[ CAS No. 2065-27-2 ]

Name: 2065-27-2|Methyl 2,6-dimethoxybenzoate|95%
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Quality Control of [ 2065-27-2 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 2065-27-2 ]

CAS No. :	2065-27-2	MDL No. :	MFCD00075861
Formula :	C₁₀H₁₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XLXVNKPXOIYLLE-UHFFFAOYSA-N
M.W :	196.20	Pubchem ID :	137419
Synonyms :

Safety of [ 2065-27-2 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2065-27-2 ]

* 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 [ 2065-27-2 ]
Downstream synthetic route of [ 2065-27-2 ]

[ 2065-27-2 ] Synthesis Path-Upstream 1~3

1
[ 2065-27-2 ]
[ 3147-64-6 ]

Reference： [1] European Journal of Medicinal Chemistry, 1986, vol. 21, # 5, p. 379 - 383

2
[ 2065-27-2 ]
[ 22833-69-8 ]

Reference： [1] Tetrahedron Letters, 2019, vol. 60, # 1, p. 52 - 54
[2] Tetrahedron, 2002, vol. 58, # 25, p. 5023 - 5038

3
[ 2065-27-2 ]
[ 2734-70-5 ]

Reference： [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 38, p. 9046 - 9054

[ 2065-27-2 ] Synthesis Path-Downstream 1~69

1
[ 67-56-1 ]
[ 1466-76-8 ]
[ 2065-27-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sulfuric acid for 18h; Reflux;
92%	With sulfuric acid at 0℃; for 16h; Reflux;
77%	With di(methoxycarbonyl)methylene tri-n-butylphosphorane In toluene at 70℃; for 24h;

77%	In toluene
65%	With sulfuric acid at 70℃; for 2h;
	With hydrogenchloride
	Stage #1: 2-6-dimethoxybenzoic acid With oxalyl dichloride In N,N-dimethyl-formamide for 1h; Heating; Stage #2: methanol With triethylamine at 20℃; for 0.166667h; Further stages.;

Reference： [1]Moghaddam, Firouz Matloubi; Farimani, Mahdi Moridi [Tetrahedron Letters, 2010, vol. 51, # 3, p. 540 - 542]
[2]Arndt, Hans-Dieter; Nasufovic, Veselin; Sauer, Maria; Vilotijevic, Ivan [Organic and biomolecular chemistry, 2020, vol. 18, # 8, p. 1567 - 1571]
[3]McNulty, James; Capretta, Alfredo; Laritchev, Vladimir; Dyck, Jeff; Robertson, Al J. [Journal of Organic Chemistry, 2003, vol. 68, # 4, p. 1597 - 1600]
[4]Current Patent Assignee: SOLVAY; ROBERTSON ALLEN JAMES (inventor) - WO2004/778, 2003, A1 Location in patent: Page 23-24
[5]Hayrapetyan, Davit; Rit, Raja K.; Kratz, Markus; Tschulik, Kristina; Gooßen, Lukas J. [Chemistry - A European Journal, 2018, vol. 24, # 44, p. 11288 - 11291]
[6]Mauthner [Journal fur praktische Chemie (Leipzig 1954), 1929, vol. <2> 121, p. 262][Journal fuer Praktische Chemie (Leipzig), 1929, vol. <2> 124, p. 320]
[7]Hayashi, Yujiro; Sekizawa, Hiromi; Yamaguchi, Junichiro; Gotoh, Hiroaki [Journal of Organic Chemistry, 2007, vol. 72, # 17, p. 6493 - 6499]

2
[ 3147-64-6 ]
[ 77-78-1 ]
[ 2065-27-2 ]

Reference： [1]Journal of the Chemical Society,1915,vol. 107,p. 841

3
[ 186581-53-3 ]
[ 124-38-9 ]
[ 79128-08-8 ]
[ 2150-41-6 ]
[ 2065-27-2 ]

Reference： [1]Gazzetta Chimica Italiana,1981,vol. 111,p. 123 - 128

4
[ 5162-44-7 ]
[ 2065-27-2 ]
[ 82939-67-1 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium; <i>tert</i>-butyl alcohol 1.) THF, ammonia, -78 deg C, 15 min; 2.) THF, -33 deg C; Yield given. Multistep reaction;

Reference： [1]Schultz,A.G.; Plummer,M.; Taveras,A.G. [Journal of the American Chemical Society, 1988, vol. 110, p. 5547]

5
[ 917-64-6 ]
[ 2065-27-2 ]
[ 16929-70-7 ]

Yield	Reaction Conditions	Operation in experiment
94%	In diethyl ether for 0.166667h; Heating;

Reference： [1]Burnell, Robert H.; Caron, Stephane [Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1446 - 1454]

6
[ 2065-27-2 ]
[ 16700-55-3 ]

Reference： [1]Chemistry Letters,1990,p. 389 - 392

7
[ 2065-27-2 ]
[ 3147-64-6 ]

Reference： [1]European Journal of Medicinal Chemistry,1986,vol. 21,p. 379 - 383

8
[ 1466-76-8 ]
[ 77-78-1 ]
[ 2065-27-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium carbonate In acetone for 23h; Heating;

Reference： [1]Tsuchida, Eishun; Hasegawa, Etsuo; Komatsu, Teruyuki; Nakata, Taisaku; Nishide, Hiroyuki [Chemistry Letters, 1990, # 3, p. 389 - 392]

9
[ 2065-27-2 ]
[ 74-88-4 ]
[ 82478-17-9 ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: methyl 2,6-dimethoxybenzoate With potassium In tetrahydrofuran; ammonia; <i>tert</i>-butyl alcohol Stage #2: methyl iodide Further stages.;
	With ammonia; <i>tert</i>-butyl alcohol 1) THF, -78 deg C, 2) -78 deg C; Multistep reaction;
	With penta-1,3-diene; potassium <i>tert</i>-butylate; ammonia; potassium 1.) THF, t-butyl alcohol, -70 deg C 2.) THF; Yield given. Multistep reaction;

Reference： [1]Elliott, Mark C.; Gist, Matthew J.; Binns, Falmai; Jones, Richard G. [Tetrahedron Letters, 2004, vol. 45, # 14, p. 2899 - 2901]
[2]Schultz, Arthur G.; Dittami, James P.; Lavieri, Frank P.; Salowey, Christina; Sundararaman, Padmanabhan; Szymula, Mary Beth [Journal of Organic Chemistry, 1984, vol. 49, # 23, p. 4429 - 4440]
[3]Hook, James M.; Mander, Lewis N.; Woolias, Michael [Tetrahedron Letters, 1982, vol. 23, # 10, p. 1095 - 1098]

