33421-36-2|2-(Pyridin-2-yl)phenol| Ambeed

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Quality Control of [ 33421-36-2 ] Purity: 97% SDS Specification

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Product Citations

Red-Emitting Cyclometalated Platinum (II) Complexes with Pyrrolide and Phenoxide-Based Ancillary Ligands

Phan, Son NT ; Teets, Thomas S ;

DOI: 10.1021/acs.inorgchem.5c01504 PubMed ID: 40489667 Inorg. Chem.,2025.

Abstract: Phosphorescent platinum(II) complexes often have low photoluminescence quantum yields (Φ_PL) due to the less effective spin−orbit coupling (SOC) in square-planar geometries, leading to relatively small radiative rate constants (k_r). In this work, seven new red-emitting heteroleptic cyclometalated Pt(II) complexes are described, with the goal of investigating ancillary ligands that promote fast k_r values. The heteroleptic fourcoordinate complexes include 1-phenylisoquinoline as the cyclometalating ligand, paired with an anionic chelating ancillary ligand with either N^N, O^O, or mixed N^O coordination. More specifically, the ancillary ligands all contain anionic pyrrolide or phenoxide rings, paired with imine, carbonyl, pyridyl, or imidazolyl neutral donors. The seven compounds are structurally characterized by multinuclear NMR and six of the seven by single-crystal X-ray diffraction. A comprehensive study of photophysical properties shows that the compounds all exhibit red phosphorescence, some with a clear vibronic structure indicative of the substantial ³ (π → π*) character in the emissive excited state, involving the cyclometalating ligand, while others exhibit a photoluminescence profile suggestive of pronounced charge-transfer character in the triplet state. When measured in poly(methyl methacrylate) films, the highest k_r achieved is 1.2 × 10⁵ s ⁻¹, with photoluminescence quantum yields ranging from 0.14 to 0.38.

Purchased from AmBeed: 13228-40-5 ; 117-99-7 ; 33421-36-2 ; 7697-46-3

Product Details of [ 33421-36-2 ]

CAS No. :	33421-36-2
Formula :	C₁₁H₉NO
M.W :	171.20
SMILES Code :	OC1=CC=CC=C1C2=NC=CC=C2
MDL No. :	MFCD18072507
InChI Key :	HPDNGBIRSIWOST-UHFFFAOYSA-N
Pubchem ID :	135489221

Safety of [ 33421-36-2 ]

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

Computational Chemistry of [ 33421-36-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	12
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	51.7
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	33.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.03
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	2.16
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.45
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.	1.47
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	2.54
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.13

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.88
Solubility	0.226 mg/ml ; 0.00132 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.49
Solubility	0.556 mg/ml ; 0.00325 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-3.96
Solubility	0.0187 mg/ml ; 0.000109 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	Yes
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	Yes
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.	-5.81 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)	1.67

Application In Synthesis of [ 33421-36-2 ]

* 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 [ 33421-36-2 ]

[ 33421-36-2 ] Synthesis Path-Downstream 1~35

1
[ 33421-36-2 ]
2-[2-(2-dimethylamino-ethoxy)-phenyl]-pyridine [ No CAS ]

References: [1]Patent: US2566360,1948, .

2
[ 5029-67-4 ]
[ 108-95-2 ]
[ 51035-40-6 ]
[ 33421-36-2 ]
[ 98061-22-4 ]

References: [1]Chemical and pharmaceutical bulletin,1985,vol. 33,p. 1009 - 1015.

3
[ 33421-36-2 ]
[ 108-24-7 ]
[ 87573-07-7 ]

References: [1]Helvetica Chimica Acta,1983,vol. 66,p. 1039 - 1045.

4
[ 33421-36-2 ]
[ 33400-78-1 ]
[ 33400-82-7 ]
[ 127527-00-8 ]

References: [1]Chemistry of Heterocyclic Compounds,1990,vol. 26,p. 65 - 70.
Khimiya Geterotsiklicheskikh Soedinenii,1990,p. 75 - 80.

