40635-67-4

Basic information

• Product Name: 2-Acetoxy-2-methylpropionyl bromide
• Synonyms: 1-BROMOCARBONYL-1-METHYLETHYL ACETATE;2-ACETOXYISOBUYRYL BROMIDE;2-ACETOXYISOBUTYRYL BROMIDE;2-ACETOXY-2-METHYLPROPIONYL BROMIDE;AIBB;ACETOXYISOBUTYRIC ACID BROMIDE;ALPHA-ACETOXYISOBUTYRYL BROMIDE;2-(acetyloxy)-2-methyl-Propanoylbromide
• CAS NO: 40635-67-4
• Molecular Formula: C₆H₉BrO₃
• Molecular Weight: 209.04
• EINECS: -0
• Product Categories: Pharmaceutical Intermediates;Acid Halides;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 40635-67-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 75-77 °C12 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.431 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.542mmHg at 25°C
• Refractive Index: n20/D 1.457
• Storage Temp.: 2-8°C
• Sensitive: Moisture Sensitive
• BRN: 2432585
• CAS DataBase Reference: 2-Acetoxy-2-methylpropionyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Acetoxy-2-methylpropionyl bromide(40635-67-4)
• EPA Substance Registry System: 2-Acetoxy-2-methylpropionyl bromide(40635-67-4)

Safety Data

• Hazard Codes: C
• Statements: 14-34-37
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 10-19
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 40635-67-4(Hazardous Substances Data)

Usage

Uses

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.

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.

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

Synthetic route

2-acetoxy-2-methylpropanoyl chloride (40635-66-3) → acetoxyisobutyryl bromide (40635-67-4)

Conditions	Yield
With lithium bromide In ethyl acetate at 80℃; for 2h;	52%
With lithium bromide

O-acetyl-α-hydroxyisobutyric acid (15805-98-8) → acetoxyisobutyryl bromide (40635-67-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / 2 h / Heating 2: 52 percent / LiBr / ethyl acetate / 2 h / 80 °C View Scheme

acetoxyisobutyryl bromide (40635-67-4) + 1-(4-C-trifluoromethyl-β-D-ribo-furanosyl)triazole (219649-71-5) → 1-<5-O-(2-acetoxy-2-methylpropanoyl)-3-O-acetyl-2-bromo-2-deoxy-4-C-trifluoromethyl-β-D-ribo-furanosyl>triazole (219649-72-6)

Conditions	Yield
at 100℃; for 2h;	100%

acetoxyisobutyryl bromide (40635-67-4) + 9-(4-C-trifluoromethyl-β-D-ribo-furanosyl)-6-methoxypurine (219649-65-7) → 5'-O-(2-acetoxy-2-methylpropanoyl)-3'-O-acetyl-2'-bromo-2'-deoxy-4'-C-(trifluoromethyl)inosine (219649-66-8)

Conditions	Yield
at 100℃; overnight;	98%

(1S,2S)-1,2-dihydroxy-3-fluorocyclohex-3-ene + acetoxyisobutyryl bromide (40635-67-4) → (+)-(1S,2R)-1-acetoxy-2-bromo-3-fluorocyclohex-3-ene (1431975-46-0)

Conditions	Yield
In acetonitrile at 0 - 20℃; for 2.5h;	96%

acetoxyisobutyryl bromide (40635-67-4) + cis-(1S,2S)-1,2-dihydroxy-3-chlorocyclohex-3-ene (176166-15-7) → (+)-(1S,2R)-1-acetoxy-2-bromo-3-chlorocyclohex-3-ene (1431975-48-2)

Conditions	Yield
In acetonitrile at 0 - 20℃; for 2.5h;	95%

acetoxyisobutyryl bromide (40635-67-4) + cis-(1S,2S)-1,2-dihydroxy-3-iodocyclohex-3-ene (176166-16-8) → (+)-(1S,2R)-1-acetoxy-2-bromo-3-iodocyclohex-3-ene (1431975-51-7)

Conditions	Yield
In acetonitrile at 0 - 20℃; for 2.5h;	94%

acetoxyisobutyryl bromide (40635-67-4) + 3-(2,3-dihydroxy-3-methyl-butyl)-4-methoxy-1H-quinolin-2-one (316172-90-4) → (-)-(S)-4-methoxy-3-(2'-acetoxy-3'-bromo-3'-methylbutyl)quinolin-2(1H)-one (316172-92-6)

Conditions	Yield
In acetonitrile at 0℃; for 3h; Acetylation;	93%

3,4-cis-tetrahydrodiol (828295-32-5) + acetoxyisobutyryl bromide (40635-67-4) → (+)-(1S,2S)-1-acetoxy-2,4-dibromocyclohex-3-ene (1431975-55-1)

