[ CAS No. 54287-99-9 ] {[proInfo.proName]}

Name: 54287-99-9|5-Hydroxy-2,2-dimethyl-2H-chromene-6-carbaldehyde|97%
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SKU: A143214
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2D 3D

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Quality Control of [ 54287-99-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 54287-99-9 ]

Product Details of [ 54287-99-9 ]

CAS No. :	54287-99-9	MDL No. :	MFCD08705718
Formula :	C₁₂H₁₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VLHVXYPFWRHKHE-UHFFFAOYSA-N
M.W :	204.22	Pubchem ID :	11084938
Synonyms :

Calculated chemistry of [ 54287-99-9 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	57.97
TPSA :	46.53 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.77 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.02
Log Po/w (XLOGP3) :	2.5
Log Po/w (WLOGP) :	2.28
Log Po/w (MLOGP) :	1.22
Log Po/w (SILICOS-IT) :	2.47
Consensus Log Po/w :	2.1

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.91
Solubility :	0.251 mg/ml ; 0.00123 mol/l
Class :	Soluble
Log S (Ali) :	-3.12
Solubility :	0.154 mg/ml ; 0.000754 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.64
Solubility :	0.466 mg/ml ; 0.00228 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.96

Safety of [ 54287-99-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 54287-99-9 ]

* 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 [ 54287-99-9 ]
Downstream synthetic route of [ 54287-99-9 ]

[ 54287-99-9 ] Synthesis Path-Upstream 1~9

1
[ 107-86-8 ]
[ 95-01-2 ]
[ 54287-99-9 ]

Yield	Reaction Conditions	Operation in experiment
50%	With calcium hydroxide In methanol at 20℃; for 48 h;	2,4-Dihydroxybenzaldehyde (15) (3 g/20.17 mmol), calcium hydroxide (1.543 g/20.8 mmol) and 150 mL of methanol were place in a two-necked round-bottom flask. Then, prenal (9.135 g/108.6 mmol) was added dropwise. The mixture was allowed to stir at room temperature for 48 h. The reaction was quenched with HCl 1 M until pH 1–2. The methanol was evaporated and the aqueous phase was extracted with 3 × 150 mL of ethyl acetate. The organic phase was washed with 2 × 100 mL of brine, dried over sodium sulfate anhydrous, filtered and the organic solvent evaporated. The crude product was purified by silica gel flash chromatography (n-hexane/ethyl acetate 9:1). Compound 16 was crystallized from n-hexane/ethyl acetate 3:1 as a yellow solid (2.06 g/50percent).
50%	With calcium hydroxide In methanol at 20℃; for 48 h;	2,4-Dihydroxybenzaldehyde (42) (3g/20.17mmol), calcium hydroxide (1.543g/20.8mmol) and 150mL of methanol were placed in a round-bottom flask. Then, prenal (9.135g/108.6mmol) was added dropwise. The mixture was stirred at room temperature for 48h. The reaction was quenched with HCl 1M until pH 1–2. The methanol was evaporated and the aqueous phase was extracted with 3×150mL of ethyl acetate. The organic phase was washed with 2×100mL of brine, dried over sodium sulfate anhydrous, filtered and the organic solvent evaporated. The crude product was purified by silica gel flash chromatography (n-hexane/ethyl acetate 9:1). Compound 43 was crystallized from n-hexane/ethyl acetate 3:1 as a yellow solid (2.06g/50percent).6-Formyl-5-hydroxy-2,2-dimethyl-2H-benzopyran (43). Mp: 68–69°C. IR ν_max (cm⁻¹) (KBr): 3464, 2967, 2922, 2857, 1628, 1484, 1330, 1294, 1247, 1176, 1107, 1081, 748. ¹H NMR (300.13MHz, CDCl₃) δ (ppm): 11.65 (OH), 9.66 (s, CHO), 7.29 (d, J=8.6), 6.88 (d, J=10.0), 6.44 (d, J=8.6), 5.61 (d, J=10.0), 1.46 (s, 6H). ¹³C NMR (100.63MHz, CDCl₃) δ (ppm): 194.5, 160.6, 158.7, 134.7, 128.6, 115.2, 115.1, 109.4, 108.8, 78.2, 28.4. EIMS m/z (percent): 205 (5, [M+1]^+.), 204 (10 [M]^+.), 190 (15), 189 (100), 187 (60), 159 (12), 131 (12), 103 (10), 77 (12), 51 (6). HRMS (ESI) m/z calcd for C₁₂H₁₃O₃ [M+H]⁺: 205.08570, found: 205.08592.
0.68 g	With calcium hydroxide In methanol at 20℃; for 12 h;	A 1 g portion of 2,4-2 hydroxybenzaldehyde (Compound 2 shown in Figure 1)0.514 g Ca (OH) 2, methanol150mL.3.045 g of prenyl aldehyde (compound 1 shown in FIG. 1) was then added dropwise.Stir at room temperature for 12h.Quench with HCl (1 M) until the pH is 1-2.Methanol was evaporated and the aqueous phase was extracted with 3 * 150 mL of ethyl acetate.The organic phase was washed with 2 * 100 mL saturated brine, dried over anhydrous Na2SO4,Vacuum filtration, and spin dry. The crude product was passed through a column of silica gel (petroleum ether: ethyl acetate = 9: 1)Crystallization gave product 3 (0.68 g) as shown in FIG.

