[ CAS No. 5498-31-7 ] {[proInfo.proName]}

Name: 5498-31-7|1-Bromo-3-hydroxynaphthalene|95%
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Quality Control of [ 5498-31-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 5498-31-7 ]

SDS Specification

Alternatived Products of [ 5498-31-7 ]

Product Details of [ 5498-31-7 ]

CAS No. :	5498-31-7	MDL No. :	MFCD01712260
Formula :	C₁₀H₇BrO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PQNQMYMGUXGWTG-UHFFFAOYSA-N
M.W :	223.07	Pubchem ID :	12115596
Synonyms :

Calculated chemistry of [ 5498-31-7 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	53.67
TPSA :	20.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.52 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.06
Log Po/w (XLOGP3) :	3.02
Log Po/w (WLOGP) :	3.31
Log Po/w (MLOGP) :	3.24
Log Po/w (SILICOS-IT) :	3.16
Consensus Log Po/w :	2.96

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.74
Solubility :	0.0404 mg/ml ; 0.000181 mol/l
Class :	Soluble
Log S (Ali) :	-3.11
Solubility :	0.173 mg/ml ; 0.000776 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.36
Solubility :	0.0098 mg/ml ; 0.000044 mol/l
Class :	Moderately soluble

Medicinal Chemistry

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

Safety of [ 5498-31-7 ]

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

Application In Synthesis of [ 5498-31-7 ]

* 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.

Downstream synthetic route of [ 5498-31-7 ]

[ 5498-31-7 ] Synthesis Path-Downstream 1~52

1
[ 33670-68-7 ]
[ 5498-31-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium tetrahydroborate; In ethanol; at 0℃; for 3h;	This procedure was adapted from MacLean et al6To a suspension of zwitterion 30o (4.96 g, 19.9 mmol) in EtOH (100 mL) cooled to 0 C was slowly added sodium borohydride (791 mg, 20.9 mmol). After 3 hours at 0 C, the mixture was poured into 300 mL of ice water. Once the ice melted, the product was extracted with EtOAc (150 mL). The organic phase was dried over anhydrous Na2S04 and concentrated under reduced pressure to afford 31o as a black solid (4.37 g, 98% yield). Rf= 0.46 (hexanes/EtOAc 75:25 v/v). 1H NMR (400 MHz, DMSO-d6) delta 10.11 (br s, 1H), 7.97 (d, J= 8.3 Hz, 1H), 7.76 (d, J = 8.0 Hz, 1H), 7.51-7.45 (m, 2H), 7.44-7.38 (m, 1H), 7.20 (d, J= 1.7 Hz, 1H).13C NMR (151 MHz, DMSO-d6) delta 155.1, 135.3, 127.2, 126.9, 126.0, 125.8, 124.5, 122.4, 122.2, 109.3. MS (ESI+) calculated for [Ci0H8BrO]+[M+H]+, 223.0; found 223.0.
	With sodium tetrahydroborate; ethanol;	The requisite naphthols were prepared as shown in Schemes 1 - 4. Thus, 4-bromo- 2-naphthol 1 was prepared by sequential bromination, diazotisation and reduction of 1- naphthylamine according to the published procedure (M. S. Newman, V. Sankaran and D. Olson, J. Am. Chem. Soc, 1976, 98, 3237) as shown in Scheme 1.
	With sodium tetrahydroborate; ethanol;	The requisite naphthols were prepared as shown in Schemes 1 - 4. Thus, 4-bromo-2-naphthol 1 was prepared by sequential bromination, diazotisation and reduction of 1- naphthylamine according to the published procedure (M. S. Newman, V. Sankaran and D. Olson, J. Am. Chem. Soc, 1976, 98, 3237) as shown in Scheme 1.

