4-Hydroxybenzaldehyd

Bezeichnung:4-Hydroxybenzaldehyd

CAS-Nr123-08-0

Englisch Name:4-Hydroxybenzaldehyde

CBNumberCB6446138

SummenformelC7H6O2

Molgewicht122.12

MOL-Datei123-08-0.mol

Synonyma

4-Hydroxybenzaldehyd

4-Hydroxybenzaldehyd physikalisch-chemischer Eigenschaften

Schmelzpunkt	112-116 °C (lit.)
Siedepunkt	191°C 50mm
Dichte	1,129 g/cm³
Dampfdruck	0.004Pa at 25℃
Brechungsindex	1.5105 (estimate)
FEMA	3984 \| 4-HYDROXYBENZALDEHYDE
Flammpunkt	174°C
storage temp.	Store below +30°C.
Löslichkeit	13.8g/l
Aggregatzustand	Crystalline Powder
pka	7.61(at 25℃)
Farbe	light yellow to light brown
Geruch (Odor)	at 100.00 %. sweet nutty almond balsam woody
Geruchsart	woody
Wasserlöslichkeit	13 g/L (30 ºC)
Sensitive	Air Sensitive
JECFA Number	956
Merck	14,4811
BRN	471352
Stabilität	Hygroscopic
InChIKey	RGHHSNMVTDWUBI-UHFFFAOYSA-N
LogP	1.3 at 23℃
CAS Datenbank	123-08-0(CAS DataBase Reference)
NIST chemische Informationen	Benzaldehyde, 4-hydroxy-(123-08-0)
EPA chemische Informationen	p-Hydroxybenzaldehyde (123-08-0)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38-R36/37/38
S-Sätze:	26-36-24/25-37/39-S24/25
WGK Germany	2
RTECS-Nr.	CU6475000
Selbstentzündungstemperatur	450 °C
Hazard Note	Irritant/Air Sensitive
TSCA	Yes
HS Code	29124900
Toxizität	LD50 orally in Rabbit: 2250 mg/kg

Gefahreninformationscode (GHS)

