[ CAS No. 589-15-1 ] {[proInfo.proName]}

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Quality Control of [ 589-15-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 589-15-1 ]

SDS Specification

Alternatived Products of [ 589-15-1 ]

Product Citations Expand+

Highly compressible glass-like supramolecular polymer networks

Zehuan Huang ; Xiaoyi Chen ; Stephen J. K. O’Neill , et al. Nat. Mater.,2022,21(1):103-109. DOI: 10.1038/s41563-021-01124-x PubMed ID: 34819661

Abstract: Supramolecular polymer networks are non-covalently crosslinked soft materials that exhibit unique mechanical features such as self-healing, high toughness and stretchability. Previous studies have focused on optimizing such properties using fast-dissociative crosslinks (that is, for an aqueous system, dissociation rate constant kd?>?10?s?1). Herein, we describe non-covalent crosslinkers with slow, tuneable dissociation kinetics (kd?

Purchased from AmBeed: 2243-54-1 ; 17201-43-3 ; 589-15-1 ; 106797-53-9 ; 622-95-7 ; 16004-15-2 ; 7646-67-5

Structure-activity studies of PTPRD phosphatase inhibitors identify a 7-cyclopentymethoxy illudalic acid analog candidate for development

Henderson, Ian M. ; Zeng, Fanxun ; Bhuiyan, Nazmul H. , et al. Biochem. Pharmacol.,2022,195,114868. DOI: 10.1016/j.bcp.2021.114868 PubMed ID: 34863978

Abstract: Interest in development of potent, selective inhibitors of the phosphatase from the receptor type protein tyrosine phosphatase PTPRD as antiaddiction agents is supported by human genetics, mouse models and studies of our lead compound PTPRD phosphatase inhibitor, 7-butoxy illudalic acid analog 1 (7-BIA). We now report structure-activity relationships for almost 70 7-BIA-related compounds and results that nominate a 7- cyclopentyl methoxy analog as a candidate for further development. While efforts to design 7-BIA analogs with substitutions for other parts failed to yield potent inhibitors of PTPRDs phosphatase, ten 7-position substituted analogs displayed greater potency at PTPRD than 7-BIA. Several were more selective for PTPRD vs the receptor type protein tyrosine phosphatases S, F and J or the nonreceptor type protein tyrosine phosphatase N1 (PTPRS, PTPRF, PTPRJ or PTPN1/PTP1B), phosphatases at which 7-BIA displays activity. In silico studies aided design of novel analogs. A 7-position cyclopentyl methoxy substituted 7-BIA analog termed NHB1109 displayed 600-700 nM potencies in inhibiting PTPRD and PTPRS, improved selectivity vs PTPRS, PTPRF, PTPRJ or PTPN1/PTP1B phosphatases, no substantial potency at other protein tyrosine phosphatases screened, no significant potency at any of the targets of clin.-useful drugs identified in EUROFINS screens and significant oral bioavailability. Oral doses up to 200 mg/kg were well tolerated by mice, though higher doses resulted in reduced weight and apparent ileus without clear organ histopathol. NHB1109 provides a good candidate to advance to in vivo studies in addiction paradigms and toward human use to reduce reward from addictive substances.

Keywords: Receptor type protein tyrosine phosphatase ; Cell adhesion molecule ; Addiction ; Drug reward ; Opiates ; Stimulants

Purchased from AmBeed: 37595-74-7 ; 637-59-2 ; 103-63-9 ; 64473-35-4 ; 20443-99-6 ; 939-26-4 ; 3814-32-2 ; 3814-30-0 ; 36881-42-2 ; 17247-58-4 ; 589-15-1 ; 2550-36-9 ; 7051-34-5 ; 161043-38-5 ; 161395-96-6 ; 59311-24-9 ; 78358-86-8 ; 83642-03-9 ...More

Product Details of [ 589-15-1 ]

