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145289

Sigma-Aldrich

4-Chloro-2-methylthiopyrimidine

98%

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About This Item

Empirical Formula (Hill Notation):
C5H5ClN2S
CAS Number:
49844-90-8
Molecular Weight:
160.62
EC Number:
256-500-6
MDL number:
MFCD00006083
UNSPSC Code:
12352100
PubChem Substance ID:
24848713
NACRES:
NA.22

Assay

98%

refractive index

n20/D 1.6 (lit.)

bp

139-140 °C/36 mmHg (lit.)

mp

−2 °C (lit.)

density

1.381 g/mL at 25 °C (lit.)

SMILES string

CSc1nccc(Cl)n1

InChI

1S/C5H5ClN2S/c1-9-5-7-3-2-4(6)8-5/h2-3H,1H3

InChI key

DFOHHQRGDOQMKG-UHFFFAOYSA-N

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Application

4-Chloro-2-methylthiopyrimidine was used in the total synthesis of the marine alkaloid variolin B1 and 2-hydroxy-4-pyrimidinecarboxylic acid. It was used in the synthesis of 2,4-disubstituted pyrimidines, a novel class of KDR kinase inhibitors. It was used as building block in medicinal chemistry synthesis.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

145289-50G:
145289-BULK:
145289-VAR:
145289-10G:

Certificates of Analysis (COA)

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Peter J Manley et al.
Bioorganic & medicinal chemistry letters, 13(10), 1673-1677 (2003-05-06)
2,4-Disubstituted pyrimidines were synthesized as a novel class of KDR kinase inhibitors. Evaluation of the SAR of the screening lead compound 1 (KDR IC(50)=105 nM, Cell IC(50)=8% inhibition at 500 nM) led to the potent 3,5-dimethylaniline derivative 2d (KDR IC(50)=6
David D Davey et al.
Journal of medicinal chemistry, 50(6), 1146-1157 (2007-02-24)
By the screening of a combinatorial library for inhibitors of nitric oxide (NO) formation by the inducible isoform of nitric oxide synthase (iNOS) using a whole-cell assay, 2-(imidazol-1-yl)pyrimidines were identified. Compounds were found to inhibit the dimerization of iNOS monomers
Pyrimidines. XIII. 2-and 6-substituted 4-pyrimidinecarboxylic acids.
Daves GD, et al.
Journal of Heterocyclic Chemistry, 1(3), 130-133 (1964)
Regan J Anderson et al.
The Journal of organic chemistry, 70(16), 6204-6212 (2005-07-30)
The total synthesis of the marine alkaloid variolin B has been achieved in 8 steps and 17% overall yield, starting from commercially available 4-chloro-2-methylthiopyrimidine. The key reaction involves the tandem deoxygenation and cyclization of a triarylmethanol using a combination of
Mark H Norman et al.
Journal of medicinal chemistry, 50(15), 3497-3514 (2007-06-26)
The vanilloid receptor-1 (VR1 or TRPV1) is a member of the transient receptor potential (TRP) family of ion channels and plays a role as an integrator of multiple pain-producing stimuli. From a high-throughput screening assay, measuring calcium uptake in TRPV1-expressing

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