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3-ALLYLSALICYLALDEHYDE

3-ALLYLSALICYLALDEHYDE structure

CAS No:
24019-66-7
Formula:
C10H10O2
Chemical Name:
3-ALLYLSALICYLALDEHYDE
Synonyms:
Salicylaldehyde, 3-allyl-;TIMTEC-BB SBB010096;3-ALLYL-2-HYDROXY-BENZALDEHYDE;3-ALLYL SALCYLALDEHYDE;3-ALLYLSALICYLALDEHYDE;AKOS BBS-00003205;2-HYDROXY-3-(2-PROPENYL)-BENZALDEHYDE;ASINEX-REAG BAS 02801117
Categories:
Chemical Reagents > Organic Reagents

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Description

Light Yellow Liquid

3-ALLYLSALICYLALDEHYDE Basic Attributes

Molecular Weight：

162.19

Exact Mass：

162.068085

DSSTox ID：

DTXSID80178751

HScode：

2912499000

Characteristics

PSA：

37.3

XLogP3：

2.7

Density：

1.1±0.1 g/cm3

Melting Point：

45 °C

Boiling Point：

243.2°C at 760 mmHg

Flash Point：

224 °F

Refractive Index：

1.593

Water Solubility：

soluble in chloroform.

Safety Information

Hazard category：

IRRITANT

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-36/37

Marks：

Hazard note：

Irritant

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 42 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

3-ALLYLSALICYLALDEHYDE Use and Manufacturing

Methods of Manufacturing

13.5 g 2-allylphenol (0.1 mol) and 100 mL acetonitrile were added to a three-necked bottle, to which 6.5 g paraformaldehyde, 22 g anhydrous magnesium chloride (0.39 mol) and triethylamine (0.02 mol) were added in this order with stirring at room temperature.Step G: Preparation of 3-allyl-2-hydroxy benzaldehyde 13.5 g 2-allylphenol (0.1 mol) and 100 mL acetonitrile were added to a three-necked bottle, to which 6.5 g paraformaldehyde, 22 g anhydrous magnesium chloride (0.39 mol) and triethylamine (0.02 mol) were added in this order with stirring at room temperature. After refluxing for 4 hours, the reaction solution was poured into ice water, which was adjusted with aqueous HCl solution to a pH of 5. After extraction with ethyl acetate twice, drying with anhydrous sodium sulfate and concentration under reduced pressure, 11 g solid was obtained. Yield: 68percent, MS: 163 (M+1).The o-hydroxybenzaldehyde is first reacted with 3-bromopropene.

Uses

3-Allyl Salicylaldehyde is a synthetic intermediate for the sythesis of 3-aminoflavones. Flavonoids have been studied for their antiproliferative activity and in vitro cytotoxicity. Used in the preparation of oxazole derivatives. Used in the preparation of imidazole scaffold-based 2-substituted benzofurans for application against human tumor cell lines. Also a reagent in the synthesis of antioxidant and antimicrobial novel chalcones.

Computed Properties

Molecular Weight:162.18
XLogP3:2.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:162.068079557
Monoisotopic Mass:162.068079557
Topological Polar Surface Area:37.3
Heavy Atom Count:12
Complexity:165
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Ethyl acetate

Potassium carbonate

Acetone