[ CAS No. 5460-32-2 ] {[proInfo.proName]}

Name: 5460-32-2|4-Iodo-1,2-dimethoxybenzene|97%
Brand: Ambeed
SKU: A478247
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2D 3D

Structure of 5460-32-2 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 5460-32-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 5460-32-2 ]

SDS Specification

Alternatived Products of [ 5460-32-2 ]

Product Details of [ 5460-32-2 ]

CAS No. :	5460-32-2	MDL No. :	MFCD00094416
Formula :	C₈H₉IO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PUCISUQLWLKKJH-UHFFFAOYSA-N
M.W :	264.06	Pubchem ID :	230307
Synonyms :

Calculated chemistry of [ 5460-32-2 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	52.14
TPSA :	18.46 Å²

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) :	-6.42 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.43
Log Po/w (XLOGP3) :	2.1
Log Po/w (WLOGP) :	2.31
Log Po/w (MLOGP) :	2.37
Log Po/w (SILICOS-IT) :	2.78
Consensus Log Po/w :	2.4

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.07
Solubility :	0.224 mg/ml ; 0.000848 mol/l
Class :	Soluble
Log S (Ali) :	-2.12
Solubility :	2.01 mg/ml ; 0.00762 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.6
Solubility :	0.0656 mg/ml ; 0.000248 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.38

Safety of [ 5460-32-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 5460-32-2 ]

* 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 [ 5460-32-2 ]
Downstream synthetic route of [ 5460-32-2 ]

[ 5460-32-2 ] Synthesis Path-Upstream 1~1

1
[ 5460-32-2 ]
[ 808-57-1 ]

Reference： [1] Journal of the American Chemical Society, 1980, vol. 102, # 21, p. 6504 - 6512

[ 5460-32-2 ] Synthesis Path-Downstream 1~88

1
[ 91-16-7 ]
[ 5460-32-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With N-iodo-succinimide; trifluoroacetic acid; In acetonitrile; at 80℃; for 2h;	To a stirred solution of 1,2-dimethoxybenzene 7 (1mL, 7.85mmol) in acetonitrile (5mL) was added N-iodosuccinimide (NIS) (1.94g, 8.63mmol) and trifluoroacetic acid (TFA) (0.18mL, 2.35mmol). The mixture was stirred for 2hat 80C. After that period the resulting mixture was poured into ice (20g) and water (100mL) and a saturated solution of sodium thiosulfate was added. The aqueous layer was extracted with dichloromethane (3×100mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using dichloromethane as eluent to give the desired 4-iodo-1,2-dimethoxybenzene 8 in excellent yield (1.97g, 95%). This compound showed spectroscopic and analytical data identical to one previously reported [37].
85%	With 3-iodo-4,4-dimethyloxazolidin-2-one; In acetonitrile; for 15h;Reflux;	[00274] A mixture of veratrole (0.22 g, 1.63 mmol), 3-iodo-4,4- dimethyloxazolidin-2-one (0.6 g, 2.44 mmol) and MeCN (10 mL) was stirred under reflux conditions for 15 h and concentrated in vacuo. The residue was treated with 1 M aq Na2S03 (5 mL), extracted with hexane (3 x 10 mL) and then with DCM (3 x 10 mL). The combined DCM extracts were dried over Na2S04, filtered and concentrated in vacuo to give 0.27 g (95%) of 4,4-dimethyl-2- oxazolidinone. The combined hexane extracts were washed with 1 M aq Na2S03 (10 mL), dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (eluent hexane/DCM 100:0 to 0:100 v/v) to give 0.36 g (85%) of 4-iodo- 1,2-dimethoxybenzene. 1H NMR: δ 7.19 (dd, J = 1.5 Hz, J = 8.5 Hz, 1H), 7.09 (d, J = 1.5 Hz, 1H), 6.59 (d, J = 8.5 Hz, 1H), 3.83 (s, 3H), 3.82 (s, 3H) ppm; 13C NMR: δ 149..8, 149.1, 129.7, 120.3, 113.2, 82.3, 56.1, 55.9 ppm.
68%	With N-iodosaccharine; at 20℃;Ionic liquid; Darkness;	General procedure: To a solution of 54 mg (0.5 mmol) of anisole in 1 mL of BMIM BF4 was added 158 mg (0.51 mmol) of N-iodosaccharin. The reaction was stirred at room temperature protected from light for 8-12 h. The product was then isolated by extraction with ether (3 × 3 mL), followed by evaporation of the solvent to afford the desired iodinated product. In some cases, the product was contaminated with small amounts of BMIM BF4. This could be removed via filtration with ether through a short plug of silica. Alternatively, it could be avoided entirely by extraction of the product from the reaction using 1:1 ether/hexanes in place of pure ether. The identity of all products were confirmed by comparison (spectral and mp) with either commercially available samples or data reported in the literature as indicated in Table 1.

61%	With 1-iodo-3,5,5-trimethylhydantoin; In acetonitrile; at 20℃; for 48h;	[00276] A mixture of veratrole (0.22 g, 1.63 mmol), l-iodo-3,5,5- trimethylhydantoin (0.53 g, 1.97 mmol) and MeCN (10 mL) was stirred for 48 h at rt and concentrated in vacuo. The residue was treated with 1 M aq Na2S03 (5 mL), extracted with hexane (3 x 10 mL) and then with DCM (3 x 10 mL). The combined DCM extracts were dried over Na2S04, filtered and concentrated in vacuo to give 0.25 g (90%) of 3,5,5-trimethylhydantoin (3,5,5-TMH). The combined hexane extracts were washed with 1 M aq Na2S03 (10 mL), dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (eluent hexane/DCM 100:0 to 0: 100 v/v) to give 0.31 g (61%) of 4-iodo-l,2-dimethoxybenzene.
	With N-iodo-succinimide; trifluoroacetic acid; In acetonitrile;Reflux;	General procedure: To a solution of the appropriate benzene derivative 6a,b (1.0 mmol) in acetonitrile (20 mL) were added NIS (0.247 g, 1.1 mmol) and a catalytic amount of TFA (0.023 mL, 0.3 mmol). The reaction mixture was stirred at reflux overnight. After this time, it was poured onto ice (50 g) and H2O (100 mL) and then, it was treated with a saturated solution of Na2S2O3. The obtained precipitate was filtered off, taken in CH2Cl2 and dried over anhydrous Na2SO4. The solvent was evaporated to dryness and the obtained residue was purified by silica gel column chromatography using CH2Cl2/C6H14 (1:1) as eluent.

