4-Chloro-2-methylthiopyrimidine supplier

Name
4-Chloro-2-methylthiopyrimidine
EINECS 256-500-6
CAS No. 49844-90-8
Article Data12
CAS DataBase
Density 1.37 g/cm³
Solubility Not miscible or difficult to mix in water.
Melting Point -2 °C(lit.)
Formula C₅H₅ClN₂S
Boiling Point 243.1 °C at 760 mmHg
Molecular Weight 160.627
Flash Point 100.8 °C
Transport Information UN 1760 8/PG 2
Appearance Clear yellow to brown liquid
Safety 26-36/37/39-45
Risk Codes 34
Molecular Structure
Hazard Symbols C
Synonyms 2-(Methylthio)-4-chloropyrimidine;4-Chloro-2-(methylmercapto)pyrimidine;4-Chloro-2-(methylsulfanyl)pyrimidine;4-Chloro-2-(methylthio)pyrimidine;6-Chloro-2-methylthiopyrimidine;NSC 100866;
PSA 51.08000
LogP 1.85190

Synthetic route

: 5751-20-2
2-(methylsulfanyl)pyrimidin-4-ol

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

Conditions

Conditions	Yield
Stage #1: 2-(methylsulfanyl)pyrimidin-4-ol With trichlorophosphate In N,N-dimethyl-formamide; toluene at 20℃; for 0.5h; Stage #2: With thionyl chloride In N,N-dimethyl-formamide; toluene at 20 - 80℃; for 1h; Time; Solvent; Reagent/catalyst;	88.3%
With trichlorophosphate at 80℃;
With trichlorophosphate In neat (no solvent) at 80℃; for 7h; Inert atmosphere;

: 5751-20-2
2-Methylthiouracil

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

Conditions

Conditions	Yield
With thionyl chloride In dichloromethane; N,N-dimethyl-formamide at 40℃; for 3h;	87.6%
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 40℃; for 3h;	87.6%
With trichlorophosphate
With trichlorophosphate

: 5751-20-2
2-methylthio-1H-pyrimidin-4-one

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

Conditions

Conditions	Yield
With trichlorophosphate 1) reflux, 1.75 h, 2) r.t., overnight;

4-oxy-2-methylsulfanyl-pyrimidine hydrochloride: 4-oxy-2-methylsulfanyl-pyrimidine hydrochloride

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

Conditions

Conditions	Yield
With phosphorus pentachloride; trichlorophosphate

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 97229-11-3
4-chloro-2-methanesulfonylpyrimidine

Conditions

Conditions	Yield
With hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide In ethanol; water at 0℃; for 24h; Inert atmosphere;	99%
With chromium(VI) oxide; periodic acid In ethyl acetate; acetonitrile at 0℃; for 1.75h;	94%
With hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide In ethanol at 0 - 20℃; Inert atmosphere;	85.7%

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 1122-74-3
4-iodo-2-(methylthio)pyrimidine

Conditions

Conditions	Yield
With hydrogen iodide In water at 20℃; for 8h;	99%
With hydrogen iodide In water at 20℃; for 16h;	98%
With hydrogen iodide In water at 20℃; for 72h;	95%

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 100379-00-8
2,6-dimethylbenzene boronic acid

: 4-(2,6-dimethylphenyl)-2-(methylthio)pyrimidine

Conditions

Conditions	Yield
With potassium carbonate; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) In water; toluene for 12h; Suzuki-Miyaura cross-coupling; Heating;	99%
With potassium carbonate; PdCl2[P(tBu)2(p-Me2NC6H4)]2 In water; toluene at 100℃; Suzuki-Miyaura cross-coupling;	99%

: 51-17-2
benzoimidazole

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 1-(2-(methylthio)pyrimidin-4-yl)-1H-benzo[d]imidazole

Conditions

Conditions	Yield
With triethylamine In neat (no solvent) at 80℃; for 0.166667h; Microwave irradiation; Green chemistry;	99%
With NaH In N,N-dimethyl-formamide
With NaH In N,N-dimethyl-formamide
With triethylamine In N,N-dimethyl-formamide at 60 - 120℃; Microwave irradiation;

: 95-14-7
1,2,3-Benzotriazole

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: C11H9N5S*ClH

Conditions

Conditions	Yield
In neat (no solvent) at 80℃; for 0.0833333h; Microwave irradiation; Green chemistry;	99%

