6099-90-7

Basic information

• Product Name: Phloroglucinol dihydrate
• Synonyms: PHLORGLUCINOL DIHYDRATE;PHLOROGLUCINOL DIHYDRATE;PHLOROGLUCIN;PHLOROGLUCIN DIHYDRATE;m-Trihydroxybenzene;Phloroglucin 1,3,5-Trihydroxybenzene;Phloroglucinol dihydrous;Phlorogluctinol(Dihydrate)
• CAS NO: 6099-90-7
• Molecular Formula: C₆H₆O₃*2H₂O
• Molecular Weight: 162.14
• EINECS: 203-611-2
• Product Categories: organic;Organic Building Blocks;Oxygen Compounds;Polyols
• Mol File: 6099-90-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 218-221 °C (A)(lit.)
• Boiling Point: 331.1 °C at 760 mmHg
• Flash Point: 100 °C
• Appearance: Almost white to beige/Crystalline Powder
• Vapor Pressure: 8.27E-05mmHg at 25°C
• Storage Temp.: Store at RT.
• Solubility: Sparingly soluble in water, freely soluble in ethanol (96 per cent), practically insoluble in methylene chloride.
• Water Solubility: slightly soluble
• Sensitive: Light Sensitive
• Stability: Stable. Incompatible with acid chlorides, acid anhydrides, bases, oxidizing agents. Combustible.
• Merck: 14,7328
• BRN: 5109263
• CAS DataBase Reference: Phloroglucinol dihydrate(CAS DataBase Reference)
• NIST Chemistry Reference: Phloroglucinol dihydrate(6099-90-7)
• EPA Substance Registry System: Phloroglucinol dihydrate(6099-90-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36-24/25
• WGK Germany: 2
• RTECS: DC4662500
• TSCA: Yes
• Hazardous Substances Data: 6099-90-7(Hazardous Substances Data)

Usage

Description

Phloroglucinol dihydrate is an off-white powder with a variety of applications across different industries. It is a versatile compound known for its unique chemical properties and diverse uses.

Uses

Used in Diazo-type Printing and Textile Dyeing:
Phloroglucinol dihydrate is used as a reactant for the synthesis of various compounds, which are essential in the diazo-type printing and textile dyeing industries. Its chemical properties make it suitable for creating vibrant and long-lasting colors in fabrics.
Used in Cosmetics:
Phloroglucinol dihydrate is used as an antioxidant and hair colorant in the cosmetics industry. Its ability to protect against oxidative stress and enhance hair color makes it a valuable ingredient in various cosmetic products.
Used as a Reagent:
Phloroglucinol dihydrate is used as a reagent for the detection of aldehydes, carbohydrates, lignin, and hydrochloric acid (HCl). Its chemical properties allow for accurate and reliable identification of these substances in various applications.
Used in Cloud Seeding:
Phloroglucinol dihydrate is utilized in cloud seeding, a technique used to manipulate weather conditions by promoting the formation of rain or snow. Its properties make it an effective agent in this process.
Used in Rooting Medium for Woody Plants:
Phloroglucinol dihydrate is used as a component in the rooting medium for woody plants, promoting healthy root growth and development. Its presence in the medium enhances the success rate of plant propagation.
Used in the Synthesis of Specific Compounds:
Phloroglucinol Dihydrate is a reactant used in the synthesis of [2-13C, 4-13C]-(2R,3S)-catechin and [2-13C, 4-13C]-(2R,3R)-epicatechin, which are important compounds in various scientific and industrial applications.

InChI:InChI=1/C6H6O3.2H2O/c7-4-1-5(8)3-6(9)2-4;;/h1-3,7-9H;2*1H2

Synthetic route

tetrahydrofuran (109-99-9) + 1,1'-bis(ethenyl-4-pyridyl)ferrocene (222165-10-8) + 1,3,5-Trihydroxybenzene dihydrate (6099-90-7) → 1,1'-bis(ethenyl-4-pyridyl)ferrocene phlorglucinol tetrahydrofuran

Conditions	Yield
In ethanol at room temp. for 7 d; elem. anal.;	100%

ethanol (64-17-5) + 1,1'-bis(ethenyl-4-pyridyl)ferrocene (222165-10-8) + 1,3,5-Trihydroxybenzene dihydrate (6099-90-7) → 1,1'-bis(ethenyl-4-pyridyl)ferrocene phlorglucinol ethanol

Conditions	Yield
In ethanol at room temp. for 7 d; elem. anal.;	100%

1,3,5-Trihydroxybenzene dihydrate (6099-90-7) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2,4,6-trihydroxybenzaldehyde (487-70-7)

Conditions	Yield
With trichlorophosphate In ethyl acetate at 20℃; for 1h; Vilsmeier-Haack Formylation; Cooling with ice;	98%

6-fluoroisatin (324-03-8) + 1,3,5-Trihydroxybenzene dihydrate (6099-90-7) → acide 6-fluoro-1,3-dihydroacridine-9-carboxylique (82260-62-6)

