[ CAS No. 40925-68-6 ] {[proInfo.proName]}

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2D 3D

Structure of 40925-68-6 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 40925-68-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 40925-68-6 ]

SDS Specification

Alternatived Products of [ 40925-68-6 ]

Product Details of [ 40925-68-6 ]

CAS No. :	40925-68-6	MDL No. :	MFCD00235171
Formula :	C₆H₆BrNO	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	JHRIPENGTGSNPJ-UHFFFAOYSA-N
M.W :	188.02	Pubchem ID :	351840
Synonyms :

Calculated chemistry of [ 40925-68-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	40.57
TPSA :	46.25 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.31
Log Po/w (XLOGP3) :	1.87
Log Po/w (WLOGP) :	1.74
Log Po/w (MLOGP) :	1.58
Log Po/w (SILICOS-IT) :	1.34
Consensus Log Po/w :	1.57

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.68
Solubility :	0.395 mg/ml ; 0.0021 mol/l
Class :	Soluble
Log S (Ali) :	-2.46
Solubility :	0.648 mg/ml ; 0.00344 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.32
Solubility :	0.906 mg/ml ; 0.00482 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.31

Safety of [ 40925-68-6 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 40925-68-6 ]

* 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 [ 40925-68-6 ]
Downstream synthetic route of [ 40925-68-6 ]

[ 40925-68-6 ] Synthesis Path-Upstream 1~4

1
[ 40925-68-6 ]
[ 140-89-6 ]
[ 439607-87-1 ]

Reference： [1] Patent: EP1219622, 2002, A2, . Location in patent: Page 17
[2] Patent: US2002/86871, 2002, A1,
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 3, p. 1222 - 1237

2
[ 75-15-0 ]
[ 40925-68-6 ]
[ 439607-87-1 ]

Reference： [1] Medicinal Chemistry Research, 1999, vol. 9, # 7-8, p. 631 - 642

3
[ 40925-68-6 ]
[ 1268454-23-4 ]

Reference： [1] Patent: WO2013/71272, 2013, A1,
[2] Patent: EP2792360, 2014, A1,

4
[ 40925-68-6 ]
[ 7424-54-6 ]
[ 938458-80-1 ]

Reference： [1] Journal of Organic Chemistry, 2014, vol. 79, # 13, p. 6310 - 6314

[ 40925-68-6 ] Synthesis Path-Downstream 1~10

1
[ 60-35-5 ]
[ 40925-68-6 ]
[ 5676-56-2 ]

Reference： [1]Bulletin de la Societe Chimique de France,1923,vol. <4> 33,p. 1828

2
[ 40925-68-6 ]
[ 56-81-5 ]
[ 1198-14-7 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1891,vol. <2> 44,p. 439,442
[2]Journal of Fluorescence,2018,vol. 28,p. 1121 - 1126

3
[ 40925-68-6 ]
[ 105655-01-4 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1465 - 1474
[2]Patent: WO2011/130628,2011,A1
[3]Patent: JP2015/187145,2015,A
[4]Patent: WO2014/149164,2014,A1

4
[ 1445-45-0 ]
[ 40925-68-6 ]
[ 5676-56-2 ]

