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Quality Control of [ 335592-60-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 335592-60-4 ]

CAS No. :	335592-60-4	MDL No. :	MFCD22494620
Formula :	C₂₀H₃₂BNO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	361.28	Pubchem ID :	-
Synonyms :

Safety of [ 335592-60-4 ]

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

Application In Synthesis of [ 335592-60-4 ]

* 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.

Downstream synthetic route of [ 335592-60-4 ]

[ 335592-60-4 ] Synthesis Path-Downstream 1~65

1
[ 214973-83-8 ]
[ 73183-34-3 ]
[ 335592-60-4 ]

Yield	Reaction Conditions	Operation in experiment
84%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 80℃; for 5h;	Step 4: Preparation of tert-butyl {1-methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl}carbamate A suspension of tert-butyl[1-(4-bromophenyl)-1-methylethyl]carbamate (500 mg) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane (485 mg) and potassium acetate (468 mg) and PdCl2(dppf)CH2Cl2 (39 mg) in dimethylsulfoxide (8 mL) was degassed for 5 min. then stirred at 80 C. for 5 h. The reaction mixture was diluted with benzene and filtered. The filtrate was washed with brine (5 times). The organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (0-15% ethyl acetate in hexanes) gave the product (481 mg, 84%). 1HNMR (CDCl3) 400 MHz delta: 7.77 (d, J=8.3 Hz, 2H), 7.40 (d, J=8.3 Hz, 2H), 4.95 (br s, 1H), 1.61 (br s, 6H), 1.46-1.07 (m, 9H), 1.33 (s, 12H).
5.67 g	With potassium acetate; palladium diacetate; XPhos; In acetonitrile; at 75℃; for 18h;Inert atmosphere;	Step 2: tert-butyl (2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)propan-2- yl)carbamate: The product from Step 1 above (6 g, 18.52 mmol, 97% purity), bis- (pinacolato)diboron (5.82 g, 22.91 mmol), palladium(II) acetate (0.107 g, 0.477 mmol), potassium acetate (5.62 g, 57.3 mmol) and XPhos (0.457 g, 0.955 mmol) were combined in MeCN (50 ml). The vessel was purged with N2 then heated at 75 C for 18 h. The reaction mixture was cooled, filtered through Celite, washing with MeCN (2 x 50 ml), and concentrated in vacuo to afford a brown oil. The residue was partitioned between DCM (50 ml) and water (50 ml). The phases were separated and the organic phase was concentrated in vacuo to afford a brown soild. The crude product was purified by columnchromatography (220 g cartridge, 0-20% EtOAc/isohexane) to afford the title compound (5.67 g, 15.1 mmol, 96% purity) as an off-white solid. LCMS (Method 1): m/z 306 (M+H- C4H8)+ at 2.83 min.

Reference： [1]Patent: US2012/108574,2012,A1 .Location in patent: Page/Page column 112
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2179 - 2183
[3]Patent: WO2016/102672,2016,A2 .Location in patent: Page/Page column 104

2
[ 335592-60-4 ]
[ 5750-76-5 ]
[ 335592-59-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2179 - 2183

3
[ 335592-60-4 ]
[ 937366-50-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2179 - 2183

4
[ 335592-60-4 ]
[ 335592-43-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2179 - 2183

5
[ 335592-60-4 ]
C₁₉H₁₈BrClN₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2179 - 2183

6
[ 335592-60-4 ]
4-[4-(1-Amino-1-methylethyl)phenyl]-5-chloro-N-[4-(2-hydroxyethyl)phenyl]pyrimidine-2-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2179 - 2183

7
[ 335592-60-4 ]
C₂₇H₃₃ClN₄O₅S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2179 - 2183

8
[ 335592-60-4 ]
C₂₇H₃₄ClN₅O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2179 - 2183

9
[ 335592-60-4 ]
C₂₂H₂₆ClN₅ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2179 - 2183

10
[ 335592-60-4 ]
C₂₈H₃₆ClN₅O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2179 - 2183

11
[ 335592-60-4 ]
C₂₃H₂₈ClN₅ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2179 - 2183

12
[ 335592-60-4 ]
C₃₀H₃₈ClN₅O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2179 - 2183

13
[ 335592-60-4 ]
4-[4-(1-Amino-1-methylethyl)phenyl]-5-chloro-N-[4-(2-(pyrrolidin-1-yl)ethyl)phenyl]pyrimidine-2-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2179 - 2183

14
[ 335592-60-4 ]
C₃₀H₃₈ClN₅O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2179 - 2183

15
[ 335592-60-4 ]
4-[4-(1-Amino-1-methylethyl)phenyl]-5-chloro-N-[4-(2-morpholinoethyl)phenyl]pyrimidine-2-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2179 - 2183

16
[ 335592-60-4 ]
C₃₁H₄₁ClN₆O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2179 - 2183

