Name: 3347-99-7|4-Methylisophthalic acid|98%
Brand: Ambeed
SKU: A409311
Rating: 99 (28 reviews)

1
[ 2142-73-6 ]
[ 3347-99-7 ]

Yield	Reaction Conditions	Operation in experiment
	With nitric acid at 150℃;
	With potassium dichromate; sulfuric acid
	With potassium permanganate

Reference： [1]Claus [Chemische Berichte, 1886, vol. 19, p. 233][Journal fuer Praktische Chemie (Leipzig), 1892, vol. <2> 46, p. 485 Anm.] Claus; Wollner [Chemische Berichte, 1885, vol. 18, p. 1858,1859]
[2]Claus [Chemische Berichte, 1886, vol. 19, p. 233][Journal fuer Praktische Chemie (Leipzig), 1892, vol. <2> 46, p. 485 Anm.] Claus; Wollner [Chemische Berichte, 1885, vol. 18, p. 1858,1859]
[3]Claus [Chemische Berichte, 1886, vol. 19, p. 233][Journal fuer Praktische Chemie (Leipzig), 1892, vol. <2> 46, p. 485 Anm.] Claus; Wollner [Chemische Berichte, 1885, vol. 18, p. 1858,1859]

2
[ 1202-08-0 ]
[ 3347-99-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium permanganate
	With nitric acid

Reference： [1]Claus [Journal fur praktische Chemie (Leipzig 1954), 1892, vol. <2> 46, p. 481 Anm.] Claus [Chemische Berichte, 1886, vol. 19, p. 233][Journal fuer Praktische Chemie (Leipzig), 1892, vol. <2> 46, p. 485 Anm.]
[2]Claus [Journal fur praktische Chemie (Leipzig 1954), 1892, vol. <2> 46, p. 481 Anm.] Nightingale; Shackelford [Journal of the American Chemical Society, 1956, vol. 78, p. 133] Malinowskii; Barabaschowa [Zhurnal Obshchei Khimii, 1949, vol. 19, p. 2088,2089][Chem.Abstr., 1950, p. 3939] Claus [Chemische Berichte, 1886, vol. 19, p. 233][Journal fuer Praktische Chemie (Leipzig), 1892, vol. <2> 46, p. 485 Anm.]

3
[ 1943-88-0 ]
[ 3347-99-7 ]

Yield	Reaction Conditions	Operation in experiment
79.3%	With sodium hydroxide; water In diethylene glycol for 8h; Heating;
	With sulfuric acid
	Stage #1: 2,4-dicyanotoluene With sodium hydroxide In diethylene glycol at 215 - 220℃; Stage #2: With hydrogenchloride	52.A Commercially available 2,4-dichlorotoluene (24.6 g) and dry copperφ cyanide (50 g) in N-methylpyrrolidone (130 ml) were heated under reflux (200-216 °C) for 4 d. While hot (110 0C), the mixture was poured into a flask containing 33 % aq. NH4OH solution (390 ml) and toluene (100 ml) and stirred to break up the lumps. After the mixture was cooled to rt, Et2O (100 ml) was added and filtered through cloth. The precipitate was washed (2 x 100 ml Et2O/CHCl3 1:1). The dark filtrate was poured into a separatory funnel and the phases were separated with the aid of additional Et2O (100 ml). The aqueous phase was extracted with Et2O/CHCl3 1 :1 (2 x 100 ml). The combined organic phases were washed with 10 % NH4OH solution (4 x 110 ml, until the basic phase was no longer blue), with H2O (100 ml), and brine EPO (100 ml). The organic phase was separated, dried over MgSO4 and concentrated. The residue was mixed with NaOH (24.8 g) and diethylene glycol (275 ml) was added' together with a few drops OfH2O. The mixture was heated at 215 - 220 0C overnight. The cooled mixture was diluted with H2O (220 ml) and acidified to pH 1 with 10% aq. HCl. The suspension was filtered and the precipitate washed with 0.1 N HCl (50 ml). The solid was crystallised from glacial acetic acid to afford the title compound (18.4 g, 78 %; MH+ = 181).

With water; sodium hydroxide In diethylene glycol for 120h; Reflux;

Reference： [1]Anzalone, Luigi; Hirsch, Jerry A. [Journal of Organic Chemistry, 1985, vol. 50, # 12, p. 2128 - 2133]
[2]Wagner-Jauregg; Helmert [Chemische Berichte, 1938, vol. 71, p. 2535,2543]
[3]Current Patent Assignee: AMGEN INC - WO2006/116157, 2006, A2 Location in patent: Page/Page column 87-88
[4]Fischer, Stefan; Wentsch, Heike K.; Mayer-Wrangowski, Svenja C.; Zimmermann, Markus; Bauer, Silke M.; Storch, Kirsten; Niess, Raimund; Koeberle, Solveigh C.; Grütter, Christian; Boeckler, Frank M.; Rauh, Daniel; Laufer, Stefan A. [Journal of Medicinal Chemistry, 2013, vol. 56, # 1, p. 241 - 253]