CAS No. :	589-15-1	MDL No. :	MFCD00000179
Formula :	C₇H₆Br₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	YLRBJYMANQKEAW-UHFFFAOYSA-N
M.W :	249.93	Pubchem ID :	68527
Synonyms :		Chemical Name :	1-Bromo-4-(bromomethyl)benzene

Calculated chemistry of [ 589-15-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	46.98
TPSA :	0.0 ?2

Pharmacokinetics

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.26 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.42
Log Po/w (XLOGP3) :	3.61
Log Po/w (WLOGP) :	3.19
Log Po/w (MLOGP) :	3.83
Log Po/w (SILICOS-IT) :	3.53
Consensus Log Po/w :	3.32

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.09
Solubility :	0.0203 mg/ml ; 0.0000811 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.3
Solubility :	0.126 mg/ml ; 0.000504 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.51
Solubility :	0.00771 mg/ml ; 0.0000308 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.53

Safety of [ 589-15-1 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P501-P260-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405	UN#:	3261
Hazard Statements:	H314-H290	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 589-15-1 ]

* 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.

Upstream synthesis route of [ 589-15-1 ]
Downstream synthetic route of [ 589-15-1 ]

[ 589-15-1 ] Synthesis Path-Upstream 1~3

1
[ 288-32-4 ]
[ 589-15-1 ]
[ 72459-46-2 ]

Reference： [1] New Journal of Chemistry, 2004, vol. 28, # 8, p. 1010 - 1018
[2] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 4, p. 1992 - 2010
[3] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276
[4] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 2, p. 178 - 182
[5] Journal of Medicinal Chemistry, 2004, vol. 47, # 24, p. 5995 - 6008
[6] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 16, p. 6184 - 6196
[7] Journal of Medicinal Chemistry, 2010, vol. 53, # 4, p. 1712 - 1725
[8] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 15, p. 4011 - 4015
[9] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 18, p. 4752 - 4756
[10] European Journal of Medicinal Chemistry, 2016, vol. 122, p. 684 - 701
[11] ChemistryOpen, 2016, vol. 5, # 6, p. 566 - 573

2
[ 589-15-1 ]
[ 90562-10-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 9, p. 3874 - 3883

3
[ 589-15-1 ]
[ 481054-89-1 ]

Reference： [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 9, p. 1463 - 1467
[2] Organic and Biomolecular Chemistry, 2013, vol. 11, # 9, p. 1463 - 1467

[ 589-15-1 ] Synthesis Path-Downstream 1~11

1
[ 4054-67-5 ]
[ 589-15-1 ]
[ 101161-36-8 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1985,vol. 33,p. 2535 - 2540

2
[ 2346-26-1 ]
[ 589-15-1 ]
[ 728951-53-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; at 20℃;	A solution of 1.50 g (6 mmol) of 4-bromobenzyl bromide and 0.73 g (7.2 mmol) of 1,3-<strong>[2346-26-1]oxazolidine-2,4-dione</strong> in 6 ml of tetrahydrofuran is admixed dropwise with a solution of 1.39 g (12 mmol) of 1,1,3,3-tetramethylguanidine in 6 ml of tetrahydrofuran. The mixture is stirred at ambient temperature overnight. 50 ml of ice-cold aqueous hydrochloric acid (1N) and 100 ml of ethyl acetate are added. The organic phase is separated after settling out and washed successively with 25 ml of water and 25 ml of saturated aqueous sodium chloride solution. It is dried over sodium sulphate and the filtrate is concentrated under reduced pressure. The residue is purified by chromatography on silica gel, eluting with an 80/20 mixture of cyclohexane and ethyl acetate. 1.14 g of product are obtained in the form of white crystals. m.p. ( C.): 88-90 C.

