54013-06-8|Ethyl 5-aminopyrazine-2-carboxylate| Ambeed

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Quality Control of [ 54013-06-8 ] Purity: 98% SDS Specification

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Product Details of [ 54013-06-8 ]

CAS No. :	54013-06-8
Formula :	C₇H₉N₃O₂
M.W :	167.17
SMILES Code :	NC1=CN=C(C=N1)C(=O)OCC
MDL No. :	MFCD08437665
InChI Key :	BLPDHDYKCBRILY-UHFFFAOYSA-N
Pubchem ID :	22271413

Safety of [ 54013-06-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 54013-06-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.29
Num. rotatable bonds	3
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	42.52
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	78.1 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.36
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	-0.07
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.24
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-0.68
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.32
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.23

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.0
Solubility	16.6 mg/ml ; 0.099 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.12
Solubility	12.7 mg/ml ; 0.0761 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.77
Solubility	2.86 mg/ml ; 0.0171 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.37 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.13

Application In Synthesis of [ 54013-06-8 ]

* 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 [ 54013-06-8 ]

[ 54013-06-8 ] Synthesis Path-Downstream 1~35

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Yield	Reaction Conditions	Operation in experiment
12%; 20%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at 20℃;	Example 15 5-[3-(4-Fluoro-phenyl)-2-(4-methanesulfonyl-phenyl)-propionylamino]-pyrazine-2-carboxylic acid ethyl ester To a suspension of a mixture of <strong>[54013-06-8]5-amino-pyrazine-2-carboxylic acid ethyl ester</strong> and 5-amino-pyrazine-2-carboxylic acid methyl ester (approximately 2:1) in CH2Cl2 (40 mL) was added DIEA (1.04 mL, 6 mmol) and DMF (5 mL). To the resulting suspension was added 3-(4-fluorophenyl)-2-(4-methanesulfonylphenyl)propionic acid (prepared as described in example 14, 1.5 g, 4.7 mmol), DMAP (0.17 g, 1.4 mmol) and EDC.HCl (1.08 g, 5.6 mmol) followed by additional CH2Cl2 (10 mL) and DMF (6 mL). The resulting solution was stirred at room temperature overnight. The reaction mixture was poured onto 0.01% aqueous HCl and extracted 3 times into CH2Cl2. The combined organic layer was dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (silica, 30%-50% ethyl acetate/hexanes stepwise gradient), followed by re-purification of the mixed fractions by chromatography (50% ethyl acetate/hexanes) afforded the front-running product, 5-[3-(4-fluorophenyl)-2-(4-methanesulfonylphenyl)-propionylamino]-pyrazine-2-carboxylic acid ethyl ester (438 mg, 20%): m.p. 99-100 C., LC/MS-ESI observed [M+H]+ 472; and the back-running product, 5-[3-(4-fluoro-phenyl)-2-(4-methanesulfonylphenyl)propionylamino]-pyrazine-2-carboxylic acid methyl ester (260 mg, 12%): m.p. 106-107 C., LC/MS-ESI observed [M+H]+ 458.

References: [1]Patent: US2012/149718,2012,A1 .Location in patent: Page/Page column 33.

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[ 1447364-35-3 ]

Yield	Reaction Conditions	Operation in experiment
69 mg	With N-ethyl-N,N-diisopropylamine; at 120℃;Molecular sieve;	Intermediate Example lnt-5: Ethyl 2-(4-{1-[(ferf-butoxycarbonyl)amino]cyclobutyl}phenyl)-3-phenyl- imidazo[1,2-a]pyrazine-6-carboxylate To a mixture of crude fert-butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)- carbamate [lnt-1-A] (213 mg, 0.38 mmol, 1.0 eq), ethyl 5-aminopyrazine-2- carboxylate (CAS-Nr. 54013-06-8, 70.5 mg, 0.42 mmol, 1.1 eq.) and diisopropylethylamine (0.055 ml_, 0.42 mmol, 1.1 eq) in 2.3 ml_ butyronitrile was added pre- dried 3A mol sieves. The mixture was heated overnight at 120. The reaction mixture was partitioned between DCM/water and was filtered through a phase separator. The remaining volatile organic components were removed by the use of a rotary evaporator. In parallel we conducted the same experiment in the absence of diisopropylethylamine following the same protocol. The crude materials of both experiments were combined and purified via MPLC (Biotage Isolera, 25 g Snap- cartridge; eluent: hexane/ethyl acetate (1/1) -> ethyl acetate) to deliver 69 mg (14%, yield based on combined amount of fert-butyl (1-{4-[bromo(phenyl)acetyl]- phenyl}cyclobutyl)carbamate) of the title compound. UPLC-MS (Method 1): RT = 1.43 min; m/z = 513 (M+H) +.

References: [1]Patent: WO2013/104610,2013,A1 .Location in patent: Page/Page column 53-54.