17
[ 335592-60-4 ]
4-[4-(1-Amino-1-methylethyl)phenyl]-5-chloro-N-[4-(2-(4-methylpiperazin-1-yl)ethyl)phenyl]pyrimidine-2-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2179 - 2183

18
[ 24424-99-5 ]
[ 335592-60-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2179 - 2183
[2]Patent: WO2016/102672,2016,A2

19
[ 17797-12-5 ]
[ 335592-60-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2179 - 2183

20
[ 214973-83-8 ]
[ 61676-62-8 ]
[ 335592-60-4 ]

Yield	Reaction Conditions	Operation in experiment
58%		(Referential Example 6) Synthesis of 4-(1-tert-butoxycarbonylamino-1-methylethyl)-1-(4,4,5,5-tetramethyl[1,3,2]dioxaborolanyl)benzene (referential compound 6-1) A 0.95M sec-butyl lithium/n-hexane solution (370 ml, 350 mmol) was dropped, in an argon stream with stirring at -78C, into a solution of 50 g (160 mmol) of <strong>[214973-83-8]1-bromo-4-(1-tert-butoxycarbonylamino-1-methylethyl)benzene</strong>(referential compound 4-1) in 800 ml of diethyl ether and the mixture was stirred for 30 minutes. After that, 97 ml (480 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl[1,3,2]dioxaborolane was dropped thereinto at -78C and the mixture was stirred at -50C for 2 hours. After the reaction was finished, 300 g of a saturated aqueous solution of ammonium chloride and then 450 ml of water were successively added thereto and the mixture was separated into layers. An aqueous layer was extracted with 300 ml of ethyl acetate again and the organic layers were combined, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated in vacuo. n-Hexane (100 ml) was added to the resulting residue and the resulting solid was filtered off and successively washed with 100 ml of a mixed solvent (n-hexane: ethyl acetate = 4:1 (v/v)) and 100 ml of n-hexane to give 33 g of the title compound as white powder (yield: 58%). Melting point: 142 to 144C Rf value: 0.38 (n-hexane: ethyl acetate = 4:1 (v/v)) Mass spectrum (CI, m/z): 362 (M+ + 1) 1H-NMR spectrum (CDCl3, delta ppm): 1.10-1.50 (m, 21H), 1.61 (s, 6H), 4.93 (brs, 1H), 7.37-7.42 (m, 2H), 7.74-7.79 (m, 2H)
58%		370 ml (350 mmol) of a 0.95 M sec-butyl lithium/n-hexane solution was added dropwise to a solution of 50 g (160 mmol) of <strong>[214973-83-8]1-bromo-4-(1-tert-butoxycarbonylamino-1-methylethyl)benzene</strong> (Reference Compound 4-1) in 800 ml of diethyl ether at -78 C. in an argon stream with stirring, and the mixture was stirred for 30 minutes. Then, 97 ml (480 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl[1,3,2]dioxaborolane was added dropwise thereto at -78 C. and the mixture was stirred at -50 C. for 2 hours. After the reaction was completed, 300 g of a saturated aqueous solution of ammonium chloride was added to the resulting solution, and 450 ml of water was poured into the solution to separate the mixture into layers. An aqueous layer was extracted with 300 ml of ethyl acetate again and the organic layers were combined, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. 100 ml of n-hexane was added to the resulting residue and the resulting solid was collected by filtration and successively washed with 100 ml of a mixed solvent (n-hexane:ethyl acetate=4:1 (v/v)) and 100 ml of n-hexane, whereby 33 g of the title compound was obtained as white powder (yield: 58%). Melting point: 142 to 144 C. Rf value: 0.38 (n-hexane:ethyl acetate=4:1 (v/v)) Mass spectrum (CI, m/z): 362 (M++1) 1H-NMR spectrum (CDCl3, deltappm): 1.10-1.50 (m, 21H), 1.61 (s, 6H), 4.93 (brs, 1H), 7.37-7.42 (m, 2H), 7.74-7.79 (m, 2H)
58%		(Reference Example 5) Synthesis of 4-(1-tert-butoxycarbonylamino-1-methylethyl)-1-(4,4,5,5-tetramethyl[1,3,2]dioxaborolanyl)benzene (Reference compound 5) 370 ml (350 mmol) of a 0.95 M sec-butyl lithium/ n-hexane solution was added dropwise to a solution of 50 g (160 mmol) of <strong>[214973-83-8]1-bromo-4-(1-tert-butoxycarbonylamino-1-methylethyl)benzene</strong> (Reference compound 4-1) in 800 ml of diethyl ether at -78C in an argon stream with stirring, and the mixture was stirred for 30 minutes. Then, 97 ml (480 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl[1,3,2] dioxaborolane was added dropwise thereto at -78C and the mixture was stirred at -50C for 2 hours. After the reaction was completed, 300 g of a saturated aqueous solution of ammonium chloride was added to the resulting solution, and 450 ml of water was poured into the solution to separate the mixture into layers. An aqueous layer was extracted with 300 ml of ethyl acetate again and the organic layers were combined, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. 100 ml of n-hexane was added to the resulting residue and the resulting solid was collected by filtration and successively washed with 100 ml of a mixed solvent (n-hexane: ethyl acetate = 4: 1 (v/v)) and 100 ml of n-hexane, whereby 33 g of the title compound was obtained as white powder (yield: 58%). Melting point: 142 to 144C Rf value: 0.38 (n-hexane: ethyl acetate = 4: 1 (v/v)) Mass spectrum (CI, m/z): 362 (M++1) 1H-NMR spectrum (CDCl3, deltappm): 1.10-1.50 (m, 21H), 1.61 (s, 6H), 4.93 (brs, 1H), 7.37-7.42 (m, 2H), 7.74-7.79 (m, 2H)

