102292-30-8

Basic information

• Product Name: 5-bromo-2-methyl-2,3-dihydro-1-benzofuran
• Synonyms: 5-Bromo-2-methyl-2,3-dihydro-1-benzofuran; benzofuran, 5-bromo-2,3-dihydro-2-methyl-
• CAS NO: 102292-30-8
• Molecular Formula: C₉H₉BrO
• Molecular Weight: 213.0712
• Mol File: 102292-30-8.mol

Chemical Properties

• Boiling Point: 257.3°C at 760 mmHg
• Flash Point: 101.9°C
• Density: 1.461g/cm³
• Vapor Pressure: 0.0236mmHg at 25°C
• Refractive Index: 1.57
• CAS DataBase Reference: 5-bromo-2-methyl-2,3-dihydro-1-benzofuran(CAS DataBase Reference)
• NIST Chemistry Reference: 5-bromo-2-methyl-2,3-dihydro-1-benzofuran(102292-30-8)
• EPA Substance Registry System: 5-bromo-2-methyl-2,3-dihydro-1-benzofuran(102292-30-8)

Safety Data

• Hazardous Substances Data: 102292-30-8(Hazardous Substances Data)

Upstream product

• 25244-30-8 4-(allyloxy)bromobenzene 
• 1746-11-8 2-methyl-2,3-dihydro-1-benzofuran 
• 1745-81-9 o-Allylphenol 
• 56-23-5 tetrachloromethane 
• 57083-30-4 acetic acid-(2-allyl-4-bromo-phenyl ester) 
• 123-31-9 hydroquinone 
• 13997-74-5 2-allyl-4-bromophenol 
• 3698-28-0 2-allylanisole 

Relevant articles and documents

ACETYLATION, BROMINATION, AND NITRATION OF BENZOXAHETEROCYCLES AND SYNTHESIS OF β-AMINOKETONES FROM ACETYL DERIVATIVES

The method of competing reactions was used to establish the sequence of variation of the relative rates of acetylation, bromination, and nitration reactions of 2-methylcoumaran, chroman, 2,3,4,5-tetrahydrobenzo-1-oxepan, and 1-methoxy-2-ethylbenzene.The i

Dihydrobenzofuran production from catalytic tandem Claisen rearrangement-intramolecular hydroaryloxylation of allyl phenyl ethers in subcritical water

We herein report a mild method for the preparation of dihydrobenzofurans through hydrothermal catalytic tandem Claisen rearrangement-intramolecular hydroaryloxylation of allyl phenyl ethers. This reaction provides a new method for constructing dihydrobenzofurans, a process that is potentially applicable to natural product synthesis. SBA-15, TS-1, HZSM-5 were chosen as catalysts in a hydrothermal reaction medium between 200 and 320 °C. HZSM-5 catalyst showed the highest catalytic activity, and the effects of molar ratio of allyl phenyl ether-water, time, pressure, temperature and catalyst on the Claisen hydroaryloxylation in hydrothermal condition were investigated. The latter two process variables had the greatest influence on the product yields and distribution. A series of allyl phenyl ether derivatives were also treated in hydrothermal condition with HZSM-5 catalyst to offer high yield of corresponding dihydrobenzofurans.

Investigation and mechanistic study into intramolecular hydroalkoxylation of unactivated alkenols catalyzed by cationic lanthanide complexes

Cationic lanthanide complexes of the type [Ln(CH3CN)9]3+[(AlCl4)3]3–·CH3CN (Ln = Pr, Nd, Sm, Gd, Er, Yb, Y) served as effective catalysts for the intramolecular hydroalkoxylation/cyclization of unactivated alkenols to yield the cyclic ethers with Markovnikov regioselectivity under mild conditions. Novel cationic complexes, [AlCl(CH3CN)5]2+[(AlCl4)2]2–·CH3CN and [Nd(CH3CN)9]3+[(FeCl4)3]3–·CH3CN, were synthesized and evaluated for the intramolecular hydroalkoxylation/cyclization of unactivated alkenols for comparison. The active sequence of [Nd(CH3CN)9]3+[(FeCl4)3]3–·CH3CN 3CN)5]2+[(AlCl4)2]2–·CH3CN 3CN)9]3+[(AlCl4)3]3–·CH3CN observed indicated that both the cation and anion have great influence on the activity. Comparative study on the activity of AlCl3and its cationic complex [AlCl(CH3CN)5]2+[(AlCl4)2]2–·CH3CN revealed the formation of the cationic Al center enhanced the activity greatly. The1H NMR studies indicated the activation of hydroxyl and olefin by the cationic Ln3+center were involved in the reaction pathways.