Reference： [1] Journal of Medicinal Chemistry, 2018,
[2] Journal of Organic Chemistry, 2015, vol. 80, # 22, p. 11460 - 11467
[3] Angewandte Chemie - International Edition, 2012, vol. 51, # 32, p. 8092 - 8096
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 11, p. 2941 - 2959
[5] European Journal of Medicinal Chemistry, 2013, vol. 69, p. 798 - 816
[6] Tetrahedron, 2001, vol. 57, # 25, p. 5335 - 5338
[7] Tetrahedron Letters, 2009, vol. 50, # 36, p. 5075 - 5079
[8] Advanced Synthesis and Catalysis, 2005, vol. 347, # 4, p. 555 - 562
[9] Patent: CN106187974, 2016, A, . Location in patent: Paragraph 0044

2
[ 513-35-9 ]
[ 95-01-2 ]
[ 54287-99-9 ]

Yield	Reaction Conditions	Operation in experiment
32%	With pyridine In acetone at 120℃; for 23.5 h; Heating	[0174] Pyridine (0.01 M) solution containing 3-methyl-but-2-enyl (2.0 equivalent) was added to anhydrous acetone solution (0.01 M) containing 2,4-dihydroxyaldehyde (1 equivalent) drop by droop at 120 °C for 5.5 hours, followed by heating for 18 hours. After cooling down at room temperature, the solvent was eliminated under reduced pressure using a rotary evaporator. Pyridine was eliminated by azeotropic distillation along with toluene. The obtained non-purified product was purified by flash column chromatography (EtOAc:n-hexane=1:8) to give the compound 119 as a colorless solid (yield: 32percent, 1.12 g). [0175] ¹H-NMR (CDCl₃, 300 MHz) δ11.61 (s, 1H), 9.62 (s, 1H), 7.25 (d, 1H, J = 8.6 Hz), 6.39 (d, 1H, J = 8.6 Hz), 5.58 (d, 1H, J = 10.0 Hz), 1.42 (s, 6H).

Reference： [1] Patent: EP2871187, 2015, A1, . Location in patent: Paragraph 0173-0175

3
[ 115-19-5 ]
[ 95-01-2 ]
[ 54287-99-9 ]

Yield	Reaction Conditions	Operation in experiment
32%	at 120℃; for 23.5 h;	Pyridine (0.01 M) solution containing 3-methyl-but-2-enyl (2.0 equivalent) was added to anhydrous acetone solution (0.01 M) containing 2,4-dihydroxyaldehyde (1 equivalent) drop by droop at 120° C. for 5.5 hours, followed by heating for 18 hours. After cooling down at room temperature, the solvent was eliminated under reduced pressure using a rotary evaporator. Pyridine was eliminated by azeotropic distillation along with toluene. The obtained non-purified product was purified by flash column chromatography (EtOAc:n-hexane=1:8) to give the compound 119 as a colorless solid (yield: 32percent, 1.12 g). [0272] ¹H-NMR (CDCl₃, 300 MHz) δ11.61 (s, 1H), 9.62 (s, 1H), 7.25 (d, 1H, J=8.6 Hz), 6.39 (d, 1H, J=8.6 Hz), 5.58 (d, 1H, J=10.0 Hz), 1.42 (s, 6H).