Reference： [1]Organic Preparations and Procedures International,2002,vol. 34,p. 647 - 651
[2]Synthetic Communications,2003,vol. 33,p. 1319 - 1323
[3]Journal of Organic Chemistry,2002,vol. 67,p. 8622 - 8624
[4]Tetrahedron Letters,2002,vol. 43,p. 5047 - 5048
[5]Chemistry Letters,1988,p. 795 - 798
[6]European Journal of Organic Chemistry,2012,p. 5935 - 5942,8
[7]Journal of Organic Chemistry,2003,vol. 68,p. 9510 - 9512
[8]European Journal of Medicinal Chemistry,2016,vol. 115,p. 381 - 392
[9]Advanced Synthesis and Catalysis,2013,vol. 355,p. 1243 - 1248
[10]European Journal of Organic Chemistry,2005,p. 2689 - 2693
[11]Advanced Synthesis and Catalysis,2004,vol. 346,p. 77 - 82
[12]Organic Preparations and Procedures International,2005,vol. 37,p. 279 - 283
[13]Journal of Chemical Research,2006,p. 366 - 368
[14]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3998 - 4004
[15]Synthesis,1995,p. 1273 - 1277
[16]Synthesis,2013,vol. 45,p. 1635 - 1640
[17]Tetrahedron Letters,1996,vol. 37,p. 4081 - 4084
[18]Patent: WO2015/68159,2015,A2 .Location in patent: Paragraph 00273-00274
[19]Catalysis science and technology,2014,vol. 4,p. 4308 - 4312
[20]European Journal of Organic Chemistry,2019,vol. 2019,p. 696 - 704
[21]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1991,vol. 30,p. 522 - 524
[22]Organic and Biomolecular Chemistry,2007,vol. 5,p. 699 - 707
[23]Bulletin of the Chemical Society of Japan,1981,vol. 54,p. 2847 - 2848
[24]Synthesis,2006,p. 2603 - 2607
[25]Tetrahedron Letters,2011,vol. 52,p. 2413 - 2414
[26]Australian Journal of Chemistry,2008,vol. 61,p. 946 - 955
[27]Chemical Communications,2004,p. 2052 - 2053
[28]European Journal of Organic Chemistry,2017,vol. 2017,p. 3234 - 3239
[29]Patent: WO2015/68159,2015,A2 .Location in patent: Paragraph 00275-00276
[30]Journal of Materials Chemistry A,2017,vol. 5,p. 12080 - 12085
[31]Synthesis,1995,p. 926 - 928
[32]Journal of Organic Chemistry,2019,vol. 84,p. 4149 - 4164
[33]Australian Journal of Scientific Research, Series A: Physical Sciences,1949,vol. <A> 2,p. 595,596
[34]Organic Syntheses,1963,vol. Coll. Vol. IV,p. 547
[35]Journal of the Chemical Society,1955,p. 4435,4439
[36]Journal of Organic Chemistry,1957,vol. 22,p. 1271
[37]Monatshefte fur Chemie,1913,vol. 34,p. 647
[38]Justus Liebigs Annalen der Chemie,1960,vol. 634,p. 84 - 104
[39]Tetrahedron Letters,1997,vol. 38,p. 6225 - 6228
[40]Journal of Organic Chemistry,2006,vol. 71,p. 1027 - 1032
[41]Chemistry - A European Journal,2006,vol. 12,p. 7398 - 7410
[42]Tetrahedron Letters,2004,vol. 45,p. 8015 - 8018
[43]Organic Letters,2009,vol. 11,p. 4978 - 4981
[44]Science,2014,vol. 343,p. 853 - 857
[45]European Journal of Medicinal Chemistry,2016,vol. 119,p. 250 - 259
[46]Chemical Communications,2022,vol. 58,p. 847 - 850

2
[ 5460-32-2 ]
[ 2026-27-9 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 6248 - 6250
[2]Bulletin of the Chemical Society of Japan,1980,vol. 53,p. 1767 - 1768
[3]Monatshefte fur Chemie,1913,vol. 34,p. 647
[4]Monatshefte fur Chemie,1913,vol. 34,p. 647
[5]Chemische Berichte,1967,vol. 100,p. 2854 - 2869
[6]Chemische Berichte,1967,vol. 100,p. 2842 - 2853

3
[ 1191-99-7 ]
[ 5460-32-2 ]
[ 124266-47-3 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 407 - 408

4
[ 5460-32-2 ]
[ 41934-47-8 ]
[ 131882-59-2 ]

Yield	Reaction Conditions	Operation in experiment
27%	In acetonitrile Irradiation;
27%	In acetonitrile Irradiation;

Reference： [1]Kirpichenok, M. A.; Mel'nikova, L. M.; Denisov, L. K.; Grandberg, I. I. [Chemistry of Heterocyclic Compounds, 1990, vol. 26, # 8, p. 858 - 862][Khimiya Geterotsiklicheskikh Soedinenii, 1990, # 8, p. 1028 - 1032]
[2]Kirpichenok, M. A.; Mel'nikova, L. M.; Denisov, L. K.; Grandberg, I. I. [Chemistry of Heterocyclic Compounds, 1990, vol. 26, # 8, p. 858 - 862][Khimiya Geterotsiklicheskikh Soedinenii, 1990, # 8, p. 1028 - 1032]

5
[ 5460-32-2 ]
[ 85311-89-3 ]
[ 79445-44-6 ]

Reference： [1]Tetrahedron,1986,vol. 42,p. 3981 - 3986

6
[ 5460-32-2 ]
[ 808-57-1 ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 6504 - 6512

7
[ 5460-32-2 ]
[ 19179-34-1 ]

Reference： [1]Angewandte Chemie - International Edition,2021,vol. 60,p. 15832 - 15837
    Angew. Chem.,2021,vol. 133,p. 15966 - 15971
[2]Journal of the American Chemical Society,1980,vol. 102,p. 6504 - 6512
[3]Chemical Communications,2008,p. 4750 - 4752
[4]Chemical Communications,2002,p. 1278 - 1279
[5]Russian Journal of Organic Chemistry,1994,vol. 30,p. 1946 - 1980
    Zhurnal Organicheskoi Khimii,1994,vol. 30,p. 1847 - 1881
[6]Russian Journal of Organic Chemistry,1998,vol. 34,p. 1589 - 1626
[7]Journal of Materials Chemistry A,2017,vol. 5,p. 12080 - 12085
[8]Angewandte Chemie - International Edition,2018,vol. 57,p. 2450 - 2454
    Angew. Chem.,2018,vol. 130,p. 2475 - 2479,5
[9]Advanced Synthesis and Catalysis,2004,vol. 346,p. 675 - 681
[10]Organic Letters,2018,vol. 20,p. 4107 - 4110
[11]Journal of Organic Chemistry,1977,vol. 42,p. 764 - 765

8
[ 5460-32-2 ]
[ 16750-63-3 ]
[ 107365-58-2 ]

Reference： [1]Tetrahedron,1986,vol. 42,p. 2111 - 2116

9
[ 5460-32-2 ]
[ 79-06-1 ]
[ 130973-10-3 ]

Reference： [1]Synthetic Communications,1990,vol. 20,p. 3563 - 3574
[2]Synthesis,1991,p. 539 - 542

10
[ 5460-32-2 ]
[ 105-56-6 ]
[ 36848-69-8 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; sodium hydride 1.) HMPT, 25 deg C, 10 min; 2.) 90-95 deg C, 3 h; Yield given. Multistep reaction;
	With copper(l) iodide; sodium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide at 90 - 95℃; for 2h;

Reference： [1]Osuka, Atsuhiro; Kobayashi, Tsutomu; Suzuki, Hitomi [Synthesis, 1983, # 1, p. 67 - 68]
[2]Suzuki, Hitomi; Kobayashi, Tsutomu; Yoshida, Yoshiki; Osuka, Atsuhiro [Chemistry Letters, 1983, p. 193 - 194]

11
[ 5460-32-2 ]
[ 7605-28-9 ]
[ 112520-84-0 ]

Reference： [1]Chemistry Letters,1987,p. 887 - 890

12
[ 5460-32-2 ]
[ 2633-66-1 ]
[ 107365-59-3 ]

Reference： [1]Tetrahedron,1986,vol. 42,p. 2111 - 2116

13
[ 5460-32-2 ]
[2-(9-bora-bicyclo[3.3.1]non-9-yl)-ethyl]-carbamic acid benzyl ester [ No CAS ]
[ 63914-27-2 ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 8743 - 8744

14
[ 20469-63-0 ]
[ 5460-32-2 ]
copper-powder [ No CAS ]
[ 3153-72-8 ]
[ 2026-27-9 ]
[ 170649-97-5 ]

Reference： [1]Monatshefte fur Chemie,1930,vol. 55,p. 342,349

15
[ 5460-32-2 ]
[ 282734-33-2 ]
[ 71953-00-9 ]
(2S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(3',4'-dimethoxyphenyl)propionic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	Stage #1: (2R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-iodopropionic acid tert-butyl ester With chloro-trimethyl-silane; zinc In N,N-dimethyl-formamide at 20℃; Stage #2: 1-iodo-3,4-dimethoxybenzene With tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 50℃; for 4h;

Reference： [1]Deboves; Montalbetti; Jackson [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2001, # 16, p. 1876 - 1884]

16
[ 5460-32-2 ]
[ 115-19-5 ]
[ 51792-65-5 ]