Reference： [1]Patent: EP1679308,2006,A1 .Location in patent: Page/Page column 33
[2]Patent: US2009/12123,2009,A1 .Location in patent: Page/Page column 7
[3]Patent: EP1870099,2007,A1 .Location in patent: Page/Page column 10

21
[ 335592-60-4 ]
[ 850363-46-1 ]
[ 850360-93-9 ]

Yield	Reaction Conditions	Operation in experiment
56%	With cesium fluoride;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; for 2h;Heating / reflux;	(Example 1) Synthesis of 1-acetyl-5-[4-(1-tert-butoxycarbonylamino-1-methylethyl)phenyl]-1H-indazole (compound 1-1) 4-(1-tert-Butoxycarbonylamino-1-methylethyl)-1-(4,4,5,5-tetramethyl[1,3,2]dioxaborolanyl)benzene (referential compound 6-1) (1.26 g, 3.49 mmol), 792 mg (5.21 mmol) of cesium fluoride, 400 mg (0.346 mmol) of tetrakis(triphenylphosphine) palladium and 20 ml of 1,2-dimethoxyethane were added to 500 mg (1.74 mmol) of 1-acetyl-5-iodo-1H-indazole (referential compound 12-1) and the mixture was heated to reflux with stirring for 2 hours in an argon stream. After the reaction was finished, the reaction solution was poured into 50 ml of water and the mixture was extracted with 100 ml of ethyl acetate. The organic layer was successively washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resulting residue was subjected to a silica gel column chromatography (eluding solvent: n-hexane: ethyl acetate = 5:1 (v/v)) and the fraction containing the aimed product was concentrated in vacuo to give 385 mg of the title compound as white powder (yield: 56%). Rf value: 0.48 (n-hexane: ethyl acetate = 2:1 (v/v)) Mass spectrum (CI, m/z): 394 (M+ + 1) 1H-NMR spectrum (CDCl3, delta ppm): 1.40 (brs, 9H), 1.67 (s, 6H), 2.81 (s, 3H), 4.98 (brs, 1H), 7.48-7.52 (m, 2H), 7.57-7.61 (m, 2H), 7.80 (dd, J1 = 8.8Hz, J2 = 1.7Hz, 1H), 7.91 (dd, J1 = 1.7Hz, J2 = 0.8Hz, 1H), 8.17 (d, J = 0.8Hz, 1H), 8.46-8.50 (m, 1H)
56%	With cesium fluoride;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; for 2h;Heating / reflux;	1.26 g (3.49 mmol) of <strong>[335592-60-4]4-(1-tert-butoxycarbonylamino-1-methylethyl)-1-(4,4,5,5-tetramethyl[1,3,2]dioxaborolanyl)benzene</strong> (Reference compound 5), 792 mg (5.21 mmol) of cesium fluoride, 400 mg (0.346 mmol) of tetrakis(triphenylphosphine)palladium and 20 ml of 1,2-dimethoxyethane were added to 500 mg (1.74 mmol) of 1-acetyl-5-iodo-1H-indazole (Reference compound 7) and the mixture was stirred for 2 hours in an argon stream under a condition of heating to reflux. After the reaction was completed, the reaction solution was poured into 50 ml of water and the mixture was extracted with 100 ml of ethyl acetate. The organic layer was successively washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluding solvent: n-hexane:ethyl acetate=5:1 (v/v)) and the fraction containing the desired substance was concentrated under reduced pressure, whereby 385 mg of the title compound was obtained as white powder (yield: 56%). Rf value: 0.48 (n-hexane:ethyl acetate=2:1 (v/v)) Mass spectrum (CI, m/z): 394 (M++1) 1H-NMR spectrum (CDCl3, deltappm): 1.40 (brs, 9H), 1.67 (s, 6H), 2.81 (s, 3H), 4.98 (brs, 1H), 7.48-7.52 (m, 2H), 7.57-7.61 (m, 2H), 7.80 (dd, J1=8.8 Hz, J2=1.7 Hz, 1H), 7.91 (dd, J1=1.7 Hz, J2=0.8 Hz, 1H), 8.17 (d, J=0.8 Hz, 1H), 8.46-8.50 (m, 1H)
56%	With cesium fluoride;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; for 2h;	(Example 1) Synthesis of 1-acetyl-5-[4-(1-tert-butoxycarbonylamino-1-methylethyl)phenyl]-1H-indazole (Compound 1-1) 1.26 g (3.49 mmol) of 4-(1-tert-butoxycarbonylamino - 1-methylethyl)-1-(4,4,5,5-tetramethyl[1,3,2]dioxaborolanyl)benzene (Reference compound 5), 792 mg (5.21 mmol) of cesium fluoride, 400 mg (0.346 mmol) of tetrakis (triphenylphosphine)palladium and 20 ml of 1,2-dimethoxyethane were added to 500 mg (1.74 mmol) of 1-acetyl-5-iodo-1H-indazole (Reference compound 7) and the mixture was stirred for 2 hours in an argon stream under a condition of heating to reflux. After the reaction was completed, the reaction solution was poured into 50 ml of water and the mixture was extracted with 100 ml of ethyl acetate. The organic layer was successively washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluding solvent: n-hexane: ethyl acetate = 5: 1 (v/v)) and the fraction containing the desired substance was concentrated under reduced pressure, whereby 385 mg of the title compound was obtained as white powder (yield: 56%). Rf value: 0.48 (n-hexane: ethyl acetate = 2: 1 (v/v)) Mass spectrum (CI, m/z): 394 (M++1) 1H-NMR spectrum (CDCl3, deltappm): 1.40 (brs, 9H), 1.67 (s, 6H), 2.81 (s, 3H), 4.98 (brs, 1H), 7.48-7.52 (m, 2H), 7.57-7.61 (m, 2H), 7.80 (dd, J1=8.8Hz, J2=1.7Hz, 1H), 7.91 (dd, J1=1.7Hz, J2=0.8Hz, 1H), 8.17 (d, J=0.8Hz, 1H), 8.46-8.50 (m, 1H)

