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186791

Sigma-Aldrich

tert-Butyl chloroacetate

97%

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Linear Formula:
ClCH2COOC(CH3)3
CAS Number:
107-59-5
Molecular Weight:
150.60
Beilstein:
1753006
EC Number:
203-506-1
MDL number:
MFCD00000930
PubChem Substance ID:
24851243
NACRES:
NA.22

Quality Level

200

Assay

97%

refractive index

n20/D 1.423 (lit.)

bp

48-49 °C/11 mmHg (lit.)

density

1.053 g/mL at 25 °C (lit.)

SMILES string

CC(C)(C)OC(=O)CCl

InChI

1S/C6H11ClO2/c1-6(2,3)9-5(8)4-7/h4H2,1-3H3

InChI key

KUYMVWXKHQSIAS-UHFFFAOYSA-N

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Application

tert-Butyl chloroacetate was used in the synthesis of:
  • imidazol-1-yl-acetic acid hydrochloride
  • cis-disubstituted aziridine ester via aza-Darzens reaction
  • 1,10-diaza-18-crown-6 based sensors bearing a coumarin fluorophore

Regulatory Information

危险化学品

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Substituent dependent fluorescence response of diazacrown-based PET sensors.
Nagy K, et al.
Tetrahedron, 64(27), 6191-6195 (2008)
Santosh Kumar Singh et al.
Beilstein journal of organic chemistry, 4, 42-42 (2008-12-24)
A convenient and practical synthesis of imidazol-1-yl-acetic acid hydrochloride was achieved via N-alkylation of imidazole using tert-butyl chloroacetate followed by a non-aqueous ester cleavage of the resulting imidazol-1-yl-acetic acid tert-butyl ester in the presence of titanium tetrachloride. The synthesized imidazol-1-yl-acetic
E Vedejs et al.
The Journal of organic chemistry, 65(18), 5498-5505 (2000-09-02)
Intermolecular alkylation of the aziridinyl oxazole 20 using PhSO(2)CH(2)CH(2)OTf is possible despite the presence of potentially nucleophilic aziridine nitrogen. The resulting oxazolium salt 22 reacts with BnNMe(3)(+)CN(-) to produce the azomethine ylide 24b via electrocyclic ring opening of an oxazoline

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