35388-10-4

Basic information

• Product Name: 3,4,5-trihydroxybenzoyl chloride
• Synonyms: 3,4,5-trihydroxybenzoyl chloride;3,4,5-Trihydroxybenzoic acid chloride
• CAS NO: 35388-10-4
• Molecular Formula: C₇H₅ClO₄
• Molecular Weight: 188.5652
• EINECS: 252-539-8
• Mol File: 35388-10-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 441.1°Cat760mmHg
• Flash Point: 220.6°C
• Appearance: /
• Density: 1.696g/cm³
• Vapor Pressure: 2.15E-08mmHg at 25°C
• Refractive Index: 1.683
• CAS DataBase Reference: 3,4,5-trihydroxybenzoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5-trihydroxybenzoyl chloride(35388-10-4)
• EPA Substance Registry System: 3,4,5-trihydroxybenzoyl chloride(35388-10-4)

Safety Data

• Hazardous Substances Data: 35388-10-4(Hazardous Substances Data)

Usage

General Description

3,4,5-Trihydroxybenzoyl Chloride is a chemical compound belonging to the family of benzoic acid and derivatives. Also known as Galloyl Chloride, it has the molecular formula C7H5ClO4. It contains three hydroxyl groups attached to a benzene ring, giving it aromatic properties. However, exposure to it may cause eye irritation, and it may also be harmful if swallowed. In chemistry, it is often used as a reagent or building block for the synthesis of other complex molecules. Currently, information relating to its practical uses and applications, outside of scientific research, remains rather scarce.

InChI:InChI=1/C7H5ClO4/c8-7(12)3-1-4(9)6(11)5(10)2-3/h1-2,9-11H

Synthetic route

3,4,5-trihydroxybenzoic acid (149-91-7) → 3,4,5-trihydroxybenzoyl chloride (35388-10-4)

Conditions	Yield
With thionyl chloride for 2h; Ambient temperature;
With thionyl chloride for 6h; Reflux;
With thionyl chloride at 20℃; for 2h;

3,4,5-trihydroxybenzoyl chloride (35388-10-4) + 2,6-bis(4-methoxyphenyl)-1-methylpiperidin-4-one oxime (1461755-51-0) → 2,6-bis(4-methoxyphenyl)-1-methylpiperidin-4-one O-3,4,5-trihydroxybenzoyloxime (1461755-64-5)

Conditions	Yield
Stage #1: 2,6-bis(4-methoxyphenyl)-1-methylpiperidin-4-one oxime With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 0.416667h; Stage #2: 3,4,5-trihydroxybenzoyl chloride In N,N-dimethyl-formamide at 20℃; for 8h;	87.17%

C20H24N2O5 (1415591-05-7) + 3,4,5-trihydroxybenzoyl chloride (35388-10-4) → C27H28N2O9 (1415591-16-0)

Conditions	Yield
Stage #1: C20H24N2O5 With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 0.416667h; Stage #2: 3,4,5-trihydroxybenzoyl chloride In N,N-dimethyl-formamide at 20℃; for 1h;	84.2%

3,4,5-trihydroxybenzoyl chloride (35388-10-4) + p,p'-bis(2-amino-1,3,4-oxadiazol-5-ylmethylamino)diphenylsulphone (116615-33-9) → C32H26N8O12S

Conditions	Yield
With pyridine In 1,4-dioxane Heating;	66%

1H-imidazole (288-32-4) + 3,4,5-trihydroxybenzoyl chloride (35388-10-4) → N-(3,4,5-trihydroxybenzoyl)imidazole

Conditions	Yield
In chloroform at 20℃; Schotten-Baumann Reaction;	60%

3-HYDROXYPYRIDINE (109-00-2) + 3,4,5-trihydroxybenzoyl chloride (35388-10-4) → gallic acid-[3]pyridyl ester

octanol (111-87-5) + 3,4,5-trihydroxybenzoyl chloride (35388-10-4) → Octyl gallate (1034-01-1)

