 2018, vol. 8, # 1, p. 738 - 741

4
[ 3731-51-9 ]
[ 6959-47-3 ]
[ 16858-01-8 ]

Yield	Reaction Conditions	Operation in experiment
42%	With sodium hydroxide In water at 20℃; for 48 h; Inert atmosphere	Put a rotor in a 100 mL eggplant flask, attach a three-way cock, a balloon and dry in vacuum . Under a nitrogen atmosphere, 2-chloromethylpyridine · hydrochloride (2.0 g 12.2 mmol) was added Well, it was dissolved in 20 mL of distilled water. In an ice bath, a solution prepared by dissolving NaOH (2.44 g, 61.0 mmol) in a minimum amount of distilled water was added slowly, then 2-picolylamine (0.60 g, 5.54 mmol) was added and stirred. At this time, if the solution was not uniform, a small amount of distilled water was added until it became homogeneous. The color of the solution was red. Remove from ice bath, And the mixture was stirred at room temperature for 48 hours. The color of the solution gradually turned brown, A brown oily substance insoluble in the aqueous solution precipitated. 50 mL of CH 2 Cl 2 was added to the solution, transferred to a separating funnel, and partitioned with CH 2 Cl 2 to extract an organic layer (50 mL × 3). The extracted organic layer was dehydrated with Na 2 SO 4, Concentration with an evaporator gave a brown oily substance. When the oily substance obtained was well dried under vacuum in a vacuum line, A brown semi-oily solid precipitated. Washing with a small amount of Et 2 O gave a brown solid. Recrystallization of this solid from Ligroin gave 0.68 g of pale yellow needle crystals. yield 42percent

Reference： [1] Chemistry - A European Journal, 2017, vol. 23, # 51, p. 12550 - 12558
[2] RSC Advances, 2016, vol. 6, # 108, p. 106248 - 106259
[3] Patent: JP2017/197451, 2017, A, . Location in patent: Paragraph 0037

5
[ 4377-33-7 ]
[ 3731-51-9 ]
[ 16858-01-8 ]

Reference： [1] Journal of the American Chemical Society, 1993, vol. 115, # 7, p. 2677 - 2689
[2] Journal of Physical Chemistry, 1995, vol. 99, # 10, p. 3294 - 3302
[3] Patent: WO2012/97876, 2012, A1, . Location in patent: Page/Page column 14-15
[4] Bioconjugate Chemistry, 2012, vol. 23, # 7, p. 1415 - 1425

6
[ 1121-60-4 ]
[ 3731-51-9 ]
[ 16858-01-8 ]

Reference： [1] Chemistry - A European Journal, 2008, vol. 14, # 6, p. 1804 - 1813
[2] Chinese Journal of Chemistry, 2014, vol. 32, # 6, p. 467 - 473
[3] Patent: US2012/16127, 2012, A1, . Location in patent: Page/Page column 8
[4] Advanced Synthesis and Catalysis, 2014, vol. 356, # 11-12, p. 2453 - 2458

7
[ 3731-51-9 ]
[ 31106-82-8 ]
[ 16858-01-8 ]

Reference： [1] Patent: US2003/235843, 2003, A1, . Location in patent: Page 21

8
[ 3731-51-9 ]
[ 16858-01-8 ]

Reference： [1] Chemical Communications, 2014, vol. 50, # 84, p. 12779 - 12782

9
[ 3731-51-9 ]
[ 141774-61-0 ]

Reference： [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 9, p. 2928 - 2931

10
[ 3731-51-9 ]
[ 27854-90-6 ]

Reference： [1] Synthetic Communications, 1991, vol. 21, # 21, p. 2207 - 2212
[2] Synthetic Communications, 1991, vol. 21, # 21, p. 2207 - 2212

11
[ 3731-51-9 ]
[ 4755-77-5 ]
[ 81803-60-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 8, p. 2354 - 2358

12
[ 3731-51-9 ]
[ 81803-60-3 ]

Reference： [1] Organic Letters, 2013, vol. 15, # 9, p. 2290 - 2293
[2] Patent: WO2015/25025, 2015, A1,
[3] Synthesis (Germany), 2016, vol. 48, # 23, p. 4269 - 4277

[ 3731-51-9 ] Synthesis Path-Downstream 1~87

1
[ 3731-51-9 ]
[ 19728-76-8 ]
[ 101436-98-0 ]

Reference： [1]Archiv der Pharmazie,1958,vol. 291,p. 610,620

2
[ 3731-51-9 ]
[ 941-69-5 ]
[ 13885-13-7 ]
[ 118317-33-2 ]

Reference： [1]Tetrahedron,1988,vol. 44,p. 1523 - 1534

3
[ 3731-51-9 ]
[ 71670-70-7 ]
[ 202192-57-2 ]

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

4
[ 3731-51-9 ]
[ 63-91-2 ]
[ 13650-49-2 ]
[ 76-05-1 ]
(S)-5-Amino-2-(2-amino-3-phenyl-propionylamino)-pentanoic acid (pyridin-2-ylmethyl)-amide; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 4171 - 4174

5
[ 3731-51-9 ]
[ 6230-11-1 ]
[ 2418-95-3 ]
[ 76-05-1 ]
(S)-6-Amino-2-[2-amino-3-(4-methoxy-phenyl)-propionylamino]-hexanoic acid (pyridin-2-ylmethyl)-amide; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 4171 - 4174

6
[ 3731-51-9 ]
[ 6230-11-1 ]
[ 76-05-1 ]
[ 35146-32-8 ]
2-Amino-N-{(S)-2-(4H-imidazol-4-yl)-1-[(pyridin-2-ylmethyl)-carbamoyl]-ethyl}-3-(4-methoxy-phenyl)-propionamide; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 4171 - 4174

7
[ 3731-51-9 ]
[ 84946-20-3 ]
2-amino-1-(p-fluorobenzyl)-N-[(2-pyridinyl)methyl]-1H-benzimidazole [ No CAS ]

Reference： [1]Heterocycles,1999,vol. 51,p. 2561 - 2573

8
[ 3731-51-9 ]
[ 14562-10-8 ]
3-[(pyridin-2-ylmethylimino)methyl]biphenyl-2-ol [ No CAS ]

Reference： [1]Dalton Transactions,2004,p. 2314 - 2320

9
[ 3731-51-9 ]
[ 53277-47-7 ]
6-methyl-2-[(pyridin-2-ylmethyl)-amino]-nicotinic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1191 - 1196

10
[ 3731-51-9 ]
[ 60421-23-0 ]
[ 109-52-4 ]
2-butyl-3-pyridin-2-ylmethyl-1,3-diaza-spiro[4.4]non-1-en-4-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 3137 - 3140

11
[ 3731-51-9 ]
[ 16523-31-2 ]
[ 908587-03-1 ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 5727 - 5731

12
[ 3731-51-9 ]
[ 52853-40-4 ]
[ 677298-09-8 ]

