64169-34-2

Basic information

• Product Name: 5-Bromophthalide
• Synonyms: 5-BROMO-1(3H)-ISOBENZOFURANONE;5-BROMO-3H-ISOBENZOFURANONE;5-BROMO-2-BENZOFURAN-(3H)-ONE;5-BROMOPHTHALIDE;5-Bromo-1-isobenzofuranone;5-Bromophthalide99%MIN.;5-Bromophthalide,98%;5-bromo-3H-isobenzofuran-1-one
• CAS NO: 64169-34-2
• Molecular Formula: C₈H₅BrO₂
• Molecular Weight: 213.03
• EINECS: 447-190-5
• Product Categories: Phthalides;INTERMEDIATESOFCITALOPRAM;Miscellaneous Reagents;Aromatics
• Mol File: 64169-34-2.mol
• Article Data: 37

Chemical Properties

• Melting Point: 162-166 °C(lit.)
• Boiling Point: 377.7 °C at 760 mmHg
• Flash Point: 182.2 °C
• Appearance: Beige to light yellow/Crystalline Powder
• Density: 1.742 g/cm³
• Vapor Pressure: 6.63E-06mmHg at 25°C
• Refractive Index: 1.625
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Soluble in acetone.
• CAS DataBase Reference: 5-Bromophthalide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromophthalide(64169-34-2)
• EPA Substance Registry System: 5-Bromophthalide(64169-34-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 2
• RTECS: EJ9940000
• Hazardous Substances Data: 64169-34-2(Hazardous Substances Data)

Usage

Chemical Properties

5-Bromophthalide is white to Pale Yellow Crystalline Solid

Uses

Different sources of media describe the Uses of 64169-34-2 differently. You can refer to the following data:
1. 5-Bromophthalide is an important organic intermediate. It can be used in agrochemical, pharmaceutical and dyestuff field. It is a key intermediate of citalopram.
2. 5-Bromophthalide is a useful synthetic intermediate

InChI:InChI=1/C8H5BrO2/c9-6-1-2-7-5(3-6)4-11-8(7)10/h1-3H,4H2

Upstream product

• 86-90-8 4-bromophthalic anhydride 
• 65399-05-5 5-amino-3H-isobenzofuran-1-one 
• 586-76-5 4-Bromobenzoic acid 
• 74-95-3 1,1-dibromomethane 
• 220513-49-5 5-bromo-1,3-dihydroisobenzofuran 
• 87-41-2 2-benzofuran-1(3H)-one 
• 38568-41-1 diethyl 4-bromophthalate 
• 171011-37-3 4-bromo-2-(hydroxymethyl)benzyl alcohol 
• 89-40-7 4-nitrophthalimide 
• 3676-85-5 4-aminophthalimide 
• 136918-14-4 phthalimide 
• 68837-59-2 4-bromo-2-methylbenzoic acid 
• 1467-79-4 NCNMe₂ 
• 888030-82-8 (5-bromo-3H-isobenzofuran-1-ylidene)-isopropyl-amine 

Downstream Products

• 64169-66-0 5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran 
• 64169-65-9 4-bromo-(2-hydroxymethyl)-phenyl-(4'-fluorophenyl)methanol 
• 488148-10-3 4-(4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzobromide 
• 508169-73-1 (4-bromo-2-hydroxyethyl) phenyl-(4-fluorophenyl)-(3-dimethylaminopropyl) methanol hydrochloride 
• 1236409-37-2 2-[4-bromo-2-(hydroxymethyl)phenyl]propan-2-ol 
• 64169-67-1 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile 
• 59729-33-8 1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile 
• 1374261-51-4 5-{3-[4-(1-aminocyclobutyl)phenyl]-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-2-yl}-2-benzofuran-1(3H)-one 
• 1449517-44-5 2-oxopropyl 5-bromo-2-formylbenzoate 
• 4785-52-8 5-bromo-ortho-formylbenzoic acid 
• 1464157-79-6 (4-bromo-2-(hydroxymethyl)phenyl)(morpholino)methanone 
• 1464157-82-1 2-(5-bromo-2-(morpholine-4-carbonyl)benzyl)isoindoline-1,3-dione 
• 1464152-40-6 4-(6-(3-((1,3-dioxoisoindolin-2-yl)methyl)-4-(morpholine-4-carbonyl)phenyl)imidazo[1,2-a]pyridin-3-yl)benzonitrile 
• 1256845-46-1 4-bromo-2-((tert-butyldimethylsilyloxy)methyl)benzoic acid 

Relevant articles and documents

Design, synthesis and biological evaluation of novel thiohydantoin derivatives as potent androgen receptor antagonists for the treatment of prostate cancer

Prostate cancer (PC) is the most common malignancy in men worldwide. Here, two series of novel thiohydantoin derivatives of enzalutamide as potent androgen receptor (AR) antagonists were designed and synthesized. Among them, compound 31c was identified as an AR antagonist which is 2.3–fold more potent than enzalutamide. Molecular docking studies were performed to explain the improved potency of 31c at AR. In cell proliferation assays, 31c exhibited similar anti-proliferative activities with enzalutamide against hormone sensitive LNCaP cells and AR-overexpressing LNCaP/AR cells. These data indicate that 31c can be a good lead compound for further structure optimization for the treatment of prostate cancer.

Visible Light-Promoted Magnesium, Iron, and Nickel Catalysis Enabling C(sp3)-H Lactonization of 2-Alkylbenzoic Acids

A mild and practical C(sp3)-H lactonization protocol has been achieved by merging photocatalysis and magnesium (iron, nickel) catalysis. A diverse range of 2-alkylbenzoic acids with a variety of substitution patterns could be transformed into the corresponding phthalide products. Based on the mechanistic experimentation and reported prior studies, a possible mechanism for the benzylic oxidative lactonization reaction was proposed with the hypothetic photoactive ternary complex formed between the 2-alkylbenzoic acid substrate, magnesium ion, and bromate anion.

Enantioselective synthesis of 3-aryl-phthalides through a nickel-catalyzed stereoconvergent cross-coupling reaction

A nickel-catalyzed asymmetric Suzuki-Miyaura cross-coupling of racemic 3-bromo-phthalides and arylboronic acids was realized for the synthesis of diverse chiral 3-aryl-phthalides in moderate to excellent reaction yields. The reaction proceeded in a stereoconvergent manner and high enantioselectivities were observed for most examined examples. A number of functional groups like aldehyde, ester and bromide were well tolerated. Heteroaromatic boronic acids were also competent coupling partners in this reaction.