Reference： [1] Patent: US2015/183797, 2015, A1, . Location in patent: Paragraph 0270-0272

4
[ 32268-30-7 ]
[ 54287-99-9 ]

Reference： [1] Heterocycles, 1983, vol. 20, # 4, p. 661 - 666
[2] Journal of the American Chemical Society, 2000, vol. 122, # 41, p. 9939 - 9953

5
[ 54287-98-8 ]
[ 54287-99-9 ]

Reference： [1] Chemistry - A European Journal, 2010, vol. 16, # 32, p. 9767 - 9771
[2] Tetrahedron Letters, 1984, vol. 25, # 10, p. 1099 - 1102

6
[ 163041-67-6 ]
[ 54287-99-9 ]

Reference： [1] Journal of the American Chemical Society, 2000, vol. 122, # 41, p. 9939 - 9953

7
[ 31525-67-4 ]
[ 95-01-2 ]
[ 54287-99-9 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 431 - 438
[2] Organic Letters, 1999, vol. 1, # 13, p. 2113 - 2115
[3] Tetrahedron Letters, 1984, vol. 25, # 10, p. 1099 - 1102

8
[ 107-86-8 ]
[ 95-01-2 ]
[ 54287-99-9 ]
[ 33279-69-5 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1999, vol. 72, # 2, p. 259 - 263

9
[ 115-18-4 ]
[ 54287-99-9 ]

Reference： [1] Heterocycles, 1983, vol. 20, # 4, p. 661 - 666

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Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate; In acetone; at 20℃; for 20h;Inert atmosphere;	Potassium carbonate (2.43 g/17.6 mmol) was placed in a round-bottom flask and under nitrogen atmosphere. Then, compound 16 (1.7976 g/8.8 mmol) solubilized in 20 mL of anhydrous acetone was added by syringe. Dimethyl sulfate (1.667/13.2 mmol) was added dropwise and the mixture was allowed to stir for 20 h at room temperature and under nitrogen atmosphere. The reaction was quenched by the addition of 20 mL of distilled water and the acetone was evaporated. The aqueous phase was acidified with HCl 1 N until pH 2-3 and extracted with 3 × 100 mL of ethyl acetate. The organic phase was washed with 2 × 50 mL of brine, dried over sodium sulfate anhydrous, filtered and the organic solvent evaporated. Compound 17 was obtained in quantitative yield as yellow oil.
100%	With potassium carbonate; In acetone; at 20℃; for 20h;Inert atmosphere;	Potassium carbonate (2.43g/17.6mmol) was placed in a round-bottom flask and under nitrogen atmosphere. Then, compound 43 (1.7976g/8.8mmol) solubilized in 20mL of anhydrous acetone was added by syringe. Dimethylsulfate (1.667/13.2mmol) was added dropwise and the mixture was stirred for 20h at room temperature and under nitrogen atmosphere. The reaction was quenched by the addition of 20mL of distilled water and the acetone was evaporated. The aqueous phase was acidified with HCl 1N until pH 2-3 and extracted with 3×100mL of ethyl acetate. The organic phase was washed with 2×50mL of brine, dried over sodium sulfate anhydrous, filtered and the organic solvent evaporated. Compound 44 was obtained in quantitative yield as yellow oil.6-Formyl-5-methoxy-2,2-dimethyl-2H-benzopyran (44). IR numax (cm-1) (KBr): 2974, 2932, 2840, 2747, 1679, 1634, 1463, 1370, 1281, 1249, 1213, 1158, 1110, 1068, 984, 736. 1H NMR (300.13MHz, CDCl3) delta (ppm): 10.18 (s, CHO), 7.66 (d, J=8.6), 6.65 (d, J=8.6), 6.60 (dd, J=9.9, 0.6), 5.70 (d, J=9.9), 3.90 (s, OCH3), 1.47 (s, 6H). EIMS m/z (%): 219 (5, [M+1]+.), 218 (10, [M]+.), 204 (18), 205 (100), 174 (10), 160 (60), 133 (16), 105 (5), 91 (8), 78 (10), 51 (6). 13C NMR (100.63MHz, CDCl3) delta (ppm): 188.3, 160.0, 159.9, 130.5, 129.8, 122.5, 115.9, 114.4, 113.4, 64.4, 28.2. HRMS (ESI) m/z calcd for C13H15O3 [M+H]+: 219.10177; found: 219.10157.
1.5 g	With potassium carbonate; In acetone; at 20℃; for 20h;Inert atmosphere;	into a round bottom flask K2CO3 2.43g, and with N2 protection.31.7976 g of the compound obtained in the previous step was dissolved in anhydrous acetone,And added to the reaction vessel with a syringe. Dropping 1.667g dimethyl sulfate, N2 environment,The reaction was stirred at room temperature for 20 h. Quench with 20 mL of distilled water and evaporate the acetone. The aqueous phase is acidified with 1 N HCl until the pH is 2-3. Extract with 3 * 100 mL of ethyl acetate. The organic layer was washed with 2 * 50 mL saturated brine, dried over anhydrous Na2SO4, filtered and spun dry. The crude product was passed through a column of silica gel (petroleum ether: ethyl acetate = 10: 1) to give product 4 (1.5 g) as shown in FIG.