Yield	Reaction Conditions	Operation in experiment
57%	In N,N-dimethyl acetamide;	6-[{(Pyridin-2-ylmethyl)-amino]-methyl}-2,4-pteridinediamine To a solution of 6-bromomethyl-2,4-pteridinediamine hydrobromide (51 mg, 0.2 mmol) in anhydrous N,N dimethylacetamide was added 2-(aminomethyl) pyridine (22.48 ul, 0.22 mmol). The reaction mixture was stirred at 50 C. overnight. The crude product was poured into saturated bicarbonate solution. The resulted precipitate was collected and purified by preparative HPLC. 32.3 mg product was obtained. Yield: 57%; 1H NMR (500 MHz, DMSO-d6): delta 3.93801 (s, 2H), 4.05772 (s, 2H), 7.5758-7.6003 (m, 1H), 7.97993-8.00181 (m, 1H), 8.49332-8.50942 (d, J=8.05 Hz, 1H), 8.62592-8.64301 (d, J=8.545 Hz, 1H), 8.9938 (s, 1H); ESI-MS: 283 (M++1)

Reference： [1]Patent: US2005/282814,2005,A1

13
[ 3731-51-9 ]
[ 105-43-1 ]
C₁₂H₁₈N₂O [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 1856 - 1857

14
[ 3731-51-9 ]
[ 4077-76-3 ]
[ 126463-69-2 ]

Reference： [1]Dalton Transactions,2007,p. 2003 - 2013

15
[ 3731-51-9 ]
[ 1951-36-6 ]
C₂₀H₁₈N₄O₂ [ No CAS ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2007,vol. 62,p. 66 - 74

16
[ 3731-51-9 ]
[ 141774-61-0 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2928 - 2931

17
[ 3731-51-9 ]
[ 27854-90-6 ]

Reference： [1]Synthetic Communications,1991,vol. 21,p. 2207 - 2212
[2]Synthetic Communications,1991,vol. 21,p. 2207 - 2212

18
[ 3731-51-9 ]
[ 2528-00-9 ]
[ 369654-80-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 3h;	Synthesis Example 11-1: Synthesis of ethyl 5-(N-2-picolylamino methyl furan)-2-carboxylate (Compound V-3) 100.6 mg of commercially available 5-chloromethyl-2-furan ethyl carboxylate was dissolved in 2.0 ml of DMF, and then 75.1 mg of potassium carbonate and 0.167 ml of 2-picolylamine were added and the resultant mixture was stirred for 3 hours at room temperature. On completion of the reaction, the solvent was concentrated and dissolved in chloroform, followed by washing with distilled water. The resultant was dried with anhydrous sodium sulfate and a solvent was then distilled off. The residue was purified by means of silica gel column chromatography (4.5 g, chloroform/methanol = 25/1), and 103.2 mg of the above-mentioned compound was obtained as a light-yellow oily product. MS(FAB,Pos.):m/z=261[M+1]+ 1H-NMR(500MHz,CDCl3):delta=1.37(3H,t,J=7.1Hz) 3.91(2H,s) 3.94(2H,s),4.35(2H,q,J=7.1Hz),6.36(d,J=3.4Hz),7.17(1H,ddt,J=7.5,4.9,1. 0Hz),7.31(1H,dt,J=7.5,1.0Hz),7.65(1H,td,J=7.5,1.7Hz),8.47(1H, ddd,J=4.9,1.7,1.0Hz).

Reference： [1]Patent: EP1389460,2004,A1 .Location in patent: Page/Page column 33

19
[ 3731-51-9 ]
[ 136333-97-6 ]
[ 369654-72-8 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In toluene; at 80℃; for 48h;	Synthesis Example 9-2: Synthesis of methyl 4-(2-(2-picolylamino) ethyl) benzoate (Compound V-2) 0.625 ml of commercially available picolyiamine was dissolved in 15 ml of toluene and then 0.715 ml of diisopropyl ethylamine was added to the solution. To this solution, 499.7 mg of the compound obtained in Synthesis Example 9-1 was added and the resultant mixture was stirred for 2 days at 80C. On completion of the reaction, toluene was added to the solution and the resultant solution was then washed with distilled water and a saturated salt solution, followed by drying with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then the residue was purified by means of silica gel column chromatography (25 g, chloroform/methanol = 25/1), and 400.1 mg of the above-mentioned compound was obtained as a light-brown oily product. MS(FAB,Pos.):m/z=271[M+1]+ 1H-NMR(500MHz,CDCl3):delta=2.88-2.97(4H,m),3.91(3H,s),3.93(2H,s),7.16(1H,ddd,J=7.6,4.9,1.2Hz),7.24-7.30(3H,m),7.63(1H,td,J=7.6, 1.7Hz),8.54(1H,ddd,J=4.9,1.7,1.0Hz).

Reference： [1]Patent: EP1389460,2004,A1 .Location in patent: Page/Page column 31

20
[ 3731-51-9 ]
[ 7398-42-7 ]
[ 369654-63-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 20℃; for 1h;	Synthesis Example 8-2: Synthesis of methyl 4-(N-2-picolylamino methyl) phenyl acetate (Compound V-1) 92.9 mg of commercially available 2-picolylamine was dissolved in 2 ml of DMF, and then 56.5 mg of potassium carbonate was added to the solution. To this solution, 100. 8 mg of the compound obtained in Synthesis Example 8-1 was added and the resultant mixture was stirred for 1 hour at room temperature. On completion of the reaction, the solution was concentrated and then the residue was dissolved in chloroform. The resultant was washed with distilled water and was dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and then the residue was purified by means of silica gel column chromatography (5.5 g, chloroform/methanol = 15/1), and 73.2 mg of the above-mentioned compound was obtained as a colorless oily product. MS(FAB,Pos.):m/z=271[M+1]+ 1H-NMR(500MHz,CDCl3):delta=1.85(2H,brs),3.62(2H,s),3.69(3H,s),3.83 (2H,s),3.92(2H,s),7.15-7.18(1H,m),7.23-7.27(3H,m),7.30-7.36(3 H,m),7.64(1H,td,J=7.6,1.7Hz),8.56(1H,ddd,J=5.1,1.7,1.0Hz).

Reference： [1]Patent: EP1389460,2004,A1 .Location in patent: Page/Page column 29

21
[ 3731-51-9 ]
[ 66176-39-4 ]
[ 298181-83-6 ]
[ 405229-93-8 ]

Yield	Reaction Conditions	Operation in experiment
20%	With triethylamine; In dichloromethane;	Preparation of N-Pyridin-2-ylmethyl-4-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-benzenesulfonamide To a stirred solution of 4-bromomethyl-benzenesulfonyl chloride (500 mg, 1.85 mmol) and Et3N (269 muL, 1.85 mmol) in CH2Cl2 (10 mL), at -78° C., was added aminomethyl pyridine (190 muL, 1.85 mmol) in one portion. The resultant solution was stirred at -78° C. for 20 minutes. A second portion of Et3N (269 muL, 1.85 mmol) was added, followed by addition of <strong>[298181-83-6]8-amino-5,6,7,8-tetrahydroquinoline</strong> (274 mg, 1.85 mmol). The solution was stirred for 18 h at room temperature. The mixture was diluted with CH2Cl2 (100 mL/mmol), filtered through celite, and concentrated. The crude material was purified by chromatography on silica gel (CH2Cl2/MeOH/NH4OH 48:1:1) to give AMD9367 (150 mg, 20percent) as a white foam. 1H NMR (300 MHz, CD3COCD3) delta 1.69-1.98 (m, 2H), 2 00-2.05 (m, 1H), 2.11-2.18 (m, 1H), 2.71-2.85 (m, 3H), 3.82 (m, 1H), 3.96 (d, 2H, J=6.0 Hz), 4.23 (br s, 2H), 6.10 (br s, 1H), 7.05-7.15 (m, 3 H), 7.38 (d, 1H, J=7.8 Hz), 7.49 (d, 2H, J=9.0 Hz), 7.55-7.58 (m, 1H), 7.79 (d, 2H, J=9.0 Hz), 8.39 (d, 1H, J=4.8 Hz), 8.44 (d, 1H, J=4.5 Hz), 13C NMR (75.5 MHz, CD3COCD3) delta 20.05, 29.14, 29.20, 47.79, 51.70, 58.09, 122.39, 123.01, 127.68, 129.07, 132.90, 137.17, 137.40, 138.24, 146.62, 147.24, 149.38, 155.21, 157.54. ES-MS m/z 409 (M+H). Anal. Calcd. for C22H24N4O2S*0.2H2O: C, 64.12; H, 5.97; N, 13.59. Found: C, 64.10; H, 5.91; N, 13.71.