1-Decanol (112-30-1) + 3,4,5-trihydroxybenzoyl chloride (35388-10-4) → decyl gallate (19198-75-5)

1-dodecyl alcohol (112-53-8) + 3,4,5-trihydroxybenzoyl chloride (35388-10-4) → dodecyl gallate (1166-52-5)

Conditions	Yield
at 100℃;

3,4,5-trihydroxybenzoyl chloride (35388-10-4) + (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8) → 3,4,5-trimethoxy-benzoic acid-(2,3-dihydroxy-propyl ester)

Conditions	Yield
With quinoline Erwaermen des Reaktionsprodukts mit wss. HCl;

3,4,5-trihydroxybenzoyl chloride (35388-10-4) + hexan-1-ol (111-27-3) → n-hexyl gallate (1087-26-9)

3,4,5-trihydroxybenzoyl chloride (35388-10-4) + 2-amino-5-(2'-isopropyl-5'-methylphenoxymethyl)-1,3,4-oxadiazole (22670-72-0) → 3,4,5-Trihydroxy-N-[5-(2-isopropyl-5-methyl-phenoxymethyl)-[1,3,4]oxadiazol-2-yl]-benzamide

Conditions	Yield
With pyridine

3,4,5-trihydroxybenzoyl chloride (35388-10-4) + 7-bromo-5-aminomethyl-2,3-dimethoxyquinoxaline (188699-62-9) → N-(2,3-Dimethoxy-7-nitro-quinoxalin-5-ylmethyl)-3,4,5-trihydroxy-benzamide

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 72h;

methanol (67-56-1) + 3,4,5-trihydroxybenzoyl chloride (35388-10-4) → methyl galloate (99-24-1)

Conditions	Yield
for 0.5h; Yield given;

3,4,5-trihydroxybenzoyl chloride (35388-10-4) → 3,4,5-Tris-(2-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzoic acid methyl ester (168640-85-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 0.5 h 2: 68 percent / K2CO3 / dimethylformamide / 24 h / 80 °C 3: 65 percent / H2 / 10percent Pd/C / ethanol / 3 h / Ambient temperature View Scheme

3,4,5-trihydroxybenzoyl chloride (35388-10-4) → 3,4,5-Tris-(2-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzoic acid (168640-84-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 0.5 h 2: 68 percent / K2CO3 / dimethylformamide / 24 h / 80 °C 3: 100 percent / aq. KOH / ethanol / 2 h / Heating View Scheme

3,4,5-trihydroxybenzoyl chloride (35388-10-4) → 3,4,5-Tris-[2-(2-{2-[2-(2-chloro-acetylamino)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-benzoic acid methyl ester (168640-86-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 0.5 h 2: 68 percent / K2CO3 / dimethylformamide / 24 h / 80 °C 3: 65 percent / H2 / 10percent Pd/C / ethanol / 3 h / Ambient temperature 4: 62 percent / Et3N / ethanol / 2 h / Ambient temperature View Scheme

3,4,5-trihydroxybenzoyl chloride (35388-10-4) → 3,4,5-Tris-(2-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzoic acid methyl ester (168640-83-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.5 h 2: 68 percent / K2CO3 / dimethylformamide / 24 h / 80 °C View Scheme

3,4,5-trihydroxybenzoyl chloride (35388-10-4) → 3,4,5-Tris-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-benzoic acid methyl ester (202803-50-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 0.5 h 2: 65 percent / K2CO3 / dimethylformamide / 24 h / 80 °C 3: H2 / 10percent Pd/C / ethanol / 3 h / Ambient temperature View Scheme

3,4,5-trihydroxybenzoyl chloride (35388-10-4) → methyl 3,4,5-tris(2-(2-(2-azidoethoxy) ethoxy) ethoxy) benzoate (202803-47-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.5 h 2: 65 percent / K2CO3 / dimethylformamide / 24 h / 80 °C View Scheme

