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4556-23-4 Usage

Chemical Properties

4-Mercaptopyridine is Yellow to light yellow crystalline powder

Uses

Different sources of media describe the Uses of 4556-23-4 differently. You can refer to the following data:
1. 4-Mercaptopyridine is a pyridine derivative used as a redox reagents for the in vitro refolding of a recombinantly expressed single-chain Fv fragment (scFvOx). Used in studies along with thiosulfate to measure alliinase activity.
2. mercaptopyridine is also known as sodium pyrithione. It is a preservative that is not commoly used.
3. 4-Mercaptopyridine was used as a probe molecule to study the performance of the gold nanorod (AuNR)/polycaprolactone (PCL) fibrous mesh.

Purification Methods

Purify the thiol by dissolving ~45g in boiling H2O (100mL) (charcoal), filter and precipitate it by adding 50% aqueous NaOH (~80mL) to pH ~6. Dissolve the precipitate in EtOH, evaporate it to dryness, then crystallise it from boiling EtOH (~100mL, charcoal) to give yellow flat hexagonal plates (m 186o). It sublimes readily in vacuo. [King & Ware J Chem Soc 873 1939.] The picrate forms yellow needles from H2O with m 222o(dec). The 4-methylmercaptopyridine derivative crystallises from pet ether (m 47o , also 44-45o was reported, with a pK2 0 of 5.97) and was prepared by treatment with MeI/NaOH. Its picrate has m 2 4 5o (from H2O, MeOH or EtOH). The N-methyl-4-pyridinethiol derivative has m 168.5-170o (from EtOH), a pK2 0 of 1.30 and is soluble in CHCl3. [Albert & Barlin J Chem Soc 2384 1959, Beilstein 21 II 35, 22 III/IV 373, 22/7 V 147.]

Check Digit Verification of cas no

The CAS Registry Mumber 4556-23-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,5,5 and 6 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 4556-23:
(6*4)+(5*5)+(4*5)+(3*6)+(2*2)+(1*3)=94
94 % 10 = 4
So 4556-23-4 is a valid CAS Registry Number.
InChI:InChI=1/C5H5NS/c7-5-1-3-6-4-2-5/h1-4H,(H,6,7)/p-1

4556-23-4 Well-known Company Product Price

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  • Aldrich

  • (148202)  4-Mercaptopyridine  95%

  • 4556-23-4

  • 148202-1G

  • 423.54CNY

  • Detail
  • Aldrich

  • (148202)  4-Mercaptopyridine  95%

  • 4556-23-4

  • 148202-10G

  • 2,068.56CNY

  • Detail

4556-23-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Mercaptopyridine

1.2 Other means of identification

Product number -
Other names 4-Pyridinethiol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4556-23-4 SDS

4556-23-4Synthetic route

4-Chloropyridine
626-61-9

4-Chloropyridine

thiourea
17356-08-0

thiourea

A

pyridine-4-thiol
4556-23-4

pyridine-4-thiol

B

4,4'-thiobispyridine
37968-97-1

4,4'-thiobispyridine

Conditions
ConditionsYield
With 4-(2-pyridyl)pyridine; potassium tert-butylate In ammonia at -40℃; electrolysis;A 75%
B 5%
With 4-(2-pyridyl)pyridine; potassium tert-butylate In ammonia at -40℃; Rate constant; electrochemical reaction;A 75%
B 5%
pyridine
110-86-1

pyridine

N-(4-pyridyl)pyridinium hydrochloride
22752-98-3

N-(4-pyridyl)pyridinium hydrochloride

pyridine-4-thiol
4556-23-4

pyridine-4-thiol

Conditions
ConditionsYield
With hydrogen sulfide at 140℃;
4-pyridone
108-96-3

4-pyridone

pyridine-4-thiol
4556-23-4

pyridine-4-thiol

Conditions
ConditionsYield
With phosphorous (V) sulfide at 60 - 70℃;
With phosphorous (V) sulfide; xylene
4-Chloropyridine
626-61-9

4-Chloropyridine

pyridine-4-thiol
4556-23-4

pyridine-4-thiol

Conditions
ConditionsYield
With ethanol; water; potassium hydrosulfide at 140℃;
With sodium thioethylate In N,N-dimethyl-formamide for 16h; Heating;
With sodium hydrogen sulfide
4-pyridinethione
19829-29-9

4-pyridinethione

pyridine-4-thiol
4556-23-4

pyridine-4-thiol

Conditions
ConditionsYield
In cyclohexane Thermodynamic data; Free energy difference between protomers; other solvents;
4-chlorpyridine hydrochloride
7379-35-3

