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[ CAS No. 928783-85-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 928783-85-1

Chemical Structure| 928783-85-1

Chemical Structure| 928783-85-1

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Quality Control of [ 928783-85-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 928783-85-1 ]

SDS Specification

Alternatived Products of [ 928783-85-1 ]

Product Details of [ 928783-85-1 ]

CAS No. :	928783-85-1	MDL No. :	MFCD09260894
Formula :	C₇H₃BrClF₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QRPRXRQFNNXPBA-UHFFFAOYSA-N
M.W :	259.45	Pubchem ID :	20269855
Synonyms :

Calculated chemistry of [ 928783-85-1 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	44.15
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.95 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.48
Log Po/w (XLOGP3) :	4.13
Log Po/w (WLOGP) :	5.27
Log Po/w (MLOGP) :	4.66
Log Po/w (SILICOS-IT) :	4.17
Consensus Log Po/w :	4.14

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.35
Solubility :	0.0115 mg/ml ; 0.0000442 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.84
Solubility :	0.0378 mg/ml ; 0.000146 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.75
Solubility :	0.00456 mg/ml ; 0.0000176 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.71

Safety of [ 928783-85-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P261-P271-P280-P305+P351+P338-P302+P352-P304+P340-P312-P362+P364-P403+P233-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 928783-85-1 ]

* 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 [ 928783-85-1 ]

[ 928783-85-1 ] Synthesis Path-Downstream 1~15

1
[ 40499-83-0 ]
[ 928783-85-1 ]
[ 1198181-75-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With caesium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 85℃; for 16h;Inert atmosphere;	Reference Example 70 1-[3-chloro-5-(trifluoromethyl)phenyl]pyrrolidin-3-ol ; A solution of <strong>[928783-85-1]1-bromo-3-chloro-5-(trifluoromethyl)benzene</strong> (5.0 g), 3-hydroxypyrrolidine (1.85 g), palladium(II) acetate (217 mg), (+/-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (1.2 g) and cesium carbonate (18.8 g) in toluene (96 mL) was stirred under an argon gas atmosphere at 85C for 16 hr. After cooling to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate 80:20 - 10:90) to give the title compound (4.11 g, yield 80%) as a brown oil. 1H-NMR (300 MHz, CDCl3)delta:1.65 (d, J = 3.8 Hz, 1 H), 2.00 - 2.29 (m, 2 H), 3.19 - 3.32 (m, 1 H), 3.38 (td, J = 8.7, 3.4 Hz, 1 H), 3.45 - 3.60 (m, 2 H), 4.58 - 4.72 (m, 1 H), 6.61 (s, 1 H), 6. 63 - 6.68 (m, 1 H), 6.88 (s, 1 H).
80%	With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl;palladium diacetate; In toluene; at 85℃; for 16h;Inert atmosphere;	A solution of <strong>[928783-85-1]1-bromo-3-chloro-5-(trifluoromethyl)benzene</strong> (5.0 g), 3-hydroxypyrrolidine (1.85 g), palladium(II) acetate (217 mg), (+/-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (1.2 g) and cesium carbonate (18.8 g) in toluene (96 mL) was stirred under an argon gas atmosphere at 85 C. for 16 hr. After cooling to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate 80:20-10:90) to give the title compound (4.11 g, yield 80%) as a brown oil.1H-NMR (300 MHz, CDCl3) delta: 1.65 (d, J=3.8 Hz, 1H), 2.00-2.29 (m, 2 H), 3.19-3.32 (m, 1H), 3.38 (td, J=8.7, 3.4 Hz, 1H), 3.45-3.60 (m, 2H), 4.58-4.72 (m, 1H), 6.61 (s, 1H), 6.63-6.68 (m, 1H), 6.88 (s, 1H).

Reference： [1]Patent: EP2295406,2011,A1 .Location in patent: Page/Page column 70
[2]Patent: US2011/251187,2011,A1 .Location in patent: Page/Page column 51

2
[ 928783-85-1 ]
[ 1198180-50-5 ]

Reference： [1]Patent: EP2295406,2011,A1
[2]Patent: US2011/251187,2011,A1

3
[ 383-63-1 ]
[ 928783-85-1 ]
[ 1125812-58-9 ]

