6943-97-1

Basic information

• Product Name: 1-(3-bromopropyl)-3-methoxybenzene
• Synonyms: Anisole, m-(3-bromopropyl)-; Anisole, m-(3-bromopropyl)-
• CAS NO: 6943-97-1
• Molecular Formula: C₁₀H₁₃BrO
• Molecular Weight: 229.1136
• Mol File: 6943-97-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 267.6°C at 760 mmHg
• Flash Point: 106°C
• Density: 1.302g/cm³
• Vapor Pressure: 0.0133mmHg at 25°C
• Refractive Index: 1.535
• CAS DataBase Reference: 1-(3-bromopropyl)-3-methoxybenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-bromopropyl)-3-methoxybenzene(6943-97-1)
• EPA Substance Registry System: 1-(3-bromopropyl)-3-methoxybenzene(6943-97-1)

Safety Data

• Hazardous Substances Data: 6943-97-1(Hazardous Substances Data)

Usage

General Description

1-(3-bromopropyl)-3-methoxybenzene is a chemical compound with the molecular formula C10H13BrO. It is an aromatic compound that consists of a benzene ring substituted with a methoxy group and a bromopropyl group. The bromopropyl group is attached to the benzene ring at the first position, and the methoxy group is attached to the third position. 1-(3-bromopropyl)-3-methoxybenzene is commonly used in organic synthesis as a building block for the preparation of various organic compounds. It is important to handle this compound with caution, as bromine-containing compounds can be toxic and irritating to the skin, eyes, and respiratory system.

Synthetic route

3-(3-bromopropyl)phenol (1971-83-1) + methyl iodide (74-88-4) → (m-methoxyphenyl)propyl bromide (6943-97-1)

Conditions	Yield
With potassium carbonate In acetone for 12h; Heating;	88%

3-(3-methoxyphenyl)propan-1-ol (7252-82-6) → (m-methoxyphenyl)propyl bromide (6943-97-1)

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In diethyl ether reflux, 1 h, 2 h, 15 h;	77%
With phosphorus tribromide In diethyl ether for 1h; Heating;	71%
With phosphorus tribromide In benzene for 5h; Ambient temperature;	66%

1-bromomethyl-3-methoxybenzene (874-98-6) → (m-methoxyphenyl)propyl bromide (6943-97-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) Mg, 1,2-dibromoethane / 1.) ether, reflux, 1 h; 2.) ether, RT, 24 h 2: PBr3, pyridine / benzene / 24 h / Ambient temperature View Scheme

ethyl 3-<3-(benzyloxy)phenyl>propanoate (75849-10-4) → (m-methoxyphenyl)propyl bromide (6943-97-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / LiAlH4 / diethyl ether / 1 h / Heating 2: 36 percent / PBr3 / diethyl ether / 21 h / Ambient temperature 3: 88 percent / K2CO3 / acetone / 12 h / Heating View Scheme

3-[3-(Benzyloxy)phenyl]-1-propanol (57668-35-6) → (m-methoxyphenyl)propyl bromide (6943-97-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 36 percent / PBr3 / diethyl ether / 21 h / Ambient temperature 2: 88 percent / K2CO3 / acetone / 12 h / Heating View Scheme

3-(3-Methoxy-phenyl)-propionic acid (10516-71-9) → (m-methoxyphenyl)propyl bromide (6943-97-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / LiAlH4 / tetrahydrofuran / brisk reflux, 40 min, reflux, 15 h 2: 77 percent / tetrabromomethane, triphenylphosphine / diethyl ether / reflux, 1 h, 2 h, 15 h View Scheme
Multi-step reaction with 2 steps 1: 97 percent / LiAlH4 / tetrahydrofuran / 3 h / Ambient temperature 2: 71 percent / PBr3 / diethyl ether / 1 h / Heating View Scheme
Multi-step reaction with 2 steps 1: LiAlH4 2: PBr3 View Scheme

3-methoxycinnamic acid (6099-04-3) → (m-methoxyphenyl)propyl bromide (6943-97-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / H2 / 7percent Pd-C / ethanol / 1 h / Ambient temperature 2: 97 percent / LiAlH4 / tetrahydrofuran / 3 h / Ambient temperature 3: 71 percent / PBr3 / diethyl ether / 1 h / Heating View Scheme
Multi-step reaction with 3 steps 1: H2 / PtO2 2: LiAlH4 3: PBr3 View Scheme

3-methoxy-benzaldehyde (591-31-1) → (m-methoxyphenyl)propyl bromide (6943-97-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 98 percent / piperidine / pyridine / 1.) 85 deg C, 1 h, 2.) 115 deg C, 3 h 2: 88 percent / H2 / 7percent Pd-C / ethanol / 1 h / Ambient temperature 3: 97 percent / LiAlH4 / tetrahydrofuran / 3 h / Ambient temperature 4: 71 percent / PBr3 / diethyl ether / 1 h / Heating View Scheme

