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86-81-7

Basic Information
CAS No.: 86-81-7
Name: 3,4,5-Trimethoxybenzaldehyde
Article Data: 250
Molecular Structure:
Molecular Structure of 86-81-7 (3,4,5-Trimethoxybenzaldehyde)
Formula: C10H12O4
Molecular Weight: 196.203
Synonyms: NSC 16692;
EINECS: 201-701-6
Density: 1.133 g/cm3
Melting Point: 72-74 °C(lit.)
Boiling Point: 311.4 °C at 760 mmHg
Flash Point: 136.8 °C
Solubility: slightly soluble in water; soluble in methanol: 0.1 g/mL, clear
Appearance: white to creamy powder or flakes
Hazard Symbols: IrritantXi,CorrosiveC
Risk Codes: 36/37/38-34
Safety: 22-24/25-45-36/37/39-27-26
PSA: 44.76000
LogP: 1.52490
Synthetic route
227624-45-5

acetoxy(benzo[1,3]dioxol-5-yl)(dimethylphenylsilyloxy)methane

86-81-7

3,4,5-trimethoxy-benzaldehyde

Conditions
ConditionsYield
With silica gel Hydrolysis;100%
3840-31-1

(3,4,5-trimethoxyphenyl)methanol

86-81-7

3,4,5-trimethoxy-benzaldehyde

Conditions
ConditionsYield
With tert.-butylhydroperoxide; V/SiO2 In decane; tert-butyl alcohol at 25℃; for 5h;99.6%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In aq. phosphate buffer; acetonitrile at 20℃; for 24h; pH=6; Enzymatic reaction;99%
With Iron(III) nitrate nonahydrate; oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 60℃; for 3h; Schlenk technique; Green chemistry;99%

2,6-dibromo-3,4,5-trimethoxybenzyl alcohol

86-81-7

3,4,5-trimethoxy-benzaldehyde

Conditions
ConditionsYield
Stage #1: 2,6-dibromo-3,4,5-trimethoxybenzyl alcohol With potassium pyrosulfate In hexane at 36℃; for 120h;
Stage #2: With sodium nitrate; hydrogen hexachloroiridate In hexane at 45℃; for 3h; Temperature;
99.1%
227624-38-6

(dimethylphenylsilyl)(3,4,5-trimethoxyphenyl)methanol

86-81-7

3,4,5-trimethoxy-benzaldehyde

Conditions
ConditionsYield
Stage #1: (dimethylphenylsilyl)(3,4,5-trimethoxyphenyl)methanol With tert.-butylnitrite In benzene Nitrosation;
Stage #2: In benzene at 0℃; Elimination; Photolysis; Further stages.;
98%
3840-30-0

5-(chloromethyl)-1,2,3-trimethoxybenzene

86-81-7

3,4,5-trimethoxy-benzaldehyde

Conditions
ConditionsYield
With 1-dodecyl-3-methylimidazolium iron chloride; periodic acid at 30℃; for 1.5h;98%
Multi-step reaction with 2 steps
1: 90 °C
2: acetic acid; water / 80 °C
View Scheme
77-78-1

dimethyl sulfate

134-96-3

syringic aldehyde

86-81-7

3,4,5-trimethoxy-benzaldehyde

Conditions
ConditionsYield
With sodium hydroxide; adogen 464 In dichloromethane; water for 16h; Ambient temperature;96%
With potassium hydroxide; sodium carbonate In water; acetone for 18h; Heating;91.5%
With potassium carbonate In acetone for 2h; Heating;9 g
With potassium carbonate In acetone Williamson Ether Synthesis;
57009-70-8

2-(3,4,5-trimethoxyphenyl)-1,3-dithiane

86-81-7

3,4,5-trimethoxy-benzaldehyde

Conditions
ConditionsYield
Stage #1: 2-(3,4,5-trimethoxyphenyl)-1,3-dithiane With acetyl chloride; sodium nitrite In dichloromethane at 0 - 5℃; for 0.25h;
Stage #2: With water In dichloromethane at 0 - 20℃; for 1.25h;
96%
With tetra-N-butylammonium tribromide In dichloromethane at 0 - 5℃; for 0.5h;86%
With tert.-butylhydroperoxide In methanol; water Heating;76%

5-(bis-ethylsulfanyl-methyl)-1,2,3-trimethoxy-benzene

86-81-7

3,4,5-trimethoxy-benzaldehyde

Conditions
ConditionsYield
With tetra-N-butylammonium tribromide In dichloromethane at 0 - 5℃; for 0.0833333h;96%
Stage #1: 5-(bis-ethylsulfanyl-methyl)-1,2,3-trimethoxy-benzene With acetyl chloride; sodium nitrite In dichloromethane at 0 - 5℃; for 0.25h;
Stage #2: With water In dichloromethane at 0 - 20℃; for 0.5h;
96%
With dihydrogen peroxide; vanadia; ammonium bromide In dichloromethane; water at 0 - 5℃; for 1.5h;94%
With ammonium heptamolybdate; dihydrogen peroxide; ammonium bromide; perchloric acid In dichloromethane; water at 0 - 5℃; for 0.5h;80%
75-57-0

tetramethlyammonium chloride

134-96-3

syringic aldehyde

86-81-7

3,4,5-trimethoxy-benzaldehyde

Conditions
ConditionsYield
With caesium carbonate In 1,2-dimethoxyethane at 145℃; for 0.416667h; Microwave irradiation; Inert atmosphere; Sealed vessel;96%
81340-18-3

1,2-dihydro-1-(3,4,5-trimethoxybenzoyl)-2-quinolinecarbonitrile

A

93-10-7

quinoline-2-carboxylic acid

B

86-81-7

3,4,5-trimethoxy-benzaldehyde

Conditions
ConditionsYield
With sulfuric acid at 107℃; for 1h;A n/a
B 95%
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Chemistry

MF: C10H12O4
MW: 196.2
EINECS: 201-701-6
mp  72-74 °C(lit.)
bp  163-165 °C10 mm Hg(lit.)
Fp  163-165°C/10mm
solubility  methanol: 0.1 g/mL, clear
WATER Solubility  slightly soluble
Sensitive  Air Sensitive
Appearance White to light yellow needle crystal.

Uses

3,4,5-Trimethoxybenzaldehyde is an important starting material used in the synthesis of certain pharmaceuticals, such as the antibacterial Trimethoprim.

Production

3,4,5-Trimethoxybenzaldehyde is obtained by methylation with dimethylsulfate.

Toxicity Data With Reference

RTECS  CU8462000

Safety Profile

Hazard Codes  Xi,C
Risk Statements  36/37/38-34
Safety Statements  22-24/25-45-36/37/39-27-26
WGK Germany  3
Hazard Note  Irritant
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