37418-88-5

Basic information

• Product Name: 1,3-Isobenzofurandione, 4-hydroxy-
• Synonyms: 3-Hydroxyphthalicanhydride;4-Hydroxy-2-benzofuran-1,3-dione;4-Hydroxyisobenzofuran-1,3-dione;NSC 80858
• CAS NO: 37418-88-5
• Molecular Formula: C₈H₄O₄
• Molecular Weight: 164.115
• Product Categories: Anhydride Monomers;Monomers;Polymer Science;Carbonyl Compounds;Carboxylic Acid Anhydrides;Organic Building Blocks;Phthalic Acids, Esters and Derivatives
• Mol File: 37418-88-5.mol
• Article Data: 14

Chemical Properties

• Melting Point: 199-202℃
• Boiling Point: 365.42 °C at 760 mmHg
• Flash Point: 160.238 °C
• Appearance: Beige powder
• Density: 1.625 g/cm³
• Vapor Pressure: 7.47E-06mmHg at 25°C
• Refractive Index: 1.666
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Acetonitrile (Slightly), DMSO (Slightly)
• PKA: 6.25±0.20(Predicted)
• Stability: Hygroscopic
• BRN: 135783
• CAS DataBase Reference: 1,3-Isobenzofurandione, 4-hydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Isobenzofurandione, 4-hydroxy-(37418-88-5)
• EPA Substance Registry System: 1,3-Isobenzofurandione, 4-hydroxy-(37418-88-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: TI3300000
• F: 21
• Hazardous Substances Data: 37418-88-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 37418-88-5 differently. You can refer to the following data:
1. 3-Hydroxyphthalic Anhydride is used to synthesize 3-Hydroxyphthalic Anhydride-modified human serum albumin whichhas high potency as a microbicide for prevention of the sexual transmission of HIV. It is also used as a reagent in organicsynthesis of other compounds including that of inhibitors of NF-κB derived from thalidomide.
2. 3-Hydroxyphthalic Anhydride is used to synthesize 3-Hydroxyphthalic Anhydride-modified human serum albumin whichhas high potency as a microbicide for prevention of the sexual transmission of HIV. It is also used as a reagent in organicsynthesis of other compounds including that of inhibitors of NF-κB derived from thalidomide.

Chemical Properties

Beige powder

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 5092, 1955 DOI: 10.1021/ja01624a042Synthesis, p. 788, 1985 DOI: 10.1055/s-1985-31350

InChI:InChI=1/C8H4O4/c9-5-3-1-2-4-6(5)8(11)12-7(4)10/h1-3,9H

Synthetic route

3-hydroxyphthalic acid (601-97-8) → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
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%

1-(2,2-dimethylpropanoyloxy-3,5)-dioxo-exo-10-oxatricyclo<5.2.1.02.6>dec-8-ene (100921-73-1, 135414-50-5) → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
With sulfuric acid for 0.0833333h;	90%

3-fluorophthalic acid (1583-67-1) → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
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 → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
With sulfuric acid at -15℃; for 0.0833333h;	73%

1,3-dioxo-3,3a,7,7a-tetrahydro-4,7-epoxy-2-benzofuran-4(1H)-yl 2,2-dimethyl-propanoate (135414-50-5) → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
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;

1-methoxy-7-oxa-norborn-5-ene-2,3-dicarboxylic acid-anhydride (78136-34-2) + hydrogen bromide (10035-10-6, 12258-64-9) + acetic acid (64-19-7) → 3-hydroxyphthalic anhydride (37418-88-5)

5-methoxynaphthalen-1-ol (3588-80-5) → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
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

1,5-dihydroxynaphthalene (83-56-7) → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
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

3-methoxyphthalic acid (14963-97-4) → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
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

(2-carboxy-3-methoxy-phenyl)-glyoxylic acid (17802-94-7) → 3-hydroxyphthalic anhydride (37418-88-5)

