[ CAS No. 90389-91-6 ] {[proInfo.proName]}

Name: 90389-91-6|N-Ethyl-3-bromobenzylamine|97%
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SKU: A683057
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Quality Control of [ 90389-91-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 90389-91-6 ]

CAS No. :	90389-91-6	MDL No. :	MFCD07405019
Formula :	C₉H₁₂BrN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZKUHSZJORZCOFE-UHFFFAOYSA-N
M.W :	214.10	Pubchem ID :	457589
Synonyms :

Calculated chemistry of [ 90389-91-6 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	3
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	51.52
TPSA :	12.03 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-9.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.57
Log Po/w (XLOGP3) :	-2.9
Log Po/w (WLOGP) :	2.41
Log Po/w (MLOGP) :	2.91
Log Po/w (SILICOS-IT) :	2.84
Consensus Log Po/w :	1.56

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	0.45
Solubility :	609.0 mg/ml ; 2.84 mol/l
Class :	Highly soluble
Log S (Ali) :	3.21
Solubility :	344000.0 mg/ml ; 1610.0 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-4.5
Solubility :	0.00669 mg/ml ; 0.0000313 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.3

Safety of [ 90389-91-6 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P301+P310	UN#:	2810
Hazard Statements:	H301	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 90389-91-6 ]

* 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 [ 90389-91-6 ]

[ 90389-91-6 ] Synthesis Path-Downstream 1~12

1
[ 110079-37-3 ]
[ 90389-91-6 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride In diethyl ether for 2h; Heating;
	With sodium tetrahydroborate In methanol

Reference： [1]Meindl; Von Angerer; Schonenberger; Ruckdeschel [Journal of Medicinal Chemistry, 1984, vol. 27, # 9, p. 1111 - 1118]
[2]Cho, Bong Rae; Maeng, Jun Ho; Yoon, Jong Chan; Kim, Tae Rin [Journal of Organic Chemistry, 1987, vol. 52, # 21, p. 4752 - 4756]

Yield	Reaction Conditions	Operation in experiment
	/BRN= 2689601/;

3
[ 3132-99-8 ]
[ 90389-91-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1 h / Ambient temperature 2: LiAlH₄ / diethyl ether / 2 h / Heating

Reference： [1]Meindl; Von Angerer; Schonenberger; Ruckdeschel [Journal of Medicinal Chemistry, 1984, vol. 27, # 9, p. 1111 - 1118]

4
[ 10061-01-5 ]
[ 90389-91-6 ]
[ 134865-57-9 ]

Yield	Reaction Conditions	Operation in experiment
64%	In ethyl acetate; N,N-dimethyl-formamide	9 (E)-N-(3-Chloro-2-propenyl)-N-ethyl-3-bromobenzylamine EXAMPLE 9 (E)-N-(3-Chloro-2-propenyl)-N-ethyl-3-bromobenzylamine To a solution of 4.28 g (20 mmol) of N-ethyl-3-bromobenzylamine in 30 ml of N,N-dimethylformamide were added 2.44 g (22 mmol) of 1,3-dichloropropene and 1.70 g (12 mmol) of ground potassium carbonate under ice cooling. The mixture was stirred for 8 hours at 60° C., poured into 40 ml of ethyl acetate, washed with 40 ml*2 of water and 40 ml of saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel chromatography (n-hexane→n-hexane/ethyl acetate=9/1). The desired fractions were put together and concentrated under reduced pressure to obtain 3.70 g (yield: 64%) of the above identified compound as an oil. IR(KBr)cm-1: 2970, 2800, 1570, 1430, 1360, 1070, 930, 780, 670. NMR(CDCl3)δ: 104(3 H, t, 7 Hz), 2.52(2 H, q, 7 Hz), 3.09(2 H, d, 7 Hz), 3.54(2 H, s), 5.98(1 H, dt, 14 Hz, 7 Hz), 6.13(1 H, d, 14 Hz), 7.1-7.6(3 H, m).

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US5231183, 1993, A

5
[ 823-78-9 ]
[ 75-04-7 ]
[ 90389-91-6 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol at 20℃;	1 To 80% ethylamine/MeOH (1.1 g) was added 1-bromo-3-(bromomethyl)benzene (1 g) in five divided portions at room temperature, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the obtained residue was subjected to liquid separation with chloroform and a saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated, and then the aqueous layer was extracted with CHCl3 again. These organic layers were combined, dried over Na2SO4, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH silica, 3% MeOH/CHCl3) to obtain N-(3-bromobenzyl)ethanamine (610 mg) as a colorless oil.
	In methanol at 20℃; for 4h;	Step 1: N-(3-bromobenzyl)ethanamine (B63) To a solution of 1-bromo-3-(bromomethyl)benzene (B62, 10g, 40.0 mmol) in MeOH (100 mL) was added ethanamine (18.04 g, 400 mmol) and the reaction was stirred at ambient temperature for 4 h. TLC showed formation of a new spot. The reaction was concentrated to afford N-(3-bromobenzyl)ethanamine (B63), which was carried forward without purification.

Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - US2012/184520, 2012, A1 Location in patent: Page/Page column 16
[2]Current Patent Assignee: HURZY DANIELLE M; MANLEY PETER J; ARMACOST KIRA A; MERCK & CO INC; RADA VANESSA L; KERN JEFFREY C; STUMP CRAIG A; RUDD MICHAEL T - WO2022/94012, 2022, A1 Location in patent: Page/Page column 136

6
C₁₇H₁₅N₂O₅PolS [ No CAS ]
[ 90389-91-6 ]
C₂₆H₂₇BrN₃O₄PolS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: C₁₇H₁₅N₂O₅PolS; N-(3-bromobenzyl)ethanamine With acetic acid In 1-methyl-pyrrolidin-2-one for 0.166667h; Stage #2: With sodium tris(acetoxy)borohydride In 1-methyl-pyrrolidin-2-one at 20℃; for 18h;

Reference： [1]Ouellet, Etienne; Maltais, Rene; Ouellet, Charles; Poirier, Donald [MedChemComm, 2013, vol. 4, # 4, p. 681 - 692]

7
C₁₇H₁₅N₂O₅PolS [ No CAS ]
[ 90389-91-6 ]
C₂₆H₂₇BrN₃O₄PolS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: C₁₇H₁₅N₂O₅PolS; N-(3-bromobenzyl)ethanamine With acetic acid In 1-methyl-pyrrolidin-2-one for 0.166667h; Stage #2: With sodium tris(acetoxy)borohydride In 1-methyl-pyrrolidin-2-one at 20℃; for 18h;

Reference： [1]Ouellet, Etienne; Maltais, Rene; Ouellet, Charles; Poirier, Donald [MedChemComm, 2013, vol. 4, # 4, p. 681 - 692]

8
[ 90389-91-6 ]
ethyl 2-(2-((7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-5-yl)methoxy)phenyl)acetate [ No CAS ]
ethyl 2-(2-((7-(3-((ethylamino)methyl)phenyl)benzofuran-5-yl)methoxy)phenyl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane; water at 135℃; for 0.5h; Inert atmosphere; Microwave irradiation;	4; 1 Step-4: Preparation of ethyl 2-(2-((7-(5-formylthiophen-3-yl)benzofuran-5- yl)methoxy)phenyl)acetate (If) General procedure: To a degassed solution of ethyl 2-(2-((7-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)benzofuran-5-yl)methoxy)phenyl)acetate (le) (2 g, 4.58 mmol) in dioxane (24 mL) was added 4-bromothiophene-2-carbaldehyde (0.876 g, 5.01 mmol), bis(triphenylphosphine)Palladium(II)chloride [Pd(PPh3)2Cl2] (0.527 g, 0.751 mmol), a solution of K2CO3 (2.076 g, 15.02 mmol) in water (8 mL) and heated at 90 °C for 3 h on oil bath under a nitrogen atmosphere. The reaction mixture was cooled to room temperature diluted with EtOAc (100 mL) and water (15 mL). The organic layer was separated, and aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layers were dried, filtered and evaporated to dryness. The residue obtained was purified by flash column chromatography [silica gel 12 g, eluting with DMA-80 in DCM from 0-50%] to give ethyl 2- (2-((7-(5-formylthiophen-3-yl)benzofuran-5-yl)methoxy)phenyl)acetate (If) (2.022 g, 100 % yield) as a yellow syrup. NMR (300 MHz, DMSO-7e) 5 10.11 - 10.02 (m, 1H), 8.70 (s, 2H), 7.83 (d, 7 = 1.6 Hz, 1H), 7.72 (d, 7 = 1.6 Hz, 1H), 7.30 - 7.25 (m, 1H), 7.25 - 7.21 (m, 2H), 7.14 - 7.09 (m, 1H), 7.08 (d, 7 = 2.2 Hz, 1H), 6.92 (td, 7 = 7.4, 1.1 Hz, 1H), 5.24 (s, (0171) 2H), 3.98 - 3.92 (m, 2H), 3.65 (s, 2H), 1.00 (t, 7= 7.1 Hz, 3H).

Reference： [1]Current Patent Assignee: BIOCRYST PHARMACEUTICALS INC - WO2021/72156, 2021, A1 Location in patent: Page/Page column 88; 90; 147-148

9
[ 90389-91-6 ]
tert-butyl ethyl((2'-methoxy-[1,1'-biphenyl]-3-yl)methyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere

10
[ 24424-99-5 ]
[ 90389-91-6 ]
tert-butyl (3-bromobenzyl)(ethyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;	S1.2. General procedure for the synthesis of compounds 6a-6c General procedure: The mixture of compound 5 (1.00 mmol), 2M di-tert-butyl dicarbonate solution in THF (1.20 mmol) and triethylamine (1.20 mmol) in THF (10 ml) were stirred at room temperature for 2 h. The mixture was stirred at room temperature for overnight. The reaction mixture was quenched with saturated aqueous NaHCO3 solution, and then the aqueous layer was extracted with DCM three times. The combined organic layers were dried over anhydrous MgSO4, filtered, and evaporated. The residue was purified by column chromatography on silica gel (Hexane: Ethyl acetate = 10: 1) to obtain desired products 6. tert-Butyl (3-bromobenzyl)(ethyl)carbamate 6a 92% Yield; 1H NMR (400 MHz, CDCl3) δ 7.42 - 7.35 (m, 2H), 7.23 - 7.14 (m, 2H), 4.39 (s, 2H), 3.35 - 3.11 (m, 2H), 1.49 - 1.42 (m, 9H), 1.08 (t, J = 7.3 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 146.69, 141.25, 130.09, 129.99, 122.45, 85.00, 79.64, 49.19, 41.53, 27.30, 13.16
	With triethylamine In dichloromethane at 20℃; for 16h;	Step 2: tert-butyl (3-bromobenzyl)(ethyl)carbamate (B64) To a solution of N-(3-bromobenzyl)ethanamine (B63, 8.57 g, 40.0 mmol) in DCM (100 mL) were added TEA (16.74 mL, 120 mmol) and Boc anhydride (17.5 g, 80 mmol). The reaction was stirred at ambient temperature for 16 h. LCMS showed formation of the desired product mass. The reaction was poured into water (200 mL) and extracted with DCM (3 × 50 mL). The combined organic layers were washed with brine (100 mL), dried (Na2SO4), filtered and concentrated. The crude material was purified by flash silica chromatography (0 - 10% EtOAc in petroleum ether gradient) to give tert-butyl (3-bromobenzyl)(ethyl)carbamate (B64). LC-MS: 258.1, 260.1 (M+1-tBu).1H NMR: (400 MHz, CDCl3) δ 7.37-7.10 (m, 4H), 4.37 (br s, 2H), 3.38-3.06 (m, 2H), 1.49-1.40 (m,9H), 1.14-1.00 (m, 3H).

Reference： [1]Kim, Doyoung; Lee, Jieon; Kwag, Rina; Kim, Hyunbin; Oh, Hyunji; Moon, Bongjin; Kim, Hak Joong; Seong, Jihye; Jeon, Byungsun; Kang, Taek; Choo, Hyunah [Bulletin of the Korean Chemical Society, 2022, vol. 43, # 1, p. 73 - 77]
[2]Current Patent Assignee: HURZY DANIELLE M; MANLEY PETER J; ARMACOST KIRA A; MERCK & CO INC; RADA VANESSA L; KERN JEFFREY C; STUMP CRAIG A; RUDD MICHAEL T - WO2022/94012, 2022, A1 Location in patent: Page/Page column 136

11
[ 3132-99-8 ]
[ 75-04-7 ]
[ 90389-91-6 ]

Yield	Reaction Conditions	Operation in experiment
67%	Stage #1: m-bromobenzoic aldehyde; ethylamine With acetic acid In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20℃; Inert atmosphere;	S1.1. General procedure for the synthesis of compounds 5a-5c General procedure: The mixture of compound 4 (1.00 mmol), 2M ethylamine solution in THF (2.00 mmol) and acetic acid (1.00 mmol) in THF (10 ml) were stirred at room temperature for 2 h and then NaBH(OAc)3 (3.00 mmol) was added. The mixture was stirred at room temperature for overnight. The reaction mixture was quenched with saturated aqueous NaHCO3 solution, and then the aqueous layer was extracted with DCM three times. The combined organic layers were dried over anhydrous MgSO4, filtered, and evaporated. The residue was purified by column chromatography on silica gel (DCM: Hexane = 10: 1) to obtain desired products 5. N-(3-Bromobenzyl)ethanamine 5a 67% Yield; 1H NMR (400 MHz, CDCl3) δ 7.49 (t, J = 1.8 Hz, 1H), 7.37 (dt, J = 7.7, 1.6 Hz, 1H), 7.28 - 7.21 (m, 1H), 7.18 (t, J = 7.7 Hz, 1H), 3.77 (s, 2H), 2.67 (q, J = 7.1 Hz, 2H), 1.13 (t, J = 7.1 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 142.82, 131.15, 130.00, 129.95, 126.73, 122.54, 53.28, 43.62, 15.23

12
[ 90389-91-6 ]
tert-butyl ethyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 16 h / 20 °C 2: anhydrous potassium acetate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / 1,4-dioxane / 5 h / 80 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: HURZY DANIELLE M; MANLEY PETER J; ARMACOST KIRA A; MERCK & CO INC; RADA VANESSA L; KERN JEFFREY C; STUMP CRAIG A; RUDD MICHAEL T - WO2022/94012, 2022, A1

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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.
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Prevention
Code	Phrase
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Code	Phrase
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
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P401
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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

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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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

[ CAS No. 90389-91-6 ] {[proInfo.proName]}

Quality Control of [ 90389-91-6 ]

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Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 90389-91-6 ]

[ 90389-91-6 ] Synthesis Path-Downstream 1~12

Related Functional Groups of [ 90389-91-6 ]

Aryls

Bromides

Amines

Precautionary Statements-General

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Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 90389-91-6 ]