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[ CAS No. 89281-13-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

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2D 3D

Chemical Structure| 89281-13-0

Chemical Structure| 89281-13-0

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Quality Control of [ 89281-13-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 89281-13-0 ]

SDS Specification

Alternatived Products of [ 89281-13-0 ]

Product Details of [ 89281-13-0 ]

CAS No. :	89281-13-0	MDL No. :	MFCD00052640
Formula :	C₆H₄Cl₂N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CFYBBFGXTQBLQV-UHFFFAOYSA-N
M.W :	191.02	Pubchem ID :	2781802
Synonyms :

Safety of [ 89281-13-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 89281-13-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 89281-13-0 ]
Downstream synthetic route of [ 89281-13-0 ]

[ 89281-13-0 ] Synthesis Path-Upstream 1~3

1
[ 89281-13-0 ]
[ 32710-65-9 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1929, vol. 48, p. 468,471
[2] Recueil des Travaux Chimiques des Pays-Bas, 1933, vol. 52, p. 55,59

2
[ 89281-13-0 ]
[ 88579-63-9 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1933, vol. 52, p. 55,59

3
[ 89281-13-0 ]
[ 101990-69-6 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1933, vol. 52, p. 55,59

[ 89281-13-0 ] Synthesis Path-Downstream 1~52

1
[ 89281-13-0 ]
[ 32710-65-9 ]

Yield	Reaction Conditions	Operation in experiment
15 g	With triethylamine; trifluoroacetic anhydride; In 1,4-dioxane; at 90℃;Inert atmosphere;	In a reaction flask, 19 g of 2,6-dichloro-4-carboxamide pyridine was added to 200 mL of 1,4-dioxane, and then 42 g of trifluoroacetic anhydride and 20 g of triethylamine were added, and heated under nitrogen atmosphere. After 90 C, TLC monitoring the reaction of the starting material was completed, the reaction solution was cooled to room temperature, and then water was added to 100 mL, and the reaction mixture was extracted with 100 mL of ethyl acetate. The organic phase was combined, dried over anhydrous magnesium sulfate and concentrated.2,6-dichloro-4-carbonitrile-pyridine 15g

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1929,vol. 48,p. 468,471
[2]Recueil des Travaux Chimiques des Pays-Bas,1933,vol. 52,p. 55,59
[3]Patent: CN109053805,2018,A .Location in patent: Paragraph 0039; 0040; 0041

2
[ 1569-69-3 ]
[ 89281-13-0 ]
2,6-Bis-cyclohexylsulfanyl-isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium methylate In N,N-dimethyl-formamide at 50℃;

Reference： [1]Miletin; Hartl; Odlerova; Machacek [Pharmazie, 1997, vol. 52, # 7, p. 558 - 560]

3
[ 107-03-9 ]
[ 89281-13-0 ]
2,6-Bis-propylsulfanyl-isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium methylate In N,N-dimethyl-formamide at 50℃;

Reference： [1]Miletin; Hartl; Odlerova; Machacek [Pharmazie, 1997, vol. 52, # 7, p. 558 - 560]

4
[ 109-79-5 ]
[ 89281-13-0 ]
2,6-Bis-butylsulfanyl-isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With sodium methylate In N,N-dimethyl-formamide at 50℃;

Reference： [1]Miletin; Hartl; Odlerova; Machacek [Pharmazie, 1997, vol. 52, # 7, p. 558 - 560]

5
[ 110-66-7 ]
[ 89281-13-0 ]
2,6-Bis-pentylsulfanyl-isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With sodium methylate In N,N-dimethyl-formamide at 50℃;

Reference： [1]Miletin; Hartl; Odlerova; Machacek [Pharmazie, 1997, vol. 52, # 7, p. 558 - 560]

6
[ 111-31-9 ]
[ 89281-13-0 ]
2,6-Bis-hexylsulfanyl-isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium methylate In N,N-dimethyl-formamide at 50℃;