Reference： [1]Patent: EP1679308,2006,A1 .Location in patent: Page/Page column 60
[2]Patent: US2009/12123,2009,A1 .Location in patent: Page/Page column 15
[3]Patent: EP1870099,2007,A1 .Location in patent: Page/Page column 22

22
[ 335592-60-4 ]
1-tert-butoxycarbonyl-5-iodo-4-nitro-1H-indazole [ No CAS ]
[ 850360-99-5 ]

Yield	Reaction Conditions	Operation in experiment
	With cesium fluoride;tris(dibenzylideneacetone)dipalladium(0) chloroform complex; In 1,2-dimethoxyethane; for 2h;Heating / reflux;	As hereunder, the compounds 1-2 to 1-31 were produced in accordance with the production process for the compound 1-1. Incidentally, in the synthesis of the compounds 1-7 to 1-11, an adduct of tris(dibenzylideneacetone) dipalladium with chloroform was used instead of tetrakis(triphenylphosphine) palladium and, in the synthesis of the compounds 1-12 to 1-31, a 2M aqueous solution of sodium carbonate was used instead of cesium fluoride; 1-tert-Butoxycarbonyl-5-[4-(1-tert-butoxycarbonylamino-1-methylethyl)phenyl]-4-nitro-1H-indazole (compound 1-7) Rf value: 0.36 (n-hexane : ethyl acetate = 2:1 (v/v)) Mass spectrum (FAB, m/z): 496 (M+) 1H-NMR spectrum (CDCl3, delta ppm): 1.38 (brs, 9H), 1.67 (s, 6H), 1.75 (s, 9H), 4.95 (brs, 1H), 7.31-7.34 (m, 2H), 7.46-7.51 (m, 2H), 7.60 (d, J = 8.7Hz, 1H), 8.42(d, J = 0.7Hz, 1H), 8.45 (dd, J1 = 8.7Hz, J2 = 0.7Hz, 1H)

Reference： [1]Patent: EP1679308,2006,A1 .Location in patent: Page/Page column 60-61

23
[ 214973-83-8 ]
[1,1'-bis(di-phenylphosphino)ferrocene]dichloropalladium [ No CAS ]
[ 73183-34-3 ]
[ 335592-60-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate; In dichloromethane; N,N-dimethyl-formamide;	A mixture of <strong>[214973-83-8]tert-butyl N-{1-(4-bromophenyl)-1-methylethyl}carbamate</strong> (1.57 g, 5.0 mmol), bis(pinacolato)diboron (1.40 g, 5.5 mmol), [1,1'-bis(di-phenylphosphino)ferrocene]dichloropalladium(II) (123 mg, 0.015 mmol) and potassium acetate (1.47 g, 15.0 mmol) was dissolved in dry DMF (20 ml) under nitrogen and heated to 80 for 5 h. The reaction was then concentrated under reduced pressure, the resulting residue taken up in dichloromethane (80 ml) and washed with water (180 ml), then brine (180 ml), dried (MgSO4) and again concentrated. The residue was subjected to column chromatography (silica gel; 15% ethyl acetate-hexane) to give tert-butyl N-{1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1-methylethyl}carbamate (1.55 g) as a white solid m.p. 140. deltaH (CDCl3) 7.77 (2H, d, J 8.3 Hz), 7.40 (2H, d, J 8.4 Hz), 1.63 (6H, s) and 1.34 (21H, s).

