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2144-08-3

Basic Information
CAS No.: 2144-08-3
Name: 2,3,4-Trihydroxybenzaldehyde
Article Data: 15
Molecular Structure:
Molecular Structure of 2144-08-3 (2,3,4-Trihydroxybenzaldehyde)
Formula: C7H6O4
Molecular Weight: 154.122
Synonyms: 3,4-Dihydroxysalicylaldehyde;NSC 22595;benzaldehyde, 2,3,4-trihydroxy-;
EINECS: 218-404-2
Density: 1.598 g/cm3
Melting Point: 159-161 °C(lit.)
Boiling Point: 301.9 °C at 760 mmHg
Flash Point: 150.6 °C
Solubility: 1.541g/L at 25℃
Appearance: light brown to beige-brown powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39-36
PSA: 77.76000
LogP: 0.61590
Synthetic route

C8H4O5

2144-08-3

2,3,4-trihydroxybenzylaldehyde

Conditions
ConditionsYield
With water Reflux;94.6%
864131-95-3

N,N'-diphenylformamidine

87-66-1

2-hydroxyresorcinol

2144-08-3

2,3,4-trihydroxybenzylaldehyde

Conditions
ConditionsYield
at 110℃; und Kochen des Reaktionsprodukts mit Natronlauge;
103-70-8

Formanilid

87-66-1

2-hydroxyresorcinol

2144-08-3

2,3,4-trihydroxybenzylaldehyde

Conditions
ConditionsYield
With diethyl ether; trichlorophosphate Zerlegen des ausgeschiedenen salzsauren Pyrogallolaldehydanilins durch Erwaeemen mit verd. Natronlauge;
74-90-8

hydrogen cyanide

87-66-1

2-hydroxyresorcinol

2144-08-3

2,3,4-trihydroxybenzylaldehyde

Conditions
ConditionsYield
With hydrogenchloride; aluminium trichloride; benzene at 40℃; Zersetzung mit Eiswasser;
With hydrogenchloride; diethyl ether; zinc(II) chloride Zersetzung des sich ausscheidenden salzsauren Aldimids mit siedendem Wasser;
With hydrogenchloride
92114-96-0

mercury fulminate

87-66-1

2-hydroxyresorcinol

2144-08-3

2,3,4-trihydroxybenzylaldehyde

Conditions
ConditionsYield
With hydrogenchloride; diethyl ether; mercury(II) fulminate Zerlegen des dabei erhaltenen Oxims durch Kochen mit verd. Schwefelsaeure;
With hydrogenchloride; diethyl ether; mercury(II) fulminate Zerlegen des dabei erhaltenen Oxims durch Kochen mit verd. Schwefelsaeure;
122-51-0

orthoformic acid triethyl ester

87-66-1

2-hydroxyresorcinol

2144-08-3

2,3,4-trihydroxybenzylaldehyde

2,4-dihydroxy-3-O-α-L-rhamnopyranosylbenzaldehyde

A

6014-42-2

L-rhamnose

B

2144-08-3

2,3,4-trihydroxybenzylaldehyde

Conditions
ConditionsYield
With hydrogenchloride; methanol for 4h; Reflux;
109103-74-4

2,3,4-Trihydroxy-benzaldehyd-p-tolylimin

A

2144-08-3

2,3,4-trihydroxybenzylaldehyde

B

106-49-0

p-toluidine

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate
Multi-step reaction with 2 steps
1: [bis(acetoxy)iodo]benzene
2: sodium tetrahydroborate; methanol
View Scheme

C14H11NO3

A

2144-08-3

2,3,4-trihydroxybenzylaldehyde

B

106-49-0

p-toluidine

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate
102-09-0

bis(phenyl) carbonate

2144-08-3

2,3,4-trihydroxybenzylaldehyde

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / tert-butyl methyl ether / Reflux
2: aluminum (III) chloride / tert-butyl methyl ether / 0 - 5 °C
3: water / Reflux
View Scheme
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    Structure Formula Molecular Formula C7H6O4 Molecular Weight 154.122 Specification Appearance: white crystal Purity: 99.0% min M.P.: 159-162¡æ

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    Product name: 2,3,4-Trihydroxybenzaldehyde CAS No.:2144-08-3 Molecule Formula:C7H6O4 Molecule Weight:154.12 Purity: 99.0% Package: 25kg/drum Description:White crystalline powder Manufacture Standards:Enterprise Standard

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The 2,3,4-Trihydroxybenzaldehyde, with the CAS registry number 2144-08-3 and EINECS registry number 218-404-2, it is also known as Pyrogallol-4-carboxaldehyde. It is a kind of light brown to beige-brown powder which is sensitive to air, and belongs to the following product categories: Aromatic Aldehydes & Derivatives (substituted); Benzaldehyde. The molecular formula of this chemical is C7H6O4. What's more, it is used as the intermediate of benserazide.

The physical properties of 2,3,4-Trihydroxybenzaldehyde are as following: (1)ACD/LogP: 1.26; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.25; (4)ACD/LogD (pH 7.4): 0.86; (5)ACD/BCF (pH 5.5): 5.2; (6)ACD/BCF (pH 7.4): 2.15; (7)ACD/KOC (pH 5.5): 112.68; (8)ACD/KOC (pH 7.4): 46.7; (9)#H bond acceptors: 4; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 44.76 Å2; (13)Index of Refraction: 1.734; (14)Molar Refractivity: 38.65 cm3; (15)Molar Volume: 96.3 cm3; (16)Polarizability: 15.32×10-24cm3; (17)Surface Tension: 90.5 dyne/cm; (18)Density: 1.598 g/cm3; (19)Flash Point: 150.6 °C; (20)Enthalpy of Vaporization: 56.37 kJ/mol; (21)Boiling Point: 301.9 °C at 760 mmHg; (22)Vapour Pressure: 0.000573 mmHg at 25°C.

Uses of 2,3,4-Trihydroxybenzaldehyde: It can react with formaldehyde to produce 2,3,4-trihydroxy-5-hydroxymethylbenzaldehyde. This reaction will need reagent 4% NaOH. The reaction time is 3 hours with ambient temperature, and the yield is about 34%.    

2,3,4-Trihydroxybenzaldehyde can react with formaldehyde to produce 2,3,4-trihydroxy-5-hydroxymethylbenzaldehyde

You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=Cc1c(O)c(O)c(O)cc1
(2)InChI: InChI=1/C7H6O4/c8-3-4-1-2-5(9)7(11)6(4)10/h1-3,9-11H
(3)InChIKey: CRPNQSVBEWWHIJ-UHFFFAOYAE

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 2195mg/kg (2195mg/kg)   International Journal of Andrology. Vol. 10, Pg. 741, 1987.