Reference： [1]Miletin; Hartl; Odlerova; Machacek [Pharmazie, 1997, vol. 52, # 7, p. 558 - 560]

7
[ 1639-09-4 ]
[ 89281-13-0 ]
2,6-Bis-heptylsulfanyl-isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium methylate In N,N-dimethyl-formamide at 50℃;

Reference： [1]Miletin; Hartl; Odlerova; Machacek [Pharmazie, 1997, vol. 52, # 7, p. 558 - 560]

8
[ 111-88-6 ]
[ 89281-13-0 ]
2,6-Bis-octylsulfanyl-isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium methylate In N,N-dimethyl-formamide at 50℃;

Reference： [1]Miletin; Hartl; Odlerova; Machacek [Pharmazie, 1997, vol. 52, # 7, p. 558 - 560]

9
[ 89281-13-0 ]
[ 5188-07-8 ]
2,6-bis(methylthio)-4-pyridinecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In N,N-dimethyl-formamide at 50℃;

Reference： [1]Miletin; Hartl; Odlerova; Machacek [Pharmazie, 1997, vol. 52, # 7, p. 558 - 560]

10
[ 89281-13-0 ]
[ 75-08-1 ]
2,6-Bis-ethylsulfanyl-isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With sodium methylate In N,N-dimethyl-formamide at 50℃;

Reference： [1]Miletin; Hartl; Odlerova; Machacek [Pharmazie, 1997, vol. 52, # 7, p. 558 - 560]

11
[ 50-00-0 ]
[ 873-55-2 ]
[ 89281-13-0 ]
N-(benzenesulphonylmethyl)-2,6-dichloropyridine-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In formic acid; water	2 EXAMPLE 2 STR42 (Process c, variant γ) EXAMPLE 2 STR42 (Process c, variant γ) A mixture of 1.93 g (0.01 mol) of 2,6-dichloropyridine-4-carboxamide, 0.89 g (0.011 mol) of formaline (37 per cent strength) and 2.03 g (0.012 mol) of sodium benzenesulphinate in 12 ml of formic acid is refluxed for 2.5 hours and subsequently cooled to 70° C. The reaction mixture is diluted with 50 ml of water and stirred for 15 minutes at room temperature. The precipitate which has separated out is filtered off with suction and dried. The product is recrystallized from an ethanol/chloroform/petroleum ether mixture. 1.9 g (53% of theory) of N-(benzenesulphonylmethyl)-2,6-dichloropyridine-4-carboxamide of melting point 209° to 210° C. are obtained.

Reference： [1]Current Patent Assignee: BAYER AG - US5583151, 1996, A

12
[ 107-03-9 ]
[ 89281-13-0 ]
[ 313269-84-0 ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium methylate In methanol; N,N-dimethyl-formamide at 20℃;
	With sodium methylate In methanol; N,N-dimethyl-formamide at 20℃;

Reference： [1]Miletin, Miroslav; Hartl, Jiri; Dolezal, Martin; Odlerova; Kralova; Machacek, Milos [Molecules, 2000, vol. 5, # 3, p. 208 - 218]
[2]Miletin, Miroslav; Dolezal, Martin; Opletalova, Veronika; Hartl, Jiri; Kral'ova, Katarina; Machacek, Milos [Molecules, 2001, vol. 6, # 7, p. 603 - 613]

13
[ 111-31-9 ]
[ 89281-13-0 ]
[ 313269-85-1 ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium methylate In methanol; N,N-dimethyl-formamide at 20℃;

Reference： [1]Miletin, Miroslav; Hartl, Jiri; Dolezal, Martin; Odlerova; Kralova; Machacek, Milos [Molecules, 2000, vol. 5, # 3, p. 208 - 218]

14
[ 89281-13-0 ]
[ 75-08-1 ]
2-chloro-6-ethylsulfanyl-isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium methylate In methanol; N,N-dimethyl-formamide at 20℃;