10
[ 624-75-9 ]
[ 2065-27-2 ]
[ 182363-75-3 ]

Yield	Reaction Conditions	Operation in experiment
37%	With ammonia In <i>tert</i>-butyl alcohol at -78℃;

Reference： [1]Schultz, Arthur G.; Taveras, Arthur G. [Tetrahedron Letters, 1996, vol. 37, # 33, p. 5853 - 5856]

11
[ 1466-76-8 ]
[ 616-38-6 ]
[ 2065-27-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With 1,8-diazabicyclo[5.4.0]undec-7-ene for 4h; Heating;
98%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 160℃; for 0.2h; microwave irradiation;

Reference： [1]Shieh, Wen-Chung; Dell, Steven; Repic, Oljan [Journal of Organic Chemistry, 2002, vol. 67, # 7, p. 2188 - 2191]
[2]Shieh, Wen-Chung; Dell, Steven; Repič, Oljan [Tetrahedron Letters, 2002, vol. 43, # 32, p. 5607 - 5609]

12
[ 2065-27-2 ]
[ 22833-69-8 ]

Reference： [1]Tetrahedron Letters,2019,vol. 60,p. 52 - 54
[2]Tetrahedron,2002,vol. 58,p. 5023 - 5038

13
[ 91-63-4 ]
[ 2065-27-2 ]
2-(2'-quinolino)-2,6-dimethoxy-acetophenone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	Stage #1: 2-methylquinoline With n-butyllithium In diethyl ether; hexane at -10℃; for 2h; Stage #2: methyl 2,6-dimethoxybenzoate In diethyl ether; hexane at 20℃; for 20h;

Reference： [1]Sepac, Dragan; Roje, Marin; Hamersak, Zdenko; Sunjic, Vitomir [Croatica Chemica Acta, 2003, vol. 76, # 3, p. 235 - 239]

14
[ 1445-45-0 ]
[ 1466-76-8 ]
[ 2065-27-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	In various solvent(s) at 80℃; for 2h;

Reference： [1]Yoshino, Tomonori; Imori, Satomi; Togo, Hideo [Tetrahedron, 2006, vol. 62, # 6, p. 1309 - 1317]

15
[ 2065-27-2 ]
[ 106-95-6 ]
[ 185385-63-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: methyl 2,6-dimethoxybenzoate With ammonia; sodium In diethyl ether; <i>tert</i>-butyl alcohol Stage #2: allyl bromide In diethyl ether; <i>tert</i>-butyl alcohol at -78 - 20℃; for 11h; Further stages.;
	Stage #1: methyl 2,6-dimethoxybenzoate With ammonia; sodium; <i>tert</i>-butyl alcohol In diethyl ether at -78℃; for 0.5h; Inert atmosphere; Stage #2: allyl bromide In diethyl ether
	With ammonia; sodium In diethyl ether; <i>tert</i>-butyl alcohol at -78℃; Inert atmosphere;

Reference： [1]Abe, Masahito; Nakada, Masahisa [Tetrahedron Letters, 2007, vol. 48, # 28, p. 4873 - 4877]
[2]Location in patent: experimental part Uwamori, Masahiro; Saito, Aya; Nakada, Masahisa [Journal of Organic Chemistry, 2012, vol. 77, # 11, p. 5098 - 5107]
[3]Uwamori, Masahiro; Nakada, Masahisa [Journal of Antibiotics, 2013, vol. 66, # 3, p. 141 - 145]

16
[ 31608-22-7 ]
[ 2065-27-2 ]
[ 949587-21-7 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 6493 - 6499

17
[ 2065-27-2 ]
[ 147666-84-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: BCl₃ / CH₂Cl₂ / 21.5 h / 0 °C 1.2: 90 percent / Solvolysis 2.1: NaH / dimethylformamide / 3.67 h / 0 - 20 °C 3.1: Grignard reagent 3.2: ZnCl₂ / tetrahydrofuran / 0.33 h / 0 °C 3.3: Pd₂(dba)3; 1,1'-bis(diphenylphosphino)ferrocene / tetrahydrofuran / 4.5 h / 60 °C 4.1: 4 percent / iodine / acetonitrile / 1.5 h / 52 - 57 °C
	Multi-step reaction with 5 steps 1.1: BCl₃ / CH₂Cl₂ / 21.5 h / 0 °C 1.2: 90 percent / Solvolysis 2.1: NaH / dimethylformamide / 3.67 h / 0 - 20 °C 3.1: Grignard reagent 3.2: ZnCl₂ / tetrahydrofuran / 0.33 h / 0 °C 3.3: Pd₂(dba)3; 1,1'-bis(diphenylphosphino)ferrocene / tetrahydrofuran / 4.5 h / 60 °C 4.1: 24 percent / iodine / acetonitrile / 1.5 h / 52 - 57 °C 5.1: 93 percent / Et₃N; PPh₃; 99 percent formic acid / Pd(OAc)2 / dimethylformamide / 5 h / 60 °C
	Multi-step reaction with 5 steps 1.1: BCl₃ / CH₂Cl₂ / 21.5 h / 0 °C 1.2: 90 percent / Solvolysis 2.1: NaH / dimethylformamide / 3.67 h / 0 - 20 °C 3.1: Grignard reagent 3.2: ZnCl₂ / tetrahydrofuran / 0.33 h / 0 °C 3.3: Pd₂(dba)3; 1,1'-bis(diphenylphosphino)ferrocene / tetrahydrofuran / 4.5 h / 60 °C 4.1: 89 percent / iodine / acetonitrile / 3 h / 20 °C 5.1: 93 percent / Et₃N; PPh₃; 99 percent formic acid / Pd(OAc)2 / dimethylformamide / 5 h / 60 °C

Reference： [1]Biagetti, Matteo; Bellina, Fabio; Carpita, Adriano; Stabile, Paolo; Rossi, Renzo [Tetrahedron, 2002, vol. 58, # 25, p. 5023 - 5038]
[2]Biagetti, Matteo; Bellina, Fabio; Carpita, Adriano; Stabile, Paolo; Rossi, Renzo [Tetrahedron, 2002, vol. 58, # 25, p. 5023 - 5038]
[3]Biagetti, Matteo; Bellina, Fabio; Carpita, Adriano; Stabile, Paolo; Rossi, Renzo [Tetrahedron, 2002, vol. 58, # 25, p. 5023 - 5038]