5
[ 33421-36-2 ]
[ 127527-00-8 ]

References: [1]Chemistry of Heterocyclic Compounds,1990,vol. 26,p. 65 - 70.
Khimiya Geterotsiklicheskikh Soedinenii,1990,p. 75 - 80.

6
[ 26482-54-2 ]
[ 100-67-4 ]
[ 504-29-0 ]
[ 51035-40-6 ]
[ 33421-36-2 ]

References: [1]Chemistry of Heterocyclic Compounds,1982,vol. 18,p. 212 - 212.
[2]Chemistry of Heterocyclic Compounds,1982,vol. 18,p. 212 - 212.

7
[ 5957-89-1 ]
[ 33421-36-2 ]

References: [1]Synthetic Communications,2001,vol. 31,p. 869 - 875.
[2]Journal of the Chemical Society, Dalton Transactions,1992,p. 3345 - 3352.
[3]Helvetica Chimica Acta,1983,vol. 66,p. 1039 - 1045.
[4]Journal of the Chemical Society. Perkin transactions II,1994,p. 1603 - 1610.
[5]Chemistry of Heterocyclic Compounds,1990,vol. 26,p. 65 - 70.
Khimiya Geterotsiklicheskikh Soedinenii,1990,p. 75 - 80.
[6]Journal of Materials Chemistry,1998,vol. 8,p. 1999 - 2003.
[7]Chemical and pharmaceutical bulletin,1985,vol. 33,p. 1009 - 1015.
[8]Chemistry Letters,2001,p. 1060 - 1061.
[9]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 471 - 475.

8
[ 93953-42-5 ]
[ 33421-36-2 ]

References: [1]Journal of the American Chemical Society,2014,vol. 136,p. 3981 - 3994.
[2]Tetrahedron Letters,1984,vol. 25,p. 4045 - 4048.

9
[ 109-04-6 ]
[ 16750-63-3 ]
[ 33421-36-2 ]

References: [1]Australian Journal of Chemistry,1997,vol. 50,p. 109 - 114.

11
2-<2-methoxy-phenyl>-1,2-dihydro-pyridine [ No CAS ]
[ 33421-36-2 ]

References: [1]Journal of Organic Chemistry,1946,vol. 11,p. 741,749.

12
[ 108-95-2 ]
sodium pyridine isodiazotate-⁽²⁾ [ No CAS ]
[ 33421-36-2 ]

References: [1]Zhurnal Russkago Fiziko-Khimicheskago Obshchestva,1920,vol. 50,p. 516,518.
Chemisches Zentralblatt,1923,vol. 94,p. 1022.

13
2-(2-isopropoxyphenyl)pyridine [ No CAS ]
[ 33421-36-2 ]

References: [1]Synthetic Communications,2001,vol. 31,p. 869 - 875.

14
[ 358741-44-3 ]
[ 33421-36-2 ]

References: [1]Synthetic Communications,2001,vol. 31,p. 869 - 875.

15
cis-2-ethynylcyclopropyl-2-pyridylketone [ No CAS ]
[ 33421-36-2 ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 526 - 527.

16
[ 33421-36-2 ]
haloacetonitrile [ No CAS ]
2-[2-(pyridin-2-yl)phenoxy]acetonitrile [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 471 - 475.

17
[ 33421-36-2 ]
[ 358-23-6 ]
[ 485385-79-3 ]

References: [1]European Journal of Organic Chemistry,2002,p. 2547 - 2556.

18
[ 33421-36-2 ]
[ 299917-90-1 ]
(3aR,8aR)-2-[2-(2,2-dimethyl-4,4,8,8-tetraphenyltetrahydro-1,3,5,7-tetraoxa-6-phosphaazulene-6-yloxy)-phenyl]-pyridine [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2002,vol. 344,p. 868 - 883.

