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

Chemical Properties

off-white powder

Uses

Different sources of media describe the Uses of 6099-90-7 differently. You can refer to the following data:
1. In diazo-type printing, textile dyeing. In cosmetics, as antioxidant; hair colorant. As reagent for detection of aldehydes, carbohydrates including lignin, and HCl. Cloud seeding. Rooting medium for woody plants.
2. 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.

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

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

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