18
[ 2065-27-2 ]
[ 60241-78-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H₂ / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: m-CPBA / CH₂Cl₂ / Ambient temperature 5: 88 percent / K₂CO₃ / acetone / 120 h / Heating

Reference： [1]Burnell, Robert H.; Caron, Stephane [Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1446 - 1454]

19
[ 2065-27-2 ]
[ 16700-61-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H₂ / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr

Reference： [1]Burnell, Robert H.; Caron, Stephane [Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1446 - 1454]

20
[ 2065-27-2 ]
[ 144707-39-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H₂ / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: m-CPBA / CH₂Cl₂ / Ambient temperature

Reference： [1]Burnell, Robert H.; Caron, Stephane [Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1446 - 1454]

21
[ 2065-27-2 ]
[ 144707-44-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H₂ / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: KBr, 18-crown-6, m-CPBA / CH₂Cl₂ / 0.5 h / 0 °C

Reference： [1]Burnell, Robert H.; Caron, Stephane [Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1446 - 1454]

22
[ 2065-27-2 ]
[ 144707-47-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H₂ / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: KBr, 18-crown-6, m-CPBA / CH₂Cl₂ / 0.5 h / 0 °C 5: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 6: NaBH₄ / methanol / 0.2 h / 0 °C 7: 87 percent / PBr₃, pyridine / benzene / 3 h

Reference： [1]Burnell, Robert H.; Caron, Stephane [Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1446 - 1454]

23
[ 2065-27-2 ]
[ 144707-46-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H₂ / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: KBr, 18-crown-6, m-CPBA / CH₂Cl₂ / 0.5 h / 0 °C 5: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 6: NaBH₄ / methanol / 0.2 h / 0 °C

Reference： [1]Burnell, Robert H.; Caron, Stephane [Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1446 - 1454]

24
[ 2065-27-2 ]
[ 144707-45-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H₂ / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: KBr, 18-crown-6, m-CPBA / CH₂Cl₂ / 0.5 h / 0 °C 5: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min

Reference： [1]Burnell, Robert H.; Caron, Stephane [Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1446 - 1454]

25
[ 2065-27-2 ]
[ 144707-49-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H₂ / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: KBr, 18-crown-6, m-CPBA / CH₂Cl₂ / 0.5 h / 0 °C 5: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 6: NaBH₄ / methanol / 0.2 h / 0 °C 7: 87 percent / PBr₃, pyridine / benzene / 3 h 8: 77 percent / 18-crown-6 / acetonitrile / 1 h / 60 °C

Reference： [1]Burnell, Robert H.; Caron, Stephane [Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1446 - 1454]

26
[ 2065-27-2 ]
[ 144707-40-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H₂ / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: m-CPBA / CH₂Cl₂ / Ambient temperature 5: 88 percent / K₂CO₃ / acetone / 120 h / Heating 6: 88 percent / KBr, 18-crown-6, m-CPBA / CH₂Cl₂ / 0.5 h

Reference： [1]Burnell, Robert H.; Caron, Stephane [Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1446 - 1454]

27
[ 2065-27-2 ]
[ 144707-42-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H₂ / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: m-CPBA / CH₂Cl₂ / Ambient temperature 5: 88 percent / K₂CO₃ / acetone / 120 h / Heating 6: 88 percent / KBr, 18-crown-6, m-CPBA / CH₂Cl₂ / 0.5 h 7: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 8: 100 percent / NaBH₄ / methanol / 0.25 h / 0 °C

Reference： [1]Burnell, Robert H.; Caron, Stephane [Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1446 - 1454]

28
[ 2065-27-2 ]
[ 144707-43-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H₂ / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: m-CPBA / CH₂Cl₂ / Ambient temperature 5: 88 percent / K₂CO₃ / acetone / 120 h / Heating 6: 88 percent / KBr, 18-crown-6, m-CPBA / CH₂Cl₂ / 0.5 h 7: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 8: 100 percent / NaBH₄ / methanol / 0.25 h / 0 °C 9: 96 percent / PBr₃, pyridine / benzene / 3 h

Reference： [1]Burnell, Robert H.; Caron, Stephane [Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1446 - 1454]

29
[ 2065-27-2 ]
[ 144707-41-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H₂ / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: m-CPBA / CH₂Cl₂ / Ambient temperature 5: 88 percent / K₂CO₃ / acetone / 120 h / Heating 6: 88 percent / KBr, 18-crown-6, m-CPBA / CH₂Cl₂ / 0.5 h 7: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min

Reference： [1]Burnell, Robert H.; Caron, Stephane [Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1446 - 1454]

30
[ 2065-27-2 ]
[ 144707-48-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H₂ / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: m-CPBA / CH₂Cl₂ / Ambient temperature 5: 88 percent / K₂CO₃ / acetone / 120 h / Heating 6: 88 percent / KBr, 18-crown-6, m-CPBA / CH₂Cl₂ / 0.5 h 7: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 8: 100 percent / NaBH₄ / methanol / 0.25 h / 0 °C 9: 96 percent / PBr₃, pyridine / benzene / 3 h 10: 91 percent / 18-crown-6 / acetonitrile / 1 h / 60 °C

Reference： [1]Burnell, Robert H.; Caron, Stephane [Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1446 - 1454]

31
[ 2065-27-2 ]
[ 144707-38-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 14 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H₂ / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: KBr, 18-crown-6, m-CPBA / CH₂Cl₂ / 0.5 h / 0 °C 5: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 6: NaBH₄ / methanol / 0.2 h / 0 °C 7: 87 percent / PBr₃, pyridine / benzene / 3 h 8: 77 percent / 18-crown-6 / acetonitrile / 1 h / 60 °C 9: 1) LDA / 1) THF, hexane, -78 deg C, 5 min, 2) -78 deg C -> rt, 3 h 10: 41 percent / BF₃ / nitromethane / 2 h / -30 °C 12: 91 percent / m-CPBA / CH₂Cl₂ / 1 h / -78 °C 13: 82 percent / pyridine / CH₂Cl₂ / 5 h / Ambient temperature 14: 1) TiCl₄, glacial acetic acid, 2) H₂O / 1) 20 min, 2) reflux, 1 h

Reference： [1]Burnell, Robert H.; Caron, Stephane [Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1446 - 1454]

32
[ 2065-27-2 ]
[ 144707-53-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H₂ / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: KBr, 18-crown-6, m-CPBA / CH₂Cl₂ / 0.5 h / 0 °C 5: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 6: NaBH₄ / methanol / 0.2 h / 0 °C 7: 87 percent / PBr₃, pyridine / benzene / 3 h 8: 77 percent / 18-crown-6 / acetonitrile / 1 h / 60 °C 9: 1) LDA / 1) THF, hexane, -78 deg C, 5 min, 2) -78 deg C -> rt, 3 h

