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Product Details of [ 620-24-6 ]

CAS No. :620-24-6 MDL No. :MFCD00004643
Formula : C7H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :OKVJCVWFVRATSG-UHFFFAOYSA-N
M.W : 124.13 Pubchem ID :102
Synonyms :
Chemical Name :3-Hydroxybenzyl alcohol

Calculated chemistry of [ 620-24-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 34.59
TPSA : 40.46 Ų

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) : -6.71 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.31
Log Po/w (XLOGP3) : 0.49
Log Po/w (WLOGP) : 0.73
Log Po/w (MLOGP) : 0.88
Log Po/w (SILICOS-IT) : 1.22
Consensus Log Po/w : 0.92

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.35
Solubility : 5.6 mg/ml ; 0.0451 mol/l
Class : Very soluble
Log S (Ali) : -0.91
Solubility : 15.3 mg/ml ; 0.123 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.61
Solubility : 3.06 mg/ml ; 0.0247 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 620-24-6 ]

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 [ 620-24-6 ]

* 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 [ 620-24-6 ]
  • Downstream synthetic route of [ 620-24-6 ]

[ 620-24-6 ] Synthesis Path-Upstream   1~16

  • 1
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YieldReaction ConditionsOperation in experiment
93% With sodium chloride; sulfuric acid; sodium hydrogencarbonate; potassium carbonate In chlorobenzene EXAMPLE 1
m-Hydroxybenzyl alcohol (50.0 g; 0.40 mole), 90.0 g (0.80 mole) of chlorobenzene, 156.6 g (1.37 moles) of N,N'-dimethylimidazolidinone and 41.8 g (0.30 mole) of potassium carbonate were mixed, and 0.8 g of cuprous chloride and 1.2 g of 8-hydroxyquinoline were added.
The mixture was heated to 150oC in an inert gaseous atmosphere.
The mixture was stirred for 17 hours while continuing refluxing and dehydration.
During this time, the reaction temperature gradually rose and reached 162oC at the end of 17 hours.
The mixture was further heated to 170oC, and stirred for 3 hours at this temperature.
After the reaction, the reaction mixture was cooled and 200 ml of 5percent cold dilute sulfuric acid was added.
The mixture was extracted with ether, and the ethereal layer was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. GLC analysis showed that the conversion of m-hydroxybenzyl alcohol was 100 percent, the selectivity of m-phenoxybenzyl alcohol was 93 percent, and the yield of m-phenoxybenzyl alcohol was 93 percent.
Reference: [1] Patent: EP202838, 1991, B1,
[2] Patent: US4694110, 1987, A,
  • 2
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Reference: [1] Patent: US5068459, 1991, A,
[2] Patent: US4694110, 1987, A,
[3] Patent: EP202838, 1991, B1,
[4] Patent: US4694110, 1987, A,
[5] Patent: EP202838, 1991, B1,
  • 3
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  • [ 112-35-6 ]
  • [ 13826-35-2 ]
Reference: [1] Patent: US5068459, 1991, A,
  • 4
  • [ 108-86-1 ]
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  • [ 13826-35-2 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 9, p. 4964 - 4969
  • 5
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  • [ 108-90-7 ]
  • [ 13826-35-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 21, p. 6211 - 6215[2] Angew. Chem., 2016, vol. 128, p. 6319 - 6323,5
[3] Chemistry Letters, 1988, p. 899 - 900
[4] Chemistry Letters, 1988, p. 899 - 900
  • 6
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  • [ 618-49-5 ]
Reference: [1] Catalysis Communications, 2012, vol. 26, p. 48 - 53
  • 7
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  • [ 2737-19-1 ]
  • [ 2316-63-4 ]
Reference: [1] Phytochemistry, 1994, vol. 37, # 2, p. 307 - 310
  • 8
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  • [ 49617-80-3 ]
YieldReaction ConditionsOperation in experiment
87 % With hydrogen bromide; acetic anhydride In pyridine; dichloromethane; water; acetic acid m-(Bromomethyl)phenyl acetate
m-Hydroxybenzyl alcohol (37.2 g, 0.3 mole) was dissolved in 100 ml pyridine and acetic anhydride (81.7 g, 0.8 mole) added to the stirred solution proportional as the temperature rose to 70° C.
After stirring for a half hour the solution was poured over ice and hydrochloric acid.
The product oil was separated and the aqueous solution shaken twice with dichloromethane.
The oil and dichloromethane extracts were combined and washed with bicarbonate solution, water, dilute acid and water again.
The extract was dried over magnesium sulfate, filtered, and the solvent evaporated, yielding 55.7 g crude oil (87 percent).
This oil was then treated with 150 g 30-32 percent hydrogen bromide in acetic acid for 10 min. and then 25 ml acetic anhydride was added.
The mixture was allowed to stand overnight at room temperature.
The solution was evaporated under reduced pressure to an oil.
The oil was dissolved in dichloromethane and washed in turn with water, aqueous sodium bicarbonate, and water.
The dichloromethane solution was dried with magnesium sulfate, filtered and evaporated.
On standing in a refrigerator for a week the oil finely crystallized.
Reference: [1] Tetrahedron, 2000, vol. 56, # 29, p. 5169 - 5175
[2] Patent: US4476207, 1984, A,