3,4,5-trihydroxybenzoyl chloride (35388-10-4) → 3,4,5-Tris-(2-{2-[2-(2-chloro-acetylamino)-ethoxy]-ethoxy}-ethoxy)-benzoic acid methyl ester (202803-53-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 0.5 h 2: 65 percent / K2CO3 / dimethylformamide / 24 h / 80 °C 3: H2 / 10percent Pd/C / ethanol / 3 h / Ambient temperature 4: 65 percent / Et3N / ethanol / 2 h / Ambient temperature View Scheme

3,4,5-trihydroxybenzoyl chloride (35388-10-4) → 3,4,5-Trihydroxy-N-(7-nitro-2,3-dioxo-1,2,3,4-tetrahydro-quinoxalin-5-ylmethyl)-benzamide

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 72 h / 0 - 20 °C 2: HBr, AcOH / 16 h / Ambient temperature View Scheme

5,7-bis(benzyloxy)-6-methoxy-(1',2'-di-deoxy-β-D-glucopyranoso)[2',1'-c]isochroman-1-one (1240795-78-1) + 3,4,5-trihydroxybenzoyl chloride (35388-10-4) → C35H32O13 (1350431-83-2)

Conditions	Yield
With pyridine; dmap In dichloromethane at 0 - 20℃;

methyl 2-(2-acetyl-3,5-dihydroxyphenyl)acetate (126495-72-5) + 3,4,5-trihydroxybenzoyl chloride (35388-10-4) → C25H20O13

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 24h; Cooling with ice;

3,4,5-trihydroxybenzoyl chloride (35388-10-4) + C12H20N2O7Pt → C19H24N2O11Pt

Conditions	Yield
In acetone at 20℃; Inert atmosphere;

3,4,5-trihydroxybenzoyl chloride (35388-10-4) → 3,4,5-trihydroxybenzoic acid hydrazide (5782-85-4)

Conditions	Yield
With hydrazine for 5h; Reflux;

4-(aminomethyl)pyridine (3731-53-1) + 3,4,5-trihydroxybenzoyl chloride (35388-10-4) → 3,4,5-trihydroxy-N-(pyridin-4-ylmethyl)benzamide

Conditions	Yield
In dichloromethane at 20℃; for 2h;	14 mg

3,4,5-trihydroxybenzoyl chloride (35388-10-4) + [RuII(2,2-bipyridine)2(pyridin-4-ylmethanamine)2]Cl2 → [RuII(2,2'-bipyridine)2(3,4,5-trihydroxy-N-(pyridin-4-ylmethyl)benzamide)2]Cl2

Conditions	Yield
In dichloromethane at 20℃; for 5h; Darkness;	62 mg

Upstream product

• 149-91-7 3,4,5-trihydroxybenzoic acid 

Downstream Products

• 1461755-64-5 2,6-bis(4-methoxyphenyl)-1-methylpiperidin-4-one O-3,4,5-trihydroxybenzoyloxime 
• 202803-53-0 3,4,5-Tris-(2-{2-[2-(2-chloro-acetylamino)-ethoxy]-ethoxy}-ethoxy)-benzoic acid methyl ester 
• 202803-47-2 methyl 3,4,5-tris(2-(2-(2-azidoethoxy) ethoxy) ethoxy) benzoate 
• 202803-50-7 3,4,5-Tris-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-benzoic acid methyl ester 
• 168640-83-3 3,4,5-Tris-(2-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzoic acid methyl ester 
• 168640-86-6 3,4,5-Tris-[2-(2-{2-[2-(2-chloro-acetylamino)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-benzoic acid methyl ester 
• 168640-84-4 3,4,5-Tris-(2-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzoic acid 
• 168640-85-5 3,4,5-Tris-(2-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzoic acid methyl ester 
• 99-24-1 methyl galloate 
• 1087-26-9 n-hexyl gallate 
• 1166-52-5 dodecyl gallate 
• 19198-75-5 decyl gallate 
• 1034-01-1 Octyl gallate 

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