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144088

Sigma-Aldrich

4-Hydroxybenzaldehyde

98%

Synonym(s):

4-Formylphenol, 4-Hydroxybenzaldehyde, Parahydroxybenzaldehyde, p-Formylphenol, p-Hydroxybenzaldehyde, p-Oxybenzaldehyde

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R$366.00
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R$366.00
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About This Item

Linear Formula:
HOC6H4CHO
CAS Number:
123-08-0
Molecular Weight:
122.12
Beilstein:
471352
EC Number:
204-599-1
MDL number:
MFCD00006939
UNSPSC Code:
12352100
PubChem Substance ID:
24848630
NACRES:
NA.22
form:
solid
Assay:
98%

R$366.00

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Quality Level

200

Assay

98%

form

solid

mp

112-116 °C (lit.)

functional group

aldehyde

SMILES string

[H]C(=O)c1ccc(O)cc1

InChI

1S/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H

InChI key

RGHHSNMVTDWUBI-UHFFFAOYSA-N

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Application

4-Hydroxybenzaldehyde can be used as a reactant to synthesize:
  •  4-Hydroxybenzaldehydesemicarbazone by a condensation reaction with semicarbazide.    
  • Vanillin via bromination followed by copper-catalyzed coupling reaction with sodium methoxide.[1]      
  • Oligo-4-hydroxybenzaldehyde by an oxidative polycondensation reaction with hydrogen peroxide (H2O2) in an alkaline medium.[2]
  • (−)-Centrolobine, a diarylheptanoid.[3]

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H318,H335

Hazard Classifications

Eye Dam. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

345.2 °F

Flash Point(C)

174 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM7165
BCCL9006
BCCL4457
BCCG3954
BCCD1328

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Vanillin synthesis from 4-hydroxybenzaldehyde
Taber Douglass F, et al.
Journal of Chemical Education, 84(7), 1158-1158 (2007)
The synthesis, characterization and thermal stability of oligo-4-hydroxybenzaldehyde
Mart H, et al.
Polymer Degradation and Stability, 83(3), 395-398 (2004)
Stereoselective synthesis of (-)-centrolobine
Lee Eun, et al.
Bulletin of the Korean Chemical Society,, 25(11), 1609-1610 (2004)
Nadja Schultz-Jensen et al.
Applied biochemistry and biotechnology, 165(3-4), 1010-1023 (2011-07-06)
The potential of wheat straw for ethanol production after pretreatment with O(3) generated in a plasma at atmospheric pressure and room temperature followed by fermentation was investigated. We found that cellulose and hemicellulose remained unaltered after ozonisation and a subsequent
Wei Yi et al.
European journal of medicinal chemistry, 45(2), 639-646 (2009-11-26)
A series of novel 4-hydroxybenzaldehyde derivatives were synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were investigated. Most of target compounds had more potent inhibitory activities than the parent compound 4-hydroxybenzaldehyde (IC(50)=1.22 mM). Interestingly, compound 3c
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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