[ CAS No. 620-17-7 ] {[proInfo.proName]}

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Quality Control of [ 620-17-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 620-17-7 ]

Product Details of [ 620-17-7 ]

CAS No. :	620-17-7	MDL No. :	MFCD00002311
Formula :	C₈H₁₀O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HMNKTRSOROOSPP-UHFFFAOYSA-N
M.W :	122.16	Pubchem ID :	12101
Synonyms :

Safety of [ 620-17-7 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P273-P280-P305+P351+P338-P310	UN#:	3145
Hazard Statements:	H302+H312+H332-H314-H402	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 620-17-7 ]

* 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.

Upstream synthesis route of [ 620-17-7 ]
Downstream synthetic route of [ 620-17-7 ]

[ 620-17-7 ] Synthesis Path-Upstream 1~5

1
[ 620-17-7 ]
[ 121-71-1 ]
[ 620-18-8 ]
[ 131341-58-7 ]

Yield	Reaction Conditions	Operation in experiment
18 %Chromat.	Stage #1: With ferredoxin reductase; ferredoxin; 4-methylphenyl phosphate synthase; P₄₅₀ monooxygenase; nicotinamide adenine dinucleotide phosphate; nicotinamide adenine dinucleotide; ATP; magnesium chloride; manganese(ll) chloride; alcohol dehydrogenase; aldehyde dehydrogenase In aq. buffer at 30℃; for 2 h; Enzymatic reaction Stage #2: With phosphohydrolase In aq. buffer at 30℃; for 2 h; Enzymatic reaction	General procedure: Unless specified otherwise, all enzymatic assays were carriedout in 100 μL of 50 mM Tris·HCl buffer (pH 8.0) at 30 °C for 2 h, and thefinal concentration of each enzyme was 10 μM. Methanol (3× volume) wasadded to quench reactions. Precipitated proteins were removed by centrifugationat 20,000 × g for 10 min and the supernatants were used as LC-MSsamples. For reactions catalyzed by CreHI, the reaction mixture contained1 mM substrate, 20 mM MgCl2, 2 mM MnCl2, 2 mM ATP, and purified CreHand CreI. For CreJEF activity toward phosphorylated compounds (2′–9′), theCreHI reactions were used to generate the phosphorylated substrates. Next,CreJ, CreE, and CreF together with 3 mM NADPH were added into the individualpost-CreHI reaction mixture.For one-pot chemomimetic alkylphenol oxidation reactions, the reactionmixtures contained CreHI, CreJEF, and the two optional enzymes CreG (with2 mM NAD+) and CreC (with 2 mM NADP+), 1 mM substrate 2–7, and necessarycofactors, including 20 mM MgCl2, 2 mM MnCl2, 2 mM ATP, and 3 mMNADPH. After incubation at 30 °C for 2 h, CreD was added into each of theone-pot mixtures, followed by another 2-h incubation at 30 °C.

Reference： [1] Proceedings of the National Academy of Sciences of the United States of America, 2017, vol. 114, # 26, p. E5129 - E5137

2
[ 620-17-7 ]
[ 4885-02-3 ]
[ 161876-64-8 ]
[ 532967-00-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	With titanium tetrachloride In dichloromethane at 0℃; for 0.75 h;	Titanium(IV) chloride (100 ml, 100 mmol, 1M in CH₂CI₂) followed by dichloromethyl methyl ether (7.47 ml, 82.5 mmol) was added to a cooled 0 °C solution of 3-ethylphenol (6.1 1g, 50 mmol). The reaction mixture was stirred for 45 mins. The mixture was poured into ice and extracted with EtOAc. The organic layers were washed with brine, dried over Na₂SO₄-inl-concentrated to a bright pink oil. Purification by flash column chromatography (0percent to 10percent EtOAc in hexanes) gave 4-ethyl-2-hydroxy-benzaldehyde (4.9g, 65percent) followed by 2-ethyl-4-hydroxy-benzaldehyde (1.32 g, 18percent). A: ¹H NMR (400 MHz, CDCI₃): 5 1.25 (t, J=7.6 Hz, 3 H), 2.67 (d, J=7.6 Hz, 2 H), 6.82 (s, 1 H), 6.85 (d, J=8.0 Hz, 1 H), 7.46 (t, J=8.0 Hz, 1 H), 9.83 (s, 1 H), 11.05 (s, 1 H). B: ¹H NMR (400 MHz, CDCI₃): 6 1.27 (t, J=7.6 Hz, 3 H), 3.03 (d, J=7.6 Hz, 2 H), 6.68 (s, 1 H), 6.78 (s, 1 H), 6.82 (d, J=8.3 Hz, 1 H), 7.77 (t, J=8.3 Hz, 1 H), 10.10 (s, 1 H).

