Cas no 83540-97-0 (Diisopropyl (r)-(+)-malate)

Diisopropyl (r)-(+)-malate structure
Diisopropyl (r)-(+)-malate structure
Product Name:Diisopropyl (r)-(+)-malate
CAS No:83540-97-0
MF:C10H18O5
MW:218.246923923492
MDL:MFCD00274204
CID:720290
Update Time:2024-10-26

Diisopropyl (r)-(+)-malate Chemical and Physical Properties

Names and Identifiers

    • (R)-Diisopropyl 2-hydroxysuccinate
    • Butanedioic acid,2-hydroxy-, 1,4-bis(1-methylethyl) ester, (2R)-
    • Diisopropyl (R)-(+)-malate
    • dipropan-2-yl (2R)-2-hydroxybutanedioate
    • L-MALIC ACID DIISOPROPYL ESTER
    • Diisopropyl (R)-(+)-2-hydroxysuccinate
    • (2R)-2-Hydroxybutanedioic acid 1,4-bis(1-methylethyl) ester
    • 1,4-Bis(1-methylethyl) (2R)-2-hydroxybutanedioate (ACI)
    • Butanedioic acid, hydroxy-, bis(1-methylethyl) ester, (2R)- (9CI)
    • Butanedioic acid, hydroxy-, bis(1-methylethyl) ester, (R)- (ZCI)
    • (2R)-Diisopropyl 2-hydroxybutanedioate
    • 1,4-Bis(propan-2-yl) (2R)-2-hydroxybutanedioate
    • Diisopropyl D-malate
    • Diisopropyl (r)-(+)-malate
    • MDL： MFCD00274204
    • Inchi： 1S/C10H18O5/c1-6(2)14-9(12)5-8(11)10(13)15-7(3)4/h6-8,11H,5H2,1-4H3/t8-/m1/s1
    • InChI Key： XYVHRFVONMVDGK-MRVPVSSYSA-N
    • SMILES： C(C(=O)OC(C)C)[C@@H](O)C(=O)OC(C)C

Computed Properties

  • Exact Mass: 218.11500
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 7
  • Complexity: 222
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: 0.9

Experimental Properties

  • Color/Form: Not determined
  • Density: 1.095
  • Boiling Point: 301 oC
  • Flash Point: 108 oC
  • Refractive Index: n20/D 1.43(lit.)
  • PSA: 72.83000
  • LogP: 0.64060
  • Solubility: Not determined

Diisopropyl (r)-(+)-malate Security Information

  • WGK Germany：3
  • Hazard Category Code： 36/37/38
  • Safety Instruction： S26; S36
  • Hazardous Material Identification： Xi
  • Risk Phrases：R36/37/38

Diisopropyl (r)-(+)-malate Customs Data

  • HS CODE：2918199090
  • Customs Data：

    China Customs Code:

    2918199090

    Overview:

    HS: 2918199090. Other alcohol containing but not other oxy carboxylic acids(Including its anhydride\Acyl halide\Peroxides, peroxyacids and derivatives of this tax number). VAT:17.0%. Tax refund rate:9.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2918199090 other carboxylic acids with alcohol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives.Supervision conditions:None.VAT:17.0%.Tax rebate rate:9.0%.MFN tariff:6.5%.General tariff:30.0%

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Diisopropyl (r)-(+)-malate Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Ethylene glycol ,  Samarium iodide (SmI2) Solvents: Tetrahydrofuran
Reference
Reductions with samarium(II) iodide
Molander, Gary A., Organic Reactions (Hoboken, 1994, 46,

Production Method 2

Reaction Conditions
1.1 Reagents: Thionyl chloride Solvents: Dimethylformamide
1.2 Reagents: Lithium bromide Solvents: Acetone
1.3 Reagents: Magnesium oxide ,  Hydrogen Catalysts: Palladium Solvents: Water
Reference
Process for the stereoselective transformation of a diol to an alcohol
, European Patent Organization, , ,

Production Method 3

Reaction Conditions
1.1 Reagents: Samarium iodide (SmI2) Solvents: Ethylene glycol
Reference
Preparation of D-malic acid esters by treatment of L-tartrate esters with samarium iodide.
, Japan, , ,

Production Method 4

Reaction Conditions
1.1 Solvents: Acetonitrile
Reference
Synthesis of unnatural (R)-malates from L-tartrates
Rho, Ho-Sik, Synthetic Communications, 1998, 28(5), 843-847

Production Method 5

Reaction Conditions
1.1 Reagents: Chlorotrimethylsilane Solvents: Isopropanol ;  45 h, 80 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water
Reference
Preparation of enantiopure butane-2,3-diacetals of glycolic acid and alkylation reactions leading to α-hydroxy acid and amide derivatives
Ley, Steven V.; et al, Organic & Biomolecular Chemistry, 2004, 2(24), 3608-3617

