ChemicalBook > CAS DataBase List > Salicylaldehyde

Salicylaldehyde

Product Name
Salicylaldehyde
CAS No.
90-02-8
Chemical Name
Salicylaldehyde
Synonyms
2-HYDROXYBENZALDEHYDE;SALICYLIC ALDEHYDE;salicyladehyde;salicyaldehyde;O-HYDROXYBENZALDEHYDE;SALICYLALDEHYD;Benzaldehyde,2-hydroxy-;Benzaldehyde, o-hydroxy-;Salicylaldehyde, 99% 100GR;Salicylal
CBNumber
CB6127950
Molecular Formula
C7H6O2
Formula Weight
122.12
MOL File
90-02-8.mol
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Salicylaldehyde Property

Melting point:
1-2 °C (lit.)
Boiling point:
197 °C (lit.)
Density 
1.146 g/mL at 25 °C (lit.)
vapor density 
4.2 (vs air)
vapor pressure 
1 mm Hg ( 33 °C)
refractive index 
n20/D 1.573(lit.)
FEMA 
3004 | SALICYLALDEHYDE
Flash point:
170 °F
storage temp. 
-20°C
solubility 
4.9g/l
form 
Liquid
pka
8.37(at 25℃)
color 
Clear yellow
PH
6-8 (H2O, 20℃)Not applicable
Odor
Bitter almonds
Odor Type
medicinal
Water Solubility 
slightly soluble
Sensitive 
Air & Light Sensitive
Merck 
14,8326
JECFA Number
897
BRN 
471388
Dielectric constant
17.100000000000001
Dielectric constant
13.9（20℃）
Exposure limits
ACGIH: TWA 5 ppm (Skin)
OSHA: TWA 5 ppm(19 mg/m3)
NIOSH: IDLH 250 ppm; TWA 5 ppm(19 mg/m3); Ceiling 15.6 ppm(60 mg/m3)
Stability:
Stable. Combustible. Incompatible with strong bases, strong reducing agents, strong acids, strong oxidizing agents.
InChIKey
SMQUZDBALVYZAC-UHFFFAOYSA-N
LogP
1.66 at 25℃ and pH6.2-6.3
CAS DataBase Reference
90-02-8(CAS DataBase Reference)
NIST Chemistry Reference
Benzaldehyde, 2-hydroxy-(90-02-8)
EPA Substance Registry System
Salicylaldehyde (90-02-8)
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Safety

Hazard Codes 
Xn,N
Risk Statements 
21/22-36/38-68-36/37/38-20/21/22-51-36-51/53-22
Safety Statements 
26-36/37-36/37/39-36-61-64-29/35
RIDADR 
3082
WGK Germany 
2
RTECS 
VN5250000
F 
8-10-23
TSCA 
Yes
HazardClass 
6.1(b)
PackingGroup 
II
HS Code 
29122990
Hazardous Substances Data
90-02-8(Hazardous Substances Data)
Toxicity
MLD in rats (mg/kg): 900-1000 s.c. (Binet)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H341Suspected of causing genetic defects

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P273Avoid release to the environment.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
W300403
Product name
Salicylaldehyde
Purity
≥98%, FG
Packaging
1kg
Price
$76.5
Updated
2024/03/01
Sigma-Aldrich
Product number
W300403
Product name
Salicylaldehyde
Purity
≥98%, FG
Packaging
10Kg
Price
$396
Updated
2024/03/01
Sigma-Aldrich
Product number
W300403
Product name
Salicylaldehyde
Purity
≥98%, FG
Packaging
25kg
Price
$834
Updated
2024/03/01
Sigma-Aldrich
Product number
CRM78313
Product name
Salicylaldehyde
Purity
certified reference material, TraceCERT?
Packaging
100MG
Price
$183
Updated
2024/03/01
Sigma-Aldrich
Product number
8.00640
Product name
2-Hydroxybenzaldehyde
Purity
for synthesis
Packaging
5ML
Price
$20.7
Updated
2024/03/01
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Salicylaldehyde Chemical Properties,Usage,Production