  • 9
  • [ 620-24-6 ]
  • [ 75-57-0 ]
  • [ 6971-51-3 ]
Reference: [1] Tetrahedron, 2008, vol. 64, # 51, p. 11618 - 11624
  • 10
  • [ 5071-96-5 ]
  • [ 620-24-6 ]
  • [ 6971-51-3 ]
Reference: [1] Synlett, 2012, vol. 23, # 5, p. 706 - 710
  • 11
  • [ 620-24-6 ]
  • [ 77-78-1 ]
  • [ 6971-51-3 ]
Reference: [1] Journal of the Chemical Society, 1922, vol. 121, p. 1397
  • 12
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  • [ 1700-31-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 18, p. 2447 - 2450
  • 13
  • [ 620-24-6 ]
  • [ 85684-61-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 4, p. 1230 - 1241
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  • [ 97582-88-2 ]
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 4, p. 1230 - 1241
  • 15
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  • [ 74597-04-9 ]
YieldReaction ConditionsOperation in experiment
86.3% With phosphorus tribromide In dichloromethane at 0 - 20℃; for 1 h; Intermediate 17: 3-(Bromomethyl) phenolTo a 50 mL RB flask fitted with magnetic stirrer was charged 15 mL of dichloromethane. To the stirred solvent was added 3-hydroxymethyl-phenol (0.5 g, 4.03 mmol). The RM was brought to 0 and phosphorous t ribromide (1.6 g, 0.56 mL, 6.04 mmol) was added drop wise. After addition, the RM was stirred at RT for 1 h. After 1 h, the RM was diluted with dichloromethane (25 mL) arid the organic layer was washed with water (20 mL). The organic layer was dried over anhydrous Na2S04 and the solvent was removed under reduced pressure. The product was obtained as brown solid. (0.65 g, yield: 86.3percent); MS (ESI, 120 eV) : m/z =187.0 (M+H)+; 1H NMR (300MHz, CDCI3): δ 7.10-7.15(t, 1 H), 6.86-6.89(d, 1 H), 6.80(d, 1 H), 6.67-6.71 (m, 1 H), 4.35-4.36(d, 2H), 3.80-3.94(bro s, 1 H).
82% With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; for 1.5 h; To a suspension of 3-hydroxybenzylalcohol (1.0 g, 8.06 mmol) and PPh3 (3.17 g, 12.08 mmol) in DCM (40 mL) at 0°C was added CBr4 (4.01 g, 12.08 mmol) dropwise. The reaction was warmed to RT over 90 minutes, concentrated under reduced pressure and purified by silica gel chromatography (5percent to 50percent EtOAc in Hexanes) to give 3-(bromomethyl)phenol as a light brown crystalline solid (1.24 g, 82percent).
82% With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; for 1.5 h; CBr4 (4.01 g, 12.08 mmol) was added dropwise to a suspension of 3-hydroxybenzylalcohol (1.0 g, 8.06 mmol) and PPh3 (3.17 g, 12.08 mmol) in DCM (40 mL) at 0 °C. The reaction mixture was warmed to RT over 90 minutes and then concentratred under reduced pressure. The residue was purified by Si02gel chromatography (5percent to 50percent EtOAc/Hexanes) to yield 3- (bromomethyl)phenol as a light brown crystalline solid (1.24 g, 82percent).
64% With carbon tetrabromide; triphenylphosphine In dichloromethane; acetonitrile at 2 - 20℃; for 2 h; EXAMPLE 3; Synthesis of [lR- [la (Z), 2p (R*), 3a, 5a]]-7- [3, 5-dihydroxy-2- (3-hydroxy-5-phenylpentyl) cyclopentyl]-5-heptenoic acid 3- (nitrooxymethyl) phenyl ester (compound 4); 1. Preparation of 3- [ (Bromo) methyl] phenol; 3-[(Hydroxy) methyl] phenol was dissolved in acetonitrile (300 ml) and dichloromethane (900ml) and the resulting mixture was poured in the flask kept under argon; magnetic stirring was set on. The solution was then cooled with an ice. bath and carbon tetrabromide and triphenilphosphine were added. The latter. was added in small portions in order to maintain the temperature at 2-3 °C. The solution was stirred for 1 hour at 2-3°C and then for an additional hour at room temperature. After this period the reaction (checked by TLC, using EtOAc/Petroleum ether 3/7 as the eluent) was complete. The mixture was evaporated under reduce pressure and 500 ml of petroleum ether and 500 ml of EtOAc were added to the resulting yellow thick oil in a. 21 round flask. A pitchy solid was formed. The mixture was kept under stirring at room temperature overnight and subsequently filtered and concentrated under reduce pressure, furnishing ca. 50 g of an oily residue. The oil was purified by flash chromatography over 600g of silica gel, using EtOAc/Petroleum ether 2/8 as the eluent. Further purification was achieved by crystallising the resulting bromide from petroleum ether. A white solid was obtained (24 g, 64percent). Analysis TLC : (EtOAc/Petroleum ether 3/7) Rf =0.4 HPLC purity: > 98percent FT-IR (KBr, cm1) : 3252,1589, 1479,1392, 1270,1208, 1155,952, 880,791, 741,686.