Reference： [1] Patent: WO2006/18725, 2006, A1, . Location in patent: Page/Page column 120-121

3
[ 50-00-0 ]
[ 620-17-7 ]
[ 161876-64-8 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 14, p. 4917 - 4927
[2] Journal of Chemical Research, 2006, # 6, p. 402 - 405
[3] Organic and Biomolecular Chemistry, 2017, vol. 15, # 6, p. 1530 - 1536
[4] Chemical Research in Toxicology, 2010, vol. 23, # 1, p. 240 - 250

4
[ 620-17-7 ]
[ 161876-64-8 ]

Reference： [1] Chemische Berichte, 1949, vol. 82, p. 405

5
[ 620-17-7 ]
[ 99873-30-0 ]

Yield	Reaction Conditions	Operation in experiment
7.25 g	With N-Bromosuccinimide In chloroform at 0 - 20℃; for 2 h;	At 0°C cooling in ice, a mixture of 7.33g of 3-ethylphenol and 600mL of chloroform was added 10.7g of N-bromosuccinimide. After the temperature was raised to room temperature and stirred for 2 hours, The reaction solution was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 7.25g of 4-bromo-3-ethylphenol (Referred to as 45A).
7.25 g	With N-Bromosuccinimide In chloroform at 0 - 20℃; for 2 h; Cooling with ice	Reference Production Example 45 (0707) While stirring a mixture of 7.33 g of 3-ethylphenol and 600 mL of chloroform under ice cooling at 0° C., 10.7 g of N-bromosuccinimide was added. After raising the temperature to room temperature and stirring for 2 hours, the reaction solution was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 7.25 g of 4-bromo-3-ethylphenol (referred to as 45A). (0708) ¹H-NMR (CDCl₃) δ: 7.37 (1H, d, J=8.2 Hz), 6.90 (1H, d, J=2.1 Hz), 6.69 (1H, dd, J=8.2, 2.1 Hz), 5.48 (1H, s), 2.61 (2H, q, J=7.6 Hz), 1.24 (3H, t, J=7.6 Hz).

Reference： [1] Patent: WO2011/34828, 2011, A1, . Location in patent: Page/Page column 84
[2] Patent: EP2177513, 2010, A1, . Location in patent: Page/Page column 28
[3] Patent: CN105392779, 2016, A, . Location in patent: Paragraph 1351; 1352; 1353; 1354
[4] Patent: US2016/159755, 2016, A1, . Location in patent: Paragraph 0707; 0708

[ 620-17-7 ] Synthesis Path-Downstream 1~30

1
[ 622-98-0 ]
[ 620-17-7 ]

Reference： [1]Patent: US2129907,1937,

2
[ 620-17-7 ]
[ 161876-64-8 ]

Reference： [1]Chemische Berichte,1949,vol. 82,p. 405

3
[ 620-17-7 ]
[ 79-11-8 ]
[ 1878-51-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide
	With sodium hydroxide

Reference： [1]Brueckner [Angewandte Chemie, 1928, vol. 41, p. 1046][Fresenius' Zeitschrift fuer Analytische Chemie, 1928, vol. 75, p. 290]
[2]Steinkopf; Hoepner [Journal fur praktische Chemie (Leipzig 1954), 1926, vol. <2> 113, p. 156]

4
[ 2832-19-1 ]
[ 620-17-7 ]
[ 75552-12-4 ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 1414 - 1427

5
[ 620-17-7 ]
[ 71486-53-8 ]
[ 86371-00-8 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 9 8-Ethyl-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-c]pyridin-5-one Prepared by the method described for Example 1 from 3-ethylphenol (12.2 g, 0.1 moles) and <strong>[71486-53-8]methyl 4-oxo-3-piperidinecarboxylate hydrochloride</strong> (19.3 g, 0.1 moles). The crude material is washed with water and dried to give the product (6.6 g), mp 80°-85° C.

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 683 - 688
[2]Patent: US4382939,1983,A

6
[ 1878-51-9 ]
[ 620-17-7 ]
[ 124-38-9 ]
[ 201230-82-2 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridinium hydrobromide perbromide; acetic acid at 19.9℃; ΔH(activ.), ΔS(activ.); var. temperature;

Reference： [1]Karunakaran; Elango [Journal of Physical Organic Chemistry, 1996, vol. 9, # 2, p. 105 - 110]

7
[ 64-17-5 ]
[ 108-95-2 ]
[ 90-00-6 ]
[ 123-07-9 ]
[ 620-17-7 ]
[ 60-12-8 ]
[ 1006-59-3 ]

Reference： [1]Russian Journal of Applied Chemistry,1998,vol. 71,p. 651 - 653

8
[ 7647-01-0 ]
[ 7446-70-0 ]
[ 620-17-7 ]
[ 71-43-2 ]
zinc cyanide [ No CAS ]
[ 161876-64-8 ]
[ 532967-00-3 ]

Reference： [1]Journal of the American Chemical Society,1943,vol. 65,p. 1572,1576

9
[ 620-17-7 ]
zinc cyanide [ No CAS ]
[ 161876-64-8 ]
[ 532967-00-3 ]

