[ CAS No. 15854-87-2 ] {[proInfo.proName]}

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2D 3D

Structure of 15854-87-2 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 15854-87-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 15854-87-2 ]

SDS Specification

Alternatived Products of [ 15854-87-2 ]

Product Citations

Chromophore Optimization in Organometallic Au(III) Cys Arylation of Peptides and Proteins for 266 nm Photoactivation

Jacob Silzel ; Chengwei Chen ; Colomba Sanchez-Marsetti , et al. ChemRxiv,2024. DOI: 10.26434/chemrxiv-2024-bthcz

Abstract: Cysteine is the most reactive naturally occurring amino acid due to the presence of a free thiol, presenting a tantalizing handle for covalent modification of peptides/proteins. Although many mass spectrometry experiments could benefit from site-specific modification of Cys, the utility of direct arylation has not been thoroughly explored. Recently, Spokoyny and coworkers reported a Au(III) organometallic reagent that robustly arylates Cys and tolerates a wide variety of solvents and conditions. Given the chromophoric nature of aryl groups and the known susceptibility of carbon-sulfur bonds to photodissociation, we set out to identify an aryl group that could efficiently cleave Cys carbon-sulfur bonds at 266 nm. A streamlined workflow was developed to facilitate rapid examination of a large number of aryls with minimal sample using a simple test peptide, RAAACGVLK. We were able to identify several aryl groups that yield abundant homolytic photodissociation of the adjacent Cys carbon-sulfur bonds with short activation times (<10 ms). In addition, we characterized the radical products created by photodissociation by subjecting the product ions to further collisional activation. Finally, we tested Cys arylation with human hemoglobin, identified reaction conditions that facilitate efficient modification of intact proteins, and evaluated the photochemistry and activation of these large radical ions.

Keywords: Fragmentation ; photodissociation ; radical-directed dissociation ; cysteine modification

Purchased from AmBeed: 15854-87-2 ; 615-43-0 ; 5029-67-4 ; 1120-90-7 ; 540-37-4

Product Details of [ 15854-87-2 ]

CAS No. :	15854-87-2	MDL No. :	MFCD02093937
Formula :	C₅H₄IN	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	RTLUPHDWSUGAOS-UHFFFAOYSA-N
M.W :	205.00	Pubchem ID :	609492
Synonyms :

Calculated chemistry of [ 15854-87-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	36.95
TPSA :	12.89 ?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) :	-6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.56
Log Po/w (XLOGP3) :	1.51
Log Po/w (WLOGP) :	1.69
Log Po/w (MLOGP) :	1.41
Log Po/w (SILICOS-IT) :	2.47
Consensus Log Po/w :	1.73

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.7
Solubility :	0.412 mg/ml ; 0.00201 mol/l
Class :	Soluble
Log S (Ali) :	-1.39
Solubility :	8.37 mg/ml ; 0.0408 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.98
Solubility :	0.215 mg/ml ; 0.00105 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.58

Safety of [ 15854-87-2 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 15854-87-2 ]

* 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.

Upstream synthesis route of [ 15854-87-2 ]
Downstream synthetic route of [ 15854-87-2 ]

[ 15854-87-2 ] Synthesis Path-Upstream 1~5

1
[ 15854-87-2 ]
[ 108-95-2 ]
[ 4783-86-2 ]

Reference： [1] Catalysis Science and Technology, 2016, vol. 6, # 6, p. 1701 - 1709
[2] Synlett, 2012, # 1, p. 101 - 106
[3] Tetrahedron Letters, 2006, vol. 47, # 29, p. 5045 - 5048

2
[ 15854-87-2 ]
[ 139-02-6 ]
[ 4783-86-2 ]

Reference： [1] Tetrahedron, 2002, vol. 58, # 24, p. 4931 - 4935

3
[ 15854-87-2 ]
[ 110210-11-2 ]
[ 2767-90-0 ]