Description

Salicylaldehyde (2-hydroxybenzaldehyde) is an organic compound with the formula C6H4CHO-2-OH. Along with 3-hydroxybenzaldehyde and 4-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde. It is a colorless or pale yellow liquid with a bitter almond odor and a burning taste. It is soluble in alcohol, benzene, and ether, and very slightly soluble in water. Salicylaldehyde is found in shrubs of the genus Spiraea and is usually produced from phenol by the action of chloroform in the presence of an alkali base. It is used in the production of coumarin, saligenin, and salicylaldoxime (an important analytical reagent), and also in analytical chemistry—for example, to detect hydrazine. Besides, salicylaldehyde is a key precursor to various chelating agents and a flavouring ingredient.

Chemical Properties

Salicylaldehyde is a colourless to yellow oily liquid with a pungent, irritating, bitter, almond-like odor similar to benzaldehyde, acetophenone and nitrobenzene, but with phenolic notes. It has a nut-like, coumarin flavor at low levels. slightly soluble in water, soluble in ethanol and ether. It turns purple in case of ferric chloride.

Occurrence

Occurs frequently in nature; in the flowers of Spirea ulmaria and other Spireae, in the roots of Crepis foetida L., in the fruits of Pinus avium, in the rind of Rauqolfia caffra, in the leaves of Ceanothus velutinus and in the essential oil of Cinnamomum cassia and of tobacco leaves. Also reported found in grapes, tomato, baked potato, cinnamon bark, cassia leaf, peppermint oil, pennyroyal oil, parmesan cheese, butter, milk powder, roasted chicken, beer, rum, Japanese whiskey, sherry, coffee, tea, soybean, mushroom, buckwheat, Bourbon vanilla, Chinese quince, Muscat grape, vanilla and mastic gum oil.

Uses

Salicylaldehyde, is used as flavor and fragrance components. Salicylaldehyde is also a common highly-functionalized arene, that can be used as a precursor in the synthesis of other chemicals.

Preparation

Salicylaldehyde is synthesized from phenol, chloroform, and alkali according to the Reimer–Tiemman method, which was developed in 1876. starting material for the manufacture of coumarin.

Definition

ChEBI: Salicylaldehyde is a hydroxybenzaldehyde carrying a hydroxy substituent at position 2. It has a role as a nematicide and a plant metabolite.

Aroma threshold values

Detection: 30 ppb

Taste threshold values

Taste characteristics at 20 ppm: spicy, medicinal and astringent

Synthesis Reference(s)

Synthetic Communications, 24, p. 1757, 1994 DOI: 10.1080/00397919408010181

General Description

Liquid; colorless or pale yellow; bitter almond odor. Sinks and mixes slowly in water.

Reactivity Profile

Salicylaldehyde is an aldehyde. Aldehydes are frequently involved in self-condensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation.

Health Hazard

Salicylaldehyde is a skin irritant; 500 mg/daycaused moderate irritation to rabbit skin. Itcan have injurious effects on fertility. Studieson rats indicate that subcutaneous administrationof salicylaldehyde in a high doseof >400 mg/kg can produce developmentalabnormalities, fetal death, and postimplantationmortality.
The toxicity of this compound, however,is low. No toxic symptoms were noted.
LD50 value, oral (rats): 520 mg/kg
LD50 value, skin (rats): 600 mg/kg.

Fire Hazard

Combustible. Can react with oxidizing materials.

Purification Methods

It is precipitated as the bisulfite addition compound by pouring the aldehyde slowly and with stirring into a 25% solution of NaHSO3 in 30% EtOH, then standing for 30minutes. The precipitate, after filtering at the pump, and washing with EtOH, is decomposed with aqueous 10% NaHCO3, and the aldehyde is extracted into diethyl ether, dried with Na2SO4 or MgSO4, and distilled, under reduced pressure. Alternatively, salicylaldehyde is precipitated as its Cu complex by adding it to warm, saturated aqueous Cu(OAc)2, shaking and standing in ice. The precipitate is filtered off, washed with EtOH, then Et2O, and decomposed with 10% H2SO4; the aldehyde is extracted into Et2O, dried and vacuum distilled. It was also purified by dry column chromatography on Kieselgel G [Nishiya et al. J Am Chem Soc 108 3880 1986]. The acetyl derivative has m 38-39o (from pet ether or EtOH) and b 142o/18mm, 253o/atm. [Beilstein 8 IV 176.] The oxime, [94-67-7] M 137.1, crystallises CHCl3/pet ether (b 40-60o) with m 57o [Beilstein 8 IV 203.]