Reference： [1]Journal of the American Chemical Society,1943,vol. 65,p. 1572,1576
[2]Journal of the American Chemical Society,1943,vol. 65,p. 1572,1576

10
[ 1878-51-9 ]
[ 620-17-7 ]

Yield	Reaction Conditions	Operation in experiment
	at 275℃;

Reference： [1]Kruber; Schmitt [Chemische Berichte, 1931, vol. 64, p. 2270,2276]

11
[ 50-00-0 ]
[ 620-17-7 ]
[ 161876-64-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 4917 - 4927
[2]Journal of Chemical Research,2006,p. 402 - 405
[3]Organic and Biomolecular Chemistry,2017,vol. 15,p. 1530 - 1536
[4]Chemical Research in Toxicology,2010,vol. 23,p. 240 - 250

12
[ 620-17-7 ]
[ 4885-02-3 ]
[ 161876-64-8 ]
[ 532967-00-3 ]

Yield	Reaction Conditions	Operation in experiment
65%; 18%	With titanium tetrachloride; In dichloromethane; at 0℃; for 0.75h;	Titanium(IV) chloride (100 ml, 100 mmol, 1M in CH2CI2) followed by dichloromethyl methyl ether (7.47 ml, 82.5 mmol) was added to a cooled 0 C solution of 3-ethylphenol (6.1 1g, 50 mmol). The reaction mixture was stirred for 45 mins. The mixture was poured into ice and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4-inl-concentrated to a bright pink oil. Purification by flash column chromatography (0% to 10% EtOAc in hexanes) gave 4-ethyl-2-hydroxy-benzaldehyde (4.9g, 65%) followed by 2-ethyl-4-hydroxy-benzaldehyde (1.32 g, 18%). A: 1H NMR (400 MHz, CDCI3): 5 1.25 (t, J=7.6 Hz, 3 H), 2.67 (d, J=7.6 Hz, 2 H), 6.82 (s, 1 H), 6.85 (d, J=8.0 Hz, 1 H), 7.46 (t, J=8.0 Hz, 1 H), 9.83 (s, 1 H), 11.05 (s, 1 H). B: 1H NMR (400 MHz, CDCI3): 6 1.27 (t, J=7.6 Hz, 3 H), 3.03 (d, J=7.6 Hz, 2 H), 6.68 (s, 1 H), 6.78 (s, 1 H), 6.82 (d, J=8.3 Hz, 1 H), 7.77 (t, J=8.3 Hz, 1 H), 10.10 (s, 1 H).

Reference： [1]Patent: WO2006/18725,2006,A1 .Location in patent: Page/Page column 120-121

13
[ 6636-55-1 ]
[ 620-17-7 ]
C₁₅H₁₅NO₃ [ No CAS ]

Reference： [1]Patent: EP1207154,2002,A1 .Location in patent: Example 4

14
[ 620-17-7 ]
[ 99873-30-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	With N-Bromosuccinimide; trifluorormethanesulfonic acid; In acetonitrile; at -30 - 20℃; for 12.0h;Inert atmosphere;	To a solution of 3-ethylphenol (22, 1.22 g, 10 mmol) in acetonitrile (CH3CN, 15mL) at 30 C were added sequentially with trifluoromethanesulfonic acid (TfOH,N-bromosuccinimide (NBS, 1.79 g, 10 mmol). The resultingreaction mixture was allowed to warm up to room temperature, and then stirred atroom temperature for 12 hours. The mixture was added sequentially with water (10mL) and diethyl ether (10 mL). The aqueous phase was extracted with diethyl ether (3x 20 mL). The combined organic phases were washed sequentially with saturatedaqueous sodium sulfite solution (Na2SO3, 20 mL) and brine (20 mL), dried overanhydrous sodium sulfate (Na2SO4), filtered, and concentrated under reduced pressure.The residue was purified by column chromatography (20% ethyl acetate in petroleumether) silica gel to afford 4-bromo-3-ethylphenol (23) as a white solid (1.89 g).Yield: 94%; m.p. = 51 53 C; 1H NMR (400 MHz, CDCl3): = 7.36 (d, J = 8.6Hz, 1H), 6.74 (d, J = 2.9 Hz, 1H), 6.56 (dd, J = 8.6, 3.0 Hz, 1H), 5.28 (s, 1H), 2.69 (q,J = 7.6 Hz, 2H), 1.20 (t, J = 7.5 Hz, 3H); 13C NMR (100 MHz, CDCl3): =154.7, 144.6, 133.3, 116.4, 114.8, 114.5, 29.3, 13.9; max = 3342, 2969,2932, 2873, 1577, 1468, 1439, 1285, 1236, 1161, 1058, 1027, 863, 807 cm-1. HRMS(ESI): m/z calcd for C8H9BrNaO [M+Na]+: 222.9729; found: 222.9737.
36%	With bromine; acetic acid;	Step 1 : 4-Bromo-3-ethylphenolTo a solution of 3-ethylphenol (3.0 g, 24.6 mmol) in acetic acid (20 ml) was added bromine (4 g, 22 mmol) in acetic acid (10 ml) dropwise over 5 minutes. The mixture was stirred at room temperature for 18 hours. The mixture was poured into water (100 ml) and was extracted with ethyl acetate (100 ml). The organic layer was washed with aqueous sodium bicarbonate and then water, dried over magnesium sulfate and filtered. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel using 100% heptane and then 9: 1 heptane: ethyl acetate to give the title compound as an oil (1.6 g, 36%).
	With tetra-N-butylammonium tribromide; In methanol; dichloromethane; at 20℃; for 1.0h;Inert atmosphere;	Example 13 4-bromo-3-ethylphenol Under argon atmosphere, to the mixture of 3-ethylphenol(11.2g), methylene chloride(30mL), and methanol(20mL), tetra-n-butylammonium tribromide (24.9g) was added and stirred for 1 hour at room temperature. The reaction mixture was diluted with ethyl acetate and the organic layer was washed with a 1N hydrochloric acid, water and saturated brine solution and was dried by anhydrous magnesium sulphate. The title compound (11.2 g) having the following physical data was obtained by removing the solvent. TLC:Rf 0.49(n-hexane:ethyl acetate:acetic acid=1:4); 1H-NMR: (CDCl3) delta 1.22, 2.69, 4.92, 6.57, 6.74, 7.37.

