4-Bromomandelic acid

Base Information

• Chemical Name: 4-Bromomandelic acid
• CAS No.: 6940-50-7
• Deprecated CAS: 7021-04-7
• Molecular Formula: C8H7BrO3
• Molecular Weight: 231.046
• Hs Code.: 29181980
• European Community (EC) Number: 230-085-1,677-948-2
• NSC Number: 60138
• UNII: 4429SL694F
• DSSTox Substance ID: DTXSID40871938
• Nikkaji Number: J8.865J
• Wikidata: Q27258692
• ChEMBL ID: CHEMBL3247386
• Mol file: 6940-50-7.mol

Synonyms:4-Bromomandelic acid;6940-50-7;2-(4-bromophenyl)-2-hydroxyacetic acid;p-Bromomandelic acid;4-Bromomandelicacid;4-Bromo-dl-mandelic acid;Mandelic acid, p-bromo-;7021-04-7;Benzeneacetic acid, 4-bromo-.alpha.-hydroxy-;UNII-4429SL694F;EINECS 230-085-1;NSC 60138;NSC-60138;4429SL694F;4-Bromo-Hydroxybenzeneaceticacid;P-Bromo mandelic acid;4-Bromo-alpha-hydroxyphenylacetic acid;p-brommandelsaure;4-Bromo-a-hydroxyphenylacetic acid;MFCD00004232;4-bromo-mandelic acid;p-bromophenylglycolic acid;(2R)-2-(4-Bromophenyl)-2-hydroxyacetic acid>99%ee;ChemDiv2_000136;SCHEMBL323295;DL-P-BROMOMANDELIC ACID;DL-4-BROMOMANDELIC ACID;CHEMBL3247386;ISOTHIAZOLINE1,1-DIOXIDE;DTXSID40871938;hydroxy(4-bromophenyl)acetic acid;P-BROMOMANDELIC ACID [MI];HMS1369G04;4-bromo-phenyl-hydroxy-acetic acid;NSC60138;(4-bromo-phenyl)-hydroxy-acetic acid;hydroxy-(4-bromo-phenyl)-acetic acid;AKOS002676240;AKOS016046697;4-Bromo-alpha-hydroxybenzeneacetic acid;P-BROMOMANDELIC ACID, (+/-)-;AC-19771;AS-11853;BP-12313;Benzeneacetic acid, 4-bromo-alpha-hydroxy-;B0609;CS-0157607;FT-0617896;(+/-)-4-bromo-alpha-hydroxyphenylacetic acid;EN300-78925;SR-01000390729;SR-01000390729-1;W-104626;4-Bromo-DL-mandelic acid, technical, >=90% (HPLC);Q27258692;Z788000726

Chemical Property of 4-Bromomandelic acid

Chemical Property:

• Appearance/Colour: White to beige crystalline powder or flakes
• Vapor Pressure: 4.96E-07mmHg at 25°C
• Melting Point: 116-118 °C(lit.)
• Refractive Index: 1.4730 (estimate)
• Boiling Point: 397.5 °C at 760 mmHg
• PKA: 3.14±0.10(Predicted)
• Flash Point: 194.2 °C
• PSA: 57.53000
• Density: 1.759 g/cm³
• LogP: 1.56710
• Storage Temp.: Store below +30°C.
• Water Solubility.: Slightly soluble in water.
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 229.95786
• Heavy Atom Count: 12
• Complexity: 164

Purity/Quality:

99% ^*data from raw suppliers

4-Bromomandelicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C1=CC(=CC=C1C(C(=O)O)O)Br
• Uses: 4-Bromomandelic acid is used as a pharmaceutical intermediate. 4-bromomandelic acid is mainly used as an analytical reagent for zirconium. 4-Bromo-DL-mandelic acid (4-Bromo-α-hydroxyphenylacetic acid) may be used in the synthesis of (.+-.)-methyl 4-bromo-α-hydroxyphenylacetate.

Technology Process of 4-Bromomandelic acid

There total 37 articles about 4-Bromomandelic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

carbon dioxide (124-38-9,18923-20-1) + 4-bromo-benzaldehyde (1122-91-4) → 4-bromo-DL-mandelic acid (6940-50-7)

Guidance literature:

With Tetrapropylammonium chloride; In acetonitrile; at 20 ℃; for 10h; under 760.051 Torr; Electrochemical reaction;

DOI:10.14233/ajchem.2021.23090

Reference yield: 88.0%

para-bromoacetophenone (99-90-1) → 4-bromo-DL-mandelic acid (6940-50-7)

Guidance literature:

With selenium(IV) oxide; In 1,4-dioxane; water; at 90 ℃; for 24h;

DOI:10.3184/174751912X13551435784584

Reference yield: 87.4%

(4-bromophenyl)(fluoro)acetic acid (109050-30-8) → (R)-2-(4-bromophenyl)-2-hydroxyacetic acid (6940-50-7,7021-04-7,123484-90-2,32189-34-7) + C8H6BrFO2

Guidance literature:

With fluoroacetate dehalogenase RPA₁₁₆₃-W₁₈₅T; for 1h; enantioselective reaction; Catalytic behavior; Kinetics; Enzymatic reaction;

DOI:10.1021/acscatal.9b04804

upstream raw materials:

2,2-dibromo-1-(4-bromophenyl)ethan-1-one

1-(4-bromophenyl)-2,2,2-trichloroethan-1-ol

para-bromoacetophenone

[bis(acetoxy)iodo]benzene

Downstream raw materials:

(R)-2-(4-bromophenyl)-2-hydroxyacetic acid

α-hydroxy-(p-bromophenyl)-acetic acid methyl ester

(+)-p-bromo-O-acetylmandelic acid

(-)-p-bromomandelic acid

Refernces

• 1、 Singh, Kishanpal,Sohal, Harvinder Singh,Singh, Baljit. "Synthesis of α-hydroxycarboxylic acids from various aldehydes and ketones by direct electrocarboxylation: A facile, efficient and atom economy protocol". . p. 839 - 845. Retrieved 2021/04/09.
• 2、 Chen, Bo,Li, Min,Li, Yanwei,Ma, Ming,Tian, Shaixiao,Tong, Wei,Wang, Jian-Bo,Xu, Guangyu,Yue, Yue,Zhang, Hongxia. "Semirational Design of Fluoroacetate Dehalogenase RPA1163 for Kinetic Resolution of α-Fluorocarboxylic Acids on a Gram Scale". . p. 3143 - 3151. Retrieved 2020/03/23.