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

3-nitrophthalic acid anhydride (641-70-3) → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: magnesium sulfate; palladium on activated carbon; hydrogen / ethyl acetate / 18 h / 760.05 Torr 2.1: sulfuric acid / 1 h / 0 °C 2.2: 2 h / 0 - 80 °C 3.1: 135 - 140 °C / 0.04 Torr View Scheme
Multi-step reaction with 2 steps 1.1: hydrogen; magnesium sulfate / 50 °C / 3102.97 Torr 2.1: sulfuric acid / 1 h / 0 °C 2.2: 5 - 80 °C View Scheme
Multi-step reaction with 2 steps 1.1: hydrogen; magnesium sulfate / acetone / 50 °C / 3102.97 Torr 2.1: sulfuric acid / 1 h / 0 °C 2.2: 0.5 h / 5 - 80 °C View Scheme

3-aminophthalic anhydride (17395-99-2) → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid / 1 h / 0 °C 1.2: 2 h / 0 - 80 °C 2.1: 135 - 140 °C / 0.04 Torr View Scheme
Stage #1: 3-aminophthalic anhydride With sulfuric acid at 0℃; for 1h; Stage #2: With sodium nitrite at 5 - 80℃;
Stage #1: 3-aminophthalic anhydride With sulfuric acid at 0℃; for 1h; Stage #2: With sodium nitrite In water at 5 - 80℃; for 0.5h;

3-chlorobenzene-1,2-dicarboxylic acid (27563-65-1) → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
Stage #1: 3-chlorobenzene-1,2-dicarboxylic acid With copper(l) iodide; potassium hydroxide In N,N-dimethyl-formamide at 80℃; for 8h; Stage #2: With phosphoric acid In N,N-dimethyl-formamide at 100℃; for 7.5h;	172.0 g

3-chlorophthalic acid dimethyl ester (61539-35-3) → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
Stage #1: 3-chlorophthalic acid dimethyl ester With copper(I) bromide; sodium hydroxide In dimethyl sulfoxide at 100℃; for 5h; Stage #2: With phosphorus pentoxide In dimethyl sulfoxide at 120℃; for 2h;	188.9 g

3-bromophthalic acid (116-69-8) → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
Stage #1: 3-bromophthalic acid With copper(I) oxide; sodium t-butanolate In tetrahydrofuran at 130℃; for 1.5h; Stage #2: With dicyclohexyl-carbodiimide In tetrahydrofuran at 130℃; for 3.5h;	230.9 g

Reaxys ID: 30570620 → 3-hydroxyphthalic anhydride (37418-88-5)

3-iodophthalic acid (6937-34-4) → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
Stage #1: 3-iodophthalic acid With sodium ethanolate; copper(II) bis(trifluoromethanesulfonate) In dimethyl sulfoxide at 120℃; for 3h; Stage #2: With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dimethyl sulfoxide at 130℃; for 4.5h; Reagent/catalyst; Temperature; Solvent;	247.9 g

3-fluorophthalic acid diethyl ester → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
Stage #1: 3-fluorophthalic acid diethyl ester With copper(l) iodide; potassium tert-butylate In dimethyl sulfoxide at 120℃; for 4h; Stage #2: With dicyclohexyl-carbodiimide In dimethyl sulfoxide at 130℃; for 2.5h;	210.2 g

3-nitrobenzene-1,2-dicarbonitrile (51762-67-5) → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium nitrite; potassium carbonate / dimethyl sulfoxide / 3 h / 160 °C 1.2: pH 3 2.1: water; potassium hydroxide / 90 h / 130 °C 3.1: 300 °C / Green chemistry View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate; sodium nitrite / dimethyl sulfoxide / 20 - 160 °C 2: water / Cooling with ice 3: neat (no solvent) / 1 h View Scheme

3-hydroxylphthalonitrile (116039-49-7) → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; potassium hydroxide / 90 h / 130 °C 2: 300 °C / Green chemistry View Scheme
Multi-step reaction with 2 steps 1: water / Cooling with ice 2: neat (no solvent) / 1 h View Scheme

1-methoxy-2-ethyl-3-methylbenzene (6161-63-3) → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: cetyltrimethylammonim bromide; potassium permanganate / water / 6.5 h / 80 - 90 °C 2: boron tribromide / dichloromethane / 5 h / 10 - 15 °C 3: dicyclohexyl-carbodiimide / dimethyl sulfoxide / 1 h / 150 °C View Scheme