Reference： [1]Patent: US2002/147192,2002,A1

22
[ 3731-51-9 ]
[ 99368-67-9 ]
5-nitro-N-(pyridin-2-ylmethyl)-3-(trifluoromethyl)-2-pyridinamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	Preparation 146 A mixture of <strong>[99368-67-9]2-chloro-5-nitro-3-(trifluoromethyl)pyridine</strong> (226mg) and 2-pyridylmethanamine (0.2ml) in tetrahydrofuran (2.0ml) was stirred for 18 hours. The mixture was poured into water and stirred for 1 hour. The precipitated solid was collected by filtration, washed with water, and dried to give 5-nitro-N-(2-pyridylmethyl)-3-(trifluoromethyl)-2-pyridinamine (277mg).

Reference： [1]Patent: EP1264820,2002,A1

23
[ 3731-51-9 ]
[ 877173-84-7 ]
[ 924902-37-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 80℃;	The amine (1.1 equivalents) and 1.5 equivalents of diisopropylethylamine in isopropanol at a total concentration of 1M were heated overnight at 80 0C. The reaction mixture was concentrated, washed with water, filtered, and the resulting solid partitioned between ethyl acetate or dichloromethane and water. After a further water wash, and a citirc acid wash with amines possessing no additional basic functionality, the organic layer was dried then concentrated to give the crude 7-substituted amino-3- bromopyrazolo[1 ,5a]pyrimidine in good yield. The purity of this material was sufficient for use in the next stage cross-couipling reaction. As Example 1, the use of 2- aminomethylpyidine gave 7- aminomethyl-3-bromopyrazolo[1 ,5a]pyrimidine in 91% yield and 99% purity (MS: m/z 306/304 [M+H]+).

Reference： [1]Patent: WO2007/17678,2007,A1 .Location in patent: Page/Page column 45

24
[ 3731-51-9 ]
[ 6147-53-1 ]
[ 3244-41-5 ]
{Co(acpa)2}BPh₄ [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 1953 - 1958

25
[ 3731-51-9 ]
[ 6147-53-1 ]
[ 3244-41-5 ]
{Co(bzpa)2}BPh₄ [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 1953 - 1958

26
[ 3731-51-9 ]
sodium triscarbonatocobaltate(III) trihydrate [ No CAS ]
[ 58966-93-1 ]
[ 7646-85-7 ]
{CoCl(N₃H₃(C₂H₄)3)(NH₂CH₂C₅H₄N)}⁽²⁺⁾*{ZnCl₄}^(2-)={CoCl(N₃H₃(C₂H₄)3)(NH₂CH₂C₅H₄N)}{ZnCl₄} [ No CAS ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1993,p. 1019 - 1022

27
[ 3731-51-9 ]
[ 40972-42-7 ]
[ 1034622-04-2 ]

Yield	Reaction Conditions	Operation in experiment
27%	In ethanol; at 120.0℃; for 16.0h;	6-Chloroimidazo[1,2-b]pyridazine 41 (6.53 mmol) was dissolved in chloroform (12 mL) and N-chlorosuccinimide (6.53 mmol) added under N2. After stirring for 16 h, the mixture was partitioned between saturated sodium hydrogensulfate solution (25 mL) and chloroform (12 mL). The organic layer was removed, washed with water (2×), dried and concentrated to provide <strong>[40972-42-7]3,6-dichloroimidazo[1,2-b]pyridazine</strong> 5 (1.05 g, 85%) as an orange solid; 1H NMR (500 MHz, CDCl3) delta 7.92 (d, J=9.5 Hz, 1H), 7.74 (s, 1H), 7.12 (d, J=9.5 Hz, 1H). 3,6-Dichloroimidazo[1,2-b]pyridazine 5 (150 mg, 0.8 mmol) and the desired amine (1 mL) were heated in a sealed tube for 16 hr at 120 C. Upon cooling the reaction mixture was concentrated and purified by column chromatography (12 g ISCO column eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 80% methylene chloride over 30 min at 25 mL/min) to provide the desired product 6.

Reference： [1]Patent: US2008/153813,2008,A1 .Location in patent: Page/Page column 10

28
[ 3731-51-9 ]
[ 102359-00-2 ]
[ 848472-05-9 ]

Yield	Reaction Conditions	Operation in experiment
68%	With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; acetonitrile; at 20℃; for 1.58333h;	To A NN-DIMETHYLFORMAMIDE/ACETONITRILE, (2 mL: 10 mL), mixture containing ethyldiisopropylamine (0.52 ML, 3 mmol) was added <strong>[102359-00-2]2-oxoindoline-5-carboxylic acid</strong> (0.354 g, 2.0 mmol; described in: Sun L. et al. J. MED. Chem. 2000, 43 (14), 2655:), O- (BENZOTRIAZOL-1-YL)-N, N, N, N-TETRAMETHYLURONIUM tetrafluoroborate (0.77 g, 2.4 mmol) and 1-HYDROXYBENZOTRIAZOLE hydrate (0.324 g, 2.4 mmol) and stirred for 5 min at room temperature. Thereafter, 2- (AMINOMETHYL) pyridine (0.562 g, 5.2 mmol) was added and the resulting reaction mixture was stirred for 90 min followed by addition of a saturated aqueous NAHCO3 solution (10 ML). The solvents were removed in vacuo and 0.364 g (68% yield) of the title product was obtained as a white solid after purification on a silica gel column using chloroform/methanol, (9: 1), as the eluent : 1H NMR (DMSO-d6, 400 MHz) 8 10. 66 (s, 1 H), 8.96 (t, 7= 5. 6 HZ, 1 H), 8.55 (d, J = 4.4 Hz, 1 H), 7. 85 (d, J = 8. 0 HZ, I H), 7.83 (s, 1 H), 7. 78 (t, J = 7.6 Hz, 1 H), 7.34 (d, J = 8.0 Hz, 1 H), 7.29 (t, J= 6. 4 Hz, 1 H), 6.92 (d, J = 8.0 Hz, 1 H), 4.59 (d, J = 6.0 Hz, 2 H), 3. 58 (s, 2 H); MS (EI) MLZ 268 (M++1).