Reference： [1] Angewandte Chemie - International Edition, 2019, vol. 58, # 15, p. 5003 - 5007[2] Angew. Chem., 2019, vol. 131, # 15, p. 5057 - 5061,5

4
[ 15854-87-2 ]
[ 100-51-6 ]
[ 49826-70-2 ]

Reference： [1] Tetrahedron, 2002, vol. 58, # 24, p. 4931 - 4935

5
[ 15854-87-2 ]
[ 111-86-4 ]
[ 64690-19-3 ]

Reference： [1] Journal of the American Chemical Society, 2008, vol. 130, # 20, p. 6586 - 6596

[ 15854-87-2 ] Synthesis Path-Downstream 1~6

1
[ 53137-27-2 ]
[ 15854-87-2 ]
2,4-dimethyl-5-pyridinylthiazole [ No CAS ]

Reference： [1]Organic Letters,2010,vol. 12,p. 4745 - 4747

2
[ 271-34-1 ]
[ 15854-87-2 ]
[ 1542750-10-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium phosphate; In dimethyl sulfoxide; at 80℃; for 5h;Inert atmosphere;	General procedure: An oven dried two-necked round bottom flask was charged with aryl halide (1mmol) and K3PO4 (2mmol), evacuated, and backfilled with argon. The azole compound (1mmol) and 2mL of DMSO were added under argon. After that Cu-NP (1.6mmol) was added and the flask was again backfilled with argon. The flask was then immersed in a preheated oil bath at 80C until the conversion was completed (detected by TLC). The cooled mixture was partitioned between ethyl acetate (10mL) and saturated NH4Cl (10mL). The aqueous layer was extracted with ethyl acetate (2×10mL), the organic layer was washed with brine (20mL), dried over anhydrous Na2SO4, and concentrated in vacuum. The residue was purified by column chromatography on silica gel using ethyl acetate in hexane (1.5-10%) as eluent to afford the desired product. All the products have been characterized by 1H NMR, 13C NMR, and mass spectroscopy. For new products, FTIR data were also recorded.Analytical data of compound 3a: 1H NMR (CDCl3, 500MHz): δ 7.94 (d, J=8.5Hz, 2H), 7.87 (d, J=8.5Hz, 2H), 7.78 (d, J=8.5Hz, 1H), 7.70-7.68 (m, 2H), 7.27-7.24 (m, 1H), 7.20-7.17 (m, 1H), 6.79 (d, J=3.5Hz, 1H); 13C NMR (CDCl3, 125MHz): δ 142.8, 135.5, 129.7, 128.3, 127.4, 126.9 (q, J=59Hz), 125.4 (q, J=362Hz), 123.9, 122.9, 121.4, 121.0, 110.3, 104.9; MS(EI) 262.4 (M+). Anal. Calcd for C15H10F3N: C, 68.96, H, 3.86, N, 5.36. Found: C, 68.89, H, 3.88, N, 5.33.
90%	With potassium phosphate; copper; In dimethyl sulfoxide; at 80℃; for 5h;Inert atmosphere;	General procedure: An oven dried two-necked round bottom flask was charged with aryl halide (1mmol) and K3PO4 (2mmol), evacuated, and backfilled with argon. The azole compound (1mmol) and 2mL of DMSO were added under argon. After that Cu-NP (1.6mmol) was added and the flask was again backfilled with argon. The flask was then immersed in a preheated oil bath at 80C until the conversion was completed (detected by TLC). The cooled mixture was partitioned between ethyl acetate (10mL) and saturated NH4Cl (10mL). The aqueous layer was extracted with ethyl acetate (2×10mL), the organic layer was washed with brine (20mL), dried over anhydrous Na2SO4, and concentrated in vacuum. The residue was purified by column chromatography on silica gel using ethyl acetate in hexane (1.5-10%) as eluent to afford the desired product. All the products have been characterized by 1H NMR, 13C NMR, and mass spectroscopy. For new products, FTIR data were also recorded.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 941 - 944
[2]Tetrahedron Letters,2014,vol. 55,p. 941 - 944