Production Method 6

Reaction Conditions
1.1 Reagents: Chlorotrimethylsilane Solvents: Isopropanol
Reference
Butane-2,3-diacetal-desymmetrized glycolic acid-a new building block for the stereoselective synthesis of enantiopure α-hydroxy acids
Diez, Elena; et al, Angewandte Chemie, 2001, 40(15), 2906-2909

Production Method 7

Reaction Conditions
1.1 Reagents: Sodium cyanoborohydride Solvents: Tetrahydrofuran
1.2 Reagents: Sulfuric acid (cyclic glycol esters) Solvents: Diethyl ether ,  Water
Reference
Vicinal diol cyclic sulfates. Like epoxides only more reactive
Gao, Yun; et al, Journal of the American Chemical Society, 1988, 110(22), 7538-9

Production Method 8

Reaction Conditions
1.1 Reagents: Lithium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  -78 °C; 15 min, -78 °C
1.2 1 h, -78 °C; -78 °C → -30 °C
1.3 Reagents: Acetic acid Solvents: Water ;  -30 °C
2.1 Reagents: Chlorotrimethylsilane Solvents: Isopropanol ;  45 h, 80 °C
2.2 Reagents: Sodium bicarbonate Solvents: Water
Reference
Preparation of enantiopure butane-2,3-diacetals of glycolic acid and alkylation reactions leading to α-hydroxy acid and amide derivatives
Ley, Steven V.; et al, Organic & Biomolecular Chemistry, 2004, 2(24), 3608-3617

Production Method 9

Reaction Conditions
1.1 Reagents: Potassium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran
2.1 Reagents: Ozone Solvents: Dichloromethane
2.2 Reagents: Triphenylphosphine
3.1 Reagents: Lithium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran
3.2 -
3.3 Reagents: Acetic acid
4.1 Reagents: Chlorotrimethylsilane Solvents: Isopropanol
Reference
Butane-2,3-diacetal-desymmetrized glycolic acid-a new building block for the stereoselective synthesis of enantiopure α-hydroxy acids
Diez, Elena; et al, Angewandte Chemie, 2001, 40(15), 2906-2909

Production Method 10

Reaction Conditions
1.1 Catalysts: Camphorsulfonic acid Solvents: Methanol
2.1 Reagents: Potassium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran
3.1 Reagents: Ozone Solvents: Dichloromethane
3.2 Reagents: Triphenylphosphine
4.1 Reagents: Lithium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran
4.2 -
4.3 Reagents: Acetic acid
5.1 Reagents: Chlorotrimethylsilane Solvents: Isopropanol
Reference
Butane-2,3-diacetal-desymmetrized glycolic acid-a new building block for the stereoselective synthesis of enantiopure α-hydroxy acids
Diez, Elena; et al, Angewandte Chemie, 2001, 40(15), 2906-2909

Production Method 11

Reaction Conditions
1.1 Reagents: Zinc ,  Methanesulfonic acid, compd. with pyridine (1:1) Catalysts: 2975587-73-4 Solvents: 1,2-Dimethoxyethane ;  1 h, rt
1.2 Reagents: Tributylstannane ;  15 min, rt; 72 h, -10 °C
1.3 Reagents: Sodium bicarbonate Solvents: Water
Reference
A Nuclearity-Dependent Enantiodivergent Epoxide Opening via Enthalpy-Controlled Mononuclear and Entropy-Controlled Dinuclear (Salen)Titanium Catalysis
Li, Shengxiao; et al, Angewandte Chemie, 2023, 62(37),

Production Method 12

Reaction Conditions
1.1 Reagents: Ethylene glycol ,  Hexamethylphosphoramide ,  Samarium iodide (SmI2) Solvents: Tetrahydrofuran
Reference
Lanthanides in organic synthesis. 21. Highly efficient deoxygenation of α-oxygenated esters via a samarium diiodide-induced electron-transfer process
Kusuda, Kazuhiro; et al, Tetrahedron Letters, 1989, 30(22), 2945-8

Production Method 13

Reaction Conditions
1.1 Reagents: Lithium bromide Solvents: 1,2-Dimethoxyethane
1.2 Reagents: Zinc Solvents: Water
Reference
Process for the stereoselective transformation of a diol to an alcohol
, European Patent Organization, , ,

Production Method 14

Reaction Conditions
1.1 Reagents: Lithium chloride Solvents: Dimethylformamide
1.2 Solvents: Water
Reference
A practical synthesis of D-malate esters from L-tartrate esters
Gao, Yun; et al, Tetrahedron Letters, 1991, 32(27), 3155-8

