[ CAS No. 2398-37-0 ] {[proInfo.proName]}

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Quality Control of [ 2398-37-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 2398-37-0 ]

SDS Specification

Alternatived Products of [ 2398-37-0 ]

Product Citations Expand+

Matrix-Designed Bright Near-Infrared Fluorophores for Precision Peripheral Nerve Imaging

Monta?o, Antonio R ; Masillati, Anas ; Szafran, Dani A , et al. Biomaterials,2025,319,123190. DOI: 10.1016/j.biomaterials.2025.123190

Abstract: The FDA's recent approval of pafolacianine, the first molecular targeted contrast agent for fluorescence-guided surgery (FGS), signifies a remarkable milestone in precision medicine. This advance offers new hope for cancer patients by enabling guided removal of cancerous tissues, where completed surgical removal remains a consistent challenge without real-time intraoperative guidance. For optimal surgical outcomes, delicate nerve tissues must be preserved to maintain patient quality of life. Despite advances in the clinical translation pipeline, the development of clinically viable nerve-specific contrast agents for FGS remains a significant challenge. Herein, a medicinal chemistry-based matrix design strategy was applied to effectively generate a synthetic roadmap permitting management of nerve-specificity within the near-infrared (NIR) oxazine fluorophore family. Many of these newly developed fluorophores demonstrated robust nerve-specificity and superior safety profiles, while also offering spectral profiles that are compatible with the clinical surgical FGS infrastructure. Notably, improving observed brightness in vivo enabled exceptional visibility of buried nerve tissue, a priority during surgical procedures. Critically, the lead probe showed a large dosage safety window capable of generating substantial contrast at doses 100x lower than the maximum tolerated dose. Following clinical translation, such NIR nerve-specific fluorophores stand poised to significantly improve outcomes for surgical patients by improving identification and visualization of surface and buried nerve tissues in real time within the surgical arena.

Keywords: Near-infrared (NIR) ; Fluorescence imaging ; Oxazine ; Nerve-specific imaging ; Fluorescence-guided surgery (FGS)

Purchased from AmBeed: 2398-37-0 ; 99-07-0 ; 91-68-9 ; 102-56-7

Product Details of [ 2398-37-0 ]

CAS No. :	2398-37-0	MDL No. :	MFCD00000081
Formula :	C₇H₇BrO	Boiling Point :	-
Linear Structure Formula :	BrC₆H₄(OCH₃)	InChI Key :	PLDWAJLZAAHOGG-UHFFFAOYSA-N
M.W :	187.03	Pubchem ID :	16971
Synonyms :

Calculated chemistry of [ 2398-37-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	40.63
TPSA :	9.23 ?2

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) :	-5.29 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.29
Log Po/w (XLOGP3) :	3.03
Log Po/w (WLOGP) :	2.46
Log Po/w (MLOGP) :	2.57
Log Po/w (SILICOS-IT) :	2.52
Consensus Log Po/w :	2.57

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.34
Solubility :	0.0863 mg/ml ; 0.000461 mol/l
Class :	Soluble
Log S (Ali) :	-2.89
Solubility :	0.241 mg/ml ; 0.00129 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.38
Solubility :	0.0783 mg/ml ; 0.000419 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.36

Safety of [ 2398-37-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H227-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 2398-37-0 ]

* 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 [ 2398-37-0 ]
Downstream synthetic route of [ 2398-37-0 ]

[ 2398-37-0 ] Synthesis Path-Upstream 1~1

1
[ 2398-37-0 ]
[ 28547-28-6 ]

Reference： [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 14, p. 5917 - 5930

[ 2398-37-0 ] Synthesis Path-Downstream 1~17

1
[ 2398-37-0 ]
[ 62171-59-9 ]
2-(3-Methoxy-phenyl)-8,8-dimethyl-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-triene [ No CAS ]

Reference： [1]Angewandte Chemie,1994,vol. 106,p. 117 - 119

2
[ 2398-37-0 ]
[ 121554-09-4 ]
[ 260056-62-0 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 1593 - 1601

