598-22-1

Basic information

• Product Name: Propionyl bromide
• Synonyms: PROPIONYL BROMIDE;Propanoyl bromide;Propionic acid bromide;1-Bromo-1-propanone;Propanoic acid bromide;Propionyl bromide,95%;Propionyl bromide 97%
• CAS NO: 598-22-1
• Molecular Formula: C₃H₅BrO
• Molecular Weight: 136.98
• EINECS: 209-924-0
• Product Categories: Organics;Acid Halides;Carbonyl Compounds;Organic Building Blocks;Acid Halides;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 598-22-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 103-104 °C(lit.)
• Flash Point: 126 °F
• Appearance: Gray-bluish/Tablets
• Density: 1.521 g/mL at 25 °C(lit.)
• Vapor Pressure: 32.5mmHg at 25°C
• Refractive Index: n20/D 1.455(lit.)
• Storage Temp.: Flammables area
• BRN: 1736651
• CAS DataBase Reference: Propionyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: Propionyl bromide(598-22-1)
• EPA Substance Registry System: Propionyl bromide(598-22-1)

Safety Data

• Hazard Codes: C
• Statements: 10-14-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2920 8/PG 2
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 598-22-1(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow to brown liquid, fuming with moisture

InChI:InChI=1/C3H5BrO/c1-2-3(4)5/h2H2,1H3

Synthetic route

propionic acid (802294-64-0) → propanoyl bromide (598-22-1)

Conditions	Yield
With bromine; triphenylphosphine In dichloromethane for 0.25h; Ambient temperature;	84%
With phosphorus; bromine
With dibromo sulfoxide
With lithium aluminium deuteride; sulfuric acid; hydrogen bromide Multistep reaction;
With ethyl tribromoacetate; triphenylphosphine In dichloromethane at 20℃; for 3h;

propionyl chloride (79-03-8) → propanoyl bromide (598-22-1)

Conditions	Yield
With trimethylsilyl bromide	74%

trimethylsilyl propionate (16844-98-7) → propanoyl bromide (598-22-1)

Conditions	Yield
With dibromotriphenylphosphorane In dichloromethane for 0.166667h; Ambient temperature;

propionyl radical (15843-24-0) → propanoyl bromide (598-22-1)

Conditions	Yield
With Bromotrichloromethane In hexane at 22.9℃; Rate constant;

propanoyl bromide (598-22-1) + N-deacetylcolchinyl methyl ether (84092-82-0) → N-propionylcolchinol methyl ether (851674-06-1)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 1h;	98%

propanoyl bromide (598-22-1) + 2-Methoxynaphthalene (93-04-9) → 1-(2-hydroxy-1-naphthyl)propan-1-one (33828-93-2)

Conditions	Yield
With aluminium trichloride In carbon disulfide for 2h; Heating;	95%

2-[5-amino-2-(trifluoromethyl)phenyl]-4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one (159547-29-2) + propanoyl bromide (598-22-1) → 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-2-[5-(propionylamino)-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one

Conditions	Yield
	95%

propanoyl bromide (598-22-1) + glycyl glycine ethyl ester hydrochloride (2087-41-4) → N-(bromoacetyl)glycylglycine ethyl ester

Conditions	Yield
With sodium hydrogencarbonate In water; benzene at 20℃;	94%

propanoyl bromide (598-22-1) + 1-Methoxynaphthalene (2216-69-5) → 2-propionyl-1-naphthol (24490-31-1)

Conditions	Yield
With aluminium trichloride In carbon disulfide for 2h; Heating;	93%

propanoyl bromide (598-22-1) + 2-<5-amino-2-(trifluoromethyl)phenyl>-5-n-butyl-4-<<2'-(N-tert-butylsulfamoyl)biphenyl-4-yl>methyl>-2,4-dihydro-3H-1,2,4-triazol-3-one (159954-93-5) → 5-n-butyl-4-<<2'-(N-tert-butylsulfamoyl)biphenyl-4-yl>methyl>-2,4-dihydro-2-<5-(propionylamino)-2-(trifluoromethyl)phenyl>-3H-1,2,4-triazol-3-one (159954-94-6)

Conditions	Yield
With pyridine; dmap Ambient temperature;	90%
dmap	67%

propanoyl bromide (598-22-1) + 4-nitrobenzaldehdye (555-16-8) → 3-(R)-methyl-4-(R)-(4'-nitrophenyl)oxetan-2-one

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; chiral Al(III)-triamine In dichloromethane at -30℃; for 20h; Cyclocondensation;	90%

propanoyl bromide (598-22-1) + glycine ethyl ester hydrochloride (623-33-6) → 2-(2-bromo-acetylamino)-acetic acid ethyl ester (15088-70-7)

Conditions	Yield
With sodium hydrogencarbonate In water; benzene at 20℃;	90%

propanoyl bromide (598-22-1) + (S)-alanine ethyl ester hydrochloride (1115-59-9) → L-2-(2-bromo-acetylamino)-propionic acid ethyl ester (1127352-23-1)

Conditions	Yield
With sodium hydrogencarbonate In water; benzene at 20℃;	90%

propanoyl bromide (598-22-1) + N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) → C22H25NO3