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 2-cyclobutyl-4-(methylsulfonyl)aniline

: N-(2-cyclobutyl-4-(methylsulfonyl)phenyl)-2-(methylthio)pyrimidin-4-amine

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In isopropyl alcohol at 70℃; for 22.6667h; Inert atmosphere;	99%

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 670-95-1
4-Phenylimidazole

: 1244039-66-4
C14H12N4S

Conditions

Conditions	Yield
Stage #1: 4-Phenylimidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1.16667h; Stage #2: 4-Chloro-2-methylthiopyrimidine In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h;	98.4%

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 940875-00-3
1-(2-hydroxybenzyl)-3-(3-t-butyl-1-p-tolyl-1H-pyrazol-5-yl)urea

: 940870-62-2
1-(2-(2-(methylthio)pyrimidin-4-yloxy)benzyl)-3-(3-t-butyl-1-p-tolyl-1H-pyrazol-5-yl)urea

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 22h;	98%

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 4-azido-2-(methylthio)pyrimidine

Conditions

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide at 20℃; for 72h;	98%
With sodium azide In N,N-dimethyl-formamide

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 6146-52-7
5-nitroindole

: 1-(2-(methylthio)pyrimidin-4-yl)-5-nitro-1H-indole

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃;	98%

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 89694-48-4
5-chloro-2-methoxyphenyl boronic acid

: 1262148-80-0
4-(5-chloro-2-methoxyphenyl)-2-methylsulfanylpyrimidine

Conditions

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene for 1h; Suzuki Coupling; Reflux;	97%

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 959236-97-6
4-bromo-2-methylsulfanylpyrimidine

Conditions

Conditions	Yield
With trimethylsilyl bromide In acetonitrile at 40℃; for 30h;	96%
With trimethylsilyl bromide In acetonitrile at 40℃; for 24h; Inert atmosphere;	96%
With trimethylsilyl bromide In acetonitrile at 40℃; for 24h; Inert atmosphere;	95%

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 637-44-5
phenylpropyolic acid

: C13H10N2S

Conditions

Conditions	Yield
With bis[dicyclohexyl(2,4,6-triisopropyl-[1,1':3',1''-terphenyl]-2-yl)phosphane]palladium(II) dichloride; caesium carbonate In tetrahydrofuran at 80℃; for 7h;	96%

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 97229-10-2
4-chloro-2-(methylsulfinyl)pyrimidine

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 24h;	95%
With manganese(II) triflate; 1-Adamantanecarboxylic acid; C32H38N4O2; dihydrogen peroxide In acetonitrile at -30℃; for 0.5h; enantioselective reaction;	85%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 25℃; Cooling with ice;

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 5720-07-0
4-methoxyphenylboronic acid

: 148990-17-4
4-(4-methoxyphenyl)-2-(methylsulfanyl)pyrimidine

Conditions

Conditions	Yield
With potassium carbonate; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) In water; toluene for 12h; Suzuki-Miyaura cross-coupling; Heating;	95%
With potassium carbonate; PdCl2[P(tBu)2(p-Me2NC6H4)]2 In water; toluene at 100℃; Suzuki-Miyaura cross-coupling;	95%

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 577-71-9
3,4-dinitophenol

: 952490-61-8
4-(3,4-dinitro-phenoxy)-2-methylsulfanyl-pyrimidine

Conditions

Conditions	Yield
at 150℃; for 2h;	95%
at 150℃; for 2h;

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 118062-05-8
2,3,4-trimethoxyphenylboronic acid

: 634611-62-4
C14H16N2O3S

Conditions

Conditions	Yield
Stage #1: 4-Chloro-2-methylthiopyrimidine; 2,3,4-trimethoxyphenylboronic acid With sodium carbonate In 1,4-dioxane; water at 20℃; for 0.0833333h; Stage #2: tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 110℃; for 16h;	95%

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 536-74-3
phenylacetylene

: C13H10N2S

Conditions

Conditions	Yield
With potassium phosphate; bis[dicyclohexyl(2,4,6-triisopropyl-[1,1':3',1''-terphenyl]-2-yl)phosphane]palladium(II) dichloride In acetonitrile at 90℃; for 6h; Sonogashira Cross-Coupling;	95%

