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About This Item
Linear Formula:
CH3SOC6H5
CAS Number:
Molecular Weight:
140.20
Beilstein:
1904976
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Assay
≥97%
form
crystals
refractive index
n20/D 1.5775 (lit.)
bp
139-140 °C/14 mmHg (lit.)
mp
26-29 °C (lit.)
functional group
sulfoxide
storage temp.
2-8°C
SMILES string
CS(=O)c1ccccc1
InChI
1S/C7H8OS/c1-9(8)7-5-3-2-4-6-7/h2-6H,1H3
InChI key
JXTGICXCHWMCPM-UHFFFAOYSA-N
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General description
(R)-methyl phenyl sulfoxide is an important pharmaceutical intermediate.
Application
Methyl phenyl sulfoxide has been used in the synthesis of:
- isotopically labelled 1, 3-dithiane, a useful labeled synthon
- nelfinavir, potent HIV-protease inhibitor
- sulfoximines and in studies on solvent-water partitioning
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
186.8 °F - closed cup
Flash Point(C)
86 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Nathalie Sauvonnet et al.
The Journal of cell biology, 168(1), 155-163 (2004-12-30)
Endocytosis is critical for many cellular functions. We show that endocytosis of the common gammac cytokine receptor is clathrin independent by using a dominant-negative mutant of Eps15 or RNA interference to knock down clathrin heavy chain. This pathway is synaptojanin
Sadagopan Raghavan et al.
The Journal of organic chemistry, 75(2), 498-501 (2009-12-17)
An asymmetric synthesis of nelfinavir is described starting from acrolein and (S)-methyl phenyl sulfoxide. The key features include (a) stereoselective preparation of a beta-protected amino-gamma,delta-unsaturated sulfoxide by the reaction of an alpha-sulfinyl carbanion with an unsaturated t-butyl sulfinylimine, (b) stereoselective
M H Abraham et al.
Journal of pharmaceutical sciences, 83(8), 1085-1100 (1994-08-01)
A general linear solvation energy equation has been used to analyze published partition coefficients in the systems water-octanol (613 solutes), water-hexadecane (370 solutes), water-alkane (200 solutes), and water-cyclohexane (170 solutes). The descriptors used in the equation are R2, an excess
Rodolfo A Martinez et al.
Journal of labelled compounds & radiopharmaceuticals, 57(5), 338-341 (2014-05-28)
The 1,3-dithiane is a protected formaldehyde anion equivalent that could serve as a useful labeled synthon. We report a facile synthesis of 1,3-[2-(13)C]- and 1,3-[2-(13)C, 2-(2)H2]dithiane in two steps from [(13)C]- or [(13) C, (2)H3 ]methyl phenyl sulfoxide. We have
Giorgio Celebre et al.
The journal of physical chemistry. B, 112(7), 2095-2101 (2008-01-31)
The conformational distribution of methyl phenyl sulfoxide (a molecule representative of a very important class of reagents widely used in asymmetric synthesis) has been studied in two different phases of matter (gas phase and solution) by a comprehensive approach including
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