Production Method 15

Reaction Conditions
Reference
Process and intermediates for chiral isopropyl 3S-amino-2R-hydroxyalkanoates from chiral malic acid
, European Patent Organization, , ,

Production Method 16

Reaction Conditions
1.1 Reagents: Lithium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran
1.2 -
1.3 Reagents: Acetic acid
2.1 Reagents: Chlorotrimethylsilane Solvents: Isopropanol
Reference
Butane-2,3-diacetal-desymmetrized glycolic acid-a new building block for the stereoselective synthesis of enantiopure α-hydroxy acids
Diez, Elena; et al, Angewandte Chemie, 2001, 40(15), 2906-2909

Production Method 17

Reaction Conditions
1.1 Catalysts: Camphorsulfonic acid Solvents: Methanol
1.2 Reagents: Potassium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran
1.3 Reagents: Ozone Solvents: Methanol ,  Dichloromethane
1.4 Reagents: Dimethyl sulfide
2.1 Reagents: Lithium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran
2.2 -
2.3 Reagents: Acetic acid
3.1 Reagents: Chlorotrimethylsilane Solvents: Isopropanol
Reference
Butane-2,3-diacetal-desymmetrized glycolic acid-a new building block for the stereoselective synthesis of enantiopure α-hydroxy acids
Diez, Elena; et al, Angewandte Chemie, 2001, 40(15), 2906-2909

Production Method 18

Reaction Conditions
1.1 Reagents: Camphorsulfonic acid Solvents: Methanol ;  2 h, reflux
1.2 Reagents: Triethylamine ;  rt
2.1 Reagents: Potassium tert-butoxide Solvents: Tetrahydrofuran ;  80 min, reflux; cooled
3.1 Reagents: Oxygen Solvents: Acetone ,  Dichloromethane ;  5 min, -78 °C
3.2 Reagents: Ozone ;  4 h, -78 °C
3.3 Reagents: Oxygen ;  -78 °C
3.4 Reagents: Dimethyl sulfide ,  Pyridine ;  overnight, -78 °C → rt
4.1 Reagents: Lithium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  -78 °C; 15 min, -78 °C
4.2 1 h, -78 °C; -78 °C → -30 °C
4.3 Reagents: Acetic acid Solvents: Water ;  -30 °C
5.1 Reagents: Chlorotrimethylsilane Solvents: Isopropanol ;  45 h, 80 °C
5.2 Reagents: Sodium bicarbonate Solvents: Water
Reference
Preparation of enantiopure butane-2,3-diacetals of glycolic acid and alkylation reactions leading to α-hydroxy acid and amide derivatives
Ley, Steven V.; et al, Organic & Biomolecular Chemistry, 2004, 2(24), 3608-3617

Production Method 19

Reaction Conditions
1.1 Reagents: Oxygen Solvents: Acetone ,  Dichloromethane ;  5 min, -78 °C
1.2 Reagents: Ozone ;  4 h, -78 °C
1.3 Reagents: Oxygen ;  -78 °C
1.4 Reagents: Dimethyl sulfide ,  Pyridine ;  overnight, -78 °C → rt
2.1 Reagents: Lithium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  -78 °C; 15 min, -78 °C
2.2 1 h, -78 °C; -78 °C → -30 °C
2.3 Reagents: Acetic acid Solvents: Water ;  -30 °C
3.1 Reagents: Chlorotrimethylsilane Solvents: Isopropanol ;  45 h, 80 °C
3.2 Reagents: Sodium bicarbonate Solvents: Water
Reference
Preparation of enantiopure butane-2,3-diacetals of glycolic acid and alkylation reactions leading to α-hydroxy acid and amide derivatives
Ley, Steven V.; et al, Organic & Biomolecular Chemistry, 2004, 2(24), 3608-3617

Production Method 20

Reaction Conditions
1.1 Reagents: Ozone Solvents: Dichloromethane
1.2 Reagents: Triphenylphosphine
2.1 Reagents: Lithium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran
2.2 -
2.3 Reagents: Acetic acid
3.1 Reagents: Chlorotrimethylsilane Solvents: Isopropanol
Reference
Butane-2,3-diacetal-desymmetrized glycolic acid-a new building block for the stereoselective synthesis of enantiopure α-hydroxy acids
Diez, Elena; et al, Angewandte Chemie, 2001, 40(15), 2906-2909