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate; In acetone; for 3h;Reflux;	Manufacturing Example 38: Preparation of 5-(Methoxy)-2,2-dimethyl-2H-chromene-6-carbaldehyde (121) Iodomethane (0.11 mL, 1.47 mmol) was added to acetone solution (5 mL) containing the compound 110 (200 mg, 0.98 mmol) prepared in Manufacturing Example 29 and potassium carbonate (406 mg, 2.94 mmol) at room temperature. The mixture was refluxed for 3 hours, and then concentrated under reduced pressure. The obtained non-purified residue was extracted with EtOAc. The organic layer was washed with brine. The extract was dried over anhydrous MgSO4, and concentrated under reduced pressure. Then, the obtained residue was purified by flash column chromatography (EtOAc:n-hexane=1:10) to give the compound 121 as a light-yellow solid (yield: 91%, 231 mg). 1H NMR (CDCl3, 300 MHz) delta 10.07 (s, 1H), 7.59 (d, J = 8.6 Hz, 1H), 6.61 (d, J = 8.6 Hz, 1H), 6.53(d, J = 10.0 Hz, 1H), 5.63(d, J = 10.0 Hz, 1H), 5.02(s, 2H), 3.52(s, 3H).
91%	With potassium carbonate; In acetone; at 20℃; for 3h;	Iodomethane (0.11 mL, 1.47 mmol) was added to acetone solution (5 mL) containing the compound 110 (200 mg, 0.98 mmol) prepared in Manufacturing Example 29 and potassium carbonate (406 mg, 2.94 mmol) at room temperature. The mixture was refluxed for 3 hours, and then concentrated under reduced pressure. The obtained non-purified residue was extracted with EtOAc. The organic layer was washed with brine. The extract was dried over anhydrous MgSO4, and concentrated under reduced pressure. Then, the obtained residue was purified by flash column chromatography (EtOAc:n-hexane=1:10) to give the compound 121 as a light-yellow solid (yield: 91%, 231 mg). [0302] 1H NMR (CDCl3, 300 MHz) delta 10.07 (s, 1H), 7.59 (d, J=8.6 Hz, 1H), 6.61 (d, J=8.6 Hz, 1H), 6.53 (d, J=10.0 Hz, 1H), 5.63 (d, J=10.0 Hz, 1H), 5.02 (s, 2H), 3.52 (s, 3H).