5-methoxy-1,2,3,4-tetrahydro-naphthalene (1008-19-1) → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: cetyltrimethylammonim bromide; potassium permanganate / dimethyl sulfoxide / 3.17 h / 75 - 90 °C 2: boron tribromide / dichloromethane / 5 h / 10 - 15 °C 3: dicyclohexyl-carbodiimide / dimethyl sulfoxide / 1 h / 150 °C View Scheme

1-methoxy-2-propyl-3-ethylbenzene → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: cetyltrimethylammonim bromide; potassium permanganate / water / 8.5 h / 70 - 90 °C 2: boron tribromide / dichloromethane / 5 h / 10 - 15 °C 3: dicyclohexyl-carbodiimide / dimethyl sulfoxide / 1 h / 150 °C View Scheme

4-methoxy-2,3-dihydro-1H-indene (21573-42-2) → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: cetyltrimethylammonim bromide; potassium permanganate / water / 7.5 h / 70 - 90 °C 2: boron tribromide / dichloromethane / 5 h / 10 - 15 °C 3: dicyclohexyl-carbodiimide / dimethyl sulfoxide / 1 h / 150 °C View Scheme

1-methoxy-2,3-dipropylbenzene → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: cetyltrimethylammonim bromide; potassium permanganate / N,N-dimethyl-formamide / 4.5 h / 70 - 90 °C 2: boron tribromide / dichloromethane / 5 h / 10 - 15 °C 3: dicyclohexyl-carbodiimide / dimethyl sulfoxide / 1 h / 150 °C View Scheme

2,3-dimethylanisole (2944-49-2) → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: cetyltrimethylammonim bromide; potassium permanganate / N,N-dimethyl-formamide / 4.5 h / 70 - 90 °C 2: boron tribromide / dichloromethane / 5 h / 10 - 15 °C 3: dicyclohexyl-carbodiimide / dimethyl sulfoxide / 1 h / 150 °C View Scheme

C13H14O6 → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
With sulfuric acid at -15 - -10℃; for 0.33h;

3-chlorophthalic anhydride (117-21-5) → 3-hydroxyphthalic anhydride (37418-88-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide; copper(l) chloride / water; N,N-dimethyl-formamide / 12 h / 105 °C 2: acetic anhydride / 2 h / 80 °C View Scheme

3-hydroxyphthalic anhydride (37418-88-5) + chloromethyl methyl ether (107-30-2) → 3-methoxymethyloxyphthalic acid anhydride (330192-57-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,1-dichloroethane	99%
With N-ethyl-N,N-diisopropylamine In 1,1-dichloroethane	99%
With N-ethyl-N,N-diisopropylamine In 1,1-dichloroethane	99%

3-hydroxyphthalic anhydride (37418-88-5) + ethanol (64-17-5) → diethyl 3-hydroxyphthalate (24736-82-1)

Conditions	Yield
With sulfuric acid Reflux;	98.7%

3-hydroxyphthalic anhydride (37418-88-5) → (3-hydroxy-1,2-phenylene)dimethanol (7369-27-9)

Conditions	Yield
With borane tetrahydrofuran In tetrahydrofuran for 18h; Heating / reflux;	98%
With lithium aluminium tetrahydride In tetrahydrofuran at -78℃; Reflux;	86%

3-hydroxyphthalic anhydride (37418-88-5) + [(R)-4-amino-4-(3,4-dimethoxyphenyl)butyl]carbamic acid tert-butyl ester (944256-13-7) → C25H30N2O7 (944256-14-8)

Conditions	Yield
With triethylamine In toluene for 24h; Heating / reflux;	98%

3-hydroxyphthalic anhydride (37418-88-5) + [4-amino-4-(3,4-dimethoxyphenyl)butyl]carbamic acid tert-butyl ester (944256-06-8) → [4-(3,4-dimethoxyphenyl)-4-(4-hydroxy-1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)butyl]carbamic acid tert-butyl ester (1190089-46-3)

Conditions	Yield
With triethylamine In toluene for 24h; Reflux;	98%

3-hydroxyphthalic anhydride (37418-88-5) + 3,4-dimethoxybenzylamine (5763-61-1) → 4-hydroxy-2-(3,4-dimethoxybenzyl)-2,3-dihydro-1H-isoindole-1,3-dione (944255-95-2)

Conditions	Yield
With triethylamine In toluene for 24h; Reflux;	96%
With triethylamine In toluene for 24h; Heating / reflux;	96%

3-hydroxyphthalic anhydride (37418-88-5) + rac-α-aminoglutarimide hydrochloride (24666-56-6) → 4-Hydroxythalidomide (5054-59-1)

Conditions	Yield
With potassium acetate In acetic acid for 24h; Reflux;	96%
With sodium acetate; acetic acid at 100℃; for 2h;	96%
With pyridine at 110℃;	93%

3-hydroxyphthalic anhydride (37418-88-5) + 3-phenoxypropanamine (7617-76-7) → 4-hydroxy-2-(3-phenoxypropyl)isoindole-1,3-dione

Conditions	Yield
In toluene for 16h; Heating;	94%

3-hydroxyphthalic anhydride (37418-88-5) + (+/-)-α-aminoglutarimide (2353-44-8) → 4-Hydroxythalidomide (5054-59-1)

Conditions	Yield
With triethylamine In toluene at 110℃; for 12h;	92%
With triethylamine In toluene at 110℃; for 12h;	92%
With sodium acetate; acetic acid for 6h; Reflux;	80%

tyrosamine (51-67-2) + 3-hydroxyphthalic anhydride (37418-88-5) → 4-hydroxy-2-(4-hydroxyphenethyl)isoindoline-1,3-dione (1639899-90-3)

Conditions	Yield
With acetic acid In water at 85℃;	90%
With acetic acid In water Reflux;
With acetic acid In water at 85℃;

3-hydroxyphthalic anhydride (37418-88-5) + 4-Bromophenethylamine (73918-56-6) → 3-hydroxy-N-(p-bromo-phenethyl) phthalimide

Conditions	Yield
With acetic acid In water at 85℃;	90%

3-hydroxyphthalic anhydride (37418-88-5) + 6-amino-1-hexanol (4048-33-3) → C14H17NO4

Conditions	Yield
In toluene at 80 - 135℃;	90%

3-hydroxyphthalic anhydride (37418-88-5) + 3-aminopiperidine-2,6-dione hydrochloric acid salt → 4-Hydroxythalidomide (5054-59-1)

Conditions	Yield
With pyridine at 110℃; for 14h;	88%
With sodium acetate; acetic acid at 110℃; for 10h;	85%
With potassium acetate; acetic acid at 100℃; for 15h; Reagent/catalyst; Temperature;	78.06%
With sodium acetate; acetic acid at 120℃; for 12h;	21%

3-hydroxyphthalic anhydride (37418-88-5) + tert-butyl N-(1-methyl-2,6-dioxopiperidin-3-yl)carbamate → 4-hydroxy-2-(1-methyl-2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione

Conditions	Yield
With 2,2,2-trifluoroethanol at 150℃; for 2h; Microwave irradiation; Sealed tube;	88%
Stage #1: tert-butyl N-(1-methyl-2,6-dioxopiperidin-3-yl)carbamate With trifluoroacetic acid In dichloromethane at 25℃; for 1h; Stage #2: 3-hydroxyphthalic anhydride With acetic anhydride at 140℃; for 6h;	39%

3-hydroxyphthalic anhydride (37418-88-5) + (RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester (31140-42-8) → 4-Hydroxythalidomide (5054-59-1)

Conditions	Yield
With 2,2,2-trifluoroethanol at 150℃; for 2h; Microwave irradiation; Sealed tube;	86%

3-hydroxyphthalic anhydride (37418-88-5) + 3,5-bis-trifluoromethylbenzylamine (85068-29-7) → C17H9F6NO3

Conditions	Yield
In chlorobenzene for 3h; Heating / reflux;	85.2%
In chlorobenzene for 3h; Heating / reflux;	85.2%
In chlorobenzene for 3h; Heating / reflux;	85.2%