Reference： [1]Patent: WO2005/27823,2005,A2 .Location in patent: Page/Page column 42-43

29
[ 3731-51-9 ]
[ 24424-99-5 ]
[ 108499-32-7 ]
[ 370594-63-1 ]

Yield	Reaction Conditions	Operation in experiment
		Synthesis Example 14-2: Synthesis of 5-(N-Boc-N-2-picolylamino methyl) thiophene-2-carboxylic acid (Compound VII-7) 513 mg of the compound obtained in Synthesis Example 14-1 was dissolved in 10 ml of DMF, and then 603 mg of potassium carbonate and 0.45 ml of 2-picolylamine were added to the solution. After 17 hours, the reaction solution was concentrated and then water was added thereto, followed by extraction with chloroform. An organic layer was washed with a saturated salt solution and was then dried with anhydrous sodium sulfate. The residue obtained by concentrating the layer was dissolved in 6 ml of dioxane, and then 0.55 ml of di-t-butyldicarbonate and 6 ml of a 1 mol/l sodium hydroxide aqueous solution were added to the solution. After 6 hours, about 2 ml of a 1 mol/l sodium hydroxide aqueous solution was added to the reaction solution. Then, the solution was further stirred for 4 hours. The reaction solution was concentrated and water and 1 mol/l hydrochloric acid were added to the solution to be slightly acidic. Then, the solution was extracted with chloroform. An organic layer was dried with anhydrous sodium hydroxide and concentrated. The resulting residue was dissolved in 12 ml of methanol, to which 12 ml of a 1 mol/l sodium hydroxide aqueous solution was added. After 16 hours, the reaction solution was concentrated and dissolved in water, followed by gradually adding 1 mol/l hydrochloric acid to adjust to pH 4 to 5. After the solution was left to stand for overnight, a precipitated solid was filtrated and dried under reduced pressure. Consequently, 523.3 mg of the above-mentioned material was obtained as a white solid product. MS(FAB,Pos.):m/z=349[M+1]+ 1H-NMR(500MHz,CDCl3): delta=1.50 and 1.55 (9H,2s), 4.52, 4.60, 4.64 and 4.69 (4H,4s),6.93 and 6.97 (1H,2d,J=3.7Hz), 7.33 (1H,dd,J=5.6, 7.1Hz), 7.37 and 7.50 (1H,2d,J=7.6Hz), 7.67 (1H,d,J=3.7Hz), 7.80 (1H,t,J=7.3Hz), 8.69 (1H,brs).

Reference： [1]Patent: EP1389460,2004,A1 .Location in patent: Page/Page column 38

30
[ 3731-51-9 ]
[ 24424-99-5 ]
[ 193966-70-0 ]
5-(N-Boc-N-2-picolylamino methyl)pyrazine-2-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Synthesis Example 13-3: Synthesis of 5-(N-Boc-N-2-picolylamino methyl)pyrazine-2-carboxylic acid (Compound VII-6) 320 mg of the compound obtained in Synthesis Example 13-2 was dissolved in 6.4 ml of DMF, and then 383 mg of potassium carbonate and 286 mul of 2-picolylamine were added to the solution. After the 17-hour reaction, the reaction solution was concentrated and then water was added thereto, followed by extracting with chloroform. An organic layer was washed with a saturated salt solution. Subsequently, the organic layer was dried with anhydrous sodium sulfate and concentrated, and 444.1 mg of a crude product of the above-mentioned compound was obtained as brown syrup. The crude product was dissolved in 4 ml of dioxane, and then 0.35 ml of di-t-butyldicarbonate and 4 ml of a 1 mol/l sodium hydroxide aqueous solution were added to the solution. After 2 hours, the reaction solution was concentrated and diluted hydrochloric acid was added to the reaction solution, followed by extraction with chloroform. An organic layer was washed with a saturated salt solution and then dried with anhydroussodiumsulfate,followed by concentration, and 158.8 g of the above-mentioned compound was obtained as a light-brown solid product. MS(FAB,Pos.):m/z=345[M+1]+

Reference： [1]Patent: EP1389460,2004,A1 .Location in patent: Page/Page column 36-37

31
[ 3731-51-9 ]
[ 39890-98-7 ]
[ 1000150-83-3 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 20 - 80℃; for 64h;	PREPARATION EXAMPLE 1 PREPARATION OF N-(2-PYRIDYLMETHYL)-6-CHLORO-4-(TRIFLUOROMETHYL)-2-PYRIDYLAMINE (Compound No. 128) To a solution of 10 g of <strong>[39890-98-7]2,6-dichloro-4-(trifluoromethyl)pyridine</strong> in 50 ml of ethanol, 10 g of 2-picolylamine was added and stirred at room temperature for 24 hours, and then reacted at 60C for 16 hours and at 80C for 24 hours. After completion of the reaction, ethanol was distilled off under reduced pressure, and to the residue, ethyl acetate was added. The ethyl acetate solution was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate, and ethyl acetate was distilled off under reduced pressure. The obtained solid residue was recrystallized from hexane to obtain 9.55 g of the desired product.

Reference： [1]Patent: EP2030971,2009,A1 .Location in patent: Page/Page column 19

32
[ 3731-51-9 ]
[ 10165-86-3 ]
[ 369654-85-3 ]

Reference： [1]European Journal of Organic Chemistry,2008,p. 4412 - 4415
[2]Journal of Organic Chemistry,2012,vol. 77,p. 8968 - 8979,12

33
[ 3731-51-9 ]
[ 100202-78-6 ]
[ 1051461-51-8 ]

Reference： [1]Chemistry - A European Journal,2008,vol. 14,p. 6742 - 6753

34
[ 3731-51-9 ]
[ 3177-24-0 ]
[ 1141376-11-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 6071 - 6077

35
[ 3731-51-9 ]
[ 201230-82-2 ]
[ 29578-83-4 ]
[ 1158949-11-1 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 6898 - 6899

36
[ 3731-51-9 ]
[ 16042-25-4 ]
[ 1184723-81-6 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 4916 - 4918

37
[ 3731-51-9 ]
[ 2736-23-4 ]
[ 1216942-12-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 930 - 938

38
[ 3731-51-9 ]
[ 37366-09-9 ]
[ 99646-28-3 ]
[dichloro((R)-2,2'-bis(di-4-tolylphosphino)-1,1'-binaphthyl)(α-picolylamino)ruthenium(II)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%		A ruthenium complex (R)-1 (RuCl2[(R)-tolbinap](pica)) shown in chemical formula 2 below was synthesized as follows. First, 105.5 mg (0.21 mmol) [RuCl2(eta6-benzene)]2 (Aldrich Chemical), 2 equivalents (R)-TolBINAP (286.0 mg, 0.42 mmol) (AZmax Co.), and 5.0 mL DMF were placed in a 10 mL Schlenk flask under argon atmosphere to prepare a solution. After argon was passed through the solution for five minutes, the solution was heated at 100C for 10 minutes. The solvent was then removed under vacuum, 45.4 mg (0.42 mmol) of 2-picolylamine (PICA) (Tokyo Chemical Industry Co., Ltd.) was added thereto along with 3.0 mL of methylene chloride, and the resulting solution was stirred for 2 hours. By decreasing the volume to about 0.5 mL and then adding hexane (2 mL), yellow precipitates were formed. The supernatant was removed by filtration, and the resulting powder was vacuum-dried to yield a ruthenium complex (R)-1 in 86% yield (322.0 mg). The ruthenium complex (R)-1 was used in the hydrogenation reaction described below without purification. The melting point was >150C (decomposition point). The ruthenium complex (R)-1 was obtained as a diastereomer mixture. By heating this mixture at 80C for 30 minutes in toluene, the content of the main diastereomer increased to >90% in terms of relative integral. The spectrum data of the ruthenium complex (R)-1 was as follows: 1HNMR (400 MHz, C6D6) delta1.78(s, 3, CH3), 1.90(s, 3, CH3), 2.28(s, 3, CH3), 2.33(s, 3, CH3), 2.86(br s, 1, NHH), 3.22(br s, 1, NHH), 3.95(br s, 1, CHH), 4.93(br s, 1, CHH), 6.19-8.36(m, 32, aromatics); 31PNMR(161.7 MHz, C6D6) delta44.74(d, J = 35.6 Hz), 41.93 (d, J = 35.6 Hz). However, the reaction rate and the enantioselectivity of the hydrogenation reaction of the ketone described below are independent of the initial diastereomer mixture.