Reference： [1]Miletin, Miroslav; Hartl, Jiri; Dolezal, Martin; Odlerova; Kralova; Machacek, Milos [Molecules, 2000, vol. 5, # 3, p. 208 - 218]

15
[ 109-79-5 ]
[ 89281-13-0 ]
[ 441313-34-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate In methanol; N,N-dimethyl-formamide at 20℃;

Reference： [1]Miletin, Miroslav; Dolezal, Martin; Opletalova, Veronika; Hartl, Jiri; Kral'ova, Katarina; Machacek, Milos [Molecules, 2001, vol. 6, # 7, p. 603 - 613]

16
[ 89281-13-0 ]
[ 401523-91-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NaOMe / dimethylformamide; methanol / 20 °C 2: 77 percent / aq. NaOH / ethanol / Heating

Reference： [1]Miletin, Miroslav; Dolezal, Martin; Opletalova, Veronika; Hartl, Jiri; Kral'ova, Katarina; Machacek, Milos [Molecules, 2001, vol. 6, # 7, p. 603 - 613]

17
[ 89281-13-0 ]
[ 401523-92-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NaOMe / dimethylformamide; methanol / 20 °C 2: 75 percent / aq. NaOH / ethanol / Heating

Reference： [1]Miletin, Miroslav; Dolezal, Martin; Opletalova, Veronika; Hartl, Jiri; Kral'ova, Katarina; Machacek, Milos [Molecules, 2001, vol. 6, # 7, p. 603 - 613]

18
[ 89281-13-0 ]
2-chloro-<i>N</i>-(2-hydroxy-phenyl)-6-propylsulfanyl-isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: NaOMe / dimethylformamide; methanol / 20 °C 2.1: 77 percent / aq. NaOH / ethanol / Heating 3.1: SOCl₂ / benzene / 1 h / Heating 3.2: 44 percent / pyridine / acetone / 10 °C

Reference： [1]Miletin, Miroslav; Dolezal, Martin; Opletalova, Veronika; Hartl, Jiri; Kral'ova, Katarina; Machacek, Milos [Molecules, 2001, vol. 6, # 7, p. 603 - 613]

19
[ 89281-13-0 ]
2-butylsulfanyl-6-chloro-<i>N</i>-(2-hydroxy-phenyl)-isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: NaOMe / dimethylformamide; methanol / 20 °C 2.1: 75 percent / aq. NaOH / ethanol / Heating 3.1: SOCl₂ / benzene / 1 h / Heating 3.2: 56 percent / pyridine / acetone / 10 °C

Reference： [1]Miletin, Miroslav; Dolezal, Martin; Opletalova, Veronika; Hartl, Jiri; Kral'ova, Katarina; Machacek, Milos [Molecules, 2001, vol. 6, # 7, p. 603 - 613]

20
[ 89281-13-0 ]
2-chloro-<i>N</i>-(5-chloro-2-hydroxy-phenyl)-6-propylsulfanyl-isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: NaOMe / dimethylformamide; methanol / 20 °C 2.1: 77 percent / aq. NaOH / ethanol / Heating 3.1: SOCl₂ / benzene / 1 h / Heating 3.2: 53 percent / pyridine / acetone / 10 °C

Reference： [1]Miletin, Miroslav; Dolezal, Martin; Opletalova, Veronika; Hartl, Jiri; Kral'ova, Katarina; Machacek, Milos [Molecules, 2001, vol. 6, # 7, p. 603 - 613]

21
[ 89281-13-0 ]
2-chloro-<i>N</i>-(3-chloro-4-hydroxy-phenyl)-6-propylsulfanyl-isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: NaOMe / dimethylformamide; methanol / 20 °C 2.1: 77 percent / aq. NaOH / ethanol / Heating 3.1: SOCl₂ / benzene / 1 h / Heating 3.2: 34 percent / pyridine / acetone / 10 °C

Reference： [1]Miletin, Miroslav; Dolezal, Martin; Opletalova, Veronika; Hartl, Jiri; Kral'ova, Katarina; Machacek, Milos [Molecules, 2001, vol. 6, # 7, p. 603 - 613]

