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[ CAS No. 17654-70-5 ] {[proInfo.proName]}

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Product Details of [ 17654-70-5 ]

CAS No. :	17654-70-5	MDL No. :	MFCD19440215
Formula :	C₈H₂F₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UAKXPKOAUDLYKN-UHFFFAOYSA-N
M.W :	164.11	Pubchem ID :	11137466
Synonyms :

Safety of [ 17654-70-5 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 17654-70-5 ]

* 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 [ 17654-70-5 ]

[ 17654-70-5 ] Synthesis Path-Downstream 1~36

1
[ 28342-75-8 ]
[ 544-92-3 ]
[ 17654-70-5 ]

Reference： [1]Journal of Organic Chemistry,2002,vol. 67,p. 59 - 65

2
[ 17654-70-5 ]
[ 397299-94-4 ]

Yield	Reaction Conditions	Operation in experiment
67%	With diisobutylaluminium hydride In toluene at 0℃; for 1h;

Reference： [1]Nazarpack-Kandlousy, Noureddin; Nelen, Marina I.; Goral, Vasiliy; Eliseev, Alexey V. [Journal of Organic Chemistry, 2002, vol. 67, # 1, p. 59 - 65]

3
[ 17654-70-5 ]
C₂₄H₃₀N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 67 percent / DIBAL-H / toluene / 1 h / 0 °C 2.1: 97 percent / K₂CO₃ / dimethylformamide / 1 h / 20 °C 3.1: Ti(O-i-Pr)4 / CHCl₃ / 0.5 h / Heating 3.2: 45 percent / NaBH₃CN / methanol / 20 °C 4.1: 75 percent / PBr₃ / CH₂Cl₂; diethyl ether / 3 h / 20 °C 5.1: 95 percent / K₂CO₃ / dimethylsulfoxide / 2 h / 20 °C 6.1: 50 percent / N₂H₄*H₂O / 1,1,1-trideuterio-methanol; CDCl₃ / 12 h / 20 °C

Reference： [1]Nazarpack-Kandlousy, Noureddin; Nelen, Marina I.; Goral, Vasiliy; Eliseev, Alexey V. [Journal of Organic Chemistry, 2002, vol. 67, # 1, p. 59 - 65]

4
[ 17654-70-5 ]
[ 397300-00-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 67 percent / DIBAL-H / toluene / 1 h / 0 °C 2: 97 percent / K₂CO₃ / dimethylformamide / 1 h / 20 °C

Reference： [1]Nazarpack-Kandlousy, Noureddin; Nelen, Marina I.; Goral, Vasiliy; Eliseev, Alexey V. [Journal of Organic Chemistry, 2002, vol. 67, # 1, p. 59 - 65]

5
[ 17654-70-5 ]
[ 397300-10-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 67 percent / DIBAL-H / toluene / 1 h / 0 °C 2.1: 97 percent / K₂CO₃ / dimethylformamide / 1 h / 20 °C 3.1: Ti(O-i-Pr)4 / CHCl₃ / 0.5 h / Heating 3.2: 45 percent / NaBH₃CN / methanol / 20 °C 4.1: 75 percent / PBr₃ / CH₂Cl₂; diethyl ether / 3 h / 20 °C

Reference： [1]Nazarpack-Kandlousy, Noureddin; Nelen, Marina I.; Goral, Vasiliy; Eliseev, Alexey V. [Journal of Organic Chemistry, 2002, vol. 67, # 1, p. 59 - 65]

6
[ 17654-70-5 ]
[ 397300-06-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 67 percent / DIBAL-H / toluene / 1 h / 0 °C 2.1: 97 percent / K₂CO₃ / dimethylformamide / 1 h / 20 °C 3.1: Ti(O-i-Pr)4 / CHCl₃ / 0.5 h / Heating 3.2: 45 percent / NaBH₃CN / methanol / 20 °C

Reference： [1]Nazarpack-Kandlousy, Noureddin; Nelen, Marina I.; Goral, Vasiliy; Eliseev, Alexey V. [Journal of Organic Chemistry, 2002, vol. 67, # 1, p. 59 - 65]

