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270245

Sigma-Aldrich

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
Beilstein:
606667
EC Number:
212-540-6
MDL number:
MFCD00000915
UNSPSC Code:
12352100
PubChem Substance ID:
24856365
NACRES:
NA.22

Assay

98%

form

liquid

contains

potassium carbonate as stabilizer

refractive index

n20/D 1.548 (lit.)

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

SMILES string

COc1ccc(CCl)cc1

InChI

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

InChI key

MOHYOXXOKFQHDC-UHFFFAOYSA-N

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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

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

228.2 °F - closed cup

Flash Point(C)

109 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
Andrew J Horan et al.
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