4-chlorpyridine hydrochloride

pyridine-4-thiol
4556-23-4

pyridine-4-thiol

Conditions
ConditionsYield
With sodium tetrahydroborate; sulfur 1.) 210 deg C, NaOH-KOH melt, 2 min.; 2.) water; Yield given. Multistep reaction;
1-(4-pyridyl)pyridinium chloride hydrochloride
5421-92-1

1-(4-pyridyl)pyridinium chloride hydrochloride

A

pyridine-4-thiol
4556-23-4

pyridine-4-thiol

B

4,4'-thiobispyridine
37968-97-1

4,4'-thiobispyridine

Conditions
ConditionsYield
With pyridine; thiourea at 150 - 180℃;
bis(4-pyridyl) disulfide
2645-22-9

bis(4-pyridyl) disulfide

Thiophosphoric acid S-octyl ester O-((1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxy-cyclohexyl) ester

Thiophosphoric acid S-octyl ester O-((1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxy-cyclohexyl) ester

A

pyridine-4-thiol
4556-23-4

pyridine-4-thiol

B

myo-inositol-1,2-cyclic phosphate
41158-67-2

myo-inositol-1,2-cyclic phosphate

Conditions
ConditionsYield
With phosphatidylinositol-specific phospholipase C from Bacillus cereus Product distribution; other reagents, relative velocities;
pyridine
110-86-1

pyridine

hydrogen sulfide
7783-06-4

hydrogen sulfide

1-(4-pyridyl)pyridinium chloride hydrochloride
5421-92-1

1-(4-pyridyl)pyridinium chloride hydrochloride

pyridine-4-thiol
4556-23-4

pyridine-4-thiol

bis(4-pyridyl) disulfide
2645-22-9

bis(4-pyridyl) disulfide

pyridine-4-thiol
4556-23-4

pyridine-4-thiol

Conditions
ConditionsYield
With bovine serum albumin pH=4.5 - 10.5; Kinetics;
With trimethylphosphane In ethanol at 20℃; for 4h;
pyridin-4-ol
626-64-2

pyridin-4-ol

pyridine-4-thiol
4556-23-4

pyridine-4-thiol

Conditions
ConditionsYield
With Lawessons reagent In tetrahydrofuran at 80℃;
pyridine-4-thiol
4556-23-4

pyridine-4-thiol

C152H232Cl8O16
1350521-16-2

C152H232Cl8O16

C192H264N8O16S8
1350521-13-9

C192H264N8O16S8

Conditions
ConditionsYield
With triethylamine In dimethyl sulfoxide at 60℃; for 48h; Inert atmosphere;100%
pyridine-4-thiol
4556-23-4

pyridine-4-thiol

C10H8N2S2*ClH

C10H8N2S2*ClH

Conditions
ConditionsYield
With hydrogenchloride; Cumene hydroperoxide; tert-butyl (S)-(tetrahydrotellurophen-3-yl)carbamate In dichloromethane; water at 25℃; Flow reactor;100%
pyridine-4-thiol
4556-23-4

pyridine-4-thiol

bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]
12354-84-6, 12354-85-7

bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]

((C5(CH3)5)Ir(SC5H4N)3H)*2HCl

((C5(CH3)5)Ir(SC5H4N)3H)*2HCl

Conditions
ConditionsYield
In dichloromethane (Ar) pyridine-4-thiol was added to soln. Ir complex in CH2Cl2 at room temp., stirred for 6 h at room temp.; solvent was removed in vacuo, residue was washed with CH2Cl2 and Et2O; elem. anal.;98%
pyridine-4-thiol
4556-23-4

pyridine-4-thiol

2-methylpropan-2-thiol
75-66-1

2-methylpropan-2-thiol

4-(tert-butyldisulfanyl)pyridine

4-(tert-butyldisulfanyl)pyridine

Conditions
ConditionsYield
With manganese(II)carbonate; 3,4,5-trihydroxybenzoic acid; oxygen; sodium carbonate In water at 80℃; under 2250.23 Torr; for 4h; pH=9; Schlenk technique; Green chemistry;98%
With tetra-O-acetyl riboflavin In methanol; water at 25℃; under 760.051 Torr; for 24h; Irradiation; Green chemistry; chemoselective reaction;76%
pyridine-4-thiol
4556-23-4

pyridine-4-thiol

2-bromonaphthalene
580-13-2

2-bromonaphthalene

4-(naphthalen-2-ylthio)pyridine

4-(naphthalen-2-ylthio)pyridine

Conditions
ConditionsYield
With C30H32Cl3N4Ni2(1+)*Cl(1-); potassium hydroxide In 1,4-dioxane at 40℃; for 6h; Reagent/catalyst;98%
pyridine-4-thiol
4556-23-4

pyridine-4-thiol

tetramethyl ammoniumhydroxide
75-59-2

tetramethyl ammoniumhydroxide

Pyridine-4-thiolatetetramethyl-ammonium;
138555-14-3

Pyridine-4-thiolatetetramethyl-ammonium;

