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Merck
CN

364878

1-Bromocarbonyl-1-methylethyl acetate

≥95.0%

Synonym(s):

α-Acetoxyisobutyryl bromide, 2-Acetoxy-2-methylpropionyl bromide

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About This Item

Linear Formula:
CH3COOC(CH3)2COBr
CAS Number:
40635-67-4
Molecular Weight:
209.04
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24862463
MDL number:
MFCD00040923
Beilstein/REAXYS Number:
2432585

Key Documents

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InChI

1S/C6H9BrO3/c1-4(8)10-6(2,3)5(7)9/h1-3H3

SMILES string

CC(=O)OC(C)(C)C(Br)=O

InChI key

OOKAXSHFTDPZHP-UHFFFAOYSA-N

assay

≥95.0%

refractive index

n20/D 1.457 (lit.)

bp

75-77 °C/12 mmHg (lit.)

density

1.431 g/mL at 25 °C (lit.)

storage temp.

2-8°C

General description

1-Bromocarbonyl-1-methylethyl acetate (α-Acetoxyisobutyryl bromide) participates in the conversion of adenosine to trans-3′(2′)-bromo-2′(3′)-acetates, via glycosyl cleavage.

Application

1-Bromocarbonyl-1-methylethyl acetate (α-Acetoxyisobutyryl bromide) may be used:
  • in the chemoenzymatic synthesis of (1R,2S)-1,2-epoxy-1,2-dihydroacridine (acridine 1,2-oxide)
  • in the synthesis of protected 3′-deoxyadenosine and 3′-deoxyguanosine
  • as reagent for deoxygenation of vicinal diols, as well as in the preparation of 2′,3′-dideoxycytidine and other dideoxy and deoxynucleosides from the corresponding ribo series.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

hcodes

H314,H335

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B - STOT SE 3

target_organs

Respiratory system

supp_hazards

EUH014

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °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
BCCB3745
BCBZ4697
BCBZ5238
BCBX4741
BCBW8905

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A mild conversion of vicinal diols to alkenes. Efficient transformation of ribonucleosides into 2'-ene and 2t', 3'-dideoxynucleosides.
Robins MJ, et al.
Tetrahedron Letters, 25(4), 367-370 (1984)
Aldrichimica Acta, 23, 83-83 (1990)
Efficient synthesis of protected 3'-deoxyadenosine and 3'-deoxyguanosine from adenosine and guanosine.
Cui Z, et al.
Tetrahedron Letters, 42(4), 561-563 (2001)
Biphenyl dioxygenase-catalysed cis-dihydroxylation of tricyclic azaarenes: chemoenzymatic synthesis of arene oxide metabolites and furoquinoline alkaloids.
Boyd DR, et al.
Royal Society of Chemistry Advances, 3(27), 10944-10955 (2013)

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