22
[ 89281-13-0 ]
2-butylsulfanyl-6-chloro-<i>N</i>-(3-chloro-4-hydroxy-phenyl)-isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: NaOMe / dimethylformamide; methanol / 20 °C 2.1: 75 percent / aq. NaOH / ethanol / Heating 3.1: SOCl₂ / benzene / 1 h / Heating 3.2: 53 percent / pyridine / acetone / 10 °C

Reference： [1]Miletin, Miroslav; Dolezal, Martin; Opletalova, Veronika; Hartl, Jiri; Kral'ova, Katarina; Machacek, Milos [Molecules, 2001, vol. 6, # 7, p. 603 - 613]

23
[ 89281-13-0 ]
2-butylsulfanyl-6-chloro-<i>N</i>-(5-chloro-2-hydroxy-phenyl)-isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: NaOMe / dimethylformamide; methanol / 20 °C 2.1: 75 percent / aq. NaOH / ethanol / Heating 3.1: SOCl₂ / benzene / 1 h / Heating 3.2: 59 percent / pyridine / acetone / 10 °C

Reference： [1]Miletin, Miroslav; Dolezal, Martin; Opletalova, Veronika; Hartl, Jiri; Kral'ova, Katarina; Machacek, Milos [Molecules, 2001, vol. 6, # 7, p. 603 - 613]

24
[ 89281-13-0 ]
2-chloro-6-ethylsulfanyl-thioisonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 65 percent / NaOMe / methanol; dimethylformamide / 20 °C 2: 89 percent / Lawesson's reagent / toluene / Heating

Reference： [1]Miletin, Miroslav; Hartl, Jiri; Dolezal, Martin; Odlerova; Kralova; Machacek, Milos [Molecules, 2000, vol. 5, # 3, p. 208 - 218]

25
[ 89281-13-0 ]
2-chloro-6-propylsulfanyl-thioisonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 76 percent / NaOMe / methanol; dimethylformamide / 20 °C 2: 87 percent / Lawesson's reagent / toluene / Heating

Reference： [1]Miletin, Miroslav; Hartl, Jiri; Dolezal, Martin; Odlerova; Kralova; Machacek, Milos [Molecules, 2000, vol. 5, # 3, p. 208 - 218]

26
[ 89281-13-0 ]
2-chloro-6-hexylsulfanyl-thioisonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 72 percent / NaOMe / methanol; dimethylformamide / 20 °C 2: 91 percent / Lawesson's reagent / toluene / Heating

Reference： [1]Miletin, Miroslav; Hartl, Jiri; Dolezal, Martin; Odlerova; Kralova; Machacek, Milos [Molecules, 2000, vol. 5, # 3, p. 208 - 218]

27
[ 89281-13-0 ]
[ 313269-91-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 72 percent / NaOMe / methanol; dimethylformamide / 20 °C 2: 75 percent / NaOMe / methanol; dimethylformamide / 50 °C

Reference： [1]Miletin, Miroslav; Hartl, Jiri; Dolezal, Martin; Odlerova; Kralova; Machacek, Milos [Molecules, 2000, vol. 5, # 3, p. 208 - 218]

28
[ 89281-13-0 ]
2-ethylsulfanyl-6-hexylsulfanyl-thioisonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 72 percent / NaOMe / methanol; dimethylformamide / 20 °C 2: 75 percent / NaOMe / methanol; dimethylformamide / 50 °C 3: 90 percent / Lawesson's reagent / toluene / Heating

Reference： [1]Miletin, Miroslav; Hartl, Jiri; Dolezal, Martin; Odlerova; Kralova; Machacek, Milos [Molecules, 2000, vol. 5, # 3, p. 208 - 218]

29
[ 89281-13-0 ]
2-butylsulfanyl-6-hexylsulfanyl-thioisonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 72 percent / NaOMe / methanol; dimethylformamide / 20 °C 2: 72 percent / NaOMe / methanol; dimethylformamide / 50 °C 3: 91 percent / Lawesson's reagent / toluene / Heating