Conditions	Yield
With (11bS,11b’S)-2,6-bis(3,4,5-trifluorophenyl)-3,3’,5,5’-tetrahydro-4,4’-spirobi[dinaphtho[2,1-c:1’,2’-e]azepin]-4-ium bromide; ethyl 2-(2-(tert-butoxy)-1-((diphenylmethylene)amino)-2-oxoethyl)cyclopropane-1-carboxylate; potassium hydroxide In dichloromethane; water; toluene at 0℃; for 15h; Schlenk technique;	89%

propanoyl bromide (598-22-1) + 5-[(p-methoxy)benzyloxyl]-2-pentynal (246266-12-6) → 3-methyl-4-[4-(p-methoxybenzyloxy)butynyl]oxetan-2-one

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; chiral Al(III)-triamine In dichloromethane at -50℃; for 30h; Cyclocondensation;	86%

oct-2-ynal (1846-68-0) + propanoyl bromide (598-22-1) → 4-(hept-1-ynyl)-3-methyloxetan-2-one

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; chiral Al(III)-triamine In dichloromethane at -50℃; for 30h; Cyclocondensation;	85%

propanoyl bromide (598-22-1) + 4-(benzyloxy)but-2-ynal (95409-25-9) → 3-methyl-4-(3-benzyloxypropynyl)oxetan-2-one

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; chiral Al(III)-triamine In dichloromethane at -50℃; for 30h; Cyclocondensation;	85%

propanoyl bromide (598-22-1) + 2-(5-Amino-2-chlorophenyl)-5-n-butyl-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]-methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (159547-32-7) → 5-n-Butyl-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-2-[2-chloro-5-(propionylamino)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (159547-33-8)

Conditions	Yield
With dmap In pyridine Ambient temperature;	84%
	84%
dmap	84%

propanoyl bromide (598-22-1) + 4-bromo-5-(1H-indol-3-yl)oxazole (1383483-16-6) → C14H11BrN2O2 (1383483-40-6)

Conditions	Yield
Stage #1: 4-Bromo-5-(1H-indol-3-yl)oxazole With sodium hydride; N,N-dimethyl-formamide In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Stage #2: propanoyl bromide With N,N-dimethyl-formamide In tetrahydrofuran; mineral oil at 40℃; for 3h;	84%

propanoyl bromide (598-22-1) + (2-amino-4-methoxy-3-(methoxymethoxy)phenyl)(3,4-dimethoxy-5-(methylthio)phenyl)methanone → N-(6-(3,4-dimethoxy-5-(methylthio)benzoyl)-3-methoxy-2-(methoxymethoxy)phenyl)propionamide

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 3h;	81%

propanoyl bromide (598-22-1) + benzaldehyde (100-52-7) → (3R,4R)-3-methyl-4-phenyloxetan-2-one (652150-85-1)

Conditions	Yield
With (S,S)-ArSO2NCH(i-Pr)CH2N(CH2CF3)CH2CH(i-Pr)NSO2CF3*AlMe; N-ethyl-N,N-diisopropylamine In various solvent(s) at -25℃; for 14h;	80%

Methyl 3-aminothiophene-2-carboxylate (22288-78-4) + propanoyl bromide (598-22-1) → methyl 3-propionamidothiophene-2-carboxylate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 4h;	80%

propanoyl bromide (598-22-1) + benzyloxyacetoaldehyde (60656-87-3) → 3-methyl-4-(benzyloxymethyl)oxetan-2-one

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; chiral Al(III)-triamine In dichloromethane at -30℃; for 48h; Cyclocondensation;	78%

propanoyl bromide (598-22-1) + 2-(5-amino-2-bromophenyl)-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one (159547-23-6) → 2-[2-Bromo-5-(propionylamino)phenyl]-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one (159547-24-7)

Conditions	Yield
	77%

propanoyl bromide (598-22-1) + trans-(4-{4-[2-(4-aminocyclohexyl)ethyl]piperazin-1-yl}-5,6-dichloropyrimidin-2-yl) methyl amine dihydrochloride → trtrans-N-(4-{2-[4-(5,6-dichloro-2-methylaminopyrimidin-4-yl)piperazin-1-yl]ethyl}cyclohexylpropionamide)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 5℃; for 5h; Industrial scale;	75%

propanoyl bromide (598-22-1) + copper(I) cyanide (544-92-3) → 2-oxo-butyronitrile (4390-78-7)

Conditions	Yield
at 90℃; for 2h;	74%
In 1,2-dichloro-benzene

bis(triethylgermyl)mercury (4149-28-4) + propanoyl bromide (598-22-1) → triethylpropionylgermane (94047-78-6) + 3,4-hexanedione (4437-51-8) + Bromotriethylgermanium (1067-10-3) + mercury

Conditions	Yield
In benzene Irradiation (UV/VIS); Ge-compd. addn. to org. compd. soln., sealing in evac. ampul, irradiation (DRT-375 quartz mercury lamp) until orange color disappeard; fractionation; GLC anal.;	A 15% B 71% C n/a D n/a

propanoyl bromide (598-22-1) + butyraldehyde (123-72-8) → (3R,4R)-trans-3-Methyl-4-propyloxetan-2-one