Yield	Reaction Conditions	Operation in experiment
78%		In a 500 ml multineck flask with low-temperature thermometer, dropping funnel and argon balloon, 5.5 g (0.228 mol, 1.3 eq) of magnesium turnings (activated with dibromoethane and washed with diethyl ether) were blanketed with 120 ml of diethyl ether. At 0 C., 45.5 g of <strong>[928783-85-1]3-bromo-5-chlorobenzotrifluoride</strong> (0.175 mol, 1 eq) in 120 ml of diethyl ether were slowly added dropwise. The reaction started up of its own accord after a few minutes, with a colour change (red-brown) and heating; the temperature was kept at about 0 C. during the addition. On completion of addition of the bromide, the mixture was stirred for a further 30 min.A separate 2 l 3-neck flask with low-temperature thermometer, dropping funnel and argon balloon was initially charged with 32.4 g of ethyl trifluoroacetate (0.228 mol, 1.3 eq) in 250 ml of diethyl ether, and cooled to -80 C. At this temperature, the Grignard reagent (cooled to -10 C.) was slowly added dropwise. On completion of addition, the reaction mixture was stirred at -80 C. for a further 30 min. Thereafter, the reaction mixture was warmed to -10 C. and acidified with 10% hydrochloric acid. The resulting mixture was admixed with saturated NaCl solution, the phases were separated and the aqueous phase was washed with 200-300 ml of diethyl ether. The combined ethereal phases were dried over magnesium sulphate and the solvent was subsequently removed on a rotary evaporator.The resulting crude product was purified by vacuum distillation (71 C. at 18 mbar). 37.7 g (78% of theory) of 1-[3-chloro-5-(trifluoromethyl)phenyl]-2,2,2-trifluoroethanone were obtained as a colourless oil. This was converted further without further purification.

Reference： [1]Patent: US2011/105532,2011,A1 .Location in patent: Page/Page column 40

4
[ 928783-85-1 ]
[ 1299483-02-5 ]

Reference： [1]Patent: US2011/105532,2011,A1

5
[ 928783-85-1 ]
[ 1299483-09-2 ]

Reference： [1]Patent: US2011/105532,2011,A1

6
[ 928783-85-1 ]
4-[(1E)-3-({1-[3-chloro-5-(trifluoromethyl)phenyl]-2,2,2-trifluoroethyl}amino)-3-oxoprop-1-en-1-yl]-N-cyclopropyl-2-(trifluoromethyl)benzamide [ No CAS ]

Reference： [1]Patent: US2011/105532,2011,A1
[2]Patent: US2011/105532,2011,A1

7
[ 928783-85-1 ]
N-[α,3-bis(trifluoromethyl)-5-fluorobenzenemethane]-3-trifluoromethyl-4-(N-cyclopropylcarbamoyl)cinnamide [ No CAS ]

Reference： [1]Patent: US2011/105532,2011,A1

8
[ 928783-85-1 ]
C₁₀H₂₁NO [ No CAS ]
cis-3-[(3-chloro-5-trifluoromethyl-phenylamino)-methyl]-3,5,5-trimethyl-cyclohexanol [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 603 - 607

9
[ 928783-85-1 ]
[ 1533425-28-3 ]
[ 1533425-32-9 ]

Yield	Reaction Conditions	Operation in experiment
12%	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tert-butyl XPhos; In toluene; at 110℃; under 760.051 Torr; for 3h;Inert atmosphere;	In a 25 mL sealed tube, sodium 2-methylpropan-2-olate (62.7 mg, 653 muetaiotaomicron, Eq: 1.20), bis(dibenzylideneacetone)palladium (31.3 mg, 54.4 muetaiotaomicron, Eq: 0.1) and 2-di-tert-butyl(2',4',6'- triisopropylbiphenyl-2-yl)phosphine (23.1 mg, 54.4 muetaiotaomicron, Eq: 0.1) were combined with toluene (5.00 mL) to give a dark brown suspension. N5,N5,l-tris(4-methoxybenzyl)-lH-l,2,4-triazole- 3,5-diamine (250 mg, 544 muetaiotaomicron, Eq: 1.00) and l-bromo-3-chloro-5-(trifluoromethyl)benzene (141 mg, 544 muetaiotaomicron, Eq: 1.00) were added. The reaction mixture was degassed with argon for 15 min, and then heated to 110C for 3 hours. The reaction mixture was cooled and diluted with EtOAc (50 mL), washed with H20 (25 mL) and brine (25 mL). The organic layer was dried over anhydrous MgS04, filtered and volatiles were removed under reduced pressure to yield an oil from which the compound was isolated by column chromatography (Hexanes/EtOAc = 70/30) to give an off-white solid 40 mg (12%). MH+ 638.4

Reference： [1]Patent: WO2014/6066,2014,A1 .Location in patent: Paragraph 0296

10
[ 928783-85-1 ]
[ 57260-71-6 ]
1-halo-3,5-bis(trifluoromethyl)benzene [ No CAS ]
[ 1542213-26-2 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 1063 - 1078

11
[ 928783-85-1 ]
[ 346729-48-4 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 1063 - 1078

12
[ 928783-85-1 ]
[ 1542213-99-9 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 1063 - 1078

13
[ 6746-94-7 ]
[ 928783-85-1 ]
C₁₂H₈ClF₃ [ No CAS ]