7
[ 17654-70-5 ]
[ 397300-14-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 67 percent / DIBAL-H / toluene / 1 h / 0 °C 2.1: 97 percent / K₂CO₃ / dimethylformamide / 1 h / 20 °C 3.1: Ti(O-i-Pr)4 / CHCl₃ / 0.5 h / Heating 3.2: 45 percent / NaBH₃CN / methanol / 20 °C 4.1: 75 percent / PBr₃ / CH₂Cl₂; diethyl ether / 3 h / 20 °C 5.1: 95 percent / K₂CO₃ / dimethylsulfoxide / 2 h / 20 °C

Reference： [1]Nazarpack-Kandlousy, Noureddin; Nelen, Marina I.; Goral, Vasiliy; Eliseev, Alexey V. [Journal of Organic Chemistry, 2002, vol. 67, # 1, p. 59 - 65]

8
[ 86-74-8 ]
[ 17654-70-5 ]
4,6-di-(9H-carbazol-9-yl)isophthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 2h;	2 Synthesis of 4,6-di(9H-carbazol-9-yl)isophthalonitrile (Ref. 1). A mixture of carbazole (0406) (0.50 g, 3.05 mmol), 4,6-difluoroisophthalonitrile (1.53 g, 9.14 mmol), and potassium carbonate (1.69 g, 12.2 mmol) in 10 mL of N, A -di methylformami de (DMF) was stirred at 110 °C under ambient atmosphere for 2 h. The reaction mixture was poured into MeOH to afford yellow precipitation. After filtration, the resulting solid was washed with MeOH to give a yellow cake. The mixture was purified on silica gel column chromatography using 5: 1 (v/v) chloroform/hexane as eluent to give yellowish green solid (1.02 g) in 73.0% yield. NMR (500 MHz, CDCb, d): 8.49 (s, 1H), 8.14 (d, J= 7.0 Hz, 4H), 7.97 (s, 1H), 7.49 (t, J= 8.0 Hz, 4H), 7.40-7.36 (m, 8H).
	With sodium hydride In tetrahydrofuran
2.3 g	Stage #1: 9H-carbazole With sodium hydride In tetrahydrofuran; paraffin oil for 0.5h; Stage #2: 4,6-difluoro-1,3-benzenedicyanide In tetrahydrofuran; paraffin oil at 20℃; for 2h;	1.2 Synthesis of Intermediate 2 Containing 60% content in paraffin oilSodium hydride (0.9 g, 24.3 mmol) was washed with normal nucleic acid,A solution of carbazole (3.1 g, 18.2 mmol) in THF (tetrahydrofuran) at a concentration of 1 M is placed in sodium hydride.After stirring for 30 minutes, once all of the sodium hydride is dissolved, slowly add Intermediate 1 (1.0 g, 6.1 mmol) to a solution of 1 M in THF.After stirring at room temperature for 2 hours,The reaction is terminated by pouring methanol or distilled water.The reaction product was extracted with MC and subjected to column chromatography using a mixed solvent of chloroform / hexane to obtain 2.3 g of Intermediate 2.

Reference： [1]Current Patent Assignee: KYULUX, INC.; YANG YU SEOK - WO2019/195104, 2019, A1 Location in patent: Page/Page column 90-91
[2]Cho, Yong Joo; Jeon, Sang Kyu; Chin, Byung Doo; Yu, Eunsun; Lee, Jun Yeob [Angewandte Chemie - International Edition, 2015, vol. 54, # 17, p. 5201 - 5204][Angew. Chem., 2015, vol. 127, # 17, p. 5290 - 5293,4]
[3]Current Patent Assignee: SAMSUNG C&T CORPORATION; SAMSUNG SDI CO.,LTD.; DANKOOK UNIVERSITY - KR2016/331, 2016, A Location in patent: Paragraph 0145; 0157-0161

