CAS 492-88-6 O-Ethylvanillin (HCID 68117)

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Basic information

CAS: 492-88-6
Standard SMILES: CCOc1cccc(C=O)c1O
InChIKey: OFQBYHLLIJGMNP-UHFFFAOYSA-N
Molecular formula: C9H10O3
Average molar mass: 166.17 g/mol
Monoisotopic mass: 166.06299418

Names & identifiers

Preferred name: O-Ethylvanillin
IUPAC: 3-ethoxy-2-hydroxybenzaldehyde
English name: 3-Ethoxysalicylaldehyde
Molecular formula: C9H10O3
Molecular weight: 166.17

Names & synonyms

3-Ethoxysalicylaldehyde3-Ethoxy-2-hydroxybenzaldehyde492-88-6O-EthylvanillinBenzaldehyde, 3-ethoxy-2-hydroxy-NovovanillinSalicylaldehyde, 3-ethoxy-2-Hydroxy-3-ethoxybenzaldehydeEINECS 207-765-1NSC 133446BRN 2048368ETHYLVANILLIN, O-

Show more names

Ethoxysalicylaldehyde3-EthoxysaLo-EthylvanillineAKOS BBS-00003146TIMTEC-BB SBB008590ORTHO-ETHYLVANILLIN

HB4H48MKNI2-ETHOXY-6-FORMYLPHENOLDTXSID30600836-FORMYLGUETHOLAI3-081005-ETHOXY-6-HYDROXYBENZALDEHYDENSC-1334464-08-00-01748 (Beilstein Handbook Reference)

Database identifiers

CAS: 492-88-6
PubChem CID: 68117
DTXSID: DTXSID3060083
UNII: HB4H48MKNI
EC Number: 207-765-1
Nikkaji: J30.760B

Properties

Computed structural properties

XLogP: 1.7
Topological polar surface area: 46.5 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 3
Heavy atoms: 12
Formal charge: 0
Complexity: 147

Physicochemical properties

Melting point: 66 · 66-68 °C (lit.)
Boiling point: 263 · 263-264 °C (lit.)
Density: 1.1097 · 1.1097 (rough estimate)
refractive index: 1.45 · 1.4500 (estimate)
Flash point: 263 · 263-264°C
storage temp.: 2 · under inert gas (nitrogen or Argon) at 2-8°C
form: powder to crystal
pka: 8.3 · 8.30±0.10(Predicted)
color: Light yellow to Brown to Dark green
Water Solubility: Soluble in cold water. Insoluble in methanol, ethanol, acetone and acetonitrile
Sensitive: Air Sensitive
InChI: InChI=1S/C9H10O3/c1-2-12-8-5-3-4-7(6-10)9(8)11/h3-6,11H,2H2,1H3
InChIKey: OFQBYHLLIJGMNP-UHFFFAOYSA-N
SMILES: C(=O)C1=CC=CC(OCC)=C1O
CAS DataBase Reference: 492 · 492-88-6(CAS DataBase Reference)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 45 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
tsca: TSCA listed
rtecs: CU6123000
hs_code: 29124990
Toxicity: LD50 ipr-mus: 360 mg/kg COREAF 238,2576,54
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationBenzaldehyde, 3-ethoxy-2-hydroxy-: ACTIVE

Applications · 2 items

Description3-ethoxysalicylaldehyde is also known as o-ethyl vanillin. 3-ethoxysalicylaldehyde often appears as a by-product in the production process of ethyl vanillin, which gradually becomes an alternative to vanillin since it possesses a flavor and odor approximately 3 ～ 4 times as intense as vanillin. In recent years, it has been discovered that 3-ethoxysalicylaldehyde possesses potential applications in optical utilization, biology, catalysis, and corrosion inhibition. Moreover, 3-ethoxysalicyaldehyde has been applied in various medicinal applications[1].

Uses3-Ethoxysalicylaldehyde was used in the preparation of:Schiff base ligand via condensation with trans-1,2-diaminocyclohexanesubstituted salen-type Schiff base ligandsa new Schiff base, 2-ethoxy-6-[(3-methylaminopropylimino)methyl]phenol, via reaction with N-methylpropane-1,3-diamine