4
[ 67-56-1 ]
[ 3347-99-7 ]
[ 23038-61-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogenchloride
94%	With sulfuric acid Reflux;
74%	With sulfuric acid at 80℃; for 24h; Inert atmosphere of nitrogen; Reflux;	Under nitrogen atmosphere, cone, sulfuric acid (4 rnL) was added to a solution of 4-methylisophthalic acid (Chemical Ibrmula 3) (5 g, 27.8 mmol) in methanol (120 mL) and the solution was fluxed at 80 0C for 24 hours. The reaction progress was monitored using TLC [Hex: EA = 1:1]. When the reaction was completed, the solvent was evaporated and saturated NaHCO3 was added, followed by extraction with CHCl 3. The organic layer thus obtained was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The purification of the concentrate through column chromatography [Hexane: EtOAc = 5:1] afforded 0.68 g of dimethyl 4-methylisophthalate (Chemical Ibrmula 4) (Yield 74%).[141] 1H NMR (400 MHz, CDCl3) δ 8.57 (s, IH), 8.05 (d, IH, J = 8.0 Hz), 7.33 (d, IH, J = 8.0 Hz), 3.93 (s, 3H), 3.92 (s, 3H), 2.67 (s, 3H)

74%	With sulfuric acid at 80℃; for 24h; Inert atmosphere;	2 Under nitrogen atmosphere, conc. sulfuric acid (4 mL) was added to a solution of 4-methylisophthalic acid (Chemical Formula 3) (5 g, 27.8 mmol) in methanol (120 mL) and the solution was fluxed at 80° C. for 24 hours. The reaction progress was monitored using TLC [Hex: EA=1:1]. When the reaction was completed, the solvent was evaporated and saturated NaHCO3 was added, followed by extraction with CHCl3. The organic layer thus obtained was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The purification of the concentrate through column chromatography [Hexane: EtOAc=5:1] afforded 0.68 g of dimethyl 4-methylisophthalate (Chemical Formula 4) (Yield 74%).1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.05 (d, 1H, J=8.0 Hz), 7.33 (d, 1H, J=8.0 Hz), 3.93 (s, 3H), 3.92 (s, 3H), 2.67 (s, 3H)
32.6%	With sulfuric acid at 80℃; for 15h;	7 Dimethyl 4-methylbenzene-1,3-dioate To a solution of 4-methylbenzene-1,3-dioic acid (4.0 g, 22.2 mmol) in methanol (120 mL), H2SO4 (4 mL) was added and the resulting mixture was stirred at 80 °C for 15 hours. The mixture was concentrated in vacuo and the residue was partitioned between aqueous sodium bicarbonate solution and dichloromethane. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford the desired product (1.5 g, 32.6% yield). ESI-MS m/z: 209.0 [M+H]+.
	With ion-exchange resin + form>
	With pyridine; copper(II) sulfate
	With sulfuric acid for 6h; Reflux;
	With sulfuric acid Reflux;
5.21 g	With sulfuric acid Reflux;	1 Variant A General procedure: The carboxylic moiety was dissolved in an excess amount of the corresponding alcohol which was then heated to reflux. A catalytic amount of concentrated H2SO4 was carefully added. Reaction was monitored to completion. After cooling the reaction, the excess alcohol was removed under reduced pressure. The residue was taken up in EtOAc, washed with a dilute NaOH solution, dried over Na2SO4 and evaporated under reduced pressure producing solid product.

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]
[2]Walter, Niklas M.; Wentsch, Heike K.; Bührmann, Mike; Bauer, Silke M.; Döring, Eva; Mayer-Wrangowski, Svenja; Sievers-Engler, Adrian; Willemsen-Seegers, Nicole; Zaman, Guido; Buijsman, Rogier; Lämmerhofer, Michael; Rauh, Daniel; Laufer, Stefan A. [Journal of Medicinal Chemistry, 2017, vol. 60, # 19, p. 8027 - 8054]
[3]Current Patent Assignee: KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY - WO2010/5148, 2010, A2 Location in patent: Page/Page column 15
[4]Current Patent Assignee: KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY - US2010/4286, 2010, A1 Location in patent: Page/Page column 6
[5]Current Patent Assignee: ARAXES PHARMA LLC - WO2018/68017, 2018, A1 Location in patent: Page/Page column 141; 142
[6]Fissekis,J.D.; Sweet,F. [Journal of Organic Chemistry, 1973, vol. 38, # 11, p. 1963 - 1970]
[7]Strauss,M.J. et al. [Journal of the American Chemical Society, 1968, vol. 90, # 13, p. 3473 - 3478]
[8]Fischer, Stefan; Wentsch, Heike K.; Mayer-Wrangowski, Svenja C.; Zimmermann, Markus; Bauer, Silke M.; Storch, Kirsten; Niess, Raimund; Koeberle, Solveigh C.; Grütter, Christian; Boeckler, Frank M.; Rauh, Daniel; Laufer, Stefan A. [Journal of Medicinal Chemistry, 2013, vol. 56, # 1, p. 241 - 253]
[9]Pedreira, Júlia G. B.; Nahidino, Philipp; Kudolo, Mark; Pantsar, Tatu; Berger, Benedict-Tilman; Forster, Michael; Knapp, Stefan; Laufer, Stefan; Barreiro, Eliezer J. [Journal of Medicinal Chemistry, 2020, vol. 63, # 13, p. 7347 - 7354]
[10]Current Patent Assignee: SYNOVO GMBH - WO2021/38292, 2021, A1 Location in patent: Page/Page column 7; 12; 13; 14

5
[ 64-17-5 ]
[ 3347-99-7 ]
[ 96259-57-3 ]

Yield	Reaction Conditions	Operation in experiment
67.5%	With sulfuric acid for 21h; Heating;

Reference： [1]Anzalone, Luigi; Hirsch, Jerry A. [Journal of Organic Chemistry, 1985, vol. 50, # 12, p. 2128 - 2133]

6
methyl 8-cyano-8-methyl-3-oxo-2-oxabicyclo<2.2.2>oct-5-ene-6-carboxylate [ No CAS ]
[ 3347-99-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium hydroxide for 1h; Heating;