Reference： [1]Miletin, Miroslav; Hartl, Jiri; Dolezal, Martin; Odlerova; Kralova; Machacek, Milos [Molecules, 2000, vol. 5, # 3, p. 208 - 218]

30
[ 89281-13-0 ]
[ 313269-92-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 72 percent / NaOMe / methanol; dimethylformamide / 20 °C 2: 72 percent / NaOMe / methanol; dimethylformamide / 50 °C

Reference： [1]Miletin, Miroslav; Hartl, Jiri; Dolezal, Martin; Odlerova; Kralova; Machacek, Milos [Molecules, 2000, vol. 5, # 3, p. 208 - 218]

31
[ 89281-13-0 ]
[ 313269-93-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 72 percent / NaOMe / methanol; dimethylformamide / 20 °C 2: 70 percent / NaOMe / methanol; dimethylformamide / 50 °C

Reference： [1]Miletin, Miroslav; Hartl, Jiri; Dolezal, Martin; Odlerova; Kralova; Machacek, Milos [Molecules, 2000, vol. 5, # 3, p. 208 - 218]

32
[ 89281-13-0 ]
2-hexylsulfanyl-6-pentylsulfanyl-thioisonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 72 percent / NaOMe / methanol; dimethylformamide / 20 °C 2: 70 percent / NaOMe / methanol; dimethylformamide / 50 °C 3: 89 percent / Lawesson's reagent / toluene / Heating

Reference： [1]Miletin, Miroslav; Hartl, Jiri; Dolezal, Martin; Odlerova; Kralova; Machacek, Milos [Molecules, 2000, vol. 5, # 3, p. 208 - 218]

33
[ 89281-13-0 ]
[ 313269-94-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 72 percent / NaOMe / methanol; dimethylformamide / 20 °C 2: 67 percent / NaOMe / methanol; dimethylformamide / 50 °C

Reference： [1]Miletin, Miroslav; Hartl, Jiri; Dolezal, Martin; Odlerova; Kralova; Machacek, Milos [Molecules, 2000, vol. 5, # 3, p. 208 - 218]

34
[ 89281-13-0 ]
2-heptylsulfanyl-6-hexylsulfanyl-thioisonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 72 percent / NaOMe / methanol; dimethylformamide / 20 °C 2: 67 percent / NaOMe / methanol; dimethylformamide / 50 °C 3: 89 percent / Lawesson's reagent / toluene / Heating

Reference： [1]Miletin, Miroslav; Hartl, Jiri; Dolezal, Martin; Odlerova; Kralova; Machacek, Milos [Molecules, 2000, vol. 5, # 3, p. 208 - 218]

35
[ 89281-13-0 ]
[ 313269-95-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 72 percent / NaOMe / methanol; dimethylformamide / 20 °C 2: 64 percent / NaOMe / methanol; dimethylformamide / 50 °C

Reference： [1]Miletin, Miroslav; Hartl, Jiri; Dolezal, Martin; Odlerova; Kralova; Machacek, Milos [Molecules, 2000, vol. 5, # 3, p. 208 - 218]

36
[ 89281-13-0 ]
2-hexylsulfanyl-6-octylsulfanyl-thioisonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 72 percent / NaOMe / methanol; dimethylformamide / 20 °C 2: 64 percent / NaOMe / methanol; dimethylformamide / 50 °C 3: 87 percent / Lawesson's reagent / toluene / Heating

Reference： [1]Miletin, Miroslav; Hartl, Jiri; Dolezal, Martin; Odlerova; Kralova; Machacek, Milos [Molecules, 2000, vol. 5, # 3, p. 208 - 218]

37
[ 89281-13-0 ]
2,6-Bis-methylsulfanyl-thioisonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 80 percent / dimethylformamide / 50 °C 2: 87 percent / Lawesson's reagent / toluene / Heating