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[ 1447364-26-2 ]

Yield	Reaction Conditions	Operation in experiment
38 mg	at 120℃; for 1.5h;	Example 5: Ethyl 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2- a razine-6-carboxylate To a mixture of crude fert-butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)- carbamate [lnt-1-A] (245 mg, 0.44 mmol, 1.0 eq) and ethyl 5-aminopyrazine-2- carboxylate (CAS-Nr. 54013-06-8, 81.1 mg, 0.49 mmol, 1.1 eq.) in 2.7 mL bu- tyronitrile was heated at 120 for 1.5h. A substan tial amount of the deprotected free amine was detected by UPLC analysis. For isolation, the volatile components were removed using a rotary evaporator and the resulting crude material was purified via MPLC [Biotage Isolera, 25 g Snap-cartridge; eluent: DCM -> DCM/ethanol (95/5)] to deliver 38 mg (21 %) of the title compound. UPLC-MS (Method 1): RT = 0.90 min; m/z = 414 (M+H)+. 1H-NMR (400 MHz, DMSO-d6): delta [ppm] = 1.26 (t, 3H), 1.60 (m, 1 H), 1.88-2.07 (m, 3H), 2.12 (s br, 2H), 2.26-2.37 (m, 2H), 4.30 (q, 2H), 7.39 (d, 2H), 7.57(d, 4H), 7.60-7.68 (m, 3H).

References: [1]Patent: WO2013/104610,2013,A1 .Location in patent: Page/Page column 59-60.

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References: [1]Patent: WO2014/78813,2014,A1 .

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References: [1]Patent: WO2014/78813,2014,A1 .

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[ 54013-06-8 ]
3-{4-[(2S)-2-amino-2-cyclohexylacetamido]phenyl}-N-(4-cyanophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide trifluoroacetate [ No CAS ]

References: [1]Patent: WO2014/78813,2014,A1 .

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References: [1]Patent: WO2014/78813,2014,A1 .

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References: [1]Patent: WO2014/78813,2014,A1 .
[2]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 947 - 950.

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References: [1]Patent: WO2014/78813,2014,A1 .

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References: [1]Patent: WO2014/78813,2014,A1 .
[2]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 947 - 950.

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[ 1607829-61-7 ]

References: [1]Patent: WO2014/78813,2014,A1 .
[2]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 947 - 950.

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[ 1607830-85-2 ]

References: [1]Patent: WO2014/78813,2014,A1 .
[2]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 947 - 950.

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[ 1607830-85-2 ]
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References: [1]Patent: WO2014/78813,2014,A1 .

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References: [1]Patent: WO2014/78813,2014,A1 .
[2]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 947 - 950.

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[ 1610667-27-0 ]

References: [1]Patent: WO2014/78813,2014,A1 .
[2]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 947 - 950.

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References: [1]Patent: WO2014/78813,2014,A1 .
[2]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 947 - 950.

Historical Records

Technical Information

• Acyl Group Substitution • Bouveault-Blanc Reduction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Ester Cleavage • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

Related Functional Groups of
[ 54013-06-8 ]

Esters

A139536 [13924-94-2]

Methyl 5-aminopyrazine-2-carboxylate

Similarity: 0.96

A186991 [118853-60-4]

Methyl 6-aminopyrazine-2-carboxylate

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A137195 [6924-68-1]

Ethyl pyrazine-2-carboxylate

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A203314 [6164-79-0]

Methyl 2-pyrazinecarboxylate

Similarity: 0.85

A193813 [36070-83-4]

Ethyl 5-bromopyrazine-2-carboxylate

Similarity: 0.76

Amines

A139536 [13924-94-2]

Methyl 5-aminopyrazine-2-carboxylate

Similarity: 0.96

A186991 [118853-60-4]

Methyl 6-aminopyrazine-2-carboxylate

Similarity: 0.96

A155148 [61442-38-4]

6-Aminopyrazine-2-carboxylic acid

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A148219 [40262-53-1]

6-(Dimethylamino)pyrazine-2-carboxylic acid

Similarity: 0.73

A208317 [16298-03-6]

Methyl 2-aminopyrazine-3-carboxylate

Similarity: 0.71

Related Parent Nucleus of
[ 54013-06-8 ]

Pyrazines

A139536 [13924-94-2]

Methyl 5-aminopyrazine-2-carboxylate

Similarity: 0.96

A186991 [118853-60-4]

Methyl 6-aminopyrazine-2-carboxylate

Similarity: 0.96

A137195 [6924-68-1]

Ethyl pyrazine-2-carboxylate

Similarity: 0.89

A155148 [61442-38-4]

6-Aminopyrazine-2-carboxylic acid

Similarity: 0.85

A203314 [6164-79-0]

Methyl 2-pyrazinecarboxylate

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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

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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CAS No.: 54013-06-8

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