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o-Vanillin

o-Vanillin structure

CAS No:
148-53-8
Formula:
C8H8O3
Chemical Name:
o-Vanillin
Synonyms:
Benzaldehyde,2-hydroxy-3-methoxy-;m-Anisaldehyde,2-hydroxy-;o-Vanillin;2-Hydroxy-3-methoxybenzaldehyde;6-Formylguaiacol;3-Methoxy-2-hydroxybenzaldehyde;3-Methoxysalicylaldehyde;6-Formyl-2-methoxyphenol;2-Hydroxy-m-anisaldehyde;NC 005;2-Vanillin;NSC 2150;2-Hydroxyl-3-methoxybenzaldehyde;o-Vaniline
Categories:
Chemical Reagents > Organic Reagents

Description

Pale yellow to brown low melting solidChEBI: A member of the class of benzaldehydes that is salicylaldehyde substituted by a methoxy group at position 3.

DryPowder

Ortho-vanillin is a member of the class of benzaldehydes that is salicylaldehyde substituted by a methoxy group at position 3. It has a role as an antimutagen and a plant metabolite. It is a member of benzaldehydes and a member of guaiacols. It derives from a salicylaldehyde.

o-Vanillin Basic Attributes

Molecular Weight：

152.15

Exact Mass：

152.15

BRN：

471913

EC Number：

205-715-3

UNII：

008LR748FI

NSC Number：

2150

DSSTox ID：

DTXSID5022011

HScode：

29124900

Characteristics

PSA：

46.5

XLogP3：

1.4

Appearance：

Pale yellow to brown Low Melting Solid

Density：

1.2065 g/cm³ @ Temp: 50.6 °C

Melting Point：

44.5 °C

Boiling Point：

265.5 °C

Flash Point：

>230 °F

Refractive Index：

1.4945 (estimate)

Water Solubility：

slightly soluble

Storage Conditions：

Store below +30°C.

Vapor Pressure：

0.00556mmHg at 25°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

22-36/37/38

safety instructions：

23-36-24/25-36/37/39-27-26

RTECS Number：

CU6530000

Marks：

Xn,Xi

Stability/Shelf Life：

Stable at room temperature in closed containers under normal storage and handling conditions.

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H302-H315-H319-H335

Drug Information

MeSH Entry Terms：

2-hydroxy-3-methoxybenzaldehyde

o-Vanillin Use and Manufacturing

Methods of Manufacturing

General procedure: To a solution of 3-methoxy-2-(trimethylsilyl)phenyl triflate 1 (53 μL, 0.20 mmol) and 1-formylpiperidine 4, N, N-dibenzylformamide 6, or N-methylformamide 8 (2.0 mmol) in CHGeneral procedure: Anhydrous potassium carbonate (2 g) and ethyl iodide (0.5 ml) were added to 2, 4-dihydroxy benzaldehyde (0.7 g, 5 mmol) acetone (30 ml) and the contents stirred for 12 h at room temperature. After the completion of the reaction as indicated by TLC, the mixture concentrated in vacuo and re-dissolved in benzene (3 × 10 ml). The organic layer concentrated and the residue chromatography on silica gel (60–120 mesh) using n-hexane: ethyl acetate mixture (46:4) as eluent to give JA-2 a crystallized solid (0.75 g, 45percent) 2.2.1.7 To an aqueous solution of NaOH (20 wtpercent, 20 mL) wereadded guaiacol (5 mmol, 0.62 g) and zeolite (5 g) under N2atmosphere at room temperature. Then chloroform(20 mL) was dropped to the mixture. Dodecane (1 mmol, 0.224 mL) was added as GC internal standard. The reactionmixture was stirred at room temperature for 24 h. Thereaction was quenched with 3 N aqueous HCl. The mixturewas extracted with ethyl acetate. The yield and selectivityof products was detected by GC.To a solution of TBAF, CsF, TBAHFGeneral procedure: To a solution of 3-methoxy-2-(trimethylsilyl)phenyl triflate 1 (53 μL, 0.20 mmol) and 1-formylpiperidine 4, N, N-dibenzylformamide 6, or N-methylformamide 8 (2.0 mmol) in CHGeneral procedure: To a solution of 3-methoxy-2-(trimethylsilyl)phenyl triflate 1 (53 μL, 0.20 mmol) and 1-formylpiperidine 4, N, N-dibenzylformamide 6, or N-methylformamide 8 (2.0 mmol) in CHGeneral procedure: To a solution of substrates (1a–1q, 0.15 mmol) in trifluoroacetic acid (5 ml), hexamethylenetetramine (0.3 mmol) and cuprous oxide (0.15 mmol) were added. The reaction mixture was refluxed for about 5 h, cooled to room temperature, followed by addition of hydrochloric acid (3 N, 5 ml). After stirring for another 1 h, the solution was concentrated under reduced pressure. The products were purified by silica gel column chromatography (200–300 mesh).

Uses

A positional isomer of Vanillin. o-Vanillin is a more potent antioxidant than Vanillin.

Intermediates

Manufacturing Info：

All other basic organic chemical manufacturing|Benzaldehyde, 2-hydroxy-3-methoxy-: ACTIVE

Computed Properties

Molecular Weight:152.15
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:152.047344113
Monoisotopic Mass:152.047344113
Topological Polar Surface Area:46.5
Heavy Atom Count:11
Complexity:135
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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