[ CAS No. 18791-75-8 ] {[proInfo.proName]}

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2D 3D

Structure of 18791-75-8 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 18791-75-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 18791-75-8 ]

SDS Specification

Alternatived Products of [ 18791-75-8 ]

Product Details of [ 18791-75-8 ]

CAS No. :	18791-75-8	MDL No. :	MFCD00005431
Formula :	C₅H₃BrOS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PDONIKHDXYHTLS-UHFFFAOYSA-N
M.W :	191.05	Pubchem ID :	87792
Synonyms :

Calculated chemistry of [ 18791-75-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	37.41
TPSA :	45.31 ?2

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) :	-5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.62
Log Po/w (XLOGP3) :	2.09
Log Po/w (WLOGP) :	2.32
Log Po/w (MLOGP) :	1.19
Log Po/w (SILICOS-IT) :	3.38
Consensus Log Po/w :	2.12

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.74
Solubility :	0.35 mg/ml ; 0.00183 mol/l
Class :	Soluble
Log S (Ali) :	-2.67
Solubility :	0.407 mg/ml ; 0.00213 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.47
Solubility :	0.647 mg/ml ; 0.00339 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.25

Safety of [ 18791-75-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 18791-75-8 ]

* 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.

Upstream synthesis route of [ 18791-75-8 ]
Downstream synthetic route of [ 18791-75-8 ]

[ 18791-75-8 ] Synthesis Path-Upstream 1~2

1
[ 18791-75-8 ]
[ 83933-17-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydroxylamine hydrochloride; caesium carbonate In water; dimethyl sulfoxide at 125℃; for 14 h;	General procedure: Aldehyde (0.5mmol), NH₂OH·HCl (0.6mmol) and Cs₂CO₃ (0.6mmol) were stirred at 125°C for 48h in a 3:1 mixture of DMSO–H₂O (2mL) under air. The progress of the reaction was monitored by TLC using ethyl acetate and hexane as eluent. After completion, the reaction mixture was cooled to room temperature and treated with water (1mL). The resulting mixture was extracted with ethyl acetate (3×5mL). Drying (Na₂SO₄) and evaporation of the solvent gave a residue that was purified on silica gel column chromatography using ethyl acetate and hexane. The purified products were identified by ¹H NMR spectra and the melting points comparison with the literature data.

Reference： [1] Tetrahedron Letters, 2014, vol. 55, # 20, p. 3192 - 3194
[2] RSC Advances, 2016, vol. 6, # 43, p. 37093 - 37098

2
[ 18791-75-8 ]
[ 1105187-36-7 ]

Reference： [1] Patent: EP2320906, 2016, B1,

[ 18791-75-8 ] Synthesis Path-Downstream 1~8

1
[ 18791-75-8 ]
[ 18791-99-6 ]

Yield	Reaction Conditions	Operation in experiment
95%		The 4 - bromo thiophene -2 - formaldehyde (600g, 3.14 muM) and hydroxylamine hydrochloride (438g, 6.30 muM) added to the pyridine (5L) in, heated to 90 C10 minutes after cooling down to room temperature, drop vinegar anhydride (1940g, 19.0 muM) heated to 80 C, reaction 1 hours, poured into water to (20L) in, stirring 30 minutes, filtered, drying to obtain the product (564g, yield 95%).
		A mixture of 4-bromothiophene-2-carbaldehyde, NH2OH.HCl, and K2CO3 in EtOH was refluxed overnight to form an oxime. The oxime was then dissolved in SOCl2 and the reacion mixture was stirred at room temperature for 2 hrs to yield crude 4-bromothiophene-2-carbonitrile. The crude 4-bromothiophene-2-carbonitrile was treated with NH2OH.HCl in the presence of Et3 N in EtOH at reflux overnight to form 4-bromo-N-hydroxythiophene-2-carboximidamide. The reaction was complete as followed by LC/MS.

Reference： [1]Patent: CN104230960,2017,B .Location in patent: Paragraph 0449; 0450; 0451
[2]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 415 - 418
[3]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2870 - 2875
[4]Patent: US2017/151225,2017,A1 .Location in patent: Paragraph 0926; 0927

2
[ 18791-75-8 ]
[ 17115-51-4 ]
[ 28566-12-3 ]
8-(4-bromo-2-thienyl)-2,3,4,5,6,8-hexahydro-7H-cyclopenta[b]thieno[2,3-e]pyridin-7-one, 1,1-dioxide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3163 - 3179

3
[ 18791-75-8 ]
[ 62224-16-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 491 - 495
[2]Journal of Medicinal Chemistry,1992,vol. 35,p. 1109 - 1116

4
[ 179898-22-7 ]
[ 18791-75-8 ]
hyroxylamine-O-sulfonic acid [ No CAS ]
[ 18791-99-6 ]