Reference： [1]Shimo, Tetsuro; Yamasaki, Shinichi; Date, Kenichi; Uemura, Hisako; Somekawa, Kenichi [Journal of Heterocyclic Chemistry, 1993, vol. 30, # 2, p. 419 - 423]

7
[ 124-38-9 ]
[ 7697-26-9 ]
[ 3347-99-7 ]

Yield	Reaction Conditions	Operation in experiment
95%		Under nitrogen atmosphere, <strong>[7697-26-9]3-bromo-4-methylbenzoic acid</strong> (Chemical Formula 2) (5 g, 23.3 mmol) was dissolved in THF, and to this solution was dropwise added methylmagnesium bromide in a 3.0 M diethylether solution (8.5 ml, 25.6 mmol) at 0° C. with stirring. The resulting solution was cooled to -65° C. and then n-butyl lithium in a 1.6M hexane solution (29 ml, 46.5 mmol) were added thereto, followed by stirring for 3 hours. The temperature of the reaction solution was elevated to -40° C., and then to room temperature in the presence of dry ice with stirring. The reaction process was monitored with TLC [CH2Cl2:MeOH=4:1]. When the reaction was detected to have gone to completion, saturated NH4Cl was added to the reaction mixture, followed by extraction with ethyl acetate. The aqueous layer thus obtained was adjusted into pH 1 with 1N HCl before additional extraction with ethyl acetate. The organic layer thus formed was dried over anhydrous MgSO4, filtered, and concentrated in vacuo to afford 4-methylisophthalic acid (Chemical Formula 3) (Yield 95percent)1H NMR (400 MHz, CDCl3) delta 8.52 (s, 1H), 8.03 (d, 1H, J=8.0 Hz), 7.40 (d, 1H, J=6.7 Hz), 2.64 (s, 3H)
95.7%		To a solution of <strong>[7697-26-9]3-bromo-4-methylbenzoic acid</strong> (5.0 g, 23.3 mmol) in tetrahydrofuran (20 mL) at -78 °C under an atmosphere of argon, methyl magnesium bromide (8.5 mL, 25.6 mmol) and n-butyl lithium (18.6 mL, 46.6 mmol) were added dropwise. The resulting mixture was stirred at -78 °C for 3 hours. To this mixture, solid CO2 was added and stirring was continued at room temperature for 1 hour. The mixture was poured into aqueous ammonium chloride solution and extracted with ethyl acetate. The aqueous layer was acidified to pH = 1 with aqueous 1 N hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford the product (4.0 g, 95.7percent yield). ESI-MS m/z: 181.2 [M+H]+.

Reference： [1]Patent: US2010/4286,2010,A1 .Location in patent: Page/Page column 6
[2]Patent: WO2018/68017,2018,A1 .Location in patent: Page/Page column 141
[3]Journal of Medicinal Chemistry,2017,vol. 60,p. 8027 - 8054
[4]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2519 - 2524

8
[ 95-63-6 ]
[ 7697-37-2 ]
[ 5156-01-4 ]
[ 3347-99-7 ]
[ 619-04-5 ]
[ 611-01-8 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1869,vol. 151,p. 269

9
[ 95-63-6 ]
[ 108-90-7 ]
cobalt naphthenate [ No CAS ]
[ 5156-01-4 ]
[ 3347-99-7 ]
[ 619-04-5 ]
[ 611-01-8 ]

Reference： [1]Patent: DE767366,1940,
DRP/DRBP Org.Chem.,

10
[ 110-86-1 ]
[ 7719-09-7 ]
[ 854446-61-0 ]
[ 3347-99-7 ]
[ 138642-93-0 ]
4-methyl-isophthalamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Erwaermen des Reaktionsprodukts mit methanol. Kalilauge; weiteres Produkt: Saeure vom F: 158-160grad;

Reference： [1]Bradfield et al. [Journal of the Chemical Society, 1936, p. 1619,1624]

11
[ 103261-68-3 ]
[ 3347-99-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid In water	28 COMPOUND 28: 4-(3,3"-Dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2';6',2"]terpyridin-1'-ylmethyl)-isophthalic Acid Dimethyl Ester EXAMPLE 28 COMPOUND 28: 4-(3,3"-Dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2';6',2"]terpyridin-1'-ylmethyl)-isophthalic Acid Dimethyl Ester 5-Cyano-2-methyl-benzoic acid methyl ester (1.09 g, 6.22 mmol) was suspended in a mixture of water (25 mL) and concentrated sulfuric acid (10 mL). The yellow solution was stirred at 150° C. for 4 hours to give a pale yellow slurry. The reaction mixture was cooled to room temperature and the precipitate was isolated via suction filtration, washed with water (2*10 mL) and dried in vacuo to yield 4-methyl-isophthalic acid as a tan solid.

Reference： [1]Current Patent Assignee: SANOFI - US2005/154201, 2005, A1

12
[ 3347-99-7 ]
[ 16281-94-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2519 - 2524
[2]Journal of the American Chemical Society,1968,vol. 90,p. 3473 - 3478
[3]Journal of Medicinal Chemistry,2017,vol. 60,p. 8027 - 8054
[4]Patent: WO2018/68017,2018,A1

13
[ 3347-99-7 ]
(S)-2-(2-Methyl-propane-1-sulfonylamino)-3-[3-oxo-2-(2-piperidin-4-yl-ethyl)-2,3-dihydro-1H-isoindole-5-carbonyl]-amino}-propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide 5: 90 percent / 6 N HCl / dioxane