Conditions	Yield
In acetonitrile at 0 - 20℃; for 2.5h;	92%

acetoxyisobutyryl bromide (40635-67-4) + (1S,4S,5R)-1-Benzyloxycarbonyloxy-4,5-dihydroxy-cyclohex-2-enecarboxylic acid methyl ester (183134-54-5) → (1S,4R,5R)-5-Acetoxy-1-benzyloxycarbonyloxy-4-bromo-cyclohex-2-enecarboxylic acid methyl ester (183134-55-6)

Conditions	Yield
In acetonitrile at 0℃; for 0.5h;	91%

acetoxyisobutyryl bromide (40635-67-4) + cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohex-3-ene (174817-06-2) → (+)-(1S,2R)-1-acetoxy-2,3-dibromocyclohex-3-ene (176166-10-2)

Conditions	Yield
	90%
In acetonitrile at 0 - 20℃; for 2.5h;	90%

(7S,8R)-4-methoxy-5,6,7,8-tetrahydrofuro[2,3-b]quinoline-7,8-diol (865878-22-4) + acetoxyisobutyryl bromide (40635-67-4) → (7S,8S)-8-bromo-4-methoxy-5,6,7,8-tetrahydrofuro[2,3-b]quinolin-7-yl acetate (865878-23-5)

Conditions	Yield
In acetonitrile	90%
In acetonitrile at 0 - 20℃;	90%

(1S,2R)-3-phenylcyclohex-3-ene-1,2-diol (187837-12-3) + acetoxyisobutyryl bromide (40635-67-4) → (1S,2S)-2-bromo-3-phenylcyclohex-3-enyl acetate (1498378-64-5)

Conditions	Yield
In acetonitrile at 0℃; for 3h; chemoselective reaction;	90%

acetoxyisobutyryl bromide (40635-67-4) + (1R,2R,3R,4R)-5-methyl-5-cyclohexene-1,2,3,4-tetraol (144668-28-0) → (1S,2S,5S,6S)-6-(acetyloxy)-2,5-dibromo-3-methyl-3-cyclohexenyl acetate

Conditions	Yield
In acetonitrile at 0 - 20℃; for 2.25h;	88%

acetoxyisobutyryl bromide (40635-67-4) + (1'R,2'R,3'S,4'R,5'S)-4-(6-aminopurin-9-yl)-1-(hydroxymethyl)bicyclo[3.1.0]hexane-2,3-diol → (1'R,2'S,3'S,4'R,5'S)-9-[3'-acetoxy-1'-bromomethyl-2'-bromobicyclo[3.1.0]hexan-4'-yl]adenine (1174673-38-1)

Conditions	Yield
In water; acetonitrile at 20℃; for 1h; stereoselective reaction;	88%

acetoxyisobutyryl bromide (40635-67-4) + 5'-O-[(tert-butyl)diphenylsilyl]-N2-[(dimethylamino)methylene]guanosine → 1-{2-O-acetyl-3-bromo-5-O-[(tert-butyl)diphenylsilyl]-3-deoxy-β-D-xylofuranosyl}-N2-[(dimethylamino)methylene]guanine

Conditions	Yield
In water; acetonitrile at 20℃; for 3h; Acetylation; Bromination;	87%

acetoxyisobutyryl bromide (40635-67-4) + (1S,2S,3S,4S)-5-chloro-5-cyclohexene-1,2,3,4-tetraol (154097-66-2) → (1S,2R,5R,6R)-6-(acetyloxy)-2,5-dibromo-3-chloro-3-cyclohexenyl acetate

Conditions	Yield
In acetonitrile at 0 - 20℃;	87%
In acetonitrile Acetylation; Substitution;

acetoxyisobutyryl bromide (40635-67-4) + (1R,2R,3S,4S)-5-iodo-5-cyclohexene-1,2,3,4-tetraol (320410-60-4) → (1S,2R,5S,6S)-6-(acetyloxy)-2,5-dibromo-3-iodo-3-cyclohexenyl acetate (900792-05-4)

Conditions	Yield
In acetonitrile at 0 - 20℃; for 2.25h;	87%
In acetonitrile Acetylation; Substitution;
In acetonitrile at 0 - 20℃; for 2.25h;

acetoxyisobutyryl bromide (40635-67-4) + (1S,2S,3S,4S)-5-bromo-5-cyclohexene-1,2,3,4-tetraol (154097-67-3) → (1S,2R,5R,6R)-6-(acetyloxy)-2,3,5-tribromo-3-cyclohexenyl acetate

