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Merck
CN

270245

4-Methoxybenzyl chloride

contains potassium carbonate as stabilizer, 98%

Synonym(s):

4-(Chloromethyl)anisole

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About This Item

Linear Formula:
CH3OC6H4CH2Cl
CAS Number:
824-94-2
Molecular Weight:
156.61
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24856365
EC Number:
212-540-6
Beilstein/REAXYS Number:
606667
MDL number:
MFCD00000915
Assay:
98%
Form:
liquid

Key Documents

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InChI key

MOHYOXXOKFQHDC-UHFFFAOYSA-N

InChI

1S/C8H9ClO/c1-10-8-4-2-7(6-9)3-5-8/h2-5H,6H2,1H3

SMILES string

COc1ccc(CCl)cc1

assay

98%

form

liquid

contains

potassium carbonate as stabilizer

bp

117-118 °C/14 mmHg (lit.)

mp

−1 °C (lit.)

density

1.155 g/mL at 25 °C (lit.)

storage temp.

2-8°C

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General description

4-Methoxybenzyl chloride undergoes mild oxidative claevage with ceric ammonium nitrate.

Application

4-Methoxybenzyl chloride was used to benzylate the aniline nitrogen. It was also used in the synthesis of 1-naphthamide and diarymethanes via Suzuki cross-coupling with postassium aryltrifluoroborates.
O/N protecting group reagent which can be mildly oxidatively cleaved, e.g., with ceric ammonium nitrate.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

228.2 °F - closed cup

flash_point_c

109 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000067298
0000050176
0000039237
0000023629
MKCF5973

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Gary A Molander et al.
The Journal of organic chemistry, 71(24), 9198-9202 (2006-11-18)
[reaction: see text] The palladium-catalyzed cross-coupling of potassium aryltrifluoroborates with benzylic halides occurs in good yield with high functional group tolerance. The increased stability of potassium aryltrifluoroborates compared to other boron coupling partners makes this an effective route to functionalized
Andrew J Horan et al.
Analytical chemistry, 89(2), 1059-1062 (2017-02-15)
Airborne nanoparticles play a key role in climate effects as well as impacting human health. Their small mass and complex chemical composition represent significant challenges for analysis. This work introduces a new ionization method, droplet assisted inlet ionization (DAII), where
Martin H Bolli et al.
Journal of medicinal chemistry, 47(11), 2776-2795 (2004-05-14)
Since its discovery in 1988 by Yanagisawa et al., endothelin (ET), a potent vasoconstrictor, has been widely implicated in the pathophysiology of cardiovascular, cerebrovascular, and renal diseases. Many research groups have embarked on the discovery and development of ET receptor
Synthesis of a potent (?)-4-(2-hydroxyphenyl) analogue of the acromelic acids by dearomatising cyclisation of a lithiated N-p-methoxybenzyl-4-methoxy-1-naphthamide.
Tetrahedron Letters, 42(20), 3407-3410 (2001)
Thompson AS, et al.
Tetrahedron Letters, 36(49), 8937-8940 (1995)
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