3-(3-methoxyphenyl)propan-1-ol (7252-82-6) + allyl bromide (106-95-6) → (m-methoxyphenyl)propyl bromide (6943-97-1)

Conditions	Yield
With 1,1'-carbonyldiimidazole In acetonitrile

Methyl formate (107-31-3) + (m-methoxyphenyl)propyl bromide (6943-97-1) → 1,7-bis(3-methoxyphenyl)heptan-4-ol (1071768-09-6)

Conditions	Yield
Stage #1: (m-methoxyphenyl)propyl bromide With magnesium Grignard reaction; Stage #2: Methyl formate In tetrahydrofuran at 20℃; Grignard reaction; Further stages.;	85%

(m-methoxyphenyl)propyl bromide (6943-97-1) + potassium cyanide (151-50-8) → 3-(3'-methoxyphenyl)-1-butyronitrile (91152-85-1)

Conditions	Yield
In dimethyl sulfoxide at 85℃; for 16h;	80%

(m-methoxyphenyl)propyl bromide (6943-97-1) + dimethyl amine (124-40-3) → 3-(3-methoxyphenyl)-N,N-dimethylpropan-1-amine (77318-04-8)

Conditions	Yield
In ethanol for 5h; Heating;	75%

(2E,4E-hexadienal)iron tricarbonyl (34872-46-3, 12125-70-1, 34872-45-2, 32699-34-6) + (m-methoxyphenyl)propyl bromide (6943-97-1) → (2R*,6R*)-tricarbonyl[2-5-η4-(2E,4E)-9-(3-methoxyphenyl)nonadien-6-ol]iron + Fe(CO)3C5H7CHOH(CH2)3C6H4OCH3

Conditions

Yield

With iodine; magnesium In tetrahydrofuran to Mg in THF contg. I2 was added dropwise at reflux soln. of ligand in THF, stirred at reflux for 1 h, soln. of Fe-complex in THF was added at -78°C, stirred at -78°C for 30 min and at room temp. for 30min, quenched with aq. NH4Cl; THF was removed, aq. layer extd. with Et2O, washed with NaHCO3, water, dried over Na2SO4, solvent was removed under vac., flash chromy. on silica gel with EtOAc-hexane;

A 51% B 35%

(m-methoxyphenyl)propyl bromide (6943-97-1) + 2-(2-bromophenyl)-2-methylpropionaldehyde (212626-89-6) → C10H13LiO

Conditions	Yield
Stage #1: (m-methoxyphenyl)propyl bromide With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 1h; Stage #2: 2-(2-bromophenyl)-2-methylpropionaldehyde In diethyl ether; pentane at -78 - -30℃; for 1.5h;	44%

(m-methoxyphenyl)propyl bromide (6943-97-1) + [(E)-methyl 3-(2-oxo-1,2-dihydropyridin-3-yl)acrylate] → (E)-methyl 3-(1-(3-(3-methoxyphenyl)propyl)-2-oxo-1,2-dihydropyridin-3-yl)acrylate

Conditions	Yield
With potassium carbonate In acetone Reflux;	42%

(m-methoxyphenyl)propyl bromide (6943-97-1) → 3-(3-methoxyphenyl)propane-1-sulfonamide

Conditions	Yield
Stage #1: (m-methoxyphenyl)propyl bromide With rongalite In dimethyl sulfoxide at 25℃; for 18h; Schlenk technique; Inert atmosphere; Stage #2: With sodium acetate; hydroxylamine-O-sulfonic acid In water; dimethyl sulfoxide at 25℃; for 12h; Schlenk technique; Inert atmosphere;	32%

1,3 dithiane (505-23-7) + (m-methoxyphenyl)propyl bromide (6943-97-1) → 2-(3-m-methoxyphenylpropyl)-1,3-dithian (129225-94-1)

Conditions	Yield
With n-butyllithium 1.) hexane, THF, -78 deg C, 1 h, 2.) -78 deg C, 2 h; Yield given. Multistep reaction;

tetrahydropyrrolo[1,2-c]imidazol-1,3-dione (5768-79-6) + (m-methoxyphenyl)propyl bromide (6943-97-1) → 3-<3-(m-methoxyphenyl)propyl>-1,3-diazabicyclo<3.3.0>octane-2,4-dione (92763-94-5)

Conditions	Yield
With potassium hydroxide 1) DMSO, 100-110 deg C, 1 h 2) 70-80 deg C, 10 h then r.t., 2 d; Yield given. Multistep reaction;

