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584-93-0 Usage

Chemical Properties

Clear pale yellow liquid

Uses

2-Bromovaleric acid was used in the solid-phase synthesis of 2,4,5-trisubstituted thiomorpholine-3-ones.

Check Digit Verification of cas no

The CAS Registry Mumber 584-93-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,8 and 4 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 584-93:
(5*5)+(4*8)+(3*4)+(2*9)+(1*3)=90
90 % 10 = 0
So 584-93-0 is a valid CAS Registry Number.
InChI:InChI=1/C5H9BrO2/c1-2-3-4(6)5(7)8/h4H,2-3H2,1H3,(H,7,8)/p-1/t4-/m0/s1

584-93-0 Well-known Company Product Price

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  • Alfa Aesar

  • (L07047)  2-Bromovaleric acid, 98%   

  • 584-93-0

  • 25g

  • 265.0CNY

  • Detail

584-93-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Bromovaleric acid

1.2 Other means of identification

Product number -
Other names 2-bromopentanoic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:584-93-0 SDS

584-93-0Synthetic route

valeric acid
109-52-4

valeric acid

2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

Conditions
ConditionsYield
With bromine; phosphorus trichloride for 4.5h; Heating;91%
With N-Bromosuccinimide; sulfuric acid In trifluoroacetic acid at 85℃; for 16h;86%
With bromine; trichlorophosphate at 80 - 105℃; for 17h;72.6%
n-propylmalonic acid
616-62-6

n-propylmalonic acid

2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

Conditions
ConditionsYield
With diethyl ether; bromine in direktem Sonnenlicht einwirken und erhitzt die hierbei erhaltene Brompropylmalonsaeure auf 145;
2-hydroperoxy-butan-2-ol
19393-67-0

2-hydroperoxy-butan-2-ol

acrylonitrile
107-13-1

acrylonitrile

2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

Conditions
ConditionsYield
With hydrogen bromide; iron(II) sulfate
n-valeryl chloride
638-29-9

n-valeryl chloride

2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

Conditions
ConditionsYield
With bromine at 90℃; for 16h; 2) 100 deg C, 0.5 h; Yield given;
2-aminopentanoic acid
760-78-1

2-aminopentanoic acid

2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

Conditions
ConditionsYield
With hydrogen bromide; sodium nitrite In water
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

diallylamine
124-02-7

diallylamine

N,N-diallyl-2-bromopentanamide

N,N-diallyl-2-bromopentanamide

Conditions
ConditionsYield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane at 15℃; for 2h;90%
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

A

3-[4-[4-(3-Chlorophenyl)-1-piperazinyl[butyl]-5-propyl-2,4-thiazolidinedione Dihydrochloride

3-[4-[4-(3-Chlorophenyl)-1-piperazinyl[butyl]-5-propyl-2,4-thiazolidinedione Dihydrochloride

B

5-(propyl)-2,4-thiazolidinedione sodium salt

5-(propyl)-2,4-thiazolidinedione sodium salt

Conditions
ConditionsYield
With thioureaA n/a
B 87%
propan-1-ol
71-23-8

propan-1-ol

2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

propyl 2-bromopentanoate

propyl 2-bromopentanoate

Conditions
ConditionsYield
With sulfuric acid Reflux;87%
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

triethylammonium-2-N-morpholino-dithiocarbamate
23336-68-7

triethylammonium-2-N-morpholino-dithiocarbamate

2-N-morpholino-dithiocarbamoyl-pentanoic acid
181036-27-1

2-N-morpholino-dithiocarbamoyl-pentanoic acid

Conditions
ConditionsYield
In benzene at 20℃; for 16h;85%
In Petroleum ether for 6h; Ambient temperature; Yield given;
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

2-methyl-4-nitro-benzenamine
99-52-5

2-methyl-4-nitro-benzenamine

2-Bromo-pentanoic acid (2-methyl-4-nitro-phenyl)-amide
83473-12-5

2-Bromo-pentanoic acid (2-methyl-4-nitro-phenyl)-amide

Conditions
ConditionsYield
With phosphorus trichloride In benzene for 3h; Heating;84%
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

2-(4-chloro-5-methyl-2-mercaptobenzenesulfonylimino)hexahydropyrimidine
188717-79-5

2-(4-chloro-5-methyl-2-mercaptobenzenesulfonylimino)hexahydropyrimidine

2-[5-Chloro-4-methyl-2-(tetrahydro-pyrimidin-2-ylidenesulfamoyl)-phenylsulfanyl]-pentanoic acid
188718-92-5

2-[5-Chloro-4-methyl-2-(tetrahydro-pyrimidin-2-ylidenesulfamoyl)-phenylsulfanyl]-pentanoic acid