Reference： [1]Russian Chemical Bulletin,2001,vol. 50,p. 868 - 873
[2]European Journal of Organic Chemistry,2019,vol. 2019,p. 696 - 704
[3]Advanced Synthesis and Catalysis,2018,vol. 360,p. 153 - 160
[4]Archiv der Pharmazie,2020,vol. 353

17
[ 7223-38-3 ]
[ 5460-32-2 ]
[3-(3,4-dimethoxy-phenyl)-prop-2-ynyl]-dimethyl-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2565 - 2568

18
[ 5460-32-2 ]
[ 244037-28-3 ]

Yield	Reaction Conditions	Operation in experiment
82%	With hydrogenchloride; dihydrogen peroxide; acetic acid; In water; at 15 - 25℃; for 12h;	In a 100 ml reaction flask equipped with an exhaust gas absorption device 2.64 g of <strong>[5460-32-2]4-iodo-1,2-dimethoxybenzene</strong> and 26 ml of acetic acid, then add 30ml concentrated hydrochloric acid, control the reaction liquid temperature 15-20 degrees,dilute 10 ml of hydrogen peroxide diluted with 5 ml of glacial acetic acid, drop finished, dept at 15-25 degrees for 12 hours for sample HPLC monitoring, raw materials less than 1% about 30 ml of saturated sodium bisulfite solution was added and filtered, the filter cake was transferred to a 100 ml reaction flask, 10 ml of acetic acid and 30 ml of water were added, The temperature was raised to 50-55 C for 1 hour, down to room temperature filtration, with a little water rinse, TLC test for a single spot. To give 3.04 white solid in 82% yield. HPLC greater than 97.9 %

Reference： [1]Patent: CN105732333,2016,A .Location in patent: Paragraph 0019-0021
[2]Chemical Research in Toxicology,1999,vol. 12,p. 690 - 699

19
[ 67756-04-1 ]
[ 5460-32-2 ]
[ 100753-43-3 ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 2894 - 2898

20
[ 5460-32-2 ]
[ 352432-33-8 ]
[ 791637-59-7 ]

Reference： [1]Chemical Communications,2004,p. 2052 - 2053

21
[ 864755-84-0 ]
[ 5460-32-2 ]
[ 864755-88-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; at 20℃; for 4h;	3-[4-(3,4-Dimethoxyphenyl)-but-3-ynyl]-1,3-oxazolidin-2-one (34). Triethylamine (0.08 mL, 0.574 mmol) and Pd(PPh3)Cl2 (8.0 mg, 0.011 mmol) were added to a mixture of 3,4-dimethoxyphenyl iodide (33) (64 mg, 0.242 mmol) and alkyne 25 (34 mg, 0.245 mmol) in THF (3 mL) at room temperature. Then Cu(I)I (5 mg, 0.026 mmol) was added. The resulting mixture was stirred at room temperature for 4 h. The reaction was quenched with water (10 mL) and concentrated to remove the organic solvents. The residue was diluted with ethyl acetate (15 mL). The organic layer was separated and washed with brine (2×10 mL), dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (25 g), eluting with EtOAc-hexanes (10-50%) to afford the product 34 (54 mg) as solid in 80% yield: mp 78-79 C. 1H NMR (300 MHz, CDCl3) δ 6.95 (dd, J=2.1 Hz, J=8.4 Hz, 1H), 6.88 (d, J=1.8 Hz, 1H), 6.76 (d, J=8.4 Hz, 1H), 4.32 (t, J=7.8 Hz, 2H), 3.86 (s, 3H), 3.85 (s, 3H), 3.73 (t, J=7.8 Hz, 2H), 3.51 (t, J=6.6 Hz, 2H), 2.67 (t, J=6.6 Hz, 2H); ESIMS m/z (rel intensity) 276.05 (MH+, 94), 298.05 (MNa+, 98). Anal. (C15H17NO4) C, H, N.

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 6140 - 6155
[2]Patent: US2008/300288,2008,A1 .Location in patent: Page/Page column 22; 8

22
1-(tributylstannanyl)-2-methoxy-3-methyl-5-[4-(2-oxo-oxazolidin-3-yl)-but-1-enyl]benzoic acid methyl ester [ No CAS ]
[ 5460-32-2 ]
5-[(E)-1-(3,4-Dimethoxy-phenyl)-4-(2-oxo-oxazolidin-3-yl)-but-1-enyl]-2-methoxy-3-methyl-benzoic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 6140 - 6155

23
[ 5460-32-2 ]
[ 1066-54-2 ]
[ 863132-17-6 ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 2689 - 2693
[2]Synlett,2011,p. 2397 - 2401
[3]Chemical Communications,2022,vol. 58,p. 5156 - 5159

24
[ 5460-32-2 ]
[ 89978-46-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With bromine; sodium hydrogensulfite; In P2 O5; acetic acid;	4-Iodoveratrole (26.0 g, 0.0985M) in acetic acid (25 ml) was treated with bromine (6.5 ml, 0.127M) in acetic acid (30 ml) and stirred at room temperature for one hour. The mixture was diluted with water (300 ml) and treated with sodium bisulfite to discharge the excess bromine. The white solid was filtered, washed with water and dried in vacuo over P2 O5 to give 4-bromo-5-iodoveratrole (33.0 g, 95% yield) as a white solid, mp 98-100 C. (literature: Baker et al., J. Chem. Soc. 3986 (1961), mp 102-104 C.). NMR (CDCl3) δ 3.83 ppm (s, 6H, (2x) OCH3), 7.06 (s, 1H, ArH), 7.21 (s, 1H, ArH).

Reference： [1]Patent: US4761413,1988,A
[2]Chemistry - A European Journal,2006,vol. 12,p. 7398 - 7410

25
[ 944584-13-8 ]
[ 5460-32-2 ]
dimethyl (2E)-2,3-bis(3,4-dimethoxydibenzylidene)succinate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 4900 - 4904

26
[ 952600-30-5 ]
[ 5460-32-2 ]
2,2,2-trifluoroethyl (Z)-2-acetoxy-3-(3,4-dimethoxyphenyl)acrylate [ No CAS ]

Reference： [1]Synthesis,2007,p. 2249 - 2272

27
[ 5460-32-2 ]
[ 107-18-6 ]
[ 40181-00-8 ]
[ 61871-67-8 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 356 - 363
[2]Tetrahedron,2012,vol. 68,p. 1745 - 1749

28
[ 5460-32-2 ]
[ 4302-52-7 ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 2689 - 2693
[2]Russian Chemical Bulletin,2001,vol. 50,p. 868 - 873
[3]Advanced Synthesis and Catalysis,2018,vol. 360,p. 153 - 160
[4]European Journal of Organic Chemistry,2019,vol. 2019,p. 696 - 704
[5]Archiv der Pharmazie,2020,vol. 353
[6]Chemical Communications,2022,vol. 58,p. 5156 - 5159

29
[ 5460-32-2 ]
[ 37055-80-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 62 percent / benzene / 8 h / Irradiation 2: sodium iodide, trimethylsilyl chloride / CHCl₃ / 16 h

Reference： [1]Urban, Jan; Kuzmic, Petr; Saman, David; Soucek, Milan [Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 10, p. 2482 - 2491]

30
[ 5460-32-2 ]
[ 3598-30-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: copper powder 2: hydriodic acid; phosphonium iodide

Reference： [1]Spaeth; Gibian [Monatshefte fur Chemie, 1930, vol. 55, p. 342,349]

31
[ 636-93-1 ]
[ 5460-32-2 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1907,vol. 144,p. 758
Bulletin de la Societe Chimique de France,1907,vol. <4> 1,p. 932
Chemisches Zentralblatt,1907,vol. 78,p. 976

32
[ 1826-11-5 ]
[ 5460-32-2 ]
[ 1000029-24-2 ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 7996 - 8000

33
[ 20662-88-8 ]
[ 5460-32-2 ]
[ 70216-32-9 ]