4-tetrahydropyranyloxybutanal (54911-85-2) + (m-methoxyphenyl)propyl bromide (6943-97-1) → 7-(3-methoxyphenyl)-4-hydroxyheptyl tetrahydropyranyl ether

Conditions	Yield
With magnesium 1.) ether; 2.) ether; Yield given. Multistep reaction;

4-methoxyphenyl benzyl ketone (1023-17-2) + (m-methoxyphenyl)propyl bromide (6943-97-1) → 1-(p-Methoxyphenyl)-5-(m-methoxyphenyl)-2-phenyl-1-pentanone (109610-53-9)

Conditions	Yield
With sodium hydride 1.) DMF, 40-50 deg C, 30 min, 2.) DMF, r.t., 2 h; Yield given. Multistep reaction;

(m-methoxyphenyl)propyl bromide (6943-97-1) + 1-methoxy-4-methylbicyclo<2.2.2>oct-5-ene-2-carbaldehyde (134354-09-9) → 1-(1-methoxy-4-methylbicyclo<2.2.2>oct-5-en-2-yl)-4-(3-methoxyphenyl)butan-1-ol (134329-64-9)

Conditions	Yield
With magnesium 1.) ether, 2.) THF, ether, RT, overnight; Yield given. Multistep reaction;

(m-methoxyphenyl)propyl bromide (6943-97-1) + 1-methoxy-4-methylbicyclo<2.2.2>oct-5-ene-2-carbonitrile (139437-11-9, 139559-93-6) → 1-(1-methoxy-4-methylbicyclo<2.2.2>oct-5-en-2-yl)-4-(3-methoxyphenyl)butan-1-one (134329-65-0)

Conditions	Yield
With magnesium 1.) ether, 2.) benzene, a) 8 h, b) reflux, 2 h; Yield given. Multistep reaction;

(m-methoxyphenyl)propyl bromide (6943-97-1) + Lithium; 1-methoxy-4-methyl-bicyclo[2.2.2]oct-5-ene-2-carboxylate → 1-(1-methoxy-4-methylbicyclo<2.2.2>oct-5-en-2-yl)-4-(3-methoxyphenyl)butan-1-one (134329-65-0)

Conditions	Yield
With n-butyllithium 1.) ether, 2.) diglyme, ether, overnight; Yield given. Multistep reaction;

(m-methoxyphenyl)propyl bromide (6943-97-1) + 5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) → 3-<3-(3-methoxyphenyl)propyl>-5,5-dimethyl-2,4-imidazolidinedione (81572-15-8)

Conditions	Yield
With potassium hydroxide 1.) Me2SO, 100-110 deg C, 1 h, 2a.) RT, 2 d, 2b.) 70 deg C, 5 h; Yield given. Multistep reaction;

(m-methoxyphenyl)propyl bromide (6943-97-1) + phenylacetonitrile (140-29-4) → 5-(m-Methoxyphenyl)-2-phenylpentonitrile (109610-54-0)

Conditions	Yield
With sodium hydride 1.) DMF, 40-50 deg C, 30 min, 2.) DMF, r.t., 3 h; Yield given. Multistep reaction;

(m-methoxyphenyl)propyl bromide (6943-97-1) + 4-methoxy-benzaldehyde (123-11-5) → 1-(4-methoxyphenyl)-4-(3-methoxyphenyl)butan-1-ol (73087-65-7)

Conditions	Yield
With ethyl bromide; iodine; magnesium 1) Et2O, room temp., 1 h; 2) room temp., 12 h; Yield given. Multistep reaction;

(m-methoxyphenyl)propyl bromide (6943-97-1) + thiophenol (108-98-5) → 3-(m-methoxyphenyl)-1-phenylthiopropane (129169-39-7)

Conditions	Yield
With sodium hydride 1) DMF, 1 h 2) r.t., 90 min; Yield given. Multistep reaction;

(m-methoxyphenyl)propyl bromide (6943-97-1) + ortho-anisaldehyde (135-02-4) → 1-(2-methoxyphenyl)-4-(3-methoxyphenyl)butan-1-ol (75849-13-7)

Conditions	Yield
With ethyl bromide; iodine; magnesium 1) Et2O, room temp., 1 h; 2) room temp., 12 h; Yield given. Multistep reaction;

(m-methoxyphenyl)propyl bromide (6943-97-1) + acetone (67-64-1) → 3-methoxy-α,α-dimethylbenzenebutanol (156868-20-1)

Conditions	Yield
With magnesium; ethylene dibromide 1.) ether, reflux, 1 h; 2.) ether, RT, 24 h; Yield given. Multistep reaction;

(m-methoxyphenyl)propyl bromide (6943-97-1) + acrolein (107-02-8) → 6-(3-methoxyphenyl)hex-1-en-3-ol (408523-53-5)