3
[ 15854-87-2 ]
[ 45887-08-9 ]
3-(1-(pyridin-4-yl)-1H-pyrazol-3-yl)pyridine [ No CAS ]

Reference： [1]Crystal Growth and Design,2016,vol. 16,p. 1617 - 1625

4
[ 15854-87-2 ]
[ 589-87-7 ]
[ 39795-60-3 ]

Yield	Reaction Conditions	Operation in experiment
102 g		4-iodoyridine 149g and THF 689mL flown into a flask, the temperature of the contents kept 1 °C, 2.0M isopropylmagnesium chloride THF soln. 400 ml is dropwise added. after dropwise addition 15 minutes stirred, tetramethylethylenediaminezinc(II) chloride complex 202g is added, with stirring, 25 minutes at room temperature. Next, p-bromoiodobenzene 226g and tetrakis(triphenylphosphine)palladium(0) 0.34g was added and heated to reflux for 3 hours. The reaction liquid cooling to room temperature, sodium salt aqueous acetic acid ethylenediaminediacetic 4 · 4 (730g/1.7L) is added, the organic layer. After intercalating organic layer is dried by a drying agent, distilling the crude product is obtained and the solvent is reduced. This crude product is silica gel column chromatography (developing solvent: toluene-toluene/ethyl acetate = 9/1 (volume ratio)) is purified by, 4-(4-bromophenyl)pyridine 102g is obtained.

Reference： [1]Patent: JP5907069,2016,B2 .Location in patent: Paragraph 0184

5
[ 15854-87-2 ]
[ 7037-49-2 ]

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 2856 - 2858

6
[ 15854-87-2 ]
[ 189178-09-4 ]
[ 359647-66-8 ]

Yield	Reaction Conditions	Operation in experiment
85%		General procedure: The appropriate mono-, di- or tri-acetylene TPA derivative(200 mg) and 4-iodopyridine were dissolved in a mixture ofdioxane/piperidine (25 mL, 4/1). Ar was bubbled through themixture for 10 min and [Pd(PPh3)4] and CuI were added. The reactionmixture was stirred at 90 C for 12 h. The cooled reactionmixture was diluted with H2O (50 mL) and extracted with CH2Cl2(2 50 mL). The combined organic extracts were thenwashed withsaturated NH4Cl solution, brine, and dried. Finally, the solventswere evaporated under vacuum and the crude productwas purifiedby column chromatography (SiO2, appropriate eluent).

Reference： [1]Dyes and Pigments,2017,vol. 146,p. 467 - 478

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Isomers

Technical Information

? Alkyl Halide Occurrence ? General Reactivity ? Hiyama Cross-Coupling Reaction ? Kinetics of Alkyl Halides ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

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[ 15854-87-2 ]

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P222	Do not allow contact with air.
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P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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P262	Do not get in eyes, on skin, or on clothing.
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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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P235 + P410	Keep cool. Protect from sunlight.
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Code	Phrase
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P310	Immediately call a POISON CENTER or doctor/physician.
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P321
P322
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
P380	Evacuate area.
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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.
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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.
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[ CAS No. 15854-87-2 ] {[proInfo.proName]}

Quality Control of [ 15854-87-2 ]

Related Doc. of [ 15854-87-2 ]

Product Citations

Product Details of [ 15854-87-2 ]

Calculated chemistry of [ 15854-87-2 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 15854-87-2 ]

Application In Synthesis of [ 15854-87-2 ]

[ 15854-87-2 ] Synthesis Path-Upstream 1~5

[ 15854-87-2 ] Synthesis Path-Downstream 1~6

Technical Information

Related Parent Nucleus of [ 15854-87-2 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 15854-87-2 ]