Reference： [1]Chemical Communications,2008,p. 1241 - 1243

34
[ 4302-52-7 ]
[ 5460-32-2 ]
[ 79238-81-6 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2976 - 2979
[2]Journal of Organic Chemistry,2009,vol. 74,p. 9554 - 9557
[3]Organic Letters,2020,vol. 22,p. 924 - 928
[4]Chemistry of Heterocyclic Compounds,2008,vol. 44,p. 1257 - 1261

35
[ 925422-49-7 ]
[ 5460-32-2 ]
[ 1186721-95-8 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 6929 - 6935

36
[ 925422-32-8 ]
[ 5460-32-2 ]
[ 1186721-93-6 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 6929 - 6935

37
[ 1186723-00-1 ]
[ 5460-32-2 ]
[ 1186721-97-0 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 6929 - 6935

38
[ 470-17-7 ]
[ 5460-32-2 ]
[ 1192803-30-7 ]
[ 1192803-33-0 ]

Reference： [1]Doklady Chemistry,2009,vol. 426,p. 138 - 142

39
[ 5460-32-2 ]
[ 546-43-0 ]
[ 1192803-35-2 ]
[ 1192803-36-3 ]

Reference： [1]Doklady Chemistry,2009,vol. 426,p. 138 - 142

40
[ 470-17-7 ]
[ 5460-32-2 ]
[ 1192803-30-7 ]
[ 1265907-83-2 ]
[ 1265907-95-6 ]

Reference： [1]Russian Journal of Organic Chemistry,2010,vol. 46,p. 1719 - 1734

41
[ 201230-82-2 ]
[ 20059-73-8 ]
[ 5460-32-2 ]
[ 122898-67-3 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 6061 - 6071

42
[ 20059-73-8 ]
[ 5460-32-2 ]
[ 1641-69-6 ]
[ 1285695-20-6 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 6061 - 6071

43
[ 100-42-5 ]
[ 5460-32-2 ]
[ 82102-37-2 ]
(E)-3-(2-bromophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one [ No CAS ]

Reference： [1]Organic Letters,2011,vol. 13,p. 2444 - 2447

44
[ 5460-32-2 ]
[ 82560-12-1 ]
[ 1338815-15-8 ]

Yield	Reaction Conditions	Operation in experiment
31%	With copper(l) iodide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; potassium carbonate; In toluene; for 16h;Inert atmosphere; Reflux;	Intermediate A19: 3-ferf-Butyl-1 -(3,4-dimethoxyphenyl)-1W-pyrazol-5-amine.Intermediate A19To a solution of 4-iodo-1 ,2-dimethoxybenzene (1 .10 g, 4.17 mmol) in anhydrous toluene (5.0 mL) was added 3-ierf-butyl-1 - -pyrazol-5-amine (638 mg, 4.58 mmol) followed by (1 R,2f?)- /V1,A 2-dimethylcyclohexane-1 ,2-diamine (130 μ, 0.83 mmol) and potassium carbonate (1.15 g, 8.3 mmol). The mixture was purged with N2, copper(l) iodide (40 mg, 0.21 mmol) was added and the reaction mixture was heated at reflux under N2 for 16 hr. The resulting mixture was cooled to RT and was partitioned between EtOAc (100 mL) and water (150 mL). The organic layer was separated and was washed with aq. citric acid solution (10% w/v, 50 mL) followed by brine (50 mL) and then dried and evaporated in vacuo. The residue was purified by flash column chromatography (S1O2, 80 g, EtOAc in isohexane, 0-70%, gradient elution). The impure product so obtained was dissolved in ether (1.0 mL), isohexane (10 mL) was added and the resulting precipitate was collected by filtration to afford the title compound, Intermediate A19, as a purple solid (364 mg, 31 %); R' 3.55 min (Method 1 ); m/z 276 (M+H)+ (ES+). Intermediate 20: 3-ferf-Butyl-1 -(4-methylthiophen-2-yl)-1W-pyrazol-5-amine.

Reference： [1]Patent: WO2011/124930,2011,A1 .Location in patent: Page/Page column 46

45
[ 5460-32-2 ]
[ 33513-42-7 ]
[ 2024-83-1 ]

Yield	Reaction Conditions	Operation in experiment
81%	With N,N,N,N,-tetramethylethylenediamine; copper diacetate; ammonium bicarbonate at 150℃; for 22h; sealed tube;

Reference： [1]Zhang, Guoying; Ren, Xinyi; Chen, Jianbin; Hu, Maolin; Cheng, Jiang [Organic Letters, 2011, vol. 13, # 19, p. 5004 - 5007]

46
C₂₃H₂₇NO₆S [ No CAS ]
[ 5460-32-2 ]
C₃₁H₃₅NO₈S [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 19076 - 19079
[2]Journal of Organic Chemistry,2014,vol. 79,p. 2430 - 2452

47
[ 5460-32-2 ]
[ 4439-02-5 ]
2-(benzo[d][1,3]dioxol-5-yl)-1-(3,4-dimethoxyphenyl)ethanone [ No CAS ]

Reference： [1]Organic Letters,2012,vol. 14,p. 1282 - 1285

48
[ 5460-32-2 ]
[ 768-60-5 ]
[ 73867-60-4 ]

Yield	Reaction Conditions	Operation in experiment
31.6%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In acetonitrile; at 80℃; for 3h;Inert atmosphere; Sealed tube;	General procedure: To a mixture of Pd(PPh3)2Cl2(0.086 g, 0.12 mmol), CuI (0.047 g, 0.24 mmol), and Et3N (0.51 mL, 3.66 mmol) in MeCN (20 mL) were added substituted phenylacetylene (2.44 mmol) and substituted iodobenzene (2.21 mmol). The reaction mixture was recharged with argon and stirred at 80C for 3 h in a sealed tube. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl and concentrated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 10:1) to afford pure product.

Reference： [1]Organic Letters,2012,vol. 14,p. 2976 - 2979
[2]European Journal of Medicinal Chemistry,2017,vol. 136,p. 382 - 392

49
[ 5460-32-2 ]
[ 73663-61-3 ]
[ 1394840-87-9 ]

Yield	Reaction Conditions	Operation in experiment
51%	With copper(l) iodide; sodium carbonate; triphenylphosphine; In N,N-dimethyl-formamide; at 160℃; for 3h;	A suspension of 0.212 g of Na2C03 (2 mmol), 0.262 g of PPh3 (1 mmol), 0.206 g (1 mmol) of 31 and 0.316 g of 4-iodoveratrole (1.2 mmol) was formed in 1 mL of DMF. Then, 0.190 g (1 mmol) of Cul was added. The mixture was stirred at 160 C for 3 h and quenched by pouring into 50 mL of water containing 5% NH4+OH~. The product was extracted with 50 mL DCM, the organic layer dried and concentrated, and the crude product purified by PTLC to give 0.174 g (51% yield) of 32 as a yellow solid. 1H NMR (200 MHz, CDC13) δ 7.60 (d, / = 8.4 Hz, 1H), 7.54, (bs, 1H), 7.24 (s, 1H), 7.19 (bs, 1H), 7.10 (s, 1H), 6.90-6.83 (m, 2H), 3.91-3.86 (4 overlapping multiplets, 12H). 13C NMR (50 MHz, CDC13) δ 160.7, 150.9, 149.3, 149.2, 132.1, 132.0, 122.0, 121.2, 120.4, 119.3, 117.1, 111.5, 111.1, 109.1, 107.5, 56.01, 55.92

Reference： [1]Patent: WO2012/118935,2012,A1 .Location in patent: Page/Page column 46

50
[ 5460-32-2 ]
[ 108-98-5 ]
[ 82102-37-2 ]
S-phenyl 3,4-dimethoxybenzenecarbothioate [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 948 - 951

51
[ 5460-32-2 ]
[ 18414-58-9 ]
[ 93-07-2 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 1378 - 1381

52
[ 667-27-6 ]
[ 5460-32-2 ]
[ 125575-35-1 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 2648 - 2651

53
[ 5460-32-2 ]
[ 57-13-6 ]
[ 2024-83-1 ]