Conditions
ConditionsYield
In benzene at 6 - 10℃; for 1h;97%
pyridine-4-thiol
4556-23-4

pyridine-4-thiol

1-(4-pyridyl)pyridinium chloride hydrochloride
5421-92-1

1-(4-pyridyl)pyridinium chloride hydrochloride

4,4'-thiobispyridine
37968-97-1

4,4'-thiobispyridine

Conditions
ConditionsYield
at 150℃; for 0.166667h;97%
at 140 - 150℃; for 2h;85%
pyridine-4-thiol
4556-23-4

pyridine-4-thiol

(3S,4R)-3-<(Bromoacetyl)amino>-4-methyl-2-oxetanone
157457-99-3

(3S,4R)-3-<(Bromoacetyl)amino>-4-methyl-2-oxetanone

(3S,4R)-3-<<(4-Pyridylthio)acetyl>amino>-4-methyl-2-oxetanone

(3S,4R)-3-<<(4-Pyridylthio)acetyl>amino>-4-methyl-2-oxetanone

Conditions
ConditionsYield
With sodium hydride 1.) DMF, 20 deg C, 10 min, 2.) CH2Cl2, 10 min;97%
pyridine-4-thiol
4556-23-4

pyridine-4-thiol

7β-[2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-methoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester

7β-[2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-methoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester

7β-[2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-methoxyiminoacetamido]-3-(4-pyridyl)thiomethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester

7β-[2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-methoxyiminoacetamido]-3-(4-pyridyl)thiomethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester

Conditions
ConditionsYield
With sodium methylate In methanol; N,N-dimethyl-formamide97%
pyridine-4-thiol
4556-23-4

pyridine-4-thiol

bromobenzene
108-86-1

bromobenzene

4-(phenylthio)pyridine
33399-48-3

4-(phenylthio)pyridine

Conditions
ConditionsYield
With C30H32Cl3N4Ni2(1+)*Cl(1-); potassium hydroxide In 1,4-dioxane at 40℃; for 6h; Reagent/catalyst;97%
pyridine-4-thiol
4556-23-4

pyridine-4-thiol

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

1-(bis(cyclohexylthio)methyl)-4-chlorobenzene

1-(bis(cyclohexylthio)methyl)-4-chlorobenzene

4-[(4-Chloro-phenyl)-cyclohexylsulfanyl-methylsulfanyl]-pyridine

4-[(4-Chloro-phenyl)-cyclohexylsulfanyl-methylsulfanyl]-pyridine

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In acetonitrile at 0 - 25℃; for 16h;96%
pyridine-4-thiol
4556-23-4

pyridine-4-thiol

chloro(2,6-bis(dimethylaminomethyl)phenyl-N,C,N)platinum(II)
663164-11-2

chloro(2,6-bis(dimethylaminomethyl)phenyl-N,C,N)platinum(II)

[2,6-bis(dimethylaminomethyl)phenylplatinum]-4-thiolatopyridine
881888-00-2

[2,6-bis(dimethylaminomethyl)phenylplatinum]-4-thiolatopyridine

Conditions
ConditionsYield
With sodium hydroxide In ethanol under N2 atm. Pt complex, 4-mercaptopyridine, and NaOH in EtOH were stirred for 2 h; solvent was evapd. in vacuo, residue was dissolved in CH2Cl2 in air and filtered, filtrate was evapd.; elem. anal.;96%

4556-23-4Relevant articles and documents

Formation and reactions of S-nitroso proteins

Noble, Darren R.,Williams, D. Lyn H.