9
[ 86-74-8 ]
[ 17654-70-5 ]
4-(9H-carbazol-9-yl)-6-fluoroisophthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With sodium hydride In N,N-dimethyl-formamide for 10h; Reflux;	1 Intermediate 1-1 (4.31 g, 26.31 mmol), 9H-carbazole (4.4 g, 26.31 mmol), Sodium hydride (0.7 g, 28.94 mmol) was added to 90 ml of dimethylformamide, and the mixture was heated and stirred. Intermediate 1-1 (4.31 g, 26.31 mmol), 9H-carbazole (4.4 g, 26.31 mmol)Sodium hydride (0.7 g, 28.94 mmol) was added to 90 ml of dimethylformamide, and the mixture was heated and stirred.
37%	Stage #1: 9H-carbazole With sodium hydride In tetrahydrofuran; mineral oil for 0.166667h; Inert atmosphere; Stage #2: 4,6-difluoro-1,3-benzenedicyanide In tetrahydrofuran; mineral oil at 0℃; for 10h; Inert atmosphere;
37%	Stage #1: 9H-carbazole With sodium hydride In tetrahydrofuran Stage #2: 4,6-difluoro-1,3-benzenedicyanide In tetrahydrofuran; hexane at 20℃; for 10h;	Synthesis of Intermediate 1-2 Sodium hydride (0.29 g, 7.2 mmol) was three times washed with hexane and dried udder vacuum for 2 hours. Subsequently, tetrahydroffiran (30 ml) was added thereto, and 30 minutes later, 9H-carbazole (1 g, 6.0 mmol) was added thereto. Afier minutes, Intermediate 1-1 (0.98 g, 6.0 mmol) was added thereto. The solution was stirred at room temperature for 10 hours and then, treated with magnesium sulfate by using dichioromethane to remove moisture and wet-purified through a column to obtain Intermediate 1-2 (0.7 g). A yield was 37%.

Stage #1: 9H-carbazole With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: 4,6-difluoro-1,3-benzenedicyanide In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;

1.3 Step 3. Synthesis of peripheral branch R1-3OHCz Add carbazole (3.1g, 17mmol), NaH (5.35g, 23mmol), THF (15mL) to the reaction flask, stir the reaction at room temperature for 1h, and then add 4,6-difluoro-1,3-benzenedicyanide ( 4.18g, 25.5mmol), reacted at room temperature under nitrogen protection for 24h. After the reaction is over, add water to precipitate, and then extract with dichloromethane. Purified by column chromatography, the intermediate product 4-(9hydro-carbazol-9-yl)-6-fluorobenzene-1,3-dinitrile containing a carbazole is obtained. Similarly, the intermediate product was reacted with 3-methoxycarbazole in a molar ratio of 1:1.5. After the reaction, R1-3OCH3Cz was obtained, which was dissolved in a reaction flask containing 20mL of dichloromethane, and then filled with 30mL Add 15 mL of 3-bromide to the separatory funnel of the dichloromethane solution, add it dropwise to the reaction flask under ice bath conditions, stir the reaction at 0°C for 4h, quench with methanol solution (20mL), The pH of the mixed solution was adjusted to be neutral by washing with sodium hydrogen, and finally the TADF branched chain R1-3OHCz was obtained by extraction and filtration, with a yield of 65%.

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD.; SUNGKYUNKWAN UNIVERSITY - KR2020/11027, 2020, A Location in patent: Paragraph 0274; 0275; 0277
[2]Kim, Mounggon; Jeon, Sang Kyu; Hwang, Seok-Ho; Lee, Sang-Shin; Yu, Eunsun; Lee, Jun Yeob [Chemical Communications, 2016, vol. 52, # 2, p. 339 - 342]
[3]Current Patent Assignee: SAMSUNG SDI CO.,LTD. - US2018/291264, 2018, A1 Location in patent: Paragraph 0129; 0130
[4]Current Patent Assignee: SOUTHEAST UNIVERSITY - CN113336694, 2021, A Location in patent: Paragraph 0048; 0053; 0054; 0062

10
[ 17654-70-5 ]
6,6'-(9H,9'H-[3,3'-bicarbazole]-9,9'-diyl)bis(4-(9H-carbazol-9-yl)isophthalonitrile) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / Inert atmosphere 1.2: 10 h / 0 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / Inert atmosphere 2.2: 10 h / Inert atmosphere
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran 1.2: 10 h / 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.17 h 2.2: 10 h / 20 °C

Reference： [1]Kim, Mounggon; Jeon, Sang Kyu; Hwang, Seok-Ho; Lee, Sang-Shin; Yu, Eunsun; Lee, Jun Yeob [Chemical Communications, 2016, vol. 52, # 2, p. 339 - 342]
[2]Current Patent Assignee: SAMSUNG SDI CO.,LTD. - US2018/291264, 2018, A1