64% With carbon tetrabromide; triphenylphosphine In dichloromethane; acetonitrile at 0 - 20℃; for 2 h; 3-[(hydroxyl)methyl]phenol (25.0 g, 200 mmol) was dissolved in acetonitrile (300 ml) and dichloromethane (900ml) and the resulting mixture was poured in the flask kept under argon; magnetic stirring was set on. The solution was then cooled with an ice bath and carbon tetrabromide (80.0 g , 240 mmol, 1.2 eq) and triphenylphosphine (77.0 g, 290 mmol, 1.5 eq) were added.The latter was added in small portions in order to maintain the temperature at 2-3°C.The solution was stirred for 1 hour at 2-3°C and then for an additional hour at room temperature. After period the reaction conversion was complete. The obtained mixture was evaporated under reduce pressure and 500 ml of petroleum ether and 500 ml of ethyl acetate were added to the resulting yellow thick oil in a round flask. A pitchy solid was formed. The mixture was kept under stirring at room temperature overnight and subsequently filtered and concentrated under reduce pressure, furnishing ca. 50 g of an oily residue.The oil was purified by flash chromatography over silica gel using ethyl acetate/petroleum ether as eluent. Further purification was achieved by crystallising the resulting bromide from petroleum ether. A white solid was obtained (24 g, 64percent) .TLC (EtOAc/Petroleum ether 3/7) Rf=0.4 HPLC purity>98percentFT-IR (KBr, cm"1) : 3252, 1589, 1479, 1392, 1270, 1208, 1155, 952, 880, 791, 741, 686.
64% With carbon tetrabromide; triphenylphosphine In dichloromethane; acetonitrile at 2 - 20℃; Inert atmosphere Example 4. Preparation of 3-f f nitroxy)methyl1phenol 3-[(Hydroxy)methyl]phenol (25 g, 0.2 mol), is dissolved in acetonitrile (300 ml) and dichloromethane (900 ml) and the resulting mixture is poured into a flask kept under argon with stirring. The solution is cooled with an ice bath and carbon tetrabromide and triphenylphosphine are added. The latter was added in small portions in order to maintain the temperature at ca. 2-3 C. The solution is stirred for 1 hour at 2-3 C followed by an additional hour at room temperature. The reaction conversion is checked by TLC, using EtOAc/Petroleum ether 3/7 as the eluent) until complete. The obtained mixture is evaporated under reduced pressure and 500 ml of petroleum ether and 500 ml of EtOAc is added to the resulting yellow thick oil in a 21 round flask. The mixture is stirred at room temperature overnight and subsequently filtered and concentrated under reduce pressure, furnishing ca. 50 g of an oily residue. The oil is purified by flash chromatography over 600 g of silica gel, using EtOAc/Petroleum ether 2/8 as the eluent. Further purification is achieved by crystallizing the resulting bromide from petroleum ether. A white solid is obtained (24 g, 64percent). HPLC purity: >98percent; FT-IR (KBr, cm-1): 3252, 1589, 1479, 1392, 1270, 1208, 1155, 952, 880, 791, 741, 686. 3-[(Bromo)methyl]phenol is dissolved in 30 ml of acetonitrile and poured in the flask, kept far from light sources and stirred at 0-5 C under argon. Silver nitrate is added under these conditions, maintaining the temperature under 5 C. The reaction course is followed by TLC (EtOAc/Petroleum ether 3/7 as the eluent). After 4 hours and 30 minutes the conversion is complete. The reaction mixture is filtered, the precipitated solid is washed with ether and the filtrate iss separated in two batches. The first batch (15 ml) is kept under argon and in acetonitrile solution at -20 C. The second batch (15 ml) is worked-up as follows. The acetonitrile solution is concentrated under reduce pressure and the resulting oil is dissolved in dichloromethane (15 ml) and washed with brine (15 ml). The organic phase is separated and the aqueous phase is extracted twice with dichloromethane (2x 25 ml). The combined organic phases are dried over MgS04, filtered and evaporated. The residue is purified by flash chromatography over 40 g of silica gel using EtOAc/Petroleum ether 2/8 as the eluent The nitrate is obtained as an oil (0.6 g, 67percent). HPLC purity: >98percent; MS (ESI-): 168 (M+-1); FT-IR (neat oil, cm-'): 3365, 1632, 1599, 1459, 1282, 1160, 923, 867, 793, 757.
59% With phosphorus tribromide In dichloromethane at -15 - 20℃; for 3 h; Example 40 Synthesis of 3-hydroxybenzyl bromideA reactor was charged with 3-hydroxybenzyl alcohol (500 mg), and dichloromethane (5 ml) and the mixture cooled to -15 °C. Phosphorous tribromide (568 μΚ) was added dropwise and the reaction was allowed to warm to room temperature over 3 hours. The reaction was quenched by the dropwise addition of water (10 ml) and the organics were separated. The aqueous was washed with dichloromethane (2x10 ml) and the combined organics were washed with saturated aqueous sodium bicarbonate solution (10 ml), then water (10 ml). The organics were dried (Na2S04), filtered and reduced to yield an oil, which was purified on a Reveleris® X2 Flash Chromatography System, eluting with n-hexane and ethyl acetate. Appropriate fractions were collected for the product peak and were reduced by rotary evaporation to obtain the desired product as a white solid (446 mg, 59percent). The structure was confirmed as 3-hydroxybenzyl bromide by 1H NMR.
2.8 g With phosphorus tribromide In dichloromethane at 0℃; for 0.5 h; Inert atmosphere To a solution of 3-(hydroxymethyl)phenol (2.5 g, 20.1 mmol) in dry DCM (50 mL) was added PBr3 (6.5 g, 24.1 mmol) at 0° C. under nitrogen. The mixture was stirred for 30 minutes, then washed with saturated aqueous NaHCO3 (10 mL). The organic layer was washed with saturated aqueous NaCl (2×10 mL), dried over anhydrous Na2SO4, and concentrated in vacuo to yield Compound 1 (2.8 g) as a yellow solid. 1H NMR: (CDCl3) 4.431 (s, 2H), 6.747-6.786 (m, 1H), 6.869 (t, J=2.1 Hz, 1H), 6.957 (d, J=7.8 Hz, 1H), 7.231 (t, J=7.8 Hz, 1H).

