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Showing metabocard for 1,1-Dimethoxyethane (HMDB0030061)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:34:30 UTC
Update Date2023-02-21 17:19:27 UTC
HMDB IDHMDB0030061
Secondary Accession Numbers
  • HMDB30061
Metabolite Identification
Common Name1,1-Dimethoxyethane
Description1,1-Dimethoxyethane, also known as dimethyl acetal, belongs to the class of organic compounds known as acetals. Acetals are compounds having the structure R2C(OR')2 ( R' not Hydrogen) and thus diethers of geminal diols. Originally, the term was confined to derivatives of aldehydes (one R = H), but it now applies equally to derivatives of ketones (neither R = H ). Mixed acetals have different R' groups. 1,1-Dimethoxyethane is a sweet, alcohol, and ether tasting compound. 1,1-Dimethoxyethane has been detected, but not quantified in, a few different foods, such as blackberries (Rubus), evergreen blackberries (Rubus laciniatus), and figs (Ficus carica). This could make 1,1-dimethoxyethane a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 1,1-Dimethoxyethane.
Structure
Data?1676999967
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0030061 (1,1-Dimethoxyethane)


  Mrv0541 05061304592D          

  6  5  0  0  0  0            999 V2000
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
M  END
Download

3D MOL for HMDB0030061 (1,1-Dimethoxyethane)

HMDB0030061
     RDKit          3D
1,1-Dimethoxyethane
 16 15  0  0  0  0  0  0  0  0999 V2000
   -1.3175   -0.8054    1.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6331    0.3902    1.2676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0504    0.3851    0.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6814    1.4762   -0.8456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3273    0.5204    0.0533 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9870   -0.5299   -0.5687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1185   -0.9658    0.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6181   -1.6794    1.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7381   -0.8927    2.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2695   -0.5648   -0.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7760    1.3648   -0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3947    2.4765   -0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3513    1.2224   -1.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0756   -0.3208   -0.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7563   -0.6077   -1.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8025   -1.4689   -0.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
  4 13  1  0
  6 14  1  0
  6 15  1  0
  6 16  1  0
M  END
Download

3D SDF for HMDB0030061 (1,1-Dimethoxyethane)


  Mrv0541 05061304592D          

  6  5  0  0  0  0            999 V2000
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030061

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(C)OC

> <INCHI_IDENTIFIER>
InChI=1S/C4H10O2/c1-4(5-2)6-3/h4H,1-3H3

> <INCHI_KEY>
SPEUIVXLLWOEMJ-UHFFFAOYSA-N

> <FORMULA>
C4H10O2

> <MOLECULAR_WEIGHT>
90.121

> <EXACT_MASS>
90.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
10.02839889383463

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,1-dimethoxyethane

> <ALOGPS_LOGP>
0.26

> <JCHEM_LOGP>
0.4172077526666663

> <ALOGPS_LOGS>
0.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.991941734072269

> <JCHEM_POLAR_SURFACE_AREA>
18.46

> <JCHEM_REFRACTIVITY>
23.707799999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,1-dimethoxyethane

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0030061 (1,1-Dimethoxyethane)

HMDB0030061
     RDKit          3D
1,1-Dimethoxyethane
 16 15  0  0  0  0  0  0  0  0999 V2000
   -1.3175   -0.8054    1.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6331    0.3902    1.2676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0504    0.3851    0.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6814    1.4762   -0.8456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3273    0.5204    0.0533 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9870   -0.5299   -0.5687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1185   -0.9658    0.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6181   -1.6794    1.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7381   -0.8927    2.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2695   -0.5648   -0.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7760    1.3648   -0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3947    2.4765   -0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3513    1.2224   -1.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0756   -0.3208   -0.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7563   -0.6077   -1.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8025   -1.4689   -0.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
  4 13  1  0
  6 14  1  0
  6 15  1  0
  6 16  1  0
M  END
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PDB for HMDB0030061 (1,1-Dimethoxyethane)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.310   1.334   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3    6                                                            
CONECT    4    1    5    6                                                  
CONECT    5    2    4                                                       
CONECT    6    3    4                                                       
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for HMDB0030061 (1,1-Dimethoxyethane)