11
[ 17654-70-5 ]
6,6'-(9H,9'H-[3,4'-bicarbazole]-9,9'-diyl)bis(4-(9H-carbazol-9-yl)isophthalonitrile) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / Inert atmosphere 1.2: 10 h / 0 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / Inert atmosphere 2.2: 10 h / Inert atmosphere
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran 1.2: 10 h / 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.17 h 2.2: 10 h / 20 °C

Reference： [1]Kim, Mounggon; Jeon, Sang Kyu; Hwang, Seok-Ho; Lee, Sang-Shin; Yu, Eunsun; Lee, Jun Yeob [Chemical Communications, 2016, vol. 52, # 2, p. 339 - 342]
[2]Current Patent Assignee: SAMSUNG SDI CO.,LTD. - US2018/291264, 2018, A1

12
[ 28342-75-8 ]
copper(l) cyanide [ No CAS ]
[ 17654-70-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	In N,N-dimethyl-formamide; for 14h;Inert atmosphere; Reflux;	<strong>[28342-75-8]1,5-dibromo-2,4-difluorobenzene</strong> (5 g, 18.4 mmol) and copper (I) cyanide (CuCN) (4.9 g, 55.2 mmol) were added to dimethylformamide (90 ml), and the mixture was stirred under a nitrogen flow. Subsequently, the solution was heated up, refluxed and stirred for 14 hours, cooled down to room temperature, and filtered, and the filtered solution was treated with magnesium sulfate by using dichloromethane to remove moisture and purified through a column to obtain Intermediate 1-1 (2.4 g). A yield was 80percent.
6 g	In N,N-dimethyl-formamide; for 17h;Reflux; Inert atmosphere;	<strong>[28342-75-8]1,5-dibromo-2,4-difluorobenzene</strong>(30 g, 110.3 mmol)And cyanocopper(22.7 g, 253.7 mmol)After dissolving in DMF (120 ml), it was made into nitrogen atmosphere, and the temperature was raised, and the mixture was refluxed with stirring for 17 hours.The reaction solution was extracted with MC and then subjected to column chromatography using an ethyl acetate / hexane mixed solvent as eluent to obtain 6.0 g of Intermediate 1.

Reference： [1]Patent: US2018/291264,2018,A1 .Location in patent: Paragraph 0127; 0128
[2]Patent: KR2016/331,2016,A .Location in patent: Paragraph 0145; 0152-0155

13
[ 18628-07-4 ]
[ 17654-70-5 ]
4,6-di(9H-[3,9'-bicarbazol]-9-yl)isophthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%		General procedure: Sodium hydride (60% in oil, 0.16 g, 3.98 mmol) and 9H-3,9'-bicarbazole (0.85 g, 2.53 mmol) were stirred in 3 ml anhydrousDMF solvent under a nitrogen atmosphere. After 20 min, 4,5-difluorophthalonitrile (0.20 g, 1.21 mmol) in 5 ml DMF was addedthe mixture. The reaction mixture was stirred at room temperaturefor 1 h. The reaction mixture was quenched with distilled water.Organic layer of the mixture was extracted with dichloromethaneand distilled water. Then solvent of organic layer was evaporatedand purified by column chromatography (dichloromethane/nhexane).