Reference： [1]Burnell, Robert H.; Caron, Stephane [Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1446 - 1454]

33
[ 2065-27-2 ]
[ 144707-52-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 11 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H₂ / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: m-CPBA / CH₂Cl₂ / Ambient temperature 5: 88 percent / K₂CO₃ / acetone / 120 h / Heating 6: 88 percent / KBr, 18-crown-6, m-CPBA / CH₂Cl₂ / 0.5 h 7: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 8: 100 percent / NaBH₄ / methanol / 0.25 h / 0 °C 9: 96 percent / PBr₃, pyridine / benzene / 3 h 10: 91 percent / 18-crown-6 / acetonitrile / 1 h / 60 °C 11: 1) LDA / 1) THF, hexane, -78 deg C, 5 min, 2) -78 deg C -> rt, 3 h

Reference： [1]Burnell, Robert H.; Caron, Stephane [Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1446 - 1454]

34
[ 2065-27-2 ]
[ 144707-33-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 11 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H₂ / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: KBr, 18-crown-6, m-CPBA / CH₂Cl₂ / 0.5 h / 0 °C 5: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 6: NaBH₄ / methanol / 0.2 h / 0 °C 7: 87 percent / PBr₃, pyridine / benzene / 3 h 8: 77 percent / 18-crown-6 / acetonitrile / 1 h / 60 °C 9: 1) LDA / 1) THF, hexane, -78 deg C, 5 min, 2) -78 deg C -> rt, 3 h 10: 41 percent / BF₃ / nitromethane / 2 h / -30 °C

Reference： [1]Burnell, Robert H.; Caron, Stephane [Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1446 - 1454]

35
[ 2065-27-2 ]
[ 144707-35-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 12 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H₂ / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: KBr, 18-crown-6, m-CPBA / CH₂Cl₂ / 0.5 h / 0 °C 5: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 6: NaBH₄ / methanol / 0.2 h / 0 °C 7: 87 percent / PBr₃, pyridine / benzene / 3 h 8: 77 percent / 18-crown-6 / acetonitrile / 1 h / 60 °C 9: 1) LDA / 1) THF, hexane, -78 deg C, 5 min, 2) -78 deg C -> rt, 3 h 10: 41 percent / BF₃ / nitromethane / 2 h / -30 °C 12: 91 percent / m-CPBA / CH₂Cl₂ / 1 h / -78 °C

Reference： [1]Burnell, Robert H.; Caron, Stephane [Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1446 - 1454]

36
[ 2065-27-2 ]
7-Cyano-3-phenylthio-12,14-dimethoxyabieta-8,11,13-triene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H₂ / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: KBr, 18-crown-6, m-CPBA / CH₂Cl₂ / 0.5 h / 0 °C 5: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 6: NaBH₄ / methanol / 0.2 h / 0 °C 7: 87 percent / PBr₃, pyridine / benzene / 3 h 8: 77 percent / 18-crown-6 / acetonitrile / 1 h / 60 °C 9: 1) LDA / 1) THF, hexane, -78 deg C, 5 min, 2) -78 deg C -> rt, 3 h 10: 41 percent / BF₃ / nitromethane / 2 h / -30 °C

Reference： [1]Burnell, Robert H.; Caron, Stephane [Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1446 - 1454]

37
[ 2065-27-2 ]
[ 144707-54-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 13 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H₂ / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: KBr, 18-crown-6, m-CPBA / CH₂Cl₂ / 0.5 h / 0 °C 5: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 6: NaBH₄ / methanol / 0.2 h / 0 °C 7: 87 percent / PBr₃, pyridine / benzene / 3 h 8: 77 percent / 18-crown-6 / acetonitrile / 1 h / 60 °C 9: 1) LDA / 1) THF, hexane, -78 deg C, 5 min, 2) -78 deg C -> rt, 3 h 10: 41 percent / BF₃ / nitromethane / 2 h / -30 °C 12: 91 percent / m-CPBA / CH₂Cl₂ / 1 h / -78 °C 13: 82 percent / pyridine / CH₂Cl₂ / 5 h / Ambient temperature

Reference： [1]Burnell, Robert H.; Caron, Stephane [Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1446 - 1454]

38
[ 2065-27-2 ]
[ 35030-99-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 35 percent / NaBH₄, I₂ / CHCl₃ / 18 h 2: 58 percent / H₂SO₄ (d = 1.84) / 100 h / Heating

Reference： [1]Lamotte; Demerseman; Royer; et al. [European Journal of Medicinal Chemistry, 1986, vol. 21, # 5, p. 379 - 383]

39
[ 2065-27-2 ]
[ 109142-76-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 35 percent / NaBH₄, I₂ / CHCl₃ / 18 h 2: 58 percent / H₂SO₄ (d = 1.84) / 100 h / Heating 3: 100 percent / K₂CO₃ / acetone / 8 h / Heating 4: 73 percent / NaOMe / benzene / 6 h / 10 °C 5: 100 percent / K₂CO₃ / acetone / 6 h / Heating 6: 90 percent / 0.25N aq. Na₂CO₃ / 1 h / Heating 7: 94 percent / Cu, pyridine / bis-(2-hydroxy-ethyl) ether / 0.33 h / 160 °C

Reference： [1]Lamotte; Demerseman; Royer; et al. [European Journal of Medicinal Chemistry, 1986, vol. 21, # 5, p. 379 - 383]

40
[ 2065-27-2 ]
[ 109142-73-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 35 percent / NaBH₄, I₂ / CHCl₃ / 18 h 2: 58 percent / H₂SO₄ (d = 1.84) / 100 h / Heating 3: 100 percent / K₂CO₃ / acetone / 8 h / Heating 4: 73 percent / NaOMe / benzene / 6 h / 10 °C

Reference： [1]Lamotte; Demerseman; Royer; et al. [European Journal of Medicinal Chemistry, 1986, vol. 21, # 5, p. 379 - 383]

41
[ 16932-49-3 ]
[ 2065-27-2 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1929,vol. <2> 121,p. 262
Journal fuer Praktische Chemie (Leipzig),1929,vol. <2> 124,p. 320
[2]Journal fur praktische Chemie (Leipzig 1954),1929,vol. <2> 121,p. 262
Journal fuer Praktische Chemie (Leipzig),1929,vol. <2> 124,p. 320