Reference: [1] Chemische Berichte, 1989, vol. 122, p. 347 - 356
[2] Patent: WO2012/11125, 2012, A1, . Location in patent: Page/Page column 70; 71-72
[3] Patent: WO2014/31936, 2014, A2, . Location in patent: Paragraph 0327; 0328
[4] Patent: WO2014/31928, 2014, A2, . Location in patent: Paragraph 0334
[5] Patent: WO2005/68421, 2005, A1, . Location in patent: Page/Page column 39-40
[6] Patent: WO2006/15930, 2006, A1, . Location in patent: Page/Page column 7
[7] Patent: WO2013/133980, 2013, A1, . Location in patent: Page/Page column 17; 18
[8] Patent: WO2016/114668, 2016, A1, . Location in patent: Page/Page column 47; 48
[9] Angewandte Chemie - International Edition, 2011, vol. 50, # 30, p. 6924 - 6927
[10] Dalton Transactions, 2015, vol. 44, # 7, p. 3251 - 3258
[11] Patent: WO2013/78237, 2013, A1, . Location in patent: Page/Page column 109; 110
[12] Journal of Medicinal Chemistry, 1980, vol. 23, # 9, p. 1013 - 1022
[13] Journal of Organometallic Chemistry, 2003, vol. 687, # 1, p. 185 - 189
[14] Patent: WO2004/41803, 2004, A1, . Location in patent: Page 41-42
[15] Patent: US2013/323271, 2013, A1, . Location in patent: Paragraph 0384; 0385
[16] ACS Catalysis, 2013, vol. 3, # 11, p. 2505 - 2514
[17] Chemistry - A European Journal, 2014, vol. 20, # 21, p. 6421 - 6432
[18] Patent: WO2006/117368, 2006, A1, . Location in patent: Page/Page column 40
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Reference: [1] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 2, p. 91 - 96
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