| Identification | More | [Name]
4-(BROMOMETHYL)PHENYLACETIC ACID | [CAS]
13737-36-5 | [Synonyms]
4-(BROMOMETHYL)PHENYLACETIC ACID
4-(CARBOXYMETHYL)BENZYL BROMIDE
BR-PAM-LINKER
PAM ACID
P-(BROMOMETHYL)PHENYLACETIC ACID
4-(Bromomethyl)
4-(Bromomethyl)phenylacetic acid 97%
4-(BROMOMETHYL)PHENYLACETIC ACID 96+%
p-(Carboxymethyl)benzyl bromide | [Molecular Formula]
C9H9BrO2 | [MDL Number]
MFCD00010632 | [Molecular Weight]
229.07 | [MOL File]
13737-36-5.mol |
| Chemical Properties | Back Directory | [Appearance]
White to light beige crystalline powder | [Melting point ]
179-183 °C(lit.)
| [Boiling point ]
343.1±22.0 °C(Predicted) | [density ]
1.565±0.06 g/cm3(Predicted) | [storage temp. ]
Store at RT. | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R42:May cause sensitization by inhalation. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
UN3261 | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29163990 |
| Hazard Information | Back Directory | [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 |
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