19
[ 502159-04-8 ]
[ 33421-36-2 ]

References: [1]Advanced Synthesis and Catalysis,2002,vol. 344,p. 868 - 883.

20
[ 33421-36-2 ]
[ 1617-17-0 ]
2-(2-pyridin-2-ylphenoxy)propionitrile [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6160 - 6173.

21
[ 110-86-1 ]
[ 533-58-4 ]
[ 33421-36-2 ]
[ 54168-07-9 ]
[ 86610-20-0 ]

References: [1]Heterocycles,2004,vol. 64,p. 499 - 504.
[2]Tetrahedron,2006,vol. 62,p. 7824 - 7837.

22
[ 1008-89-5 ]
[ 33421-36-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With oxone; Ru(MesCO2)(4,4'-dibromobipyridine)(p-cymene); trifluoroacetic acid; trifluoroacetic anhydride; In 1,2-dichloro-ethane; at 140℃; for 8h;Sealed tube; Green chemistry;	General procedure: A mixture of 2-arylpyridines (1 eq), Ru(MesCO2)(L) (p-cymene) [L- 2,2?-bypyridine or 4,4?-dibromobipyridine] (5 mol%), TFA: TFAA=0.6 ml:0.4 ml and Oxone (4 eq) was taken in a 30 ml sealed tube. 1 ml of DCE was added and the tube was then placed in an oil bath, stirred, and heated at 140C. The progress of the reaction was checked after every 8 hrs. After complete consumption of starting material the reaction mixture was cooled to room temperature, quenched with brine and extracted with dichloromethane. The combined organic layer was dried with anhydrous Na2SO4, and vacuum evaporated. The crude product was purified over a column of silica gel (eluent: hexane/ethyl acetate) to afford the desired products.
67%	With water; oxygen;copper diacetate; In acetonitrile; at 130℃; for 36h;Product distribution / selectivity;	EXAMPLE 1; Synthesis of 2-(pyridine-2-yl)phenol (Ib)In a 20 mL tube, 2-phenylpyridine (0.3 mmol, 1 equiv), Cu(OAc)2 (54.6 mg, 0.3 mmol, 1 equiv) and H2O (5.4 muL, 0.3 mmol, 1 equiv) were dissolved in 1 mL of dry MeCN under * oxygen. The tube was sealed with a Teflon lined cap, and the reaction mixture was stirred at 1300C for 36 h. The reaction mixture was diluted with 20 mL of CH2Cl2 and then treated with 10 mL of saturated Na2S aqueous solution. The mixture was filtered through a pad of Celite, and the filtrate was washed twice with brine. The organic layer was dried over Na2SO4 and concentrated under vacuum. After purification by column chromatography on silica gel with a gradient eluent of hexane and ether (Rf = 0.35 in 2:1 hexane: ether), the title product was obtained as a colorless oil (34.4 mg, 67%). 1H NMR (400 MHz, CDCl3) delta 14.39 (s, IH), 8.52 (d, J== 4.8 Hz, IH), 7.93 (d, J= 8.4 Hz, IH), 7.87-7.84 (m, IH), 7.81 (d, J= 8.0 Hz, IH), 7.31 (td, J= 7.6, 1.2 Hz, IH), 7.27-7.24 (m, IH), 7.03 (d, J= 8.0 Hz, IH), 6.92 (td, J = 7.6, 1.2 Hz, IH); 13C NMR (100 MHz5 CDCl3) delta 160.29, 158.10, 146.08, 138.05, 131.77, 126.39, 121.79, 119.31, 119.05, 118.89; IR (thin film) v 2923, 1594, 1477, 1270 cm"1; HRMS (TOF) Calcd for CnH10NO (M+ H) 172.0762, found 172.0768.
30%	With 18O-labeled water;copper diacetate; In acetonitrile; at 130℃; for 36h;Mechanism;	EXAMPLE 6; Labeling ExperimentIn a 20 mL tube, substrate (0.3 mmol, 1 equiv), Cu(OAc)2 (54.6 mg, 0.3 mmol, 1 equiv) and H218O (5.4 muL, 0.3 mmol, 1 equiv) were dissolved in 1 mL of dry MeCN under N2. The <n="42"/>tube was sealed with a Teflon lined cap, and the reaction mixture was stirred at 130C for 24 h. The reaction mixture was diluted with 20 mL of CH2CI2 and then treated with 10 mL of saturated Na2S aqueous solution. The mixture was filtered through a pad of Celite, and the filtrate was washed twice with brine. The organic layer was dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography on silica gel (Rf = 0.35, in 2:1 hexane and ether) to give the product in 30% yield. By the analysis of GC-MS, no I8O-labeled hydroxylated product was detected and only hydroxylated product Ib was obtained.