Conditions	Yield
With sodium hydroxide Heating;	92%

7-fluoro-1H-indole-2,3-dione (317-20-4) + 1,3,5-Trihydroxybenzene dihydrate (6099-90-7) → acide 5-fluoro-1,3-dihydroacridine-9-carboxylique (82260-61-5)

Conditions	Yield
With sodium hydroxide for 5h; Heating;	92%

1,3,5-Trihydroxybenzene dihydrate (6099-90-7) + acetyl chloride (75-36-5) → 1,3,5-triacetyl-2,4,6-trihydroxybenzene (2161-87-7)

Conditions	Yield
With aluminum (III) chloride for 1h; Reagent/catalyst; Time; Fries Phenol Ester Rearrangement; Reflux;	91%
With aluminum (III) chloride for 1h; Reflux;	91%

1,3,5-Trihydroxybenzene dihydrate (6099-90-7) + ethyl 4,4,4-trifluoroacetoacetate (372-31-6) → 5,7-Dihydroxy-4-trifluoromethylcoumarin (82747-44-2)

Conditions	Yield
With trifluoroacetic acid for 15h; Heating;	80%

1,3,5-Trihydroxybenzene dihydrate (6099-90-7) + dihydro-2,2 oxo-3 F-octanoate d'ethyle (82747-28-2) → F-pentyl-4 dihydroxy-5,7 coumarine

Conditions	Yield
With trifluoroacetic acid for 15h; Heating;	75%

1,3,5-Trihydroxybenzene dihydrate (6099-90-7) + dihydro-2,2 oxo-3 F-decanoate d'ethyle (82747-29-3) → F-heptyl-4 dihydroxy-5,7 coumarine

Conditions	Yield
With trifluoroacetic acid for 15h; Heating;	73%

5-fluoro-1H-indole-2,3-dione (443-69-6) + 1,3,5-Trihydroxybenzene dihydrate (6099-90-7) → acide 7-fluoro-1,3-dihydroacridine-9-carboxylique (82260-63-7)

Conditions	Yield
With sodium hydroxide Heating;	72%

(2,2,3,3,4,4,4-heptafluorobutanoyl)acetic acid ethyl ester (336-62-9) + 1,3,5-Trihydroxybenzene dihydrate (6099-90-7) → F-propyl-4 dihydroxy-5,7 coumarine

Conditions	Yield
With trifluoroacetic acid for 15h; Heating;	70%

indan-1,2,3-trione hydrate (485-47-2) + 1,3,5-Trihydroxybenzene dihydrate (6099-90-7) → (trihydroxy-2,4,6 phenyl)-2 hydroxy-2 indanedione-1,3 monohydrate

Conditions	Yield
In water for 0.1h; Heating;	67%

ethyl butyroyl acetate (3249-68-1) + 1,3,5-Trihydroxybenzene dihydrate (6099-90-7) → 5,7-dihydroxy-4-propylcoumarin (66346-59-6)

Conditions	Yield
With sulfuric acid In ethyl acetate
With sulfuric acid In ethyl acetate
With sulfuric acid In ethyl acetate
In ethyl acetate
With sulfuric acid In ethyl acetate

3,5-dihydroxyphenol (108-73-6) + 2,4,6-tribromophloroglucinol (3354-82-3) + 1,3,5-Trihydroxybenzene dihydrate (6099-90-7) + acryloyl chloride (814-68-6) → tribromophloroglucinol triacrylate (217825-79-1)

Conditions	Yield
With bromine; triethylamine In n-heptane; dichloromethane; acetone; acetonitrile

1,3,5-Trihydroxybenzene dihydrate (6099-90-7) + Ethyl 2-benzylacetoacetate (620-79-1) → 3-benzyl-5,7-dihydroxy-4-methyl-2H-chromen-2-one (219551-85-6)

Conditions	Yield
With hydrogenchloride In ethanol
With hydrogenchloride In ethanol

2,6-bis(hydroxymethyl)-4-methylphenol (91-04-3) + p-toluenesulfonic acid monohydrate (6192-52-5) + 1,3,5-Trihydroxybenzene dihydrate (6099-90-7) → 2,6-bis[(2,4,6-trihydroxyphenyl)methyl]-4-methylphenol

Conditions	Yield
In water

5-5-ferrocenylpyrimidine (597544-31-5) + 1,3,5-Trihydroxybenzene dihydrate (6099-90-7) → ([5-ferrocenylpyrimidine]*phloroglucinol*2H2O)n

Conditions	Yield
In acetonitrile addn. of soln. of phloroglucinol*2H2O (1 equiv.) in MeCN to soln. of 5-ferrocenylpyrimidine (1 equiv.) in MeCN; crystn. for a few days at room temp. in air; elem. anal.;

1,3,5-Trihydroxybenzene dihydrate (6099-90-7) → 1,3,5-triacetyl-2,4,6-tris(5'-azidopentyloxy)benzene