Yield	Reaction Conditions	Operation in experiment
0.50 g (51%)	With sodium hydroxide; In water; acetonitrile;	4-Bromo-2-cyanothiophene To a solution of 4-bromo-2-thiophenecarboxaldehyde (1.0 g, 5.2 mmol, Aldrich) in acetonitrile/water (20 mL/2 mL) was added hyroxylamine-O-sulfonic acid (2.4 g, 21.2 mmol, Aldrich). The dark solution was heated to 65 C. with stirring. After 8 h, the reaction was quenched with 10% NaOH (10 mL). The solution was extracted with EtOAc (30 mL). The organic layer was washed with water and brine (3*10 mL each), dried (Na2 SO4), and concentrated in vacuo to afford the crude product as a tan solid. The crude product was purified by silica flash chromatography (5-25% EtOAc:hexane) to afford 0.50 g (51%) of 4-bromo-2-cyanothiophene as a white solid.
0.50 g (51%)	With sodium hydroxide; In water; acetonitrile;	4-Bromo-2-cyanothiophene. To a solution of 4-bromo-2-thiophenecarboxaldehyde (1.0 g, 5.2 mmol, Aldrich) in acetonitrile/water (20 mL/2 mL) was added hyroxylamine-O-sulfonic acid (2.4 g, 21.2 mmol, Aldrich). The dark solution was heated to 65 C. with stirring. After 8 h, the reaction was quenched with 10% NaOH (10 mL). The solution was extracted with EtOAc (30 mL). The organic layer was washed with water and brine (3*10 mL each), dried (Na2 SO4), and concentrated in vacuo to afford the crude product as a tan solid. The crude product was purified by silica flash chromatography (5-25% EtOAc:hexane) to afford 0.50 g (51%) of 4-bromo-2-cyanothiophene as a white solid.

Reference： [1]Patent: US5696130,1997,A
[2]Patent: US5696133,1997,A

5
[ 18791-75-8 ]
hyroxylamine-O-sulfonic acid [ No CAS ]
[ 18791-99-6 ]

Yield	Reaction Conditions	Operation in experiment
0.50 g (51%)	With sodium hydroxide; In water; acetonitrile;	4-Bromo-2-cyanothiophene To a solution of 4-bromo-2-thiophenecarboxaldehyde (1.0 g, 5.2 mmol, Aldrich) in acetonitrile/water (20 mL/2 mL) was added hyroxylamine-O-sulfonic acid (2.4 g, 21.2 mmol, Aldrich). The dark solution was heated to 65 C. with stirring. After 8 h, the reaction was quenched with 10% NaOH (10 mL). The solution was extracted with EtOAc (30 mL). The organic layer was washed with water and brine (3*10 mL each), dried (Na2 SO4), and concentrated in vacuo to afford the crude product as a tan solid. The crude product was purified by silica flash chromatography (5-25% EtOAc:hexane) to afford 0.50 g (51%) of 4-bromo-2-cyanothiophene as a white solid.

Reference： [1]Patent: US5688808,1997,A

6
[ 18791-75-8 ]
[ 163520-14-7 ]
[ 956316-49-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 7166 - 7183

7
[ 18791-75-8 ]
[ 7504-94-1 ]
[ 1333991-78-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5266 - 5269

8
[ 18791-75-8 ]
[ 67-56-1 ]
[ 18791-99-6 ]
C₆H₆BrNOS [ No CAS ]

Reference： [1]Catalysis science and technology,2016,vol. 6,p. 7429 - 7436

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Chaykovsky Reaction ? Corey-Fuchs Reaction ? Fischer Indole Synthesis ? General Reactivity ? Grignard Reaction ? Hantzsch Dihydropyridine Synthesis ? Henry Nitroaldol Reaction ? Hiyama Cross-Coupling Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Julia-Kocienski Olefination ? Kinetics of Alkyl Halides ? Knoevenagel Condensation ? Kumada Cross-Coupling Reaction ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mukaiyama Aldol Reaction ? Nozaki-Hiyama-Kishi Reaction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Reformatsky Reaction ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Stetter Reaction ? Stille Coupling ? Stobbe Condensation ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

Historical Records

Related Functional Groups of
[ 18791-75-8 ]

Bromides

[ 930-96-1 ]

3-Bromothiophene-2-carboxaldehyde

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[ 16694-18-1 ]

4-Bromo-2-thiophenecarboxylic acid

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[ 83933-17-9 ]

4-Bromothiophene-2-carboxamide

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[ 29421-99-6 ]

4-Bromo-5-methylthiophene-2-carboxylic acid

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[ 62224-16-2 ]

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Aldehydes

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Thiophene-2-carbaldehyde

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[ 13679-70-4 ]

5-Methylthiophene-2-carbaldehyde

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P102	Keep out of reach of children.
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Prevention
Code	Phrase
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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.
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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.
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P251	Pressurized container: Do not pierce or burn, even after use.
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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.
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P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P285	In case of inadequate ventilation wear respiratory protection.
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P235 + P410	Keep cool. Protect from sunlight.
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Code	Phrase
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P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
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P308	IF exposed or concerned:
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P311	Call a POISON CENTER or doctor/physician.
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P321
P322
P330	Rinse mouth.
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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.
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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
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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
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P401
P402	Store in a dry place.
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P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
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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.
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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
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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
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H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
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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
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H351	Suspected of causing cancer
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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. 18791-75-8 ] {[proInfo.proName]}

Quality Control of [ 18791-75-8 ]

Related Doc. of [ 18791-75-8 ]

Product Details of [ 18791-75-8 ]

Calculated chemistry of [ 18791-75-8 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 18791-75-8 ]

Application In Synthesis of [ 18791-75-8 ]

[ 18791-75-8 ] Synthesis Path-Upstream 1~2

[ 18791-75-8 ] Synthesis Path-Downstream 1~8

Technical Information

Related Functional Groups of [ 18791-75-8 ]

Bromides

Aldehydes

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 18791-75-8 ]