7.25 g	With N-Bromosuccinimide; In chloroform; at 0 - 20℃; for 2.0h;	At 0C cooling in ice, a mixture of 7.33g of 3-ethylphenol and 600mL of chloroform was added 10.7g of N-bromosuccinimide. After the temperature was raised to room temperature and stirred for 2 hours, The reaction solution was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 7.25g of 4-bromo-3-ethylphenol (Referred to as 45A).
7.25 g	With N-Bromosuccinimide; In chloroform; at 0 - 20℃; for 2.0h;Cooling with ice;	Reference Production Example 45 (0707) While stirring a mixture of 7.33 g of 3-ethylphenol and 600 mL of chloroform under ice cooling at 0 C., 10.7 g of N-bromosuccinimide was added. After raising the temperature to room temperature and stirring for 2 hours, the reaction solution was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 7.25 g of 4-bromo-3-ethylphenol (referred to as 45A). (0708) 1H-NMR (CDCl3) delta: 7.37 (1H, d, J=8.2 Hz), 6.90 (1H, d, J=2.1 Hz), 6.69 (1H, dd, J=8.2, 2.1 Hz), 5.48 (1H, s), 2.61 (2H, q, J=7.6 Hz), 1.24 (3H, t, J=7.6 Hz).

Reference： [1]Natural Product Research,2019,vol. 33,p. 2911 - 2916
[2]Patent: WO2011/34828,2011,A1 .Location in patent: Page/Page column 84
[3]Patent: EP2177513,2010,A1 .Location in patent: Page/Page column 28
[4]Patent: CN105392779,2016,A .Location in patent: Paragraph 1351; 1352; 1353; 1354
[5]Patent: US2016/159755,2016,A1 .Location in patent: Paragraph 0707; 0708

15
[ 620-17-7 ]
[ 55876-84-1 ]
[ 1417421-44-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate; In acetonitrile; at 85℃; for 2h;	Example 9. Synthesis of 1-548-102. Into a 50-mL round-bottom flask, was placed a solution of <strong>[55876-84-1]methyl 5-(bromomethyl)picolinate</strong> (500 mg, 2.09 mmol, 1.00 equiv, 96percent) in acetonitrile (20 mL), 3-ethylphenol (280 mg, 2.29 mmol, 1.05 equiv), and potassium carbonate (900 mg, 6.51 mmol, 3.00 equiv). The resulting solution was stirred for 2 h at 85°C. The mixture was concentrated under vacuum. The residue was diluted with 30 mL of water and extracted with 2x20 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 0.6 g (92percent) of methyl 5-((3- ethylphenoxy)methyl)picolinate as a brown solid.LC-MS: (ES, m/z): 272 [M+H]+

Reference： [1]Patent: WO2013/3505,2013,A1 .Location in patent: Page/Page column 58; 59

16
[ 10401-11-3 ]
[ 620-17-7 ]
[ 620-18-8 ]

Yield	Reaction Conditions	Operation in experiment
	With carbon monoxide; hydrogen; In tetrahydrofuran; at 70℃; under 7757.43 Torr; for 6h;Autoclave;	General procedure: To a 100 mL high-pressure reactor, phenylacetylene (1 mmol),Pd (0.96 mol%) in a 10 mL THF were transferred under an inertatmosphere. The reactor was flushed three times with nitrogen then pressurized with desired 150 psi of syngas, then heated at70C with constant stirring (400 rpm) for 6 h. After the comple-tion of reaction, the reactor cooled down to room temperature andthe remaining syngas was carefully depressurized. The resultantreaction mixture filtered off by simple filtration. The filtrate was then collected in sample vial and the product was extracted for fur-ther analysis such as GC, GC-MS,1H &13C NMR and matched with those of authentic data. Selective experiments were performed in triplicate and it was observed that results showed variation of ±2%.

