4-(BROMOMETHYL)PHENYLACETIC ACID

4-(BROMOMETHYL)PHENYLACETIC ACID Property

Melting point:

179-183 °C(lit.)

Boiling point:

343.1±22.0 °C(Predicted)

Density 

1.565±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

form 

Crystalline Powder

pka

4.24±0.10(Predicted)

color 

White to light beige

BRN 

2360711

InChI

InChI=1S/C9H9BrO2/c10-6-8-3-1-7(2-4-8)5-9(11)12/h1-4H,5-6H2,(H,11,12)

InChIKey

WCOCCXZFEJGHTC-UHFFFAOYSA-N

SMILES

C1(CC(O)=O)=CC=C(CBr)C=C1

CAS DataBase Reference

13737-36-5(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38-42

Safety Statements 

26-36

RIDADR 

UN3261

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

8

PackingGroup 

III

HS Code 

29163990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

H315Causes skin irritation

H318Causes serious eye damage

H319Causes serious eye irritation

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P284Wear respiratory protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P342+P311IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

4-(BROMOMETHYL)PHENYLACETIC ACID Chemical Properties,Usage,Production

Chemical Properties

White to light beige crystalline powder

Uses

4-(Bromomethyl)phenylacetic acid was used as the precursor for serine protease inhibitor. It was also used in the synthesis of a novel crown ether receptor and 4-(acetoxymethyl)phenylacetic acid by reacting with excessive sodium acetate and acetic acid.

Synthesis

The general procedure for the synthesis of 4-bromomethylphenylacetic acid from p-toluacetic acid was as follows: 24 g of p-toluacetic acid was added to 250 ml of hydrogen trichloride, followed by 75 ml of chlorobenzene as a solvent. To the reaction system, 30 g of N-bromosuccinimide (NBS) and 0.5 g of benzoyl peroxide were added as initiator. Mechanical stirring was turned on and the reaction was heated to 85°C and under incandescent light. The reaction temperature will automatically rise to 110 °C, at which point the reaction temperature needs to be controlled in the range of 90-110 °C. The reaction continues at this temperature for 8 hours, during which the progress of the reaction is monitored by TLC. Upon completion of the reaction, the reaction mixture is cooled and the solid product will precipitate. The solid is collected by filtration and the filter cake is washed with plenty of water. The filter cake was filtered to dryness as much as possible, resulting in 33.7 g of white solid product in 91.9% yield and 99.2% HPLC purity.

References

[1] Patent: CN106905135, 2017, A. Location in patent: Paragraph 0018; 0019; 0020; 0021
[2] Bulletin of the Chemical Society of Japan, 1988, vol. 61, # 7, p. 2467 - 2472
[3] European Journal of Organic Chemistry, 2006, # 18, p. 4135 - 4146
[4] Journal of the Chemical Society, Chemical Communications, 1993, # 4, p. 399 - 401
[5] Patent: EP496548, 1992, A1