Conditions
ConditionsYield
With sodium hydroxide; sodium carbonate In water at 80 - 85℃; for 2h;78%
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

1-(4-chloro-5-cyano-2-mercaptobenzenesulphonyl)-2-imidazolidinone
160985-01-3

1-(4-chloro-5-cyano-2-mercaptobenzenesulphonyl)-2-imidazolidinone

2-[5-Chloro-4-cyano-2-(2-oxo-imidazolidine-1-sulfonyl)-phenylsulfanyl]-pentanoic acid

2-[5-Chloro-4-cyano-2-(2-oxo-imidazolidine-1-sulfonyl)-phenylsulfanyl]-pentanoic acid

Conditions
ConditionsYield
With sodium hydroxide; sodium carbonate In water at 40 - 80℃; for 6.5h;76%
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

2,6-dimethyl-4-nitroaniline
16947-63-0

2,6-dimethyl-4-nitroaniline

2-Chloro-pentanoic acid (2,6-dimethyl-4-nitro-phenyl)-amide

2-Chloro-pentanoic acid (2,6-dimethyl-4-nitro-phenyl)-amide

Conditions
ConditionsYield
With phosphorus trichloride In benzene for 3h; Heating;73%
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

1-(5-cyano-2-mercaptobenzenesulphonyl)-2-imidazolidinone
160985-00-2

1-(5-cyano-2-mercaptobenzenesulphonyl)-2-imidazolidinone

2-[4-Cyano-2-(2-oxo-imidazolidine-1-sulfonyl)-phenylsulfanyl]-pentanoic acid

2-[4-Cyano-2-(2-oxo-imidazolidine-1-sulfonyl)-phenylsulfanyl]-pentanoic acid

Conditions
ConditionsYield
With sodium hydroxide; sodium carbonate In water at 40 - 80℃; for 6.5h;73%
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

dibenzylamine
103-49-1

dibenzylamine

N,N-dibenzyl-2-bromopentanamide

N,N-dibenzyl-2-bromopentanamide

Conditions
ConditionsYield
Stage #1: 2-Bromovaleric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at 0℃; for 4h; Inert atmosphere;
Stage #2: dibenzylamine With lithium chloride In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;
71%
piperidine
110-89-4

piperidine

2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

2-bromo-1-(piperidin-1-yl)pentan-1-one

2-bromo-1-(piperidin-1-yl)pentan-1-one

Conditions
ConditionsYield
Stage #1: 2-Bromovaleric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at 0℃; for 4h; Inert atmosphere;
Stage #2: piperidine With lithium chloride In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;
69%
5-bromo-2-pyridylamine
1072-97-5

5-bromo-2-pyridylamine

2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

2-Bromo-pentanoic acid (5-bromo-pyridin-2-yl)-amide

2-Bromo-pentanoic acid (5-bromo-pyridin-2-yl)-amide

Conditions
ConditionsYield
Stage #1: 2-Bromovaleric acid With oxalyl dichloride; N,N-dimethyl-formamide In 1,2-dichloro-ethane at 0 - 20℃; for 5h;
Stage #2: 5-bromo-2-pyridylamine With N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; for 1.16667h;
65%
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

diethylamine
109-89-7

diethylamine

2-bromo-N, N-diethylpentanamide

2-bromo-N, N-diethylpentanamide

Conditions
ConditionsYield
Stage #1: 2-Bromovaleric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at 0℃; for 4h; Inert atmosphere;
Stage #2: diethylamine With lithium chloride In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;
64%
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

2-(4-chloro-5-methyl-2-mercaptobenzenesulfonylimino)-5,5-dimethylhexahydropyrimidine
188717-81-9

2-(4-chloro-5-methyl-2-mercaptobenzenesulfonylimino)-5,5-dimethylhexahydropyrimidine

2-[5-Chloro-2-(5,5-dimethyl-tetrahydro-pyrimidin-2-ylidenesulfamoyl)-4-methyl-phenylsulfanyl]-pentanoic acid
188718-95-8

2-[5-Chloro-2-(5,5-dimethyl-tetrahydro-pyrimidin-2-ylidenesulfamoyl)-4-methyl-phenylsulfanyl]-pentanoic acid

Conditions
ConditionsYield
With sodium hydroxide; sodium carbonate In water at 80 - 85℃; for 2h;60%
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

p-Chlorothiophenol
106-54-7

p-Chlorothiophenol

2-((4-chlorophenyl)thio)pentanoic acid

2-((4-chlorophenyl)thio)pentanoic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 140℃; for 0.333333h; Microwave irradiation;58%
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

diisopropylamine
108-18-9

diisopropylamine

2-bromo-N, N-diisopropylpentanamide

2-bromo-N, N-diisopropylpentanamide

Conditions
ConditionsYield
Stage #1: 2-Bromovaleric acid With oxalyl dichloride In dichloromethane at 40℃; for 2h; Inert atmosphere;
Stage #2: diisopropylamine With lithium chloride In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere;
57%
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