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

14
[ 3347-99-7 ]
(S)-2-Methanesulfonylamino-3-[3-oxo-2-(2-piperidin-4-yl-ethyl)-2,3-dihydro-1H-isoindole-5-carbonyl]-amino}-propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide 5: 90 percent / 6 N HCl / dioxane

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

15
[ 3347-99-7 ]
(S)-2-Hexanoylamino-3-[3-oxo-2-(2-piperidin-4-yl-ethyl)-2,3-dihydro-1H-isoindole-5-carbonyl]-amino}-propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide 5: 90 percent / 6 N HCl / dioxane

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

16
[ 3347-99-7 ]
(S)-2-(3-Butyl-ureido)-3-[3-oxo-2-(2-piperidin-4-yl-ethyl)-2,3-dihydro-1H-isoindole-5-carbonyl]-amino}-propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide 5: 90 percent / 6 N HCl / dioxane

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

17
[ 3347-99-7 ]
(S)-3-[3-Oxo-2-(2-piperidin-4-yl-ethyl)-2,3-dihydro-1H-isoindole-5-carbonyl]-amino}-2-(pentane-1-sulfonylamino)-propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide 5: 90 percent / 6 N HCl / dioxane

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

18
[ 3347-99-7 ]
C₂₃H₃₅N₅O₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide 5: 90 percent / 6 N HCl / dioxane

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

19
[ 3347-99-7 ]
(S)-2-(2-Ethoxy-ethanesulfonylamino)-3-[3-oxo-2-(2-piperidin-4-yl-ethyl)-2,3-dihydro-1H-isoindole-5-carbonyl]-amino}-propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide 5: 90 percent / 6 N HCl / dioxane

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

20
[ 3347-99-7 ]
(S)-2-Benzenesulfonylamino-3-[3-oxo-2-(2-piperidin-4-yl-ethyl)-2,3-dihydro-1H-isoindole-5-carbonyl]-amino}-propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide 5: 90 percent / 6 N HCl / dioxane

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

21
[ 3347-99-7 ]
(S)-3-[3-Oxo-2-(2-piperidin-4-yl-ethyl)-2,3-dihydro-1H-isoindole-5-carbonyl]-amino}-2-(thiophene-2-sulfonylamino)-propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide 5: 90 percent / 6 N HCl / dioxane

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

22
[ 3347-99-7 ]
(S)-3-[3-Oxo-2-(2-piperidin-4-yl-ethyl)-2,3-dihydro-1H-isoindole-5-carbonyl]-amino}-2-phenylmethanesulfonylamino-propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide 5: 90 percent / 6 N HCl / dioxane

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

23
[ 3347-99-7 ]
(S)-3-[3-Oxo-2-(2-piperidin-4-yl-ethyl)-2,3-dihydro-1H-isoindole-5-carbonyl]-amino}-2-(pyridine-3-sulfonylamino)-propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide 5: 90 percent / 6 N HCl / dioxane

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

24
[ 3347-99-7 ]
(S)-2-(3-Benzyl-ureido)-3-[3-oxo-2-(2-piperidin-4-yl-ethyl)-2,3-dihydro-1H-isoindole-5-carbonyl]-amino}-propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide 5: 90 percent / 6 N HCl / dioxane

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

25
[ 3347-99-7 ]
4-{2-[6-((S)-2-Methanesulfonylamino-2-methoxycarbonyl-ethylcarbamoyl)-1-oxo-1,3-dihydro-isoindol-2-yl]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

26
[ 3347-99-7 ]
4-((S)-1-Carboxy-2-[3-oxo-2-(2-piperidin-4-yl-ethyl)-2,3-dihydro-1H-isoindole-5-carbonyl]-amino}-ethylsulfamoyl)-benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide 5: 90 percent / 6 N HCl / dioxane

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

27
[ 3347-99-7 ]
2-((S)-1-Carboxy-2-[3-oxo-2-(2-piperidin-4-yl-ethyl)-2,3-dihydro-1H-isoindole-5-carbonyl]-amino}-ethylsulfamoyl)-benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide 5: 90 percent / 6 N HCl / dioxane

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

28
[ 3347-99-7 ]
4-{2-[6-((S)-2-Hexanoylamino-2-methoxycarbonyl-ethylcarbamoyl)-1-oxo-1,3-dihydro-isoindol-2-yl]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

29
[ 3347-99-7 ]
4-(2-{6-[(S)-2-(3-Butyl-ureido)-2-methoxycarbonyl-ethylcarbamoyl]-1-oxo-1,3-dihydro-isoindol-2-yl}-ethyl)-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

30
[ 3347-99-7 ]
4-(2-{6-[(S)-2-Methoxycarbonyl-2-(2-methyl-propane-1-sulfonylamino)-ethylcarbamoyl]-1-oxo-1,3-dihydro-isoindol-2-yl}-ethyl)-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

31
[ 3347-99-7 ]
4-(2-{6-[(S)-2-Methoxycarbonyl-2-(pentane-1-sulfonylamino)-ethylcarbamoyl]-1-oxo-1,3-dihydro-isoindol-2-yl}-ethyl)-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

32
[ 3347-99-7 ]
C₂₉H₄₅N₅O₈S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

33
[ 3347-99-7 ]
4-(2-{6-[(S)-2-(2-Ethoxy-ethanesulfonylamino)-2-methoxycarbonyl-ethylcarbamoyl]-1-oxo-1,3-dihydro-isoindol-2-yl}-ethyl)-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

34
[ 3347-99-7 ]
4-(2-{6-[(S)-2-Methoxycarbonyl-2-(thiophene-2-sulfonylamino)-ethylcarbamoyl]-1-oxo-1,3-dihydro-isoindol-2-yl}-ethyl)-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

