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Merck
CN

43749

1,3-二噻烷-2-甲酸乙酯

technical, ≥90% (GC)

别名:

乙醛酸乙酯三亚甲基缩硫醛

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关于此项目

经验公式(希尔记法):
C7H12O2S2
化学文摘社编号:
分子量:
192.30
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
243-838-4
Beilstein/REAXYS Number:
1424352
MDL number:
Assay:
≥90% (GC)
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InChI key

ANEDZEVDORCLPM-UHFFFAOYSA-N

InChI

1S/C7H12O2S2/c1-2-9-6(8)7-10-4-3-5-11-7/h7H,2-5H2,1H3

SMILES string

CCOC(=O)C1SCCCS1

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

Quality Level

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.

pictograms

Flame

signalword

Warning

hcodes

Hazard Classifications

Flam. Liq. 3

存储类别

3 - Flammable liquids

wgk

WGK 3

flash_point_f

131.0 °F - closed cup

flash_point_c

55 °C - closed cup

ppe

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

法规信息

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分析证书(COA)

Lot/Batch Number

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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
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)
Phase Transfer Catalysis for Preparation and Alkylation of Ethyl 1,3-Dithiane-2-carboxylate.
Lissel M.
Synthetic Communications, 11(4), 343-346 (1981)
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)

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