Conditions	Yield
In diethyl ether for 1h;

(m-methoxyphenyl)propyl bromide (6943-97-1) + methyl-5 hydantoine (67337-69-3) → 3-<3-(m-methoxyphenyl)propyl>-5-methylimidazolidine-2,4-dione (92763-90-1)

Conditions	Yield
With potassium hydroxide 1) DMSO, 100 to 110 deg C, 1 h 2) DMSO, r.t., 2 d; Yield given. Multistep reaction;

(m-methoxyphenyl)propyl bromide (6943-97-1) + benzeneacetic acid methyl ester (101-41-7) → 3-(m-Methoxyphenyl)propyl phenylacetate (109610-52-8)

Conditions	Yield
With sodium hydride 1.) DMF, 50 deg C, 30 min, 2.) DMF, r.t., overnight; Yield given. Multistep reaction;

(m-methoxyphenyl)propyl bromide (6943-97-1) + triphenylphosphine (603-35-0) → 3-(3-methoxyphenyl)propyl-triphenyl phosphonium bromide (28437-33-4)

Conditions	Yield
In toluene at 120℃;

(m-methoxyphenyl)propyl bromide (6943-97-1) + sodium acetylide (1066-26-8) → 1-(4-pentynyl)-3-methoxybenzene (1424-70-0)

Conditions	Yield
With ammonia

(m-methoxyphenyl)propyl bromide (6943-97-1) + 1,5-dimethoxy-1,4-cyclohexadiene (37567-78-5) → 1-[3-(2,6-dimethoxy-cyclohexa-2,5-dienyl)-propyl]-3-methoxy-benzene

Conditions	Yield
Stage #1: 1,5-dimethoxy-1,4-cyclohexadiene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Metallation; Stage #2: (m-methoxyphenyl)propyl bromide With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran; pentane at -78 - 20℃; Alkylation;

(m-methoxyphenyl)propyl bromide (6943-97-1) → 2-[3-(3'-methoxyphenyl)propyl]-1,3-cyclohexanedione (327621-55-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: t-BuLi / pentane; tetrahydrofuran / 1 h / -78 °C 1.2: HMPA / pentane; tetrahydrofuran / -78 - 20 °C 2.1: aq. HCl / acetone View Scheme

Upstream product

• 7252-82-6 3-(3-methoxyphenyl)propan-1-ol 
• 10516-71-9 3-(3-Methoxy-phenyl)-propionic acid 
• 106-95-6 allyl bromide 
• 591-31-1 3-methoxy-benzaldehyde 
• 6099-04-3 3-methoxycinnamic acid 
• 57668-35-6 3-[3-(Benzyloxy)phenyl]-1-propanol 
• 75849-10-4 ethyl 3-<3-(benzyloxy)phenyl>propanoate 
• 874-98-6 1-bromomethyl-3-methoxybenzene 
• 1971-83-1 3-(3-bromopropyl)phenol 
• 74-88-4 methyl iodide 

Downstream Products

• 92763-94-5 3-<3-(m-methoxyphenyl)propyl>-1,3-diazabicyclo<3.3.0>octane-2,4-dione 
• 134329-64-9 1-(1-methoxy-4-methylbicyclo<2.2.2>oct-5-en-2-yl)-4-(3-methoxyphenyl)butan-1-ol 
• 91152-85-1 3-(3'-methoxyphenyl)-1-butyronitrile 
• 134329-65-0 1-(1-methoxy-4-methylbicyclo<2.2.2>oct-5-en-2-yl)-4-(3-methoxyphenyl)butan-1-one 
• 109610-54-0 5-(m-Methoxyphenyl)-2-phenylpentonitrile 
• 73087-65-7 1-(4-methoxyphenyl)-4-(3-methoxyphenyl)butan-1-ol 
• 408523-53-5 6-(3-methoxyphenyl)hex-1-en-3-ol 
• 109610-52-8 3-(m-Methoxyphenyl)propyl phenylacetate 
• 28437-33-4 3-(3-methoxyphenyl)propyl-triphenyl phosphonium bromide 
• 112778-17-3 7-(3-methoxyphenyl)heptane-1,4-diol 
• 1257335-48-0 (E)-N-hydroxy-3-(1-(3-(3-methoxyphenyl)propyl)-2-oxo-1,2-dihydropyridin-3-yl)acrylamide 
• 1424-70-0 1-(4-pentynyl)-3-methoxybenzene 
• 75849-13-7 1-(2-methoxyphenyl)-4-(3-methoxyphenyl)butan-1-ol 
• 77318-04-8 3-(3-methoxyphenyl)-N,N-dimethylpropan-1-amine 

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