Ethyl 1,3-dithiane-2-carboxylate (HCID 88552)

Names & identifiers

Preferred name: Ethyl 1,3-dithiane-2-carboxylate
IUPAC: ethyl 1,3-dithiane-2-carboxylate
English name: Ethyl 1,3-dithiane-2-carboxylate
Molecular formula: C7H12O2S2
Molecular weight: 192.3

Names & synonyms

Ethyl 1,3-dithiane-2-carboxylate20462-00-41,3-Dithiane-2-carboxylic acid ethyl ester1,3-Dithiane-2-carboxylic acid, ethyl ester2-Carboethoxy-1,3-dithianeCarboethoxy-1,3-dithianeDRA87T4JKTEINECS 243-838-4ANEDZEVDORCLPM-UHFFFAOYSA-DTXSID501744272-(ethoxycarbonyl)-1,3-dithianeRefChem:138466

Show more names

1,3-dithioalkane-2-ethyl formateEthyl1,3-Dithiane-2-carboxylate>Ethyl 1,3-dithiane-2-carboxylate, 98+%ETHYL-1 3-DITHIANE-2-CARBOXYLATE 99% (&ETHYL 1,3-DITHIANE-2-CARBOXYLATE FOR SYN2-(2-phenylimino-3-thiazolidinyl)ethanol

DTXCID2096918243-838-4ANEDZEVDORCLPM-UHFFFAOYSA-NInChI=1/C7H12O2S2/c1-2-9-6(8)7-10-4-3-5-11-7/h7H,2-5H2,1H3MFCD00006657m-Dithiane-2-carboxylic acid, ethyl ester2-ethoxycarbonyl-1,3-dithiane[1,3]dithiane-2-carboxylic acid ethyl ester

Database identifiers

CAS: 20462-00-4
PubChem CID: 88552
DTXSID: DTXSID50174427
UNII: DRA87T4JKT
EC Number: 243-838-4
Nikkaji: J208.387F

Properties

Computed structural properties

XLogP: 2.1
Topological polar surface area: 76.9 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 3
Heavy atoms: 11
Formal charge: 0
Complexity: 132

Physicochemical properties

Melting point: 19 · 19-21°C
Boiling point: 75 · 75-77 °C/0.2 mmHg (lit.)
Density: 1.22 g/mL · 1.22 g/mL at 25 °C (lit.)
refractive index: 20 · n20/D 1.539(lit.)
Flash point: 130 °F · 130 °F
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
form: clear liquid
color: Colorless to Light yellow to Light orange
Water Solubility: Slightly miscible with water.
BRN: 1424352 · 1424352
InChI: InChI=1S/C7H12O2S2/c1-2-9-6(8)7-10-4-3-5-11-7/h7H,2-5H2,1H3
InChIKey: ANEDZEVDORCLPM-UHFFFAOYSA-N
SMILES: S1CCCSC1C(OCC)=O
CAS DataBase Reference: 20462 · 20462-00-4(CAS DataBase Reference)
FDA UNII: 87 T4JKT · DRA87T4JKT
NIST Chemistry Reference: 1 · Ethyl 1,3-dithiane-2-carboxylate(20462-00-4)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02
Signal word: Warning
Hazard statements: 226 · H226
Precautionary statements: 241 · P241-P280a-P501a-P210-P233-P240-P241+P242+P243-P280-P303+P361+P353-P403+P235-P501
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Risk Statements: 10 · 10
Safety Statements: 26 · 26-36/37/39-45
RIDADR: 3272 · UN 3272 3/PG 3
WGK Germany: 3 · 3
F: 9 · 9-13
HazardClass: 3 · 3
PackingGroup: III
HS Code: 29349990 · 29349990
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 3 · Flam. Liq. 3

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 2 items

Chemical: 1,3-Dithiane-2-carboxylic acid, ethyl ester

Ethyl 1,3-dithiane-2-carboxylate: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesFlam. Liq. 3 (100%)

Safety data

F: 9-13
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
ridadr: UN 3272 3/PG 3
hs_code: 29349990
risk_code: 10
Signal word: Warning
Symbol(GHS): GHS02
safety_code: 26-36/37/39-45
hazard_class: 3
Storage Class: 3 - Flammable liquids
packing_group: III
Hazard statements: H226
Hazard Classifications: Flam. Liq. 3
Precautionary statements: P241-P280a-P501a-P210-P233-P240-P241+P242+P243-P280-P303+P361+P353-P403+P235-P501

Chemistry & industry

Applications · 2 items

UsesEthyl 1,3-dithiane-2-carboxylate is used in syn-selective aldol reactions. It undergoes asymmetric oxidation to give trans bis-sulfoxide. It is used to generate carbanon, which finds application in the preparation of alfa- keto esters.

General DescriptionEthyl 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.

Preparation methods · 1 item

PreparationTo a solution of BF3. Et2O (57.5 mL, 0.454 mmol) in CHC13 (180 mL) heated at reflux was added dropwise, over a 1h period, a solution of 1,3-propanedithiol (22.7 mL, 0.227 mmol), followed by ethyl diethoxyacetate (40 g, 0.227 mmol) in CHCl3 (40 mL). The resulting mixture was heated for 30 minutes, and then cooled to rt. The cooled solution was washed 2 times with water, once with saturated aqueous NaHC03, and then re-washed with water. The combined organic phases were dried over MgS04, then evaporated to give 41 g (94%) of Ethyl 1,3-dithiane-2-carboxylate as a yellow oi. Yield: 94%