, p. 13 - 17 (2001)

Nitrosation of Bovine Serum Albumin (BSA) by nitrous acid occurs in two stages: a rapid step, which is consistent with an S-nitrosation reaction of a free cysteine unit, followed by a slower reaction which is consistent with an N-nitrosation reaction of a tryptophan residue. The fast reaction is catalysed by chloride and bromide ions (as is the reaction of free cysteine), whereas the slower reaction is not halide ion catalysed (like the reaction of tryptophan). Kinetic results were obtained for both reactions. The derived rate constants for the first stage for the reaction of ClNO and BrNO are reasonably close to the reported values for the reactions of cysteine. The second stage is a reversible process and we can estimate from measured infinity values and also from the variation in the measured rate constant for reactions at different [HNO2], values for the equilibrium constant of 3500 +/- 200 and 2600 +/- 200 dm3 mol-1 which compare reasonably with the reported value for the reaction of tryptophan of 850 dm3 mol-1. The pKa values of the cysteine residue in both BSA and Human Serum Albumin (HSA) were determined from rate measurements of the reactions with dipyridin-4-yl disulfide (4-aldrithiol), and yielded values of 8.32 and 8.18 respectively, which are close to the accepted value of 8.4 for cysteine itself, and which are substantially higher than the much quoted literature values. The S-nitroso derivatives of both BSA and HSA generated in solution (at ca. 1 x 10-4 mol dm-3) showed very little sign of decomposition at pH 7.4 when measured spectrophotometrically, even in the presence of added Cu2+. There was, however, clear evidence of rapid decomposition at much lower reactant concentration (ca. 1 x 10-6 mol dm-3) yielding nitric oxide in increasing amounts and rates, as Cu2+ is added. These results are discussed in terms of the complexation of the Cu2+ catalyst at different albumin derivative concentrations. Transnitrosation between the S-nitroso derivatives of both BSA and HSA and excess cysteine occurred very readily. These experiments were carried out in the presence of added Cu2+, and the decomposition of the resulting S-nitrosocysteine (S-NOCys) was monitored. The results support the suggestion that S-nitroso proteins can, in theory, act as a reservoir for NO which can readily be made available, either by the Cu2+-catalysed reaction, or more readily by a direct NO+ transfer to a low molecular weight thiol, such as cysteine, which is much more prone to yield NO rapidly and quantitatively by the Cu2+-catalysed pathway. The S-nitroso derivative of BSA also underwent a relatively slow decomposition reaction initiated by cysteine, even in the presenc...

Ago-allosteric modulators of human glucagon-like peptide 2 receptor

Yamazaki, Kazuto,Terauchi, Hiroki,Iida, Daisuke,Fukumoto, Hironori,Suzuki, Shuichi,Kagaya, Takaki,Aoki, Mika,Koyama, Koichiro,Seiki, Takashi,Takase, Kazuma,Watanabe, Misako,Arai, Tohru,Tsukahara, Kappei,Nagakawa, Junichi

, p. 6126 - 6135 (2012/10/30)

Glucagon-like peptide 2 (GLP-2) is an intestinotropic peptide that binds to GLP-2 receptor (GLP-2R), a class-B G protein-coupled receptor (GPCR). Few synthetic agonists have been reported so far for class-B GPCRs. Here, we report the first scaffold compounds of ago-allosteric modulators for human GLP-2R, derived from methyl 2-{[(2Z)-2-(2,5-dichlorothiophen-3-yl)-2-(hydroxyimino) ethyl]sulfanyl}benzoate (compound 1).

NOVEL AROMATIC COMPOUND AND POLYARYLENE COPOLYMER HAVING NITROGEN-CONTAINING HETEROCYCLE INCLUDING SULFONIC ACID GROUP IN SIDE CHAIN

-

, (2010/06/22)

Provided is a solid polymer electrolyte having increased heat resistance and high proton conductivity and a proton conductive membrane composed of the electrolyte. Also provided is a copolymer having a sulfonic acid group. The copolymer includes a repeating unit represented by Formula (1): (in the formula, Y denotes at least one kind of structure selected from the group consisting of —CO—, —SO2—, —SO—, —CONH—, —COO—, —(CF2)l— (l is an integer of 1 to 10), and —C(CF3)2—; W denotes at least one kind of structure selected from the group consisting of a direct bond, —CO—, —SO2—, —SO—, —CONH—, —COO—, —(CF2)l— (l is an integer of 1 to 10), —C(CF3)2—, —O—, and —S—; Z denotes a direct bond or at least one kind of structure selected from the group consisting of —(CH2)l—(l is an integer of 1 to 10), —C(CH3)2—, —O—, —S—, —CO—, and —SO2—; R30 denotes a nitrogen-containing aromatic ring having a substituent represented by —SO3H, —O(CH2)hSO3H, or —O(CF2)hSO3H (h is an integer of 1 to 12); p is an integer of 0 to 10; q is an integer of 0 to 10; r is an integer of 1 to 5; and k is an integer of 0 to 4).

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