Reference： [1]Patent: US6600037,2003,B1

24
[ 101184-73-0 ]
[ 335592-60-4 ]

Reference： [1]Patent: US2012/108574,2012,A1

25
[ 335592-60-4 ]
[ 1374262-88-0 ]
[ 1374263-32-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 80℃; for 18h;	Step 5: Preparation of tert-butyl {1-methyl-1-[4-(2-phenyl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl]ethyl}carbamate A suspension of 3-bromo-2-phenyl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepine (50 mg) and <strong>[335592-60-4]tert-butyl {1-methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl}carbamate</strong> (93 mg) and potassium phosphate (82 mg) and PdCl2(dppf)CH2Cl2 (11 mg) in dioxane (2.5 mL) and H2O (0.25 mL) was degassed for 5 min then stirred at 80 C. for 18 h. The reaction mixture was concentrated under reduced pressure. Purification by column chromatography (0-50% ethyl acetate in hexanes) gave the product (56 mg, 80%). 1HNMR (DMSO-d6) 400 MHz delta: 8.54 (s, 1H), 8.09-8.00 (m, 1H), 7.95 (dd, 1H, J=7.8, 1.4 Hz), 7.55-7.48 (m, 2H), 7.38-7.32 (m, 3H), 7.31-7.19 (m, 5H), 7.17-7.07 (m, 3H), 6.91-6.77 (m, 1H), 6.70-6.59 (m, 1H), 1.50 (br s, 6H), 1.41-1.05 (m, 9H). LCMS: 544 [M+H].

Reference： [1]Patent: US2012/108574,2012,A1 .Location in patent: Page/Page column 112

26
[ 850144-81-9 ]
[ 335592-60-4 ]

Reference： [1]Patent: US2012/108574,2012,A1

27
[ 335592-60-4 ]
[ 1431551-88-0 ]
[ 1431551-92-6 ]

Yield	Reaction Conditions	Operation in experiment
120 mg	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; water; at 80℃; for 4h;Inert atmosphere; Microwave irradiation;	Example 4 N-((1 R,2S)-1 -(4'-(2-aminopropan-2-yl)-[1 , 1 '-biphenyl]-4-yl)-3-fluoro- 1-hydroxypropan-2-yl)-2,2-dichloroacetamide Step 1 : Preparation of tert-butyl (2-(4'-((4S,5R)-3-(2,2-dichloroacetyl)-4- (fluoromethyl)-2,2-dimethyloxazolidin-5-yl)-[1 , 1 '-biphenyl]-4-yl)propan-2- yl)carbamateA mixture of tert-butyl (2-(4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)phenyl)- propan-2-yl)carbamate (previously described in Biorganic and Medicinal Chemistry Letters, 2007, 2179, 134 mg, 0.37 mmol), (4S,5R)-4- (fluoromethyl)-5-(4-iodophenyl)-2,2-dimethyloxazolidine (150 mg, 0.337 mmol), Cs2C03 (240 mg, 0.72 mmol) in dioxane (4 mL) and water (1 mL) is bubbled with nitrogen gas for 2 minutes. To this mixture is added Pd(PPh3)4 (54 mg, 0.047 mmol) and the resulting reaction mixture heated at 80C in microwave reactor for 4 hours. Reaction is diluted with water (10 ml) and extracted with ethyl acetate. Combined organic solution is dried over Na2S04 and concentrated. Crude product is absorbed on celite, and purified on silica gel column using 0 to 30% EtOAC/heptane to give the title compound (120 mg). 1H NMR (400 MHz, CDCI3)5: (1 H-NMR) 1.42 (bs, 9H), 1 .67 (bs, 9H), 1.74 (bs, 3H) 4.47-4.74 (bm, 1.5H), 4.76-4.87 (bm 0.5H) 4.95-5.12 (bm, 1.5H) 5.16-5.31 (bm, 0.5H), 6.24- 6.46 (bs, 1 H), 7.47 - 7.53 (m, 4H), 7.56 (d, 2H, J = 8.0Hz), 7.64 (d, 2H, J = 8.0Hz).