42
[ 1466-76-8 ]
[ 2065-27-2 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile	1 Preparation of Methyl 2,6-dimethoxybenzoate EXAMPLE 1 Preparation of Methyl 2,6-dimethoxybenzoate A solution containing 2,6-dimethoxybenzoic acid (5.0 g, 27.5 mmol), DBU (4.2 g, 27.5 mmol), DMC (50 mL), and acetonitrile (50 mL) was circulated at 20 mL/min by a pump through a Milestone ETHOS-CFR continuous-flow reactor, which had been preheated to 160° C. at 20 bar by microwave irradiation. The reaction mixture was analyzed by HPLC after each cycle (6 minutes microwave irradiation). The yield of methyl 2,6-dimethoxybenzoate after two cycles (12 minutes microwave irradiation time) as determined by HPLC was 99% conversion. The reaction mixture was concentrated under vacuum. The residue was diluted with EtOAc (100 mL) and H2O (80 mL).
	With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile	1 Preparation of methyl 2,6-dimethoxybenzoate EXAMPLE 1 Preparation of methyl 2,6-dimethoxybenzoate A solution containing 2,6-dimethoxybenzoic acid (5.0 g, 27.5 mmol), DBU (4.2 g, 27.5 mmol), DMC (50 mL), and acetonitrile (50 mL) was circulated at 20 mL/min by a pump through a Milestone ETHOS-CFR continuous-flow reactor, which had been preheated to 160° C. at 20 bar by microwave irradiation. The reaction mixture was analyzed by HPLC after each cycle (6 minutes microwave irradiation). The yield of methyl 2,6-dimethoxybenzoate after two cycles (12 minutes microwave irradiation time) as determined by HPLC was 99% conversion. The reaction mixture was concentrated under vacuum. The residue was diluted with EtOAc (100 mL) and H2O (80 mL).

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US2003/144543, 2003, A1
[2]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US6653503, 2003, B2

43
1,8-Diazabicyclo[5.4.0]undec-7-ene [DBU] [ No CAS ]
[ 1466-76-8 ]
[ 144-55-8 ]
[ 2065-27-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In dimethyl carbonate (DMC); water	1 Preparation of methyl 2,6-dimethoxybenzoate using DBU catalyst EXAMPLE 1 Preparation of methyl 2,6-dimethoxybenzoate using DBU catalyst 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), (836 mg, 5.49 mmol), was added to a mixture of 2,6-dimethoxybenzoic acid (1), (1.0 g, 5.49 mmol), in dimethyl carbonate (DMC) (10 mL) and the resulting mixture was heated to reflux at 90° C. for 4 hours. The reaction mixture was cooled to 25° C. and diluted with EtOAc (30 mL) and water (30 mL). The organic layer was separated and washed in sequence with 10 mL of water, 2 M HCl (230 mL), saturated aqueous NaHCO3 (230 mL) and water (2*25 mL). The organic layer was dried over Na2SO4, filtered and concentrated under vacuum to give methyl 2,6-dimethoxybenzoate (2) as a white solid. The yield of the 2,6-dimethoxybenzoate as determined by HPLC was 97-98% conversion.

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US6515167, 2003, B1

44
[ 2065-27-2 ]
[ 756-79-6 ]
[ 1132817-98-1 ]

Yield	Reaction Conditions	Operation in experiment
72%	With lithium hexamethyldisilazane In tetrahydrofuran Cooling with ice; Inert atmosphere;

Reference： [1]Milburn, Robert R.; McRae, Ken; Chan, Johann; Tedrow, Jason; Larsen, Robert; Faul, Margaret [Tetrahedron Letters, 2009, vol. 50, # 8, p. 870 - 872]

45
[ 67-56-1 ]
[ 201230-82-2 ]
[ 23112-96-1 ]
[ 2065-27-2 ]
[ 151-10-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 58% 2: 7%	With palladium diacetate; triphenylphosphine; p-benzoquinone at 20℃; for 5h;

Reference： [1]Location in patent: scheme or table Yamamoto, Yoshihiko [Advanced Synthesis and Catalysis, 2010, vol. 352, # 2-3, p. 478 - 492]

46
[ 2065-27-2 ]
[ 74-88-4 ]
[ 16929-70-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: methyl iodide With magnesium In diethyl ether at 20℃; for 1h; Stage #2: methyl 2,6-dimethoxybenzoate In tetrahydrofuran; diethyl ether for 2h; Reflux;

Reference： [1]Moghaddam, Firouz Matloubi; Farimani, Mahdi Moridi [Tetrahedron Letters, 2010, vol. 51, # 3, p. 540 - 542]

47
[ 67-56-1 ]
[ 33513-42-7 ]
[ 151-10-0 ]
[ 2065-27-2 ]
[ 3392-97-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 13% 2: 63%	Stage #1: 1,3-Dimethoxybenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Stage #3: methanol Further stages;	4.3. Typical procedure for one-pot conversion of aromatic bromides into aromatic methyl esters with DMF General procedure: n-BuLi (1.67 M solution in hexane, 1.3 mL, 2.2 mmol) was added dropwise into a solution of p-bromoanisole (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, DMF (0.22 mL, 2.2 mmol) was added to the mixture and the obtained mixture was stirred at rt. After 2 h at the same temperature, THF was removed. Then, MeOH (3 mL) was added to the residue and the mixture was stirred at room temperature. After 30 min, I2 (1523 mg, 6 mmol) and K2CO3 (829 mg, 6 mmol) were added at 0 °C and the obtained mixture was stirred for 22 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3×20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide methyl 4-methoxy-1-benzoate in 82% yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure methyl 4-methoxybenzoate as a colorless oil.