1-(4-chloro-2-mercapto-5-methylbenzenesulfonyl)imidazolidin-2-one

1-(4-chloro-2-mercapto-5-methylbenzenesulfonyl)imidazolidin-2-one

2-[5-Chloro-4-methyl-2-(2-oxo-imidazolidine-1-sulfonyl)-phenylsulfanyl]-pentanoic acid
168698-63-3

2-[5-Chloro-4-methyl-2-(2-oxo-imidazolidine-1-sulfonyl)-phenylsulfanyl]-pentanoic acid

Conditions
ConditionsYield
With sodium hydroxide; sodium carbonate In water at 40 - 80℃; for 6.5h;55%
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

isopropylamine
75-31-0

isopropylamine

2-bromo-N-isopropylpentanamide

2-bromo-N-isopropylpentanamide

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 10h;54%
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

4-Chloro-N-[4-ethyl-tetrahydro-pyrimidin-(2E)-ylidene]-2-mercapto-5-methyl-benzenesulfonamide
188717-83-1

4-Chloro-N-[4-ethyl-tetrahydro-pyrimidin-(2E)-ylidene]-2-mercapto-5-methyl-benzenesulfonamide

2-{5-Chloro-2-[4-ethyl-tetrahydro-pyrimidin-(2E)-ylidenesulfamoyl]-4-methyl-phenylsulfanyl}-pentanoic acid
188718-97-0

2-{5-Chloro-2-[4-ethyl-tetrahydro-pyrimidin-(2E)-ylidenesulfamoyl]-4-methyl-phenylsulfanyl}-pentanoic acid

Conditions
ConditionsYield
With sodium hydroxide; sodium carbonate In water at 80 - 85℃; for 2h;53%
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

N-Benzylaniline
758640-21-0

N-Benzylaniline

N-benzyl-2-bromo-N-phenylpentanamide

N-benzyl-2-bromo-N-phenylpentanamide

Conditions
ConditionsYield
Stage #1: 2-Bromovaleric acid With oxalyl dichloride In dichloromethane at 40℃; for 2h; Inert atmosphere;
Stage #2: N-Benzylaniline With lithium chloride In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere;
53%
p-cresol
106-44-5

p-cresol

2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

2-(p-tolyloxy)pentanoic acid

2-(p-tolyloxy)pentanoic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 0 - 100℃; for 20h;51.9%
morpholine
110-91-8

morpholine

2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

2-bromo-1-morpholinopentan-1-one

2-bromo-1-morpholinopentan-1-one

Conditions
ConditionsYield
Stage #1: 2-Bromovaleric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at 0℃; for 4h; Inert atmosphere;
Stage #2: morpholine With lithium chloride In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;
46%
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

valeric acid
109-52-4

valeric acid

Conditions
ConditionsYield
With phosphate buffer; tris[3-(2-methoxyethoxy)propyl]stannane In water Irradiation; or with ACVA initiation;37%
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

para-thiocresol
106-45-6

para-thiocresol

2-(p-tolylthio)pentanoic acid

2-(p-tolylthio)pentanoic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 140℃; for 0.333333h; Microwave irradiation;37%
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

thiophenol
108-98-5

thiophenol

2-(phenylthio)pentanoic acid

2-(phenylthio)pentanoic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 140℃; for 0.333333h; Microwave irradiation;36%
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

2.6-dimethylpiperidine
504-03-0

2.6-dimethylpiperidine

2-bromo-1-(2,6-dimethylpiperidin-1-yl)pentan-1-one

2-bromo-1-(2,6-dimethylpiperidin-1-yl)pentan-1-one

Conditions
ConditionsYield
Stage #1: 2-Bromovaleric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at 0℃; for 4h; Inert atmosphere;
Stage #2: 2.6-dimethylpiperidine With lithium chloride In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;
32%
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