35
[ 3347-99-7 ]
4-{2-[6-((S)-2-Benzenesulfonylamino-2-methoxycarbonyl-ethylcarbamoyl)-1-oxo-1,3-dihydro-isoindol-2-yl]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

36
[ 3347-99-7 ]
4-(2-{6-[(S)-2-(3-Benzyl-ureido)-2-methoxycarbonyl-ethylcarbamoyl]-1-oxo-1,3-dihydro-isoindol-2-yl}-ethyl)-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

37
[ 3347-99-7 ]
4-(2-{6-[(S)-2-Methoxycarbonyl-2-(pyridine-3-sulfonylamino)-ethylcarbamoyl]-1-oxo-1,3-dihydro-isoindol-2-yl}-ethyl)-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

38
[ 3347-99-7 ]
4-{2-[6-((S)-2-Methoxycarbonyl-2-phenylmethanesulfonylamino-ethylcarbamoyl)-1-oxo-1,3-dihydro-isoindol-2-yl]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

39
[ 3347-99-7 ]
4-(2-{6-[(S)-2-(2-Carboxy-benzenesulfonylamino)-2-methoxycarbonyl-ethylcarbamoyl]-1-oxo-1,3-dihydro-isoindol-2-yl}-ethyl)-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 95 percent / HCl 2: 80 percent / NBS, 5 mol percent dibenzoyl peroxide / CCl₄ / Heating 3: 1.) TEA, 2.) LiOH / 1.) benzene, reflux, 2.) MeOH, THF, H₂O 4: BOP, N-methylmorpholine / dimethylformamide

Reference： [1]Egbertson; Hartman; Gould; Bednar; Bednar; Cook; Gaul; Holahan; Libby; Lynch Jr.; Lynch; Sitko; Stranieri; Vassallo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2519 - 2524]

40
[ 3347-99-7 ]
[ 96259-62-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 67.5 percent / conc. H₂SO₄ / 21 h / Heating 2: 65 percent / N-bromosuccinimide (NBS) / CCl₄ / 18 h / Heating 3: 51 percent / 1 h / 180 °C

Reference： [1]Anzalone, Luigi; Hirsch, Jerry A. [Journal of Organic Chemistry, 1985, vol. 50, # 12, p. 2128 - 2133]

41
[ 3347-99-7 ]
[ 96259-72-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 67.5 percent / conc. H₂SO₄ / 21 h / Heating 2: 65 percent / N-bromosuccinimide (NBS) / CCl₄ / 18 h / Heating 3: 51 percent / 1 h / 180 °C 4: 55 percent / H₂ / 5percent Rh/C / ethanol; tetrahydrofuran / 12 h / 60 °C

Reference： [1]Anzalone, Luigi; Hirsch, Jerry A. [Journal of Organic Chemistry, 1985, vol. 50, # 12, p. 2128 - 2133]

42
[ 3347-99-7 ]
[ 96259-66-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 67.5 percent / conc. H₂SO₄ / 21 h / Heating 2: 0.49 g / H₂ / 5percent Rh/C / methanol; acetic acid / 3 h / Ambient temperature

Reference： [1]Anzalone, Luigi; Hirsch, Jerry A. [Journal of Organic Chemistry, 1985, vol. 50, # 12, p. 2128 - 2133]

43
[ 3347-99-7 ]
[ 96259-71-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 67.5 percent / conc. H₂SO₄ / 21 h / Heating 2: 65 percent / N-bromosuccinimide (NBS) / CCl₄ / 18 h / Heating

Reference： [1]Anzalone, Luigi; Hirsch, Jerry A. [Journal of Organic Chemistry, 1985, vol. 50, # 12, p. 2128 - 2133]

44
[ 99-87-6 ]
[ 3347-99-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: AlCl₃; CS₂ 2: nitric acid
	Multi-step reaction with 2 steps 1: AlCl₃ 2: nitric acid
	Multi-step reaction with 2 steps 1: AlCl₃ 2: nitric acid

	Multi-step reaction with 2 steps 1: CS₂; AlCl₃ 2: KMnO₄
	Multi-step reaction with 2 steps 1: FeCl₃; carbon disulfide / <5 2: nitric acid
	Multi-step reaction with 2 steps 1: AlCl₃; carbon disulfide 2: nitric acid
	Multi-step reaction with 2 steps 1: AlCl₃; carbon disulfide 2: nitric acid

Reference： [1]Claus [Chemische Berichte, 1886, vol. 19, p. 233][Journal fuer Praktische Chemie (Leipzig), 1892, vol. <2> 46, p. 485 Anm.]
[2]Malinowskii; Barabaschowa [Zhurnal Obshchei Khimii, 1949, vol. 19, p. 2088,2089][Chem.Abstr., 1950, p. 3939]
[3]Malinowskii; Barabaschowa [Zhurnal Obshchei Khimii, 1949, vol. 19, p. 2088,2089][Chem.Abstr., 1950, p. 3939]
[4]Claus [Journal fur praktische Chemie (Leipzig 1954), 1891, vol. <2> 43, p. 535][Journal fuer Praktische Chemie (Leipzig), 1892, vol. <2> 46, p. 485 Anm., 487]
[5]Nightingale; Shackelford [Journal of the American Chemical Society, 1956, vol. 78, p. 133]
[6]Nightingale; Shackelford [Journal of the American Chemical Society, 1956, vol. 78, p. 133]
[7]Nightingale; Shackelford [Journal of the American Chemical Society, 1956, vol. 78, p. 133]