Reference： [1]Miletin; Hartl; Odlerova; Machacek [Pharmazie, 1997, vol. 52, # 7, p. 558 - 560]

38
[ 89281-13-0 ]
2,6-Bis-ethylsulfanyl-thioisonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 82 percent / NaOMe / dimethylformamide / 50 °C 2: 89 percent / Lawesson's reagent / toluene / Heating

Reference： [1]Miletin; Hartl; Odlerova; Machacek [Pharmazie, 1997, vol. 52, # 7, p. 558 - 560]

39
[ 89281-13-0 ]
2,6-Bis-propylsulfanyl-thioisonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 85 percent / NaOMe / dimethylformamide / 50 °C 2: 90 percent / Lawesson's reagent / toluene / Heating

Reference： [1]Miletin; Hartl; Odlerova; Machacek [Pharmazie, 1997, vol. 52, # 7, p. 558 - 560]

40
[ 89281-13-0 ]
2,6-Bis-butylsulfanyl-thioisonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 83 percent / NaOMe / dimethylformamide / 50 °C 2: 90 percent / Lawesson's reagent / toluene / Heating

Reference： [1]Miletin; Hartl; Odlerova; Machacek [Pharmazie, 1997, vol. 52, # 7, p. 558 - 560]

41
[ 89281-13-0 ]
[ 88579-63-9 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1933,vol. 52,p. 55,59

42
[ 89281-13-0 ]
[ 101990-69-6 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1933,vol. 52,p. 55,59

43
[ 5398-44-7 ]
[ 89281-13-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride
	Multi-step reaction with 2 steps 1: SOCl₂
	Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 24 h / 80 °C 2: ammonium hydroxide; pyridine / dichloromethane / 4 h / 0 - 20 °C

Reference： [1]Levelt; Wibaut [Recueil des Travaux Chimiques des Pays-Bas, 1929, vol. 48, p. 468,471]
[2]Wibaut; Overhoff [Recueil des Travaux Chimiques des Pays-Bas, 1933, vol. 52, p. 55,59]
[3]Changunda, Charles R.K.; Rousseau, Amanda L.; Basson, Adriaan E.; Bode, Moira L. [Arkivoc, 2021, vol. 2020, # 3, p. 152 - 170]

44
[ 89281-13-0 ]
[ 73874-95-0 ]
[ 848498-77-1 ]

Yield	Reaction Conditions	Operation in experiment
	With N,N-dimethyl-3-methylbutylamine In N,N-dimethyl acetamide at 150℃; for 0.333333h; Microwave;	tert-Butyl piperidin-4-ylcarbamate (500 mg, 2.62 MMOL), was dissolved in anhydrous N, N'- dimethyl acetamide (4 ml). 2, 6-Dichloroisonicotinamide (522 mg, 2.62 mmol) was added, followed by N, N-dimethyl isopropylethylamine (465 p1, 2.62 MMOL). Using a Smith Microwave Synthesizer, the mixture was subjected to single-mode microwave at 150 °C for 20 minutes. H20 (50 ML) and EtOAc (100 ml) were added, the EtOAc layer was washed (4 x 50 ML), dried over NA2SO4 and concentrated in vacuo to give the title product as a brown solid. (760 mg). MS (ES, M+H): 355 for CI6H23CIN403 LH NMR B : 1. 42 (m, 2H) ; 1. 53 (s, 9H); 1.94 (m, 2H); 3.12 (m, 2H); 3.45 (s, 1H) ; 3.70 (m, IH) ; 4. 34 (m, 2H); 7.07 (s, IH) ; 7.26 (s, IH) ; 7.81 (s, IH) ; 8.49 (s, 1H).