Production Method 21

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide Solvents: Tetrahydrofuran ;  80 min, reflux; cooled
2.1 Reagents: Oxygen Solvents: Acetone ,  Dichloromethane ;  5 min, -78 °C
2.2 Reagents: Ozone ;  4 h, -78 °C
2.3 Reagents: Oxygen ;  -78 °C
2.4 Reagents: Dimethyl sulfide ,  Pyridine ;  overnight, -78 °C → rt
3.1 Reagents: Lithium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  -78 °C; 15 min, -78 °C
3.2 1 h, -78 °C; -78 °C → -30 °C
3.3 Reagents: Acetic acid Solvents: Water ;  -30 °C
4.1 Reagents: Chlorotrimethylsilane Solvents: Isopropanol ;  45 h, 80 °C
4.2 Reagents: Sodium bicarbonate Solvents: Water
Reference
Preparation of enantiopure butane-2,3-diacetals of glycolic acid and alkylation reactions leading to α-hydroxy acid and amide derivatives
Ley, Steven V.; et al, Organic & Biomolecular Chemistry, 2004, 2(24), 3608-3617

Production Method 22

Reaction Conditions
1.1 Reagents: Potassium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  0 °C; 30 min, 0 °C → rt; 12 h, rt
2.1 Reagents: Oxygen Solvents: Acetone ,  Dichloromethane ;  5 min, -78 °C
2.2 Reagents: Ozone ;  4 h, -78 °C
2.3 Reagents: Oxygen ;  -78 °C
2.4 Reagents: Dimethyl sulfide ,  Pyridine ;  overnight, -78 °C → rt
3.1 Reagents: Lithium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  -78 °C; 15 min, -78 °C
3.2 1 h, -78 °C; -78 °C → -30 °C
3.3 Reagents: Acetic acid Solvents: Water ;  -30 °C
4.1 Reagents: Chlorotrimethylsilane Solvents: Isopropanol ;  45 h, 80 °C
4.2 Reagents: Sodium bicarbonate Solvents: Water
Reference
Preparation of enantiopure butane-2,3-diacetals of glycolic acid and alkylation reactions leading to α-hydroxy acid and amide derivatives
Ley, Steven V.; et al, Organic & Biomolecular Chemistry, 2004, 2(24), 3608-3617

Production Method 23

Reaction Conditions
1.1 Reagents: Camphorsulfonic acid Solvents: Methanol ;  2 h, reflux
1.2 Reagents: Triethylamine ;  rt
2.1 Reagents: Potassium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  0 °C; 30 min, 0 °C → rt; 12 h, rt
3.1 Reagents: Oxygen Solvents: Acetone ,  Dichloromethane ;  5 min, -78 °C
3.2 Reagents: Ozone ;  4 h, -78 °C
3.3 Reagents: Oxygen ;  -78 °C
3.4 Reagents: Dimethyl sulfide ,  Pyridine ;  overnight, -78 °C → rt
4.1 Reagents: Lithium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  -78 °C; 15 min, -78 °C
4.2 1 h, -78 °C; -78 °C → -30 °C
4.3 Reagents: Acetic acid Solvents: Water ;  -30 °C
5.1 Reagents: Chlorotrimethylsilane Solvents: Isopropanol ;  45 h, 80 °C
5.2 Reagents: Sodium bicarbonate Solvents: Water
Reference
Preparation of enantiopure butane-2,3-diacetals of glycolic acid and alkylation reactions leading to α-hydroxy acid and amide derivatives
Ley, Steven V.; et al, Organic & Biomolecular Chemistry, 2004, 2(24), 3608-3617

Production Method 24

Reaction Conditions
1.1 Reagents: Phosphorus pentachloride Solvents: Dichloromethane ;  0 °C; 3 h, rt; rt → -20 °C
1.2 Reagents: Pyridine Solvents: Dichloromethane ;  -20 °C; 5 min, -20 °C; 15 min, -20 °C
2.1 Reagents: Zinc ,  Methanesulfonic acid, compd. with pyridine (1:1) Catalysts: 2975587-73-4 Solvents: 1,2-Dimethoxyethane ;  1 h, rt
2.2 Reagents: Tributylstannane ;  15 min, rt; 72 h, -10 °C
2.3 Reagents: Sodium bicarbonate Solvents: Water
Reference
A Nuclearity-Dependent Enantiodivergent Epoxide Opening via Enthalpy-Controlled Mononuclear and Entropy-Controlled Dinuclear (Salen)Titanium Catalysis
Li, Shengxiao; et al, Angewandte Chemie, 2023, 62(37),

Diisopropyl (r)-(+)-malate Raw materials

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Amadis Chemical Company Limited
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(CAS:83540-97-0)Diisopropyl (r)-(+)-malate
Order Number:A864253
Stock Status:in Stock
Quantity:100g
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 08:45
Price ($):305.0

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Amadis Chemical Company Limited
(CAS:83540-97-0)Diisopropyl (r)-(+)-malate
A864253
Purity:99%
Quantity:100g
Price ($):305.0
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