Waste Disposal

Salicylaldehyde is burned in a chemicalincinerator equipped with an afterburner andscrubber.

References

  • https://en.wikipedia.org/wiki/Salicylaldehyde
  • https://pubchem.ncbi.nlm.nih.gov/compound/salicylaldehyde#section=Top
  • http://www.wisegeek.com/what-is-salicylaldehyde.htm
  • https://www.merriam-webster.com/medical/salicylaldehyde
  • http://encyclopedia2.thefreedictionary.com/Salicylaldehyde

Salicylaldehyde Preparation Products And Raw materials

Raw materials

Salicylic acid o-Cresol Chloroform Sodium hydroxide

Preparation Products

Salicylaldoxime COUMARIN 7 2-Methylcumarone METHYL 1-BENZOFURAN-2-CARBOXYLATE 2-Ethoxybenzaldehyde L-Phenylglycine 3-METHYL-CHROMEN-2-ONE Coumarin 5-(2-ETHOXYPHENYL)-1-METHYL-3-N-PROPYL-1,6-DIHYDRO-7H-PYRAZOLO[4,3-D]-7-PYRIMIDINONE a copper chelate 1-BENZOFURAN-2-CARBOXAMIDE 3-ACETAMIDOCOUMARIN Cefixime D(-)-allo-Threonine SALITHION 2-Benzofurancarboxylic acid ethyl ester Amiodarone 1,3,3-TRIMETHYLINDOLINOBENZOPYRYLOSPIRAN 5-Chlorosalicylaldehyde Bunitrolol 4-Hydroxybenzaldehyde 2-(2-FORMYL-PHENOXY)-PROPIONIC ACID 2-[(2,6-DICHLOROBENZYL)OXY]BENZALDEHYDE BENZOFURAN-2-CARBONYL CHLORIDE 2-Benzofurancarboxaldehyde 6-Methylcoumarin Benzofuran o-Anisaldehyde 2-Cyanophenol 3-ALLYLSALICYLALDEHYDE
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View Lastest Price from Salicylaldehyde manufacturers

Ningxia Jinhua Chemical Co.,Ltd
Product
Salicylaldehyde 90-02-8
Price
US $0.00/Kg/Drum
Min. Order
100KG
Purity
≥99.5%;≥99.0%;≥95.0%
Supply Ability
10tons
Release date
2020-12-16
Changde Changlian Chemical Co., Ltd.
Product
Salicylaldehyde 90-02-8
Price
US $0.00/Kg/Drum
Min. Order
100KG
Purity
≥99.5%;≥99.0%;≥95.0%
Supply Ability
10tons
Release date
2020-12-16
Yancheng Green Chemicals Co.,Ltd
Product
Salicylaldehyde 90-02-8
Price
US $0.00/Kg/Drum
Min. Order
250KG
Purity
99.5; 99; 95
Supply Ability
10mt
Release date
2020-12-15

90-02-8, SalicylaldehydeRelated Search:

Cinnamaldehyde Cuminaldehyde Salicylic acid Paraldehyde 3-Fluoro-4-hydroxybenzaldehyde p-Anisaldehyde 2-Cyanophenol 2-Nitrobenzaldehyde SALICYLALDEHYDE OXIME 4-Dimethylaminobenzaldehyde 3,5-Dihydroxybenzaldehyde 4-Hydroxybenzaldehyde 3-(Trifluoromethyl)benzaldehyde Benzaldehyde 2-Hydroxyphenylacetic acid Ethylenediamine Diethyl malonate 3-Nitrosalicylaldehyde

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