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Diisopropyl tartrate information


Diisopropyl tartrate
Names
IUPAC name
Di(propan-2-yl) 2,3-dihydroxybutanedioate
Other names
Diisopropyl 2,3-dihydroxysuccinate
Diisopropyl tartrate
Bis(1-methylethyl) ester of 2,3-dihydroxybutanedioic acid
DIPT
Identifiers
CAS Number
  • 2217-15-4 checkY
3D model (JSmol)
  • (−)-isomer: Interactive image
  • Interactive image
ChemSpider
  • 101254 (−)-isomer ☒N
ECHA InfoCard 100.017.009 Edit this at Wikidata
EC Number
  • 218-709-0
PubChem CID
  • 102768 (−)-isomer
  • 112972
UNII
  • 7Z907X7UEY checkY
InChI
  • InChI=1S/C10H18O6/c1-5(2)15-9(13)7(11)8(12)10(14)16-6(3)4/h5-8,11-12H,1-4H3/t7-,8-/m0/s1 ☒N
    Key: XEBCWEDRGPSHQH-YUMQZZPRSA-N ☒N
SMILES
  • (−)-isomer: CC(C)OC(=O)C(C(C(=O)OC(C)C)O)O
  • O=C(OC(C)C)[C@@H](O)[C@H](O)C(=O)OC(C)C
Properties
Chemical formula
C10H18O6
Molar mass 234.25 g/mol
Density 1.117 g/mL
Boiling point 152 °C (306 °F; 425 K) at 16 kPa
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Diisopropyl tartrate (DIPT) is a diester of tartaric acid. It has a two chiral carbon atoms giving rise to three stereoisomeric variants. It is commonly used in asymmetric synthesis as a catalyst and as chiral building block for pharmaceuticals and agrochemicals. Its main application is in Sharpless epoxidation, where it serves as a chiral ligand to titanium after reaction with titanium isopropoxide.[1]

  1. ^ Katsuki, Tsutomu; Sharpless, K. Barry (1980). "The first practical method for asymmetric epoxidation". J. Am. Chem. Soc. 102 (18): 5974. doi:10.1021/ja00538a077.

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Diisopropyl tartrate

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Diisopropyl tartrate (DIPT) is a diester of tartaric acid. It has a two chiral carbon atoms giving rise to three stereoisomeric variants. It is commonly...

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Tartaric acid

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sodium tartrate), which has unusual piezoelectric properties tartar emetic (antimony potassium tartrate), a resolving agent. Diisopropyl tartrate is used...

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Borylation

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Palkowitz, Alan D. (January 1988). "Enantioselective synthesis using diisopropyl tartrate modified (E)- and (Z)-crotylboronates: Reactions with achiral aldehydes"...

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Organolithium reagent

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1351/pac198860111627. Roush, W.R.; et al. (1988). "Enantioselective synthesis using diisopropyl tartrate modified (E)- and (Z)-crotylboronates: Reactions with achiral aldehydes"...

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Kinetic resolution

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number of different tartrates can be used for the catalyst; a representative scheme is shown below utilizing diisopropyl tartrate. This method has seen...

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Keck asymmetric allylation

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the reaction, also developed the use of diisopropyl tartrate in a chiral poisoning strategy. Diisopropyl tartrate, racemic BINOL, Ti(OiPr)4, phenylaldehyde...

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Rivastigmine

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drugs (NSAIDs) or who have a history of peptic ulcer disease. Rivastigmine tartrate is a white to off-white, fine crystalline powder that is both lipophilic...

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Edgewood Arsenal human experiments

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Lewisite (L) EA 1036 - O-mustard EA 1053 - Nitrogen mustard 3 EA 1152 - Diisopropyl fluorophosphate (DFP) EA 1205 - Tabun (GA) EA 1208 - Sarin (GB) EA 1210...

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CB military symbol

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Saxitoxin Material Testing Program EA (Edgewood Arsenal) numbers: EA 1152 - Diisopropyl fluorophosphate (DFP) EA 1205 - Tabun (GA) EA 1208 - Sarin (GB) EA 1210...

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California Proposition 65 list of chemicals

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(ETS) – Epichlorohydrin 106-89-8 Epoxiconazole 135319-73-2 Ergotamine tartrate 379-79-3 Erionite 12510-42-8; 66733-21-9 Estradiol 50-28-2 Estragole 140-67-0...

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Physostigmine

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gives optically pure product only after eight recrystallizations of its tartrate salt. Second, the reductive amination going from compound 8 to compound...

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Caffeine

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can also be absorbed rectally, evidenced by suppositories of ergotamine tartrate and caffeine (for the relief of migraine) and of chlorobutanol and caffeine...

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List of compounds with carbon number 8

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tetramethylbutanedioic acid 630-51-3 C8H14O5 diethyl malate 626-11-9 C8H14O6 diethyl tartrate 87-91-2 C8H14O6 triethylene glycol diformate 5451-65-0 C8H15Br cyclooctyl...

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List of compounds with carbon number 12

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acid 693-23-2 C12H22O4 tetraethylsuccinic acid 4111-60-8 C12H22O6 dibutyl tartrate 87-92-3 C12H22O6 oligoethylene butylene glycol adipate 26570-73-0 C12H22O11...

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