COMPND    HMDB0030061
HETATM    1  C1  UNL     1      -1.317  -0.805   1.464  1.00  0.00           C  
HETATM    2  O1  UNL     1      -0.633   0.390   1.268  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.050   0.385   0.028  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.681   1.476  -0.846  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.327   0.520   0.053  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.987  -0.530  -0.569  1.00  0.00           C  
HETATM    7  H1  UNL     1      -2.119  -0.966   0.710  1.00  0.00           H  
HETATM    8  H2  UNL     1      -0.618  -1.679   1.329  1.00  0.00           H  
HETATM    9  H3  UNL     1      -1.738  -0.893   2.486  1.00  0.00           H  
HETATM   10  H4  UNL     1      -0.269  -0.565  -0.504  1.00  0.00           H  
HETATM   11  H5  UNL     1      -1.776   1.365  -0.847  1.00  0.00           H  
HETATM   12  H6  UNL     1      -0.395   2.476  -0.537  1.00  0.00           H  
HETATM   13  H7  UNL     1      -0.351   1.222  -1.892  1.00  0.00           H  
HETATM   14  H8  UNL     1       3.076  -0.321  -0.491  1.00  0.00           H  
HETATM   15  H9  UNL     1       1.756  -0.608  -1.644  1.00  0.00           H  
HETATM   16  H10 UNL     1       1.803  -1.469  -0.007  1.00  0.00           H  
CONECT    1    2    7    8    9
CONECT    2    3
CONECT    3    4    5   10
CONECT    4   11   12   13
CONECT    5    6
CONECT    6   14   15   16
END
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SMILES for HMDB0030061 (1,1-Dimethoxyethane)

COC(C)OC
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INCHI for HMDB0030061 (1,1-Dimethoxyethane)