Reference： [1]Chemical Communications,2013,vol. 49,p. 3416 - 3418
[2]Journal of Molecular Catalysis A: Chemical,2016,vol. 414,p. 78 - 86

17
lignin, softwood Kraft black liquor [ No CAS ]
[ 95-87-4 ]
[ 6380-23-0 ]
[ 106-44-5 ]
[ 620-17-7 ]
[ 93-51-6 ]
[ 2785-87-7 ]
[ 4463-33-6 ]
[ 3209-13-0 ]
[ 2896-67-5 ]
[ 7786-61-0 ]
[ 2785-89-9 ]
[ 24599-58-4 ]
[ 5932-68-3 ]
[ 2503-46-0 ]
[ 14059-92-8 ]
[ 121-33-5 ]
[ 95-48-7 ]
[ 90-05-1 ]
[ 498-02-2 ]
[ 108-95-2 ]

Reference： [1]Green Chemistry,2013,vol. 15,p. 2904 - 2912

18
[ 620-17-7 ]
[ 182499-90-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: nitric acid / water / 0.5 h / 20 °C 2: hydrogen iodide; hypophosphorous acid / 1 h / Reflux

Reference： [1]Wakamatsu, Kazumasa; Tanaka, Hitomi; Tabuchi, Keisuke; Ojika, Makoto; Zucca, Fabio A.; Zecca, Luigi; Ito, Shosuke [Molecules, 2014, vol. 19, # 6, p. 8039 - 8050]

19
[ 620-18-8 ]
[ 620-17-7 ]

Yield	Reaction Conditions	Operation in experiment
101 mg	With di-μ-bromobis(tri-tert-butylphosphino)dipalladium(I); [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro[[2-(1-methyl-2-oxopropoxy)phenyl]methylene]ruthenium(II); hydrogen; pyrographite In tetrahydrofuran; methanol at 50℃; for 3h;

Reference： [1]Baader; Podsiadly; Cole-Hamilton; Goossen [Green Chemistry, 2014, vol. 16, # 12, p. 4885 - 4890]

20
[ 620-17-7 ]
[ 121-71-1 ]
[ 620-18-8 ]
[ 131341-58-7 ]
(S)‐(−)‐3‐(1‐hydroxyethyl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 18 %Chromat. 2: 12 %Chromat. 3: 10 %Chromat. 4: 5.3 %Chromat.	Stage #1: 3-ethylphenol With ferredoxin reductase; ferredoxin; 4-methylphenyl phosphate synthase; P₄₅₀ monooxygenase; nicotinamide adenine dinucleotide phosphate; nicotinamide adenine dinucleotide; ATP; magnesium chloride; manganese(ll) chloride; alcohol dehydrogenase; aldehyde dehydrogenase In aq. buffer at 30℃; for 2h; Enzymatic reaction; Stage #2: With phosphohydrolase In aq. buffer at 30℃; for 2h; Enzymatic reaction;	Enzymatic Assays General procedure: Unless specified otherwise, all enzymatic assays were carriedout in 100 μL of 50 mM Tris·HCl buffer (pH 8.0) at 30 °C for 2 h, and thefinal concentration of each enzyme was 10 μM. Methanol (3× volume) wasadded to quench reactions. Precipitated proteins were removed by centrifugationat 20,000 × g for 10 min and the supernatants were used as LC-MSsamples. For reactions catalyzed by CreHI, the reaction mixture contained1 mM substrate, 20 mM MgCl2, 2 mM MnCl2, 2 mM ATP, and purified CreHand CreI. For CreJEF activity toward phosphorylated compounds (2′-9′), theCreHI reactions were used to generate the phosphorylated substrates. Next,CreJ, CreE, and CreF together with 3 mM NADPH were added into the individualpost-CreHI reaction mixture.For one-pot chemomimetic alkylphenol oxidation reactions, the reactionmixtures contained CreHI, CreJEF, and the two optional enzymes CreG (with2 mM NAD+) and CreC (with 2 mM NADP+), 1 mM substrate 2-7, and necessarycofactors, including 20 mM MgCl2, 2 mM MnCl2, 2 mM ATP, and 3 mMNADPH. After incubation at 30 °C for 2 h, CreD was added into each of theone-pot mixtures, followed by another 2-h incubation at 30 °C.