Conditions	Yield
In acetonitrile at 0 - 20℃;	86%
In acetonitrile Acetylation; Substitution;

acetoxyisobutyryl bromide (40635-67-4) + methyl shikimate (40983-58-2) → (+)-methyl (3R,4S,5R)-3-bromo-4-acetoxy-5-hydroxy-1-cyclohexene-1-carboxylate (127617-49-6)

Conditions	Yield
In acetonitrile at 0℃; for 0.5h;	85%
In acetonitrile at 0℃; for 0.5h;	76%

acetoxyisobutyryl bromide (40635-67-4) + 3-(2,3-dihydroxy-3-methyl-butyl)-4-methoxy-1H-quinolin-2-one (316172-94-8) → (+)-(R)-4-methoxy-3-(2'-acetoxy-3'-bromo-3'-methylbutyl)quinolin-2(1H)-one (316172-96-0)

Conditions	Yield
In acetonitrile at 0℃; Acetylation;	85%

acetoxyisobutyryl bromide (40635-67-4) + 6-N-benzoyl-9-(5-O-tert-butyldiphenylsilyl-β-D-ribofuranosyl)adenine (77244-83-8) → 9-(2'-O-acetyl-3'-bromo-5'-O-tert-butyldiphenylsilyl-3'-deoxy-β-D-xylofuranosyl)-6-N-benzoyl adenine (329014-11-1)

Conditions	Yield
With water In acetonitrile at 0 - 20℃; for 9.5h;	84%

acetoxyisobutyryl bromide (40635-67-4) + (1R,2R,3S,4S)-5-chloro-5-cyclohexene-1,2,3,4-tetraol (145107-30-8) → (1S,2R,5S,6S)-6-(acetyloxy)-2,5-dibromo-3-chloro-3-cyclohexenyl acetate (900791-76-6)

Conditions	Yield
In acetonitrile at 0 - 20℃; for 2.25h;	83%
In acetonitrile Acetylation; Substitution;

acetoxyisobutyryl bromide (40635-67-4) + 5'-O-[(tert-butyl)diphenylsilyl]-2-[(dimethylamino)methylidene]guanosine (160905-87-3) → 9-(2'-O-acetyl-3'-bromo-5'-O-tert-butyldiphenylsilyl-3'-deoxy-β-D-xylofuranosyl)-2-N-(N',N'-dimethylaminomethylene) guanine (247223-54-7)

Conditions	Yield
With water In acetonitrile at 0℃;	83%
With water In acetonitrile at 0 - 20℃; for 6h; Moffatt reaction;	82.8%

acetoxyisobutyryl bromide (40635-67-4) + 4'-C-trifluoromethyl-5-methyluridine (219649-53-3) → 5'-O-(2-acetoxy-2-methylpropanoyl)-3'-O-acetyl-2'-bromo-2'-deoxy-4'-C-trifluoromethyl-5-methyluridine (219649-54-4)

Conditions	Yield
at 100℃; for 2h;	81%

acetoxyisobutyryl bromide (40635-67-4) + C13H17N9O4 (1509918-84-6) → C15H18BrN9O4 (1509918-85-7)

Conditions	Yield
In water; acetonitrile for 1h; Inert atmosphere;	81%
In water; acetonitrile at 20℃; for 1h; Inert atmosphere;	71%

acetoxyisobutyryl bromide (40635-67-4) + rac-1,4,5,6-tetra-O-benzyl-myo-inositol (26276-99-3) → (+/-)-2-O-Acetyl-3,4,5,6-tetra-O-benzyl-1-bromo-1-deoxy-chiro-inositol + (+/-)-2-O-Acetyl-3,4,5,6-tetra-O-benzyl-1-bromo-1-deoxy-scyllo-inositol

Conditions	Yield
In acetonitrile for 1h; Ambient temperature;	A 80% B 10%

acetoxyisobutyryl bromide (40635-67-4) + (1R,2R,3S,4S)-5-bromo-5-cyclohexene-1,2,3,4-tetraol (154013-20-4) → (1S,2R,5S,6S)-6-(acetyloxy)-2,3,5-tribromo-3-cyclohexenyl acetate (900791-79-9)

Conditions	Yield
In acetonitrile at 0 - 20℃; for 2.25h;	80%
In acetonitrile Acetylation; Substitution;

acetoxyisobutyryl bromide (40635-67-4) + (1S,2S,3S,4S)-5-iodo-5-cyclohexene-1,2,3,4-tetraol (320410-59-1) → (1S,2R,5R,6R)-6-(acetyloxy)-2,5-dibromo-3-iodo-3-cyclohexenyl acetate (320410-63-7)

Conditions	Yield
In acetonitrile at 0 - 20℃;	80%
In acetonitrile Acetylation; Substitution;