Reference： [1]Patent: WO2013/57619,2013,A1 .Location in patent: Page/Page column 20; 21

28
[ 335592-60-4 ]
N-(6-bromo-5-phenyl-1,2,4-triazin-3-yl)-2-(trans-4-(2-oxooxazolidin-3-yl)cyclohexyl)-N-(2-(trans-4-(2-oxooxazolidin-3-yl)cyclohexyl)acetyl)acetamide [ No CAS ]
N-(6-(4-(2-aminopropan-2-yl)phenyl)-5-phenyl-1,2,4-triazin-3-yl)-2-(trans-4-(2-oxooxazolidin-3-yl)cyclohexyl)acetamide [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

29
[ 335592-60-4 ]
N-(6-bromo-5-phenyl-1,2,4-triazin-3-yl)-2-(trans-4-(2-oxooxazolidin-3-yl)cyclohexyl)-N-(2-(trans-4-(2-oxooxazolidin-3-yl)cyclohexyl)acetyl)acetamide [ No CAS ]
C₃₄H₄₂N₆O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 2: N-(6-(4-(2-aminopropan-2-yl)phenyl)-5-phenyl-l,2,4-triazin-3-yl)-2-(trans-4-(2- oxooxazolidin-3-yl)cyclohexyl)acetamide: A solution of Na2C03 (85 mg, 0.806 mmol) in water (1 ml) was added to a stirred solution of the product from Intermediate 2 Step 2 (107 mg, 0.296 mmol) and the product from Step 1 above (180 mg, 0.269 mmol) in dioxane (5 ml). The resultant mixture was degassed for 5 min and then tetrakis- (triphenylphosphine)palladium(O) (31.1 mg, 0.027 mmol) was added and the resultant mixture heated at 90 C overnight. The reaction mixture was poured into water (100 ml) and extracted with EtOAc (3 x 50 ml). The combined extracts were washed with brine (50 ml), dried over MgS04, filtered and concentrated in vacuo. The residue was dissolved in DCM (2 ml) and then TFA (1 ml, 13.0 mmol) was added and the reaction mixture was stirred at RT for 1 h. The mixture was concentrated in vacuo. To remove residual TFA, the residue was thrice resuspended in toluene (20 ml) and concentrated in vacuo. The residue was purified by preparative HPLC (Varian PrepStar, Waters X-Bridge Prep-C18, 5 muiotaeta, 19x50 mm column, 20-40% MeCN in 10 mM ammonium bicarbonate(aq)) to afford the title compound (22 mg, 0.042 mmol, 99% purity) as a white solid. LCMS (Method 1): m/z 515 (M+H)+, 513 (M-H)~, at 1.21 min. 1H NMR (400 MHz, DMSO-J6) delta 11.18 (s, 1H ,7.59 - 7.46 (m, 5H), 7.43 - 7.37 (m, 4H), 4.29 - 4.18 (m, 2H), 3.56 - 3.41 (m, 3H), 2.47 (d, 7 = 6.6 Hz, 2H), 2.01 (s, 1H), 1.89 - 1.75 (m, 2H), 1.74 - 1.63 (m, 2H), 1.57 - 1.43 (m, 2H), 1.37 (s, 6H), 1.22 - 1.06 (m, 2H).

Reference： [1]Patent: WO2016/102672,2016,A2 .Location in patent: Page/Page column 220; 221; 222

30
[ 335592-60-4 ]
[ 22353-40-8 ]
tert-butyl (2-(4-(3-chloro-5-nitropyridin-2-yl)phenyl)propan-2-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.27 g	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; for 18h;Inert atmosphere; Reflux;	General procedure: Step 1: tert-butyl (trans- l-(4-(3-chloro-5-nitropyridin-2-yl)phenyl)-3-hydroxy-3- methylcyclobutyl)carbamate: A mixture of 2,3-dichloro-5-nitropyridine (383 mg, 1.98 mmol), iert-butyl (iraws-S-hydroxy-S-methyl- 1 -(4-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan- 2-yl)phenyl)cyclobutyl)carbamate (800 mg, 1.98 mmol, prepared according to Org.Process Res. Dev., 2012, 16, 1069) and ieirafc 5,-(triphenylphosphine)palladium(0) (229 mg, 0.198 mmol) in dioxane (10 ml) was treated with 2 M Na2C03(aq) (2.2 ml, 4.46 mmol). The vessel was purged with N2 and then heated at 75 C for 2 days. The reaction mixture was cooled and filtered through a glass microfibre filter, washing with MeCN, and concentrated in vacuo to afford a brown oil. The oil was partitioned between DCM (50 ml) and water (50 ml), filtered through a phase separation cartridge and the organic phase concentrated in vacuo. The residue was purified by column chromatography (40 g cartridge, 0-50% EtOAc/isohexane) to afford the title compound (501 mg, 1.05 mmol, 94%purity) as a yellow solid. LCMS (Method 1): m/z 378 (M+H-C4)+ at 2.25 min. 1H NMR (400 MHz, Chloroform-^ delta 9.40 (d, / = 2.3 Hz, 1H), 8.62 (d, / = 2.3 Hz, 1H), 7.86 - 7.78 (m, 2H), 7.61 - 7.54 (m, 2H), 5.11 (s, 1H), 2.82 - 2.52 (m, 4H), 1.63 (s, 3H), 1.43 (br s, 9H).