Reference： [1]Du, Lei; Dong, Sheng; Zhang, Xingwang; Jiang, Chengying; Chen, Jingfei; Yao, Lishan; Wang, Xiao; Wan, Xiaobo; Liu, Xi; Wangi, Xinquan; Huang, Shaohua; Cui, Qiu; Feng, Yingang; Liu, Shuang-Jiang; Li, Shengying [Proceedings of the National Academy of Sciences of the United States of America, 2017, vol. 114, # 26, p. E5129 - E5137]

21
[ 620-17-7 ]
[ 620-18-8 ]
(S)‐(−)‐3‐(1‐hydroxyethyl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 28.4 %Chromat. 2: 11 %Chromat.	Stage #1: 3-ethylphenol With 4-methylphenyl phosphate synthase; ATP; magnesium chloride; manganese(ll) chloride In aq. buffer at 30℃; for 2h; Enzymatic reaction; Stage #2: With ferredoxin reductase; ferredoxin; P₄₅₀ monooxygenase; NADPH In aq. buffer at 30℃; for 2h; Enzymatic reaction; Stage #3: With phosphohydrolase In aq. buffer at 30℃; for 2h; Enzymatic reaction;	Enzymatic Assays General procedure: Unless specified otherwise, all enzymatic assays were carriedout in 100 μL of 50 mM Tris·HCl buffer (pH 8.0) at 30 °C for 2 h, and thefinal concentration of each enzyme was 10 μM. Methanol (3× volume) wasadded to quench reactions. Precipitated proteins were removed by centrifugationat 20,000 × g for 10 min and the supernatants were used as LC-MSsamples. For reactions catalyzed by CreHI, the reaction mixture contained1 mM substrate, 20 mM MgCl2, 2 mM MnCl2, 2 mM ATP, and purified CreHand CreI. For CreJEF activity toward phosphorylated compounds (2′-9′), theCreHI reactions were used to generate the phosphorylated substrates. Next,CreJ, CreE, and CreF together with 3 mM NADPH were added into the individualpost-CreHI reaction mixture.For one-pot chemomimetic alkylphenol oxidation reactions, the reactionmixtures contained CreHI, CreJEF, and the two optional enzymes CreG (with2 mM NAD+) and CreC (with 2 mM NADP+), 1 mM substrate 2-7, and necessarycofactors, including 20 mM MgCl2, 2 mM MnCl2, 2 mM ATP, and 3 mMNADPH. After incubation at 30 °C for 2 h, CreD was added into each of theone-pot mixtures, followed by another 2-h incubation at 30 °C.

22
[ 18173-64-3 ]
[ 620-17-7 ]
[ 1204242-96-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	With 1H-imidazole In N,N-dimethyl-formamide	I.23 (3-(l-bromoethyl)phenoxy)(tert-butyl)dimethylsilane 3-ethylphenol (1 g, 8.19 mmol), TBS-C1 (1.357 g, 9.00 mmol), and Imidazole (1.226 g, 18.01 mmol) were stirred overnight in lOmL DMF. Diluted with 25mL water and extracted with 25mL Ethyl acetate. The organic portion was dried over sodium sulfate and the solvent was removed. The crude oil was filtered through a pad of silica using -5% EtOAc in Hexanes yielding tert- butyl(3-ethylphenoxy)dimethylsilane compound as a colorless oil (1.8 g, 7.61 mmol, 93 % yield).

Reference： [1]Current Patent Assignee: UNIVERSITY OF MICHIGAN; INDIANA UNIVERSITY - WO2017/223086, 2017, A1 Location in patent: Page/Page column 99-100

23
[ 620-17-7 ]
[ 63485-50-7 ]
(trans)-methyl 3-(3-ethylphenoxy)cyclobutanecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 72h;	Triphenylphosphine (504 mg, 1 .92 mmol) was added to a solution of 3-ethylphenol (0.20 ml_, 1 .6 mmol) in tetrahydrofuran (5 ml_). The reaction mixture was cooled to 0 C, and (c/s)-methyl 3-hydroxycyclobutanecarboxylate (250 mg, 1 .92 mmol) was added, followed by DIAD (0.37 ml_, 1 .9 mmol). After 10 min, the reaction mixture was warmed to room temperature, stirred for 3 days and diluted with water and EtOAc. The mixture was partitioned, and the aqueous layer was extracted with EtOAc (2X). The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated. The residue was purified on silica gel eluting with a 0%-100% EtOAc-hexanes gradient to give the title compound (169 mg, 41 %). 1H NMR (400 MHz, CD3SOCD3) delta 1 .13 (t, J = 8 Hz, 3 H), 2.22-2.31 (m, 2 H), 2.45-2.56 (m, 2 H), 2.58- 2.65 (m, 2 H), 3.10-3.19 (m, 1 H), 3.62 (s, 3 H), 4.72-4.81 (m, 1 H), 6.56-6.61 (m, 2 H), 6.75 (d, J = 8 Hz, 1 H), 7.1 1 -7.16 (m, 1 H); LC-MS (LC-ES) M+H = 235.