3-hydroxyphthalic anhydride (37418-88-5) + diethyl malonate (105-53-3) → diethyl 2-(4-hydroxy-3-oxo-3H-isobenzofuran-1-ylidene)propanedioate

Conditions	Yield
With triethylamine In acetic anhydride at 0 - 40℃;	84.5%

3-hydroxyphthalic anhydride (37418-88-5) + 2-amino-2,3-dihydro-6,7-dimethoxy-1H-isoindol-1-one (1003849-90-8) → 2-[1,3-dihydro-6,7-dimethoxy-1-oxo-2H-isoindol-2-yl]-1H-4-hydroxyisoindole-1,3(2H)-dione (1003851-02-2)

Conditions	Yield
With triethylamine In toluene Heating;	83%

3-hydroxyphthalic anhydride (37418-88-5) + 4-methoxy-benzylamine (2393-23-9) → 4-hydroxy-2-(4-methoxybenzyl)-1H-isoindole-1,3(2H)-dione (491875-13-9)

Conditions	Yield
With acetic acid at 100℃; for 4h;	81%
In acetic acid at 100℃; for 4h;	81%
With acetic acid at 100℃; for 4h;	81%

3-hydroxyphthalic anhydride (37418-88-5) + 1-bromo-octane (111-83-1) → C16H22O5 (1395236-57-3)

Conditions	Yield
With water; silver(l) oxide In acetonitrile at 80℃; for 12h;	80%

3-hydroxyphthalic anhydride (37418-88-5) + (RS)-2,6-dioxopiperidin-3-yl-ammonium trifluoroacetate → 4-Hydroxythalidomide (5054-59-1)

Conditions	Yield
Stage #1: 3-hydroxyphthalic anhydride; (RS)-2,6-dioxopiperidin-3-yl-ammonium trifluoroacetate With triethylamine In tetrahydrofuran for 24h; Inert atmosphere; Reflux; Stage #2: With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 72h; Reflux; Inert atmosphere;	76%
Stage #1: 3-hydroxyphthalic anhydride; (RS)-2,6-dioxopiperidin-3-yl-ammonium trifluoroacetate With triethylamine In tetrahydrofuran for 4h; Reflux; Inert atmosphere; Stage #2: With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 72h; Reflux;	66%
With potassium acetate; acetic acid Reflux;	51%
With pyridine at 20 - 110℃; for 16h;	50%

3-hydroxyphthalic anhydride (37418-88-5) + 2,4-Dimethoxybenzylamine (20781-20-8) → 2-(2,4-dimethoxybenzyl)-4-hydroxyisoindole-1,3-dione (912999-90-7)

Conditions	Yield
With acetic acid at 80℃; for 24h;	73%
In acetic acid at 80℃; for 24h;	73%
With acetic acid at 80℃; for 24h;	73%

3-hydroxyphthalic anhydride (37418-88-5) + 3-aminopiperidine-2,6-dione hydrobromide (90802-45-2) → 4-Hydroxythalidomide (5054-59-1)

Conditions	Yield
Stage #1: 3-hydroxyphthalic anhydride; DL-3-amino-2,6-piperidinone hydrobromide In N,N-dimethyl-formamide at 60℃; for 24h; Stage #2: With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 63℃; for 54h;	71%

3-hydroxyphthalic anhydride (37418-88-5) → 7-hydroxy-1 (3H)-isobenzofuranone (3956-91-0)

Conditions	Yield
With sodium tetrahydroborate	70%
With hydrogen; Λ(+)-tris(pentane-2,5-dionato)ruthenium; TOP; toluene-4-sulfonic acid In various solvent(s) at 200℃; under 22501.8 Torr; for 2h;	60%
Stage #1: 3-hydroxyphthalic anhydride With potassium tri-sec-butyl-borohydride In tetrahydrofuran at -78 - -30℃; Stage #2: With hydrogenchloride In water; ethyl acetate

3-hydroxyphthalic anhydride (37418-88-5) + n-decanoyl chloride (112-13-0) → C18H22O5 (1395236-65-3)

