3-Methoxybenzyl chloride
- Product Name
- 3-Methoxybenzyl chloride
- CAS No.
- 824-98-6
- Chemical Name
- 3-Methoxybenzyl chloride
- Synonyms
- AKOS BBS-00003862;3-Methoxybenzyl chlo;3-CHLOROMETHYLANISOLE;3-methoxychlorobenzyl;m-(Chloromethyl)anisole;3-Methoxybenzalchloride;3-METHOXYBENZYL CHLORIDE;M-METHOXYBENZYL CHLORIDE;a-Chloro-m-methoxytoluene;META-(CHLOROMETHYL)ANISOL
- CBNumber
- CB5477445
- Molecular Formula
- C8H9ClO
- Formula Weight
- 156.61
- MOL File
- 824-98-6.mol
3-Methoxybenzyl chloride Property
- Melting point:
- 101.67°C
- Boiling point:
- 124 °C13 mm Hg(lit.)
- Density
- 1.078 g/mL at 25 °C(lit.)
- refractive index
- n20/D 1.544(lit.)
- Flash point:
- 215 °F
- storage temp.
- 2-8°C
- solubility
- Chloroform, Methanol (Slightly)
- form
- clear liquid
- color
- Colorless to Light yellow
- Specific Gravity
- 1.157 (20/4℃)
- Sensitive
- Moisture Sensitive
- BRN
- 636684
- InChIKey
- VGISFWWEOGVMED-UHFFFAOYSA-N
- CAS DataBase Reference
- 824-98-6(CAS DataBase Reference)
- NIST Chemistry Reference
- «alpha»-Chloro-3-methoxytoluene(824-98-6)
Safety
- Hazard Codes
- C
- Risk Statements
- 34
- Safety Statements
- 26-36/37/39-45
- RIDADR
- UN 3265 8/PG 2
- WGK Germany
- 1
- F
- 19-21
- HazardClass
- 8
- PackingGroup
- III
- HS Code
- 29093090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H314Causes severe skin burns and eye damage
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P363Wash contaminated clothing before reuse.
N-Bromosuccinimide Price
- Product number
- 209384
- Product name
- 3-Methoxybenzyl chloride
- Purity
- 97%
- Packaging
- 5g
- Price
- $12.3
- Updated
- 2025/07/31
- Product number
- 209384
- Product name
- 3-Methoxybenzyl chloride
- Purity
- 97%
- Packaging
- 25g
- Price
- $65.1
- Updated
- 2025/07/31
- Product number
- M0820
- Product name
- 3-Methoxybenzyl Chloride
- Purity
- >96.0%(GC)
- Packaging
- 5g
- Price
- $30
- Updated
- 2025/07/31
- Product number
- M0820
- Product name
- 3-Methoxybenzyl Chloride
- Purity
- >96.0%(GC)
- Packaging
- 25g
- Price
- $86
- Updated
- 2025/07/31
- Product number
- M261160
- Product name
- 3-Methoxybenzyl chloride
- Packaging
- 1g
- Price
- $120
- Updated
- 2021/12/16
3-Methoxybenzyl chloride Chemical Properties,Usage,Production
Chemical Properties
clear colorless to light yellow liquid
Uses
3-Methoxybenzyl chloride was used to alkylate 8-benzyloxy-2(1H)-quinolinone in the presence of DMF and NaH. It was also used in the synthesis of diarylmethanes via in situ organozinc-mediated, palladium-catalyzed cross-coupling between benzyl and aryl halide.
Application
3-Methoxybenzyl chloride is used for protection of alcohols, thiols, phenols, amides, amines, and carboxylic acids.
Synthesis
6971-51-3
824-98-6
General procedure for the synthesis of 3-methoxybenzyl chloride from m-methoxybenzyl alcohol: 3-methoxybenzyl alcohol (248 μL, 2.0 mmol) and triethylamine (335 μL, 2.4 mmol) were dissolved in dichloromethane (DCM, 7 mL). Thionyl chloride (218 μL, 3.0 mmol) was added slowly. The reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was washed with 1N HCl aqueous solution. The organic phase was dried with anhydrous magnesium sulfate (MgSO?). The solvent was removed under reduced pressure to give the target product 3-methoxybenzyl chloride (313 mg, 100%) as a yellow oil. Next, 4-(4-chlorophenyl)-1-(2-methoxyethyl)-6-methyl-2-oxo-3,4-dihydropyridine-5-carboxylic acid (Example 74, 85 mg, 0.26 mmol) was dissolved in anhydrous N,N-dimethylformamide (DMF, 1 mL), followed by addition of cesium carbonate (169 mg, 0.52 mmol) and 3-methoxybenzyl chloride ( 81 mg, 0.52 mmol). The reaction mixture was stirred at room temperature for 18 hours. After completion of the reaction, the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (EtOAc) and water. The aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with brine and dried with anhydrous magnesium sulfate (MgSO?). The solvent was removed under reduced pressure. The crude product was purified by fast chromatography using a mixture of cyclohexane/ethyl acetate (8:2) as eluent to afford the target product (3-methoxyphenyl)methyl 4-(4-chlorophenyl)-1-(2-methoxyethyl)-6-methyl-2-oxo-3,4-dihydropyridine-5-carboxylate as a pale yellow oil (11 mg, 9%). Product characterization data: 1H NMR (300 MHz, CDCl?) δ 2.62 (s, 3H), 2.71 (dd, J = 15.8, 2.2 Hz, 1H), 2.92 (dd, J = 15.8, 7.5 Hz, 1H), 3.31 (s, 3H), 3.37 (ddt, J = 10.0, 8.5, 3.6 Hz, 1H). 3.46 (dt, J = 10.0, 4.1 Hz, 1H), 3.70-3.79 (m, 4H), 4.13-4.23 (m, 2H), 5.04 (d, J = 12.7 Hz, 1H), 5.11 (d, J = 12.7 Hz, 1H), 6.64 (s, 1H), 6.70 (d, J = 7.5 Hz, 1H), and 6.81 (dd, J = 8.2, 2.5 Hz, 1H), 7.10 (d, J = 8.4 Hz, 2H), 7.16-7.23 (m, 3H). Mass spectrum (MS): [M + H]? m/z 444. high-resolution mass spectrum (HRMS): calculated value of C??H??N?Cl, [M + H]? 444.1578, measured value 444.1579.
storage
3-Methoxybenzyl chloride is stored over K2CO3 to stabilize it.
References
[1] Patent: WO2016/16238, 2016, A1. Location in patent: Page/Page column 126-127
[2] Organic Process Research and Development, 2016, vol. 20, # 2, p. 568 - 573
[3] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 19, p. 8889 - 8895
[4] Journal of Organic Chemistry, 1998, vol. 63, # 25, p. 9565 - 9568
[5] Australian Journal of Chemistry, 1992, vol. 45, # 1, p. 71 - 97
3-Methoxybenzyl chloride Preparation Products And Raw materials
Raw materials
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View Lastest Price from 3-Methoxybenzyl chloride manufacturers
- Product
- 3-Methoxybenzyl chloride 824-98-6
- Price
- US $0.10/KG
- Min. Order
- 1KG
- Purity
- 99.0%
- Supply Ability
- 1000 tons
- Release date
- 2020-04-24
- Product
- 3-Methoxybenzyl chloride 824-98-6
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 97.1%
- Supply Ability
- 100 tons
- Release date
- 2022-02-18
- Product
- 3-Methoxybenzyl chloride 824-98-6
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- Custosmized
- Release date
- 2019-06-21