| Identification | More | [Name]
4-Bromomethylbenzoic acid | [CAS]
6232-88-8 | [Synonyms]
4-(BROMOMETHYL)BENZOIC ACID
4-CARBOXYBENZYL BROMIDE
A-BROMO-P-TOLUIC ACID
AKOS BBS-00006715
ALPHA-BROMO-P-TOLUIC ACID
ALPHA-BROMO-P-TOLUYLIC ACID
P-(BROMOMETHYL)BENZOIC ACID
P-CARBOXYBENZYL BROMIDE
RARECHEM AL BO 0068
4-(bromomethyl)-benzoicaci
alpha-bromo-para-toluic acid
alpha-bromotoluic acid
Benzoic acid, 4-(bromomethyl)-
à-bromo-p-toluic acid
α-bromo-p-toluic acid | [EINECS(EC#)]
228-343-3 | [Molecular Formula]
C8H7BrO2 | [MDL Number]
MFCD00002567 | [Molecular Weight]
215.04 | [MOL File]
6232-88-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white to beige crystalline powder | [Melting point ]
224-229 °C(lit.)
| [Boiling point ]
252.95°C (rough estimate) | [density ]
1.5313 (rough estimate) | [refractive index ]
1.5500 (estimate) | [storage temp. ]
Store below +30°C. | [form ]
Crystalline Powder | [pka]
4.10±0.10(Predicted) | [color ]
White to beige | [Water Solubility ]
Soluble in water. | [BRN ]
1862870 | [InChI]
InChI=1S/C8H7BrO2/c9-5-6-1-3-7(4-2-6)8(10)11/h1-4H,5H2,(H,10,11) | [InChIKey]
CQQSQBRPAJSTFB-UHFFFAOYSA-N | [SMILES]
C(O)(=O)C1=CC=C(CBr)C=C1 | [CAS DataBase Reference]
6232-88-8(CAS DataBase Reference) | [EPA Substance Registry System]
6232-88-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,C | [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 . | [RIDADR ]
3261 | [WGK Germany ]
3
| [F ]
19-21 | [Hazard Note ]
Irritant | [TSCA ]
Yes | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29163900 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
white to beige crystalline powder | [Uses]
4-(Bromomethyl)benzoic Acid is an intermediate in the synthesis of Eprosartan (E590100), a prototype of the imidazoleacrylic acid angiotensin II receptor antagonists used as an antihypertensive agent. | [Synthesis]
In a 100 mL round-bottomed flask, 40 mL of carbon tetrachloride was added as solvent, 3.00 g of p-methylbenzoic acid as starting material, 4.00 g of N-bromosuccinimide (NBS) as bromination reagent, and 0.1 g of azobisisobutyronitrile (AIBN) as initiator. The reaction mixture was stirred and refluxed at 90 °C and the reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was cooled to room temperature followed by filtration. The filter cake was washed with warm water to remove the succinimide by-products generated in the reaction. After drying, 4.02 g of p-bromomethylbenzoic acid was obtained with a melting point of 231-232°C in 84% yield. | [Purification Methods]
Crystallise the acid from pKEst Me2CO. [Beilstein 9 IV 1745.] | [References]
[1] Chemistry - A European Journal, 2018, vol. 24, # 7, p. 1619 - 1630
[2] Organic Process Research and Development, 1998, vol. 2, # 4, p. 261 - 269
[3] Patent: CN108570012, 2018, A. Location in patent: Paragraph 0020; 0024; 0025
[4] Patent: CN108623537, 2018, A. Location in patent: Paragraph 0046; 0047; 0048
[5] Journal of Organic Chemistry, 1998, vol. 63, # 17, p. 6023 - 6026 |
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