Reference： [1]Patent: US2006/14830,2006,A1 .Location in patent: Page/Page column 12

3
[ 589-15-1 ]
[ 75476-86-7 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 4226 - 4237

4
[ 589-15-1 ]
[ 205383-87-5 ]
[ 1426689-29-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1860 - 1864

5
[ 619-60-3 ]
[ 589-15-1 ]
4-(4-bromobenzyloxy)-N,N-dimethylaniline [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 6030 - 6042

6
[ 619-60-3 ]
[ 589-15-1 ]
N,N-dimethyl-4-((4-(tributylstannyl)benzyl)oxy)aniline [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 6030 - 6042

7
[ 42726-73-8 ]
[ 589-15-1 ]
1-tert-butyl 3-methyl 2-(4-bromobenzyl)malonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%		A 100 mL round-bottom flask equipped with a stirring bar was charged with compound 7 (1000 mg, 5.8 mmol) and DMF (20 mL). To the solution, sodium hydride (60percent oil suspension, 233 mg, 5.8 mmol) was added. The reaction was allowed to stir at 0 °C for 1 h. To the mixture, 4-bromobenzyl bromide (1437 mg, 5.8 mmol) was added at 0 °C and the mixture was stirred at room temperature for 20 h. To the reaction mixture, H2O was added, and the mixture was extracted with CH2Cl2 (3x), dried over MgSO4, and concentrated in vacuo. The remaining residue was purified by silica gel column chromatography (hexanes/AcOEt = 90:10) to afford the desired product 4 (1551 mg, 79percent) as a colorless oil. 1H NMR (400 MHz, CDCl3) delta 7.39 (d, J = 8.3 Hz, 2H), 7.08 (d, J = 8.3 Hz, 2H), 3.70 (s, 3H), 3.53 (t, J = 7.8 Hz, 1H), 3.13 (d, J = 7.8 Hz, 2H), 1.40 (s, 9H); 13C NMR (100 MHz, CDCl3) delta 169.4, 167.5, 137.0, 131.5, 130.6, 120.5, 83.2, 54.3, 52.4, 34.0, 27.8; HR-FAB MS calcd for C15H20BrO4 [M+H]+ 343.0545, found 343.0558.

Reference： [1]Tetrahedron Asymmetry,2015,vol. 26,p. 214 - 218
[2]Organic Letters,2016,vol. 18,p. 5484 - 5487

8
[ 42726-73-8 ]
[ 589-15-1 ]
1-tert-butyl 3-methyl 2-benzoyloxy-2-(4-bromobenzyl)malonate [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 5484 - 5487

9
[ 7343-34-2 ]
[ 589-15-1 ]
1-(4-bromobenzyl)-3,5-dimethyl-1H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%		In a 50 mL round-bottomed flask under N2 at 0 °C, sodium hydride (60percent in mineral oil, 0.184 g, 4.60 mmol) was added to a solution of 3,5-dimethyl-lH-l,2,4-triazole (0.311 g, 3.20 mmol) in DMF (12 mL) and the mixture was stirred for 20 min. 4-Bromobenzyl bromide (0.960 g, 3.84 mmol) was then added to the mixture and stirring was continued at RT for 2.5 h. The reaction mixture was then poured into H20 and the product was extracted with EtOAc (x3). The combined organic extract was washed with 0 (x3) and brine, dried over anhydrous sodium sulfate and concentrated to dryness. The residue was purified on ISCO using a 40 g column (0-20percent MeOH-DCM) to afford the title compound (0.382 g, 1.44 mmol, 45percent yield) as an off-white solid. LC (Method B): 1.538 min. MS (APCI): calcd for C11H13BrN3 [M + H]+ m/z 266.0, found 266.1. 1H NMR (400 MHz, CDCI3) delta ppm 7.43 - 7.52 (m, 2H), 7.00 - 7.08 (m, J = 8.22 Hz, 2H), 5.16 (s, 2H), 2.37 (s, 3H), 2.35 (s, 3H).