(1R,2R,3S,4S)-2-methyl-5-cyclohexene-1,2,3,4-tetraol + acetoxyisobutyryl bromide (40635-67-4) → (1R,2R,5S,6S)-6-(acetyloxy)-2,5-dibromo-6-methyl-3-cyclohexenyl acetate

Conditions	Yield
In acetonitrile at 0 - 20℃;	80%

acetoxyisobutyryl bromide (40635-67-4) + (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-((tert-butyldiphenylsilyloxy)methyl)tetrahydrofuran-3,4-diol (119898-65-6) → Acetic acid (2R,3R,5R)-5-(6-amino-purin-9-yl)-4-bromo-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester + (2R,3S,4S,5R)-2-(6-amino-9H-purin-9-yl)-4-bromo-5-((tert-butyldiphenylsilyloxy)methyl)tetrahydrofuran-3-yl acetate (557771-59-2)

Conditions	Yield
With water In acetonitrile at 0℃; for 5h; Moffatt reaction;	A n/a B 79.5%

(+)-(1S,2S,3S,4S)-2-methyl-5-cyclohexene-1,2,3,4-tetraol (900791-68-6) + acetoxyisobutyryl bromide (40635-67-4) → (1R,2R,5R,6R)-6-(acetyloxy)-2,5-dibromo-1-methyl-3-cyclohexenyl acetate (900791-85-7)

Conditions	Yield
In acetonitrile at 0 - 20℃; for 2.25h;	79%

Upstream product

• 40635-66-3 2-acetoxy-2-methylpropanoyl chloride 
• 15805-98-8 O-acetyl-α-hydroxyisobutyric acid 

Downstream Products

• 40627-14-3 2'-Deoxyformycin A 
• 40627-34-7 7-amino-3-<5-O-(2-acetoxyisobutyryl)-3-bromo-3-deoxy-β-D-xylofuranosyl>-1H-pyrazolo<4,3-d>pyrimidine 
• 40627-36-9 (1S)-1-(7-amino-1⁽²⁾H-pyrazolo[4,3-d]pyrimidin-3-yl)-3-bromo-D-1,4-anhydro-3-deoxy-xylitol 
• 77421-68-2 1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-thymine 
• 122383-25-9 2-Acetoxy-2-methyl-propionic acid (2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl ester 
• 3056-17-5 stavudin 
• 159551-90-3 (1R,2S,5S)-6-oxa-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid dibenzyl ester 
• 557771-59-2 (2R,3S,4S,5R)-2-(6-amino-9H-purin-9-yl)-4-bromo-5-((tert-butyldiphenylsilyloxy)methyl)tetrahydrofuran-3-yl acetate 
• 1174673-43-8 (1'R,2'S,3'S,4'R,5'S)-9-(3'-acetoxy-1'-bromomethyl-2'-bromobicyclo[3.1.0]hex-4'-yl)-N₆-benzyladenine 
• 1431975-48-2 (+)-(1S,2R)-1-acetoxy-2-bromo-3-chlorocyclohex-3-ene 
• 1431975-46-0 (+)-(1S,2R)-1-acetoxy-2-bromo-3-fluorocyclohex-3-ene 
• 1431975-55-1 (+)-(1S,2S)-1-acetoxy-2,4-dibromocyclohex-3-ene 
• 1431975-53-9 (+)-(1S,2S)-1-acetoxy-2-bromo-3-(trifluoromethyl)cyclohex-3-ene 
• 1431975-51-7 (+)-(1S,2R)-1-acetoxy-2-bromo-3-iodocyclohex-3-ene 

Relevant articles and documents

Nucleotides: Part LIX: Synthesis, characterization, and biological activities of new potential antiviral agents: (2'-5')Adenylate trimer analogs containing 3'-deoxy-3'(hexadecanoylamino)adenosine at the 2'-terminus

Based upon 3'-amino-3'-deoxyadenosine (15), its protected 3'- hexadecanoylamino derivative 22 was chosen as starting material for the synthesis of a series of new modified 2'-5'-adenylate trimers 33-36 as potential antiviral agents. All (2'-5')A trimer analogs 33-36 inhibit HIV-1 replication as measured by the inhibition of syncytia formation and inhibition of HIV-1 reverse transcriptase activity. Compound 34 inhibits HIV- 1 reverse transcription by 100% and subsequently inhibits expression of HIV- 1 p24. However, compound 35 acts differently, since it does not inhibit HIV- 1 reverse transcription, HIV-1 integrase, or HIV-1 p24 expression. Therefore, 35 appears to exert its inhibitory effect at a later stage of HIV-1 replication, i.e., the budding process.