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC Location in patent: Page/Page column 78

45
[ 89281-13-0 ]
N-(hydroxymethyl)-2,6-dichloropyridine-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; paraformaldehyde In water; ethyl acetate	3 EXAMPLE 3 STR43 (Process b) EXAMPLE 3 STR43 (Process b) A mixture of 3.9 g (0.02 mol) of 2,6-dichloropyridine-4-carboxamide, 0.56 g (0.04 mol) of potassium carbonate and 0.36 g (0.02 mol) of water in 40 ml of ethyl acetate is refluxed for 15 minutes, 0.6 g (0.02 mol) of paraformaldehyde is subsequently added at boiling point, and the mixture is heated at the boil for a further 1 to 2 minutes. The hot solution is filtered, the filtrate is evaporated, and the residue is triturated with diethyl ether, filtered off with suction and dried. 3.75 g (85% of theory) of N-(hydroxymethyl)-2,6-dichloropyridine-4-carboxamide of melting point 155° to 157° C. (decomposition) are obtained.

Reference： [1]Current Patent Assignee: BAYER AG - US5583151, 1996, A

46
[ 7664-93-9 ]
[ 20546-32-1 ]
[ 89281-13-0 ]
N-(N-methyl-N-formyl-amino-methyl)-2,6-dichloropyridine-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; acetic acid	1 EXAMPLE 1 STR41 (Process a) EXAMPLE 1 STR41 (Process a) 2.25 g (0,022 mol) of concentrated sulphuric acid are added dropwise with cooling and stirring at 20° C. to 25° C. to a suspension of 1.93 g (0.01 mol) of 2,6-dichloropyridine-4-carboxamide and 0.89 g (0.01 mol) of N-hydroxymethyl-N-methyl-formamide in 15 ml of glacial acetic acid (compare, for example, Synthesis 1984, 218), and the mixture is subsequently stirred for 24 hours at room temperature. For working-up, 25 ml of water are added dropwise with cooling and stirring at 20° C. to 25° C. The reaction mixture is subsequently extracted five times using 40 ml portions of dichloromethane, the combined organic extracts are dried over sodium sulphate and concentrated under reduced pressure, the oily residue is crystallized by trituration with water, and the crystals are dried. 1.63 g (62% of theory) of N-(N-methyl-N-formyl-amino-methyl)-2,6-dichloropyridine-4-carboxamide of melting point 150° to 155° C. are obtained.

Reference： [1]Current Patent Assignee: BAYER AG - US5583151, 1996, A

47
[ 79-37-8 ]
[ 89281-13-0 ]
2,6-dichloroisonicotinoyl isocyanate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,2-dichloro-ethane	1.1.b b) b) Preparation of 2,6-dichloroisonicotinoyl isocyanate (intermediate) STR10 18 g of 2,6-dichloroisonicotinamide are dissolved in 180 ml of ethylene chloride, and 14.7 g of oxalyl chloride are added dropwise at 0°-5° C. The mixture is subsequently refluxed for 8 hours and cooled, and the solution is concentrated. Distillation under a high vacuum yields an oil boiling at 65°-7° C./4 Pa (82.1% of theory).

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US5049569, 1991, A

48
[ 101990-72-1 ]
[ 1450-14-2 ]
[ 89281-13-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid In methanol; dichloromethane	1.1.a a) a) Preparation of 2,6-dichloroisonicotinamide (starting material) STR9 53.1 g of hexamethyldisilane are initially introduced into 600 ml of abs. methylene chloride. 63 g of 2,6-dichloroisonicotinyl chloride in 500 ml of methylene chloride are added dropwise and with cooling at 0°-5° C., and stirring is continued overnight at room temperature. On the next day, 60 ml of methanol and 600 ml of 5% sulfuric acid are added dropwise in succession. The precipitate which deposits is filtered off and washed with water. 54 g (95%) of white crystals of melting point 198-200° C. are obtained.

