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CAS No.: | 3395-91-3 |
---|---|
Name: | Methyl 3-bromopropionate |
Article Data: | 20 |
Molecular Structure: | |
Formula: | C4H7BrO2 |
Molecular Weight: | 167.002 |
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); |
EINECS: | 222-247-5 |
Density: | 1.501 g/cm3 |
Melting Point: | 75°C |
Boiling Point: | 166.537 °C at 760 mmHg |
Flash Point: | 75 °C |
Solubility: | Water Solubility : Immiscible |
Appearance: | Very slightly yellow liquid |
Hazard Symbols: | Xn |
Risk Codes: | 22-36/37/38 |
Safety: | 26-37/39 |
PSA: | 26.30000 |
LogP: | 0.94440 |
acrylic acid methyl ester
Methyl 3-bromopropionate
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 |
Conditions | Yield |
---|---|
With hydroquinone In methanol at 20 - 50℃; for 2h; | 96% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; silver nitrate In acetone at 20℃; for 6h; | 88% |
With N-Bromosuccinimide; dibenzoyl peroxide |
Conditions | Yield |
---|---|
With thionyl chloride at 20℃; for 12h; | 81% |
In dichloromethane for 18h; Reflux; | 81% |
With sulfuric acid for 5h; Heating; | 70% |
methanol
A
Methyl 3-bromopropionate
B
methyl 3-methoxypropionate
C
ethylene dibromide
D
2-Bromoethyl methyl ether
Conditions | Yield |
---|---|
With bromine at -80℃; temperature up to 30 deg C; | A 67% B n/a C n/a D n/a |
Conditions | Yield |
---|---|
Stage #1: β-Propiolactone With hydrogen bromide; acetic acid at 20℃; for 20h; Stage #2: methanol at 20℃; for 15h; | 56% |
Conditions | Yield |
---|---|
With Acetyl bromide; hydroquinone; ethyl acrylate at 20 - 50℃; for 2h; Overall yield = 88.5 g; | A n/a B 53% |
methanol
ethyl acrylate
A
Ethyl 3-bromopropionate
B
Methyl 3-bromopropionate
Conditions | Yield |
---|---|
With Acetyl bromide; hydroquinone at 20 - 55℃; for 2h; Overall yield = 92.3 g; | A 51% B n/a |
1-bromovinylbenzene
acrylic acid
A
Methyl 3-bromopropionate
B
(+/-)-1,2-dihydro-[1]naphthoic acid
Conditions | Yield |
---|---|
With toluene |
Conditions | Yield |
---|---|
(i) TlOEt, (ii) Br2; Multistep reaction; |
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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 %.
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 %.
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, |