Reference： [1]Organic electronics,2017,vol. 42,p. 337 - 342

14
5,13-dihydro-5,5-dimethylbenzofuran[3,2-c]acridine [ No CAS ]
[ 17654-70-5 ]
C₅₀H₃₄N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: 5,13-dihydro-5,5-dimethylbenzofuran[3,2-c]acridine With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: 4,6-difluoro-isophthalonitrile In tetrahydrofuran at 20℃; for 5h; Inert atmosphere;	1 Based on the reaction expression 1, a first compound is synthesized which has a molecular structure expressed as a chemical formula of a product in the reaction expression 1 (corresponding to the above chemical formula7).Specifically, a sodium hydride (60% in paraffin, 0.24 g, 9.70 mmol) is washed using a nucleic acid to remove a paraffin oil. Under a nitrogen gas stream, a furan derivative acridine (1.56 g, 5.24 mmol) dissolved in tetrahydrofuran is slowly added dropwise to the purified sodium hydride. Then, the mixture has been stirred for about 30 minutes at a room temperature to acquire a first product.Then, 4,6-difluoroisophthalonitrile (0.4 g, 2.43 mmol) is dissolved in tetrahydrofuran to acquire a second mixture which in turn is added slowly to the first product, and is agitated for about 5 hours at a room temperature, to acquire a second product.Subsequently, water and alcohol are added to the second product to terminate the reaction. A target product is extracted using distilled water and methylene chloride. The moisture remaining in the target product is removed using magnesium sulfate. Then, the target product is subjected to the polar column chromatography using a mixture solvent of acetone and n-nucleic acid, to acquire the first compound 1.1 g. Finally, a pure yellow powder of the first compound is obtained through a final purification by sublimation by about 0.9 g (62% yield).The final product has a following mass analysis (LC-Mass) m/z 722.85 [(M)+]. 1H NMR (400 MHZ, DMSO): δ 9.15 (s, 1H), 8.52 (s, 1H), 8.10-8.08 (d, 2H, J=4.00 Hz), 7.77-7.75 (d, 2H, J=2.00 Hz), 7.64-7.62 (m, 2H), 7.57-7.51 (m, 4H), 7.42-7.37 (m, 4H), 6.93-6.89 (t, 2H, J=5.33 Hz), 6.54-6.5 (t, 2H, J=5.33 Hz), 6.47-6.45 (d, 2H, J=4.00 Hz) 13C NMR (100 MHZ, CDCl3): δ 156.52, 150.37, 145.05, 137.71, 135.53, 134.87, 132.13, 124.85, 123.74, 121.80, 120.92, 118.78, 115.81, 11.52.

Reference： [1]Current Patent Assignee: SUNGKYUNKWAN UNIVERSITY - US2017/98779, 2017, A1 Location in patent: Paragraph 0035-0040

15
[ 1583-58-0 ]
[ 17654-70-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: N,N-dimethyl-formamide; thionyl chloride / tetrahydrofuran / 5 h / Reflux 2.1: ammonium hydroxide / 1.5 h / -10 - 20 °C 3.1: trichlorophosphate / N,N-dimethyl-formamide / 7.5 h / -15 - 20 °C 4.1: sulfuric acid; nitric acid / 1.5 h / -10 - 20 °C 5.1: acetic acid; iron / ethanol / 4 h / 20 - 50 °C 6.1: sodium nitrite / water / 1 h / -10 °C 6.2: 1 h 7.1: zinc(II) cyanide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 10.5 h / 20 - 120 °C

Reference： [1]Current Patent Assignee: GUIZHOU UNIVERSITY - CN106854165, 2017, A

16
[ 72482-64-5 ]
[ 17654-70-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: ammonium hydroxide / 1.5 h / -10 - 20 °C 2.1: trichlorophosphate / N,N-dimethyl-formamide / 7.5 h / -15 - 20 °C 3.1: sulfuric acid; nitric acid / 1.5 h / -10 - 20 °C 4.1: acetic acid; iron / ethanol / 4 h / 20 - 50 °C 5.1: sodium nitrite / water / 1 h / -10 °C 5.2: 1 h 6.1: zinc(II) cyanide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 10.5 h / 20 - 120 °C

Reference： [1]Current Patent Assignee: GUIZHOU UNIVERSITY - CN106854165, 2017, A

17
[ 85118-02-1 ]
[ 17654-70-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: trichlorophosphate / N,N-dimethyl-formamide / 7.5 h / -15 - 20 °C 2.1: sulfuric acid; nitric acid / 1.5 h / -10 - 20 °C 3.1: acetic acid; iron / ethanol / 4 h / 20 - 50 °C 4.1: sodium nitrite / water / 1 h / -10 °C 4.2: 1 h 5.1: zinc(II) cyanide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 10.5 h / 20 - 120 °C

Reference： [1]Current Patent Assignee: GUIZHOU UNIVERSITY - CN106854165, 2017, A

18
[ 3939-09-1 ]
[ 17654-70-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: sulfuric acid; nitric acid / 1.5 h / -10 - 20 °C 2.1: acetic acid; iron / ethanol / 4 h / 20 - 50 °C 3.1: sodium nitrite / water / 1 h / -10 °C 3.2: 1 h 4.1: zinc(II) cyanide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 10.5 h / 20 - 120 °C