Reference： [1]Patent: WO2018/5591,2018,A1 .Location in patent: Page/Page column 528

10
[ 150058-27-8 ]
[ 589-15-1 ]
[ 892505-90-7 ]

Yield	Reaction Conditions	Operation in experiment
85%		To a 50 mL pressure vessel containing methyl 2-ethoxy-lH-benzo[d]imidazole-7- carboxylate (1.00 g, 4.54 mmol) was added 2-propanol (15 mL) and potassium carbonate (1.25 g, 9.08 mmol) and the mixture was stirred at 30°C for 5 min. To this mixture was added l-bromo-4-(bromomethyl)benzene (1.19 g, 4.77 mmol) and tetrabutylammonium iodide (0.084 g, 0.23 mmol) and the temperature of the reaction was raised to 45 °C. After 60 min an additional 15 mL of 2-propanol was added and the reaction was stirred at the same temperature for another 90 min. The cooled reaction mixture was diluted with EtOAc (200 mL) and 0 (50 mL), the layers were separated and the organic phase was washed (brine), dried (anhydrous sodium sulfate), filtered and evaporated. The residue was dry-packed onto silica gel (15 g) and purified on a 40 gram column (ISCO/ 0-60percent EtOAc-hexane) to provide the title compound as a pale yellow solid (1.50 g, 3.86 mmol, 85percent yield). LC-MS (Method H): 1.38 min, [M + H]+= 389.0; H NMR (400 MHz, CDC13) delta ppm 7.73 (dd, J= 7.8, 1.2 Hz, 1H), 7.58 (dd, /= 7.8, 1.2 Hz, 1H), 7.33 - 7.39 (: 2H), 7.18 (t, /= 8.0 Hz, 1H), 6.87 (m, /= 8.6 Hz, 2H), 5.58 (s, 2H), 4.65 (q, /= 7.2 Hz, 2H), 3.76 (s, 3H), 1.47 (t, /= 7.0 Hz, 3H).
72%		To an eggplant flask, <strong>[150058-27-8]2-ethoxy-1H-benzimidazole-7-carboxylic acid methyl ester</strong> (10 g, 45.4 mmol: "imidazole derivative (compound of formula (4a)"), potassium carbonate (12.5 g, 90.8 mmol: "Base"), and isopropyl alcohol (100 mL: first reaction solvent / branched alcohol), and the mixture was stirred at room temperature for 5 minutes. To this reaction solution, 4-bromobenzyl bromide (12 g, 47.9 mmol: "dihalogen compound") and tetra-n-butylammonium iodide (0.839 g, 2.27 mmol: "iodine catalyst") were added. Followed by stirring at 45 ° C. for 15 hours. The reaction solution was concentrated under reduced pressure, ethyl acetate (100 mL) was added to the concentrated residue, washed three times with water (100 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give 1- (4-bromobenzyl) -1H-benzimidazole-7-carboxylic acid methyl ester ("halogenated benzimidazole derivative") as a solid in a yield of 17.1 g (44.0 mmol, yield 98percent). This product was recrystallized from ethyl acetate to obtain 12.8 g (yield 72percent) of the objective product ("halogenated benzimidazole derivative") as a pure product.

Reference： [1]Patent: WO2018/5591,2018,A1 .Location in patent: Page/Page column 429
[2]Patent: JP2018/154611,2018,A .Location in patent: Paragraph 0165; 0166; 0167

11
[ 150058-27-8 ]
[ 589-15-1 ]
[ 1215298-35-3 ]

Reference： [1]Patent: JP2018/154611,2018,A

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Preparation of Alkylbenzene ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Vilsmeier-Haack Reaction

Historical Records

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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. 589-15-1 ] {[proInfo.proName]}

Quality Control of [ 589-15-1 ]

Related Doc. of [ 589-15-1 ]

Product Citations Expand+

Product Details of [ 589-15-1 ]

Calculated chemistry of [ 589-15-1 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 589-15-1 ]

Application In Synthesis of [ 589-15-1 ]

[ 589-15-1 ] Synthesis Path-Upstream 1~3

[ 589-15-1 ] Synthesis Path-Downstream 1~11

Technical Information

Related Functional Groups of [ 589-15-1 ]

Aryls

Bromides

Benzyl bromides

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 589-15-1 ]