| Identification | More | [Name]
3,4,5-Trimethoxybenzoyl chloride | [CAS]
4521-61-3 | [Synonyms]
3,4,5-TRIMETHOXYBENZOYL CHLORIDE
AKOS BBS-00003922
3,4,5-trimethoxy-benzoylchlorid
Benzoyl chloride, 3,4,5-trimethoxy-
Trimethylgalloyl chloride
Tri-O-methylgalloyl chloride
3,4,5-Trimethoxybenzoic acid chloride | [EINECS(EC#)]
224-851-4 | [Molecular Formula]
C10H11ClO4 | [MDL Number]
MFCD00000675 | [Molecular Weight]
230.64 | [MOL File]
4521-61-3.mol |
| Chemical Properties | Back Directory | [Melting point ]
81-84 °C (lit.) | [Boiling point ]
185 °C/18 mmHg (lit.) | [density ]
1,214 g/cm3 | [refractive index ]
1.4571 (estimate) | [Fp ]
185°C/18mm | [storage temp. ]
Store at 0-5°C | [solubility ]
soluble in Toluene | [form ]
powder to crystal | [color ]
White to Orange to Green | [Sensitive ]
Moisture Sensitive | [BRN ]
403117 | [InChI]
1S/C10H11ClO4/c1-13-7-4-6(10(11)12)5-8(14-2)9(7)15-3/h4-5H,1-3H3 | [InChIKey]
BUHYMJLFRZAFBF-UHFFFAOYSA-N | [SMILES]
COc1cc(cc(OC)c1OC)C(Cl)=O | [LogP]
2.400 (est) | [CAS DataBase Reference]
4521-61-3(CAS DataBase Reference) | [NIST Chemistry Reference]
3,4,5-Trimethoxybenzoyl chloride(4521-61-3) | [EPA Substance Registry System]
4521-61-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R14:Reacts violently with water.
R34:Causes burns.
R37:Irritating to the respiratory system. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 3261 8/PG 2
| [WGK Germany ]
1
| [F ]
9-21 | [TSCA ]
TSCA listed | [HazardClass ]
8 | [PackingGroup ]
II | [HS Code ]
29189900 | [Storage Class]
8A - Combustible corrosive hazardous materials | [Hazard Classifications]
Skin Corr. 1B
STOT SE 3 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
3,4,5-Trimethoxy benzoic acid-->Chloroform-->Thionyl chloride | [Preparation Products]
TROXIPIDE-->Capobenic acid-->3,4,5-Trimethoxyaniline-->3',4',5',5,6,7-HEXAMETHOXYFLAVONE-->Trimethobenzamide-->3,4,5-TRIMETHOXYBENZAMIDE-->1-(3,4,5-Trimethoxybenzoyl)piperidine-->(5-nitroindazol-1-yl)-(3,4,5-trimethoxyphenyl)methanone-->3,4,5-trimethoxy-N-(2-nitrophenyl)benzamide |
| Hazard Information | Back Directory | [Uses]
3,4,5-Trimethoxybenzoyl Chloride is used as a reagent in the synthesis of 2-methyl-8-(3,4,5-trimethoxybenzamido)-1,2,3,4-tetrahydroisoquinoline and its analogs which display great antihypertensive activity. | [Synthesis]
The general procedure for the synthesis of 3,4,5-trimethoxybenzoyl chloride from 3,4,5-trimethoxybenzoic acid was as follows: thionyl chloride (13.7 mL, 189 mmol) was added dropwise to a solution of CHCl3 (30 mL) containing 3,4,5-trimethoxybenzoic acid (8.00 g, 37.7 mmol). After the dropwise addition, the reaction mixture was heated to reflux and maintained for 4 hours. Upon completion of the reaction, the mixture was cooled to room temperature. Subsequently, the solvent and excess thionyl chloride were removed by distillation under reduced pressure to afford 3,4,5-trimethoxybenzoyl chloride as a colorless oil in quantitative yield. The obtained product can be used in the subsequent reaction without further purification. The characteristic absorption peaks of the infrared spectrum (NaCl) were: νmax/cm-1 2970, 2944, 1750, 1590, 1457, 1415, 1130, 1128. | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 22, p. 5864 - 5869
[2] Tetrahedron, 2011, vol. 67, # 25, p. 4601 - 4611
[3] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 20, p. 6042 - 6054
[4] Letters in Drug Design and Discovery, 2018, vol. 15, # 12, p. 1319 - 1328
[5] Bulletin of the Chemical Society of Japan, 2012, vol. 85, # 2, p. 236 - 244 |
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