45
[ 535-77-3 ]
[ 3347-99-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: AlCl₃; carbon disulfide 2: nitric acid
	Multi-step reaction with 2 steps 1: AlCl₃; carbon disulfide 2: nitric acid

Reference： [1]Nightingale; Shackelford [Journal of the American Chemical Society, 1956, vol. 78, p. 133]
[2]Nightingale; Shackelford [Journal of the American Chemical Society, 1956, vol. 78, p. 133]

46
[ 23038-61-1 ]
[ 7732-18-5 ]
[ 3347-99-7 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; methanol	Dimethyl 4-Methylbenzene-1,3-dicarboxylate (2-20) STR32 4-Methyl-1,3-benzenedicarboxylic Acid (2-21) A solution of 2-20 (1.5 g, 7.2 mmoles) in THF/MeOH/H2 O (1:1:1) (36 ml) at room temperature was treated with LiOH.H2 O (1.5 g, 36 mmoles). After stirring for 3 hours, the solvent was removed and the residue acidified with 1N HCl. This was extracted with EtOAc, and the extract was dried (MgSO4) and concentrated to give 2-21. 1 H NMR (300 MHz, CD3 OD) δ 2.65 (3H, s), 7.40 (1H, d), 8.03 (2H, d), 8.56 (1H, s).

Reference： [1]Current Patent Assignee: MERCK & CO INC - US5648368, 1997, A

47
[ 124-38-9 ]
[ 7697-26-9 ]
[ 75-16-1 ]
[ 3347-99-7 ]

Yield	Reaction Conditions	Operation in experiment
95%		Under nitrogen atmosphere, <strong>[7697-26-9]3-bromo-4-methylbenzoic acid</strong> (Chemical Ibrmula 2) (5 g, 23.3 mmol) was dissolved in THF, and to this solution was dropwise added methyl- magnesium bromide in a 3.0 M diethylether solution (8.5 ml, 25.6 mmol) at 0 0C with stirring. The resulting solution was cooled to -65 0C and then n-butyl lithium in a 1.6M hexane solution (29 ml, 46.5 mmol) were added thereto, followed by stirring for 3 hours. The temperature of the reaction solution was elevated to -40 0C, and then to room temperature in the presence of dry ice with stirring. The reaction process was monitored with TLC [CH2Cl2:Me0H=4:l]. When the reaction was detected to have gone to completion, saturated NH4Cl was added to the reaction mixture, followed by extraction with ethyl acetate. The aqueous layer thus obtained was adjusted into pH 1 with IN HCl before additional extraction with ethyl acetate. The organic layer thus formed was dried over anhydrous MgSO4, filtered, and concentrated in vacuo to afford 4-methylisophthalic acid (Chemical Ibrmula 3) (Yield 95percent)[137] 1H NMR (400 MHz, CDCl3) delta 8.52 (s, IH), 8.03 (d, IH, J = 8.0 Hz), 7.40 (d, IH, J = 6.7 Hz), 2.64(s, 3H) [138]

Reference： [1]Patent: WO2010/5148,2010,A2 .Location in patent: Page/Page column 14

48
[ 3347-99-7 ]
[ 1417403-96-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sulfuric acid / 6 h / Reflux 2.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 1 h / -78 - 0 °C 2.2: -78 - 0 °C
	Multi-step reaction with 2 steps 1.1: sulfuric acid / Reflux 2.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: 0.5 h / -78 °C
	Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: lithium diisopropyl amide / tetrahydrofuran / -78 °C

Multi-step reaction with 2 steps 1.1: sulfuric acid / Reflux 2.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1.25 h / -78 °C 2.2: 1.5 h / -78 - 20 °C

Reference： [1]Fischer, Stefan; Wentsch, Heike K.; Mayer-Wrangowski, Svenja C.; Zimmermann, Markus; Bauer, Silke M.; Storch, Kirsten; Niess, Raimund; Koeberle, Solveigh C.; Grütter, Christian; Boeckler, Frank M.; Rauh, Daniel; Laufer, Stefan A. [Journal of Medicinal Chemistry, 2013, vol. 56, # 1, p. 241 - 253]
[2]Walter, Niklas M.; Wentsch, Heike K.; Bührmann, Mike; Bauer, Silke M.; Döring, Eva; Mayer-Wrangowski, Svenja; Sievers-Engler, Adrian; Willemsen-Seegers, Nicole; Zaman, Guido; Buijsman, Rogier; Lämmerhofer, Michael; Rauh, Daniel; Laufer, Stefan A. [Journal of Medicinal Chemistry, 2017, vol. 60, # 19, p. 8027 - 8054]
[3]Pedreira, Júlia G. B.; Nahidino, Philipp; Kudolo, Mark; Pantsar, Tatu; Berger, Benedict-Tilman; Forster, Michael; Knapp, Stefan; Laufer, Stefan; Barreiro, Eliezer J. [Journal of Medicinal Chemistry, 2020, vol. 63, # 13, p. 7347 - 7354]
[4]Current Patent Assignee: SYNOVO GMBH - WO2021/38292, 2021, A1

49
[ 3347-99-7 ]
[ 1417403-97-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: sulfuric acid / 6 h / Reflux 2.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 1 h / -78 - 0 °C 2.2: -78 - 0 °C 3.1: potassium hydroxide / methanol / 6 h / Reflux
	Multi-step reaction with 3 steps 1.1: sulfuric acid / Reflux 2.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: 0.5 h / -78 °C 3.1: potassium hydroxide / methanol; water / 6 h / Reflux
	Multi-step reaction with 3 steps 1: sulfuric acid / Reflux 2: lithium diisopropyl amide / tetrahydrofuran / -78 °C 3: potassium hydroxide / methanol; water / Reflux