3
[ 2398-37-0 ]
[ 547-63-7 ]
[ 32454-33-4 ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 12557 - 12565
[2]Organic Letters,2008,vol. 10,p. 1545 - 1548

4
[ 2398-37-0 ]
[ 6933-49-9 ]

Reference： [1]Journal of Chemical Research, Miniprint,1986,p. 2645 - 2696

5
[ 2398-37-0 ]
[ 1126-46-1 ]
[ 792-74-5 ]
[ 81443-43-8 ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 2089 - 2092

6
[ 6563-13-9 ]
[ 2398-37-0 ]
[ 476159-12-3 ]

Yield	Reaction Conditions	Operation in experiment
47%		To 231 mg (9.63 mmol, 6 eq) of purified magnesium in 10 ml of dry ether are added two crystals of iodine and 1.5 g (8.02 mmol, 5 eq) of bromoanisole dissolved in 10 ml of dry ether. The reaction mixture is boiled under reflux and under nitrogen atmosphere at 30 C. for 2 h.Coupling: 281 mg (1.60 mmol, 1 eq) of 6-methoxyquinoline-N-oxide dissolved in 80 ml of toluene is added to the Grignard mixture, and the mixture is heated at 90 C. for 2 h. After cooling the round-bottom flask, the reaction mixture is added on ice, and after the ice is molten, 2 N hydrochloric acid and water are added until the precipitate formed has dissolved. The water phase is washed with ether and made alkaline with KOH. After extraction with chloroform, the combined organic phases are dried over magnesium sulfate, filtered, and the solvent is removed in vacuum on a rotary evaporator. Purification was performed by means of column chromatography with hexane/ethyl acetate 95/5 as the eluent to obtain the desired product in a yield of 47% (199 mg).C17H15NO2; MW 265; 1H-NMR (CDCl3): δ 7.91 (d, J=1.5 Hz, 1H), 7.89 (s, 1H), 7.62 (d, J=8.8 Hz, 1H); 7.57 (t, J=2.4 Hz, 1H), 7.50 (d, J=7.9 Hz, 1H), 7.24 (t, J=7.9 Hz, 1H), 7.20 (dd, J=2.7 Hz, J=9.1 Hz, 1H), 6.89 (d, J=2.7 Hz, 1H), 6.82 (dd, J=2.7 Hz, J=8.2 Hz, 1H), 3.75 (s, 3H), 3.74 (s, 3H); 13C-NMR (CDCl3): δ 160.1, 157.7, 154.8, 144.3, 141.3, 135.5, 131.1, 129.8, 128.3, 122.4, 119.8, 119.4, 115.0, 112.5, 105.0, 55.5, 55.4; IR: 2964, 2839, 1621, 1600, 1583, 1559, 1478, 1455, 1430 1/cm; MS (ESI): 266 (M+H)+

Reference： [1]Patent: US2010/204234,2010,A1 .Location in patent: Page/Page column 17

7
[ 2398-37-0 ]
[ 1238951-37-5 ]
[ 1238951-42-2 ]

Reference： [1]ACS Medicinal Chemistry Letters,2010,vol. 1,p. 365 - 369

8
[ 35852-81-4 ]
[ 2398-37-0 ]
[ 1252831-36-9 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 4924 - 4927

9
[ 2398-37-0 ]
[ 97308-23-1 ]
[ 1190890-94-8 ]

Reference： [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 5370 - 5383

10
[ 2398-37-0 ]
[ 105-53-3 ]
[ 35553-92-5 ]

Reference： [1]Advanced Synthesis and Catalysis,2011,vol. 353,p. 1565 - 1574
[2]Organic Letters,2022,vol. 24,p. 115 - 120

