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3-Hydroxyphthalic anhydride

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Name

3-Hydroxyphthalic anhydride

EINECS N/A
CAS No. 37418-88-5 Density 1.625 g/cm3
PSA 63.60000 LogP 0.70280
Solubility N/A Melting Point 199-202 °C(lit.)
Formula C8H4O4 Boiling Point 365.42 °C at 760 mmHg
Molecular Weight 164.117 Flash Point 160.238 °C
Transport Information N/A Appearance Beige powder
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 37418-88-5 (1,3-Isobenzofurandione, 4-hydroxy-) Hazard Symbols IrritantXi
Synonyms

3-Hydroxyphthalicanhydride;4-Hydroxy-2-benzofuran-1,3-dione;4-Hydroxyisobenzofuran-1,3-dione;NSC 80858;

Article Data 23

3-Hydroxyphthalic anhydride Synthetic route

601-97-8

3-hydroxyphthalic acid

37418-88-5

3-hydroxyphthalic anhydride

Conditions
ConditionsYield
at 300℃; Green chemistry;90%
In acetic anhydride at 80℃; for 2h; Temperature;80.1%
With dicyclohexyl-carbodiimide In dimethyl sulfoxide at 150℃; for 1h; Solvent; Temperature; Reagent/catalyst;79.72%
100921-73-1, 135414-50-5

1-(2,2-dimethylpropanoyloxy-3,5)-dioxo-exo-10-oxatricyclo<5.2.1.02.6>dec-8-ene

37418-88-5

3-hydroxyphthalic anhydride

Conditions
ConditionsYield
With sulfuric acid for 0.0833333h;90%
1583-67-1

3-fluorophthalic acid

37418-88-5

3-hydroxyphthalic anhydride

Conditions
ConditionsYield
Stage #1: 3-fluorophthalic acid With copper(l) iodide; potassium hydroxide In N,N-dimethyl-formamide at 100℃; for 6h;
Stage #2: With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 100℃; for 2h; Reagent/catalyst; Solvent; Temperature;
88.2%

1-(2,2-dimethylpropionyl)-4,10-dioxatricyclo[5.2.1.02,6]-dec-8-ene-3,5-dione

37418-88-5

3-hydroxyphthalic anhydride

Conditions
ConditionsYield
With sulfuric acid at -15℃; for 0.0833333h;73%
135414-50-5

1,3-dioxo-3,3a,7,7a-tetrahydro-4,7-epoxy-2-benzofuran-4(1H)-yl 2,2-dimethyl-propanoate

37418-88-5

3-hydroxyphthalic anhydride

Conditions
ConditionsYield
With sulfuric acid at 0 - 15℃; for 0.0833333h;73%
With sulfuric acid at -30℃; for 0.0833333h;73%
With sulfuric acid at -15℃; for 0.25h;
78136-34-2

1-methoxy-7-oxa-norborn-5-ene-2,3-dicarboxylic acid-anhydride

10035-10-6, 12258-64-9

hydrogen bromide

64-19-7

acetic acid

37418-88-5

3-hydroxyphthalic anhydride

3588-80-5

5-methoxynaphthalen-1-ol

37418-88-5

3-hydroxyphthalic anhydride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: KMnO4; diluted NaOH-solution
2: diluted sulfuric acid; KMnO4 / 0 °C
3: potash / beim Schmelzen
4: 150 °C
View Scheme
83-56-7

1,5-dihydroxynaphthalene

37418-88-5

3-hydroxyphthalic anhydride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: NaOH-solution
2: KMnO4; diluted NaOH-solution
3: diluted sulfuric acid; KMnO4 / 0 °C
4: potash / beim Schmelzen
5: 150 °C
View Scheme
14963-97-4

3-methoxyphthalic acid

37418-88-5

3-hydroxyphthalic anhydride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potash / beim Schmelzen
2: 150 °C
View Scheme
Multi-step reaction with 2 steps
1: boron tribromide / dichloromethane / 5 h / 10 - 15 °C
2: dicyclohexyl-carbodiimide / dimethyl sulfoxide / 1 h / 150 °C
View Scheme
17802-94-7

(2-carboxy-3-methoxy-phenyl)-glyoxylic acid

37418-88-5

3-hydroxyphthalic anhydride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: diluted sulfuric acid; KMnO4 / 0 °C
2: potash / beim Schmelzen
3: 150 °C
View Scheme

3-Hydroxyphthalic anhydride Specification

The 3-Hydroxyphthalic anhydride, with the CAS registry number 37418-88-5, is also known as 4-Hydroxyisobenzofuran-1,3-dione. It belongs to the product categories of Phthalic Acids, Esters and Derivatives; Anhydride Monomers; Monomers; Polymer Science; Carbonyl Compounds; Carboxylic Acid Anhydrides; Organic Building Blocks. This chemical's molecular formula is C8H4O4 and molecular weight is 164.11. What's more, its systematic name is 4-Hydroxy-2-benzofuran-1,3-dione. This chemical should be sealed and stored in a cool and dry place. It is used to modify proteins. 

Physical properties of 3-Hydroxyphthalic anhydride are: (1)ACD/LogP: 1.301; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.23; (4)ACD/LogD (pH 7.4): 0.13; (5)ACD/BCF (pH 5.5): 4.88; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 103.31; (8)ACD/KOC (pH 7.4): 8.16; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 63.6 Å2; (13)Index of Refraction: 1.666; (14)Molar Refractivity: 37.563 cm3; (15)Molar Volume: 100.993 cm3; (16)Polarizability: 14.891×10-24cm3; (17)Surface Tension: 76.2 dyne/cm; (18)Density: 1.625 g/cm3; (19)Flash Point: 160.238 °C; (20)Enthalpy of Vaporization: 63.578 kJ/mol; (21)Boiling Point: 365.42 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Uses of 3-Hydroxyphthalic anhydride: it can be used to produce 3-ethoxy-phthalic acid by heating. It will need reagent 10 percent sodium hydroxide and solvent H2O with the reaction time of 24 hours. The yield is about 65%.

3-Hydroxyphthalic anhydride can be used to produce 3-ethoxy-phthalic acid by heating

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1OC(=O)c2cccc(O)c12
(2)Std. InChI: InChI=1S/C8H4O4/c9-5-3-1-2-4-6(5)8(11)12-7(4)10/h1-3,9H
(3)Std. InChIKey: CCTOEAMRIIXGDJ-UHFFFAOYSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 75mg/kg (75mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#08845,

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