Methyl 3-bromopropionate supplier

Name
Methyl 3-bromopropionate
EINECS 222-247-5
CAS No. 3395-91-3
Article Data20
CAS DataBase
Density 1.501 g/cm³
Solubility Water Solubility : Immiscible
Melting Point 75°C
Formula C₄H₇BrO₂
Boiling Point 166.537 °C at 760 mmHg
Molecular Weight 167.002
Flash Point 75 °C
Transport Information
Appearance Very slightly yellow liquid
Safety 26-37/39
Risk Codes 22-36/37/38
Molecular Structure
Hazard Symbols Xn
Synonyms b-Bromopropionic acid methyl ester;NSC 3705;Methyl b-bromopropionate;3-Bromopropionic acid methyl ester;3-Bromopropanoic acid methyl ester;Propionicacid, 3-bromo-, methyl ester (6CI,7CI,8CI);
PSA 26.30000
LogP 0.94440

Synthetic route

: 292638-85-8
acrylic acid methyl ester

: 3395-91-3
Methyl 3-bromopropionate

Conditions

Conditions	Yield
With boron tribromide; ethylene glycol In dichloromethane at 0 - 20℃; for 24h; Concentration; Inert atmosphere;	96%
With diethyl ether; hydrogen bromide anfangs unter Eiskuehlung, dann bei Raumtemperatur;
With hydrogen bromide
With hydrogen bromide In chloroform-d1

: 506-96-7
Acetyl bromide

: 292638-85-8
acrylic acid methyl ester

: 3395-91-3
Methyl 3-bromopropionate

Conditions

Conditions	Yield
With hydroquinone In methanol at 20 - 50℃; for 2h;	96%

: 554-12-1
propanoic acid methyl ester

: 3395-91-3
Methyl 3-bromopropionate

Conditions

Conditions	Yield
With N-Bromosuccinimide; silver nitrate In acetone at 20℃; for 6h;	88%
With N-Bromosuccinimide; dibenzoyl peroxide

: 590-92-1
3-Bromopropionic acid

: 67-56-1
methanol

: 3395-91-3
Methyl 3-bromopropionate

Conditions

Conditions	Yield
With thionyl chloride at 20℃; for 12h;	81%
In dichloromethane for 18h; Reflux;	81%
With sulfuric acid for 5h; Heating;	70%

: 67-56-1
methanol

Tetracarbonyleisenkomplexe des Ethylens: Tetracarbonyleisenkomplexe des Ethylens

A: 3395-91-3
Methyl 3-bromopropionate

B: 3852-09-3
methyl 3-methoxypropionate

C: 106-93-4
ethylene dibromide

D: 6482-24-2
2-Bromoethyl methyl ether

Conditions

Conditions	Yield
With bromine at -80℃; temperature up to 30 deg C;	A 67% B n/a C n/a D n/a

...Expand

: 67-56-1
methanol

: 57-57-8
β-Propiolactone

: 3395-91-3
Methyl 3-bromopropionate

Conditions

Conditions	Yield
Stage #1: β-Propiolactone With hydrogen bromide; acetic acid at 20℃; for 20h; Stage #2: methanol at 20℃; for 15h;	56%

: 64-17-5
ethanol

A: 539-74-2
Ethyl 3-bromopropionate

B: 3395-91-3
Methyl 3-bromopropionate

Conditions

Conditions	Yield
With Acetyl bromide; hydroquinone; ethyl acrylate at 20 - 50℃; for 2h; Overall yield = 88.5 g;	A n/a B 53%

: 67-56-1
methanol

: 140-88-5
ethyl acrylate

A: 539-74-2
Ethyl 3-bromopropionate

B: 3395-91-3
Methyl 3-bromopropionate

Conditions

Conditions	Yield
With Acetyl bromide; hydroquinone at 20 - 55℃; for 2h; Overall yield = 92.3 g;	A 51% B n/a

...Expand

: 98-81-7
1-bromovinylbenzene

: 79-10-7
acrylic acid

A: 3395-91-3
Methyl 3-bromopropionate

B: 16827-42-2
(+/-)-1,2-dihydro-[1]naphthoic acid

Conditions

Conditions	Yield
With toluene

...Expand

: 3878-55-5
methyl hydrogen succinate

: 3395-91-3
Methyl 3-bromopropionate

Conditions

Conditions	Yield
(i) TlOEt, (ii) Br2; Multistep reaction;

: 14213-56-0
methyl β-diazopropionate

: 3395-91-3
Methyl 3-bromopropionate

Conditions

Conditions	Yield
With hydrogen bromide In diethyl ether

: 67-56-1
methanol

: 3-bromo-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)propanamide

: 3395-91-3
Methyl 3-bromopropionate

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate at 100℃; for 20h; Sealed tube;	85 %Spectr.