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 7358-93-2
3‐cyclopropyl‐2‐propynoic acid

: C10H10N2S

Conditions

Conditions	Yield
With bis[dicyclohexyl(2,4,6-triisopropyl-[1,1':3',1''-terphenyl]-2-yl)phosphane]palladium(II) dichloride; caesium carbonate In tetrahydrofuran at 80℃; for 5h;	95%

: 110238-91-0
tetrahydropyran-4-carboxylic acid methyl ester

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: methyl 4-(2-(methylthio)pyrimidin-4-yl)tetrahydro-2H-pyran-4-carboxylate

Conditions

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at 30℃; for 0.0833333h;	95%
With lithium hexamethyldisilazane In tetrahydrofuran at 30℃; for 0.0833333h;	95%
With lithium hexamethyldisilazane In tetrahydrofuran at 30℃; for 0.0833333h;	95%
With lithium hexamethyldisilazane In tetrahydrofuran at 30℃; for 0.0833333h;	95%

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 75-50-3
trimethylamine

: 6622-64-6
Trimethyl-4-(2-methylthiopyrimidinyl)ammoniumchlorid

Conditions

Conditions	Yield
In benzene 1) 0 deg C; 2) room temperature, 1h;	94%

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 126747-14-6
4-cyanophenylboronic acid

: 874778-91-3
4-(2-methylsulfanylpyrimidin-4-yl)benzonitrile

Conditions

Conditions	Yield
With potassium carbonate; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) In water; toluene for 12h; Suzuki-Miyaura cross-coupling; Heating;	94%
With potassium carbonate; PdCl2[P(tBu)2(p-Me2NC6H4)]2 In water; toluene at 100℃; Suzuki-Miyaura cross-coupling;	94%

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 108-95-2
phenol

A: 2-methylthio-4-phenoxypyrimidine

B: 131860-90-7
(E)-methyl 2-[2-(4-phenoxypyrimidin-2-yloxy)phenyl]-3-methoxypropenoate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide	A 94% B n/a

...Expand

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 100-02-7
4-nitro-phenol

: 307309-31-5
2-methylsulfanyl-4-(4-nitrophenoxy)-pyrimidine

Conditions

Conditions	Yield
Stage #1: 4-nitro-phenol With sodium hydride at 0℃; for 0.5h; Stage #2: 4-Chloro-2-methylthiopyrimidine at 70 - 80℃; for 16h;	94%

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 41748-71-4
4-aminoindazole

: 945396-85-0
N-(2-methylsulfanylpyrimidin-4-yl)-1H-indazol-4-amine

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; butan-1-ol at 80℃; for 4h;	93%

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 178993-28-7
2-ethoxy-4-fluorobenzenamine

: N-(2-ethoxy-4-fluorophenyl)-2-(methylthio)pyrimidin-4-amine

Conditions

Conditions	Yield
With hydrogenchloride In water; isopropyl alcohol at 80℃; for 4h;	93%

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 7486-35-3
tri-n-butyl(vinyl)tin

: 131467-05-5
2-methylthio-4-vinylpyrimidine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In 1,2-dichloro-ethane at 70℃; for 48h;	92%
With tetrakis(triphenylphosphine) palladium(0) In 1,2-dichloro-ethane at 70℃; for 48h; Stille Cross Coupling;	92%
With tetrakis(triphenylphosphine) palladium(0) In 1,2-dichloro-ethane at 70℃; for 48h; Stille Cross Coupling;	92%

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 174669-73-9
(2-fluoro-pyridin-3-yl)boronic acid

: 4-(2-fluoropyridin-3-yl)-2-(methylthio)pyrimidine

Conditions

Conditions	Yield
With potassium hydrogencarbonate; PdCl2[P(tBu)2(p-Me2NC6H4)]2 In water; acetonitrile at 100℃; Suzuki-Miyaura cross-coupling;	92%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere;	73%

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: 94444-96-9
5-methoxy-1H-indazole

: 5-methoxy-1-(2-(methylthio)pyrimidin-4-yl)-1H-indazole

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 2h; Inert atmosphere;	92%

: 49844-90-8
4-Chloro-2-methylthiopyrimidine

: tert-butyl 4-(4-(((tert-butyldimethylsilyl)oxy)-methyl)-1H-1,2,3-triazol-1-yl)piperidine-1-carboxylate

