Methyl (4S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

HCID 853165CAS 60456-21-5

Substructure search Find similar structures

Basic information

Standard SMILES: COC(=O)[C@@H]1COC(C)(C)O1
InChIKey: DOWWCCDWPKGNGX-YFKPBYRVSA-N
Molecular formula: C7H12O4
Average molar mass: 160.17 g/mol
Monoisotopic mass: 160.07355886

Names & identifiers

Preferred name: Methyl (4S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate
IUPAC: methyl (4S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate
English name: alpha,beta-Isopropylidene-L-glyceric acid methyl ester
Molecular formula: C7H12O4
Molecular weight: 160.17

Names & synonyms

methyl (4S)-2,2-dimethyl-1,3-dioxolane-4-carboxylateMethyl (S)-(-)-2,2-dimethyl-1,3-dioxolane-4-carboxylateRefChem:812367611-975-260456-21-5(S)-methyl 2,2-dimethyl-1,3-dioxolane-4-carboxylateMFCD00066526alpha,beta-Isopropylidene-L-glyceric acid methyl esterMethyl 2,3-O-isopropylidene-L-glycerateMethyl (S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate(-)-Methyl (S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate(S)-Methyl 2,2-dimethyl-[1,3]dioxolane-4-carboxylate

Show more names

L-(S)-Glyceraldehyde acetonide3-PHENYLPYRAZIN-2-...METHYL ALPHA, BETA-ISOPROPYLIDENE-L-GLYCERATEα,β-isopropylidene-l-glyceric acid methyl ester2-O,3-O-Isopropylidene-L-glyceric acid methyl ester(-)-Methyl S-2,2-dimethyl-1,3-dioxolane-4-carboxylateMETHYL (S)-(-)2,2-DIMETHYL-1,3-DIOXOLANE-4-CARBOXYLATE

Methyl |A,|A-isopropylidene-L-glycerate1,3-Dioxolane-4-carboxylic acid, 2,2-dimethyl-, methyl ester, (4S)-|A,|A-Isopropylidene-L-glyceric acid methyl esterSCHEMBL1487144DOWWCCDWPKGNGX-YFKPBYRVSA-DTXSID40357404AKOS016842449CS-W008410

Database identifiers

CAS: 60456-21-5
PubChem CID: 853165
DTXSID: DTXSID40357404
EC Number: 611-975-2
Nikkaji: J236.251A

Properties

Computed structural properties

XLogP: 0.4
Topological polar surface area: 44.8 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 2
Heavy atoms: 11
Formal charge: 0
Complexity: 164

Physicochemical properties

Boiling point: 84 · 84-86 °C/15 mmHg (lit.)
Density: 1.106 g/mL · 1.106 g/mL at 25 °C (lit.)
refractive index: 20 · n20/D 1.425(lit.)
Flash point: 78 °C · 78°C
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
form: liquid
color: Pale yellow
optical activity: 20 · [α]20/D 8.5°, c = 1.5 in acetone
BRN: 4292352 · 4292352
InChI: InChI=1S/C7H12O4/c1-7(2)10-4-5(11-7)6(8)9-3/h5H,4H2,1-3H3/t5-/m0/s1
InChIKey: DOWWCCDWPKGNGX-YFKPBYRVSA-N
SMILES: O1C[C@@H](C(OC)=O)OC1(C)C
UNSPSC Code: 12352005 · 12352005
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338
PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Safety Statements: 23 · 23-24/25
WGK Germany: 3 · 3
F: 10 · 10-23
HS Code: 2932990090 · 2932990090
Storage Class: 10 · 10 - Combustible liquids

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.

Warning

H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (50%)

Safety data

F: 10-23
PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
hs_code: 2932990090
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 23-24/25
Storage Class: 10 - Combustible liquids
Hazard statements: H315-H319-H335
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Applications · 1 item

Uses()-Methyl (S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate can be used:As a chiral building block to make the key tetrahydrofuran subunit of ()-gymnodimine, a marine algal toxin.To prepare an enedione by reacting with dimethyl methylphosphonate, BuLi, and phenylglyoxal, which in turn is used to synthesize cyclopentenone derivatives.As a starting material for the preparation of (S)-4,5-dihydroxy-2,3-pentanedione (DPD), a precursor for autoinducer (AI)-2 in bacteria.