11
[ 2398-37-0 ]
[ 6148-64-7 ]
[ 35553-92-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With dmap; bis(η3-allyl-μ-chloropalladium(II)); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,3,5-trimethyl-benzene; at 140℃; for 20h;Inert atmosphere;	General procedure: after standard cycles of evacuation and back-filling with dry and pure nitrogen, an oven-dried Schlenk tube equipped with a magnetic stirring bar was charged with Pd source (see Table 1, Table 2, Table 3 and Table 4), ligand (see Table 1, Table 2, Table 3 and Table 4), N,N-dimethylpyridin-4-amine (DMAP, see Table 1, Table 2, Table 3 and Table 4), and ethyl potassium malonate (see Table 1, Table 2, Table 3 and Table 4). The tube was evacuated and backfilled with argon (this procedure was repeated three times). Under a counter flow of argon, aryl halide (see Table 1, Table 2, Table 3 and Table 4) and solvent (see Table 1, Table 2, Table 3 and Table 4) were added by syringe. The tube was sealed and stirred at room temperature for 10 min. Then the tube was connected to the Schlenk line, which was full of argon, stirred in a preheated oil bath (140-150 C) for the appointed time (20-25 h). Upon completion of the reaction, the mixture was cooled to room temperature and diluted with diethyl ether, and the yields were determined by gas chromatography using 1,3-dimethoxybenzene as the internal standard.

Reference： [1]Tetrahedron,2012,vol. 68,p. 2113 - 2120

12
[ 5754-35-8 ]
[ 2398-37-0 ]
[ 1538625-25-0 ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 1617 - 1627

13
[ 2398-37-0 ]
[ 547-63-7 ]
[ 32454-33-4 ]
[ 1376242-53-3 ]

Reference： [1]Organic Syntheses,2011,vol. 88,p. 4 - 13

14
[ 2398-37-0 ]
[ 381-98-6 ]
1-[(E/Z)-3,3,3-trifluoro-1-propen-1-yl]-3-methoxybenzene [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 1874 - 1877

15
[ 70199-60-9 ]
[ 2398-37-0 ]
4-(methoxy(3-methoxyphenyl)methyl)pyridine [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 1927 - 1932

16
[ 885693-20-9 ]
[ 2398-37-0 ]
tert-butyl 3-(3-methoxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; water; caesium carbonate; In 1,4-dioxane; at 80℃;	To a solution of tert- butyl 3-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-5,6 - dihydropyridine-1 (2/-/)-carboxylate (10.92 g, 35 mmol), 1 -bromo-3-methoxybenzene (6.6 g, 35 mmol) and Cs2C03 (3.44 g, 106 mmol) in 1 ,4-dioxane (50 ml.) and H20 (10 ml.) was added Pd(dppf)CI2 (1 .32 g, 1 .75 mmol). The reaction mixture was stirred overnight at 80 C. The solvent was removed. The residue was purified by column chromatography (petroleum ether/EtOAc = 10:1 ) to provide tert- butyl 3-(3-methoxyphenyl)-5,6-dihydropyridine-1 {2H)- carboxylate. LC-MS (ESI): m/z 290.12 [M+H] +. 1 H NMR (400 MHz, CDCI3): d 7.26 (m, 1 H), 6.96 (m, 1 H), 6.89 (s, 1 H), 6.81 (m, 1 H), 6.19 (s, 1 H), 4.25 (s, 2H), 3.81 (s, 3H), 3.54 (m, 2H), 2.30 (s, 2H), 1 .49 (s, 9H).

Reference： [1]Patent: WO2019/178510,2019,A1 .Location in patent: Paragraph 00254

17
[ 2398-37-0 ]
[ 5764-82-9 ]
[ 35553-92-5 ]

Reference： [1]Angewandte Chemie - International Edition,2021,vol. 60,p. 6778 - 6783
Angew. Chem.,2021,vol. 133,p. 6852 - 6858,7

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Nomenclature of Ethers ? Preparation of Alkylbenzene ? Preparation of Ethers ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reactions of Ethers ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Vilsmeier-Haack Reaction

Historical Records

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[ 2398-37-0 ]

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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

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[ CAS No. 2398-37-0 ] {[proInfo.proName]}

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[ 2398-37-0 ] Synthesis Path-Upstream 1~1

[ 2398-37-0 ] Synthesis Path-Downstream 1~17

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Aryls

Bromides

Ethers

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[ 2398-37-0 ]