22%	With water; oxygen;copper (II)-fluoride; In dimethyl sulfoxide; at 130℃; for 24h;Product distribution / selectivity;	Hydroxylation by CuF 2In a 20 mL tube, substrate (0.3 mmol, 1 equiv), CuF2 (30.5 mg, 0.3 mmol, 1 equiv) andH2O (27 muL, 1.5 mmol, 5 equiv) were dissolved in 1 mL of dry DMSO under atmospheric air. The tube was sealed with a Teflon lined cap, and the reaction mixture was stirred at1300C for 24 h. The reaction mixture was diluted with 20 mL of CH2Cl2 and then treated <n="39"/>with 10 mL of saturated Na2S aqueous solution. The mixture was filtered through a pad of Celite, and the filtrate was washed twice with brine. The organic layer was dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography on silica gel (Rf = 0.35 in 2:1 hexane: ether), Ib was obtained as a colorless oil (11.2 mg, 22%).
	With tert.-butylhydroperoxide; palladium dichloride; In water; chlorobenzene; at 140℃; for 24h;Green chemistry;	To a clean, dry carousel tube, PdCl2 (0.05mmol,8.87mg), 2-phenylpyridine (2mmol,0.286ml), tbutylhydroperoxide (70%solutioninwater, 6mmol, 1.04ml) and chlorobenzene (5mL) were added. The reaction was heated to 140 oC with stirring for 24 h before being cooled to rt. The reaction mixture was filtered through celite and the solvent removed. The crude mixture was then purified by flash column chromatography eluting with dichloromethane to give the phenolic intermediate.

References: [1]ACS Catalysis,2016,vol. 6,p. 6050 - 6054.
[2]Journal of Organic Chemistry,2015,vol. 80,p. 2925 - 2929.
[3]Organic Letters,2017,vol. 19,p. 3532 - 3535.
[4]ChemPhysChem,2019,vol. 20,p. 665 - 671.
[5]Tetrahedron Letters,2017,vol. 58,p. 3743 - 3746.
[6]Angewandte Chemie - International Edition,2013,vol. 52,p. 5827 - 5831.
Angew. Chem.,2013,vol. 125,p. 5939 - 5943,5.
[7]Advanced synthesis and catalysis,2020.
[8]Journal of the American Chemical Society,2006,vol. 128,p. 6790 - 6791.
[9]Patent: WO2007/123910,2007,A2 .Location in patent: Page/Page column 27; 37.
[10]Organic Letters,2018,vol. 20,p. 5533 - 5536.
[11]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2017 - 2021.
[12]Organic Letters,2018,vol. 20,p. 6799 - 6803.
[13]Organic Letters,2011,vol. 13,p. 6536 - 6539.
[14]Journal of Organic Chemistry,2019,vol. 84,p. 10088 - 10101.
[15]Patent: WO2007/123910,2007,A2 .Location in patent: Page/Page column 27; 40-41.
[16]Patent: WO2007/123910,2007,A2 .Location in patent: Page/Page column 29-30; 37-38.
[17]Synlett,2013,vol. 24,p. 2687 - 2690.
[18]Organometallics,2014,vol. 33,p. 4442 - 4448.
[19]Chemical Communications,2018,vol. 54,p. 8202 - 8205.
[20]Tetrahedron,2019,vol. 75,p. 2547 - 2552.

