196274

Thiomorpholine

Name: Thiomorpholine
Brand: ALDRICH

98%

Synonym(s):

Tetrahydro-2H-1,4-thiazine, Thiamorpholine

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About This Item

Empirical Formula (Hill Notation):

C₄H₉NS

CAS Number:

123-90-0

Molecular Weight:

103.19

Beilstein/REAXYS Number:

102550

EC Number:

204-660-2

MDL number:

MFCD00005974

UNSPSC Code:

12352100

PubChem Substance ID:

24851748

NACRES:

NA.22

Key Documents

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Quality Level

100

assay

98%

refractive index

n20/D 1.538 (lit.)

bp

169 °C (lit.)

solubility

organic solvents: miscible(lit.)
water: miscible(lit.)

density

1.026 g/mL at 25 °C (lit.)

functional group

thioether

SMILES string

C1CSCCN1

InChI

1S/C4H9NS/c1-3-6-4-2-5-1/h5H,1-4H2

InChI key

BRNULMACUQOKMR-UHFFFAOYSA-N

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Show Differences

1 of 4

This Item	394467	195944	272361
Sigma-Aldrich 196274 Thiomorpholine	Sigma-Aldrich 394467 Morpholine	Sigma-Aldrich 195944 2-Thiopheneacetic acid	Sigma-Aldrich 272361 2,3-Diaminotoluene
assay 98%	assay ≥99.5%	assay 98%	assay 97%
Quality Level 100	Quality Level 200	Quality Level 100	Quality Level 100
solubility organic solvents: miscible(lit.), water: miscible(lit.)	solubility water: miscible	solubility -	solubility -
bp 169 °C (lit.)	bp 129 °C (lit.)	bp 160 °C/22 mmHg (lit.)	bp -
density 1.026 g/mL at 25 °C (lit.)	density 0.996 g/mL at 25 °C (lit.)	density -	density -
refractive index n20/D 1.538 (lit.)	refractive index n20/D 1.454 (lit.)	refractive index -	refractive index -

General description

Thiomorpholine forms complexes with Cu(II), Pt(II) and Ni(II) salts and their catalytic activity has been investigated[1].

Application

Thiomorpholine has been used in the preparation of:

N-Boc-α-alkyl-β-(sec-amino)alanines[2]
thiomorpholine-N-borane[3]

pictograms

GHS05

signalword

Danger

hcodes

H314

pcodes

P280 - P301 + P330 + P331 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 + P310 - P501

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

145.4 °F - closed cup

flash_point_c

63 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Synthesis and comparative reactivity of thiomorpholine-borane: aqueous hydrolysis and oxidation by hypochlorite.

Amezcua CA, et al.

Inorgorganica Chimica Acta, 290(1), 80-85 (1999)

Complexation, thermal and catalytic studies of N-substituted piperazine, morpholine and thiomorpholine with some metal ions.

Mesut Kacan et al.

Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 118, 572-577 (2013-10-05)

Several Cu(II), Pt(II) and Ni(II) complexes of N-substituted, piperazine (NN donor), morpholine (NO donor) and thiomorpholine (NS donor) derivatives were synthesized and their thermal behavior and catalytic activity in epoxidation reaction of cis-diphenylethylene were studied using oxygen sources NaOCl. The

Acetylenic TACE inhibitors. Part 3: Thiomorpholine sulfonamide hydroxamates.

J I Levin et al.

Bioorganic & medicinal chemistry letters, 16(6), 1605-1609 (2006-01-24)

A series of thiomorpholine sulfonamide hydroxamate TACE inhibitors, all bearing propargylic ether P1' groups, was explored. In particular, compound 5h has excellent in vitro potency against isolated TACE enzyme and in cells, oral activity in a model of TNF-alpha production

New antibacterial tetrahydro-4(2H)-thiopyran and thiomorpholine S-oxide and S,S-dioxide phenyloxazolidinones.

Upinder Singh et al.

Bioorganic & medicinal chemistry letters, 13(23), 4209-4212 (2003-11-19)

Combinatorial libraries of N-acylated 5-(S)-aminomethyloxazolidinone derivatives of S-oxide and S,S-dioxide tetrahydro-4(2H)-thiopyranyl and thiomorpholine phenyloxazolidinone series have been synthesized on a solid phase and evaluated for antimicrobial activity. Several novel potent leads have been identified, including orally active oxazolidinones with enhanced

An annulation reaction for the synthesis of morpholines, thiomorpholines, and piperazines from beta-heteroatom amino compounds and vinyl sulfonium salts.

Muhammad Yar et al.

Angewandte Chemie (International ed. in English), 47(20), 3784-3786 (2008-04-12)

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