: 615-15-6
2-Methyl-1H-benzimidazole

: 3395-91-3
Methyl 3-bromopropionate

: 138942-42-4
methyl-3-(2-methyl-1H-1,3-benzodiazol-1-yl)propanoate

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran Ambient temperature;	100%
With potassium carbonate In N,N-dimethyl-formamide	96%
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 16h;	96%
With potassium carbonate In N,N-dimethyl-formamide	96%

: 3395-91-3
Methyl 3-bromopropionate

: 23605-39-2
azido-b-alanine methyl ester

Conditions

Conditions	Yield
With sodium azide In dimethyl sulfoxide at 45℃; for 24h;	100%
With sodium azide In water; acetone at 60℃; for 4h; Inert atmosphere;	98%
With sodium azide In dimethyl sulfoxide Ambient temperature;	94%

: 2075-46-9
4-nitro-1H-pyrazole

: 3395-91-3
Methyl 3-bromopropionate

: 3-(4-nitro-pyrazol-1-yl)-propionic acid

Conditions

Conditions	Yield
Stage #1: 4-nitro-1H-pyrazole; Methyl 3-bromopropionate With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 3h; Stage #2: With water; lithium hydroxide In methanol at 20℃; for 0.5h;	100%

: 3395-91-3
Methyl 3-bromopropionate

: 5-methoxy-1-methyl-1H-benzo[d]imidazole-2-thiol

: C13H16N2O3S

Conditions

Conditions	Yield
In methanol at 20 - 82℃; for 24h;	100%

: 3395-91-3
Methyl 3-bromopropionate

: 672-66-2
Dimethyl(phenyl)phosphine

: (3-methoxy-3-oxopropyl)dimethyl(phenyl)phosphonium bromide

Conditions

Conditions	Yield
In acetonitrile at 20℃;	99%

: 117-99-7
2-Hydroxybenzophenone

: 3395-91-3
Methyl 3-bromopropionate

: 60312-26-7
(3-phenylbenzofuran-2-yl)acetic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate at 80℃;	99%

: 3395-91-3
Methyl 3-bromopropionate

: [NMe4][1-(MeS)-7-(Me2S)B12H10]

: 414868-01-2
1-(MeS(CH2)2C(O)OMe)-7-(Me2S)B12H10

Conditions

Conditions	Yield
In acetonitrile to soln. (Me4N)(B12H10(SMe2)SMe) in MeCN excess alkyl halide was added and stirred overnight; volatiles were removed in vacuo, residue was treated with water and CH2Cl2, organic phase was dried over MgSO4, solvent was removed;	97%

: 3395-91-3
Methyl 3-bromopropionate

: 536-74-3
phenylacetylene

: 68979-66-8
3-(4-phenyl-[1,2,3]triazol-1-yl)-propionic acid methyl ester

Conditions

Conditions	Yield
With sodium azide; sodium hydroxide In water at 55℃; for 3h; Huisgen Cycloaddition; Green chemistry; regioselective reaction;	97%
With sodium azide; sodium L-ascorbate In water at 50℃; for 2h; Huisgen Cycloaddition; Green chemistry;	96%
With sodium azide; sodium L-ascorbate In water; tert-butyl alcohol at 55℃; for 2.5h; Huisgen Cycloaddition; Green chemistry; regioselective reaction;	95%

: 3395-91-3
Methyl 3-bromopropionate

: 84468-17-7
N-(2-aminomethyl)-5-isoquinolinesulfonamide

: 129786-37-4
methyl N-(2-isoquinoline-5-sulfonamidoethyl)-3-amino-propionate

Conditions

Conditions	Yield
With triethylamine In methanol for 4h; Heating;	95%

: 3395-91-3
Methyl 3-bromopropionate

: 5029-66-3
methyl 3-iodopropanoate

Conditions

Conditions	Yield
With sodium iodide In acetone at 20℃;	95%
With sodium iodide In acetone 1.) 2 h, 2.) 50 deg C, 45 min; Yield given;
With sodium iodide In acetone

: 3395-91-3
Methyl 3-bromopropionate

: 103-67-3
benzyl-methyl-amine

: 17946-01-9
methyl 3-propanoate

Conditions

Conditions	Yield
With sodium carbonate In acetonitrile at 70℃; for 70h;	95%
With sodium carbonate In acetonitrile at 70℃; for 70h;	95%
With sodium carbonate In acetonitrile at 70℃; for 24h; Inert atmosphere;	92%
With sodium carbonate In acetonitrile at 70℃; for 24h;	92%

: 3395-91-3
Methyl 3-bromopropionate

: (R)-tetrahydropapaverine N-acetyl-L-leucine salt

: 144-62-7
oxalic acid

: 1075726-76-9
(1R)-1-[(3,4-dimethoxyphenyl)-methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methoxycarbonylethyl-isoquinoline oxalate