Reference： [1]Patent: EP1813621,2007,A1 .Location in patent: Page/Page column 4

39
[ 3731-51-9 ]
[ 4755-77-5 ]
[ 81803-60-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2354 - 2358

40
[ 29270-56-2 ]
[ 3731-51-9 ]
[ 1006062-31-2 ]

Yield	Reaction Conditions	Operation in experiment
79%	With sodium hydrogencarbonate; In methanol; water; at 23℃; for 18h;Darkness; Inert atmosphere;	To a vial containing NBD-F 2 (61 mg, 0.333 mmol, 1.0 equiv) was added a solution of 2-pyridylmethylamine (picolylamine) 17 (39.6 mg, 0.367 mmol, 1.1 equiv) in 0.9 mL MeOH. The reaction was stirred at 23 C in the dark for 18 h. The solvent was removed in vacuo to yield a red clay. The clay was washed with 15 mL water and was then loaded onto a silica column using the dry-loading technique (see above). Flash column chromatography of the residue on silica gel (gradient used: DCM, then 19:1 DCM/MeOH) afforded the desired product 25. The film was redissolved in acetone and filtered through a Celite plug to remove the insoluble silica gel residue, producing 25 as a red solid (71 mg, 79%). Rf (9:1 DCM/MeOH) = 0.46. 1H-NMR (CDCl3 , 500 MHz) delta: 8.72 (1H, dd, J = 5.2, 0.9 Hz), 8.57 (1H, d, J = 8.5 Hz), 8.04 (1H, br s), 7.86 (1H, t, J = 7.9 Hz), 7.45 (1H, d, J = 7.6 Hz), 7.41 (1H, dd, J = 7.0, 5.2 Hz), 6.31 (1H, d, J = 8.2 Hz), 4.87 (2H, br s). HRMS (ES+): calcd for C12H10N5O3 [M+H]+ 272.0784, found 272.0793.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 2533 - 2535

41
[ 3731-51-9 ]
[ 10111-08-7 ]
[ 1356408-83-7 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; for 1h;Reflux;	General procedure: Neat secondary aromatic or aliphatic amine (5.0 mmol) was introduced at rt to a solution of imidazole-2-carboxaldehyde (1) (0.48 g, 5.0 mmol) in MeOH (100 mL) and the reaction was stirred at reflux for 1 h. After that time, solvent was evaporated under reduced pressure affording crude imines 2 that were used directly in the next step. The crude imine (5.0 mmol) was dissolved in dry toluene (50 mL) and diethyl phosphite (0.65 mL, 5.0 mmol) or ethyl phenylphosphinate (0.75 mL, 5.0 mmol) was added. The mixture was heated to reflux for 2 h and then concentrated under reduced pressure affording crude esters 3 as thick oils or semi-solids. The phosphinate esters 3c,d were recrystallized from a mixture of toluene/hexane. The phosphonate esters 3a,b were characterized as oxalate salts. The oxalates were obtained in the following way; the crude ester (1.0 equiv) was dissolved in acetone (10 mL) and oxalic acid (COOH)2·2H2O (2.0 equiv) in acetone (10 mL) was added and the mixture was refrigerated. The separated precipitate was filtered, washed with cold acetone (10 mL) and dried on air.

Reference： [1]Tetrahedron,2012,vol. 68,p. 1223 - 1229

42
[ 3731-51-9 ]
[ 892-48-8 ]
[ 1394955-66-8 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 8066 - 8074,9

43
[ 3731-51-9 ]
[ 17289-26-8 ]
C₁₁H₁₄N₄ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 8968 - 8979,12

44
[ 3731-51-9 ]
[ 17289-26-8 ]
[ 1402045-90-2 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 8968 - 8979,12

45
[ 3731-51-9 ]
[ 35969-75-6 ]
[ 1402046-08-5 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 8968 - 8979,12

46
[ 3731-51-9 ]
[ 10165-86-3 ]
[ 1402045-98-0 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 8968 - 8979,12

47
[ 3731-51-9 ]
[ 2065-37-4 ]
[ 5230-70-6 ]

Yield	Reaction Conditions	Operation in experiment
29%	In ethanol; for 0.166667h;	2-((pyridin-2- ylmethyl)amino)naphthalene-l,4-dione (2p). To a solution of 2-bromo-l,4-napthoquinone (283 mg, 1.2 mmol) in abs EtOH (40 mL) was added an excess of 2-picolylamine (247 uL, 2.4 mmol). The reaction was stirred for 10 minutes and then concentrated in vacuo. Compound was purified using chromatography on silica gel eluting with ethyl acetate and hexane, followed by reverse phase purification on CI 8 silica to yield 90 mg yellowish powder (29% yield). MS m/z calcd (M+) 265.09, found 265.1. 1H NMR (400 MHz, DMSO- d6) Shift 8.59 (br. s., 1H), 8.10 (t, J = 6.05 Hz, 1H), 8.02 (d, J = 7.70 Hz, 1H), 7.92 (d, J = 7.70 Hz, 1H), 7.80 - 7.87 (m, 2H), 7.71 - 7.78 (m, 1H), 7.31 - 7.52 (m, 2H), 5.61 (s, 1H), 4.56 (br. s., 2H). C13-HSQC (400 MHz, DMSO-d6) Shift (ppm) 39.72, 46.52, 101.13, 122.49, 123.49, 125.86, 125.86, 132.62, 135.29, 138.79, 148.41.

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1007 - 1022
[2]Patent: WO2014/74976,2014,A1 .Location in patent: Paragraph 00224

48
[ 3731-51-9 ]
[ 1679-53-4 ]
C₁₆H₂₆N₂O₂ [ No CAS ]

Reference： [1]Analytical Chemistry,2013,vol. 85,p. 3553 - 3560

49
[ 3731-51-9 ]
[ 81803-60-3 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 2290 - 2293
[2]Patent: WO2015/25025,2015,A1
[3]Synthesis,2016,vol. 48,p. 4269 - 4277

50
[ 3731-51-9 ]
[ 65189-15-3 ]
[ 1441876-61-4 ]

