[ CAS No. 59786-31-1 ] {[proInfo.proName]}

Name: 59786-31-1|Methyl 3-bromoisonicotinate|98%
Brand: Ambeed
SKU: A272551
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Quality Control of [ 59786-31-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 59786-31-1 ]

SDS Specification

Alternatived Products of [ 59786-31-1 ]

Product Details of [ 59786-31-1 ]

CAS No. :	59786-31-1	MDL No. :	MFCD03788226
Formula :	C₇H₆BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FASOJOLGUAUEPU-UHFFFAOYSA-N
M.W :	216.03	Pubchem ID :	2762700
Synonyms :

Calculated chemistry of [ 59786-31-1 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	43.22
TPSA :	39.19 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.86
Log Po/w (XLOGP3) :	1.4
Log Po/w (WLOGP) :	1.63
Log Po/w (MLOGP) :	1.09
Log Po/w (SILICOS-IT) :	1.87
Consensus Log Po/w :	1.57

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.33
Solubility :	1.0 mg/ml ; 0.00464 mol/l
Class :	Soluble
Log S (Ali) :	-1.83
Solubility :	3.22 mg/ml ; 0.0149 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.96
Solubility :	0.237 mg/ml ; 0.0011 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.49

Safety of [ 59786-31-1 ]

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

Application In Synthesis of [ 59786-31-1 ]

* 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 [ 59786-31-1 ]
Downstream synthetic route of [ 59786-31-1 ]

[ 59786-31-1 ] Synthesis Path-Upstream 1~10

1
[ 67-56-1 ]
[ 13959-02-9 ]
[ 59786-31-1 ]

Yield	Reaction Conditions	Operation in experiment
62%	Heating / reflux	A mixture of 3.98 g of the acid obtained in the previous step (20 mmol, 1 eq.) in 50 ml of methanol is reflux heated in the presence of 4 ml of concentrated sulfuric acid. The mixture is allowed to return to ambient temperature and extracted 3 times with ethyl acetate. The organic phase is dried on Na₂SO₄and the solvent is evaporated. 2.65 g (62percent) of esterified product is obtained. NMR (¹H, CDCl₃): 4.02 (s; 3H), 7.64 (d, J=4.9 Hz; 1H), 8.63 (d, J=4.9 Hz; 1H), 8.88 (s; 1H).

Reference： [1] Patent: US2005/80085, 2005, A1, . Location in patent: Page/Page column 12
[2] Patent: US2010/130477, 2010, A1, . Location in patent: Page/Page column 58
[3] Patent: US2011/230495, 2011, A1, . Location in patent: Page/Page column 23-24
[4] Advanced Synthesis and Catalysis, 2016, vol. 358, # 20, p. 3283 - 3292

2
[ 186581-53-3 ]
[ 13959-02-9 ]
[ 59786-31-1 ]

Yield	Reaction Conditions	Operation in experiment
66%	at 0 - 20℃; for 1 h; Inert atmosphere	To a stirred solution of 3-bromoisonicotinic acid 1 (2 g, 9.90 mmol) in MeOH: THF(2: 1, 30 mL) under argon atmosphere was added CH2N2 (2 g, 49.50 mmol) at 0 °C; warmed toRT and stirred for 1 h. The reaction was monitored by TLC; after completion of the reaction, the volatiles were removed in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 20percent EtOAc/ hexanes to afford compound 2 (1.4 g, 66percent) as brown oil. TLC: 20percent EtOAc/ hexanes (R 0.7); ‘H-NMR (CDC13, 400 MHz): ö 8.87 (s, 1H),8.62 (d, J = 7.2 Hz, 1H), 7.63 (d, J = 5.6 Hz, 1H), 3.97 (s, 3H).

Reference： [1] Patent: WO2018/53157, 2018, A1, . Location in patent: Page/Page column 83

3
[ 124-38-9 ]
[ 74-88-4 ]
[ 59786-31-1 ]

Reference： [1] Patent: WO2006/4195, 2006, A1, . Location in patent: Page/Page column 70; 130

4
[ 74-88-4 ]
[ 59786-31-1 ]

Reference： [1] Patent: WO2006/30984, 2006, A1, . Location in patent: Page/Page column 56-57; 129

5
[ 13959-02-9 ]
[ 18107-18-1 ]
[ 59786-31-1 ]

Reference： [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 14, p. 3878 - 3882[2] Angew. Chem., 2013, vol. 125, # 14, p. 4132
[3] Organic and Biomolecular Chemistry, 2016, vol. 14, # 24, p. 5820 - 5825

6
[ 13959-02-9 ]
[ 59786-31-1 ]

Reference： [1] Patent: US5294610, 1994, A,

7
[ 3034-31-9 ]
[ 59786-31-1 ]

Reference： [1] Synthetic Communications, 1997, vol. 27, # 6, p. 1075 - 1086

8
[ 71541-34-9 ]
[ 59786-31-1 ]

Reference： [1] Synthetic Communications, 1997, vol. 27, # 6, p. 1075 - 1086

9
[ 13959-02-9 ]
[ 74-88-4 ]
[ 59786-31-1 ]

Reference： [1] Synthetic Communications, 1997, vol. 27, # 6, p. 1075 - 1086

10
[ 626-55-1 ]
[ 67-56-1 ]
[ 124-38-9 ]
[ 59786-31-1 ]

Reference： [1] Patent: US6335343, 2002, B1, . Location in patent: Page column 50

[ 59786-31-1 ] Synthesis Path-Downstream 1~88

1
[ 2935-90-2 ]
[ 59786-31-1 ]
3-(2-Methoxycarbonyl-ethylsulfanyl)-isonicotinic acid methyl ester [ No CAS ]

Reference： [1]Zeitschrift fur Chemie,1988,vol. 28,p. 248 - 249

2
[ 59786-31-1 ]
[ 2365-48-2 ]
[ 111042-97-8 ]

Yield	Reaction Conditions	Operation in experiment
59%		A mixture of 2.65 g of the product from the previous step (12 mmol, 1 eq.) with 1.1 ml of methyl thioglycolate (12 mmol, 1 eq.) in 100 ml of acetonitrile is reflux heated for 18 hrs in the presence of 2.54 g of potassium carbonate (18 mmol, 1.5 eq.). After that, the mixture is allowed to return to ambient temperature, the solvent is evaporated and the residue is dissolved in water. A few ml of acetic acid (pH 4) are added and the precipitate formed is filtered. It is vacuum dried. 1.51 g (59percent) of aromatized product is obtained. NMR (1H, CDCl3): 4.00 (s; 3H), 7.63 (d, J=4.9 Hz; 1H), 8.58 (d, J=4.9 Hz; 1H), 9.10 (s; 1H), 10.02 (s; 1H)

Reference： [1]Patent: US2005/80085,2005,A1 .Location in patent: Page/Page column 13
[2]Journal of Heterocyclic Chemistry,1987,vol. 24,p. 85 - 89

3
[ 59786-31-1 ]
[ 114080-98-7 ]

Reference： [1]Zeitschrift fur Chemie,1987,vol. 27,p. 337 - 338

4
[ 13959-02-9 ]
[ 74-88-4 ]
[ 59786-31-1 ]

Reference： [1]Synthetic Communications,1997,vol. 27,p. 1075 - 1086

6
[ 59786-31-1 ]
[ 98-80-6 ]
[ 850162-87-7 ]