	With sodium tetrahydroborate; In ethanol; at 13 - 18℃; for 4h;	To a solution of 4-bromo-l-diazonio-naphthalen-2- olate (100 g, 402 mmol, 1.00 eq) in EtOH (2.00 L) was added portionwise NaBH4 (30.4 g, 803 mmol, 2.00 eq) at 13-15 C over 1 h, and the reaction mixture was stirred at 15-18 C for 3 hrs. The reaction was filtered and concentrated to dryness. The residue was dissolved in DCM (1000 mL) and washed with water (500 mL chi 2). The organic phase was dried over Na2S04 and concentrated to dryness. The residue was purified by silica gel column chromatograph, eluting with diethyl ether/ethyl acetate (60: 1 to 10: 1). The isolated product was further purified by reversed phase HPLC to provide 4-bromonaphthalen-2-ol (40.0 g, 139 mmol, 17.3 % yield, 77.4% purity) as a gray solid. MR (400 MHz, CDCh) delta 8.07 - 8.05 (d, J=8.0 Hz, 1H), 7.60 - 7.58 (d, J=7.6 Hz, 1H), 7.41 - 7.36 (m, 3H), 7.07 (s, 1H).
	With sodium tetrahydroborate; ethanol; at 13 - 18℃; for 4h;	To a solution of 4-bromo-1-diazonio-naphthalen-2-olate (100 g, 402 mmol, 1.00 eq) in EtOH (2.00 L) was added portionwise NaBH 4 (30.4 g, 803 mmol, 2.00 eq) at 13-15° C. over 1 h, and the reaction mixture was stirred at 15-18° C. for 3 hrs. The reaction was filtered and concentrated to dryness. The residue was dissolved in DCM (1000 mL) and washed with water (500 mL 2). The organic phase was dried over Na 2SO 4 and concentrated to dryness. The residue was purified by silica gel column chromatograph, eluting with diethyl ether/ethyl acetate (60:1 to 10:1). The isolated product was further purified by reversed phase HPLC to provide 4-bromonaphthalen-2-ol (40.0 g, 139 mmol, 17.3% yield, 77.4% purity) as a gray solid. 1H NMR (400 MHz, CDCl 3) delta 8.07-8.05 (d, J=8.0 Hz, 1H), 7.60-7.58 (d, J=7.6 Hz, 1H), 7.41-7.36 (m, 3H), 7.07 (s, 1H).
	With sodium tetrahydroborate; In ethanol; at 13 - 18℃; for 4h;	To a solution of 4-bromo- l-diazonio-naphthalen-2- olate (100 g, 402 mmol, 1.00 eq) in EtOH (2.00 L) was added portionwise NaBHi (30.4 g, 803 mmol, 2.00 eq) at 13-15 C over 1 h, and the reaction mixture was stirred at 15-18 C for 3 hrs. The reaction was filtered and concentrated to dryness. The residue was dissolved in DCM (1000 mL) and washed with water (500 mL c 2). The organic phase was dried over Na2S04 and concentrated to dryness. The residue was purified by silica gel column chromatograph, eluting with diethyl ether/ethyl acetate (60: 1 to 10:1). The isolated product was further purified by reverse phase HPLC to provide 4-bromonaphthalen-2-ol (40.0 g, 139 mmol, 17.3 % yield, 77.4% purity) as a gray solid. NMR (400 MHz, CDCl3) d 8.07 - 8.05 (d, .7=8.0 Hz, 1H), 7.60 - 7.58 (d, ,7=7.6 Hz, 1H), 7.41 - 7.36 (m, 3H), 7.07 (s, 1H).

Reference： [1]ChemMedChem,2018,vol. 13,p. 1092 - 1097
[2]Patent: WO2019/178480,2019,A1 .Location in patent: Page/Page column 100; 101; 102
[3]Journal of the Chemical Society,1943,p. 468
[4]Journal of the Chemical Society,1943,p. 468
[5]Patent: WO2008/28930,2008,A1 .Location in patent: Page/Page column 7
[6]Patent: WO2008/29194,2008,A1 .Location in patent: Page/Page column 6
[7]Patent: WO2017/201161,2017,A1 .Location in patent: Paragraph 0217; 0248
[8]Patent: US2019/144444,2019,A1 .Location in patent: Paragraph 0358
[9]Patent: WO2020/47192,2020,A1 .Location in patent: Paragraph 0253; 0255; 0278; 0280

2
[ 5498-31-7 ]
[ 77-78-1 ]
[ 5111-34-2 ]

Yield	Reaction Conditions	Operation in experiment
41%	With sodium hydroxide; In water; for 24h;	To a suspension of naphthol 31o (1.77 g, 7.93 mmol) in water (20 mL) at room temperature was added NaOH (dissolved in 50 mL water, 634 mg, 15.9 mmol). The contents were stirred until all solids were dissolved before the dropwise addition of dimethyl sulfate (1.50 mL, 15.9 mmol). After 24 hours of stirring, the reaction mixture was washed with diethyl ether (125 mL). The organic phase was dried over anhydrous Na2S04 and concentrated under reduced pressure. Purification by flash column chromatography (hexanes to 90: 10 hexanes/EtOAc) afforded 32o as a white solid (766 mg, 41% yield). Rf= 0.48 (hexanes/EtOAc 90: 10 v/v).1H NMR (400 MHz, CDCl3) delta 8.14 (d, J= 8.1 Hz, 1H), 7.72 (d, J= 7.7 Hz, 1H), 7.50 (d, = 2.3 Hz, 1H), 7.49-7.41 (m, 2H), 7.12 (d, J= 2.1 Hz, 1H), 3.92 (s, 3H).13C NMR (101 MHz, CDCl3) delta 157.3, 135.3, 127.8, 127.3, 127.3, 127.1, 125.1,123.6, 122.8, 106.2, 55.7.

Reference： [1]ChemMedChem,2018,vol. 13,p. 1092 - 1097
[2]Patent: WO2019/178480,2019,A1 .Location in patent: Page/Page column 102; 103
[3]Bulletin of the Chemical Society of Japan,1975,vol. 48,p. 3347 - 3355

3
[ 5498-31-7 ]
[ 178065-22-0 ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 4596 - 4600
Angew. Chem.,2019,vol. 131,p. 4644 - 4648,5
[2]Tetrahedron Letters,1996,vol. 37,p. 2979 - 2982
[3]Tetrahedron Asymmetry,1996,vol. 7,p. 2251 - 2262

4
[ 2591-86-8 ]
[ 5498-31-7 ]
[ 91136-43-5 ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 5821 - 5830

5
[ 5498-31-7 ]
[ 3923-52-2 ]
[ 227471-77-4 ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 5821 - 5830
[2]European Journal of Organic Chemistry,2003,p. 2799 - 2812

6
[ 5498-31-7 ]
[ 355408-55-8 ]
4-(thien-2-yl)naphth-2-ol [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2003,p. 2799 - 2812

7
[ 5498-31-7 ]
[ 320381-92-8 ]
[ 583886-91-3 ]

Reference： [1]European Journal of Organic Chemistry,2003,p. 2799 - 2812

8
[ 5498-31-7 ]
[ 1499-21-4 ]
[ 864423-16-5 ]