Yield	Reaction Conditions	Operation in experiment
41%		Catalytic amounts of palladium(ll)acetate (7.8 mg, 0.035 mmol) and racemic BINAP (23 mg, 0.035 mmol) were added to degassed toluene (5 ml_). After stirring for 5 minutes at rt 5,6- dichloronicotinonitrile (200 mg, 1.156 mmol) and 2-picoloylamine (166 muIota_, 1.619 mmol) were added. Stirring was continued for 10 minutes at rt, then potassium carbonate (811 mg, 5.78 mmol) was added and the temperature was raised to 100 C for 12 h. The resulting dark suspension was concentrated i.V. and the crude material was purified by chromatography (Biotage Isolera Four, heptanes/ethyl acetate 100:0 to 60:40) to give the desired product as a yellow foam (1 15 mg, 0.47 mmol, 41 %). 1H NMR (400 MHz, DMSO-d6) delta ppm 8.51 (d, J=4.69 Hz, 1 H) 8.39 (d, J=1.95 Hz, 1 H) 8.07 - 8.21 (m, 2 H) 7.67 - 7.80 (m, 1 H) 7.25 (t, J=7.22 Hz, 2 H) 4.74 (d, J=5.86 Hz, 2 H) MS(APCI) m/e 245 (M+H)+ RT= 0.80 min (Method B)

Reference： [1]Patent: WO2013/80120,2013,A1 .Location in patent: Page/Page column 66

51
[ 3731-51-9 ]
[ 4139-61-1 ]
[ 16231-98-4 ]
6-(5-bromo-2-hydroxybenzoyl)-2,7-bis(4-chlorophenyl)-1-picolinoyl-3,8a-di(pyridin-2-yl)hexahydroindolizin-5(1H)-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 11414 - 11420

52
[ 3731-51-9 ]
[ 4139-61-1 ]
[ 24582-66-9 ]
6-(5-bromo-2-hydroxybenzoyl)-1-picolinoyl-3,8a-di(pyridin-2-yl)-2,7-di-p-tolylhexahydroindolizin-5(1H)-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 11414 - 11420

53
[ 3731-51-9 ]
[ 4139-61-1 ]
[ 18451-44-0 ]
6-(5-bromo-2-hydroxybenzoyl)-2,7-bis(4-methoxyphenyl)-1-picolinoyl-3,8a-di(pyridin-2-yl)hexahydroindolizin-5(1H)-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 11414 - 11420

54
[ 3731-51-9 ]
[ 4139-61-1 ]
[ 24582-72-7 ]
6-(5-bromo-2-hydroxybenzoyl)-2,7-bis(4-fluorophenyl)-1-picolinoyl-3,8a-di(pyridin-2-yl)hexahydroindolizin-5(1H)-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 11414 - 11420

55
[ 3731-51-9 ]
[ 57295-30-4 ]
[ 68-11-1 ]
[ 1600490-07-0 ]

Yield	Reaction Conditions	Operation in experiment
82%		General procedure: Benzylamine (1.0 mmol) was added to a stirred solution of benzaldehyde (1.2 mmol) in dichloromethane (10 mL) at 0 C. After stirring for 5 min thioglycolic acid (2.0 mmol) wasadded to the above reaction and stirring was continued for another 5 min at 0 C. Silica gel (0.5g) was then added and the mixture was stirred for 4 h at room temperature when TLC showedcomplete conversion of amine. The solvent was removed under reduced pressure and the slurryso formed was purified by flash column chromatography over 12 g SNAP cartridge by elutingwith gradient of 10-20% ethyl acetate in hexane to afford 3-benzyl-2-phenylthiazolidin-4-one in 87% yield.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 2463 - 2466

56
[ 3731-51-9 ]
[ 3747-74-8 ]
1-(pyridin-2-yl)-N,N-bis(quinolin-2-ylmethyl)methanamine [ No CAS ]

Reference： [1]Dalton Transactions,2014,vol. 43,p. 10086 - 10103
[2]New Journal of Chemistry,2019,vol. 43,p. 6186 - 6196

57
[ 3731-51-9 ]
[ 50982-12-2 ]
[ 7688-25-7 ]
[RuCl₂(2-aminomethylpyridine)(1,4-bis(diphenylphosphino)butane)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Reflux;	The catalyst precursor, preferably [RuCI2(COD)]m (1 eq.) (COD = cis,cis-cycloocta-1 ,5 diene), 1 ,4-bis(diphenylphosphino)butane (1.0-1 .2 eq., preferably 1.0 eq.) and 2-picolylamine (1 .0-1.4 eq., preferably 1.225 eq.) were dissolved in one of the above mentioned solvents, preferably methyl isobutylketone (10-20 ml/g Ru-precursor, preferably 20 ml/g). The mixture was heated to reflux for 3 - 5 hours and then cooled to ambient temperature. The solid precipitate was filtered off and washed with the same solvent that was used for the reaction. A person skilled in the art can determine the cis-/trans- isomeric ratio by NMR. The diastereomeric ratios generated by this method are usually in the range of d.r. (diastereomeric ratio) >98% towards the cis isomer. The same results can be achieved starting with [RuCI2(dmso-KS)3(dmso-KO)], [RuCI2(dmso-KS)4]or [RuCI2(bicyclo[2.2.1 ]hepta- 2,5-diene)]m as precursor

Reference： [1]Patent: WO2014/166777,2014,A1 .Location in patent: Page/Page column 7; 8

58
[ 3731-51-9 ]
[ 56844-12-3 ]
6-bromo-N-(pyridin-2-ylmethyl)thieno[2,3-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	In isopropyl alcohol; at 80℃; for 1h;Inert atmosphere;	General procedure: Compound 1 (1.00 g, 4.01 mmol) was mixed with the benzylamine (2-3 eq.) and i-PrOH (2-10 mL) and agitated at 80 C for 1-50 h, under nitrogen atmosphere. Then the mixture was cooled to rt, concentrated in vacuo, diluted with water (50 mL) and diethyl ether (100 mL) or EtOAc (100 mL). After phase separation, the water phase was extracted with more diethyl ether (2×50 mL) or EtOAc (2×50 mL). The combined organic phases were washed with saturated aq NaCl solution (25-50 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude oil was purified by drying under reduced pressure to constant weight, by silica-gel column chromatography or crystallized as specified for each individual compound.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 94,p. 175 - 194

59
[ 3731-51-9 ]
[ 584-87-2 ]
4-hydroxy-3-(((pyridin-2-yl)methylimino)methyl)benzoic acid [ No CAS ]

Reference： [1]Inorganic Chemistry,2015,vol. 54,p. 10918 - 10924

60
[ 3731-51-9 ]
[ 16744-81-3 ]
iron(II) trifluoromethanesulfonate acetonitrile disolvate [ No CAS ]
C₂₆H₂₆FeN₆O₂⁽²⁺⁾*2CF₃O₃S^(1-) [ No CAS ]

Reference： [1]Inorganic Chemistry,2015,vol. 54,p. 10141 - 10152

61
[ 3731-51-9 ]
[ 16744-81-3 ]
C₂₆H₂₆FeN₆O₂⁽²⁺⁾*2CF₃O₃S^(1-) [ No CAS ]

Reference： [1]Inorganic Chemistry,2015,vol. 54,p. 10141 - 10152

62
[ 3731-51-9 ]
[ 16744-81-3 ]
C₁₃H₁₃N₃O [ No CAS ]

Reference： [1]Inorganic Chemistry,2015,vol. 54,p. 10141 - 10152

63
[ 53547-60-7 ]
[ 3731-51-9 ]
C₁₃H₁₃N₃ [ No CAS ]