Reference： [1]Location in patent: experimental part Ushijima, Sousuke; Moriyama, Katsuhiko; Togo, Hideo [Tetrahedron, 2012, vol. 68, # 24, p. 4701 - 4709]

48
[ 75-91-2 ]
[ 1466-76-8 ]
[ 2065-27-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With copper quinolate In water; dimethyl sulfoxide at 120℃; for 24h;
84%	With copper doped mesoporous polymelamine-formaldehyde In water; dimethyl sulfoxide at 100℃; for 16h;

Reference： [1]Zhu, Yan; Yan, Hong; Lu, Linhua; Liu, Defu; Rong, Guangwei; Mao, Jincheng [Journal of Organic Chemistry, 2013, vol. 78, # 19, p. 9898 - 9905]
[2]Molla, Rostam Ali; Iqubal, Md. Asif; Ghosh, Kajari; Kamaluddin; Islam, Sk. Manirul [Dalton Transactions, 2015, vol. 44, # 14, p. 6546 - 6559]

49
[ 2065-27-2 ]
C₁₀H₁₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium; ammonia / tetrahydrofuran; <i>tert</i>-butyl alcohol / Inert atmosphere; Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 20 °C / Inert atmosphere

Reference： [1]Hirai, Sho; Utsugi, Masayuki; Iwamoto, Mitsuhiro; Nakada, Masahisa [Chemistry - A European Journal, 2015, vol. 21, # 1, p. 355 - 359]

50
[ 2065-27-2 ]
C₁₇H₂₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium; ammonia / tetrahydrofuran; <i>tert</i>-butyl alcohol / Inert atmosphere; Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 20 °C / Inert atmosphere 3: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran; N,N-dimethyl-formamide / 20 °C / Inert atmosphere

Reference： [1]Hirai, Sho; Utsugi, Masayuki; Iwamoto, Mitsuhiro; Nakada, Masahisa [Chemistry - A European Journal, 2015, vol. 21, # 1, p. 355 - 359]

51
[ 2065-27-2 ]
TMG•CF₃I [ No CAS ]
methyl 2,6-dimethoxy-3-(trifluoromethyl)benzoate [ No CAS ]
methyl 2,6-dimethoxy-4-(trifluoromethyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dipotassium peroxodisulfate; copper(II) acetate monohydrate In acetic acid at 90℃; for 24h; Sealed tube; Inert atmosphere; Schlenk technique; Overall yield = 49 %; Overall yield = 32.4 mg;
	With dipotassium peroxodisulfate; copper(II) acetate monohydrate; acetic acid at 90℃; for 24h; Inert atmosphere; Sealed tube; Overall yield = 49 %; Overall yield = 32.4 mg;	4 Methyl 2,6-dimethoxy-3-(trifluoromethyl)benzoate (10a) and methyl 2,6-dimethoxy-4- (trifluoromethyl)benzoate (10b) [00229] Methyl 2,6-dimethoxybenzoate (49.0 mg, 0.250 mmol, 1.00 eq), K2S208 (270 mg, 1.00 mmol, 4.00 eq) and Cu(OAc)2 FontWeight="Bold" FontSize="10" H20 (100 mg, 0.0500 mmol, 0.200 eq) were dissolved in glacial acetic acid (2.00 mL). TMG FontWeight="Bold" FontSize="10" CF3I (0.100 mL, 0.500 mmol, 2.00 eq) was added, the reaction vessel was sealed and heated at 90 °C for 24 hours. The reaction mixture was diluted with saturated aqueous sodium carbonate (50 mL) and the resulting mixture extracted with ethyl acetate (3 x 25 mL). The combined ethyl acetate extracts were dried (MgS04) and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with CH2Cl2/hexanes (1:2 to 1: 1) to afford 32.4 mg (0.123 mmol, 49%) of a mixture of 10a and 10b in a 3.0: 1 ratio. Further purification by preparative TLC (EtOAc/hexanes 1:4) afforded pure 10a as a colorless oil and 10b as a colorless solid, in quantities sufficient for characterization. [00230] Methyl 2,6-dimethoxy-3-(trifluoromethyl)benzoate (10a):R/= 0.22 (EtOAc/hexanes 1:4). NMR spectroscopy: 1H NMR (400 MHz, CDC13, 23 °C) δ ppm 7.58 (d, J = 8.8 Hz, 1H), 6.71 (d, J = 8.8 Hz, 1H), 3.95 (s, 3H), 3.89 (s, 3H), 3.87 (s, 3H). 13C NMR (125 MHz, CDC13, 23 °C) δ ppm 165.8, 160.2, 156.7, 129.3, 123.4 (q, JCF = 272 Hz), 119.2, 116.7 (q, JCF = 31 Hz), 105.9, 63.4, 56.3, 52.8. 19F NMR (376 MHz, CDC13, 23 °C) δ ppm -60.5. Mass spectrometry: HRMS (APCI) (m/z): Calcd for [CuHi2F304]+, [M+H+]: 265.0682. Found, 265.0674. [00231] Methyl 2,6-dimethoxy-4-(trifluoromethyl)benzoate (10b): R/= 0.30 (EtOAc/hexanes 1:4). NMR spectroscopy: 1H NMR (400 MHz, CDC13, 23 °C) δ ppm, 6.79 (s, 2H), 3.92 (s, 3H), 3.87 (s, 6H). 13C NMR (125 MHz, CDC13, 23 °C) δ ppm 165.8, 157.5, 133.2 (q, JcF = 33 Hz), 123.5 (q, JCF = 273 Hz), 115.9, 101.1, 56.3, 52.6. 19F NMR (376 MHz, CDC13, 23 °C) δ ppm -63.1. Mass spectrometry: HRMS (APCI) (m/z): Calcd for [CuHnF304Na]+, [M+]: 287.0502. Found, 287.0483.

Reference： [1]Sladojevich, Filippo; McNeill, Eric; Börgel, Jonas; Zheng, Shao-Liang; Ritter, Tobias [Angewandte Chemie - International Edition, 2015, vol. 54, # 12, p. 3712 - 3716][Angew. Chem., 2015, vol. 127, # 12, p. 3783 - 3787,5]
[2]Current Patent Assignee: HARVARD UNIVERSITY - WO2015/168368, 2015, A1 Location in patent: Paragraph 00229-00231

52
[ 2065-27-2 ]
[ 25370-97-2 ]
methyl 2,6-dimethoxy-3-(methylamino)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With air at 20℃; for 36h; chemoselective reaction;
61%	With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]; trifluoroacetic acid In 2,2,2-trifluoroethanol at 0℃; for 2.5h; regioselective reaction;
61%	With Rh₂(esp)2 In 2,2,2-trifluoroethanol at 0℃; for 2.5h; Inert atmosphere;	4 FIG. 2: Entry 15 Following the general intermolecular amination procedure, methyl 2,6-dimethoxybenzoate (7s: 29 mg, 0.15 mmol), Du Bois' catalyst (2.3 mg, 3.0 μmol), and 32 TsONHMe (45 mg, 0.225 mmol) were stirred at 0° C. in TFE (2 mL) for 2.5 h. Chromatographic purification of the crude product afforded 92 methyl 2,6-dimethoxy-3-(methylamino)benzoate (8s: 20 mg, 61%) as a solid, mp 83.6° C. TLC: Rf≈0.5 (30% EtOAc/hexanes); 1H NMR (400 MHz, CDCl3) δ 6.65-6.58 (m, 2H), 3.92 (s, 3H), 3.77 (s, 3H), 3.75 (s, 3H), 2.81 (s, 3H); 13C NMR (101 MHz, CDCl3) δ 167.01, 148.08, 144.54, 137.11, 118.19, 111.84, 107.79, 60.92, 56.61, 52.43, 30.97. HRMS (ESI+) Calcd. for [C11H15NO4+H]+ 226.1079, Found 226.1074.