InChI=1S/C4H10O2/c1-4(5-2)6-3/h4H,1-3H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Dimethyl acetalMeSH
1,1'-DimethoxyetianeHMDB
1,1-Dimethoxy-ethaneHMDB
1,1-Dimethoxyethane, 9ciHMDB
3-Methyl-2,4-dioxapentaneHMDB
Acetaldehyde dimethyl acetalHMDB
Acetaldehyde methyl acetalHMDB
Acetaldehyde, dimethyl acetalHMDB
CH3CH(OCH3)2HMDB
Dimethoxy-ethaneHMDB
DimethoxyethaneHMDB
Dimethyl aldehydeHMDB
DimethylacetalHMDB
Ethylidene dimethyl etherHMDB
FEMA 3426HMDB
Methyl formylHMDB
Chemical FormulaC4H10O2
Average Molecular Weight90.121
Monoisotopic Molecular Weight90.068079564
IUPAC Name1,1-dimethoxyethane
Traditional Name1,1-dimethoxyethane
CAS Registry Number534-15-6
SMILES
COC(C)OC
InChI Identifier
InChI=1S/C4H10O2/c1-4(5-2)6-3/h4H,1-3H3
InChI KeySPEUIVXLLWOEMJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acetals. Acetals are compounds having the structure R2C(OR')2 ( R' not Hydrogen) and thus diethers of geminal diols. Originally, the term was confined to derivatives of aldehydes (one R = H), but it now applies equally to derivatives of ketones (neither R = H ). Mixed acetals have different R' groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassEthers
Direct ParentAcetals
Alternative Parents
Substituents
  • Acetal
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-113.2 °CNot Available
Boiling Point64.00 to 65.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000 mg/mL at 25 °CNot Available
LogP0.082 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility167 g/LALOGPS
logP0.26ALOGPS
logP0.42ChemAxon
logS0.27ALOGPS
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area18.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.71 m³·mol⁻¹ChemAxon
Polarizability10.03 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+118.05331661259
DarkChem[M-H]-111.73731661259
DeepCCS[M+H]+126.12230932474
DeepCCS[M-H]-123.46930932474
DeepCCS[M-2H]-159.69530932474
DeepCCS[M+Na]+134.24130932474
AllCCS[M+H]+127.732859911
AllCCS[M+H-H2O]+123.632859911
AllCCS[M+NH4]+131.732859911
AllCCS[M+Na]+132.832859911
AllCCS[M-H]-128.032859911
AllCCS[M+Na-2H]-132.932859911
AllCCS[M+HCOO]-138.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1,1-DimethoxyethaneCOC(C)OC964.6Standard polar33892256
1,1-DimethoxyethaneCOC(C)OC571.2Standard non polar33892256
1,1-DimethoxyethaneCOC(C)OC545.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 1,1-Dimethoxyethane EI-B (Non-derivatized)splash10-0a4i-9000000000-edf11ab8e0eda3949d7a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1,1-Dimethoxyethane EI-B (Non-derivatized)splash10-00pi-9000000000-f08d7649704a8ec91f922017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1,1-Dimethoxyethane EI-B (Non-derivatized)splash10-057i-9000000000-019e56cda5254c65a1622017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1,1-Dimethoxyethane EI-B (Non-derivatized)splash10-0a6r-9000000000-888c99470f47c81f0c572017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1,1-Dimethoxyethane EI-B (Non-derivatized)splash10-0a4i-9000000000-edf11ab8e0eda3949d7a2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1,1-Dimethoxyethane EI-B (Non-derivatized)splash10-00pi-9000000000-f08d7649704a8ec91f922018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1,1-Dimethoxyethane EI-B (Non-derivatized)splash10-057i-9000000000-019e56cda5254c65a1622018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1,1-Dimethoxyethane EI-B (Non-derivatized)splash10-0a6r-9000000000-888c99470f47c81f0c572018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,1-Dimethoxyethane GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6u-9000000000-3b044e6cbb8147c68b4c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,1-Dimethoxyethane GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,1-Dimethoxyethane GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1-Dimethoxyethane 10V, Positive-QTOFsplash10-0006-9000000000-a0e8c80a141449ffcb9f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1-Dimethoxyethane 20V, Positive-QTOFsplash10-0006-9000000000-5bbd415d55679125daf02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1-Dimethoxyethane 40V, Positive-QTOFsplash10-0bvj-9000000000-b5bd7e49d4c2dbc2434a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1-Dimethoxyethane 10V, Negative-QTOFsplash10-000i-9000000000-3058aea0d237635b1cb32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1-Dimethoxyethane 20V, Negative-QTOFsplash10-000i-9000000000-e1c94a4193cc865e57562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1-Dimethoxyethane 40V, Negative-QTOFsplash10-0a4i-9000000000-1f55d3a42e00b22099932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1-Dimethoxyethane 10V, Positive-QTOFsplash10-0a4i-9000000000-340480b68bb2f63278be2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1-Dimethoxyethane 20V, Positive-QTOFsplash10-0a4i-9000000000-ef10a134ffbf21cf722e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1-Dimethoxyethane 40V, Positive-QTOFsplash10-0a4i-9000000000-ac4263738ba2495e24a22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1-Dimethoxyethane 10V, Negative-QTOFsplash10-0a4i-9000000000-bee1fb38becf8cb2b6502021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1-Dimethoxyethane 20V, Negative-QTOFsplash10-0a4i-9000000000-f43dd22bdc416949b1e92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1-Dimethoxyethane 40V, Negative-QTOFsplash10-0006-9000000000-e7e060eccffcac225ca82021-09-23Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001369
KNApSAcK IDC00053103
Chemspider ID13854808
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10795
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1018131
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Daly SR, Bellott BJ, Nesbit MA, Girolami GS: Synthesis and structural diversity of barium (N,N-dimethylamino)diboranates. Inorg Chem. 2012 Jun 18;51(12):6449-59. doi: 10.1021/ic2016879. Epub 2012 Jun 5. [PubMed:22667984 ]
  2. Dong Q, Zhao Y, Su Y, Su JH, Wu B, Yang XJ: Synthesis and reactivity of nickel hydride complexes of an alpha-diimine ligand. Inorg Chem. 2012 Dec 17;51(24):13162-70. doi: 10.1021/ic301392p. Epub 2012 Oct 15. [PubMed:23066635 ]
  3. Travia NE, Monreal MJ, Scott BL, Kiplinger JL: Thorium-mediated ring-opening of tetrahydrofuran and the development of a new thorium starting material: preparation and chemistry of ThI4(DME)2. Dalton Trans. 2012 Dec 28;41(48):14514-23. doi: 10.1039/c2dt31676e. [PubMed:23027565 ]
  4. Arii H, Matsuo M, Nakadate F, Mochida K, Kawashima T: Coordination of a chiral tin(II) cation bearing a bis(oxazoline) ligand with tetrahydrofuran derivatives. Dalton Trans. 2012 Aug 28;41(36):11195-200. doi: 10.1039/c2dt31187a. [PubMed:22875148 ]
  5. Su Y, Zhao Y, Gao J, Dong Q, Wu B, Yang XJ: Alkali metal and zinc complexes of a bridging 2,5-diamino-1,4-benzoquinonediimine ligand. Inorg Chem. 2012 May 21;51(10):5889-96. doi: 10.1021/ic3004867. Epub 2012 May 9. [PubMed:22571509 ]
  6. Li W, Xue M, Tu J, Zhang Y, Shen Q: Syntheses and structures of lanthanide borohydrides supported by a bridged bis(amidinate) ligand and their high activity for controlled polymerization of epsilon-caprolactone, L-lactide and rac-lactide. Dalton Trans. 2012 Jun 28;41(24):7258-65. doi: 10.1039/c2dt30096f. Epub 2012 May 10. [PubMed:22572741 ]
  7. Migliorini A, Oliviero C, Gasperi T, Loreto MA: The Suzuki reaction applied to the synthesis of novel pyrrolyl and thiophenyl indazoles. Molecules. 2012 Apr 16;17(4):4508-21. doi: 10.3390/molecules17044508. [PubMed:22508331 ]
  8. Mohtadi R, Matsui M, Arthur TS, Hwang SJ: Magnesium borohydride: from hydrogen storage to magnesium battery. Angew Chem Int Ed Engl. 2012 Sep 24;51(39):9780-3. doi: 10.1002/anie.201204913. Epub 2012 Aug 21. [PubMed:22907926 ]
  9. Kosog B, Kefalidis CE, Heinemann FW, Maron L, Meyer K: Uranium(III)-mediated C-C-coupling of terminal alkynes: formation of dinuclear uranium(IV) vinyl complexes. J Am Chem Soc. 2012 Aug 1;134(30):12792-7. doi: 10.1021/ja3047393. Epub 2012 Jul 16. [PubMed:22738030 ]
  10. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .