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Phloroglucinol

Feature reaction of phloroglucinol Chemical properties Uses Production method Hazards & Safety Information

Phloroglucinol

CAS No.108-73-6
Chemical Name:Phloroglucinol
CBNumber:CB0667672
Molecular Formula:C6H6O3
Formula Weight:126.11
MOL File:108-73-6.mol

Phloroglucinol Property

Melting point 215-220 °C
Boiling point 194.21°C (rough estimate)
Density 0.801 g/mL at 20 °C
bulk density 560kg/m3
vapor pressure 0.001Pa at 25℃
refractive index n20/D 1.365
Flash point 14 °C
storage temp. Store below +30°C.
solubility Soluble in diethyl ether, ethanol and pyridine.
form Crystalline Powder
pka pK1:8.45(0);pK2:8.88(-1) (25°C)
color White to light beige
Water Solubility 11.17g/L(room temperature)
Sensitive Light Sensitive & Hygroscopic
Merck 14,7328
BRN 1341907
InChIKey QCDYQQDYXPDABM-UHFFFAOYSA-N
LogP 0.55 at 25℃
CAS DataBase Reference 108-73-6(CAS DataBase Reference)
EWG's Food Scores 3-6
FDA UNII DHD7FFG6YS
ATC code A03AX12
NIST Chemistry Reference 1,3,5-Benzenetriol(108-73-6)
EPA Substance Registry System 1,3,5-Benzenetriol (108-73-6)
UNSPSC Code 41116107
NACRES SE.11

Safety

Hazard Codes :F,Xi
Risk Statements :11-36/37/38-34-43
Safety Statements :7-16-24/25-45-36/37/39-26-36/37-37/39
RIDADR :UN 1170 3/PG 2
WGK Germany :2
RTECS :SY1050000
TSCA :Yes
HS Code :29072900
Toxicity :LD50 in mice, rats (g/kg): 4.7, 4.0 i.g. (Cahen)

NFPA 704:

	0
2		1

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H315-H317-H319-H335
Precautionary statements P261-P264-P271-P280-P302+P352-P305+P351+P338

Phloroglucinol Price More Price(17)

Brand: Sigma-Aldrich(India)
Product number: P3502
Product name : Phloroglucinol
Purity: Used to detect the presence of wood fiber.
Packaging: 25G
Price: ₹3615.55
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: P3502
Product name : Phloroglucinol
Purity: Used to detect the presence of wood fiber.
Packaging: 100G
Price: ₹6007.88
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: P1178
Product name : Phloroglucinol
Purity: suitable for plant cell culture, BioReagent
Packaging: 100G
Price: ₹10933.25
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 79330
Product name : Phloroglucinol
Purity: ≥99.0% (HPLC)
Packaging: 25G
Price: ₹4578.98
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 8.18887
Product name : Phloroglucinol
Purity: for synthesis
Packaging: 100G
Price: ₹10810
Updated: 2022/06/14
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Phloroglucinol Chemical Properties,Usage,Production

Feature reaction of phloroglucinol Reaction of formaldehyde with phloroglucinol under alkaline conditions generates orange compound. The colorimetric assay determination of this compound at the maximum absorption wavelength of 460 nm, can be used to detect low or trace formaldehyde in textile and garment.
Since phloroglucinol may occur enol and keto tautomers, it can react with ammonia according following reaction:

Under the influence of ammonia, 1,3,5-Benzenetriamine can be obtained by keto reaction of phloroglucinol, while this amine can also hydrolyze in aqueous acid to generate phloroglucinol. Besides phloroglucinol can also have enol reaction.