Yield	Reaction Conditions	Operation in experiment
	for 1.5h;Heating / reflux;	A solution of 2-amino-4-bromophenol (1 g, 5.32 mmol) in trimethyl orthoacetate (20 [ML)] was refluxed for 1.5 hours. The reaction was then cooled and the solvent removed under reduced pressure to give 1.1 g of title compound. [C8H6BRNO] Mass (calculated): [212]; (found): [[M+H+]] = 212,214 (Br). NMR (400 MHz, dmso-d6): 2.55 (3H, s, CH3) ; 7.3 [(1H,] d, J = 8 Hz, aryl-H); 7.35 [(1H,] dd, J = 1 and 8 Hz, aryl-H); 7.75 [(1H,] d, [J] = 2 Hz, aryl-H).
	for 1.5h;Reflux;	General procedure: The 5-halogeno-2-methylbenzoxazoles were prepared by the treatment of the corresponding 2-amino-4-halogenophenol with either acetic anhydride (X = F or Cl) [14] or trimethylorthoacetate (X = Br) [15]. 2-Amino-4-chlorophenol was commercially available; 2-amino-4-fluorophenol and 2-amino-4-bromophenol were obtained by reduction of the corresponding 2-nitro-4-halogenophenol with H2/Pd [16] and SnCl2·2H2O [17], respectively. Attempts to reduce 2-nitro-4-bromophenol with H2/Pd resulted in debromination of the aromatic ring. The 2-nitro-4-halogenophenols were prepared in batches from the 4-halogenophenols by careful nitration in acetic acid at 15-20 C [18] on a small scale (2-5 g of halogenophenol). Nitration of fluorophenolrequired only 2 min, but nitration of bromophenol required 2-16 h (typically around 3 h); attempts to scale up the reaction resulted in reduced yields. Scheme 3 summarizes these synthetic routes.

Reference： [1]Patent: WO2003/99776,2003,A1 .Location in patent: Page 56
[2]International Journal of Mass Spectrometry,2013,vol. 345-347,p. 120 - 131

5
[ 40925-68-6 ]
[ 106-93-4 ]
[ 105655-01-4 ]

Yield	Reaction Conditions	Operation in experiment
19%	With potassium carbonate; In N,N-dimethyl-formamide; at 125℃; for 15h;Inert atmosphere;	To a solution of 2-amino-4-bromophenol (4e) (200.0 mg, 1.06 mmol) and K2C03 (735.3 mg, 5.32 mmol) in anhydrous DMF (3 mL) was added 1,2-dibromoethane (0.14 mL, 1.60 mmol) under argon. The resulting mixture was stirred at 125 C for 15 h. After being quenched with H20 (5 mL), the aqueous layer was extracted with EtOAc (2 x 15 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by column chromatography on silica gel (EtOAc/hexane, 10:90 to 20:80) to afford 3e (44.0 mg, 19%) as a brown oil; ?H NMR (CDC13, 400 MHz) 6.74-6.69 (2 H, m), 6.64 (1 H, d, J = 8.7 Hz), 4.22-4.20 (2 H, m), 3.89 (2 H, br),3.04-3.38 (2 H, m); ?3C NMR (CDC13, 100 MHz) 142.9, 135.0, 121.0, 118.0, 117.6, 113.1,64.9, 40.5.

Reference： [1]Heterocyclic Communications,2012,vol. 18,p. 143 - 146
[2]Patent: WO2018/183633,2018,A1 .Location in patent: Paragraph 0006; 0008; 0017;0106; 0107

6
[ 40925-68-6 ]
[ 1404480-15-4 ]

Reference： [1]Patent: WO2013/71272,2013,A1
[2]Patent: WO2013/23184,2013,A1
[3]Patent: WO2014/151147,2014,A1
[4]Patent: WO2014/151147,2014,A1
[5]Patent: EP2792360,2014,A1
[6]Patent: US2014/357651,2014,A1
[7]Patent: US2014/357651,2014,A1
[8]Patent: US9174994,2015,B2
[9]Patent: US9174994,2015,B2

7
[ 40925-68-6 ]
[ 1224844-38-5 ]

Reference： [1]Patent: WO2013/23184,2013,A1
[2]Patent: WO2013/23184,2013,A1

8
[ 40925-68-6 ]
[ 123-54-6 ]
[ 5676-56-2 ]
[ 107986-49-2 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 6310 - 6314