Reference： [1]Chemical Science,2019,vol. 10,p. 3481 - 3485

14
[ 354-32-5 ]
[ 928783-85-1 ]
[ 1125812-58-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-bromo-3-chloro-5-(trifluoromethyl)benzene With magnesium In 2-methyltetrahydrofuran at 50 - 60℃; Inert atmosphere; Stage #2: trifluoracetyl chloride In 2-methyltetrahydrofuran at -80℃; Inert atmosphere;	1.3; 2.3 (3) Synthesis of 3-chloro-5-trifluoromethyltrifluoroacetophenone Under the protection of nitrogen, add 1kg of 2-methyltetrahydrofuran, 24.6g of magnesium chips (1.16eq) and 1g of 1,2-dibromoethane into a 3L three-necked flask, and first add 22.6g of 1-bromo-3-chloro-5-(trifluoromethyl)benzene -(0.1eq, 1eq in total)to it , heated to 50-60°C, after initiation, stop heating, use reaction exotherm to maintain the internal temperature 50-60°C, after the raw materials in the bottle have reacted, Then slowly add the remaining 203.4g of 1-bromo-3-chloro-5-(trifluoromethyl)benzene (0.9eq, 1eq in total), 1-3 hours after the dripping is completed, and then keep the reaction incubation, and monitor 1-bromo- in the gas phase. The progress of the reaction of 3-chloro-5-(trifluoromethyl)benzene, monitoring showed that the reaction proceeded for 2h, and the reaction of 1-bromo-3-chloro-5-(trifluoromethyl)benzene was completed. At this time, the reaction liquid Cool down to 20°C to obtain Grignard reagent solution.Under the protection of nitrogen, under continuous stirring, add 500g of 2-methyltetrahydrofuran to another 3L three-necked flask, then cool to -80 and keep it, and then add 127g of trifluoroacetyl chloride gas (1.1eq), then , Slowly drip the above-mentioned Grignard reagent solution into it, control the internal temperature at -80°C to -70°C, and then keep the reaction for 2 hours after the dripping is completed for 1 to 2 hours to obtain the third reaction solution.The third reaction solution was naturally heated to 20°C, and 1kg of dilute hydrochloric acid solution with a mass concentration of 7% was added dropwise to the third reaction solution. The dripping took 20 minutes, and then 300g of methyl tert-butyl ether was added. The separated organic phase was washed once with 500g saturated sodium chloride solution, dried with anhydrous sodium sulfate, spin-dried, and finally rectified under reduced pressure with a water pump at a top temperature of 82-83°C to obtain 180g of a colorless liquid.

Reference： [1]Current Patent Assignee: SHANGHAI SINOFLUORO SCIENT - CN113636919, 2021, A Location in patent: Paragraph 0074; 0084-0089; 0103-0107

15
[ 928783-85-1 ]
[ 73183-34-3 ]
[ 942069-65-0 ]

Yield	Reaction Conditions	Operation in experiment
34.45%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; anhydrous potassium acetate In 1,4-dioxane at 90℃; for 16h;	6DD.1 Step 1: Synthesis of 2-(3-chloro-5-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2- dioxaborolane A mixture of 1-bromo-3-chloro-5-(trifluoromethyl)benzene (19.9 g, 76.70 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (29.22 g, 115.05 mmol) and KOAc (22.58 g, 230.10 mmol, 14.38 mL) in dioxane (300 mL) was degassed with argon for 10 min. Pd(dppf)Cl2*DCM (1 g, 1.22 mmol) was next added and the reaction mixture was heated to 90°C for 16 hr. The reaction mixture was cooled to rt, filtered and concentrated under reduced pressure. The residue was treated with hexane, filtered through thin layer of SiO2 and evaporated to dryness. Crude product was purified by flash chromatography on SiO2 (Hexane:CHCl3) to give 2-[3-chloro-5-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl- 1,3,2-dioxaborolane (8 26.43 mmol, 34.45% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm) 1.12 (s, 12H), 7.92 (m, 3H). GCMS: calcd 306.2; found 306.2; Rt = 7.597 min
34.45%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; anhydrous potassium acetate In 1,4-dioxane at 90℃; for 16h;	6DD.1 Step 1: Synthesis of 2-(3-chloro-5-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2- dioxaborolane A mixture of 1-bromo-3-chloro-5-(trifluoromethyl)benzene (19.9 g, 76.70 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (29.22 g, 115.05 mmol) and KOAc (22.58 g, 230.10 mmol, 14.38 mL) in dioxane (300 mL) was degassed with argon for 10 min. Pd(dppf)Cl2*DCM (1 g, 1.22 mmol) was next added and the reaction mixture was heated to 90°C for 16 hr. The reaction mixture was cooled to rt, filtered and concentrated under reduced pressure. The residue was treated with hexane, filtered through thin layer of SiO2 and evaporated to dryness. Crude product was purified by flash chromatography on SiO2 (Hexane:CHCl3) to give 2-[3-chloro-5-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl- 1,3,2-dioxaborolane (8 26.43 mmol, 34.45% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm) 1.12 (s, 12H), 7.92 (m, 3H). GCMS: calcd 306.2; found 306.2; Rt = 7.597 min

Reference： [1]Current Patent Assignee: TANGO THERAPEUTICS - WO2022/26892, 2022, A1 Location in patent: Paragraph 1042
[2]Current Patent Assignee: TANGO THERAPEUTICS - WO2022/26892, 2022, A1 Location in patent: Paragraph 1042

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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