Yield	Reaction Conditions	Operation in experiment
58%	With copper (II)-fluoride; 1,10-Phenanthroline; oxygen; lithium carbonate; In dimethyl sulfoxide; at 150℃; for 36h;Sealed tube;	General procedure: Under Oxygen, a reaction tube was charged with p-iodoanisole (46.3 mg, 0.2 mmol), urea (48.0 mg, 0.8 mmol), CuF2 (4.1 mg, 0.04 mmol), L1 (10.8 mg, 0.06 mmol), Li2CO3 (44.3 mg, 0.6mmol) and DMSO (2 mL). The mixture was stirred at 150 oC for 36 h. After the completion of the reaction, monitored by TLC, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel to give the product.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 5250 - 5252

54
[ 5460-32-2 ]
[ 84-58-2 ]
[ 2024-83-1 ]

Reference： [1]Chinese Journal of Chemistry,2013,vol. 31,p. 449 - 452

55
[ 1448704-68-4 ]
[ 5460-32-2 ]
[ 1448704-69-5 ]

Yield	Reaction Conditions	Operation in experiment
37%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In acetonitrile; at 120℃; for 0.333333h;Microwave irradiation; Inert atmosphere;	Step E: A mixture of the intermediate prepared in Step D, (S)-tert-butyl 4-(4-ethynyl- 3-(methoxycarbonyl)phenyl)-2-methylpiperazine-l-carboxylate (716 mg, 2.0 mmol), 4-iodo-l,2- dimethoxybenzene (634 mg, 2.4 mmol), Cul (19.0 mg, 0.1 mmol), PdCl2(Ph3P)2(70 mg, 0.1 mmol), Et3N (0.56 mL, 202 mg, 4.0 mmol) and acetonitrile (2.0 mL) was irradiated in a microwave reactor, under argon at 120 C for 20 minutes. The mixture was then cooled and chromatographed twice (silica gel, ethyl acetate in hexanes, 0-50%, then ethyl acetate in dichloromethane, 7.5%) to give the alkyne intermediate as a yellow oil (367 mg, 37%). MS m/z 495.3 [M+H]+.

Reference： [1]Patent: WO2013/112788,2013,A1 .Location in patent: Paragraph 00624

56
[ 5331-43-1 ]
[ 5460-32-2 ]
benzyl 1-(3,4-dimethoxyphenyl)hydrazinecarboxylate [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 6058 - 6061

57
[ 470-17-7 ]
[ 5460-32-2 ]
[ 1192803-30-7 ]
[ 1265907-83-2 ]

Reference： [1]Russian Chemical Bulletin,2012,vol. 61,p. 1975 - 1985
Izv. Akad. Nauk, Ser. Khim.,2012,vol. 61,p. 1959 - 1968,11

58
[ 5460-32-2 ]
[ 114642-97-6 ]
[ 1528744-50-4 ]

Yield	Reaction Conditions	Operation in experiment
53%		General procedure: To a solution of iodobenzene (5.77 g, 28.3 mmol) in anhydrous THF (60 mL) was added a 1.0 M solution of i-PrMgCl in anhydrous THF (28.3 mL, 28.3 mmol) over 20 min at -25 C, and the resulting mixture was stirred for 1 h at -25 C. After cooling to -75 C, a solution of 3-azidopropanal (1.3 g, 13.0 mmol) in anhydrous THF (23 mL) was added dropwise over 20 min. After stirring for 1 h at -75 C, the reaction mixture was quenched by saturated aqueous NH4Cl. The mixture was extracted with EtOAc. The combined extract was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography (petroleum ether/ethyl acetate, 20:1 to 9:1) to give a brown oil, 1.20 g (52% yield).

Reference： [1]Tetrahedron,2014,vol. 70,p. 643 - 649

59
[ 1583285-88-4 ]
[ 5460-32-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With Iodine monochloride; In dichloromethane; at 0 - 23℃; for 3h;	(00ll6] 4-lodo-1,2-dimethoxybenzene (52) (Janssen, eta/., J. 01g. Chern. 20:1326-1329( 1955)): To a solution of 13b (97.6 mg, 0.272 mmol) in CH2Ch (1 mL) wa~ added a soJ·utiouofiCI (46.3 mg, 1.05 cquiv) in CI·hC12 (I rnL) at 0 C. The reaction mixture was stirred at 23oc for 3 h. The volatile materials were evaporated in vacuo, and the residue was purified byflash column chromatography on silica (0-720% ethyl acetate in hcxanes) to give the productas a colorless liquid that solidif'ied at 23 ( (67.5 mg, 94% yield). 1H NMR (600 rvmz,CDCb) il 7.20 (d, J= 8.4 Hz, 1 H), 7.10 (s, l H), 6.60 (d, J= 8.4 Hz, lH), 3.84 (s, 3H), 3.83(s. 3H). t)c NMR (151 MHz. CDCb) o 149.83 (s). 149.16 (s), 129.78 (s), 120.33 (s), 113.18(s). 82.39 (s), 56.13 (s), 55.96 (s).

Reference： [1]Science,2014,vol. 343,p. 853 - 857
[2]Patent: WO2015/35325,2015,A1 .Location in patent: Paragraph 00116

60
[ 5460-32-2 ]
[ 117402-69-4 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 402 - 405

61
[ 2033-89-8 ]
[ 5460-32-2 ]
[ 101432-12-6 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 402 - 405

62
[ 700-96-9 ]
[ 5460-32-2 ]
[ 70339-52-5 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 402 - 405

63
[ 1514-87-0 ]
[ 5460-32-2 ]
[ 1456616-05-9 ]

Yield	Reaction Conditions	Operation in experiment
55%Chromat.	With copper(l) iodide; 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosan/[18F]fluoride; N,N,N,N,-tetramethylethylenediamine; In N,N-dimethyl-formamide; acetonitrile; at 100 - 150℃; for 0.333333h;Inert atmosphere; Sealed tube;	General procedure: [18F]KF/K222 inMeCN was added to a V-vial containing CuI (11 mg) and a magnetic stirrer bar. The solvent was evaporated under N2 at 100 C (2 min). The vial was removed from heat,and a solution of methyl chlorodifluoroacetate (6 ml), TMEDA (9 ml) and aryl (or heteroaryl) iodide (0.037 mmol) in DMF (300 ml) was added via syringe. The sealed vial was heated at 150 C for 20 min. The reaction was quenched by the addition ofwater (100 ml). An aliquot was removed for analysis by radioTLC and HPLC toobtain the RCY and product identity, respectively.

Reference： [1]Nature Chemistry,2013,vol. 5,p. 941 - 944

64
[ 78-08-0 ]
[ 5460-32-2 ]
[ 6380-23-0 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 3001 - 3008

65
[ 2142-69-0 ]
[ 5460-32-2 ]
[ 1184772-51-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium tert-butylate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 80℃; for 2h;Schlenk technique; Inert atmosphere;	Compound 1 was mixed with with aryliodide 2c (132.0 mg, 0.50 mmol), ortho-bromoacetophenone 1a (109.4 mg, 0.55 mmol), Pd(OAc)2 (2.2 mg, 2 mol%), xantphos (11.6 mg, 4 mol%), tBuOK (72.9 mg, 0.65 mmol), and dry toluene (4 mL)at 80 C for 45 min. Silica-gel column chromatography (20g, petroleum ether/ethyl acetate, 85:15 to 80:20) furnished the title compound 3ac (155 mg, 92%) as yellow solid, recrystallized the solid with dichloromethane/hexane, mp 74-76 C [TLCc ontrol (petroleum ether/ethyl acetate 90:10), Rf(1a)0.55, Rf(2c)0.45, and Rf(3ac) 0.20, UV detection]. IR (MIR-ATR, 4000-600 cm1): νmax2956, 2923,2852, 1697, 1587, 1512, 1463, 1422, 1259, 1154, 1140, 1025, 791, 757, 678 cm1. 1HNMR (CDCl3, 400 MHz): d7.57 (d, 1H, J7.8 Hz, Ar-H), 7.35-7.15 (m, 3H,Ar-H), 6.78 (d, 1H, J8.7 Hz, Ar-H), 6.76 (dd, 1H, J8.7 and 1.9 Hz, Ar-H),6.74 (d, 1H. J1.9 Hz, Ar-H), 4.15 (s, 2H, ArCOCH2), 3.83 (s, 3H, ArOCH3),3.82 (s, 3H, ArOCH3) ppm. 13C NMR (CDCl3, 100 MHz): 201.8 (s, Ar-C=O),148.9 (s, Ar-C), 148.1 (s, Ar-C), 141.4 (s, Ar-C), 133.5 (d, Ar-CH), 131.4 (d, Ar-CH),128.6 (d, Ar-CH), 127.2 (d, Ar-CH), 125.8 (s, Ar-C), 121.9 (d, Ar-CH), 118.6(s, Ar-C), 112.7 (d, Ar-CH), 111.2 (d, Ar-CH), 55.8 (q, 2C, 2ArOCH3), 49.0 (t, Ar-COCH2) ppm. HR-MS (ESI) m=z calculated for [C16H7916 BrO3][MH]:335.0277; found 335.0294. [C16H8116 BrO3][MH]: 337.0259; found 337.0274.