Reference： [1]Current Patent Assignee: GUIZHOU UNIVERSITY - CN106854165, 2017, A

19
[ 67152-20-9 ]
[ 17654-70-5 ]

Reference： [1]Patent: CN106854165,2017,A

20
[ 952285-54-0 ]
[ 17654-70-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium nitrite / water / 1 h / -10 °C 1.2: 1 h 2.1: zinc(II) cyanide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 10.5 h / 20 - 120 °C

Reference： [1]Current Patent Assignee: GUIZHOU UNIVERSITY - CN106854165, 2017, A

21
2,4-difluoro-5-iodobenzonitrile [ No CAS ]
[ 17654-70-5 ]

Yield	Reaction Conditions	Operation in experiment
71.9%	With zinc(II) cyanide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ In N,N-dimethyl-formamide at 20 - 120℃; for 10.5h;	6.G Preparation of G.4,6 - difluoroisophthalonitrile In a 100 mL single-necked flask, 2,4-difluoro-5-iodobenzonitrile (11.5 g, 43.3 mmol)Was dissolved in N, N-dimethylformamide (50 ml), zinc cyanide (3.1 g, 26.0 mmol) and tetrakis (triphenylphosphine) palladium (2.7 g, 2.2 mmol) were added and reacted at room temperature for 0.5 h,120 ° C for 10 h. Reaction is completed, while the hot filter,The filtrate into the ice water that is solid precipitation, suction filtration,The filter cake was beaten with a small amount of n-hexane (3 mL) and the target product was filtered4,6-difluoroisophthalonitrile (5.1 g) in a yield of 71.9%.

Reference： [1]Current Patent Assignee: GUIZHOU UNIVERSITY - CN106854165, 2017, A Location in patent: Paragraph 0112; 0113; 0144; 0145

22
[ 17654-70-5 ]
6,6'-(9H,9'H-[4,4'-bicarbazole]-9,9'-diyl)bis(4-(9H-carbazol-9-yl)isophthalonitrile) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran 1.2: 10 h / 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.17 h 2.2: 10 h / 20 °C

Reference： [1]Current Patent Assignee: SAMSUNG SDI CO.,LTD. - US2018/291264, 2018, A1

23
[ 86-74-8 ]
[ 17654-70-5 ]
3,5-di(9H-carbazol-9-yl)-[1,1'-biphenyl]-2,6-dicarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 110 °C 2: potassium carbonate; palladium diacetate; tricyclohexylphosphine; 2-Ethylhexanoic acid / 5,5-dimethyl-1,3-cyclohexadiene / 24.25 h / 20 - 100 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: KYULUX, INC.; YANG YU SEOK - WO2019/195104, 2019, A1

24
[ 17654-70-5 ]
3',5'-di(9H-carbazol-9-yl)-[1,1':4',1''-terphenyl]-2',6'-dicarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium carbonate; palladium diacetate; tricyclohexylphosphine; 2-Ethylhexanoic acid / 5,5-dimethyl-1,3-cyclohexadiene / 20 - 100 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 20 °C / Inert atmosphere 2.2: 1 h / 20 °C

Reference： [1]Current Patent Assignee: KYULUX, INC.; YANG YU SEOK - WO2019/195104, 2019, A1

25
[ 17654-70-5 ]
3',5'-bis(3,6-di-tert-butyl-9H-carbazol-9-yl)-[1,1':4',1''-terphenyl]-2',6'-dicarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium carbonate; palladium diacetate; tricyclohexylphosphine; 2-Ethylhexanoic acid / 5,5-dimethyl-1,3-cyclohexadiene / 20 - 100 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 20 °C / Inert atmosphere 2.2: 2 h / 20 °C

Reference： [1]Current Patent Assignee: KYULUX, INC.; YANG YU SEOK - WO2019/195104, 2019, A1

