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418099

Sigma-Aldrich

Benzaldehyde

purified by redistillation, ≥99.5%

Synonym(s):

Bitter almond

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100 ML
$102.00
500 ML
$252.00

About This Item

Linear Formula:
C6H5CHO
CAS Number:
Molecular Weight:
106.12
Beilstein:
471223
EC Number:
MDL number:
UNSPSC Code:
12352100
eCl@ss:
39023701
PubChem Substance ID:
NACRES:
NA.22
bp:
178-179 °C (lit.)
vapor pressure:
4 mmHg ( 45 °C)

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vapor density

3.7 (vs air)

Quality Level

vapor pressure

4 mmHg ( 45 °C)

Assay

≥99.5%

form

liquid

autoignition temp.

374 °F

purified by

redistillation

expl. lim.

1.4 %, 20 °F

refractive index

n20/D 1.545 (lit.)

pH

5.9 (20 °C)

bp

178-179 °C (lit.)

mp

−26 °C (lit.)

density

1.044 g/cm3 at 20 °C (lit.)

functional group

aldehyde
phenyl

SMILES string

O=Cc1ccccc1

InChI

1S/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H

InChI key

HUMNYLRZRPPJDN-UHFFFAOYSA-N

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General description

Benzaldehyde (bitter-almond oil) is an aromatic compound commonly used in the cosmetics and flavor industries. The natural source of benzaldehyde is amygdalin, a glycoside found in apricots, bitter almonds, apples, cherries etc. Benzaldehyde is commercially produced by liquid phase chlorination and oxidation of toluene. Other methods reported to produce benzaldehyde include oxidation of benzyl alcohol, hydrolysis of benzal chloride and carbonylation of benzene.[1][2]

Application

Benzaldehyde can be used as a precursor to synthesize:
  • Cinnamaldehyde, cinnamic acid, ethyl cinnamate, benzoic acid, benzyl alcohol, benzyl benzoate and hydrobenzamide etc.[2]
  • Triphenylmethane derivatives by condensation with phenols, aromatic amines, and benzene. This reaction is useful for the production of malachite green dyes.[2]
  • Benzoylborane by reacting with borylmagnesium bromides.[3]
  • Multi-benzaldehyde functionalized poly(ethylene glycol) analog which is used as a cross-linker to develop an injectable hydrogel system.[4]

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Flash Point(F)

145.4 °F - closed cup

Flash Point(C)

63 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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An injectable hydrogel formed by in situ cross-linking of glycol chitosan and multi-benzaldehyde functionalized PEG analogues for cartilage tissue engineering
Cao L, et al.
Journal of materials chemistry. B, 3(7), 1268-1280 (2015)
Synthesis, structure of borylmagnesium, and its reaction with benzaldehyde to form benzoylborane
Yamashita M, et al.
Journal of the American Chemical Society, 129(31), 9570-9571 (2007)
Highly selective oxidation of benzyl alcohol to benzaldehyde catalyzed by bimetallic gold?copper catalyst
Della Pina C, et al.
J. Catal., 260(2), 384-386 (2008)
Benzaldehyde
Bruhne F and Wright E
Ullmann's Encyclopedia of Industrial Chemistry (2000)
Spacing and site isolation of amine groups in 3-aminopropyl-grafted silica materials: The role of protecting groups.
Hicks JC, et al.
Chemistry of Materials, 18(21), 5022-5032 (2006)

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  1. 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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  2. 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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