4-Hydroxybenzaldehyde Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Aussehen Eigenschaften
C7H6O2; p-Formylphenol, p-Hydroxybenzaldehyd, p-Oxybenzaldehyd. Beiges, feinkristallines Pulver mit schwach aromatischem Geruch.
Gefahren für Mensch und Umwelt
Brennbar.
Reizt die Augen, Haut und Atmungsorgane.
Schutzmaßnahmen und Verhaltensregeln
Geeignete Schutzhandschuhe als kurzzeitiger Staubschutz.
Verhalten im Gefahrfall
Trocken aufnehmen. Der Entsorgung zuführen.
Kohlendioxid, Wasser, Pulver, Schaum.
Brennbar.
Erste Hilfe
Nach Hautkontakt: Mit reichlich Wasser abwaschen.
Nach Augenkontakt: Mit reichlich Wasser bei geöffnetem Lidspalt mindestens 10 Minuten ausspülen. Augenarzt hinzuziehen.
Nach Einatmen: Frischluft.
Nach Verschlucken: Reichlich Wasser trinken. Erbrechen auslösen. Arzt hinzuziehen.
Nach Kleidungskontakt: Kontaminierte Kleidung entfernen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Gelöst in z.B. Aceton als halogenfreie, organische Lösemittelabfälle.
Chemische Eigenschaften
4-Hydroxybenzaldehyde is a yellow to light brown crystalline powder that has a very faint, sweet-woody-balsamic odor and a sweet taste with little or no other flavor impression. The odor is also reported as vanillic/nutty.
Occurrence
It is found as a volatile in several food products, including cherries, grapes, papayas, tomatoes, cheese, beer, rum, brandy, wine, tea and peanuts. Occurs in the form of esters in several plants, notably in wintergreen leaves and the bark of sweet birch.
Verwenden
4-Hydroxybenzaldehyde maintains bactericidal activity when tested against certain bacteria strains. It also displays antioxidant potential when analyzed through assay. It is widely used starting material for polymers and pharmaceuticals.
Application
p-Hydroxybenzaldehyde is the important intermediates of pharmaceutical industry and spices. In foreign , it's also used for synthesis of bromoxynil and chloroxynil which are kind of herbicides, and also used in the manufacture of bactericide, photographic emulsifier, nickel plating luster agent, liquid crystal, etc; In the pharmaceutical field, it can be used for synthesis of amoxicillin, antibacterial synergistic agent named TMP, 3,4,5-Trimethoxybenzaldehyde，Artificial gastrodia elata, farrerol, esmololhydrochloride; In the spicery field, it can be used for synthesis of spicery,for example: vanillin, ethyl vanillin, piperonal, springaldehyde, p-anisaldehyde, raspberry ketone natural,etc.
Definition
ChEBI: 4-hydroxybenzaldehyde is a hydroxybenzaldehyde that is benzaldehyde substituted with a hydroxy group at position C-4. It has a role as a plant metabolite, a mouse metabolite and an EC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor.
synthetische
p-Hydroxybenzaldehyde is prepared by heating sodium phenolate with carbon dioxide under pressure.
Synthesis Reference(s)
Synthetic Communications, 9, p. 407, 1979 DOI: 10.1080/00397917908064169
Allgemeine Beschreibung
4-hydroxybenzaldehyde occurs naturally in vanilla beans and is one of the keys contributors to the vanilla flavor.
Synthese
2,3-Dichloro-5,6-dicyano-p-benzoquinone (DDQ 908 mg, 4 mmol) was added to a solution of 4-hydroxybenzyl alcohol (496 mg, 4 mmol) in dioxane (24 mL). The reaction mixture immediately turned deep green (exothermic reaction), and DDQH2 started precipitating within 1 min. Thin layer chromatography (TLC) analysis indicated consumption of starting material after 15 min. The solvent was removed from the yellow reaction mixture in vacuo. Treatment of the residue with CH2Cl2 left DDQH2 undissolved (quantitatively). Filtration followed by evaporation of CH2Cl2 gave 4-hydroxybenzaldehyde (74% yield) which was recrystallized from water.

Reference: Becker, H.-D.; Bjork, A.; Alder, E. J. Org. Chem. 1980, 45, 1596?1600.
target
GABA Receptor
läuterung methode
Crystallise it from water (containing some H2SO4). Dry it over P2O5 under vacuum. [Beilstein 8 H 64, 8 IV 251.]
Einzelnachweise
[1] HANS DIETER BECKER Erich A Anders Bjoerk. Quinone dehydrogenation. Oxidation of benzylic alcohols with 2,3-dichloro-5,6-dicyanobenzoquinone[J]. The Journal of Organic Chemistry, 1980, 45 9: 1596-1600. DOI:10.1021/jo01297a010.
[2] CHAN WOO KANG. 4-Hydroxybenzaldehyde accelerates acute wound healing through activation of focal adhesion signalling in keratinocytes.[J]. Scientific Reports, 2017: 14192. DOI:10.1038/s41598-017-14368-y.
[3] M. EDDOUKS. Insulin Resistance as a Target of Some Plant-Derived Phytocompounds[J]. Studies in natural products chemistry, 1900, 26 1: 351-373. DOI:10.1016/B978-0-444-63430-6.00011-4.
[4] DOUGLASS F. TABER. Vanillin Synthesis from 4-Hydroxybenzaldehyde[J]. Journal of Chemical Education, 2007, 84 7: 1158. DOI:10.1021/ed084p1158.
[5] MAKOTO KOMIYAMA Hidefumi H. Selective synthesis of 4-hydroxybenzaldehyde with cyclodextrin as catalyst[J]. Macromolecular Rapid Communications, 1981, 2 12: 715-717. DOI:10.1002/marc.1981.030021202.
[6] HIROAKI MATSUDA . Mutagenicity of ozonation and chlorination products from p-hydroxybenzaldehyde[J]. Science of the Total Environment, 1991, 103 2: Pages 141-149. DOI:10.1016/0048-9697(91)90140-A.

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