[ CAS No. 100523-96-4 ] {[proInfo.proName]}

Name: 100523-96-4|2-Bromo-4-iodopyridine|98%
Brand: Ambeed
SKU: A239360
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Quality Control of [ 100523-96-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 100523-96-4 ]

SDS Specification

Alternatived Products of [ 100523-96-4 ]

Product Details of [ 100523-96-4 ]

CAS No. :	100523-96-4	MDL No. :	MFCD03085768
Formula :	C₅H₃BrIN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HPKRNLGLZYOVJS-UHFFFAOYSA-N
M.W :	283.89	Pubchem ID :	1051520
Synonyms :

Calculated chemistry of [ 100523-96-4 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	44.65
TPSA :	12.89 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) :	-6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.01
Log Po/w (XLOGP3) :	2.53
Log Po/w (WLOGP) :	2.45
Log Po/w (MLOGP) :	2.18
Log Po/w (SILICOS-IT) :	3.09
Consensus Log Po/w :	2.45

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.75
Solubility :	0.0506 mg/ml ; 0.000178 mol/l
Class :	Soluble
Log S (Ali) :	-2.45
Solubility :	1.01 mg/ml ; 0.00357 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.82
Solubility :	0.0427 mg/ml ; 0.00015 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.17

Safety of [ 100523-96-4 ]

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 [ 100523-96-4 ]

* 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 [ 100523-96-4 ]
Downstream synthetic route of [ 100523-96-4 ]

[ 100523-96-4 ] Synthesis Path-Upstream 1~12

1
[ 265981-13-3 ]
[ 100523-96-4 ]

Reference： [1] Synthesis, 2004, # 16, p. 2614 - 2616
[2] Angewandte Chemie - International Edition, 2008, vol. 47, # 9, p. 1662 - 1667

2
[ 109-04-6 ]
[ 100523-96-4 ]

Reference： [1] Journal of the American Chemical Society, 2012, vol. 134, # 5, p. 2653 - 2671

3
[ 109-04-6 ]
[ 100523-96-4 ]
[ 73290-22-9 ]
[ 1353056-31-1 ]
[ 234111-08-1 ]
[ 265981-13-3 ]

Reference： [1] Chemistry - A European Journal, 2011, vol. 17, # 47, p. 13284 - 13297

4
[ 109-04-6 ]
[ 100523-96-4 ]
[ 1353056-31-1 ]
[ 234111-08-1 ]
[ 265981-13-3 ]

Reference： [1] Chemistry - A European Journal, 2011, vol. 17, # 47, p. 13284 - 13297

5
[ 7598-35-8 ]
[ 100523-96-4 ]

Reference： [1] Roczniki Chemii, 1957, vol. 31, p. 569,574[2] Chem.Abstr., 1958, p. 5407

6
[ 14305-17-0 ]
[ 100523-96-4 ]

Reference： [1] Roczniki Chemii, 1957, vol. 31, p. 569,574[2] Chem.Abstr., 1958, p. 5407

7
[ 52092-43-0 ]
[ 100523-96-4 ]

Reference： [1] Roczniki Chemii, 1957, vol. 31, p. 569,574[2] Chem.Abstr., 1958, p. 5407

8
[ 109-04-6 ]
[ 100523-96-4 ]
[ 73290-22-9 ]
[ 1353056-31-1 ]
[ 234111-08-1 ]
[ 265981-13-3 ]

Reference： [1] Chemistry - A European Journal, 2011, vol. 17, # 47, p. 13284 - 13297

9
[ 109-04-6 ]
[ 100523-96-4 ]
[ 73290-22-9 ]
[ 1353056-31-1 ]
[ 234111-08-1 ]
[ 265981-13-3 ]

Reference： [1] Chemistry - A European Journal, 2011, vol. 17, # 47, p. 13284 - 13297

10
[ 109-04-6 ]
[ 100523-96-4 ]
[ 1353056-31-1 ]
[ 234111-08-1 ]
[ 265981-13-3 ]

Reference： [1] Chemistry - A European Journal, 2011, vol. 17, # 47, p. 13284 - 13297