Conditions	Yield
Multi-step reaction with 3 steps 1: aluminum (III) chloride / 1 h / Reflux 2: potassium carbonate / acetonitrile / 48 h / Reflux 3: sodium azide / acetone; water / 8 h / Reflux View Scheme

1,3,5-Trihydroxybenzene dihydrate (6099-90-7) → 1,3,5-triacetyl-2,4,6-tris(5'-aminopentyloxy)benzene trihydrochloride

Conditions	Yield
Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / 1 h / Reflux 2.1: potassium carbonate / acetonitrile / 48 h / Reflux 3.1: sodium azide / acetone; water / 8 h / Reflux 4.1: ammonium chloride; zinc / water; ethanol / 0.25 h / Reflux 4.2: 3 h View Scheme

1,3,5-Trihydroxybenzene dihydrate (6099-90-7) → C33H51N3O9

Conditions	Yield
Multi-step reaction with 5 steps 1.1: aluminum (III) chloride / 1 h / Reflux 2.1: potassium carbonate / acetonitrile / 48 h / Reflux 3.1: sodium azide / acetone; water / 8 h / Reflux 4.1: ammonium chloride; zinc / water; ethanol / 0.25 h / Reflux 4.2: 3 h 5.1: dmap; pyridine / 20 °C View Scheme

1,3,5-Trihydroxybenzene dihydrate (6099-90-7) → 1-4,6-dihydroxy-2-methoxy-3-methylphenylbutan-1-one (478-48-8)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: trichlorophosphate / ethyl acetate / 1 h / 20 °C / Cooling with ice 2.1: hydrogenchloride; zinc / ethyl acetate; diethyl ether / 0.17 h / Cooling with ice 3.1: aluminum (III) chloride / nitrobenzene / 0.5 h 3.2: 24 h / 65 °C / Inert atmosphere 4.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; dichloromethane / 3 h / Cooling with ice 5.1: potassium carbonate 6.1: sodium hydroxide / methanol; water / 2.5 h / 40 °C / Inert atmosphere View Scheme

1,3,5-Trihydroxybenzene dihydrate (6099-90-7) → 2,4,6-trihydroxytoluene (88-03-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: trichlorophosphate / ethyl acetate / 1 h / 20 °C / Cooling with ice 2: hydrogenchloride; zinc / ethyl acetate; diethyl ether / 0.17 h / Cooling with ice View Scheme

1,3,5-Trihydroxybenzene dihydrate (6099-90-7) → 1-(2,4,6-trihydroxy-3-methylphenyl)butan-1-one (1509-06-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trichlorophosphate / ethyl acetate / 1 h / 20 °C / Cooling with ice 2.1: hydrogenchloride; zinc / ethyl acetate; diethyl ether / 0.17 h / Cooling with ice 3.1: aluminum (III) chloride / nitrobenzene / 0.5 h 3.2: 24 h / 65 °C / Inert atmosphere View Scheme

1,3,5-Trihydroxybenzene dihydrate (6099-90-7) → C19H26O6

Conditions

Yield

Multi-step reaction with 4 steps 1.1: trichlorophosphate / ethyl acetate / 1 h / 20 °C / Cooling with ice 2.1: hydrogenchloride; zinc / ethyl acetate; diethyl ether / 0.17 h / Cooling with ice 3.1: aluminum (III) chloride / nitrobenzene / 0.5 h 3.2: 24 h / 65 °C / Inert atmosphere 4.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; dichloromethane / 3 h / Cooling with ice View Scheme

1,3,5-Trihydroxybenzene dihydrate (6099-90-7) → C20H28O6

Conditions

Yield

Multi-step reaction with 5 steps 1.1: trichlorophosphate / ethyl acetate / 1 h / 20 °C / Cooling with ice 2.1: hydrogenchloride; zinc / ethyl acetate; diethyl ether / 0.17 h / Cooling with ice 3.1: aluminum (III) chloride / nitrobenzene / 0.5 h 3.2: 24 h / 65 °C / Inert atmosphere 4.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; dichloromethane / 3 h / Cooling with ice 5.1: potassium carbonate View Scheme

Downstream Products

• 66346-59-6 5,7-dihydroxy-4-propylcoumarin 
• 217825-79-1 tribromophloroglucinol triacrylate 
• 219551-85-6 3-benzyl-5,7-dihydroxy-4-methyl-2H-chromen-2-one 
• 2161-87-7 1,3,5-triacetyl-2,4,6-trihydroxybenzene 
• 478-48-8 1-4,6-dihydroxy-2-methoxy-3-methylphenylbutan-1-one 
• 88-03-9 2,4,6-trihydroxytoluene 
• 1509-06-4 1-[3-methyl-2,4,6-trihydroxyphenyl]-1-butanone 
• 487-70-7 2,4,6-trihydroxybenzaldehyde 

Relevant articles and documents

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