Reference： [1]Wang, Tao; Hoffmann, Marvin; Dreuw, Andreas; Hasagić, Edina; Hu, Chao; Stein, Philipp M.; Witzel, Sina; Shi, Hongwei; Yang, Yangyang; Rudolph, Matthias; Stuck, Fabian; Rominger, Frank; Kerscher, Marion; Comba, Peter; Hashmi, A. Stephen K. [Advanced Synthesis and Catalysis, 2021, vol. 363, # 11, p. 2783 - 2795]
[2]Paudyal, Mahesh P.; Adebesin, Adeniyi Michael; Burt, Scott R.; Ess, Daniel H.; Ma, Zhiwei; Kürti, László; Falck, John R. [Science, 2016, vol. 353, # 6304, p. 1144 - 1147]
[3]Current Patent Assignee: WILLIAM MARSH RICE UNIVERSITY - US2019/152892, 2019, A1 Location in patent: Paragraph 0132; 0181; 0182

53
[ 2065-27-2 ]
[ 51410-99-2 ]

Yield	Reaction Conditions	Operation in experiment
50%	With hydroxylamine hydrochloride; potassium hydroxide In methanol at 20℃; for 12h;

Reference： [1]Ohtsuka, Naoya; Okuno, Moriaki; Hoshino, Yujiro; Honda, Kiyoshi [Organic and Biomolecular Chemistry, 2016, vol. 14, # 38, p. 9046 - 9054]

54
[ 2065-27-2 ]
[ 2926-29-6 ]
methyl 2,6-dimethoxy-3-(trifluoromethyl)benzoate [ No CAS ]
methyl 2,6-dimethoxy-4-(trifluoromethyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With sodium persulfate; phosphoric acid In water; acetonitrile at 30℃; for 72h; Sealed tube; Inert atmosphere; Green chemistry; Overall yield = 64 %;
	With ammonium nitrate at 100℃; for 12h; Sealed tube;

Reference： [1]Wang, Dangui; Deng, Guo-Jun; Chen, Shiya; Gong, Hang [Green Chemistry, 2016, vol. 18, # 22, p. 5967 - 5970]
[2]Zhang, Jingyu; Yang, Yun; Fang, Jingxian; Deng, Guo-Jun; Gong, Hang [Chemistry - An Asian Journal, 2017, vol. 12, # 19, p. 2524 - 2527]

55
[ 32585-66-3 ]
[ 2065-27-2 ]

Yield	Reaction Conditions	Operation in experiment
38%	With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 85℃; for 2h; Electrolysis;

Reference： [1]Subramanian, Kripa; Yedage, Subhash L.; Bhanage, Bhalchandra M. [Journal of Organic Chemistry, 2017, vol. 82, # 19, p. 10025 - 10032]

56
[ 773837-37-9 ]
[ 2065-27-2 ]
methyl 3-cyano-2,6-dimethoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In methanol at 25℃; for 4h; Electrolysis;

Reference： [1]Hayrapetyan, Davit; Rit, Raja K.; Kratz, Markus; Tschulik, Kristina; Gooßen, Lukas J. [Chemistry - A European Journal, 2018, vol. 24, # 44, p. 11288 - 11291]

57
[ 2065-27-2 ]
[ 73183-34-3 ]
methyl 2,6-dimethoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate [ No CAS ]
(3,5-dimethoxy-4-methoxycarbonylphenyl)boronic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,5-cyclooctadiene)(methoxy)iridium(l) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin In tetrahydrofuran at 65℃; Inert atmosphere; Reflux;	2.13 Int 14: mixture of methyl 2,6-dimethoxy-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)benzoate / (3,5-dimethoxy-4-methoxycarbonyl-phenyl)boronic acid Methyl 2,6-dimethoxybenzoate (CAS 2065-27-2; 96.6 g, 492 mmol, leq.), Ekpim (312.6 g, 1.23 mol, 2.5 eq.), [Ir(OMe)(COD)]2 (6.5 g, 9.8 mmol, 0.02 eq.) and 3,4,7,8-tetramethyl-l,l0-phenanthroline (Activate Scientific, Cat AS21433; 4.7 g, 20 mmol, 0.04 eq.) are dissolved in THF (1 L). The mixture is degassed with nitrogen and then heated to reflux. The reaction mixture is left to stir at 65 °C overnight. The solvent is concentrated in vacuo and the residue is triturated in diisopropyl ether (400 mL). The solid obtained is dried in a vacuum oven at 40 °C overnight to afford the desired compound.

Reference： [1]Current Patent Assignee: GALAPAGOS - WO2019/105886, 2019, A1 Location in patent: Paragraph 0509

58
[ 2065-27-2 ]
bis(2-bromo-5-(dimethylamino)phenyl)(phenyl)phosphine oxide [ No CAS ]
N-(10-(2,6-dimethoxyphenyl)-7-(dimethylamino)-5-oxido-5-phenyl-3H-acridophosphin-3-ylidene)-N-methylmethanaminium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	Stage #1: bis(2-bromo-5-(dimethylamino)phenyl)(phenyl)phosphine oxide With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Inert atmosphere; Stage #2: methyl 2,6-dimethoxybenzoate In tetrahydrofuran; pentane at -78 - 20℃; for 2.5h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water; pentane at 20℃; for 0.25h; Inert atmosphere;

Reference： [1]Arndt, Hans-Dieter; Nasufovic, Veselin; Sauer, Maria; Vilotijevic, Ivan [Organic and biomolecular chemistry, 2020, vol. 18, # 8, p. 1567 - 1571]

59
[ 2065-27-2 ]
(2-bromo-5-(dimethylamino)phenyl)(2-bromo-5-(pyrrolidin-1-yl)phenyl)(phenyl)phosphine oxide [ No CAS ]
1-(10-(2,6-dimethoxyphenyl)-7-(dimethylamino)-5-oxido-5-phenyl-3H-acridophosphin-3-ylidene)pyrrolidin-1-ium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	Stage #1: (2-bromo-5-(dimethylamino)phenyl)(2-bromo-5-(pyrrolidin-1-yl)phenyl)(phenyl)phosphine oxide With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Inert atmosphere; Stage #2: methyl 2,6-dimethoxybenzoate In tetrahydrofuran; pentane at -78 - 25℃; for 2.5h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water; pentane at 25℃; for 0.25h; Inert atmosphere;