11
[ 109-04-6 ]
[ 100523-96-4 ]
[ 73290-22-9 ]
[ 1353056-31-1 ]
[ 234111-08-1 ]
[ 265981-13-3 ]

Reference： [1] Chemistry - A European Journal, 2011, vol. 17, # 47, p. 13284 - 13297

12
[ 109-04-6 ]
[ 100523-96-4 ]
[ 1353056-31-1 ]
[ 234111-08-1 ]
[ 265981-13-3 ]

Reference： [1] Chemistry - A European Journal, 2011, vol. 17, # 47, p. 13284 - 13297

[ 100523-96-4 ] Synthesis Path-Downstream 1~88

1
[ 7598-35-8 ]
[ 100523-96-4 ]

Reference： [1]Roczniki Chemii,1957,vol. 31,p. 569,574
Chem.Abstr.,1958,p. 5407

2
[ 100523-96-4 ]
[ 223130-72-1 ]

Reference： [1]Synthetic Communications,2004,vol. 34,p. 3227 - 3233
[2]Synthesis,2004,p. 2614 - 2616

3
[ 100523-96-4 ]
4'-methyl-4-<i>p</i>-tolyl-[2,2']bipyridinyl [ No CAS ]

Reference： [1]Synthetic Communications,2004,vol. 34,p. 3227 - 3233

4
[ 109-04-6 ]
(+-)-4-dimethylamino-2-<i>p</i>-tolyl-butyronitrile [ No CAS ]
[ 100523-96-4 ]

Reference： [1]Synthesis,2004,p. 2614 - 2616

5
[ 100523-96-4 ]
[ 111971-31-4 ]

Reference： [1]Synthesis,2004,p. 2614 - 2616
[2]Synthesis,2004,p. 2614 - 2616

6
[ 100523-96-4 ]
2-phenyl-4-(p-methylphenyl)pyridine [ No CAS ]

Reference： [1]Synthesis,2004,p. 2614 - 2616

7
[ 100523-96-4 ]
2-(p-methoxyphenyl)-4-(p-chlorophenyl)pyridine [ No CAS ]

Reference： [1]Synthesis,2004,p. 2614 - 2616

8
[ 100523-96-4 ]
[ 697301-31-8 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2453 - 2465

9
[ 100523-96-4 ]
[ 697301-33-0 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2453 - 2465

10
[ 100523-96-4 ]
5-((S)-1-Azetidin-2-ylmethoxy)-3-[(E)-2-(2-bromo-pyridin-4-yl)-vinyl]-2-chloro-pyridine; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2453 - 2465

11
[ 100523-96-4 ]
3-[(E)-2-(2-Bromo-pyridin-4-yl)-vinyl]-2-chloro-5-((S)-1-pyrrolidin-2-ylmethoxy)-pyridine; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2453 - 2465

12
[ 14305-17-0 ]
[ 100523-96-4 ]

Reference： [1]Roczniki Chemii,1957,vol. 31,p. 569,574
Chem.Abstr.,1958,p. 5407

13
[ 52092-43-0 ]
[ 100523-96-4 ]

Reference： [1]Roczniki Chemii,1957,vol. 31,p. 569,574
Chem.Abstr.,1958,p. 5407

14
[ 100523-96-4 ]
[ 89343-06-6 ]
[ 1019994-52-5 ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 1662 - 1667