Reference： [1]Patent: WO2018/69863,2018,A1 .Location in patent: Page/Page column 233

24
[ 620-17-7 ]
[ 63485-50-7 ]
(trans)-3-(3-ethylphenoxy)cyclobutanecarboxylic acid [ No CAS ]

Reference： [1]Patent: WO2018/69863,2018,A1

25
[ 150-76-5 ]
ethylphenol [ No CAS ]
propylphenol [ No CAS ]
butylphenol [ No CAS ]
pentylphenol [ No CAS ]
[ 123-07-9 ]
[ 128-39-2 ]
[ 620-17-7 ]
[ 2934-05-6 ]
[ 2078-54-8 ]
[ 26886-05-5 ]
[ 2934-07-8 ]
[ 4130-42-1 ]
[ 96-76-4 ]
[ 1197-34-8 ]
[ 936-89-0 ]
[ 120-95-6 ]
[ 876-20-0 ]
[ 54932-77-3 ]

Yield	Reaction Conditions	Operation in experiment
	With molybdenum(VI) oxide; In ethanol; at 280℃; for 4h;Inert atmosphere;	General procedure: 2.0 g of guaiac acid (purchased in Tianjin Guangfu Technology Co., Ltd.), 0.5 g of MOS catalyst and 100 ml of ethanol were placed in a 300 ml reaction vessel, and the air in the reaction vessel was replaced with nitrogen. The temperature was raised to 280 C, and the reaction was stirred for 4 h. After the reaction was completed, the mixture was filtered under suction and rotary evaporated. The liquid product was subjected to qualitative analysis on a gas chromatography-mass spectrometer (GC6890-MS5973, Agilent), and the internal standard was added. Quantitative analysis by gas chromatography. The chromatogram was performed on an HP-5ms, 30m X 0.25mm X 0.25mum capillary column. The conversion of the raw guaiacol is calculated by (initial guaiacol moles - residual guaiacol moles) / (initial guaiacol moles) X100%, and the selectivity of the product hydrocarbyl phenol is (hydrocarbyl phenol) The number of moles / (molar guaiacol moles) X 100 % was calculated. Among the guaiacol conversion products, ethyl phenols include o-ethyl phenol, 2,5-diethyl phenol, 3,5-diethyl phenol, and propyl phenols include 2,6-diisopropyl phenol. , 2,4-diisopropylphenol, 2,4,6-triisopropylphenol, butyl phenols including 2,5-di-sec-butylphenol, 2,6-di-tert-butylphenol, 2, 4-di-tert-butylphenol, 2,6-di-tert-butyl-p-ethylphenol, pentanols include 2,4-di-tert-amylphenol, others include o-ethoxyphenol, o-ethoxybenzene Methyl ether, p-ethyl guaiacol, 2,6-diisopropylanisole).

Reference： [1]Patent: CN107586255,2018,A .Location in patent: Paragraph 0042-0043; 0070

26
[ 94-71-3 ]
ethylphenol [ No CAS ]
propylphenol [ No CAS ]
butylphenol [ No CAS ]
pentylphenol [ No CAS ]
methylphenol [ No CAS ]
mono-tert-butyl-m-cresol [ No CAS ]
[ 123-07-9 ]
[ 128-39-2 ]
[ 620-17-7 ]
[ 2934-05-6 ]
[ 527-18-4 ]
[ 2078-54-8 ]
[ 4130-42-1 ]
[ 1138-52-9 ]
[ 1197-34-8 ]
[ 5875-45-6 ]
[ 35946-91-9 ]
[ 876-20-0 ]

Yield	Reaction Conditions	Operation in experiment
	With molybdenum(VI) oxide; In ethanol; at 280℃; for 4h;Inert atmosphere;	General procedure: 2.0 g of guaiac acid (purchased in Tianjin Guangfu Technology Co., Ltd.), 0.5 g of MOS catalyst and 100 ml of ethanol were placed in a 300 ml reaction vessel, and the air in the reaction vessel was replaced with nitrogen. The temperature was raised to 280 C, and the reaction was stirred for 4 h. After the reaction was completed, the mixture was filtered under suction and rotary evaporated. The liquid product was subjected to qualitative analysis on a gas chromatography-mass spectrometer (GC6890-MS5973, Agilent), and the internal standard was added. Quantitative analysis by gas chromatography. The chromatogram was performed on an HP-5ms, 30m X 0.25mm X 0.25mum capillary column. The conversion of the raw guaiacol is calculated by (initial guaiacol moles - residual guaiacol moles) / (initial guaiacol moles) X100%, and the selectivity of the product hydrocarbyl phenol is (hydrocarbyl phenol) The number of moles / (molar guaiacol moles) X 100 % was calculated. Among the guaiacol conversion products, ethyl phenols include o-ethyl phenol, 2,5-diethyl phenol, 3,5-diethyl phenol, and propyl phenols include 2,6-diisopropyl phenol. , 2,4-diisopropylphenol, 2,4,6-triisopropylphenol, butyl phenols including 2,5-di-sec-butylphenol, 2,6-di-tert-butylphenol, 2, 4-di-tert-butylphenol, 2,6-di-tert-butyl-p-ethylphenol, pentanols include 2,4-di-tert-amylphenol, others include o-ethoxyphenol, o-ethoxybenzene Methyl ether, p-ethyl guaiacol, 2,6-diisopropylanisole).