9
[ 68947-43-3 ]
[ 40925-68-6 ]
5-bromo-2-(1-methylpiperidin-4-yl)benzo[d]oxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With polyphosphoric acid; at 190℃; for 3.5h;Sealed tube;	To 2-amino-4-bromophenol (200 mg, 1.064 mmol) and l-methylpiperidine-4- carboxylic acid (152 mg, 1.064 mmol) in a sealed tube was added polyphosphoric acid (5 g). The vessel was sealed and the mixture heated for 3.5 hours at 190°C. The reaction mixture was cooled. To the mixture at 0°C was added dropwise 6mL of water and then aq. 10M NaOH until the pH reached ~8. To the thick purple mixture was added 30mL of ethyl acetate. The product was filtered through celite, extracted, and washed with water, brine, dried over sodium sulfate, filtered and evaporated to give 244.8mgs (74percent yield) of 5-bromo-2-(l-methylpiperidin-4-yl)benzo[d]oxazole as a tan solid. The LC/MS data was obtained on a Shimadzu analytical LCMS (ESI+) at 220nm using the following set of conditions: Waters Aquity BEH 1.7mm CI 8, 2.1 x 50mm column, with a gradient of 0- 100percentB (B = 90percent HPLC grade acetonitrile/ 0.1percent trifluoroacetic acid/ 10percent HPLC grade water), (A = 90percent HPLC grade water / 0.1 percent trifluoroacetic acid/ 10percent HPLC grade acetonitrile), in 2 minutes with a 1 minute hold at a rate of 1 mL/minute. LCMS Rt (Retention time)= 1.340 min., m/z 295.05, 297.00 (M + H), 95percent purity. NMR (500MHz, DMSO-ifc) delta 7.95 (d, J=1.9 Hz, 1H), 7.68 (d, J=8.6 Hz, 1H), 7.53 (dd, J=8.6, 1.9 Hz, 1H), 3.02 - 2.93 (m, 1H), 2.79 (m, 2H), 2.19 (s, 3H), 2.10 - 2.01 (m, 4H), 1.87 - 1.77 (m, 2H).

Reference： [1]Patent: WO2018/118848,2018,A1 .Location in patent: Page/Page column 33

10
[ 40925-68-6 ]
[ 78-39-7 ]
[ 5676-56-2 ]

Yield	Reaction Conditions	Operation in experiment
59%	at 100℃; for 6h;	[0339] Compound 8e: A solution of Comp-8d (15 g, 79.78 mmol) in 1,1,1-triethoxy ethane (75 mL) was heated at 100C for 6h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was concentrated in vacuo and the crude obtained was purified by column chromatography (silica, 100-200 mesh, 10% Ethyl acetate in Hexane) to afford 5-bromo-2-methylbenzo[d]oxazole (8e; 10 g, 59%) as a yellow solid. (0602) [0340] MS (ESI) m/e [M+H]+ Rt %: 211.95/1.93/93.3%. (0603) [0341] XH NMR (400 MHz, CDCl3) delta 2.65 (s, 3H) 7.33 - 7.37 (m, 1H) 7.39 - 7.44 (m, 1H) 7.79 (s, l

Reference： [1]Patent: WO2019/152731,2019,A1 .Location in patent: Paragraph 0339-0341

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Isomers

Technical Information

? Acidity of Phenols ? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Halogenation of Phenols ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Leuckart-Wallach Reaction ? Mannich Reaction ? Oxidation of Phenols ? Pechmann Coumarin Synthesis ? Petasis Reaction ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reimer-Tiemann Reaction ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Ugi Reaction ? Vilsmeier-Haack Reaction

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[ 40925-68-6 ]

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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. 40925-68-6 ] {[proInfo.proName]}

Quality Control of [ 40925-68-6 ]

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Calculated chemistry of [ 40925-68-6 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 40925-68-6 ]

[ 40925-68-6 ] Synthesis Path-Upstream 1~4

[ 40925-68-6 ] Synthesis Path-Downstream 1~10

Technical Information

Related Functional Groups of [ 40925-68-6 ]

Aryls

Bromides

Amines

Precautionary Statements-General

Prevention

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Physical hazards

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Inquiry

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[ 40925-68-6 ]