Conditions	Yield
With 2Br(1-)*C41H51AlN4O2(2+); N-ethyl-N,N-diisopropylamine In dichloromethane at -70℃; for 24h; Inert atmosphere; optical yield given as %ee;	67%
With 2Br(1-)*C41H51AlN4O2(2+); N-ethyl-N,N-diisopropylamine In dichloromethane at -70℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	67%

propanoyl bromide (598-22-1) + propionic acid anhydride (123-62-6) + 6,6-dimethyl-5,6-dihydro-3-methyl-4-phenyl-1,2-oxazine N-oxide (638133-04-7) → 1-[3-(bromomethyl)-6,6-dimethyl-4-phenyl-5,6-dihydro-2H-1,2-oxazin-2-yl]propan-1-one

Conditions	Yield
In dichloromethane at 20℃; for 24h;	61%

propanoyl bromide (598-22-1) + 2-(3-aminophenyl)-5-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (147776-56-5) → 5-n-Butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-2-[3-(propionylamino)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Conditions	Yield
	60%
With sodium hydride 1.) DMF, RT, 3 h, 2.) DMF, 50 deg C, overnight; Yield given. Multistep reaction;

2-[5-amino-2-(trifluoromethyl)phenyl]-5-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one + propanoyl bromide (598-22-1) → 5-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-2,4-dihydro-2-[5-(propionylamino)-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene	60%

3-phenyl-propionaldehyde (104-53-0) + propanoyl bromide (598-22-1) → (3S,4S)-trans-3-methyl-4-(2-phenylethyl)-oxetan-2-one

Conditions	Yield
With bis(isopropyl)ethylamine; (R,R)-(-)-N,N'-bis(3-pentyl-5-(4-methylpyridinium-1-ylmethyl)salicylidene)-1,2-cyclohexanediamine dibromide; trimethylaluminum In dichloromethane; toluene at -70℃; for 24h; optical yield given as %ee; enantioselective reaction;	60%

Upstream product

• 802294-64-0 propionic acid 
• 15843-24-0 propionyl radical 
• 79-03-8 propionyl chloride 
• 16844-98-7 trimethylsilyl propionate 

Downstream Products

• 1461-23-0 tributyltin bromide 
• 94047-78-6 triethylpropionylgermane 
• 4437-51-8 3,4-hexanedione 
• 1067-10-3 Bromotriethylgermanium 
• 1246737-04-1 (3R,4S)-trans-3-methyl-4-(4-trifluoromethylphenyl)oxetan-2-one 
• 1246737-05-2 (3R,4S)-trans-3-methyl-4-(4-chlorophenyl)oxetan-2-one 
• 1246737-07-4 (3R,4S)-trans-3-methyl-4-(4-nitrophenyl)oxetan-2-one 
• 1246737-08-5 (3R,4S)-trans-3-methyl-4-(4-bromophenyl)oxetan-2-one 
• 1246737-06-3 (3R,4S)-trans-3-methyl-4-(4-cyanophenyl)oxetan-2-one 

Relevant articles and documents

A mild and efficient reaction for conversion of carboxylic acids into acid bromides with ethyl tribromoacetate/triphenylphosphine under acid-free conditions

Acid bromides were prepared efficiently from carboxylic acids with readily available ethyl tribromoacetate and triphenylphosphine at room temperature under neutral conditions. The present process is applicable to the preparation of various acid bromides from aromatic and aliphatic carboxylic acids. Aromatic carboxylic acids were found to be more reactive than aliphatic carboxylic acids under reaction conditions.

Reagents and Synthetic Methods; 14. A Facile Synthesis of Carboxylic Acid Bromides and Esters under Neutral Conditions via Reaction of the Trimethylsilyl Esters with Triphenylphosphine Dibromide

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Noncompeting Metastable Losses of Methyl and Ethylene from Gaseous Butanoic Acid Ions due to Isomerization Prior to Methyl Loss

Metastable C4H8O+. ions obtained from butanoic acid and ethyl butanoate undergo considerable γ-hydrogen exchange prior to losing ethylene, but little exchange prior to losing methyl.Therefore the two fragmentations are not directly competing, contrary to the general assumption that all reactions of an ion in the gas phase are competitive.It is concluded that metastable butanoic acid ions which lose methyl isomerize essentially irreversibly to CH3CH2C.HC(OH)2+ and/or CH3CH(C.H2)C(OH)2+ before the γ-methyl becomes exchanged.This accounts for the difference between γ-hydrogen exchange prior to the loss of methyl and ethylene without invoking isolated electronic states, as previously proposed.Butanoic acid ions generated by the McLafferty rearrangement of butanoate esters have a much weaker metastable loss of ethylene than directly ionized butanoic acid.Collisional activation experiments demonstrate that this results from more of the butanoic acid ions derived from ethyl butanoate than from butanoic acid isomerizing prior to collision.Variation in internal energy probably causes this difference in degree of isomerization with the source of the ion.