Reference： [1]Synthetic Communications,2014,vol. 44,p. 2103 - 2111

66
[ 6342-63-8 ]
[ 5460-32-2 ]
[ 1616489-48-5 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium tert-butylate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; at 80℃; for 2h;Schlenk technique; Inert atmosphere;	General procedure: In an oven dried Schlenk tube under nitrogen atmosphere, were added aryliodides 2a-2f (0.50 mmol), ortho-bromoacetophenone 1a-1c (0.55mmol), Pd(OAc)2 (2 mol%), xantphos (4 mol%) and tBuOK (0.65 mmol) followed by addition of dry toluene (4 mL). The resulted reaction mixture was stirred at 80 C for 45 min to 3 h. Progress of the reaction was monitored by TLC till the reaction is completed. The reaction mixture was then quenched with saturated aqueous NH4Cl and the aqueous layer was extracted with ethyl acetate (3 20 mL). The combined organic layers were dried (Na2SO4) and concentrated under in vacuo. The crude product 3ac-3cf was purified by column chromatography on silica gel using petroleum ether/ethyl acetate as eluent.

Reference： [1]Synthetic Communications,2014,vol. 44,p. 2103 - 2111

67
[ 908129-33-9 ]
[ 5460-32-2 ]
(S)-N-(3-(3,4-dimethoxyphenyl)-2-phthalimidopropionyl)-8-aminoquinoline [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 13924 - 13927
[2]Angewandte Chemie - International Edition,2016,vol. 55,p. 13859 - 13862
Angew. Chem.,2016,vol. 128,p. 14063 - 14066

68
[ 6315-89-5 ]
[ 5460-32-2 ]

Yield	Reaction Conditions	Operation in experiment
74.78%		A mechanically stirred mixture of 3,4-dimethoxyaniline (5.36 g, 35 mmol) and 36 % HCl (50 mL) was cooled to -5 C. A solution of NaNO2 (2.90 g, 42 mmol) in 20 mL H2O was cooled to 0 C and slowly added while maintaining the temperature at -5 C. The final solution was stirred at 0 C for 30 min. A solution of KI (11.62 g, 70 mmol) in 30 mL H2O was added dropwise keeping the temperature between 0 and 5 C. The resulting mixture was stirred overnight and extracted twice with diethyl ether. The organic layer was consecutively washed with a concentrated NaHSO3 solution, 5 % NaOH and water and dried over MgSO4. The solvent was removed under reduced pressure and the crude product was purified by column chromatography using silica gel and dichloromethane-hexane (3:1; v/v) as the eluent to give 1, a pale yellow oil phase (6.91 g, 74.78%). 1H NMR (500 MHz, d6-DMSO, ppm): δ 7.23 (d, J = 8.38 Hz, 1H), 7.19 (s, 1H), 6.78 (d, J = 8.39 Hz, 1H), 3.75 (s, -OCH3, 3H), 3.73 (s, -OCH3, 3H).

Reference： [1]Dyes and Pigments,2015,vol. 113,p. 390 - 401
[2]Organic Letters,2017,vol. 19,p. 2518 - 2521

69
[ 5460-32-2 ]
[ 106-40-1 ]
N-(4-bromophenyl)-N-(3,4-dimethoxyphenyl)-3,4-dimethoxyaniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64.1%	With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide; In toluene; at 125℃; for 24h;Inert atmosphere;	General procedure: To a stirred solution of 4-iodoanisole (5.85 g, 25 mmol), 4-bromoaniline (1.72 g, 10 mmol), and 1,10-phenanthroline (0.18 g, 1 mmol) in toluene (100 mL) were added potassium hydroxide (5.61 g, 100 mmol) and copper(I) iodide (0.19 g, 1 mmol). The reaction mixture was heated under reflux for 24 h at 125 C. The crude product was extracted into dichloromethane, and the organic layer was washed with 1 N HCl solution, brine, and water. The organic layer was dried with anhydrous MgSO4 and then the solvent was removed in vacuo. The residue was purified by column chromatography using silica gel and dichloromethane-hexane (1:1; v/v) as the eluent to give 3 (2.39 g, 62.2%).

Reference： [1]Dyes and Pigments,2015,vol. 113,p. 390 - 401

70
[ 274-80-6 ]
[ 5460-32-2 ]
3-(3,4-dimethoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 5372 - 5375

71
[ 5460-32-2 ]
[2-(biphenyl-4-yl)-1,1,2,2-tetrafluoroethyl](trimethyl)silane [ No CAS ]
4-[2-(3,4-dimethoxyphenyl)-1,1,2,2-tetrafluoroethyl]biphenyl [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 3466 - 3469

72
[ 5460-32-2 ]
[ 65-85-0 ]
[ 1794-58-7 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 3418 - 3421