15
[ 6224-91-5 ]
[ 100523-96-4 ]
[ 1260215-32-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With copper(l) iodide; tetrabutyl ammonium fluoride; triethylamine;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; toluene; at 20℃;Inert atmosphere;	Example 55i 2-Bromo-4-(prop-1-ynyI)pyridine To a solution of <strong>[100523-96-4]2-bromo-4-iodopyridine</strong> (2 g, 7.04 mmol), copper(I) iodide (0.080 mL, 2.11 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.407 g, 0.35 mmol) in toluene (85 mL) was added l-(trimethylsilyl)-1-propyne (1.054 mL, 7.04 mmol), triethylamine (3.24 mL, 23.25 mmol) and tetrabutylammonium fluoride (1 M in THF, 7.04 mL, 7.04 mmol) and the resulting mixture was stirred under an argon atmosphere at roomtemperature over night. The mixture was concentrated and the resulting residue was partitioned between water (10 mL) and dichloromethane (10 mL) and poured into a phase separator. The organic phase was collected and the aqueous phase was extracted once with dichloromethane (10 mL). The combined organics were concentrated and purified by silica gel chromatography using 0% to 30% ethyl acetate in heptane to give 2-bromo-4-(prop-1-ynyl)pyridine (1.195 g, 87% yield): 1H NMR (500 MHz, DMSCM5) delta ppm 8.35 (dd, 1 H) 7.65 (s, 1 H) 7.42 (dd, 1 H) 2.11 (s, 3 H); MS (ES+) m/z 196, 198 [M+H]+; MS (APCI+) m/z 196, 198 [M+H]+
87%	With triethylamine;copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrabutyl ammonium fluoride; In toluene; at 20℃;Inert atmosphere;	Intermediate 162-Bromo-4-(prop-1-ynyl)pyridine; To a solution of <strong>[100523-96-4]2-bromo-4-iodopyridine</strong> (2 g, 7.04 mmol), copper(I) iodide (0.080 mL, 2.11 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.407 g, 0.35 mmol) in toluene (85 mL) was added 1-(trimethylsilyl)-1-propyne (1.054 mL, 7.04 mmol), triethylamine (3.24 mL, 23.25 mmol) and tetrabutylammonium fluoride (1 M in THF, 7.04 mL, 7.04 mmol) and the resulting mixture was stirred under an argon atmosphere at r.t. overnight. The mixture was concentrated and the resulting residue was partitioned between water (10 mL) and DCM (10 mL) and poured into a phase separator. The organic phase was collected, and the aqueous phase was extracted once with DCM (10 mL). The combined organics were concentrated and purified by flash chromatography using 0% to 30% EtOAc in heptane to give the title compound (1.195 g, 87% yield): 1H NMR (500 MHz, DMSO-d6) delta ppm 2.11 (s, 3H), 7.42 (dd, 1H), 7.65 (s, 1H), 8.35 (dd, 1H); MS (ES+) m/z 196 [M+H]+; MS (APCI+) m/z 196 [M+H]+.

Reference： [1]Patent: WO2011/2408,2011,A1 .Location in patent: Page/Page column 68
[2]Patent: US2012/165347,2012,A1 .Location in patent: Page/Page column 27

16
[ 100523-96-4 ]
[ 1260215-94-8 ]

Reference： [1]Patent: WO2011/2408,2011,A1

17
[ 100523-96-4 ]
[ 1260215-33-5 ]

Reference： [1]Patent: WO2011/2408,2011,A1
[2]Patent: US2012/165347,2012,A1

18
[ 100523-96-4 ]
[ 1260215-39-1 ]

Reference： [1]Patent: WO2011/2408,2011,A1

19
[ 100523-96-4 ]
[ 1268247-73-9 ]
[ 1268248-01-6 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1510 - 1513

20
[ 1239363-47-3 ]
[ 100523-96-4 ]
[ 1309880-40-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2732 - 2735

21
[ 100523-96-4 ]
[ 1309880-28-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2732 - 2735

22
[ 100523-96-4 ]
[ 1309880-29-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2732 - 2735

23
[ 100523-96-4 ]
[ 1309880-30-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2732 - 2735

24
[ 100523-96-4 ]
[ 1309880-31-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2732 - 2735

25
[ 100523-96-4 ]
[ 1309880-08-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2732 - 2735

26
[ 100523-96-4 ]
C₁₅H₁₂BrN₃O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2732 - 2735

27
[ 100523-96-4 ]
C₁₅H₉BrN₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2732 - 2735

28
[ 100523-96-4 ]
C₁₅H₁₂BrN₃S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2732 - 2735

29
[ 100523-96-4 ]
C₁₃H₉BrN₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2732 - 2735

30
[ 852475-03-7 ]
[ 100523-96-4 ]
[ 1202565-17-0 ]