43749
Ethyl 1,3-dithiane-2-carboxylate
technical, ≥90% (GC)
Synonym(s):
Glyoxylic acid ethyl ester trimethylenemercaptal
Sign Into View Organizational & Contract Pricing
All Photos(2)
About This Item
Empirical Formula (Hill Notation):
C7H12O2S2
CAS Number:
Molecular Weight:
192.30
Beilstein:
1424352
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
grade
technical
Assay
≥90% (GC)
refractive index
n20/D 1.539 (lit.)
n20/D 1.541
bp
75-77 °C/0.2 mmHg (lit.)
density
1.22 g/mL at 25 °C (lit.)
functional group
ester
thioether
SMILES string
CCOC(=O)C1SCCCS1
InChI
1S/C7H12O2S2/c1-2-9-6(8)7-10-4-3-5-11-7/h7H,2-5H2,1H3
InChI key
ANEDZEVDORCLPM-UHFFFAOYSA-N
Looking for similar products? Visit Product Comparison Guide
General description
Ethyl 1,3-dithiane-2-carboxylate is an α-keto acid equivalent and bulky equivalent of acetate. It participates in syn-selective aldol reactions. It can be prepared from the reaction of ethyl diethoxyacetate and 1,3-propanedithiol in the presence of BF3/Et2O. Asymmetric oxidation of ethyl 1,3-dithiane-2-carboxylate by Modena protocol has been reported to afford trans bis-sulfoxide in 60% yield. Carbanion from ethyl 1,3-dithiane-2-carboxylate may be employed for the preparation of α-keto esters.
Signal Word
Warning
Hazard Statements
Hazard Classifications
Flam. Liq. 3
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
131.0 °F - closed cup
Flash Point(C)
55 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
Alkylation of the carbanion from methyl bis (ethylthio) acetate with alkyl and aralkyl halides.
Lerner LM.
The Journal of Organic Chemistry, 41(12), 2228-2229 (1976)
Convenient synthesis of α-keto esters.
Eliel EL and Hartmann AA.
The Journal of Organic Chemistry, 37(3), 505-506 (1972)
Varinder K. Aggarwal et al.
The Journal of organic chemistry, 63(21), 7306-7310 (2001-10-24)
Asymmetric oxidation of a range of 1,3-dithianes was studied using the Kagan protocol [CHP (4 equiv), (+)-DET (2 equiv), Ti(OiPr)(4) (1 equiv), and H(2)O (1 equiv) at -35 degrees C for 48 h]. 1,3-Dithiane itself gave monoxide (30% ee) and
L.A. Flippin et al.
Tetrahedron Letters, 26, 2977-2977 (1985)
Aldol condensations of ethyl 1,3-dithiolane-2-carsoxylate and ethyl 1, 3-dithiane-2-carboxylate with chiral aldehydes. Exceptional diastereoface selectivity from two convenient acetate equivalents.
Flippin LA and Dombroski MA.
Tetrahedron Letters, 26(25), 2977-2980 (1985)
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service