Conditions	Yield
In tetrahydrofuran at 0 - 15℃;	70%

Upstream product

• 117-21-5 3-chlorophthalic anhydride 
• 2944-49-2 2,3-dimethylanisole 
• 21573-42-2 4-methoxy-2,3-dihydro-1H-indene 
• 1008-19-1 5-methoxy-1,2,3,4-tetrahydro-naphthalene 
• 6161-63-3 1-methoxy-2-ethyl-3-methylbenzene 
• 1583-67-1 3-fluorophthalic acid 
• 6937-34-4 3-iodophthalic acid 
• 116-69-8 3-bromophthalic acid 
• 61539-35-3 3-chlorophthalic acid dimethyl ester 
• 27563-65-1 3-chlorobenzene-1,2-dicarboxylic acid 
• 17395-99-2 3-aminophthalic anhydride 
• 641-70-3 3-nitrophthalic acid anhydride 
• 17802-94-7 (2-carboxy-3-methoxy-phenyl)-glyoxylic acid 
• 14963-97-4 3-methoxyphthalic acid 

Downstream Products

• 7369-27-9 (3-hydroxy-1,2-phenylene)dimethanol 
• 1243372-82-8 2-carboxy-3-hydroxy-phenylamide 
• 944255-95-2 4-hydroxy-2-(3,4-dimethoxybenzyl)-2,3-dihydro-1H-isoindole-1,3-dione 
• 1079039-82-9 2-(3,5-dichlorophenyl)-4-hydroxyisoindoline-1,3-dione 
• 1190089-46-3 [4-(3,4-dimethoxyphenyl)-4-(4-hydroxy-1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)butyl]carbamic acid tert-butyl ester 
• 1190089-41-8 C₂₃H₂₆N₂O₇ 
• 1190089-43-0 C₂₄H₂₈N₂O₇ 
• 1190089-49-6 C₂₆H₃₂N₂O₇ 
• 1190089-39-4 C₁₉H₁₉NO₅ 
• 1190089-38-3 C₁₈H₁₇NO₅ 
• 1190089-37-2 C₁₈H₁₇NO₅ 
• 13149-60-5 2-Hydroxy-6-(4-brom-1-hydroxy-2-naphthoyl)-benzoesaeure 
• 13243-91-9 2-(4-Bromo-7-ethyl-1-hydroxy-naphthalene-2-carbonyl)-6-hydroxy-benzoic acid 
• 122447-39-6 triethyl-(1,4-dioxo-2,3-diphenyl-1,2,3,4-tetrahydro-phthalazin-5-yloxycarbonylmethyl)-ammonium; bromide 

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The invention belongs to the field of fine chemical engineering, and particularly relates to a preparation method of herbicide pyriminobac-methyl for a paddy fields. The preparation method comprises the following steps: synthesizing 3-hydroxy phthalic anhydride by using 3-chlorophthalic anhydride as a new raw material, protecting carbonyl by using diethyl malonate, hydrolyzing to obtain 2-acetyl-6-hydroxy benzoic acid, and esterifying to obtain 2-acetyl-6-hydroxy methyl benzoate; then carrying out imidization reaction with methoxyamine hydrochloride to obtain 2-hydroxy-6-(1-methoxy iminoethyl-methyl)-benzoate, and finally, condensing with 2-tosyl-4, 6-dimethoxypyrimidine to obtain pyriminobac-methyl. In the process of preparing pyriminobac-methyl, high-risk reagents such as n-butyllithiumare avoided, a large amount of wastewater generated by diazotization is avoided, the income is increased, and the environment is protected.

DIMERIC IMMUNO-MODULATORY COMPOUNDS AGAINST CEREBLON-BASED MECHANISMS

Disclosed are small molecules against cereblon to enhance effector T cell function. Methods of making these molecules and methods of using them to treat various disease states are also disclosed.

OLIGONUCLEOTIDE-BASED PROTEOLYSIS TARGETING CHIMERA

Disclosed herein, inter alia, are oligonucleotide-based proteolysis targeting chimeras and methods of use thereof.