Reference： [1]Arndt, Hans-Dieter; Nasufovic, Veselin; Sauer, Maria; Vilotijevic, Ivan [Organic and biomolecular chemistry, 2020, vol. 18, # 8, p. 1567 - 1571]

60
[ 2065-27-2 ]
bis(2-bromo-5-(dimethylamino)phenyl)(tert-butyl)phosphine oxide [ No CAS ]
[ 64-19-7 ]
N-(5-(tert-butyl)-10-(2,6-dimethoxyphenyl)-7-(dimethylamino)-5-oxido-3H-acridophosphin-3-ylidene)-N-methylmethanaminium acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	Stage #1: bis(2-bromo-5-(dimethylamino)phenyl)(tert-butyl)phosphine oxide With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.5h; Inert atmosphere; Stage #2: methyl 2,6-dimethoxybenzoate In tetrahydrofuran; pentane at -20 - 20℃; for 7h; Inert atmosphere; Stage #3: acetic acid Further stages;

Reference： [1]Arndt, Hans-Dieter; Nasufovic, Veselin; Sauer, Maria; Vilotijevic, Ivan [Organic and biomolecular chemistry, 2020, vol. 18, # 8, p. 1567 - 1571]

61
[ 2065-27-2 ]
[ 5673-07-4 ]

Yield	Reaction Conditions	Operation in experiment
62%	With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; 1,1,3,3-Tetramethyldisiloxane; potassium <i>tert</i>-butylate; 1,3-bis(cyclohexyl)imidazolium tetrafluoroborate In toluene at 110℃; for 12h; Glovebox; Inert atmosphere; Sealed tube;

Reference： [1]Cook, Adam; Prakash, Sekar; Zheng, Yan-Long; Newman, Stephen G. [Journal of the American Chemical Society, 2020, vol. 142, # 18, p. 8109 - 8115]

62
[ 2065-27-2 ]
[ 606-45-1 ]

Yield	Reaction Conditions	Operation in experiment
68%	With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; 1,1,3,3-Tetramethyldisiloxane; tricyclohexylphosphine In toluene at 110℃; for 12h; Glovebox; Inert atmosphere; Sealed tube;

Reference： [1]Cook, Adam; Prakash, Sekar; Zheng, Yan-Long; Newman, Stephen G. [Journal of the American Chemical Society, 2020, vol. 142, # 18, p. 8109 - 8115]

63
[ 2065-27-2 ]
[ 71819-90-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere 2: thionyl chloride; pyridine / chloroform / 0.17 h / 20 °C / Inert atmosphere

Reference： [1]Dobrovetsky, Roman; Fallek, Amit; Kramer, Maria; Portnoy, Moshe; Weiss-Shtofman, Mor [Organic Letters, 2020]

64
[ 2065-27-2 ]
1-(2,6-dimethoxybenzyl)-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere 2: thionyl chloride; pyridine / chloroform / 0.17 h / 20 °C / Inert atmosphere 3: N,N-dimethyl-formamide / 18 h / 90 °C / Inert atmosphere

Reference： [1]Dobrovetsky, Roman; Fallek, Amit; Kramer, Maria; Portnoy, Moshe; Weiss-Shtofman, Mor [Organic Letters, 2020]

65
[ 2065-27-2 ]
1-(2,6-dimethoxyphenyl)-N-methylmethanamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere 2: thionyl chloride; pyridine / chloroform / 0.17 h / 20 °C / Inert atmosphere 3: acetonitrile / 7 h / 90 °C / Sealed tube; Inert atmosphere

Reference： [1]Dobrovetsky, Roman; Fallek, Amit; Kramer, Maria; Portnoy, Moshe; Weiss-Shtofman, Mor [Organic Letters, 2020]

66
[ 2065-27-2 ]
N-(2,6-dimethoxybenzyl)-N-methylpyridin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere 2: thionyl chloride; pyridine / chloroform / 0.17 h / 20 °C / Inert atmosphere 3: acetonitrile / 7 h / 90 °C / Sealed tube; Inert atmosphere 4: N-ethyl-N,N-diisopropylamine / acetonitrile / 48 h / 115 °C / Sealed tube; Inert atmosphere

Reference： [1]Dobrovetsky, Roman; Fallek, Amit; Kramer, Maria; Portnoy, Moshe; Weiss-Shtofman, Mor [Organic Letters, 2020]

67
[ 2150-45-0 ]
[ 74-88-4 ]
[ 2065-27-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;

Reference： [1]Dobrovetsky, Roman; Fallek, Amit; Kramer, Maria; Portnoy, Moshe; Weiss-Shtofman, Mor [Organic Letters, 2020]

68
[ 2065-27-2 ]
C₁₀H₇⁽²⁾H₅O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With perchloric acid; d⁽⁴⁾-methanol at 75℃; for 72h; Inert atmosphere;

Reference： [1]Fischer, Oliver; Hubert, Anja; Heinrich, Markus R. [Journal of Organic Chemistry, 2020, vol. 85, # 18, p. 11856 - 11866]

69
[ 2065-27-2 ]
[ 65977-12-0 ]

Yield	Reaction Conditions	Operation in experiment
84 %Spectr.	With CsPbBr₃; N-ethyl-N,N-diisopropylamine; 1,1-dibromomethane Irradiation;

Reference： [1]Deng, Zhijie; Huang, Yanmin; Li, Yonglong; Wang, Teng; Wang, Ying; Xie, Wei; Yuan, Mingjian; Zhang, Cancan; Zhang, Li; Zhu, Aonan [ACS Catalysis, 2022, p. 5903 - 5910]

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
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.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
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.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
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. 2065-27-2 ]

Quality Control of [ 2065-27-2 ]

Related Doc. of [ 2065-27-2 ]

Product Details of [ 2065-27-2 ]

Safety of [ 2065-27-2 ]

Application In Synthesis of [ 2065-27-2 ]

[ 2065-27-2 ] Synthesis Path-Upstream 1~3

[ 2065-27-2 ] Synthesis Path-Downstream 1~69

Related Functional Groups of [ 2065-27-2 ]

Aryls

Ethers

Esters

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 2065-27-2 ]