73
[ 3054-95-3 ]
[ 5460-32-2 ]
[ 58045-88-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrabutylammonium acetate; palladium diacetate; potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 4h;	To a stirred solution of <strong>[5460-32-2]1-iodo-3,4-dimethoxybenzene</strong> 8 (0.132g, 0.5mmol) in DMF (2.0mL) were added acrolein diethyl acetal (0.229mL, 1.5mmol), nBu4NOAc (0.302g, 1.0mmol), K2CO3 (0.104g, 0.75mmol), and Pd(OAc)2 (0.003g, 0.015mmol) and the mixture was stand for 4hat 90C. After that period, the mixture was cooled, hydrochloric acid 2N was slowly added and the reaction was stirred at room temperature for 10min. Then, the mixture was diluted with ethyl ether (50mL) and washed with water (3×50mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with dichloromethane as eluent to give the desired (E)-3-(3,4-dimethoxyphenyl)acrylaldehyde 9 in good yield (77mg, 80%). 4.9.1 (E)-3-(3,4-dimethoxyphenyl)acrylaldehyde (9) (0045) M.p. 80-82C. 1H NMR (300MHz, CDCl3): δ 3.93 (s, 3H, 3-OCH3), 3.94 (s, 3H, 4-OCH3), 6.62 (dd, 1H, H-α, J 15.8, 7.8Hz), 6.91 (d, 1H, H-5, J 8.3Hz), 7.08 (d, 1H, H-2, J 2.0Hz), 7.17 (dd, 1H, H-6, J 8.3, 2.0Hz), 7.42 (d, 1H, H-β, J 15.8Hz), 9.66 (d, 1H, CHO, J 7.8Hz) ppm. 13C NMR (75MHz, CDCl3): δ 55.8 and 55.9 (3,4-OCH3), 109.7 (C-2), 111.0 (C-5), 123.3 (C-6), 126.6 (C-α), 126.9 (C-1), 149.3 (C-3), 151.9 (C-4), 152.8 (C-β), 193.5 (CHO) ppm. MS m/z (ESI+, %): 193 ([M+H]+, 95), 215 ([M+Na]+, 100). HRMS (ESI+) m/z calcd. for C11H13O3 [M+H]+ 193.0859; found 193.0855.
53%	With tetrabutylammonium acetate; palladium diacetate; potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 4h;	To a solution of the appropriate 4-iodobenzene 7a,b (1.0 mmol)in DMF (10 mL) were added the following reagents through thereferred order: acrolein diethyl acetal (0.46 mL, 3.0 mmol), nBu4-NOAc (0.603 g, 2.0 mmol), K2CO3 (0.207 g, 1.5 mmol), and Pd(OAc)2 (6.7 mg, 0.03 mmol) (for 8a) or PdCl2 (5.3 mg, 0.03 mmol) (for 8b). This mixturewas stirred at 90 C for 4 h for 8a and 21 h for 8b. After this period, it was poured onto ice (50 g) and H2O (100 mL) and thepH was adjusted to 1 with diluted HCl. In the case of 8a, this aqueous solution was extracted with Et2O (3 50 mL) and theorganic layer was dried over anhydrous Na2SO4. In the case of 8b, the obtained precipitate was filtered off, taken in CH2Cl2 and driedover anhydrous Na2SO4. The solvent was evaporated to the dryness and both residues were purified by silica gel column chromatographyusing CH2Cl2 as eluent.4.1.7.1. (E)-3,4-Dimethoxycinnamaldehyde (8a). White solid(102 mg, 53% yield); Rf 0.28. Mp 80-82 C. 1H NMR (300.13 MHz,CDCl3): δ 9.66 (d, J 7.8 Hz, 1H, CHO), 7.42 (d, J 15.8 Hz, 1H, H-b), 7.17(dd, J 8.3 and 2.0 Hz, 1H, H-6), 7.08 (d, J 2.0 Hz, 1H, H-2), 6.91 (d, J8.3 Hz, 1H, H-5), 6.62 (dd, J 15.8 and 7.8 Hz, 1H, H-a), 3.94 (s, 3H, 4-OCH3), 3.93 (s, 3H, 3-OCH3) ppm. 13C NMR (75.47 MHz, CDCl3):δ 193.5 (CHO), 152.8 (C-b), 151.9 (C-4), 149.3 (C-3), 126.9 (C-1), 126.6(C-a), 123.3 (C-6), 111.0 (C-5), 109.7 (C-2), 55.9 and 55.8 (3,4-OCH3)ppm. ESI-MS m/z (%): 215 ([M+Na]+, 100), 193 ([M+H]+, 95). ESIHRMSm/z calcd for [C11H12O3H]: 193.0865, found: 193.0855.

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 115,p. 381 - 392
[2]European Journal of Medicinal Chemistry,2016,vol. 119,p. 250 - 259

74
[ 201230-82-2 ]
[ 4393-06-0 ]
[ 5460-32-2 ]
[ 67756-25-6 ]

Reference： [1]ACS Catalysis,2016,vol. 6,p. 2982 - 2987

75
[ 598-32-3 ]
[ 201230-82-2 ]
[ 5460-32-2 ]
[ 67756-23-4 ]

Reference： [1]ACS Catalysis,2016,vol. 6,p. 2982 - 2987

76
[ 5460-32-2 ]
[ 100-52-7 ]
[ 4038-14-6 ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 6409 - 6423

77
[ 275-02-5 ]
[ 5460-32-2 ]
7-(3,4-dimethoxyphenyl)-1,2,4-triazolo<1,5-a>pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With potassium phosphate; copper(l) iodide; 1,10-Phenanthroline; Trimethylacetic acid In 1,4-dioxane at 140℃; for 24h; Inert atmosphere; Schlenk technique; regioselective reaction;

Reference： [1]Wu, Jie; Cheng, Yangyang; Lan, Jingbo; Wu, Di; Qian, Shengyou; Yan, Lipeng; He, Zhen; Li, Xiaoyu; Wang, Kai; Zou, Bo; You, Jingsong [Journal of the American Chemical Society, 2016, vol. 138, # 39, p. 12803 - 12812]

78
[ 5460-32-2 ]
[ 536-74-3 ]
[ 70127-39-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; at 90℃; for 0.25h;Green chemistry;	General procedure: Arylhalide (0.80 mmol), phenyl acetylene (0.96 mmol) and KOH (1.60 mmol) was dissolved in PEG200(2.00 mL) in a reaction vial. The hybrid xerogel (the gel that was dried under high vacuum until constant weight, approx. 24 h) containing approx. 8.00 mmol of Pd (1% mol) was added to the reaction mixture. The reaction vial was heated to 90 C and left to react without stirring. The progress of the reaction was monitored by TLC. When the reaction was finished (15 min) the reaction mixture was extracted with diethyl ether (3e5 5 mL) and washed with water (3 20 mL). The organic phase was dried over MgSO4 and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography (eluent: hexaneor hexane:dichloromethane mixture) to give the desired product.

Reference： [1]Organic Letters,2016,vol. 18,p. 6196 - 6199
[2]Tetrahedron,2020,vol. 76

79
[ 4393-06-0 ]
[ 5460-32-2 ]
[ 7468-58-8 ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 12212 - 12222
[2]ACS Medicinal Chemistry Letters,2020,vol. 11,p. 2131 - 2138
[3]European Journal of Organic Chemistry,2018,vol. 2018,p. 971 - 979

80
[ 91-16-7 ]
[ 709-09-1 ]
[ 5460-32-2 ]

Yield	Reaction Conditions	Operation in experiment
17 mg; 61%	With hydrogenchloride; iodine; sodium nitrite; In 2,2,2-trifluoroethanol; water; at 20℃; for 1.0h;	General procedure: To a 25 mL round-bottom flask equipped with a magnetic stir bar was added ground iodine (127 mg, 0.5 mmol) and solvent (1.0 mL). Under agitation, this mixture was treated with hydrochloric acid (37% aqueous, 12.5 L, 0.15 mmol), sodium nitrite (40% aqueous, 6.7 L, 0.05 mmol), and the aromatic substrate (1.0 mmol). A balloon inflated with air was attached and the mixture was stirred at room temperature for 1-72 h, after which the reaction was quenched by the addition of saturated sodium thiosulfate (ca. 2 mL) and saturated sodium bicarbonate (ca. 2 mL). The mixture was partitioned between dichloromethane (ca. 15 mL) and deionized water (ca. 25 mL). The organic layer was collected, dried over sodium sulfate, and concentrated. The residue was purified by silica gel chromatography.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 645 - 648

81
[ 5460-32-2 ]
8-(Prop-1-en-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol [ No CAS ]
C₁₉H₂₆O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; at 90℃; for 12h;	A mixture of I (117.0 g, 590 mmol), <strong>[5460-32-2]4-iodo-1,2-dimethoxybenzene</strong> (85.0 g, 590 mmol), Pd(OAc)2 (13.2 g, 59 mmol) and tri(o-tolyl)phosphine (36.0 g, 118 mmol) in triethylamine (3 L) was heated at 90 C. for 12 h. The mixture was cooled to room temperature and diluted with ethyl acetate (3 L). The organic phase was washed with brine, dried (MgSO4), and concentrated in vacuo to dryness. The crude product was purified by silica gel chromatography (0 to 40% ethyl acetate/hexanes) to provide (la) as a brown oil (87.0 g, 73% based on the recovered starting material). 1H NMR (300 MHz, CDCl3): δ 6.85 (s, 2H), 6.79 (s, 1H), 6.64 (s, 1H), 3.98-3.93 (m, 4H), 3.88 (s, 3H), 3.86 (s, 3H), 2.10-2.00 (m, 4H), 1.81 (s, 3H), 1.68 (d, J=12.9 Hz, 4H), 1.17 (s, 1H)
87 g	With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; at 90℃; for 12h;	Step 1: A mixture of I (117.0 g, 590 mmol), <strong>[5460-32-2]4-iodo-1,2-dimethoxybenzene</strong> (85.0 g, 590 mmol), Pd(OAc)2 (13.2 g, 59 mmol) and tri(o-tolyl)phosphine (36.0 g, 118 mmol) in triethylamine (3 L) was heated at 90 C. for 12 h. The mixture was cooled to room temperature and diluted with ethyl acetate (3 L). The organic phase was washed with brine, dried (MgSO4), and concentrated in vacuo to dryness. The crude product was purified by silica gel chromatography (0 to 40% ethyl acetate/hexanes) to provide (1a) as a brown oil (87.0 g, 73% based on the recovered starting material). 1H NMR (300 MHz, CDCl3): δ 6.85 (s, 2H), 6.79 (s, 1H), 6.64 (s, 1H), 3.98-3.93 (m, 4H), 3.88 (s, 3H), 3.86 (s, 3H), 2.10-2.00 (m, 4H), 1.81 (s, 3H), 1.68 (d, J=12.9 Hz, 4H), 1.17 (s, 1H).