26
[ 108-86-1 ]
[ 17654-70-5 ]
2,6-difluoro-[1,1'-biphenyl]-3,5-dicarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30.7%	With 2-Ethylhexanoic acid; palladium diacetate; potassium carbonate; tricyclohexylphosphine In 5,5-dimethyl-1,3-cyclohexadiene at 20 - 100℃; for 5.25h; Inert atmosphere;	2 Synthesis of 2,6-difluoro-[l,l'-biphenyl]-3,5-dicarbonitrile. A doubled-necked flask equipped with a stir bar was charged with 4,6-difluoroisophthalonitrile (0.50 g, 3.05 mmol), potassium carbonate (0.63 g, 4.57 mmol), palladium acetate (22 mg, 0.091 mmol) and tricyclohexylphosphine (78.4 mg, 0.274 mmol), which was evacuated and refilled with nitrogen for three times. The reaction mixture was added bromobenzene (0.64 mL, 6.09 mmol), 2-ethylhexanoic acid (0.05 mL, 0.305 mmol), and xylene (10 mL) and was stirred at room temperature for 15 min, then heated to 100 °C while stirring for 5 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (10 mL) and water (10 mL), and filtered through Celite pad followed by washing with ethyl acetate. The aqueous layer was separated and extracted with ethyl acetate (20 mL). The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solvents were evaporated under vacuum, and the crude product was purified by silica gel column chromatography using 1 : 1 : 1 (v/v/v) hexane/toluene/CHCb as eluent to afford white solid (0.22 g, 30.7%). NMR (500 MHz, CDCb, d): 7.95 (t, J = 6.5 Hz, 1H), 7.56-7.53 (m, 3H), 7.43-7.41 (m, 2H).

Reference： [1]Current Patent Assignee: KYULUX, INC.; YANG YU SEOK - WO2019/195104, 2019, A1 Location in patent: Page/Page column 91-92

27
[ 108-86-1 ]
[ 17654-70-5 ]
2,6-di(9H-carbazol-9-yl)-[1,1'-biphenyl]-3,5-dicarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium carbonate; palladium diacetate; tricyclohexylphosphine; 2-Ethylhexanoic acid / 5,5-dimethyl-1,3-cyclohexadiene / 5.25 h / 20 - 100 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 20 °C / Inert atmosphere 2.2: 2 h / 20 °C

Reference： [1]Current Patent Assignee: KYULUX, INC.; YANG YU SEOK - WO2019/195104, 2019, A1

28
[ 108-86-1 ]
[ 17654-70-5 ]
3',5'-difluoro-[1,1':4',1''-terphenyl]-2',6'-dicarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43.1%	With 2-Ethylhexanoic acid; palladium diacetate; potassium carbonate; tricyclohexylphosphine In 5,5-dimethyl-1,3-cyclohexadiene at 20 - 100℃; Inert atmosphere;	2 Synthesis of 3',5'-difluoro-[l,l':4',l"-terphenyl]-2',6'-dicarbonitrile. A doubled- necked flask equipped with a stir bar was charged with 4,6-difluoroisophthalonitrile (0.50 g, 3.05 mmol), potassium carbonate (0.63 g, 4.57 mmol), palladium acetate (22 mg, 0.091 mmol) and tricyclohexylphosphine (78.4 mg, 0.274 mmol), which was evacuated and refilled with nitrogen for three times. The reaction mixture was added bromobenzene (0.64 mL, 6.09 mmol), 2-ethylhexanoic acid (0.05 mL, 0.305 mmol), and xylene (10 mL) and was stirred at room temperature for 15 min, then heated to 100 °C. To fully convert the reaction, additional bromobenzene (0.80 mL, 7.62 mmol) was added in 5 portions every half an hour. After stirring for 24 h, the reaction mixture was cooled to room temperature, diluted with CHCb (10 mL) and water (10 mL), and filtered through Celite pad followed by washing with CHCb. The aqueous layer was separated and extracted with CHCb (20 mL). The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solvents were evaporated under vacuum, and the crude product was purified by silica gel column chromatography using 1 : 1 :2 (v/v/v) hexane/toluene/CHCb as eluent to afford white solid (0.42 g, 43.1%). 'H NMR (500 MHz, (0423) CDCb, d): 7.62-7.54 (m, 8H), 7.49-7.47 (m, 2H).