Reference： [1]Patent: WO2016/102672,2016,A2 .Location in patent: Page/Page column 102; 103; 104

31
[ 1173047-86-3 ]
[ 335592-60-4 ]

Reference： [1]Patent: WO2016/102672,2016,A2

32
[ 335592-60-4 ]
tert-butyl (2-(4-(5-amino-3-phenylpyridin-2-yl)phenyl)propan-2-yl)carbamate [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

33
[ 335592-60-4 ]
tert-butyl (2-(4-(5-(2-(trans-4-(N-methylacetamido)cyclohexyl)acetamido)-3-phenylpyridin-2-yl)phenyl)propan-2-yl)carbamate [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

34
[ 335592-60-4 ]
tert-butyl (2-(4-(5-nitro-3-(thiophen-3-yl)pyridin-2-yl)phenyl)propan-2-yl)carbamate [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

35
[ 335592-60-4 ]
benzyl (trans-4-(2-((6-(4-(2-((tert-butoxycarbonyl)amino)propan-2-yl)phenyl)-5-phenylpyridin-3-yl)amino)-2-oxoethyl)cyclohexyl)(methyl)carbamate [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

36
[ 335592-60-4 ]
tert-butyl (2-(4-(5-(2-(trans-4-(methylamino)cyclohexyl)acetamido)-3-phenylpyridin-2-yl)phenyl)propan-2-yl)carbamate [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

37
[ 335592-60-4 ]
tert-butyl (2-(4-(5-(2-(trans-4-(N-methylisobutyramido)cyclohexyl)acetamido)-3-phenylpyridin-2-yl)phenyl)propan-2-yl)carbamate [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

38
[ 335592-60-4 ]
N-(trans-4-(2-((6-(4-(2-aminopropan-2-yl)phenyl)-5-phenylpyridin-3-yl)amino)-2-oxoethyl)cyclohexyl)-N-methylisobutyramide [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

39
[ 335592-60-4 ]
tert-butyl (2-(4-(3-(2-fluorophenyl)-5-(2-(trans-4-(N-methylacetamido)cyclohexyl)acetamido)pyridin-2-yl)phenyl)propan-2-yl)carbamate [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

40
[ 335592-60-4 ]
N-(6-(4-(2-aminopropan-2-yl)phenyl)-5-(2-fluorophenyl)pyridin-3-yl)-2-(trans-4-(N-methylacetamido)cyclohexyl)acetamide [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

41
[ 335592-60-4 ]
C₄₁H₄₈N₄O₅ [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

42
[ 335592-60-4 ]
C₃₃H₄₂N₄O₃ [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

43
[ 335592-60-4 ]
C₃₇H₄₇ClN₄O₄ [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

44
[ 335592-60-4 ]
C₃₇H₄₆N₄O₄ [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

45
[ 335592-60-4 ]
N-(6-(4-(2-aminopropan-2-yl)phenyl)-5-phenylpyridin-3-yl)-2-(trans-4-(2-oxopiperidin-1-yl)cyclohexyl)acetamide [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

46
[ 335592-60-4 ]
tert-butyl (2-(4-(5-(2-(trans-4-(2-cyclopropylacetamido)cyclohexyl)acetamido)-3-phenylpyridin-2-yl)phenyl)propan-2-yl)carbamate [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

47
[ 335592-60-4 ]
N-(6-(4-(2-aminopropan-2-yl)phenyl)-5-phenylpyridin-3-yl)-2-(trans-4-(2-cyclopropylacetamido)cyclohexyl)acetamide [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

48
[ 335592-60-4 ]
methyl (trans-4-(2-((6-(4-(2-aminopropan-2-yl)phenyl)-5-phenylpyridin-3-yl)amino)-2-oxoethyl)cyclohexyl)(methyl)carbamate [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

49
[ 335592-60-4 ]
tert-butyl (2-(4-(3-(2-fluorophenyl)-5-nitropyridin-2-yl)phenyl)propan-2-yl)carbamate [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

50
[ 335592-60-4 ]
tert-butyl (2-(4-(5-amino-3-(2-fluorophenyl)pyridin-2-yl)phenyl)propan-2-yl)carbamate [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

51
[ 335592-60-4 ]
C₃₈H₄₈N₄O₄ [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

52
[ 335592-60-4 ]
C₃₆H₄₆N₄O₅ [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

53
[ 335592-60-4 ]
tert-butyl (2-(4-(5-(2-(trans-4-(2-oxooxazolidin-3-yl)cyclohexyl)acetamido)-3-phenylpyridin-2-yl)phenyl)propan-2-yl)carbamate [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

54
[ 335592-60-4 ]
N-(6-(4-(2-aminopropan-2-yl)phenyl)-5-phenylpyridin-3-yl)-2-(trans-4-(2-oxooxazolidin-3-yl)cyclohexyl)acetamide [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

55
[ 335592-60-4 ]
trans-methyl 4-(2-((6-(4-(2-((tert-butoxycarbonyl)amino)propan-2-yl)phenyl)-5-phenylpyridin-3-yl)amino)-2-oxoethyl)cyclohexanecarboxylate [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