Reference： [1]Inorganic Chemistry,2015,vol. 54,p. 10141 - 10152

64
[ 3731-51-9 ]
[ 1126-44-9 ]
C₁₂H₁₂N₄OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 2h;	Example47 N- (5- ( (4- (1-chloroimidazo [1, 5-a] pyridin-3-yl) pyrimidin-2-yl) amino) -2- ( (2- (dimethylamino) ethyl) (methyl) amino) -6-methoxypyridin-3-yl) acrylamide (47) 2- (methylthio) -N- (pyridin-2-yl) pyrimidine-4-carboxamide (47a) A mixture of pyridin-2-ylmethanamine (900 mg, 8.3 mmol) , 2- (methylthio) pyrimidine -4-carboxylic acid (1 g, 5.9 mmol) (prepared by following the literature WO2006/117368) , HOBT (2.4 g, 17.7 mmol) , EDCI (3.4 g, 17.7 mmol) , TEA (1.78 g, 17.7 mmol) in DMF (10 ml) was stirred at r.t. for 2 h. The reaction was cooled to room temperature and quenched by water (10 mL) . The mixture was adjusted to pH 910 using sodium carbonate. The resulting mixture was extracted with EA (15 mL × 3) . The organic layers were combined and washed with brine (20 mL) , dried over Na2SO4. The solids were filtered out and the filtrate was concentrated in vacuum. The residue was purified by column chromatography on silica gel eluting with PE/EA (2:11:1) to give 2- (methylthio) -N- (pyridin-2-yl) pyrimidine-4-carboxamide (47a) . MS-ESI (m/z) : 247 [M + 1]+.

Reference： [1]Patent: WO2015/188777,2015,A1 .Location in patent: Paragraph 00362-00364

65
[ 3731-51-9 ]
[ 1180-71-8 ]
2-((1S,3aS,4aR,4bR,9aR,11aS)-1-(furan-3-yl)-9a-(hydroxymethyl)-4b,7,7,11a-tetramethyl-3,5-dioxotetradecahydroisobenzofuro[5,4-f]oxireno[2,3-d]isochromen-9-yl)-N-(pyridin-2-ylmethyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With montmorillonite K-10; In ethanol; at 80℃; for 0.5h;Sealed tube; Microwave irradiation;	General procedure: To a solution of 1 (2.0 mmol) in absolute EtOH (8.0 mL)in a glass tube was added dropwise the appropriate amine(3.6 mmol) and K-10 (0.3 g mmol-1); the quartz tubewas sealed with reaction mixture and introduced intoa microwave oven. The flask was irradiated for 30 min(150 W) the temperature of 80 C. After completion of thereaction the mixture was filtered, the organic phase wasdried with Na2SO4, filtered and the solvent was evaporatedunder reduced pressure to give the crude products. All thecompounds were purified by column chromatographyon silica gel using 2-5% EtOH-CH2Cl2 as eluent to giveanalytically pure products 3a-m. The products werecharacterized by corresponding spectroscopic data (1H and13C NMR, and HRMS).

Reference： [1]Journal of the Brazilian Chemical Society,2016,vol. 27,p. 161 - 178

66
[ 3731-51-9 ]
[ 2168-78-7 ]
[ 1950-68-1 ]
C₂₀H₁₆N₂OS [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 48375 - 48378

67
[ 3731-51-9 ]
[ 5969-47-1 ]
[ 1950-68-1 ]
C₂₀H₁₅FN₂OS [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 48375 - 48378

68
[ 3731-51-9 ]
[ 141704-11-2 ]
ethyl 5-(pyridin-2-yl)imidazo[5,1-b]thiazole-7-carboxylate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 8617 - 8624

69
[ 3731-51-9 ]
[ 4506-66-5 ]
N<SUP>1</SUP>,N<SUP>5</SUP>-di(2-pyridylmethylene)-1,2,4,5-tetraaminobenzene [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 5340 - 5343

70
[ 3731-51-9 ]
[ 4506-66-5 ]
[ 917768-08-2 ]

Reference： [1]Organic Letters,2016,vol. 18,p. 5340 - 5343

71
[ 3731-51-9 ]
[ 39621-11-9 ]
[ 502723-69-5 ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 10042 - 10045

72
[ 3731-51-9 ]
[ 68470-59-7 ]
[ 25599-10-4 ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium carbonate; In acetonitrile; at 20℃;	A solution of <strong>[68470-59-7]2-bromomethyl-6-methylpyridine</strong> (0.69 g, 4 mmol) in acetonitrile (6 mL) was added dropwise for 3 h to a solution of 2- (aminomethyl) pyridine(0.22 g, 2 mmol) and anhydrous Na2CO3 (0.53 g, 5 mmol) in acetonitrile (6 mL).After the dropwise addition, stirring was continued at room temperature. After the reaction was completed, the mixture was filtered, the solvent was removed and the resulting residue was dissolved in CH2Cl2 (10 mL), washed with saturated aqueous NaHCO3, dried over anhydrous MgSO4,Filtration and rotary evaporation of the solvent afforded a reddish brown oil which was isolated by column chromatography and dried in vacuo to give 0.46 g of the desired target product in 72% yield.
	With sodium hydroxide; In water; at 0 - 20℃;	1.86 g of the synthesized <strong>[68470-59-7]6-methyl-2-(bromomethyl) pyridine</strong> and 10 mL of water were added into a 100 mL flask and stirred at 0 degree. 1.08 g of 2-pyridylmethylamine was added thereto and stirred at 0 degree. 2 mL of an aqueous solution of sodium hydroxide having a concentration of 1 mol/L was added thereto and stirred at room temperature overnight. Water and chloroform were added thereto for liquid separating and extraction, and an organic phase obtained was washed with water three times, pre-dried over anhydrous sodium sulfate, and concentrated under reduced pressure, and thus, a compound A4-90 was obtained as a light yellow solid.

Reference： [1]Patent: CN107312024,2017,A .Location in patent: Paragraph 0033; 0052; 0053; 0081; 0082; 0083
[2]Patent: US10215898,2019,B2 .Location in patent: Page/Page column 141; 142

73
[ 3731-51-9 ]
[ 66176-39-4 ]
[ 298181-83-6 ]
[ 405058-47-1 ]

Reference： [1]Patent: US2002/147192,2002,A1

74
[ 3731-51-9 ]
[ 699-55-8 ]
C₁₅H₂₀N₂O [ No CAS ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 6269 - 6276

75
[ 3731-51-9 ]
[ 67111-66-4 ]
C₁₆H₂₀N₂O₃ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 6269 - 6276

