Dibenzyl malonate

HCID 84754

Notes Reactions

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Basic information

CAS: 15014-25-2
Standard SMILES: O=C(CC(=O)OCc1ccccc1)OCc1ccccc1
InChIKey: RYFCSKVXWRJEOB-UHFFFAOYSA-N
Molecular formula: C17H16O4
Average molar mass: 284.31 g/mol
Monoisotopic mass: 284.10485899

Names & identifiers

Preferred name: Dibenzyl malonate
IUPAC: dibenzyl propanedioate
English name: Dibenzyl malonate
Molecular formula: C17H16O4
Molecular weight: 284.31

Names & synonyms

Dibenzyl malonate15014-25-2Propanedioic acid, bis(phenylmethyl) esterNSC 101027EINECS 239-099-2DTXSID40164478RefChem:132863DTXCID6086969239-099-2InChI=1/C17H16O4/c18-16(20-12-14-7-3-1-4-8-14)11-17(19)21-13-15-9-5-2-6-10-15/h1-10H,11-13HRYFCSKVXWRJEOB-UHFFFAOYSA-Ndibenzyl propanedioate

Show more names

C17H16O4DibenzylmalonatDibenzylMalonate>D**DIBENZYL MALONATEMalonic acid dibenzyl

Malonic Acid Dibenzyl Ester1,3-dibenzyl propanedioateMFCD00004779Propanedioic acid, 1,3-bis(phenylmethyl) esterPropanedioic acid dibenzyl esterMLS002703585NSC101027;NSC-101027;Malonic acid, dibenzyl ester (6CI,8CI); Propanedioic acid, bis(phenylmethyl) ester (9CI); Dibenzyl malonateDibenzylmalonateca

Database identifiers

CAS: 15014-25-2
PubChem CID: 84754
DTXSID: DTXSID40164478
ChEMBL: CHEMBL2357598
EC Number: 239-099-2
Nikkaji: J274G

Properties

Computed structural properties

XLogP: 3.1
Topological polar surface area: 52.6 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 8
Heavy atoms: 21
Formal charge: 0
Complexity: 296

Physicochemical properties

Boiling point: 188 °C/0.2 · 188 °C/0.2 mmHg (lit.)
Density: 1.137 g/mL · 1.137 g/mL at 25 °C (lit.)
refractive index: 20 · n20/D 1.546(lit.)
Flash point: 230 °F · >230 °F
storage temp.: Sealed in dry,Room Temperature
pka: 11.65 · 11.65±0.46(Predicted)
form: clear liquid
color: Colorless to Light yellow to Light orange
Specific Gravity: 1.17 · 1.17
Water Solubility: Sparingly soluble in water; miscible in all proportions with ether and alcohol.
BRN: 1998264 · 1998264
InChI: InChI=1S/C17H16O4/c18-16(20-12-14-7-3-1-4-8-14)11-17(19)21-13-15-9-5-2-6-10-15/h1-10H,11-13H2
InChIKey: RYFCSKVXWRJEOB-UHFFFAOYSA-N
SMILES: C(OCC1=CC=CC=C1)(=O)CC(OCC1=CC=CC=C1)=O
CAS DataBase Reference: 15014 · 15014-25-2(CAS DataBase Reference)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338
PPE: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
Safety Statements: 23 · 23-24/25
WGK Germany: 3 · 3
HS Code: 29171910 · 29171910
Storage Class: 10 · 10 - Combustible liquids

Safety & regulation

Hazard information

Regulatory InformationPropanedioic acid, bis(phenylmethyl) ester: Does not have an individual approval but may be used under an appropriate group standard

Regulatory information

Regulatory InformationPropanedioic acid, bis(phenylmethyl) ester: Does not have an individual approval but may be used under an appropriate group standard

Safety data

PPE: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
wgk: 3
hs_code: 29171910
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 23-24/25
Storage Class: 10 - Combustible liquids
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Applications · 2 items

UsesDibenzyl malonate was used in the preparation of tetraethyl 3,3-bis(benzyloxycarbonyl)propylene bisphosphonate. It was also used in the preparation of benzyl umbelliferone-3-carboxylate via Knoevenagel condensation with 2,4-dihydroxybezaldehyde.

General DescriptionDirect asymmetric reaction of dibenzyl malonate with N-tert-butoxycarbonyl aldimines in the presence of Yb(OTf)3 and iPr-pybox (pybox = pyridine bisoxazoline) complexes has been investigated.