56
[ 335592-60-4 ]
trans-4-(2-((6-(4-(2-((tert-butoxycarbonyl)amino)propan-2-yl)phenyl)-5-phenylpyridin-3-yl)amino)-2-oxoethyl)cyclohexanecarboxylic acid [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

57
[ 335592-60-4 ]
tert-butyl (2-(4-(5-(2-(trans-4-(dimethylcarbamoyl)cyclohexyl)acetamido)-3-phenylpyridin-2-yl)phenyl)propan-2-yl)carbamate [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

58
[ 335592-60-4 ]
trans-4-(2-((6-(4-(2-aminopropan-2-yl)phenyl)-5-phenylpyridin-3-yl)amino)-2-oxoethyl)-N,N-dimethylcyclohexanecarboxamide [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

59
[ 335592-60-4 ]
tert-butyl (2-(4-(6-amino-4-phenylpyridin-3-yl)phenyl)propan-2-yl)carbamate [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

60
[ 335592-60-4 ]
tert-butyl (2-(4-(6-(2-(trans-4-(N-methylacetamido)cyclohexyl)acetamido)-4-phenylpyridin-3-yl)phenyl)propan-2-yl)carbamate [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

61
[ 335592-60-4 ]
N-(5-(4-(2-aminopropan-2-yl)phenyl)-4-phenylpyridin-2-yl)-2-(trans-4-(N-methylacetamido)cyclohexyl)acetamide [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

62
[ 335592-60-4 ]
tert-butyl (2-(4-(6-(2-(trans-4-(2-oxooxazolidin-3-yl)cyclohexyl)acetamido)-4-phenylpyridin-3-yl)phenyl)propan-2-yl)carbamate [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

63
[ 335592-60-4 ]
N-(5-(4-(2-aminopropan-2-yl)phenyl)-4-phenylpyridin-2-yl)-2-(trans-4-(2-oxooxazolidin-3-yl)cyclohexyl)acetamide [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

64
[ 335592-60-4 ]
tert-butyl (2-(4-(5-nitro-3-phenylpyridin-2-yl)phenyl)propan-2-yl)carbamate [ No CAS ]

Reference： [1]Patent: WO2016/102672,2016,A2

65
[ 335592-60-4 ]
benzyl (5-bromo-4-phenylpyridin-2-yl)carbamate [ No CAS ]
benzyl (5-(4-(2-((tert-butoxycarbonyl)amino)propan-2-yl)phenyl)-4-phenylpyridin-2-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.62 g	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; for 18h;Inert atmosphere; Reflux;	General procedure: Step 1: tert-butyl (trans- l-(4-(3-chloro-5-nitropyridin-2-yl)phenyl)-3-hydroxy-3- methylcyclobutyl)carbamate: A mixture of 2,3-dichloro-5-nitropyridine (383 mg, 1.98 mmol), iert-butyl (iraws-S-hydroxy-S-methyl- 1 -(4-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan- 2-yl)phenyl)cyclobutyl)carbamate (800 mg, 1.98 mmol, prepared according to Org.Process Res. Dev., 2012, 16, 1069) and ieirafc 5,-(triphenylphosphine)palladium(0) (229 mg, 0.198 mmol) in dioxane (10 ml) was treated with 2 M Na2C03(aq) (2.2 ml, 4.46 mmol). The vessel was purged with N2 and then heated at 75 C for 2 days. The reaction mixture was cooled and filtered through a glass microfibre filter, washing with MeCN, and concentrated in vacuo to afford a brown oil. The oil was partitioned between DCM (50 ml) and water (50 ml), filtered through a phase separation cartridge and the organic phase concentrated in vacuo. The residue was purified by column chromatography (40 g cartridge, 0-50% EtOAc/isohexane) to afford the title compound (501 mg, 1.05 mmol, 94%purity) as a yellow solid. LCMS (Method 1): m/z 378 (M+H-C4)+ at 2.25 min. 1H NMR (400 MHz, Chloroform-^ delta 9.40 (d, / = 2.3 Hz, 1H), 8.62 (d, / = 2.3 Hz, 1H), 7.86 - 7.78 (m, 2H), 7.61 - 7.54 (m, 2H), 5.11 (s, 1H), 2.82 - 2.52 (m, 4H), 1.63 (s, 3H), 1.43 (br s, 9H).

Reference： [1]Patent: WO2016/102672,2016,A2 .Location in patent: Page/Page column 102; 103; 213

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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. 335592-60-4 ] {[proInfo.proName]}

Quality Control of [ 335592-60-4 ]

Related Doc. of [ 335592-60-4 ]

Product Details of [ 335592-60-4 ]

Safety of [ 335592-60-4 ]

Application In Synthesis of [ 335592-60-4 ]

[ 335592-60-4 ] Synthesis Path-Downstream 1~65

Precautionary Statements-General

Prevention

Response

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Physical hazards

Health hazards

Environmental hazards

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