The information above is edited by Andy from Chemicalbook.
Chemical properties This product is a white or light yellow crystal or crystalline powder with melting point of 218 ℃. Usually it carries two molecular crystallization water ([6099-90-7]) and converts into anhydrous at 110 ℃. It can be dissolved in 100 parts of water, 10 parts of ethanol, and 0.5 parts of pyridine and is soluble in ether. Besides It partially decomposes when sublimation, and changes its color when exposed to the light. In addition it tastes sweet.
Uses Phloroglucinol can be used in verifications of antimony, arsenic, cerium, chromate, chromium, gold, iron, mercury, nitrites, osmium, palladium, tin, vanadium, vanillin and lignin, and measurement of furfural, pentose, pentosan, methanol, chloral hydrate, turpentine, Lignified cell tissues, free acid in gastric juice (HCl) and decalcified bone specimens. Besides it can also be used as biological reagent dyes.
Production method 2,4,6-aminobenzoic acid can be obtained by 2,4,6-trinitrobenzoic acid`s reduction of zinc particles. After its dilute solution was heated at reflux for 20h, acidified with hydrochloric acid, cooled and crystallized, phloroglucinol can be obtained with a yield of 46-53%.
Hazards & Safety Information Category: Toxic substances
Toxicity grade: Moderate toxicity
Acute toxicity: oral-rat LD50: 4000 mg/kg; Oral-Mouse LD50: 4550 mg/kg
Flammability hazard characteristics: Combustible fire burning can cause smoke irritation
Storage characteristics: Ventilated, low-temperature and dry warehouse; and separately with oxidants
Extinguishing agents: Carbon dioxide, foam, sand and water mist
Description Phloroglucinol is a naturally occurring phenol that exhibits diverse biological activities. Phloroglucinol protects V79-4 Chinese hamster lung fibroblast cells from oxidative stress and inhibits lipid peroxidation by scavenging reactive oxygen species (ROS). It induces apoptosis in HT-29 human colon cancer cells and inhibits metastasis of BT549 and MDA-MB-231 human breast cancer cells. Phloroglucinol protects primary neurons from β-amyloid-induced dendritic spine loss in vitro and shortens the latency to find the platform in a Morris water maze test in an Alzheimer’s disease (AD) mouse model. Phloroglucinol has been used to stain histological plant sections and in the synthesis of numerous natural products. Phloroglucinol slows the frequency and decreases the amplitude of contraction in isolated rabbit and rat intestine at a concentration of 100 and 1 μM, respectively. Formulations containing phloroglucinol have been used as antispasmodics.
Chemical Properties white to light yellow crystal
Physical properties Phloroglucinol crystallizes in the anhydrous form or as the dihydrate. Recrystallization from water gives the dihydrate, which is colorless, oderless, sweet in taste, and forms rhombic crystals. The dihydrate is converted into the anhydrous form by heating at 110 ℃. Phloroglucinol sublimes at higher temperatures with partial decomposition.
Uses Phloroglucinol is mainly used as a coupling agent in printing. It is an active component of Tollen's reagent and Gunzburg reagent used to test pentoses and hydrochloric acid in gastric juice respectively. In analytical chemistry, it is used to study condensed tannins by means of depolymerization. It is also involved in the synthesis of 2,4,6-triamino-1,3,5- trinitrobenzene, trinitrophloroglucinol and pharmaceuticals like flopropione.
Uses Phloroglucinol (1,3,5-trihydroxybenzene) is the core structure of a large family of substituted phenolics with broad, albeit weak, biological activity. Phloroglucinol is a useful metabolite for HPLC/DAD and bioassay dereplication.diagnostic aid growth hormone releasing factor. Antispasmodic.
Definition ChEBI: Phloroglucinol is a benzenetriol with hydroxy groups at position 1, 3 and 5. It has a role as an algal metabolite.
Application Phloroglucinol (phlo) is a phenol derivative that shows cyctoprotective effect from oxidative damage by enhancing the activity of cellular catalase.
It can react with benzaldehyde derivatives to form phloroglucinol-based microporous polymeric organic frameworks (phlo-POF) with potential applications in ion-exchange and gas adsorption.
Phlo can also be used to prepare synthetic analogs of A-type proanthocyanidins (PACs) such as 2,8-dioxabicyclo[3.3.1]nonane derivatives by reacting with the corresponding flavylium salts.
General Description Phloroglucinol is a trihydroxybenzene with antithrombotic, profibrinolytic, antimicrobial, antimalarial, cancer chemopreventive, anti-HIV and anti-leishmanial activities. Phloroglucinol (PG) is a biosynthetic precursor of the 2,4-diacetylphloroglucinol (DAPG) an antibiotic against soil-borne diseases. Phloroglucinol is a useful intermediate because it is polyfunctional.
Flammability and Explosibility Not classified
Safety Profile Moderately toxic by subcutaneous and intraperitoneal routes. Mildly toxic by ingestion. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. Used in diazo-type printing and textile dyeing, in microscopy as a bone specimen decalcifier
Purification Methods Crystallise the triol from water, and store it in the dark under nitrogen. [Beilstein 6 IV 7361.]