: tert-butyl 4-(4-(((tert-butyldimethylsilyl)oxy)-methyl)-5-(2-(methylthio)pyrimidin-4-yl)-1H-1,2,3-triazol-1-yl)-piperidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: tert-butyl 4-(4-(((tert-butyldimethylsilyl)oxy)-methyl)-1H-1,2,3-triazol-1-yl)piperidine-1-carboxylate With n-butyllithium In tetrahydrofuran; hexane Cooling with acetone-dry ice; Stage #2: With zinc(II) chloride In tetrahydrofuran; hexane Cooling with acetone-dry ice; Stage #3: 4-Chloro-2-methylthiopyrimidine With (2‑dicyclohexylphosphino‑2′,6′‑dimethoxybiphenyl)[2‑(2′‑amino‑1,1′‑biphenyl)]palladium(II) methanesulfonate In tetrahydrofuran; hexane at 60℃; for 18h; Cooling with acetone-dry ice;	92%

Yield

Stage #1: tert-butyl 4-(4-(((tert-butyldimethylsilyl)oxy)-methyl)-1H-1,2,3-triazol-1-yl)piperidine-1-carboxylate With n-butyllithium In tetrahydrofuran; hexane Cooling with acetone-dry ice;
Stage #2: With zinc(II) chloride In tetrahydrofuran; hexane Cooling with acetone-dry ice;
Stage #3: 4-Chloro-2-methylthiopyrimidine With (2‑dicyclohexylphosphino‑2′,6′‑dimethoxybiphenyl)[2‑(2′‑amino‑1,1′‑biphenyl)]palladium(II) methanesulfonate In tetrahydrofuran; hexane at 60℃; for 18h; Cooling with acetone-dry ice;

92%

4-Chloro-2-methylthiopyrimidine Specification

The IUPAC name of 4-Chloro-2-methylthiopyrimidine is 4-chloro-2-methylsulfanylpyrimidine. With the CAS registry number 49844-90-8 and EINECS 256-500-6, it is also named as pyrimidine, 4-chloro-2-(methylthio)-. The product's categories are Halides; Pyrazines, Pyrimidines & Pyridazines; Pyrimidine; Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks; Pyrimidines; Pyrimidines Heterocyclic Building Blocks. It is clear yellow to brown liquid which should be sealed in the container and stored in the cool and dry place. Additionally, people should ensure that the workplace has well-ventilated equipment.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.61; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.61; (4)ACD/LogD (pH 7.4): 1.61; (5)ACD/BCF (pH 5.5): 9.77; (6)ACD/BCF (pH 7.4): 9.77; (7)ACD/KOC (pH 5.5): 177.89; (8)ACD/KOC (pH 7.4): 177.89; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 51.08 Å²; (13)Index of Refraction: 1.594; (14)Molar Refractivity: 39.81 cm³; (15)Molar Volume: 117.2 cm³; (16)Polarizability: 15.78×10^-24 cm³; (17)Surface Tension: 58.5 dyne/cm; (18)Density: 1.37 g/cm³; (19)Flash Point: 100.8 °C; (20)Enthalpy of Vaporization: 46.06 kJ/mol; (21)Boiling Point: 243.1 °C at 760 mmHg; (22)Vapour Pressure: 0.0511 mmHg at 25°C.

Uses of 4-Chloro-2-methylthiopyrimidine: It can react with tributyl-vinyl stannane to get 2-methylthio-4-vinylpyrimidine. This reaction needs reagent tetrakis(triphenyl phosphine)palladium(0) and solvent 1,2-dichloro-ethane at temperature of 70 °C. The reaction time is 48 hours. The yield is 92%.

4-Chloro-2-methylthiopyrimidine can react with tributyl-vinyl stannane to get 2-methylthio-4-vinylpyrimidine

When you are using this chemical, please be cautious about it as the following:
It can cause burns. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
1. SMILES:Clc1nc(SC)ncc1
2. InChI:InChI=1/C5H5ClN2S/c1-9-5-7-3-2-4(6)8-5/h2-3H,1H3
3. InChIKey:DFOHHQRGDOQMKG-UHFFFAOYAB

Product Name

4-Chloro-2-methylthiopyrimidine

Synthetic route

4-Chloro-2-methylthiopyrimidine Specification

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