Reference： [1]Fischer, Stefan; Wentsch, Heike K.; Mayer-Wrangowski, Svenja C.; Zimmermann, Markus; Bauer, Silke M.; Storch, Kirsten; Niess, Raimund; Koeberle, Solveigh C.; Grütter, Christian; Boeckler, Frank M.; Rauh, Daniel; Laufer, Stefan A. [Journal of Medicinal Chemistry, 2013, vol. 56, # 1, p. 241 - 253]
[2]Walter, Niklas M.; Wentsch, Heike K.; Bührmann, Mike; Bauer, Silke M.; Döring, Eva; Mayer-Wrangowski, Svenja; Sievers-Engler, Adrian; Willemsen-Seegers, Nicole; Zaman, Guido; Buijsman, Rogier; Lämmerhofer, Michael; Rauh, Daniel; Laufer, Stefan A. [Journal of Medicinal Chemistry, 2017, vol. 60, # 19, p. 8027 - 8054]
[3]Pedreira, Júlia G. B.; Nahidino, Philipp; Kudolo, Mark; Pantsar, Tatu; Berger, Benedict-Tilman; Forster, Michael; Knapp, Stefan; Laufer, Stefan; Barreiro, Eliezer J. [Journal of Medicinal Chemistry, 2020, vol. 63, # 13, p. 7347 - 7354]

50
[ 3347-99-7 ]
[ 40246-96-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: sulfuric acid / 6 h / Reflux 2.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 1 h / -78 - 0 °C 2.2: -78 - 0 °C 3.1: potassium hydroxide / methanol / 6 h / Reflux 4.1: thionyl chloride / dichloromethane / Reflux 5.1: aluminum (III) chloride / dichloromethane / 0.33 h / 0 °C
	Multi-step reaction with 5 steps 1.1: sulfuric acid / Reflux 2.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: 0.5 h / -78 °C 3.1: potassium hydroxide / methanol; water / 6 h / Reflux 4.1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / Reflux 5.1: aluminum (III) chloride / dichloromethane / 0.33 h / 0 °C 5.2: Cooling
	Multi-step reaction with 4 steps 1.1: sulfuric acid / Reflux 2.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C 3.1: potassium hydroxide / methanol; water / Reflux 4.1: thionyl chloride / dichloromethane / Reflux 4.2: 20 °C

Reference： [1]Fischer, Stefan; Wentsch, Heike K.; Mayer-Wrangowski, Svenja C.; Zimmermann, Markus; Bauer, Silke M.; Storch, Kirsten; Niess, Raimund; Koeberle, Solveigh C.; Grütter, Christian; Boeckler, Frank M.; Rauh, Daniel; Laufer, Stefan A. [Journal of Medicinal Chemistry, 2013, vol. 56, # 1, p. 241 - 253]
[2]Walter, Niklas M.; Wentsch, Heike K.; Bührmann, Mike; Bauer, Silke M.; Döring, Eva; Mayer-Wrangowski, Svenja; Sievers-Engler, Adrian; Willemsen-Seegers, Nicole; Zaman, Guido; Buijsman, Rogier; Lämmerhofer, Michael; Rauh, Daniel; Laufer, Stefan A. [Journal of Medicinal Chemistry, 2017, vol. 60, # 19, p. 8027 - 8054]
[3]Pedreira, Júlia G. B.; Nahidino, Philipp; Kudolo, Mark; Pantsar, Tatu; Berger, Benedict-Tilman; Forster, Michael; Knapp, Stefan; Laufer, Stefan; Barreiro, Eliezer J. [Journal of Medicinal Chemistry, 2020, vol. 63, # 13, p. 7347 - 7354]

51
[ 3347-99-7 ]
[ 1417403-99-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: sulfuric acid / 6 h / Reflux 2.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 1 h / -78 - 0 °C 2.2: -78 - 0 °C 3.1: potassium hydroxide / methanol / 6 h / Reflux 4.1: thionyl chloride / dichloromethane / Reflux 5.1: aluminum (III) chloride / dichloromethane / 0.33 h / 0 °C 6.1: tetrahydrofuran / 1.5 h / 20 °C 7.1: tetrahydrofuran
	Multi-step reaction with 6 steps 1.1: sulfuric acid / Reflux 2.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: 0.5 h / -78 °C 3.1: potassium hydroxide / methanol; water / 6 h / Reflux 4.1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / Reflux 5.1: aluminum (III) chloride / dichloromethane / 0.33 h / 0 °C 5.2: Cooling 6.1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / tetrahydrofuran
	Multi-step reaction with 5 steps 1.1: sulfuric acid / Reflux 2.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C 3.1: potassium hydroxide / methanol; water / Reflux 4.1: thionyl chloride / dichloromethane / Reflux 4.2: 20 °C 5.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / tetrahydrofuran / 20 °C

Reference： [1]Fischer, Stefan; Wentsch, Heike K.; Mayer-Wrangowski, Svenja C.; Zimmermann, Markus; Bauer, Silke M.; Storch, Kirsten; Niess, Raimund; Koeberle, Solveigh C.; Grütter, Christian; Boeckler, Frank M.; Rauh, Daniel; Laufer, Stefan A. [Journal of Medicinal Chemistry, 2013, vol. 56, # 1, p. 241 - 253]
[2]Walter, Niklas M.; Wentsch, Heike K.; Bührmann, Mike; Bauer, Silke M.; Döring, Eva; Mayer-Wrangowski, Svenja; Sievers-Engler, Adrian; Willemsen-Seegers, Nicole; Zaman, Guido; Buijsman, Rogier; Lämmerhofer, Michael; Rauh, Daniel; Laufer, Stefan A. [Journal of Medicinal Chemistry, 2017, vol. 60, # 19, p. 8027 - 8054]
[3]Pedreira, Júlia G. B.; Nahidino, Philipp; Kudolo, Mark; Pantsar, Tatu; Berger, Benedict-Tilman; Forster, Michael; Knapp, Stefan; Laufer, Stefan; Barreiro, Eliezer J. [Journal of Medicinal Chemistry, 2020, vol. 63, # 13, p. 7347 - 7354]