Conditions

Conditions	Yield
Stage #1: Methyl 3-bromopropionate; (R)-tetrahydropapaverine N-acetyl-L-leucine salt With sodium carbonate In water; toluene; acetonitrile at 55 - 80℃; for 24h; pH=9; Stage #2: oxalic acid In acetone Temperature; Reagent/catalyst; pH-value;	95%

...Expand

: 3395-91-3
Methyl 3-bromopropionate

: 1016755-45-5
piperidine-4-carboxylic acid [2-(4-methoxy-phenyl)-ethyl]-amide

: 3-{4-[2-(4-methoxy-phenyl)-ethylcarbamoyl]-piperidin-1-yl}-propionic acid methyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 50℃; for 48h;	94%

: 3395-91-3
Methyl 3-bromopropionate

: 603-35-0
triphenylphosphine

: 937233-06-2
C22H22O2P(1+)*Br(1-)

Conditions

Conditions	Yield
In toluene for 12h; Reflux;	94%

: 3395-91-3
Methyl 3-bromopropionate

: 3,3-diphenylazetidine hydrogen oxalate

: C19H21NO2*C2H2O4

Conditions

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 110℃; for 16h; Inert atmosphere;	94%

: 3395-91-3
Methyl 3-bromopropionate

: 925-90-6
ethylmagnesium bromide

: 128312-82-3
1-(2-bromoethyl)cyclopropan-1-ol

Conditions

Conditions	Yield
With titanium(IV) isopropylate In tetrahydrofuran; diethyl ether at 20℃; for 4h;	92%
With titanium(IV) isopropylate In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;	12%
With titanium(IV) isopropylate In diethyl ether at 18 - 20℃; for 0.166667h;
Stage #1: Methyl 3-bromopropionate; ethylmagnesium bromide With titanium(IV) isopropylate In diethyl ether Stage #2: With sulfuric acid; water In diethyl ether at 0℃;

: 91-22-5
quinoline

: 3395-91-3
Methyl 3-bromopropionate

: 1-(2-carbmethoxyethyl)-quinolinium hexafluorophosphate

Conditions

Conditions	Yield
Stage #1: quinoline; Methyl 3-bromopropionate In ethanol for 4h; Heating; Stage #2: With ammonium hexafluorophosphate In water at 20℃;	92%

: 147497-32-3
6-bromo-3,4-dihydroisoquinolin-1(2H)-one

: 3395-91-3
Methyl 3-bromopropionate

: 3-(6-bromo-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)propionic acid methyl ester

Conditions

Conditions	Yield
Stage #1: 6-bromo-3,4-dihydroisoquinolin-1(2H)-one With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Stage #2: Methyl 3-bromopropionate In tetrahydrofuran; mineral oil for 2h; Reflux;	92%

: 3395-91-3
Methyl 3-bromopropionate

: C4H5BrN2O2

Conditions

Conditions	Yield
With C8H8N4O4S; triethylamine In 1,2-dichloro-ethane at 0 - 20℃; for 1h;	92%

: 18514-88-0
6-chloro-4(1H)-cinnoline

: 3395-91-3
Methyl 3-bromopropionate

: 1027195-94-3
3-(6-Chloro-4-oxo-4H-cinnolin-1-yl)-propionic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetone for 5h; Ambient temperature;	91.2%

: 3395-91-3
Methyl 3-bromopropionate

: 3-Bromo-6-methyl-1H-cinnolin-4-one

: 3-(3-Bromo-6-methyl-4-oxo-4H-cinnolin-1-yl)-propionic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 10h; Heating;	91.2%

: 3395-91-3
Methyl 3-bromopropionate

: 81344-31-2
1,1-dideuterio-3-bromopropanol

Conditions

Conditions	Yield
With aluminum (III) chloride; lithium aluminium deuteride In diethyl ether at -20℃; for 1h; Inert atmosphere;	91%
With aluminium trichloride; lithium aluminium deuteride	2.89%

: 3395-91-3
Methyl 3-bromopropionate

: 108-42-9
3-chloro-aniline

: 42313-47-3
methyl N-(3-chlorophenyl)-β-alaninate

Conditions

Conditions	Yield
With sodium carbonate for 6h; Heating;	91%

: 3395-91-3
Methyl 3-bromopropionate

: 371-40-4
4-fluoroaniline

: 135154-75-5
3-bromo-N-(4-fluorophenyl)propionamide

Conditions

Conditions	Yield
Stage #1: 4-fluoroaniline With trimethylaluminum In tetrahydrofuran; hexane at -78 - 20℃; for 0.333333h; Stage #2: Methyl 3-bromopropionate In tetrahydrofuran; hexane for 2h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane at 0℃;	91%
Stage #1: 4-fluoroaniline With trimethylaluminum In tetrahydrofuran; hexane at -78℃; for 0.333333h; Stage #2: Methyl 3-bromopropionate In tetrahydrofuran; hexane at 20℃; for 3h;

