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Merck

213969

(−)-Diethyl D-tartrate

≥99%

Synonym(s):

D-(−)-Tartaric acid diethyl ester

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About This Item

Linear Formula:
HO2CCCH(OH)CH(OH)CO2H
CAS Number:
Molecular Weight:
206.19
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
EC Number:
237-458-8
Beilstein/REAXYS Number:
1727143
MDL number:
Assay:
≥99%

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Quality Level

assay

≥99%

optical activity

[α]23/D −8.5°, neat

optical purity

ee: ≥99% (GLC)

refractive index

n20/D 1.446 (lit.)

bp

162 °C/19 mmHg (lit.)

density

1.205 g/mL at 20 °C (lit.)

functional group

ester, hydroxyl

SMILES string

CCOC(=O)[C@@H](O)[C@H](O)C(=O)OCC

InChI

1S/C8H14O6/c1-3-13-7(11)5(9)6(10)8(12)14-4-2/h5-6,9-10H,3-4H2,1-2H3/t5-,6-/m0/s1

InChI key

YSAVZVORKRDODB-WDSKDSINSA-N

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This Item
227803163457420395
assay

≥99%

assay

98%

assay

99%

assay

99%

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

100

bp

162 °C/19 mmHg (lit.)

bp

-

bp

163 °C/23 mmHg (lit.)

bp

105-107 °C/1 mmHg (lit.)

density

1.205 g/mL at 20 °C (lit.)

density

1.119 g/mL at 20 °C (lit.)

density

1.238 g/mL at 25 °C (lit.)

density

0.972 g/mL at 25 °C (lit.)

refractive index

n20/D 1.446 (lit.)

refractive index

n20/D 1.439 (lit.)

refractive index

-

refractive index

n20/D 1.428 (lit.)

optical activity

[α]23/D −8.5°, neat

optical activity

[α]23/D −17°, neat

optical activity

[α]22/D +21°, c = 2.5 in H2O

optical activity

[α]20/D −57°, c = 1 in chloroform

Application

(-)-Diethyl D-tartrate can be used as a starting material in the synthesis of bioactive compounds such as (-)-kumausallene, syringolide 2 and (+)-exo-brevicomin.

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

200.1 °F - closed cup

flash_point_c

93.4 °C - closed cup

ppe

Eyeshields, Gloves


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A new expeditious synthesis of (+)-exo-brevicomin via efficient C? C bond formation of triflates.
Kotsuki H, et al.
Tetrahedron Letters, 30(30), 3999-4000 (1989)
Radical cyclization of ?-alkoxyacrylates: A formal synthesis of (-)-kumausallene.
Lee E, et al.
Tetrahedron Letters, 39(3), 317-318 (1998)
Synthesis and absolute configuration of syringolide 2, an elicitor from Pseudomonas syringae pv. tomato.
Kuwahara S, et al.
Tetrahedron Letters, 36(18), 3201-3202 (1995)
Naoki Miyakoshi et al.
The Journal of organic chemistry, 70(15), 6045-6052 (2005-07-16)
A highly stereoselective method for constructing a (2E)-methoxymethylidene-1,6-dioxaspiro[4.5]decane skeleton has been developed on the basis of the palladium(II)-catalyzed ring-closing reaction of the 3,4-dioxygenated-9-hydroxy-1-nonyn-5-one derivatives as a crucial step. The newly developed procedures could be successfully applied to the first total
Naoto Hama et al.
Organic letters, 13(4), 616-619 (2011-01-05)
A first total synthesis of broussonetine F from diethyl L-tartrate was achieved. The cornerstone of our synthesis was an orthoamide Overman rearrangement, which provided an allylic amino alcohol with complete diastereoselectivity.

Global Trade Item Number

SKUGTIN
213969-500G04061837639098
213969-5G04061837639104
213969-25G04061838773029

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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