Reference： [1]Current Patent Assignee: KYULUX, INC.; YANG YU SEOK - WO2019/195104, 2019, A1 Location in patent: Page/Page column 93

29
2-fluoro-9,9-dimethylacridine [ No CAS ]
[ 17654-70-5 ]
C₃₈H₂₈F₂N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: 2-fluoro-9,9-dimethylacridine With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Inert atmosphere; Reflux; Stage #2: 4,6-difluoro-1,3-benzenedicyanide In tetrahydrofuran; mineral oil at 60℃; for 24h; Inert atmosphere;	3 And the specific synthetic steps are: Add 2-fluoro-9,9-dimethylacridine (2.73g, 12mmol), 70% oil-dispersed sodium hydride (0.42 g, 12 mmol) and 20 mL of tetrahydrofuran were added to a 50 mL single-neck round bottom flask. After refluxing for 30 minutes under the protection of argon, 4,6-difluoro-m-cyanobenzene (0.82 g, 5 mmol) was added, and then refluxed at 60 ° C for 24 hours. Quenched with saturated brine, extracted with dichloromethane, and dried the organic phase over anhydrous sodium sulfate. Filter and spin dry. The product was passed through a column with a volume ratio of n-hexane: methylene chloride of 1: 1 to obtain 2.05 g of a product. Light yellow solid, 71% yield.

Reference： [1]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - CN110272387, 2019, A Location in patent: Paragraph 0051-0052

30
[ 243-28-7 ]
[ 17654-70-5 ]
C₂₄H₁₂FN₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium hydride; In N,N-dimethyl-formamide; for 10h;Heating;	4,6-difluoroisonaphthalonitrile (10 g, 60.97 mmol),5H-benzo [b] carbazole (13.24 g, 60.97 mmol) and sodium hydride (1.61 g, 67.06 mmol) are added to 180 ml of dimethylformamide, and the mixture is heated and stirred. After 8 hours, the reaction was completed, the temperature was lowered to room temperature, concentrated under reduced pressure, and column purified to prepare 14.53 g (yield 66%) of intermediate 2-1.

Reference： [1]Patent: KR2020/11027,2020,A .Location in patent: Paragraph 0281-0283

31
[ 17654-70-5 ]
C₆₈H₄₀N₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide / 10 h / Reflux 2: sodium hydride / N,N-dimethyl-formamide / 13 h / Heating

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD.; SUNGKYUNKWAN UNIVERSITY - KR2020/11027, 2020, A

32
[ 17654-70-5 ]
C₅₀H₂₉N₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide / 10 h / Reflux 2: sodium hydride / N,N-dimethyl-formamide / 10 h / Heating

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD.; SUNGKYUNKWAN UNIVERSITY - KR2020/11027, 2020, A

33
[ 17654-70-5 ]
C₅₄H₃₁N₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide / 10 h / Heating 2: sodium hydride / N,N-dimethyl-formamide / 10 h / Heating

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD.; SUNGKYUNKWAN UNIVERSITY - KR2020/11027, 2020, A

34
[ 17654-70-5 ]
6,6'-(1,3-phenylenebis(oxy))bis(4-phenoxyisophthalonitrile) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate / 1-methyl-pyrrolidin-2-one / 13 h / 140 °C 2: caesium carbonate / 1-methyl-pyrrolidin-2-one / 13 h / 140 °C

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - CN113264953, 2021, A

35
[ 17654-70-5 ]
C₃₄H₁₂B₂N₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate / 1-methyl-pyrrolidin-2-one / 13 h / 140 °C 2: caesium carbonate / 1-methyl-pyrrolidin-2-one / 13 h / 140 °C 3: o-xylene / 24 h / 150 °C

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - CN113264953, 2021, A

36
[ 17654-70-5 ]
[ 108-46-3 ]
6,6'-(1,3-phenylenebis(oxy))bis(4-fluoroisophthalonitrile) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With caesium carbonate In 1-methyl-pyrrolidin-2-one at 140℃; for 13h;	4 4,6-Difluoroisophthalonitrile (5.8g),Resorcinol (3.10g, 29mM),Cs2CO3 (10.0g) and NMP (300mL) are added to the flask,And the mixed solution was stirred at a temperature of 140°C for 13 hours.Cool the reaction solution to room temperature,And perform column separation to obtain 3.4 g of intermediate compound 12-1(6,6'-(1,3-phenylenebis(oxy))bis(4-fluoroisophthalonitrile)) (Yield: 60%).

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - CN113264953, 2021, A Location in patent: Paragraph 0552-0555

Same Skeleton Products

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Ghs Precautionary Statements

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

Ghs Hazard Statements

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