: 6478-79-1
5,6-dichloro-2-methylbenzimidazole

: 3395-91-3
Methyl 3-bromopropionate

: 1449030-60-7
methyl 3-(5,6-dichloro-2-methyl-1H-benzimidazol-1-yl)propanoate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 16h;	91%

: 3395-91-3
Methyl 3-bromopropionate

: 3034-38-6
1H-4(5)-nitroimidazole

: 328056-86-6
3-(4-nitro-imidazol-1-yl)-propionic acid methyl ester

Conditions

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetonitrile at 80℃; for 0.5h;	90%

: 889129-61-7
6-methoxy-3-(4-methoxy-phenylsulfonyl)-1H-indole

: 3395-91-3
Methyl 3-bromopropionate

: 3-[6-methoxy-3-(4-methoxy-benzenesulfonyl)-indol-1-yl]-propionic acid methyl ester

Conditions

Conditions	Yield
Stage #1: 6-methoxy-3-(4-methoxy-phenylsulfonyl)-1H-indole With potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water at 20℃; for 0.0833333h; Stage #2: Methyl 3-bromopropionate In dichloromethane; water at 20℃; for 16h;	90%

: 3395-91-3
Methyl 3-bromopropionate

: 57260-71-6
1-t-Butoxycarbonylpiperazine

: 656803-51-9
4-(2-methoxycarbonylethyl)-piperazine-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃;	90%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 50℃; for 18h; Inert atmosphere;	85%
With caesium carbonate In N,N-dimethyl-formamide at 20℃;	74%
With triethylamine In tetrahydrofuran at 20℃; for 18h;

Methyl 3-bromopropionate Specification

The Methyl 3-bromopropionate, with the CAS registry number 3395-91-3, is also known as Propanoic acid, 3-bromo-, methyl ester. It belongs to the product categories of Organics; C2 to C5; Carbonyl Compounds; Esters. Its EINECS registry number is 222-247-5. This chemical's molecular formula is C₄H₇BrO₂ and molecular weight is 167.00. What's more, its IUPAC name is the same with its product name. It should be stored in a cool, dry and well-ventilated place.

Physical properties about Methyl 3-bromopropionate are: (1)ACD/LogP: 1.08; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.08; (4)ACD/LogD (pH 7.4): 1.08; (5)ACD/BCF (pH 5.5): 3.90; (6)ACD/BCF (pH 7.4): 3.90; (7)ACD/KOC (pH 5.5): 92.18; (8)ACD/KOC (pH 7.4): 92.18; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 26.3 Å²; (13)Index of Refraction: 1.453; (14)Molar Refractivity: 30.087 cm³; (15)Molar Volume: 111.226 cm³; (16)Surface Tension: 33.79 dyne/cm; (17)Density: 1.501 g/cm³; (18)Flash Point: 75 °C; (19)Enthalpy of Vaporization: 40.301 kJ/mol; (20)Boiling Point: 166.537 °C at 760 mmHg; (21)Vapour Pressure: 1.776 mmHg at 25 °C.

Preparation of Methyl 3-bromopropionate: this chemical can be prepared by 3-Bromo-propionic acid with Methanol. This reaction needs reagent SOCl₂ at temperature of 20 °C. The reaction time is 12 hours. The yield is 81 %.

Methyl 3-bromopropionate can be prepared by 3-Bromo-propionic acid with Methanol.

Uses of Methyl 3-bromopropionate: (1) it is used as organic intermediate; (2) it is used to produce other chemicals. For example, it can react with 2-Methyl-1H-benzoimidazole to get 1-(2-Methoxycarbonylethyl)-2-methylbenzimidazole. The reaction occurs with reagent NaH and solvent tetrahydrofuran at ambient temperature. The yield is 100 %.

Methyl 3-bromopropionate can react with 2-Methyl-1H-benzoimidazole to get 1-(2-Methoxycarbonylethyl)-2-methylbenzimidazole.

When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health and it is harmful if swallowed. Therefore, you should wear suitable protective clothing and eye/face protection. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: BrCCC(=O)OC
(2) InChI: InChI=1S/C4H7BrO2/c1-7-4(6)2-3-5/h2-3H2,1H3
(3) InChIKey: KQEVIFKPZOGBMZ-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD50	oral	1600mg/kg (1600mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA VASCULAR: REGIONAL OR GENERAL ARTERIOLAR OR VENOUS DILATION	National Technical Information Service. Vol. OTS0570991,

Product Name

Methyl 3-bromopropionate

Synthetic route

Methyl 3-bromopropionate Specification

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