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US5049569, 1991, A

49
[ 98027-84-0 ]
[ 3019-71-4 ]
[ 89281-13-0 ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: 2,6-dichloro-4-iodopyridine With chloro-trimethyl-silane; ethylene dibromide; lithium chloride; zinc In tetrahydrofuran at 18℃; Inert atmosphere; Stage #2: Trichloroacetyl isocyanate In tetrahydrofuran at -20 - 25℃; Inert atmosphere; Stage #3: With methanol; potassium carbonate In tetrahydrofuran at 25℃; for 12h; Inert atmosphere;

Reference： [1]Schade, Matthias A.; Manolikakes, Georg; Knochel, Paul [Organic Letters, 2010, vol. 12, # 16, p. 3648 - 3650]

50
[ 2402-78-0 ]
[ 64-18-6 ]
[ 89281-13-0 ]

Yield	Reaction Conditions	Operation in experiment
16 g	Stage #1: 2,6-dichloropyridine; formic acid With ruthenium-carbon composite; trifluoroacetic anhydride In dimethyl sulfoxide at 5 - 90℃; for 0.833333h; Inert atmosphere; Stage #2: With ammonia In dimethyl sulfoxide at 140℃; for 2h;	2; 3; 4; 5 Example 2 In a high pressure reactor, under argon protection, start cooling, internal temperature 5 ~ 10 ° C, 15g of 2,6-dichloropyridine added to trifluoroacetic anhydride 42g, formic acid 9.2g and dimethyl sulfoxide 150mL mixed solution In the middle, keep the temperature unchanged, add 1.5g of activated carbon supported ruthenium / ruthenium catalyst; slowly heat up to 90 ° C for 50min, add ammonia gas into the reactor, the pressure inside the kettle reaches 0.1MPa; keep the pressure unchanged, continue to rise high temperature At 140 ° C, after 2 h of reaction, TLC monitored the reaction of the starting material completely and cooled to room temperature. The reaction solution was filtered, and the filtrate was added to 100 mL of water, and extracted with dichloromethane (100 mL), and the organic phase was combined, dried over anhydrous magnesium sulfate and concentrated to give 2,6-dichloro-4-carboxamide pyridine 16 g;

Reference： [1]Current Patent Assignee: HENAN WANLIU BIOTECHNOLOGY - CN109053805, 2018, A Location in patent: Paragraph 0027-0038

51
[ 42521-08-4 ]
[ 89281-13-0 ]

Yield	Reaction Conditions	Operation in experiment
169 mg	With pyridine; ammonium hydroxide In dichloromethane at 0 - 20℃; for 4h;	General preparation of amides 7 and 13. General procedure: An appropriate aromatic carboxylic acid 6 or 12 (382 mg, 2.0 mmol) and a magnetic stirrer bar were placed into a 50 ml round-bottomed flask containing thionyl chloride (10 ml). The mixture was gently stirred and refluxed in an oil bath at 80°C for 24 h. After cooling to room temperature, excess thionyl chloride was removed in vacuo to leave a crude residue of the acid chloride that was subsequently used without further purification. A solution of the acid chloride (2.0 mmol) in dichloromethane (5 ml) was cautiously added to an ice-cold mixture of excess 25% aqueous ammonia (5 ml) and pyridine (1 ml) in dichloromethane (15 ml). The mixture was stirred at 0°C (30 min) and then allowed to warm to room temperature for 4 h. The reaction was washed successively with aqueous saturated NaHCO3 (2 x 10 ml), saturated brine solution (10 ml), distilled water (2 x 10 ml) and finally dried over anhydrous Na2SO4. After removal of the solvent, the crude mixture was purified by silica gel flash column chromatography, eluting with 5-10% EtOAc/hexane.

Reference： [1]Changunda, Charles R.K.; Rousseau, Amanda L.; Basson, Adriaan E.; Bode, Moira L. [Arkivoc, 2021, vol. 2020, # 3, p. 152 - 170]

52
[ 89281-13-0 ]
[ 848498-95-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N,N-dimethyl-3-methylbutylamine / N,N-dimethyl acetamide / 0.33 h / 150 °C / Microwave 2: 1,1'-bis(diphenylphosphino)ferrocene / (dibenzylideneacetone)palladium / 1,4-dioxane / 5 h / 100 °C

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC

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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