Fused N-phenylsulfonyl-N'-pyrimidinylureas and N-phenylsulfonyl-N'triazinylureas

The invention relates to N-phenylsulfonyl-N'-pyrimidinylureas and N-phenylsulfonyl-N-triazinylureas of the general formula STR1 wherein Z is oxygen or sulfur, E is nitrogen or =CH--, R1 is hydrogen, halogen, nitro, C1 -C4 alkyl, C1 -C4 haloalkyl, C1 -C4 alkoxy, C1 -C4 haloalkoxy, C1 -C4 alkoxycarbonyl, C1 -C4 alkylthio, C1 -C4 alkylsulfinyl, C1 -C4 alkylsulfonyl or C2 -C5 alkoxyalkoxy, R2 is hydrogen, C1 -C4 alkyl or C1 -C3 alkoxy, R3 and R4, each independently of the other, are hydrogen, C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 haloalkoxy, C1 -C4 haloalkylthio, C1 -C4 alkylthio, halogen, C2 -C5 alkoxyalkyl, C2 -C5 alkoxyalkoxy or --NR5 R6, wherein R5 and R6 are hydrogen or C1 -C4 alkyl, and A is an unsubstituted or substituted bridge of 3 or 4 atoms which contains 1 or 2 oxygen, sulfur or nitrogen atoms and, together with the linking carbon atom, forms a non-aromatic 5- or 6-membered heterocyclic ring system, with the proviso that two oxygen atoms are separated by at least one carbon atom and that oxygen and sulfur atoms are only linked to each other if the sulfur atom takes the form of the --SO-- or --SO2 -- group; and to the salts of these compounds with amines, alkali metal bases or alkaline earth metal bases or with quaternary ammonium bases. These compounds have good pre- and postemergence selective herbicidal and growth regulating properties.

Process for the preparation of 1,2-benzoxathiine derivatives

A novel process for the preparation of 3,4-dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide of the formula I STR1 reacting a 5-halo-2,3-dihydro-2-methylbenzo[b]furan of the formula II STR2 wherein Hal is chlorine or bromine, with chlorosulfonic acid to give a 6-halo-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonyl chloride of formula III STR3 wherein Hal is chlorine or bromine, converting this sulfonyl chloride with ammonia into a 6-halo-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide of formula IV STR4 wherein Hal is chlorine or bromine, dehalogenating this sulfonamide with hydrogen in the presence of a tertiary amine and a noble metal catalyst, and hydrogenating the resultant 2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide of formula V STR5 with hydrogen in the presence of a noble metal catalyst.

Process for the preparation of 1,2-benzoxathiines

1,2-Benzoxathiine derivatives of the formula I STR1 wherein Hal is chlorine, bromine or iodine, R is hydrogen, halogen, nitro, C1 -C4 alkyl, C1 -C4 haloalkyl, cyano or a --X--R1, --CO--X--R2, --CO--NR3 R4, --SO--R5 or --SO2 --R6 group, where R1 is C3 -C5 alkynyl, or is C1 -C4 alkyl, unsubstituted or substituted by halogen or C1 -C4 alkoxy, or is C3 -C5 alkenyl, unsubstituted or substituted by halogen or C1 -C4 alkoxy, R2 and R5 are each independently of the other C1 -C4 alkyl,-C1 -C4 haloalkyl, C2 -C4 alkoxyalkyl, C3 -C5 alkenyl, C3 -C5 alkynyl, phenyl or benzyl, R3 and R4 are each independently of the other hydrogen, C1 -C4 alkyl, C1 -C4 haloalkyl, C2 -C4 alkoxyalkyl, C3 -C5 alkenyl, C3 -C5 alkynyl, phenyl or benzyl, R6 is C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 haloalkoxy or --NR7 R8, R7 and R8 are each independently of the other hydrogen, C1 -C4 alkyl, C1 -C4 haloalkyl, C2 -C4 alkoxyalkyl, C3 -C5 alkenyl, C3 -C5 alkynyl, phenyl or benzyl, and X is oxygen or sulfur, are obtained by treating a dihydrobenzofuran derivative of formula II STR2 with chlorosulfonic acid of the formula ClSO3 H.