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetone; for 3h;	Preparation example 1> Preparation of 5-benzovloxy-22-dimethvl-6-Formyl- 2H-l-benzopyran 2, 2-dimethyl-6-formyl-5-hydroxy-2H-1-benzopyran (2.04 gr, 10.0 mmol) synthesized according to the reference (Clarke, D. , Crombie, L., Whiting, D. A., J. Chem. , Chem. Comm., 1973, 580p-582p), benzoyl chloride (1. 48 gr, 10.5 mmol) and K2CO3 (1. 38 gr, 10.0 mmol) were dissolved in acetone (30 mL) and stirred for 3 hours. The solution was filtered to remove salt, the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with brine, then dried over anhydrous MgS04 and concentrated under reduced pressure to give 5-benzoyloxy-2, 2-dimethyl-6-Formyl- 2H-l-benzopyran (3.08 g, 10.0 mmol). 'H-NMR (CDCl3) : 9.92 (s, 1H), 8. 25 (d, 2H), 7.71 (d, 2H), 7.70 (t, 1H), 7.55 (t, 2H), 6.83 (d, 1H), 6.38 (d, 1H), 5.69 (d, 1H), 1.49 (s, 6H)
2.51 g	With triethylamine; In dichloromethane; at 20℃; for 5h;	5-hydroxy-2,2-dimethyl-2H-benzimidazole was prepared according to the teachings of [Tetrahedron, 57 (2001), 5335-5338] (10.0 mmol) of this compound was dissolved in 20 ml of methylene chloride and the solution was stirred at room temperature for 5 hours and 1 ml of TEA was combined with 1.54 g (11.0 mmd ) Of benzoyl chloride. 10 ml of saturated aqueous sodium bicarbonate solution was added and stirred for an additional 10 minutes to separate the monohydrate layer from an organic layer. The separated aqueous layer was further extracted with 10 ml of dichloromethane, and the extract was combined with the organic layer and treated with magnesium sulfate and filtered, and the filtrate was concentrated. The concentrated solid was recrystallized from isopropyl alcohol (IPA) to give 2.51 g (8.1 mmol) of pure 6-formyl-2,2-dimethyl-2H-chromen-5-yl benzoate.
2.51 g	With triethylamine; In dichloromethane; at 20℃; for 5h;	Preparation Example 3 Synthesis of 6-formyl-2,2-dimethyl-2H-chromen-5-yl benzoate (0094) <strong>[54287-99-9]5-hydroxy-2,2-dimethyl-2H-chromen-6-carbaldehyde</strong> was prepared in accordance with the method of [Tetrahedron, 57 (2001), 53355338], and then 2.04 g (10.0 mmol) of the compound was dissolved in 20 ml of CH2Cl2, and the resulting solution was stirred at room temperature for 5 hours while 1 ml of TEA and 1.54 g (11.0 mmol) of benzoyl chloride were added thereto. 10 ml of a NaHCO3 saturated aqueous solution was added thereto, the resulting solution was stirred for another 10 min, and an aqueous layer and an organic layer were separated. The separated aqueous layer was further extracted using 10 ml of CH2Cl2, the extract was combined with the organic layer, the resulting mixture was combined with the organic layer and treated with MgSO4 and filtered, and the filtrate was concentrated. The solid thus concentrated was recrystallized using isopropyl alcohol (IPA) to obtain 2.51 g (8.1 mmol) of pure 6-formyl-2,2-dimethyl-2H-chromen-5-yl benzoate. (0095) 1H-NMR (CDCl3): 9.92 (s, 1H), 8.25 (m, 2H), 7.71 (d, 1H), 7.68 (m, 1H), 7.55 (t, 2H), 6.83 (d, 1H), 6.38 (d, 1H), 5.69 (d, 1H), 1.49 (s, 6H).

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

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[ 54287-99-9 ] Synthesis Path-Upstream 1~9

[ 54287-99-9 ] Synthesis Path-Downstream 1~88

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