76
[ 3731-51-9 ]
[ 63555-50-0 ]
methyl (R)-3-(3-(hydroxymethyl)-4-methylphenyl)-3-((1-(2-methoxyethyl)-1H-1,2,3-triazol-4-yl)methoxy)-2,2-dimethylpropanoate [ No CAS ]
(R)-3-(N-(5-(2-carboxy-1-((1-(2-methoxyethyl)-1H-1,2,3-triazol-4-yl)methoxy)-2-methylpropyl)-2-methylbenzyl)-N-(pyridin-2-ylmethyl)sulfamoyl)benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28.5%		To the mixture of methyl (R)-3-(3-(hydroxymethyl)-4-methylphenyl)-3-((1-(2-methoxyethyl)- 1 H-1 ,2,3-triazol-4-yl)methoxy)-2,2-dimethylpropanoate (50 mg, 0.128 mmol) in dichloromethane (0.5 ml.) was added SOCI2 (0.047 mL, 0.639 mmol). The resulting reaction mixture was stirred at ambient temperature for 30 min then was evaporated down under vacuum. The residue was dissolved in acetonitrile (2 mL) after which was added pyridin-2- ylmethanamine (0.020 mL, 0.192 mmol) and DIEA (0.089 mL, 0.51 1 mmol). The resulting reaction mixture was heated with microwave at 100 C for 1 h after which methyl 3- (chlorosulfonyl)benzoate (45.0 mg, 0.192 mmol) was added. The resulting reaction mixture was stirred at ambient temperature for 30 min after which was added more DIEA (0.089 mL, 0.511 mmol). The resulting reaction mixture was stirred at ambient temperature for 1 h then was evaporated down under vacuum. The residue was dissolved in methanol (1 mL) and was added NaOH (6.0 N) (0.170 mL, 1.022 mmol). The resulting reaction mixture was heated with microwave at 120 C for 1 h then was quenched with HCI (6.0 N) (0.170 mL, 1.022 mmol), evaporated down under vacuum, purified with reverse phase HPLC (formic acid modifier) to give the title compound (23.7 mg, 0.036 mmol, 28.5% yield). LC/MS: m/z 652.4 (M+H)+, 0.83 min (ret. time).

Reference： [1]Patent: WO2018/109649,2018,A1 .Location in patent: Page/Page column 162

77
[ 3731-51-9 ]
[ 100-49-2 ]
1-cyclohexyl-N-(pyridin-2-ylmethyl)methanamine [ No CAS ]

Reference： [1]Dalton Transactions,2018,vol. 47,p. 14033 - 14040

78
[ 3731-51-9 ]
[ 2859-68-9 ]
3-(pyridin-2-yl)-N-(pyridin-2-ylmethyl)propan-1-amine [ No CAS ]

Reference： [1]Dalton Transactions,2018,vol. 47,p. 14033 - 14040

79
[ 3731-51-9 ]
[ 23351-91-9 ]
C₂₀H₁₃BrN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In ethyl acetate; for 49h;Reflux;	In the flask,Add ethyl acetate (100 mL),2-aminomethylpyridine (22 g, 200 mmol),5-bromo-dibenzoic acid (24.3 g, 100 mmol),T3P (50mL,50percent in ethyl acetate).After stirring at room temperature for 1 hour, the temperature was raised to reflux.After 48 hours of reaction,Adjust to neutral with aqueous sodium hydroxide solution,Separating the organic layer,Dried over anhydrous sodium sulfate and concentrated.The crude product was purified by column chromatography to give the product 9.7g,The yield was 25percent.

Reference： [1]Patent: CN108658979,2018,A .Location in patent: Paragraph 0052; 0054; 0055; 0056

80
[ 3731-51-9 ]
[ 1823-59-2 ]
N,N′-di(2-picolyl)-4,4′-oxybisphthalimide [ No CAS ]

Reference： [1]CrystEngComm,2019,vol. 21,p. 207 - 217

81
[ 3731-51-9 ]
[ 149849-92-3 ]
2-chloro-N-(pyridin-2-ylmethyl)pyrimidine-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 25℃;	To a solution of 2- chloropyrimidine-4-carboxylic acid (14.0 g, 88.3 mmol, 1.0 eq) in DCM (100 mL) were added pyridin-2-ylmethanamine (11.4 g, 106 mmol, 1.2 eq), DIPEA (28.5 g, 221 mmol, 2.5 eq) and HATU (50.4 g, 132.5 mmol, 1.5 eq), the mixture was stirred at 25 C overnight. TLC and LCMSindicated completion. The mixture was cooled to 0 C, quenched with water (100 mL), and extracted with DCM (50 mL x 3). The combined organic layers were dried over sodium sulfate, concentrated and purified by silica column affording 2-chloro-N-(pyridin-2- ylmethyl)pyrimidine-4-carboxamide (5 g, 23%). ?H NMR (300 MHz, DMSO-d6): 5 9.56 (br, 1H), 9.03 (d, J= 4.8 Hz, 1H), 8.52 (d, J= 3.9 Hz, 1H), 8.05 (d, J= 4.5 Hz, 1H), 7.78-7.73 (m,1H), 7.34-7.25 (m, 2H), 4.61 (d, J= 5.7 Hz, 2H). ESI-MS (mlz): 248.9 (M+H).

Reference： [1]Patent: WO2019/10295,2019,A1 .Location in patent: Page/Page column 158

82
[ 3731-51-9 ]
[ 3747-74-8 ]
[Cu([bis(2-quinolylmethyl)-(2-pyridylmethyl)]amine)Cl]ClO₄ [ No CAS ]

Reference： [1]New Journal of Chemistry,2019,vol. 43,p. 6186 - 6196

83
[ 3731-51-9 ]
[ 5780-66-5 ]
[ 1084898-22-5 ]

Yield	Reaction Conditions	Operation in experiment
90%		Pyrazine-2-carbaldehyde (1 g, 9.25 mmol) was dissolved in methanol(90 mL) and yridine-2-methylanamine (0.96 mL, 9.25 mmol) was added by a syringe. This mixture wasstirred at 25 C for 30 min followed by rapid addition of NaBH4 (1.06 g, 27.76 mmol), and then stirredat 25 C for an additional 2 h. The solvent was evaporated under reduced pressure, water (20 mL)was added to the residue and the solution pH was adjusted to approximately 10 by adding Na2CO3solution. The mixture was extracted with CH2Cl2 (330 mL) and purified by column chromatographywith CH2Cl2/MeOH (30:1, v/v) to give the product 7, Scheme 2, as a pale-yellow oil (1.6 g, 90% yield).

Reference： [1]Molecules,2019,vol. 24

84
[ 3731-51-9 ]
[ 105-07-7 ]
C₁₄H₁₁N₃O [ No CAS ]
[ 84102-89-6 ]

Reference： [1]Inorganic Chemistry,2019,vol. 58,p. 7584 - 7592

85
[ 3731-51-9 ]
[ 119-60-8 ]
C₁₉H₂₈N₂ [ No CAS ]

Reference： [1]Inorganic Chemistry,2019,vol. 58,p. 7584 - 7592

86
[ 3731-51-9 ]
[ 119-60-8 ]
[ 91975-81-4 ]
C₁₉H₂₈N₂O [ No CAS ]

Reference： [1]Inorganic Chemistry,2019,vol. 58,p. 7584 - 7592

87
[ 590-92-1 ]
[ 3731-51-9 ]
[ 926188-82-1 ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 9979 - 9982

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
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Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
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P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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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.
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P251	Pressurized container: Do not pierce or burn, even after use.
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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.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
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Code	Phrase
P301	IF SWALLOWED:
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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.
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P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
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P372	Explosion risk in case of fire.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
P380	Evacuate area.
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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.
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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.
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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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.
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P370 + P376	In case of fire: Stop leak if safe to Do so.
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Code	Phrase
P401
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P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
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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
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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
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H281	Contains refrigerated gas; may cause cryogenic burns or injury
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Health hazards
Code	Phrase
H300	Fatal if swallowed
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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
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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
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H340	May cause genetic defects
H341	Suspected of causing genetic defects
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H351	Suspected of causing cancer
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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. 3731-51-9 ] {[proInfo.proName]}

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[ 3731-51-9 ] Synthesis Path-Upstream 1~12

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