Reference： [1]Patent: CN107586255,2018,A .Location in patent: Paragraph 0043-0044; 0070

27
[ 591-50-4 ]
[ 620-17-7 ]
[ 29679-58-1 ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 11393 - 11397

28
[ 64-17-5 ]
[ 90-05-1 ]
[ 90-00-6 ]
[ 128-39-2 ]
[ 620-17-7 ]
[ 2934-05-6 ]
[ 2078-54-8 ]
[ 4130-42-1 ]
[ 105-05-5 ]
[ 1197-34-8 ]
[ 5875-45-6 ]
[ 102-25-0 ]
[ 2785-89-9 ]
[ 876-20-0 ]
[ 40625-96-5 ]
[ 2715-54-0 ]
[ 6630-01-9 ]
[ 100-66-3 ]
[ 108-95-2 ]

Yield	Reaction Conditions	Operation in experiment
	With perrhenic acid anhydride; at 320℃; for 6h;Inert atmosphere; Sealed tube;	General procedure: The catalytic reactions were carried out in a batch reactor (ParrInstruments, 300 mL). In a typical model compound conversion experiment,the reactor was loaded with 0.1 g catalyst, 1 g substrate,60 mL solvent, sealed and purged with N2 five times. The reactor wasthen heated to the desired reaction temperature within 1.5 h and kept atthis temperature for the desired reaction time with stirring at 550 rpm.The reaction time was denoted as 0 h when the prescribed reactiontemperature was reached. After the reaction, the reactor was firstlycooled in air by removing the heating jacket. On reaching below 150 C,the reactor was further cooled by immersing it into cold-water. Thepost-reaction solution and the spent catalyst were separated by filtration.The solution mixture was analyzed with an Agilent Technologies6890 N gas chromatograph (GC) equipped with a HP-5 MS capillarycolumn (Agilent, 30m ×0.25mm ×0.25 mum) and a FID detector withanisole as the internal standard. However, when the substrate was anisole,tridecane was chosen as the internal standard. The GC parameterswere: inlet temperature 280 C, detector temperature 300 C, split ratio1:50. The oven temperature ramped from 45 C to 105 C at 15 Cmin-1, and then ramped to 280 C at 6 C min-1. Products wereidentified with a gas chromatograph-mass spectroscopy (GC-MS,Agilent Technologies, model 5973). The mass spectrum acquired withthe GC-MS was retrieved in the NIST Mass Spectral Library to identifythe structure of each product.

Reference： [1]Catalysis Today,2019

29
[ 620-17-7 ]
[ 2349-70-4 ]

Yield	Reaction Conditions	Operation in experiment
71.7%	With D-Glucose; oxygen; quintuple recombinant E_. coli cells coexpressing P₄₅₀ BM₃ monooxygenase F₈₇V/L₁₈₈P/I₄₀₁P/R₄₇L/Y₅₁F and glucose dehydrogenase; NADPH In aq. phosphate buffer; dimethyl sulfoxide at 25℃; for 12h; Green chemistry; Enzymatic reaction; regioselective reaction;

Reference： [1]Gaikaiwari, Anand Raghavendra; Li, Ren-Jie; Li, Xirui; Li, Zhi; Tian, Kaiyuan [ACS Catalysis, 2022, p. 5939 - 5948]

30
[ 620-17-7 ]
[ 2349-70-4 ]
[ 1124-39-6 ]

Yield	Reaction Conditions	Operation in experiment
	With D-Glucose; oxygen; recombinant E_. coli cells coexpressing P₄₅₀ BM₃ monooxygenase F₈₇V and glucose dehydrogenase; NADPH In aq. phosphate buffer at 22℃; for 2h; Green chemistry; Enzymatic reaction; regioselective reaction;
	With D-Glucose; oxygen; triple recombinant E_. coli cells coexpressing P₄₅₀ BM₃ monooxygenase F₈₇V/L₁₈₈P/R₄₇I and glucose dehydrogenase; NADPH In aq. phosphate buffer at 22℃; for 2h; Green chemistry; Enzymatic reaction; regioselective reaction;

Reference： [1]Gaikaiwari, Anand Raghavendra; Li, Ren-Jie; Li, Xirui; Li, Zhi; Tian, Kaiyuan [ACS Catalysis, 2022, p. 5939 - 5948]
[2]Gaikaiwari, Anand Raghavendra; Li, Ren-Jie; Li, Xirui; Li, Zhi; Tian, Kaiyuan [ACS Catalysis, 2022, p. 5939 - 5948]

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P342	If experiencing respiratory symptoms:
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P378
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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
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P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
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P401
P402	Store in a dry place.
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 620-17-7 ] {[proInfo.proName]}

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[ 620-17-7 ] Synthesis Path-Upstream 1~5

[ 620-17-7 ] Synthesis Path-Downstream 1~30

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