2-bromo-N,N-dicyclohexylpentanamide

2-bromo-N,N-dicyclohexylpentanamide

Conditions
ConditionsYield
Stage #1: 2-Bromovaleric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at 0℃; for 4h; Inert atmosphere;
Stage #2: N-cyclohexyl-cyclohexanamine With lithium chloride In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;
28%
2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

benzylamine
100-46-9

benzylamine

N-benzyl-2-bromopentanamide

N-benzyl-2-bromopentanamide

Conditions
ConditionsYield
Stage #1: 2-Bromovaleric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at 0℃; for 4h; Inert atmosphere;
Stage #2: benzylamine With lithium chloride In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;
19%
morpholine
110-91-8

morpholine

2-Bromovaleric acid
584-93-0

2-Bromovaleric acid

2-morpholino-valeric acid ethyl ester
100050-35-9

2-morpholino-valeric acid ethyl ester

584-93-0Relevant articles and documents

Silver-Promoted Fluorination Reactions of α-Bromoamides

Mizuta, Satoshi,Kitamura, Kanami,Kitagawa, Ayako,Yamaguchi, Tomoko,Ishikawa, Takeshi

supporting information, p. 5930 - 5935 (2021/02/01)

Silver-promoted C?F bond formation in α-bromoamides by using AgF under mild conditions is reported. This simple method enables access to tertiary, secondary, and primary alkyl fluorides involving biomolecular scaffolds. This transformation is applicable to primary and secondary amides and shows broad functional-group tolerance. Kinetics experiments revealed that the reaction rate increased in the order of 3°>2°>1° α-carbon atom. In addition, it was found that the acidic amide proton plays an important role in accelerating the reaction. Mechanistic studies suggested generation of an aziridinone intermediate that undergoes subsequent nucleophilic addition to form the C?F bond with stereospecificity (i.e., retention of configuration). The synthesis of sterically hindered alcohols and ethers by using AgI is also demonstrated. Examples of reactions of α-bromoamides with O nucleophiles are presented.

Enantioselective construction of tetrasubstituted stereogenic carbons through bronsted base catalyzed michael reactions: α′-hydroxy enones as key enoate equivalent

Badiola, Eider,Fiser, Bla,Gmez-Bengoa, Enrique,Mielgo, Antonia,Olaizola, Iurre,Urruzuno, Iaki,Garca, Jess M.,Odriozola, Jos M.,Razkin, Jess,Oiarbide, Mikel,Palomo, Claudio

supporting information, p. 17869 - 17881 (2015/02/19)

Catalytic and asymmetric Michael reactions constitute very powerful tools for the construction of new C-C bonds in synthesis, but most of the reports claiming high selectivity are limited to some specific combinations of nucleophile/electrophile compound types, and only few successful methods deal with the generation of all-carbon quaternary stereocenters. A contribution to solve this gap is presented here based on chiral bifunctional Bronsted base (BB) catalysis and the use of α′-oxy enones as enabling Michael acceptors with ambivalent H-bond acceptor/donor character, a yet unreported design element for bidentate enoate equivalents. It is found that the Michael addition of a range of enolizable carbonyl compounds that have previously demonstrated challenging (i.e., α-substituted 2-oxindoles, cyanoesters, oxazolones, thiazolones, and azlactones) to α′-oxy enones can afford the corresponding tetrasubstituted carbon stereocenters in high diastereo- and enantioselectivity in the presence of standard BB catalysts. Experiments show that the α′-oxy ketone moiety plays a key role in the above realizations, as parallel reactions under identical conditions but using the parent α,β-unsaturated ketones or esters instead proceed sluggish and/or with poor stereoselectivity. A series of trivial chemical manipulations of the ketol moiety in adducts can produce the corresponding carboxy, aldehyde, and ketone compounds under very mild conditions, giving access to a variety of enantioenriched densely functionalized building blocks containing a fully substituted carbon stereocenter. A computational investigation to rationalize the mode of substrate activation and the reaction stereochemistry is also provided, and the proposed models are compared with related systems in the literature.

Mesoionic 5-alkyl-1,3-dithiolium-4-thiolates: Synthesis and brine shrimp toxicity

De Almeida, Paulo Afonso,Da Silva, Tania Maria Sarmento,Echevarria, Aurea

, p. 593 - 600 (2007/10/03)

A series of twelve 1,3-dithiolium-4-thiolate mesoionic compounds were synthesized and characterized. The synthetical approach starting from α-bromoalkanoic acids to obtain the corresponding 2-N-morpholino-dithiocarbamoyl-carboxylic acids that by on-pot reaction with carbon disulfide and acetic anhydride in triethylamine formed not isolate intermediates, 1,3-dithiolium-4-olates. After, the 2-N-morpholino-5-alkyl-1,3-dithiolium-4-thiolates were obtained by retro 1,3-dipolar addition reactions. The alkyl moiety linked to C-5 of heterocyclic ring permitted the increase of the hydrophobic character and this effect was evaluated on Artemia salina lethality. The results indicated a bell-shaped relationship between the number of carbon of side chain in mesoionic derivatives and LD50 in brine shrimp toxicity assays.

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