Reference： [1]Patent: US9562031,2017,B1 .Location in patent: Page/Page column 57; 59
[2]Patent: US2017/73324,2017,A1 .Location in patent: Paragraph 0091; 0092; 0093

82
[ 100-13-0 ]
[ 5460-32-2 ]
[ 51042-54-7 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrabutylammomium bromide; potassium acetate; palladium diacetate; In N,N-dimethyl-formamide; at 80℃; for 5h;Inert atmosphere; Sealed tube;	General procedure: To a solution of tetrabutylammonium bromide (1.100 g, 3.33 mmol), potassium acetate (0.586 g, 3.57 mmol), and palladium acetate (0.025 g, 0.11 mmol) in DMF (20 mL) were added substituted iodobenzene (2.21 mmol) and 4-nitrostyrene (2.44 mmol). The reaction mixture was recharged with argon and stirred at 80C for 5 h in a sealed tube. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl and concentrated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 10:3) to afford the intermediate substituted (E)-1-nitro-4-styrylbenzene. To a solution of stannous chloride (2.087 g, 11.05 mmol) in EtOH (20 mL) was added substituted (E)-1-nitro-4-styrylbenzene (2.21 mmol). The reaction mixture was stirred at reflux temperaturefor 4.0 h. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl and concentrated in vacuo. The residue was purified by column chromatography on silica gel (dichloromethane/methanol, 10:0.1) to afford pure product.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 136,p. 382 - 392

83
[ 1073-67-2 ]
[ 5460-32-2 ]
[ 52792-14-0 ]

Yield	Reaction Conditions	Operation in experiment
89.5%	With tetrabutylammomium bromide; potassium acetate; palladium diacetate; In N,N-dimethyl-formamide; at 80℃; for 5h;Inert atmosphere; Sealed tube;	General procedure: To a solution of tetrabutylammonium bromide (1.100 g, 3.33mmol), potassium acetate (0.586 g, 3.57 mmol), and palladium acetate (0.025 g, 0.11mmol) in DMF (20 mL) were added substituted iodobenzene (2.21mmol) and substituted styrene (2.44 mmol). The reaction mixture was recharged with argon and stirred at 80C for 5 h in a sealed tube. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl and concentrated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 10:3) to afford pure product.(E)-4-(4-Chlorostyryl)-1,2-dimethoxybenzene(1).4-Chlorostyrene reacted with 3,4-dimethoxy-iodobenzene following the general procedure (Scheme S1) to give the desired product1(Yield 89.5%Purity 96.6%, CAS: 52792-14-0) as a white amorphous solid.HRMS (ESI) (M+Na)+m/z297.06579, calcd for C16H15ClNaO2297.06528.1H NMR (CDCl3, 500 MHz) δ: 7.35 (d,J= 8.5 Hz, 2H), 7.26 (d,J= 8.5 Hz, 2H), 6.92-7.00 (m, 3H), 6.86 (d,J= 16.0 Hz, 1H), 6.80 (d,J= 8.0 Hz, 1H), 3.90 (s, 3H), 3.85 (s, 3H).13C NMR (CDCl3, 125 MHz) δ: 149.0, 135.9, 132.6, 129.9, 129.0, 128.7, 127.2, 125.2, 119.9, 111.2, 108.8, 55.7.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 136,p. 382 - 392

84
[ 2628-16-2 ]
[ 5460-32-2 ]
[ 880354-47-2 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrabutylammomium bromide; potassium acetate; palladium diacetate; In N,N-dimethyl-formamide; at 80℃; for 5h;Inert atmosphere; Sealed tube;	General procedure: To a solution of tetrabutylammonium bromide (1.100 g, 3.33 mmol), potassium acetate (0.586 g, 3.57 mmol), and palladium acetate (0.025 g, 0.11 mmol) in DMF (20 mL) were added substituted iodobenzene (2.21 mmol) and 4-acetyloxystyrene (2.44 mmol). The reaction mixture was recharged with Argon and stirred at 80C for 5 h in a sealed tube. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl and concentrated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 10:3) to afford the intermediate substituted (E)-4-styrylphenyl acetate. To a solution of triethylamine (2.0 mL) in MeOH (5 mL) was added substituted (E)-4-styrylphenyl acetate (1.36 mmol). The reaction mixture was stirred at reflux temperaturefor 3 h. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl and concentrated in vacuo. The residue was purified by column chromatography on silica gel (dichloromethane/methanol, 10:0.3) to afford pure product.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 136,p. 382 - 392

85
Phe-Wang resin [ No CAS ]
[ 5460-32-2 ]
[ 18414-58-9 ]
[ 169887-39-2 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 2873 - 2876

86
[ 5460-32-2 ]
[ 135884-31-0 ]
2-(3,4-dimethoxyphenyl)-1H-pyrrole [ No CAS ]
C₁₇H₂₁NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; bis(dibenzylideneacetone)-palladium(0); CyJohnPhos; In ethanol; water;Inert atmosphere; Reflux;	4-Iodo-1,2-dimethoxybenzene (5; 16.7 g, 63.3 mmol) was dissolved in EtOH (63 mL), Boc-pyrroleboronic acid (4; 20.0 g, 94.8 mmol, 1.5 equiv) was added to the solution followed by the addition of an aqueous solution of K2CO3 (17.5 g, 126.8 mmol, 2 equiv; in 63 mL H2O). Under a constant flow of N2, CyJohnPhos (378 mg, 2 mol%) was added followed by Pd(dba)2 (364 mg, 1 mol%). The reaction mixture was vigorously stirred and heated under reflux for 4-5 h. The reaction mixture was cooled to r.t. and extracted with hexane (3 x 100 mL). The organic layer was dried over Na2SO4 and evaporated. To the residue (contains aryl iodide, Boc-pyrrole and product ~1:1:1) was added freshly prepared (from Na and MeOH) NaOMe solution (~1 M in MeOH, 3-5 equiv) and the mixture was left overnight. The reaction mixture was diluted with H2O and extracted with Et2O (3 x 100 mL). The organic layer was washed with brine, dried over Na2SO4, filtered, and evaporated. The residue was triturated with hexane and filtered off to give pure enough compound.

Reference： [1]Synthesis,2017,vol. 49,p. 3692 - 3699

87
calcium carbide [ No CAS ]
[ 5460-32-2 ]
[ 4302-52-7 ]
[ 79238-81-6 ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 6800 - 6807

88
[ 1066-35-9 ]
[ 5460-32-2 ]
(6-iodo-2,3-dimethoxyphenyl)dimethylsilane [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 4247 - 4250

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P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
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

[ CAS No. 5460-32-2 ] {[proInfo.proName]}

Quality Control of [ 5460-32-2 ]

Related Doc. of [ 5460-32-2 ]

Product Details of [ 5460-32-2 ]

Calculated chemistry of [ 5460-32-2 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 5460-32-2 ]

[ 5460-32-2 ] Synthesis Path-Upstream 1~1

[ 5460-32-2 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 5460-32-2 ]

Aryls

Ethers

Precautionary Statements-General

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Physical hazards

Health hazards

Environmental hazards

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[ 5460-32-2 ]