23
[ 87573-07-7 ]
[ 33421-36-2 ]

References: [1]Chemistry Letters,2006,vol. 35,p. 842 - 843.

24
[ 33421-36-2 ]
2-{2-[1-(4,5-dihydro-1<i>H</i>-imidazol-2-yl)-ethoxy]-phenyl}-pyridine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6160 - 6173.

25
[ 4203-50-3 ]
[ 33421-36-2 ]

References: [1]Advanced Synthesis and Catalysis,2002,vol. 344,p. 868 - 883.

26
[ 502159-01-5 ]
[ 33421-36-2 ]

References: [1]Advanced Synthesis and Catalysis,2002,vol. 344,p. 868 - 883.

27
[ 108-95-2 ]
cyclic dichloride of/the/ benzoic acid sulfinic acid-⁽²⁾ [ No CAS ]
[ 33421-36-2 ]

References: [1]Advanced Synthesis and Catalysis,2002,vol. 344,p. 868 - 883.

28
[ 33421-36-2 ]
[ 485385-78-2 ]

References: [1]European Journal of Organic Chemistry,2002,p. 2547 - 2556.

29
[ 33421-36-2 ]
6,6'-methanediylbis(pyridio[2,1-a]isoindole) [ No CAS ]

References: [1]European Journal of Organic Chemistry,2002,p. 2547 - 2556.

30
[ 33421-36-2 ]
2-[2-(4,5-dihydro-1<i>H</i>-imidazol-2-ylmethoxy)-phenyl]-pyridine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 471 - 475.

31
[ 5720-06-9 ]
[ 33421-36-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 471 - 475.

32
[ 109-04-6 ]
[ 33421-36-2 ]

References: [1]Chemistry Letters,2001,p. 1060 - 1061.
[2]Synthetic Communications,2001,vol. 31,p. 869 - 875.
[3]Journal of the Chemical Society. Perkin transactions II,1994,p. 1603 - 1610.
[4]Organic Letters,2018,vol. 20,p. 5533 - 5536.

33
[ 578-57-4 ]
BBr₃ [ No CAS ]
[ 33421-36-2 ]

References: [1]Chemistry Letters,2001,p. 1060 - 1061.
[2]Synthetic Communications,2001,vol. 31,p. 869 - 875.

34
[ 109-04-6 ]
<1,3>dioxolan-2-ylidene-malonodinitrile [ No CAS ]
[ 33421-36-2 ]

References: [1]Journal of Materials Chemistry,1998,vol. 8,p. 1999 - 2003.

35
[ 16750-63-3 ]
[ 33421-36-2 ]

References: [1]Journal of Materials Chemistry,1998,vol. 8,p. 1999 - 2003.
[2]Journal of the Chemical Society. Perkin transactions II,1994,p. 1603 - 1610.
[3]Journal of the Chemical Society, Dalton Transactions,1992,p. 3345 - 3352.

Historical Records

Technical Information

• Appel Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Hydride Reductions • Jones Oxidation • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Preparation of Alcohols • Preparation of Amines • Reactions of Alcohols • Reactions of Benzene and Substituted Benzenes • Reactions with Organometallic Reagents • Ritter Reaction • Sharpless Olefin Synthesis • Swern Oxidation

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[ 33421-36-2 ]

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[ 33421-36-2 ]

Pyridines

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
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.
P235	Keep cool
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.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
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.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
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.
P370	In case of fire:
P371	In case of major fire and large quantities:
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
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
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
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.: 33421-36-2

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