52
[ 124-38-9 ]
[ 31543-75-6 ]
[ 3347-99-7 ]

Yield	Reaction Conditions	Operation in experiment
62%		General procedure: In a Schlenk (50 mL) reaction flask with a carbon dioxide balloon attached to a branch tube, add Cu (OAc) 2.H2O (0.02 mmol), 1,2-bis (diphenylphosphine) benzene (0.033 mmol), and 1,4 -Dioxane (3.0mL), PMHS (4.0mmol) was added under stirring, and then the reaction flask was placed in an oil bath at 65 C for 25min to react under a carbon dioxide atmosphere, followed by toluene (15mL), 3- Bromoiodobenzene (1.0mmol), Pd (OAc) 2 (0.05mmol), Xantphos (0.06mmol), Et3N (5.0mmol, 5.0equiva.), Then remove the carbon dioxide and react at 100 C until the raw bromobenzene disappears. After cooling to room temperature, a sodium hydroxide solution (1M, 20.0mL) was added, and the mixture was stirred for 10 minutes and filtered. The solid was washed three times with water. The filtrate was extracted with ethyl acetate (2 × 10mL) and the aqueous layer was left. 1M) adjusted to pH 1-2, extracted with ethyl acetate (3 × 20 mL), dried over anhydrous sodium sulfate, and removed the solvent to obtain m-dibenzoic acid with a yield of 65%

Reference： [1]Patent: CN110724047,2020,A .Location in patent: Paragraph 0141-0143; 0148-0151; 0177

53
[ 7697-26-9 ]
[ 75-16-1 ]
[ 3347-99-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-bromo-4-methylbenzoic acid; methylmagnesium bromide In tetrahydrofuran; diethyl ether at 0℃; for 2h; Inert atmosphere; Stage #2: With n-butyllithium In tetrahydrofuran; diethyl ether; hexane at -75 - -40℃; for 6h; Inert atmosphere;	1 4-methylisopthalic acid (2) 3-Bromo-4-methylbenzoic acid, 1, (10 g; 46.50 mmol) was weighed into a 250-mL 3-necked round bottom flask and taken up in dry THF (50 mL) under argon atmosphere. Using a cryostat, the reaction was cooled to 0 °C. Under argon, 3M methyl magnesium bromide solution (17.7 mL; 51.15 mmol) in Et2O was added dropwise. The reaction was stirred for 2 h. The reaction solution was then cooled to -75 oC, and to this was added carefully, 2.5M n-BuLi solution in hexane (35.05 mL; 93.00 mmol) dropwise. The resulting reaction was stirred for 3h and allowed to warm to -40 oC. At this point, dry ice (25 g) was added to the reaction. Cooling was removed and the reaction stirred for an additional 3 h. When reaction was completed, the reaction was terminated by the addition of 20% NaOH. This was washed with EtOAc. The aqueous phase was cooled in an ice bath and was acidified by the addition concentrated HCl until the product precipitated out. The precipitate was filtered and washed with a very small amount of EtOAc producing the crude product as a white solid (7.32 g; 87.4% yield). If the yield was too low, the EtOAc phase in the filtrate was separated and evaporated under reduced pressure. The residue was taken up in EtOAc and H2O and then filtered. 1H-NMR (200 MHz, DMSO-d6) d 8.37 (d, J = 1.8 Hz, 1H), 7.96 (dd, J = 7.9, 1.9 Hz, 1H), 7.43 (d, J = 8.1 Hz, 1H), 4.33 (s, 2H), 2.57 (s, 3H) 13C NMR (50 MHz, DMSO-d6) d 168.71, 167.42, 145.13, 132.89, 131.96, 131.44, 129.35, 22.19. MS(FABneg) (m/z): 179,0 [M-H]-

Reference： [1]Current Patent Assignee: SYNOVO GMBH - WO2021/38292, 2021, A1 Location in patent: Page/Page column 12; 13

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CAS No. :	3347-99-7	MDL No. :	MFCD09878876
Formula :	C₉H₈O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PNWSHHILERSSLF-UHFFFAOYSA-N
M.W :	180.16	Pubchem ID :	595750
Synonyms :

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

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. 3347-99-7 ] {[proInfo.proName]}

Quality Control of [ 3347-99-7 ]

Related Doc. of [ 3347-99-7 ]

Product Details of [ 3347-99-7 ]

Safety of [ 3347-99-7 ]

Application In Synthesis of [ 3347-99-7 ]

[ 3347-99-7 ] Synthesis Path-Downstream 1~53

Related Functional Groups of
[ 3347-99-7 ]

Aryls

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

[ CAS No. 3347-99-7 ] {[proInfo.proName]}

Quality Control of [ 3347-99-7 ]

Related Doc. of [ 3347-99-7 ]

Product Details of [ 3347-99-7 ]

Safety of [ 3347-99-7 ]

Application In Synthesis of [ 3347-99-7 ]

[ 3347-99-7 ] Synthesis Path-Downstream 1~53

Related Functional Groups of [ 3347-99-7 ]

Aryls

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 3347-99-7 ]