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ChemicalBook--->CAS DataBase List--->4224-69-5

4224-69-5

4224-69-5 Structure

4224-69-5 Structure
IdentificationMore
[Name]

Methyl 2-(bromomethyl)acrylate
[CAS]

4224-69-5
[Synonyms]

2-BROMOMETHYL METHYL ACRYLATE
METHYL 2-(BROMOMETHYL)ACRYLATE
2-(bromomethyl)-2-propenoicacimethylester
2-(bromomethyl)-acrylicacimethylester
methyl2-(bromomethyl)-2-propenoate
alpha-(Bromomethyl)-acrylic acid methyl ester
2-Propenoic acid, 2-(bromomethyl)-, methyl ester
2-(Bromomethyl)acrylic acid methyl ester
Methyl 2-(bromomethyl)propenoate
α-(Bromomethyl)acrylic acid methyl ester
[Molecular Formula]

C5H7BrO2
[MDL Number]

MFCD00011697
[Molecular Weight]

179.01
[MOL File]

4224-69-5.mol
Chemical PropertiesBack Directory
[Appearance]

Clear colorless to slightly brownish liquid
[Boiling point ]

35-37 °C/1.3 mmHg (lit.)
[density ]

1.489 g/mL at 25 °C(lit.)
[refractive index ]

n20/D 1.490(lit.)
[Fp ]

173 °F
[storage temp. ]

2-8°C
[solubility ]

Chloroform (Slightly), Methanol (Slightly)
[form ]

Liquid
[color ]

Clear colorless to slightly brownish
[BRN ]

1852481
[Stability:]

Light Sensitive
[InChI]

InChI=1S/C5H7BrO2/c1-4(3-6)5(7)8-2/h1,3H2,2H3
[InChIKey]

CFTUQSLVERGMHL-UHFFFAOYSA-N
[SMILES]

C(OC)(=O)C(CBr)=C
[CAS DataBase Reference]

4224-69-5(CAS DataBase Reference)
[NIST Chemistry Reference]

Methyl 2-(bromomethyl)acrylate(4224-69-5)
[EPA Substance Registry System]

2-Propenoic acid, 2-(bromomethyl)-, methyl ester (4224-69-5)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection .
[RIDADR ]

UN 2810 6.1/PG 2
[WGK Germany ]

3
[RTECS ]

AS4900000
[F ]

8-10
[HS Code ]

29161900
Hazard InformationBack Directory
[Chemical Properties]

Clear colorless to slightly brownish liquid
[Uses]

Methyl (2-bromomethyl)acrylate (MBrMA) may be used as chain transfer agents in the emulsion polymerization of methyl methacrylate (MMA) and styrene. MBrMA can undergo nucleophilic substitution of carboxylic acid to form methyl 2-(acyloxymethyl)acrylates.
[Synthesis Reference(s)]

Organic Syntheses, Coll. Vol. 7, p. 319, 1990
Synthetic Communications, 16, p. 387, 1986 DOI: 10.1080/00397918608057713
[Synthesis]

Methyl 2-(hydroxymethyl)acrylate

15484-46-5

Methyl 2-(bromomethyl)acrylate

4224-69-5

The general procedure for the synthesis of methyl 2-(bromomethyl)acrylate from methyl 2-(hydroxymethyl)acrylate was as follows: 10.2 g of 2-hydroxymethyl methacrylate produced in the previous step was dissolved in 150 mL of acetonitrile, followed by the slow dropwise addition of 4 mL of phosphorus tribromide. After the dropwise addition, the reaction was stirred continuously for 4 hours at room temperature. Upon completion of the reaction, the reaction was quenched by the addition of an appropriate amount of water, followed by removal of the acetonitrile solvent by decompression distillation with a rotary evaporator. To the residue, 100 mL of water was added and extracted twice using ethyl acetate (100 mL each time). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent, resulting in 13.5 g of colorless liquid product in 86% yield.

[References]

[1] Tetrahedron Asymmetry, 2013, vol. 24, # 7, p. 395 - 401
[2] Patent: CN107915668, 2018, A. Location in patent: Paragraph 0018
[3] Organic Letters, 2011, vol. 13, # 15, p. 3864 - 3867
[4] Tetrahedron Letters, 2014, vol. 55, # 13, p. 2075 - 2077
[5] Chemical Communications, 2014, vol. 50, # 96, p. 15216 - 15219
Spectrum DetailBack Directory
[Spectrum Detail]

Methyl 2-(bromomethyl)acrylate(4224-69-5)1HNMR
Methyl 2-(bromomethyl)acrylate(4224-69-5)FT-IR
Methyl 2-(bromomethyl)acrylate(4224-69-5)IR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Methyl 2-(bromomethyl)acrylate, 96%(4224-69-5)
[Sigma Aldrich]

4224-69-5(sigmaaldrich)
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